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Startup Strategy

15 claims6 moments4 on the cutting room floor

Lenny's Written Position

Freemium should not be implemented until a company truly understands how to convert leads to customers, typically 2-3 years into the business.

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The single goal of an early-stage pre-PMF startup should be to make 10 customers very happy, and everything prioritized should serve this goal.

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Early-stage startups should not try to be data-driven because they simply do not have enough data for statistical significance; a 10% improvement at 20% conversion requires over 5,000 users.

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Startups should not build everything users ask for but instead focus on understanding user pain points and independently designing the best solutions.

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The next big thing will start out looking like it is for a niche network, which is why new networked products are easy to underestimate.

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Founding teams should create the first growth model themselves rather than outsourcing it to a Head of Growth hire, because only they understand the DNA of the product and market deeply enough.

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A wedge is a strategy to win a large market by initially capturing a tiny part of a larger market or a large part of a small adjacent market, then expanding from that foothold.

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A wedge is most essential when going after a market that is entrenched or crowded; companies like Zoom, Slack, and Notion won large markets straight-on without a wedge by having an amazