Lenny's Written Position
One of the clearest markers of a future generational company is ambition that borders on ludicrous, where the founder's goals sound crazy to most people.
The quality of the founders matters above all other variables when evaluating whether to join a startup early.
It is more important for founders to learn quickly and adapt than to have a good initial strategy.
Judging a startup by its current product quality is a trap because almost every iconic product started as something rough or even completely different from what made it successful.
Instead of evaluating a startup's current product, look for strong customer pull where users cannot stop talking about the product even when it is early and the market is niche.
None of the serial early employees at iconic companies found their jobs through applications or recruiters; their paths were serendipitous and driven by personal connections.
Look for 'Jurassic Park moments' at startups — early prototypes or demos that leave you breathless and feeling like you are being given a clear glimpse of the future, even if the product is ugly and small.
When starting an ecosystem strategy, pick one partner program that fits your product and audience and prove it works before expanding, rather than launching every kind of partnership at once.
The name you choose for a product or company may be the single most important branding decision you make, yet it is too often delegated to junior staff or tackled in group brainstorming sessions.
A product succeeds because it solves a problem for people, and the problem should be easy to communicate in a sentence or two that resonates with the target audience.
A startup is a company designed to grow fast -- being newly founded, working on technology, or taking venture funding are not essential; the only essential thing is growth.
Schlep blindness causes founders to avoid hard, messy problems in favor of easy ones, but ambitious ideas are doubly valuable because they have intrinsic value and less competition since everyone else is frightened off.
The best way to manage scaling is to give away your Legos -- resist the instinct to grab back responsibilities from new hires and instead find a bigger, better tower to build.
Burnout conquerors use four tests to evaluate roles: the relationship test (who you work with), the Sunday test (how you feel before the work week), the energy test (does the work energize you), and the values alignment test (does culture match your core values).
Every startup and modern product team should be using Linear for task tracking, project organization, and roadmap building — and at this point, most are.
Lovable reached $100 million ARR just eight months after launch, making it the fastest-growing company in history — faster than even Cursor.
Bolt grew from 0 to $40 million ARR in five months and is used by 72% of Fortune 500 product teams, differentiating itself by integrating frontier agents like Claude Code rather than relying on homegrown agents.
Startup founders are the happiest people in tech, scoring highest on career optimism, job enjoyment, engagement, and belonging while having the lowest burnout.
Small-company employees outperform large-company counterparts on nearly every work sentiment measure, and company size is one of the strongest predictors of positive sentiment.
Enabling teams to have maximal autonomy, ownership, and purpose are the secret ingredients that make founders 3-4x more optimistic and almost 3x happier than everyone else in tech.
Prototypes should replace PRDs in fast-moving environments because PRDs block valuable design and engineering work, are almost never up-to-date, and become watered-down versions of the actual product once it exists.
Sharing raw work-in-progress with stakeholders builds hype and investment rather than depleting trust, as demonstrated by an engineer posting over 70 prototype videos in Slack before launch.
The best team members are those who opt in rather than being assigned, and if you need to sell someone really hard to join your project, they are probably not the right fit.
You must first build trust by executing well on assigned projects (the meat and potatoes) before leadership will fund your own ambitious ideas (the souffle).
Over a third of Palantir's PM alumni have started a company, making it the dominant company for producing founder PMs.
Over 20% of Chime's PM alumni go on to not just start a company but also raise a Series A, making it the top company for producing venture-scale founders.
Roughly 4.5% of YC companies become unicorns compared to the 2.5% rate for other venture-backed seed-stage startups, and around 45% go on to raise a Series A versus the 33% industry average.
YC has shifted from being primarily a consumer investor to a B2B investor, with over 75% of recent batch companies being B2B, driven by the fact that most large consumer apps have already been invented.
The top four YC companies (Airbnb, DoorDash, Coinbase, Instacart) account for more than 84% of all market value created, demonstrating extreme power law distribution in startup outcomes.
More than 50% of YC companies are still alive after 10 years, compared to the average startup lifetime of about five years, with only 13% having gone out of business.
Solo founders are at a growing disadvantage at YC, with the proportion accepted declining to around 10% in the latest batches despite YC officially saying it is not a deal-breaker.
99% of YC's financial returns have come from U.S.-founded companies despite accepting startups from many countries, with the most valuable European YC company (GoCardless) valued at only $2.1 billion.
The Foundation Sprint is a two-day workshop that helps teams define their Founding Hypothesis by clarifying customer, approach, and differentiation before building anything.
Products click with customers when they make a simple, compelling promise that combines a clear target customer, their problem, a differentiated approach, and why it beats competitors.
If you ask three co-founders to write down their startup's target customer, you typically get three different answers, revealing that obvious strategic alignment is rarely obvious.
Google Meet succeeded only after the team stripped away complex features like 3D virtual conference rooms and focused on the core hypothesis of being the fastest and easiest video call software.
Fintech companies dominate the top 10 PM career accelerators with 5 out of 10 spots, likely because fintech work is on hard mode with complex risk, regulatory, and compliance challenges.
Palantir is the standout company for fostering founders, with almost a quarter of its PM alumni going on to start their own company.
75% of tech professionals now prioritize salary over equity when evaluating job offers, a significant shift from the traditional 'maximize equity' wisdom.
Equity skepticism is widespread, with many tech workers describing equity as 'Monopoly money' or 'a lottery ticket' after past experiences where equity failed to deliver.
You should aim for 24 to 36 months of runway with a 25% buffer when raising a seed round, as the median time from seed to Series A is 23 months.
Most seed rounds are now $2M to $4M with a typical post-money valuation of around $20M and approximately 15% equity sold.
Creating FOMO among investors by compressing your fundraise into a 2-3 week window and collecting smaller angel checks first is the most effective strategy for raising a seed round.
Raising money too early teaches founders how to spend rather than earn, and the skill of making more than you spend takes considerable practice time to master.
Who introduces you to prospective investors matters far more than most founders realize, with successful portfolio founders being the highest-influence intro source.
A founder's own conviction across commitment, work, and insight is perhaps the single most predictive variable in raising seed capital.
Most early AI apps have a 'tourist' problem with shockingly low retention, and two in five gen AI products still haven't made a single dollar despite millions spent building them.
The first-pass AI product is often a bolt-on or simple chat experience; the high-value experience requires a deeper rethink after understanding what the technology really provides.
Companies with proprietary or uniquely structured data sets will have a durable advantage in AI because models are becoming commoditized, and designers will be more important than ever.
Companies almost always start with a functional model and should only consider a GM model after having multiple proven product groups, predictable business outcomes, and significant scale.
Feature factories can be the right choice for some CEOs, especially visionary founders with a clear view of what needs to be built, and VCs often back these types of leaders pattern-matching to Elon Musk and Steve Jobs.
There are two distinct types of startup pivots: ideation pivots (changing direction before meaningful traction, usually within three months) and hard pivots (changing direction with a live product and real users, usually around the one-year mark).
The two clearest signs it is time to pivot are persistent lukewarm interest (low retention, growth plateau) and realizing the idea will never be as big as originally thought.
The most common strategy for finding a better idea after a pivot is going all in on an internal tool or piece of tech that showed unexpected pull, followed by narrowing focus to one feature users loved.
The best test for whether to pivot or persevere is asking yourself whether you have more or less conviction in the problem and solution now than when you started, knowing everything you know today.
One in three B2B startups and one in five consumer startups pivot before finding their big idea.
Companies only pivot into B2B, never out of it; no company in the dataset successfully pivoted from B2B to B2C.
Over a fourth of successful pivots came from finding pull for a piece of tech the team built for themselves while building their original unrelated business.
Startups that do well on Product Hunt invest 50 to 120 hours preparing for launch, and most founders launch too late; launching early and often is recommended to get market signal.
Every business can be distilled into a simple equation, and until you can express your business as one, you do not fully understand it because the equation reveals which levers have the most impact.
If your startup is not taking off, the most likely cause is not talking to enough users, which means you have not found product-market fit, and nothing else really matters until you do.
Your initial target audience should be almost comically narrow with at least three narrowing characteristics, because focus enables solving one problem better than anyone, and narrow audiences are easier to reach and convert.
About 20% of successful consumer companies and 40% of successful B2B companies pivoted at least once in their early history.
In consumer, if product-market fit is not immediate, it usually takes 6 to 18 months; in B2B, the median time is two years, extended further for products requiring network effects.
First-principles thinking is approaching problems with a beginner's mind by doing the hard work of figuring out what is actually true rather than working within existing assumptions, and many of history's biggest breakthroughs came from this approach.
A single-player utility mode is critical kindling for social products because it unlocks retention independent of network size, giving you time to iterate on social features without the destructive inverse K-factor that kills purely social apps.
Hyper-personalizing a product to feel like it was built just for a specific community drives dramatically faster adoption; Saturn achieved majority student body adoption at schools within hours by white-labeling apps with school colors and mascots.
Doing unscalable things is acceptable and even valuable at the start of a consumer app because the operational lessons extracted from manual processes provide the insights needed to later productize and achieve national scale.
Going freemium and removing onboarding friction nearly destroyed Equals' business: while they initially 4x'd active companies, engagement and retention tanked, and they could not grow their active company base beyond the initial surge of pent-up demand.
Freemium requires five conditions to work: a massive potential user base, very short time to value, a foundational product for end users, low incremental cost to serve, and free users contributing to your growth model through viral loops or network effects.
The typical B2B company waited two to three years to hire their first product manager, usually at 10-15 engineers and 15-25 total employees.
More than half of top B2B companies hired their first PM before finding product-market fit, counter to conventional advice.
Many first PMs come from internal transfers rather than external hires, because trust and existing product knowledge make them more effective.
Founders should not delegate product strategy to their first PM; the PM should own execution while founders retain strategic direction.
An ICP must describe a single market segment where the value of solving the problem and the way to reach them are roughly the same; allowing your ICP to fray across use cases confuses every downstream decision.
Horizontal products only win when a specific audience encounters enough use cases that they want one tool to address them all, as Figma did for designers and Notion did for product managers.
True switching costs include politics, emotions, career ambitions, competing priorities, and sheer laziness far beyond the time and money to install a new solution, which means old and clunky products can be much more durable than they appear.
Founders should not confuse people rooting for them (investors, personal connections, early supporters) with real market signal, because the earliest deals done on personal relationships do not prove the business can run on its own.
Top B2B startups took on average about 2 years from founding to hit $1M ARR, and roughly 1.5 years after closing their first customer.
B2B founders should charge sooner and more than they think; founders are biased to undervalue their product, and early revenue provides freedom and discipline.
A practical pricing strategy for early B2B startups is to keep doubling prices until customers push back, then revisit pricing every six to twelve months.
Over two-thirds of top B2B companies hired an engineer as employee number one, and 100% hired at least one engineer among their first three hires.
Every B2B founder should start with founder-led sales and wait until $300-500K ARR before hiring their first full-time salesperson.
Your first sales hire should be a 'hungry senior AE' who can break new ground rather than someone who excels only at repeatable processes from later-stage companies.
Cold outreach through LinkedIn and GitHub is the second most common channel for finding early startup employees, and is accessible to any founder regardless of network size.
The median time from idea to feeling product-market fit in B2B is roughly 2 years, with 9-18 months of iteration after launching a working product.
Product-market fit is never a binary yes-or-no moment but a gradual process of finding fit with larger and larger market segments, and many founders never fully feel they have achieved it.
The PMF journey in B2B follows five steps: get one company to love your product, get one to pay meaningful money, get multiple companies paying, notice a shift from push to pull, then grow consistently.
B2B founders should spend 50% of their time talking to customers and 50% building; most technical founders over-index on building and waste time solving problems without real traction behind them.
None of the seven strategies for finding your first 10 B2B customers scale, and that is precisely why they work: in B2B it always starts with hand-to-hand combat.
Trust is the secret weapon for winning early B2B customers; start with channels that have the most innate trust (personal network) and work outward to cold outbound.
Cold outbound works for finding early B2B customers if done creatively; Figma's Dylan Field built a custom script to find influential designers on Twitter, and Retool used filtered Crunchbase data to target operationally heavy companies.
Every successful B2B startup landed on at least three attributes to describe their ICP, and founders should aim to get super-specific and almost comically narrow with their initial ICP definition.
Outbound sales signal is the cleanest data for identifying your ICP; leads from investors and friends muddy the signal because people may take meetings out of relationship obligation rather than genuine interest.
Four signs you are converging on the right ICP are: a significant increase in conversion rate, a significant increase in enthusiasm, a stronger desire from prospects to take action now, and 'the nod' when you describe the pain.
Growth teams should not be hired before product-market fit is validated; growth is about increasing distribution of core product value, and if PMF does not exist, there is nothing to grow.
90% of the time, acquisition is the first goal new growth teams should take on, because there is more volume for experimentation and the biggest drop-offs occur in the acquisition stage.
About 40% of top B2B startups pivoted at least once before finding their winning idea, a much higher pivot rate than the approximately 20% in B2C.
Founders spoke to a median of 30 potential customers before feeling confident their idea was solid, with some like Zip speaking to 75 people in just 2-3 weeks.
The strongest validation signal is deep emotional reaction from potential customers; when half the people you talk to start cursing about their current solution unprompted, you know you have found real pain.
There are three reliable paths for discovering a great B2B startup idea: past pain from a previous company, pondering and probing a space while talking to dozens of customers, or identifying present pull from something you already built.
Every prosumer collaboration product including Figma, Notion, Coda, Airtable, Miro, and Slack spent three to four years wandering in the dark before finding something that clicked.
A great B2B startup idea requires three ingredients: the problem is important to many people willing to spend money, existing solutions are doing a subpar job (Delta-4 framework), and you are personally excited about spending years solving it.
Shopify's internal priorities mantra is: first make the best product for merchants, second make money to do more of number one, and third never reverse priorities one and two.
Forward-deploying engineers to literally do the customer's job with your product for months at a time produces an order of magnitude more customer understanding than interviews or phone calls.
Hiring the literal world's number one person in each critical discipline creates cascading advantages because top people have disproportionately more access to knowledge, opportunity, and other top talent.
Delay building a PM organization as long as possible; putting great engineers directly in front of customer problems often produces better results than adding a PM layer that introduces lossy communication.
Ramp reached $100 million ARR with fewer than five PMs and fewer than 50 engineers, demonstrating that extreme efficiency is possible by restricting headcount.
If your speed of shipping is extremely high, the cost of being wrong is much lower, making velocity itself a competitive advantage.
Hiring people with high slope (learning ability) over high intercept (current domain expertise) is critical at fast-growing companies because scope will be much bigger in six months.
A venture-scale startup must have a path to $100 million per year in revenue and $1 billion+ valuation within 10 years.
When a great team meets a lousy market, market wins, making market size more important than team quality.
Making something people want is necessary but not sufficient for a venture-scale business; you also need enough people who want it and the ability to make enough money from them.
Long-term sustainable growth requires all three pieces: ongoing product improvements, ongoing events that spread the word, and a well-oiled growth engine.
Even the most viral products like Dropbox, Facebook, Snapchat, and Instagram show roughly linear growth when you zoom out, with viral moments appearing as short-lived S-curves.
Founders should optimize their investor network for eigenvector centrality (how many people your connections know) rather than degree centrality (how many people you know directly).
It's almost always the founder's fault when they aren't getting value from their investors, because investors have little context and need targeted, time-bounded, specific asks.
Investor requests are not like precious gems with limited uses; people like being helpful, and the failure mode is making bad asks, not making too many asks.
Building a startup in stealth mode is always a mistake because it inhibits frequent market signal and greatly increases time to product-market fit.
Pre-PMF, you want either overwhelming market pull or no sales at all; steady sales with no acceleration is a dangerous riptide that can trap you.
VC funding creates pressure that can delay honest assessment of product-market fit because founders tell themselves that if investors backed them, they must be on the right path.
Headcount is a cost center, not a sign of progress, and the only metric that merits congratulations is product traction and product-market fit.
A strategy is essentially a short description of your plan to win, with 3 to 5 concrete investments that, if you get right, will bring you closer to winning.
When just starting out, focus energy on kickstarts and turbo boosts until your growth engine begins to drive the majority of growth, then invest in lubricants.
The nine most common kickstart tactics for getting your first 1,000 users include sharing with friends, reaching out to targeted strangers, pitching where your audience hangs out, enlisting influencers, getting press, creating viral content, physical placement, hosting events, and being first on a platform.
Geographic expansion is one of the biggest growth accelerants a startup can have but is something you can only really do once, and normally happens post-PMF but before the growth engine is at full steam.
The majority of startups grow primarily through just one growth engine, and a common pitfall is trying to invest in too many engines at once without nailing any.
For consumer startups there are only three feasible growth engines since relying on sales is rarely economical: SEO, paid ads, and virality.
You will likely grow primarily through virality if you have to share the product to use it, the product is only fun with friends, or the product is super-fun to share.
At Airbnb, word of mouth was the biggest growth driver early on, accounting for over 50% on the guest side and over 70% on the host side.
The four clearest signs of product-market fit in decreasing confidence are: cohort retention curves flatten, explosive growth through word of mouth, users feel the product is a must-have, and strong unit economics.
Product-market fit should be thought of as a spectrum of confidence that changes over time rather than a binary you-have-it or you-don't one-way door.
There are only seven reliable ways to kickstart consumer growth and acquire your first 1,000 users: friends and colleagues, targeted strangers, going where your audience hangs out, enlisting influencers, getting press, creating viral content, and getting physical placement.
There are four strategies for crafting a remarkable hook: identify what is unique about your product versus alternatives, listen to how your most obsessed users describe it, determine what job your product does for people, and find what about your product grabs attention.
If your pitch is not resonating, one of three things is happening: your pitch is bad, you are pitching the wrong people, or your product is not something people want.
When deciding who to target early on, the target customer definition must be almost comically narrow, aiming for three very specific characteristics of your ideal early adopter.
Pinterest initially failed by targeting tech friends, but when Ben Silbermann found that 30-something female bloggers at Alt Summit were the right audience, the product reached over a million users within a year.
TikTok's early growth strategy treated the platform like a new country where initial wealth should be distributed to a small number of creators to make them role models that attract migration from established platforms.
There are three common approaches to coming up with a startup idea: market first (investigate a space then find a problem), experience ripe for improvement (find a broken consumer experience), and problem first (start with a problem you have experienced firsthand).
Sitting on a couch brainstorming startup ideas in a bubble is counterproductive because all ideas seem flawed without market feedback; founders should instead get out into the market and have real conversations.
There are six effective ways to build trust in a new marketplace: reviews, verifying supply, leaning on social proof, creating a perception of quality, providing a safety net, and delivering magic.
The magic moment for marketplace trust is when both sides experience something better than expected: for Thumbtack pros it was getting hired and paid for their first job, and for consumers it was finding a pro better than through word of mouth.
The three patterns of winning B2C subscription businesses are an obsession with efficiency, alignment between product strategy and acquisition strategy, and a singular focus on building a magical sticky product through rapid iteration.
Duolingo built a massive user base through word of mouth and no paid marketing by offering all learning content for free, because limiting free experience heavily slows organic growth since only payers can tell friends.
Future deliberately fired perfectly happy paying members in early cohorts to keep costs low and iterate on retention, only expanding operations once three-month retention consistently hit their anomalously high bar.
There are three common approaches to coming up with a startup idea: market first, experience ripe for improvement, and problem first, and these methods correlate with specific company categories.
Vanta's founder knew she was onto something when people she had not even spoken to started reaching out directly to ask about using the product, indicating genuine market pull.
For early-stage B2B businesses, investors focus on how quickly they ramp to $1M ARR after going live rather than month-over-month growth percentages, with reaching $1M ARR within 12 months considered good and 9 months considered great.
Best-in-class SaaS companies follow a triple-triple-double-double-double ARR growth pattern after reaching $1M in revenue.
The founding insight for most great marketplace businesses is principally a 'liquidity hack' such as Uber paying drivers to circle neighborhoods, Airbnb paying for professional photos, and Faire guaranteeing items would sell.
Podcast Moments
“You have to know the difference between a megatrend and a hype cycle. When there's a megatrend, don't fight it. AI is a megatrend, one of the most foundational movements that we have seen in human history.”
Jeetu Patel · Jeetu Patel
“The six things you need to build a great company, in descending order: timing, market, team, product, brand, distribution. You don't have all six, you don't win. A great team in a bad market gets dragged down — the market always wins.”
Jeetu Patel · Jeetu Patel
“Permission to play means asking: is this logical for us? Do we have the route to market for mass scale distribution? If you dissipate your caloric burn across too many areas, nothing gets enough girth to drive all the way through. Be extremely selective where you expend your calories.”
Jeetu Patel · Jeetu Patel
“Persistence beats intellect, and stamina beats intellect any day of the week, twice on Sunday. The biggest reason successful leaders win is not that they're the smartest — it's that they have enormous staying power in the game.”
Jeetu Patel · Jeetu Patel
“The platform that you choose and the quality of problems that you pick to solve determine a lot of the path of success for you. Harder problems attract better people, and business is a team sport.”
Jeetu Patel · Jeetu Patel
“I look for four things in CEOs — my LOCK algorithm. L is for lovable — can I envision following this person? O is obsession with the problem. C is chip on the shoulder. K is deeply knowledgeable about the domain. And I'd add S for student — the best ones are deep, deep students of the game.”
Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot) · Brian Halligan
“Starting a company has never been easier. The flip side is the number of companies formed is going to mushroom. There's so much noise and competition, it's just going to be hard to stand out and really accelerate and scale. It's never been easier to start, never been harder to scale.”
Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot) · Brian Halligan
“If you want to kill a plant, have two people water it. Every CEO at the adults' table has gone through this and they are religious about the DRI — directly responsible individual.”
Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot) · Brian Halligan
“EV is enterprise value, TV is your team's value, MEV is your value. Immature managers solve for TV over EV. We always put on the wall: solve for CV, then EV, then TV, then MEV. Customers first, then company, then team, then yourself.”
Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot) · Brian Halligan
“I always valued optionality, but there's a massive tax in optionality when you can move this fast. Planning cycles used to be a year, now they're three months.”
Sequoia CEO coach: Why it’s never been easier to start a company, and never been harder to scale one | Brian Halligan (co-founder, HubSpot) · Brian Halligan
“The one person billion dollar startup implies that to enable it, there might be a hundred other small startups building bespoke software. We might actually enter into a golden age of B2B SaaS.”
Sherwin Wu V2 · Sherwin Wu V2
“The models will eat your scaffolding for breakfast. Build for where the models are going, not where they are today.”
Sherwin Wu V2 · Sherwin Wu V2
“Every startup that I've seen fizzle out is not because OpenAI or a big lab has come and squashed them. It's because they built something that didn't resonate with customers.”
Sherwin Wu V2 · Sherwin Wu V2
“There has to be a deeper truth to it. There's a serious real narrative to why etiquette matters in 2025 for founders.”
How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · Sam Lessin
“Etiquette is a skill for how to show up in a room with a low heart rate. You kind of want to show up with the self-confidence and the calm of abundance.”
How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · Sam Lessin
“Coming in and saying 'Hey let me give you my four-minute startup spiel' is so self-centered. Think of it like ping pong — hit the ball back.”
How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · Sam Lessin
“Seed VCs who invest in companies branded as AI companies are going to lose an impossibly large amount of money. There's a difference between a great business using AI versus an 'AI company.'”
How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · Sam Lessin
“However you get those first 10, 15, 20 customers, be honest. If they need a sales type motion and you say 'I don't like sales, so I'm going to do a PLG motion,' you'll fail.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“Almost all founders are A+ middlers. Any founder should be there by day one. And prospects love it — they get to talk to you. It's magical for early adopters.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“Those first couple reps have to be people you would buy your own product from. We're looking for pirates and romantics in the early days.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“You need two sales reps hitting quota before you're ready to hire a manager for them. If you hire a VP of sales before then, it's approaching 100% chance of failure.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“Trust me, hire someone whose last product was harder to sell. If you hire someone from something easier, they will have none of the skills.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“Product market fit is a sort of thing where you absolutely know it when you see it. The Silicon Valley 'never quit' mindset is not pro-entrepreneur, it's pro-venture capitalist.”
10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · Matt MacInnis
“The market is immutable. No amount of tweeting, advertising is going to change whether the market wants your product.”
10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · Matt MacInnis
“Point solutions don't have enough data in the age of AI to be useful. If you own the mine with the data, you can make money.”
10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · Matt MacInnis
“The purest form of ambition and most intense source of energy in the business is the founder CEO. Every next concentric circle of management has the potential to be an order of magnitude drop off in intensity.”
10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · Matt MacInnis
“We basically never wanted to play the Silicon Valley game. We could fire 90% of the people and we would move faster.”
The 100-person AI lab that became Anthropic and Google's secret weapon | Edwin Chen (Surge AI) · Edwin Chen
“The standard playbook is to get product market fit by pivoting every two weeks, chase growth with dark patterns, blitz scale. I've always disagreed. Just build the one thing only you could build.”
The 100-person AI lab that became Anthropic and Google's secret weapon | Edwin Chen (Surge AI) · Edwin Chen
“With AI, it's just intensified because you have 10 players pursuing the same market opportunity and so your ability to actually bring the product to market has become more strategically important.”
What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) · Jeanne Grosser
“65% of startups fail because of co-founder conflict. Just like couples need a date night, co-founders need regular check-ins.”
A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · Rachel Lockett
“Would you enthusiastically rehire this person for the same role? That's the question we always asked at Stripe.”
A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · Rachel Lockett
“The one-page plan puts your vision and values on the first column, strategic intentions and KPIs on the second, annual goals on the third, and quarterly goals on the fourth.”
A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · Rachel Lockett
“The overwhelming majority of people you hire want to hire more people who report to them because headcount correlates with career trajectory.”
Slack founder: Mental models for building products people love ft. Stewart Butterfield · Stewart Butterfield
“You're not just responsible for creating the product, but also creating the market. It's almost impossible to create a new idea in someone's head.”
Slack founder: Mental models for building products people love ft. Stewart Butterfield · Stewart Butterfield
“You have to be coldly rational about pivoting because it's humiliating. It feels better to keep doing it until it dies of suffocation.”
Slack founder: Mental models for building products people love ft. Stewart Butterfield · Stewart Butterfield
“In the middle of 2015, 2016, some tech companies avoided using the word AI because they were not sure if AI was a dirty word.”
The Godmother of AI on jobs, robots & why world models are next | Dr. Fei-Fei Li · Dr. Fei Fei Li
“A lot of early stage founders get tripped up taking late stage sales advice. The founder is the product.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“One of the worst things someone can say is 'we're better than X product.' Better is a dangerous place. You need to be different, not better.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“Founder led sales is not about revenue on day one. It is about learning as fast as humanly possible.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“40 to 50% of B2B SaaS startups have to sell some form of service before they can sell a technology.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“Trust is the number one currency in sales. Don't try to sell something just to prove to investors you sold something.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“Investors gave really helpful feedback, often in the form of rejection. I would add a new page showing how big the market was.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“The thing that I love about a crazy big goal is that you feel completely inadequate before it. You want to work really hard to will it into existence.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“Step one, build one of the world's most valuable companies. Step two, do the most good we can do. They fuel each other.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“We didn't worry about competitors at all. It's better to solve a small number of people's problem really well.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“There's many times we took bricks from someone else's house, and they didn't match. Confidence in how we take what is authentic to us and do it at the next level of scale is constant work.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“A lot of engineers think code quality is important to building a successful product. The two have nothing to do with each other. YouTube was storing videos as blobs in MySQL.”
How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna · Dhanji R. Prasanna
“There's this cult of lean, scrappy, fast. I see the opposite more often — people hold on to small teams too long and the product dies on the vine.”
Inside Google's AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search) · Robby Stein
“These things take 6 to 12 months to get truly robust. Like with any major tech revolution, headlines tell one story and on the ground, you need to dig up every road.”
First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege · Jason Droege
“From an entrepreneurship standpoint, it truly is about what insight do I have? Why am I so lucky to have this insight?”
First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege · Jason Droege
“For Google SEO, you need domain authority. For AEO, you can get mentioned by a citation tomorrow. Early-stage companies can win quickly.”
The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite) · Ethan Smith
“The worst thing you do as a leader is hesitate on the next decision. Both decisions are horrible. Choose quickly.”
$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder) · Ben Horowitz
“If you don't trust what you see and run at it, you're just not going to be good. CEOs are like great athletes.”
$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder) · Ben Horowitz
“If you were founding a new company from scratch with the same mission, how would you execute using a fully AI native approach?”
How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO) · Howie Liu
“This person has been tweeting spicy takes not substantiated by real data, yet this particular tweet went super viral.”
How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO) · Howie Liu
“We're the largest expert network in the world. The only moat in human data is access to an audience.”
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO) · Garrett Lord
“The models have gotten so good that generalists are no longer needed. We have 500,000 PhDs, 3 million master students.”
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO) · Garrett Lord
“We started to see direct outreach from the Frontier Labs trying to cut out the middleman. Five months later we were working with arguably the number one lab.”
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO) · Garrett Lord
“Separate engineering team, separate design team, separate finance team. People only had one job — making Handshake AI successful.”
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO) · Garrett Lord
“We had this motto: leave nothing to chance. There will never be a time like this. I've never seen anything like it.”
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO) · Garrett Lord
“We were about to hit $0 net new ARR, which means we would've been in negative growth territory.”
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO) · Eoghan McCabe
“I said, we need to become a wartime company. I rewrote the values designed to be a sharp knife to cut out the parts of the company that wouldn't be effective.”
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO) · Eoghan McCabe
“You don't have a choice. AI is going to disrupt in the most aggressive violent ways. If you're not in it, you're about to get kicked out.”
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO) · Eoghan McCabe
“The employee model is simple: compensation at the base, recognition in the middle, meaning at the top.”
Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA) · Chip Conley
“Culture is what happens around here when the boss is not around. The more distributed, the more culture is important.”
Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA) · Chip Conley
“We felt like safety wasn't the top priority there. The case for safety has gotten a lot more concrete.”
Benjamin Mann · Benjamin Mann
“You don't want to walk into the gym on day one and try and deadlift 300 pounds.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“The biggest mistakes I've made have been going into business models where other people have repeatedly failed.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“Charlie Munger says, 'Fish where the fish are.' Find a small fishing hole with lots of fish and very little competition.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“In order to know what problems are valuable to solve, you kind of need to have valuable problems.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“What you want is problems where the pain level is really high and the existing solutions are really bad.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“Your brand name, nothing's going to be used more often or for longer than that name. Design will change, messaging will change, products will change, but that name is there.”
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) · David Placek
“Just draw a shape of a diamond on a piece of paper. On the top put the word win. How do you define winning? On the next corner, what do you have to win? On the bottom, what do you need to win? And then on the left-hand side, what do you have to say to win?”
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) · David Placek
“Forget about the word, think about behavior and experience. I'm a big believer in synchronicity. If someone says we make sailboats, I would say forget about sailboats. Go pick out some magazines about hunting or flying. I would bet you $5 that out of those two magazines, you will get a word that you never would've thought of, but somehow it would relate to sailing.”
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) · David Placek
“The .com or URL address has become an area code. And whether you're in 415 or 615, it doesn't really matter to people. And now with AI, SEO is going to be less important. The principle in play is let's get the right name first.”
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) · David Placek
“Sometimes your product actually doesn't matter. At Uber, I learned this because, really, the price and the ETA at Uber was the product. Looking at it from a holistic perspective, we humans consume the entirety of the product. It's not to say that you shouldn't fix the bug, but it doesn't have as much of an impact as something that is more important to people.”
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng · Peter Deng
“AGI is just necessary but not sufficient. A lot of the value is still going to require a bunch of hustle from a lot of builders to really turn that new source of energy and channel it into something that we humans want to use that solves some of our problems.”
From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng · Peter Deng
“Design is trying to imagine the future you want to live in and then take the steps to make it real. Saying a company is design-led does not mean it's designer-led. I've never seen somebody graft it on after the fact. It's there at the beginning in the root DNA or it doesn't exist.”
35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley · Bob Baxley
“Being willing to build at the edge of capabilities and basically break the model and then be surprised by the next model. Those are the companies where I'm like, 'Yep, they get it.' They were trying it beforehand and then hitting a wall and being like, the models are almost good enough.”
Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram) · Mike Krieger
“We launched Stripe Relay back in 2014 for social commerce buy buttons. It launched to a lot of fanfare, but eventually failed. The learning was we hadn't gone deep enough into the market dynamics. We hadn't done enough user research on whether people really wanted this.”
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman · Krithika Shankarraman
“Strategy is a little bit overrated for product. For most product managers, your strategy should be, 'How fast can I go from hypothesis to data?'”
Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product) · Mayur Kamat
“At Binance, we had this ability to just put 500 people in and solve the problem. It's less about having the 500 people and being able to maneuver them that quickly. I don't think I've been able to do that at any other company.”
Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product) · Mayur Kamat
“There's no right or wrong decisions. There's just slow and fast decisions. If you make a wrong decision fast enough, you would know it was wrong and you would correct it faster than thinking months for the right decision.”
Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product) · Mayur Kamat
“Three inflection points for great products: technology shift, consumer behavior shift, and business model shift. At least two out of three should be true for any good product. With AI, the monetization is a whole different story -- we've just barely scratched the surface.”
Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada · Aparna Chennapragada
“It's not getting traction. Is it because the underlying idea is wrong? Or maybe your product just sucks? By forcing everyone to build a product that people will love, we kind of cut out this part of uncertainty. We will never compromise on the quality and UX and the aesthetics.”
How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product) · Dmitry Zlokazov
“If something is 99% done, it's closer to 0% rather than 100%.”
How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product) · Dmitry Zlokazov
“We started building a website that allows people to buy cinema tickets online. We built end-to-end hardware, stainless steel scanners, hacked the SMS standard to send QR codes to Nokia phones. We spent all our investment on hardware without any proven business model. We were just enjoying building a product we would love to use.”
How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product) · Dmitry Zlokazov
“If you're excited to build certain things, never hesitate to do it. The best way is probably your own startup, which will give you the steepest possible learning curve, but if you want to join a company, try to choose the one that has the highest entrepreneurial spirit and will allow you to work as close to a mode of a founder as you possibly can.”
How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product) · Dmitry Zlokazov
“When you started a new project, you basically had to organize what they called a murder board. You write up a two-page plan for the project. You invite three or four smart folks who don't know anything about the project and their job is just to tear apart your plan.”
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir) · Nabeel S. Qureshi
“As soon as we have titles, you have a thing that people are competing for and then you get these very unproductive conflicts. You get people optimizing to game the system. You get Goodhart's law everywhere.”
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir) · Nabeel S. Qureshi
“Every week, you would have a cadence where Monday you go in, do your meetings. Monday night, you build something. Tuesday, you show it to somebody. Tuesday, you get the feedback. Tuesday night, you iterate on it. You get four or five of these cycles every single week.”
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir) · Nabeel S. Qureshi
“I think it's very hard to not be anchored to your own experience and your conceptions of a problem. One thing I've seen in really strong founders is they're able to drop a bunch of those assumptions and almost treat a new opportunity as a completely blank slate.”
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir) · Nabeel S. Qureshi
“When you actually feel that difference between somebody who's just checking the boxes and somebody who's kind of an animal in this way, they'll actually go and pursue and accomplish the end outcome, that difference is very, very big and it matters so much for your first 20 people.”
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir) · Nabeel S. Qureshi
“Why is it that nobody on my team can make a decision without me? Who hired them? How can you hire people whom you expect to make decisions without running them through you if you can't tolerate them making a decision that you disagree with?”
How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC) · Jerry Colonna
“I truly just think that the ceiling is so high that no matter what entrenchment you build, you can be leapfrogged. It is incumbent on us to continue to try to build the best thing.”
The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO) · Michael Truell
“Many people you hear hired too fast, I think we actually hired too slow to begin with. Getting the right group of people into the company was the thing that maybe more than anything else, apart from building the product, we really, really fussed over.”
The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO) · Michael Truell
“We're in the middle of a technology shift that's going to be more consequential than the internet. And I think it's going to take a while, it's going to be a multi-decade thing, and many different groups will be consequential in pushing it forward.”
The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO) · Michael Truell
“We really have an approach of very radical transparency about everything. Before we went public, we actually shared every bit of information with our employees. Instead of demoralizing people, it gives them a sense of deep partnership.”
Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer) · Daniel Lereya
“We actually announced five different new products simultaneously. People said we're going to confuse our current users. But we managed to transform the company in a very short amount of time. Not taking bold risks is a risk for itself.”
Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer) · Daniel Lereya
“There were personally times when suddenly I saw how my biggest strength, like mastering all the details and having everything in my head, created damage by continuing to do the same thing. Don't be afraid to let go of things that you think are superpowers.”
Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer) · Daniel Lereya
“I want the company to almost be like this dehydrated entity. Every hire is like a little bit of water, and we only go back and hire someone when we're back to being dehydrated.”
Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO) · Varun Mohan
“You don't win by doing 10 things well. You win by doing one thing really well and maybe you fail nine things. In school you optimize for your total GPA. But for companies, I just need to get an A+ on the one class that matters.”
Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO) · Varun Mohan
“My number one guidance I would give to any startup founder is create a lot of opportunities for people to give you feedback inside the product. When you're building AI products, it's a constant stream of user feedback. For people thinking about not building AI products, it's going to be hard to compete with something that has such a tight feedback loop.”
Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder and CEO of Vercel, creators of v0 and Next.js) · Guillermo Rauch
“Our engineering goal is every engineer should ship a marketable product every week.”
How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions) · Gaurav Misra
“Every piece of debt that you take on you have to pay interest on. 1% or 2% of your time every day. If you take on enough debt, you'll be paying 80 or 90% interest and you won't have time to do anything new. You have a technical debt runway.”
How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions) · Gaurav Misra
“We have a second roadmap which we think of as a secret roadmap. Nobody has ever asked for anything on it. Given our unique vantage point, we've come up with special ideas that will completely revolutionize how something is used where we can truly change the behavior of the user.”
How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions) · Gaurav Misra
“At Captions, we're going even one step further. Why shouldn't the PM understand marketing? I actually think PMs should own all the way to marketing. Search marketing is just placing a button to your product in Google. That's almost a product surface.”
How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions) · Gaurav Misra
“You can classify anything that you build in a company into one of two categories, solution deepening and market widening. Solution deepening means making your product better for its existing users, but not making it available to more users. Whereas market widening means making your product available to more users, but not making the product itself any better.”
Superhuman's secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO) · Rahul Vohra
“The company was on the verge of going under when we launched Bolt, and what ended up happening is, in the first two months it went from zero to 20 million of ARR. And we've already crossed 30 million of ARR, with the current rate we're on, our forecast for the year is we want to get to 100 million of ARR.”
Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz) · Eric Simons
“Most importantly, it's been the people. It's rare to find startups where you have the core group of five, six, seven people that have been there for five years plus.”
Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz) · Eric Simons
“It's always good to just have the perspective of, you should start companies to keep the mindset that you're doing it to have fun. So, stoked to see where this goes, one way or the other. It's going to be interesting.”
Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz) · Eric Simons
“Lovable is your personal AI software engineer. You describe an idea and then you get a fully working product. The reason is to enable those who have had such a hard time finding people who are good at creating software that's been their absolute bottleneck and let them take their ideas and their dreams into reality.”
Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO) · Anton Osika
“The best word for a great product is that it's lovable. A lot of jargon that I like to use to emphasize what we should be striving for is building a minimum lovable product and then building a lovable product and then building an absolutely lovable product. So I took that jargon with me in the company name.”
Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO) · Anton Osika
“The big learning is that you have to start with how is this product working end-to-end and then add AI or think where should we add AI. You really want to see what does the big picture of the user experience look like, and then add something with AI to solve specific problems.”
Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (co-founder and CEO) · Anton Osika
“We called it sugar-coated broccoli. People don't want to eat the broccoli but people like sugar, so it gave them the sugar then hide your broccoli inside of it.”
Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder) · Ivan Zhao
“I think one element is we have to be very honest about what we don't know and we don't know users. It took us two years to realize we need to build a productivity tool.”
Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder) · Ivan Zhao
“We were 10 people when COVID hit. We nearly ran out of database space. We had to scramble. That near-collapse was actually the moment that forced us to get serious about infrastructure.”
Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder) · Ivan Zhao
“Staying small is a feature, not a bug. When you're small, you can move fast. Every person you add is a communication overhead. We stayed at about 50 people for a very long time intentionally.”
Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder) · Ivan Zhao
“WordPress.org is the open source project, WordPress.com is our hosted service, and WP Engine is a company that makes a ton of money from WordPress and gives almost nothing back. They're strip-mining the commons.”
The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic) · Matt Mullenweg
“Tumblr had these multiple post types. You could post a chat, an image. They were one of the first to support video, so they did a lot of product innovation under the leadership of David Karp.”
The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic) · Matt Mullenweg
“We bought Tumblr for $3 million. But it was free like a puppy, not free like beer. We took on all liabilities, including FTC investigations and lawsuits.”
The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic) · Matt Mullenweg
“What is your energy source? My energy source is dissatisfaction with status quo. I think today is the dystopia of the future. It behooves us to try to build the kinds of products that leads towards progress.”
Tobi Lutke · Tobi Lutke
“If most people are doing it a certain way, I by default don't want to do it that way. That's not contrarianism for its own sake, it's just that the default path is usually optimized for average outcomes.”
Tobi Lutke · Tobi Lutke
“For the first several years, it was doubling, 10-xing every year. Taping user counts that we printed out to the wall, and then running out of space on the wall.”
Behind the founder: Drew Houston (Dropbox) · Drew Houston
“We started getting all the incumbents. Apple, Microsoft, Google. All of them launched competing products, but weirdly, it was sort of like you see the videos where there's the mushroom cloud in the distance. You see it. But you don't hear, or notice it.”
Behind the founder: Drew Houston (Dropbox) · Drew Houston
“2015 was a pivotal year where things started to shift. It was clear that winter was coming. We had to completely rethink who we were and what we were building for.”
Behind the founder: Drew Houston (Dropbox) · Drew Houston
“The biggest lesson from that era is you have to be willing to cannibalize yourself. If you're not willing to disrupt your own product, someone else will do it for you.”
Behind the founder: Drew Houston (Dropbox) · Drew Houston
“I'm throwing everything against the wall. I'm looking at what's going to stick. I am looking to try to find the winning tactic and turn it into a winning strategy.”
Behind the founder: Marc Benioff · Marc Benioff
“I actually never look at the stock. I find the stock to be very distracting. The stock isn't the goal. That's not why we're doing this.”
Behind the founder: Marc Benioff · Marc Benioff
“To be a founder is a state of being, it's an attitude. To be a CEO is a craft. The more founders who can accept that those are two separate things and they're both equally important to build an ascendant startup, the better all of us will be.”
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · Jonathan Lowenhar
“Founder mode gets me angry. That article just got me hot. It really felt like an excuse. We were giving founders permission to not learn the job.”
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · Jonathan Lowenhar
“There are these two phases to a startup journey. Phase one is finding product-market fit. Phase two is building the company. Most founders focus entirely on phase one and never learn how to do phase two.”
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · Jonathan Lowenhar
“The greatest CEOs know when to calibrate which one is needed. It's not manager mode is bad, it's that you need both modes and you need to know when to deploy each.”
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · Jonathan Lowenhar
“The founders who scale are the ones who realize that their job description changes every six months. What got you here won't get you there, and that's not a failure, it's the nature of the journey.”
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · Jonathan Lowenhar
“The idea behind Replit is that making software today is very difficult. We want to make it easier. People view this as a developer in their pocket essentially. We have 34 million users globally.”
Behind the product: Replit | Amjad Masad (co-founder and CEO) · Amjad Masad
“I could imagine whatever five years from now, someone running a billion-dollar company with zero employees where it's like the support is handled by AI, the development is handled by AI, and you're just building and creating this thing.”
Behind the product: Replit | Amjad Masad (co-founder and CEO) · Amjad Masad
“I was hired as the first product manager. I sat in on those calls. I still did not exactly understand what we were going to build, which was confusing. And that ended up pivoting us around to cloud security.”
Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy) · Raaz Herzberg
“We would have 10 to 15 meetings every day with potential customers. At the time, we didn't really have a solid product yet.”
Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy) · Raaz Herzberg
“We went from zero to $100 million ARR faster than any SaaS company in history. But it wasn't luck. It was the combination of a team that had built and sold a company together before, and a market that was screaming for a solution.”
Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy) · Raaz Herzberg
“So much of the way that we tackle problems and build products is this builder mindset. Part of the problem though is it can't possibly create more value than the effort that you put into it. What I look for instead are things that can be gardened, things that can grow on their own and that you can direct or maybe give a little bit of extra energy to or curate over.”
Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google) · Alex Komoroske
“We've forgotten a world without aggregators. Aggregators make sense in the late stage of an era. At the beginning, they curtail too much exploration.”
Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google) · Alex Komoroske
“Software is alchemy. It's the ability to extend human agency beyond ourselves to create something that can then combine with what others have created in unexpected and unforeseen ways. And somehow in the past decade, we've become convinced that all of this potential should be squeezed into about a dozen little boxes on your phone.”
Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google) · Alex Komoroske
“I'm a huge believer in market forces and empowerment, so provide guardrails for what a good experience is in your marketplace, set a clear bar for quality, and provide the right coaching and tools for supply to be successful, and then take a step back and see where the gaps are.”
How marketplaces win: Liquidity, growth levers, quality, and more | Benjamin Lauzier (Lyft, Thumbtack, Reforge) · Benjamin Lauzier
“Before the referral program, Dropbox had amazing referral rate. Companies that are trying to copy it are like, 'Why isn't anyone talking about a product? Let's add a referral program with incentives.' To me, I think it's a great accelerant when it's already working, but it can't fix it if people don't want to talk about your product.”
The original growth hacker reveals his secrets | Sean Ellis (author of “Hacking Growth”) · Sean Ellis
“I looked on the App Store and the number one app in the United States was an app called Surah, but the entire app was in Arabic, like the strongest signal that you could ever have that people want something.”
How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor) · Nikita Bier
“We launched this app, it immediately took off, servers started crashing. I looked at our numbers and I'm like, 'We will be number one in the United States in six days.'”
How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor) · Nikita Bier
“Honored to be on a product management podcast for a person who doesn't believe product management is real.”
How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor) · Nikita Bier
“If mission, vision, values was an airline, you would not allow any family to fly on that airline. It does not arrive at most of its intended destinations.”
Improve strategy, influence, and decision-making by understanding your brain | Evan LaPointe (founder of CORE Sciences) · Evan LaPointe
“Uber always has this mentality and Opendoor does two of the product operations, twin turbine jet plane where you can fly the plane on one engine for a little bit if you need to, but it's operating most efficiently and effectively if both are working together.”
Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · Brian Tolkin
“Gave a really deep understanding of how the business actually works. It's a pretty good foundation for then going on to say, okay, what do we actually want to build in a more scalable technology way.”
Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · Brian Tolkin
“You have to be either differentiated or low cost, there's no way to protect yourself if you're not one of those two.”
5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker) · Roger Martin
“I find proof of existence to be an incredibly powerful proof, rather than proof by theory or proof by debate. It's like, 'Look, we did it one time.'”
Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead) · Jeff Weinstein
“The three are inflections, insights and then the founder future fit. Business is never a fair fight. What inflections let the founder do is wage asymmetric warfare on the present.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“The way inventions happen is people get their hands dirty, being awake to the possibility that secrets are there. If you're living in the future and you notice what's missing, your intuition about what to build is far more likely to be right.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“The number one thing that I've learned is that you have to be willing to have your idea change, but you can't lose touch with the insight. 80% of our biggest returning investments came from a pivot.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“A startup never beats a big company by executing better than the big company. Startup wins over the big company because it proposes a radically different future, disorients the incumbent, and sort of chaotically moves people to that different future.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“The mistake that most companies make is they say, 'I've got this new pattern-breaking idea. It needs to be a third of my business in 24 months.' Bad strategy... Pattern-breaking products have different types of leadership, different types of go-to-market motion, different risk profiles.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“It's a lonely existence, and it's okay if most people don't like your idea. It doesn't mean you're right, but it sure as heck doesn't mean you're wrong either. There's not enough people in this world willing to stick their neck out for things that they believe that they see before the rest of us.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“In the early days of Figma, everyone told us the browser would never be fast enough. We just kept pushing. Sometimes you have to have conviction in a technical bet that everyone else thinks is wrong.”
Dylan Field live at Config: Intuition, simplicity, and the future of design · Dylan Field
“My three co-founders were deeply technical, but I would look at other things about founders. All these little social cues.”
The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host) · Jessica Livingston
“I would look at, do the co-founders get along? Are these people committed? And if a founder would get defensive, that was always a bad sign.”
The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host) · Jessica Livingston
“He hated their idea, and Paul tried to get Brian and Joe and Nate to change it. But I remember specifically Joe brought out the cereal boxes, the Obama O's and Cap'n McCain's, and I just thought, oh my God, they're going to work hard to do whatever they can to make this company succeed.”
The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host) · Jessica Livingston
“The most important thing we did at YC was create an environment where founders could be honest about their problems. Most founders are performing for investors and the outside world. At YC dinners, they could let their guard down.”
The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host) · Jessica Livingston
“One of the things I noticed is that the founders who struggled the most were the ones who were not resilient. It wasn't about the idea. It was about whether they could take a punch and keep going.”
The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host) · Jessica Livingston
“The company has a tendency to over-invest. Startups have the benefit of starving, and so you need to create scarcity. What we try to do is remind everyone things are going to fail, let's not drag the rest of the company into it.”
Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery) · Tanguy Crusson
“I needed the rest of the company to go away so we could get the autonomy to test the things that we needed, but it's not going to scale. That is not going to respect all design guidelines.”
Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery) · Tanguy Crusson
“This concept of incubate by working on something on the side, iterate until you've got it right and then integrate it back into the main product is something I would definitely do again.”
Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery) · Tanguy Crusson
“Fall in love, fall in love, fall in love, fall in love with the problem, and then actually what you're trying to do is engage everyone else to fall in love with the same problem, to go into this journey, into this path and follow your leadership there.”
Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze) · Uri Levine
“Most people are missing the most important slide of their presentation is the first slide. This slide is going to be presented for the longest period of time. This is the place that you're going to put your strongest point.”
Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze) · Uri Levine
“The value is not about what the product does. The value is about the problem you solve. If you can describe the problem in a way that the person you're talking to says, 'oh my God, I have that problem,' you've won.”
Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze) · Uri Levine
“Product-market fit is a journey, not a destination. With Waze, we changed the product significantly three or four times before we got it right. The first version, nobody used. The second version, a few people used. The third version, people started using and telling their friends.”
Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze) · Uri Levine
“We've been profitable from very early on. That changes everything about how you make decisions. You're not on someone else's timeline. You're on your own timeline.”
Inside Canva: Coaches not managers, giving away your Legos, and running profitably | Cameron Adams (co-founder and CPO) · Cam Adams
“For me, the impact was about making this work sustainable so that we're not burning out or selling out, but actually able to pursue these hard goals that we have in startups.”
Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM at Slack) · Kenneth Berger
“We're not trying to be incrementally better, we are trying to be fundamentally different. We want our customers to love us fanatically.”
Be fundamentally different, not incrementally better | Jag Duggal (Nubank, Facebook, Google, Quantcast) · Jag Duggal
“Power requires a benefit and a barrier, so he's taking care of the benefit part by saying a castle, you have to have a pretty good understanding of why it's a castle and not a shack.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“You're on a treadmill and if you stop running on that treadmill, you get creamed, but it's not power. The things that drive operational excellence can be mimicked.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“There's a thing called power progression. There are times when certain types of power are available. The path to power is where the rubber meets the road.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“Network effects are the most powerful of the seven powers. If you have a product where every incremental user makes the product more valuable for every other user, that's an extraordinarily durable position.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“Counter-positioning is when a newcomer adopts a new, superior business model that the incumbent can't adopt because it would damage their existing business. This is what Netflix did to Blockbuster.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“The most important thing about quitting is to set your criteria in advance. Decide when you will quit before you start. Once you're in it, your sunk cost bias will keep you going way too long.”
This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player) · Annie Duke
“Live video taught me that you can build a product that people don't ask for and they don't know they want, and it can become something they can't live without. Periscope was that for me.”
Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more | Kayvon Beykpour · Kayvon Beykpour
“One of my mantras is just don't die. Being coached and being reminded of the fundamentals and basics puts you in the right mindset.”
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · Dalton Caldwell
“Seems like an unsolved problem. You'll get all this positive feedback from the world and people have been starting that startup since the '90s.”
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · Dalton Caldwell
“A good pivot is like going home. It's warmer, it's closer to something that you're an expert at.”
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · Dalton Caldwell
“We're trying to mix up some of the information diet about what kind of ideas people might be contemplating they are currently.”
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · Dalton Caldwell
“The founders who do best at YC are the ones who are resilient. They take the feedback, they iterate quickly, and they don't get emotionally attached to any single version of the product. They're attached to the problem.”
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · Dalton Caldwell
“Finding product-market fit is the single most important thing that your startup does in the first three years, and it's just underexplored and it's just underexplained as a topic.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“We've published dozens of articles on the First Round Review, and we have found a very consistent set of patterns, demand satisfaction, and efficiency. But the interesting thing is that you don't go for all three of them from the very beginning.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“You've got the persona, the problem, the promise, and the product. Lattice kept the first one but changed the others. Vanta changed all four.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“Roughly, 60% are never going to get past L2.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“The best signal that you have nascent product-market fit is when customers start pulling the product from you. You don't have to push it anymore. They're asking you for it. That's a qualitative signal that data won't show you.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“At the developing stage, the biggest mistake I see is premature scaling. You have a few happy customers and you think you should hire a sales team and start marketing. But you haven't really nailed what makes those customers happy.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“People often think that I get hired into later stage companies because I'm supposed to teach them how to operate like a big company, and in fact, I say I'm hired to remind them they can operate like a startup.”
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD) · Claire Vo
“In the early days of Gojek, there was a lot of resistance to our services. The most common form of that resistance was actually by motorcycle taxi mafia. These people would actually physically assault our drivers. We've had everything from bricks thrown at our drivers to knives and machetes being brandished at them. But instead of saying they're all contractors, let them sort it out, we actually hired private security to help extract them out of these sticky situations.”
Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek) · Kevin Aluwi
“I really don't like the idea of moats. I don't believe that any moats are durable over time. Eventually with enough time all moats can be crossed. One so-called moat that doesn't get talked about enough is the fact that you're able to do hard things because hard things are hard, and just simply doing things that are hard, as long as they create value to your customers, actually makes it harder for your competitors to win.”
Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek) · Kevin Aluwi
“Every business that you have heard of has gotten rejected by at least a handful of venture capitalists at one point or another. We were weeks of runway situation and had been told no by everyone. And it was just Tony's drive to keep going. The way he explains it is it's just the difference between a founder and a non-founder. If you're really a founder, you just have to find a way. It only takes one yes. But you got to keep going.”
Leading with empathy | Keith Yandell (DoorDash, Uber) · Keith Yandell
“The thing that I just like to encourage founders and product managers is just don't be afraid of sales. There's a lot of people out there who would love to tell you a story that it's magical or like, 'Oh, you've got to be a born seller,' and it's really not. Those people are just talking their book. Just getting good at those behaviors, it's going to benefit you in a myriad of ways.”
Founder-led sales | Pete Kazanjy (Founding Sales, Atrium) · Pete Kazanjy
Cutting Room Floor
Guest insights on this topic that Lenny hasn't (yet) written about in his newsletters. Potential material for future posts.
“You have to know the difference between a megatrend and a hype cycle. When there's a megatrend, don't fight it. AI is a megatrend, one of the most foundational movements that we have seen in human history.”
Jeetu Patel · Jeetu Patel
“The one person billion dollar startup implies that to enable it, there might be a hundred other small startups building bespoke software. We might actually enter into a golden age of B2B SaaS.”
Sherwin Wu V2 · Sherwin Wu V2
“There has to be a deeper truth to it. There's a serious real narrative to why etiquette matters in 2025 for founders.”
How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · Sam Lessin
“Coming in and saying 'Hey let me give you my four-minute startup spiel' is so self-centered. Think of it like ping pong — hit the ball back.”
How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · Sam Lessin
“Seed VCs who invest in companies branded as AI companies are going to lose an impossibly large amount of money. There's a difference between a great business using AI versus an 'AI company.'”
How to show up in any room with a low heart rate: Silicon Valley’s missing etiquette playbook | Sam Lessin · Sam Lessin
“Those first couple reps have to be people you would buy your own product from. We're looking for pirates and romantics in the early days.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“Trust me, hire someone whose last product was harder to sell. If you hire someone from something easier, they will have none of the skills.”
We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) · Jason M Lemkin
“The purest form of ambition and most intense source of energy in the business is the founder CEO. Every next concentric circle of management has the potential to be an order of magnitude drop off in intensity.”
10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) · Matt MacInnis
“65% of startups fail because of co-founder conflict. Just like couples need a date night, co-founders need regular check-ins.”
A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · Rachel Lockett
“Would you enthusiastically rehire this person for the same role? That's the question we always asked at Stripe.”
A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett · Rachel Lockett
“The overwhelming majority of people you hire want to hire more people who report to them because headcount correlates with career trajectory.”
Slack founder: Mental models for building products people love ft. Stewart Butterfield · Stewart Butterfield
“You have to be coldly rational about pivoting because it's humiliating. It feels better to keep doing it until it dies of suffocation.”
Slack founder: Mental models for building products people love ft. Stewart Butterfield · Stewart Butterfield
“In the middle of 2015, 2016, some tech companies avoided using the word AI because they were not sure if AI was a dirty word.”
The Godmother of AI on jobs, robots & why world models are next | Dr. Fei-Fei Li · Dr. Fei Fei Li
“One of the worst things someone can say is 'we're better than X product.' Better is a dangerous place. You need to be different, not better.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“Trust is the number one currency in sales. Don't try to sell something just to prove to investors you sold something.”
"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel · Jen Abel
“Investors gave really helpful feedback, often in the form of rejection. I would add a new page showing how big the market was.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“The thing that I love about a crazy big goal is that you feel completely inadequate before it. You want to work really hard to will it into existence.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“Step one, build one of the world's most valuable companies. Step two, do the most good we can do. They fuel each other.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“There's many times we took bricks from someone else's house, and they didn't match. Confidence in how we take what is authentic to us and do it at the next level of scale is constant work.”
The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins · Melanie Perkins
“There's this cult of lean, scrappy, fast. I see the opposite more often — people hold on to small teams too long and the product dies on the vine.”
Inside Google's AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search) · Robby Stein
“These things take 6 to 12 months to get truly robust. Like with any major tech revolution, headlines tell one story and on the ground, you need to dig up every road.”
First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege · Jason Droege
“From an entrepreneurship standpoint, it truly is about what insight do I have? Why am I so lucky to have this insight?”
First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege · Jason Droege
“The worst thing you do as a leader is hesitate on the next decision. Both decisions are horrible. Choose quickly.”
$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder) · Ben Horowitz
“If you don't trust what you see and run at it, you're just not going to be good. CEOs are like great athletes.”
$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder) · Ben Horowitz
“If you were founding a new company from scratch with the same mission, how would you execute using a fully AI native approach?”
How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO) · Howie Liu
“This person has been tweeting spicy takes not substantiated by real data, yet this particular tweet went super viral.”
How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO) · Howie Liu
“We're the largest expert network in the world. The only moat in human data is access to an audience.”
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO) · Garrett Lord
“The models have gotten so good that generalists are no longer needed. We have 500,000 PhDs, 3 million master students.”
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO) · Garrett Lord
“We had this motto: leave nothing to chance. There will never be a time like this. I've never seen anything like it.”
Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO) · Garrett Lord
“I said, we need to become a wartime company. I rewrote the values designed to be a sharp knife to cut out the parts of the company that wouldn't be effective.”
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO) · Eoghan McCabe
“You don't have a choice. AI is going to disrupt in the most aggressive violent ways. If you're not in it, you're about to get kicked out.”
How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO) · Eoghan McCabe
“The employee model is simple: compensation at the base, recognition in the middle, meaning at the top.”
Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA) · Chip Conley
“Culture is what happens around here when the boss is not around. The more distributed, the more culture is important.”
Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA) · Chip Conley
“We felt like safety wasn't the top priority there. The case for safety has gotten a lot more concrete.”
Benjamin Mann · Benjamin Mann
“You don't want to walk into the gym on day one and try and deadlift 300 pounds.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“The biggest mistakes I've made have been going into business models where other people have repeatedly failed.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“Charlie Munger says, 'Fish where the fish are.' Find a small fishing hole with lots of fish and very little competition.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“In order to know what problems are valuable to solve, you kind of need to have valuable problems.”
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) · Andrew Wilkinson
“Just draw a shape of a diamond on a piece of paper. On the top put the word win. How do you define winning? On the next corner, what do you have to win? On the bottom, what do you need to win? And then on the left-hand side, what do you have to say to win?”
Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) · David Placek
“We launched Stripe Relay back in 2014 for social commerce buy buttons. It launched to a lot of fanfare, but eventually failed. The learning was we hadn't gone deep enough into the market dynamics. We hadn't done enough user research on whether people really wanted this.”
Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman · Krithika Shankarraman
“Strategy is a little bit overrated for product. For most product managers, your strategy should be, 'How fast can I go from hypothesis to data?'”
Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product) · Mayur Kamat
“At Binance, we had this ability to just put 500 people in and solve the problem. It's less about having the 500 people and being able to maneuver them that quickly. I don't think I've been able to do that at any other company.”
Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product) · Mayur Kamat
“Three inflection points for great products: technology shift, consumer behavior shift, and business model shift. At least two out of three should be true for any good product. With AI, the monetization is a whole different story -- we've just barely scratched the surface.”
Microsoft CPO: If you aren’t prototyping with AI, you’re doing it wrong | Aparna Chennapragada · Aparna Chennapragada
“If something is 99% done, it's closer to 0% rather than 100%.”
How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product) · Dmitry Zlokazov
“When you started a new project, you basically had to organize what they called a murder board. You write up a two-page plan for the project. You invite three or four smart folks who don't know anything about the project and their job is just to tear apart your plan.”
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir) · Nabeel S. Qureshi
“As soon as we have titles, you have a thing that people are competing for and then you get these very unproductive conflicts. You get people optimizing to game the system. You get Goodhart's law everywhere.”
How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir) · Nabeel S. Qureshi
“I truly just think that the ceiling is so high that no matter what entrenchment you build, you can be leapfrogged. It is incumbent on us to continue to try to build the best thing.”
The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO) · Michael Truell
“We're in the middle of a technology shift that's going to be more consequential than the internet. And I think it's going to take a while, it's going to be a multi-decade thing, and many different groups will be consequential in pushing it forward.”
The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO) · Michael Truell
“We actually announced five different new products simultaneously. People said we're going to confuse our current users. But we managed to transform the company in a very short amount of time. Not taking bold risks is a risk for itself.”
Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer) · Daniel Lereya
“You don't win by doing 10 things well. You win by doing one thing really well and maybe you fail nine things. In school you optimize for your total GPA. But for companies, I just need to get an A+ on the one class that matters.”
Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder and CEO) · Varun Mohan
“Every piece of debt that you take on you have to pay interest on. 1% or 2% of your time every day. If you take on enough debt, you'll be paying 80 or 90% interest and you won't have time to do anything new. You have a technical debt runway.”
How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions) · Gaurav Misra
“At Captions, we're going even one step further. Why shouldn't the PM understand marketing? I actually think PMs should own all the way to marketing. Search marketing is just placing a button to your product in Google. That's almost a product surface.”
How to win in the AI era: Ship a feature every week, embrace technical debt, ruthlessly cut scope, and create magic your competitors can't copy | Gaurav Misra (CEO and co-founder of Captions) · Gaurav Misra
“Most importantly, it's been the people. It's rare to find startups where you have the core group of five, six, seven people that have been there for five years plus.”
Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz) · Eric Simons
“We called it sugar-coated broccoli. People don't want to eat the broccoli but people like sugar, so it gave them the sugar then hide your broccoli inside of it.”
Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder) · Ivan Zhao
“I think one element is we have to be very honest about what we don't know and we don't know users. It took us two years to realize we need to build a productivity tool.”
Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder) · Ivan Zhao
“We were 10 people when COVID hit. We nearly ran out of database space. We had to scramble. That near-collapse was actually the moment that forced us to get serious about infrastructure.”
Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder) · Ivan Zhao
“Staying small is a feature, not a bug. When you're small, you can move fast. Every person you add is a communication overhead. We stayed at about 50 people for a very long time intentionally.”
Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder) · Ivan Zhao
“WordPress.org is the open source project, WordPress.com is our hosted service, and WP Engine is a company that makes a ton of money from WordPress and gives almost nothing back. They're strip-mining the commons.”
The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic) · Matt Mullenweg
“Tumblr had these multiple post types. You could post a chat, an image. They were one of the first to support video, so they did a lot of product innovation under the leadership of David Karp.”
The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic) · Matt Mullenweg
“We bought Tumblr for $3 million. But it was free like a puppy, not free like beer. We took on all liabilities, including FTC investigations and lawsuits.”
The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic) · Matt Mullenweg
“What is your energy source? My energy source is dissatisfaction with status quo. I think today is the dystopia of the future. It behooves us to try to build the kinds of products that leads towards progress.”
Tobi Lutke · Tobi Lutke
“If most people are doing it a certain way, I by default don't want to do it that way. That's not contrarianism for its own sake, it's just that the default path is usually optimized for average outcomes.”
Tobi Lutke · Tobi Lutke
“We started getting all the incumbents. Apple, Microsoft, Google. All of them launched competing products, but weirdly, it was sort of like you see the videos where there's the mushroom cloud in the distance. You see it. But you don't hear, or notice it.”
Behind the founder: Drew Houston (Dropbox) · Drew Houston
“2015 was a pivotal year where things started to shift. It was clear that winter was coming. We had to completely rethink who we were and what we were building for.”
Behind the founder: Drew Houston (Dropbox) · Drew Houston
“The biggest lesson from that era is you have to be willing to cannibalize yourself. If you're not willing to disrupt your own product, someone else will do it for you.”
Behind the founder: Drew Houston (Dropbox) · Drew Houston
“I'm throwing everything against the wall. I'm looking at what's going to stick. I am looking to try to find the winning tactic and turn it into a winning strategy.”
Behind the founder: Marc Benioff · Marc Benioff
“I actually never look at the stock. I find the stock to be very distracting. The stock isn't the goal. That's not why we're doing this.”
Behind the founder: Marc Benioff · Marc Benioff
“To be a founder is a state of being, it's an attitude. To be a CEO is a craft. The more founders who can accept that those are two separate things and they're both equally important to build an ascendant startup, the better all of us will be.”
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · Jonathan Lowenhar
“Founder mode gets me angry. That article just got me hot. It really felt like an excuse. We were giving founders permission to not learn the job.”
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · Jonathan Lowenhar
“There are these two phases to a startup journey. Phase one is finding product-market fit. Phase two is building the company. Most founders focus entirely on phase one and never learn how to do phase two.”
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · Jonathan Lowenhar
“The greatest CEOs know when to calibrate which one is needed. It's not manager mode is bad, it's that you need both modes and you need to know when to deploy each.”
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · Jonathan Lowenhar
“The founders who scale are the ones who realize that their job description changes every six months. What got you here won't get you there, and that's not a failure, it's the nature of the journey.”
How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work) · Jonathan Lowenhar
“The idea behind Replit is that making software today is very difficult. We want to make it easier. People view this as a developer in their pocket essentially. We have 34 million users globally.”
Behind the product: Replit | Amjad Masad (co-founder and CEO) · Amjad Masad
“I could imagine whatever five years from now, someone running a billion-dollar company with zero employees where it's like the support is handled by AI, the development is handled by AI, and you're just building and creating this thing.”
Behind the product: Replit | Amjad Masad (co-founder and CEO) · Amjad Masad
“I was hired as the first product manager. I sat in on those calls. I still did not exactly understand what we were going to build, which was confusing. And that ended up pivoting us around to cloud security.”
Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy) · Raaz Herzberg
“We would have 10 to 15 meetings every day with potential customers. At the time, we didn't really have a solid product yet.”
Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy) · Raaz Herzberg
“We've forgotten a world without aggregators. Aggregators make sense in the late stage of an era. At the beginning, they curtail too much exploration.”
Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google) · Alex Komoroske
“Software is alchemy. It's the ability to extend human agency beyond ourselves to create something that can then combine with what others have created in unexpected and unforeseen ways. And somehow in the past decade, we've become convinced that all of this potential should be squeezed into about a dozen little boxes on your phone.”
Thinking like a gardener not a builder, organizing teams like slime mold, the adjacent possible, and other unconventional product advice | Alex Komoroske (Stripe, Google) · Alex Komoroske
“I'm a huge believer in market forces and empowerment, so provide guardrails for what a good experience is in your marketplace, set a clear bar for quality, and provide the right coaching and tools for supply to be successful, and then take a step back and see where the gaps are.”
How marketplaces win: Liquidity, growth levers, quality, and more | Benjamin Lauzier (Lyft, Thumbtack, Reforge) · Benjamin Lauzier
“Before the referral program, Dropbox had amazing referral rate. Companies that are trying to copy it are like, 'Why isn't anyone talking about a product? Let's add a referral program with incentives.' To me, I think it's a great accelerant when it's already working, but it can't fix it if people don't want to talk about your product.”
The original growth hacker reveals his secrets | Sean Ellis (author of “Hacking Growth”) · Sean Ellis
“I looked on the App Store and the number one app in the United States was an app called Surah, but the entire app was in Arabic, like the strongest signal that you could ever have that people want something.”
How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor) · Nikita Bier
“We launched this app, it immediately took off, servers started crashing. I looked at our numbers and I'm like, 'We will be number one in the United States in six days.'”
How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor) · Nikita Bier
“Honored to be on a product management podcast for a person who doesn't believe product management is real.”
How to consistently go viral: Nikita Bier’s playbook for winning at consumer apps (co-founder of TBH, Gas, advisor, investor) · Nikita Bier
“If mission, vision, values was an airline, you would not allow any family to fly on that airline. It does not arrive at most of its intended destinations.”
Improve strategy, influence, and decision-making by understanding your brain | Evan LaPointe (founder of CORE Sciences) · Evan LaPointe
“Uber always has this mentality and Opendoor does two of the product operations, twin turbine jet plane where you can fly the plane on one engine for a little bit if you need to, but it's operating most efficiently and effectively if both are working together.”
Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · Brian Tolkin
“Gave a really deep understanding of how the business actually works. It's a pretty good foundation for then going on to say, okay, what do we actually want to build in a more scalable technology way.”
Lessons from scaling Uber and Opendoor | Brian Tolkin (Head of Product at Opendoor, ex-Uber) · Brian Tolkin
“You have to be either differentiated or low cost, there's no way to protect yourself if you're not one of those two.”
5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker) · Roger Martin
“I find proof of existence to be an incredibly powerful proof, rather than proof by theory or proof by debate. It's like, 'Look, we did it one time.'”
Building product at Stripe: craft, metrics, and customer obsession | Jeff Weinstein (Product lead) · Jeff Weinstein
“The three are inflections, insights and then the founder future fit. Business is never a fair fight. What inflections let the founder do is wage asymmetric warfare on the present.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“The way inventions happen is people get their hands dirty, being awake to the possibility that secrets are there. If you're living in the future and you notice what's missing, your intuition about what to build is far more likely to be right.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“The number one thing that I've learned is that you have to be willing to have your idea change, but you can't lose touch with the insight. 80% of our biggest returning investments came from a pivot.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“A startup never beats a big company by executing better than the big company. Startup wins over the big company because it proposes a radically different future, disorients the incumbent, and sort of chaotically moves people to that different future.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“The mistake that most companies make is they say, 'I've got this new pattern-breaking idea. It needs to be a third of my business in 24 months.' Bad strategy... Pattern-breaking products have different types of leadership, different types of go-to-market motion, different risk profiles.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“It's a lonely existence, and it's okay if most people don't like your idea. It doesn't mean you're right, but it sure as heck doesn't mean you're wrong either. There's not enough people in this world willing to stick their neck out for things that they believe that they see before the rest of us.”
Pattern Breakers: How to find a breakthrough startup idea | Mike Maples, Jr. (Founding Partner at Floodgate, ex-Product at Silicon Graphics) · Mike Maples Jr
“In the early days of Figma, everyone told us the browser would never be fast enough. We just kept pushing. Sometimes you have to have conviction in a technical bet that everyone else thinks is wrong.”
Dylan Field live at Config: Intuition, simplicity, and the future of design · Dylan Field
“My three co-founders were deeply technical, but I would look at other things about founders. All these little social cues.”
The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host) · Jessica Livingston
“He hated their idea, and Paul tried to get Brian and Joe and Nate to change it. But I remember specifically Joe brought out the cereal boxes, the Obama O's and Cap'n McCain's, and I just thought, oh my God, they're going to work hard to do whatever they can to make this company succeed.”
The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host) · Jessica Livingston
“The most important thing we did at YC was create an environment where founders could be honest about their problems. Most founders are performing for investors and the outside world. At YC dinners, they could let their guard down.”
The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host) · Jessica Livingston
“One of the things I noticed is that the founders who struggled the most were the ones who were not resilient. It wasn't about the idea. It was about whether they could take a punch and keep going.”
The social radar: Y Combinator’s secret weapon | Jessica Livingston (co-founder of Y Combinator, author, podcast host) · Jessica Livingston
“The company has a tendency to over-invest. Startups have the benefit of starving, and so you need to create scarcity. What we try to do is remind everyone things are going to fail, let's not drag the rest of the company into it.”
Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery) · Tanguy Crusson
“I needed the rest of the company to go away so we could get the autonomy to test the things that we needed, but it's not going to scale. That is not going to respect all design guidelines.”
Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery) · Tanguy Crusson
“This concept of incubate by working on something on the side, iterate until you've got it right and then integrate it back into the main product is something I would definitely do again.”
Hard-won lessons building 0 to 1 inside Atlassian | Tanguy Crusson (Head of Jira Product Discovery) · Tanguy Crusson
“Most people are missing the most important slide of their presentation is the first slide. This slide is going to be presented for the longest period of time. This is the place that you're going to put your strongest point.”
Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze) · Uri Levine
“The value is not about what the product does. The value is about the problem you solve. If you can describe the problem in a way that the person you're talking to says, 'oh my God, I have that problem,' you've won.”
Lessons from a two-time unicorn builder, 50-time startup advisor, and 20-time company board member | Uri Levine (co-founder of Waze) · Uri Levine
“We've been profitable from very early on. That changes everything about how you make decisions. You're not on someone else's timeline. You're on your own timeline.”
Inside Canva: Coaches not managers, giving away your Legos, and running profitably | Cameron Adams (co-founder and CPO) · Cam Adams
“Power requires a benefit and a barrier, so he's taking care of the benefit part by saying a castle, you have to have a pretty good understanding of why it's a castle and not a shack.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“You're on a treadmill and if you stop running on that treadmill, you get creamed, but it's not power. The things that drive operational excellence can be mimicked.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“There's a thing called power progression. There are times when certain types of power are available. The path to power is where the rubber meets the road.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“Network effects are the most powerful of the seven powers. If you have a product where every incremental user makes the product more valuable for every other user, that's an extraordinarily durable position.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“Counter-positioning is when a newcomer adopts a new, superior business model that the incumbent can't adopt because it would damage their existing business. This is what Netflix did to Blockbuster.”
Business strategy with Hamilton Helmer (author of 7 Powers) · Hamilton Helmer
“The most important thing about quitting is to set your criteria in advance. Decide when you will quit before you start. Once you're in it, your sunk cost bias will keep you going way too long.”
This will make you a better decision-maker | Annie Duke (author of “Thinking in Bets” and “Quit,” former pro poker player) · Annie Duke
“Live video taught me that you can build a product that people don't ask for and they don't know they want, and it can become something they can't live without. Periscope was that for me.”
Twitter’s former Head of Product opens up: being fired, meeting Elon, changing stagnant culture, building consumer product, more | Kayvon Beykpour · Kayvon Beykpour
“One of my mantras is just don't die. Being coached and being reminded of the fundamentals and basics puts you in the right mindset.”
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · Dalton Caldwell
“Seems like an unsolved problem. You'll get all this positive feedback from the world and people have been starting that startup since the '90s.”
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · Dalton Caldwell
“A good pivot is like going home. It's warmer, it's closer to something that you're an expert at.”
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · Dalton Caldwell
“We're trying to mix up some of the information diet about what kind of ideas people might be contemplating they are currently.”
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · Dalton Caldwell
“The founders who do best at YC are the ones who are resilient. They take the feedback, they iterate quickly, and they don't get emotionally attached to any single version of the product. They're attached to the problem.”
Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director) · Dalton Caldwell
“Finding product-market fit is the single most important thing that your startup does in the first three years, and it's just underexplored and it's just underexplained as a topic.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“We've published dozens of articles on the First Round Review, and we have found a very consistent set of patterns, demand satisfaction, and efficiency. But the interesting thing is that you don't go for all three of them from the very beginning.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“You've got the persona, the problem, the promise, and the product. Lattice kept the first one but changed the others. Vanta changed all four.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“Roughly, 60% are never going to get past L2.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“The best signal that you have nascent product-market fit is when customers start pulling the product from you. You don't have to push it anymore. They're asking you for it. That's a qualitative signal that data won't show you.”
A framework for finding product-market fit | Todd Jackson (First Round Capital) · Todd Jackson
“People often think that I get hired into later stage companies because I'm supposed to teach them how to operate like a big company, and in fact, I say I'm hired to remind them they can operate like a startup.”
Bending the universe in your favor | Claire Vo (LaunchDarkly, Color, Optimizely, ChatPRD) · Claire Vo
“In the early days of Gojek, there was a lot of resistance to our services. The most common form of that resistance was actually by motorcycle taxi mafia. These people would actually physically assault our drivers. We've had everything from bricks thrown at our drivers to knives and machetes being brandished at them. But instead of saying they're all contractors, let them sort it out, we actually hired private security to help extract them out of these sticky situations.”
Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek) · Kevin Aluwi
“I really don't like the idea of moats. I don't believe that any moats are durable over time. Eventually with enough time all moats can be crossed. One so-called moat that doesn't get talked about enough is the fact that you're able to do hard things because hard things are hard, and just simply doing things that are hard, as long as they create value to your customers, actually makes it harder for your competitors to win.”
Taxi mafias, cash vaults, and 100% MoM growth: The story behind Southeast Asia’s biggest startup | Kevin Aluwi (Gojek) · Kevin Aluwi
“The thing that I just like to encourage founders and product managers is just don't be afraid of sales. There's a lot of people out there who would love to tell you a story that it's magical or like, 'Oh, you've got to be a born seller,' and it's really not. Those people are just talking their book. Just getting good at those behaviors, it's going to benefit you in a myriad of ways.”
Founder-led sales | Pete Kazanjy (Founding Sales, Atrium) · Pete Kazanjy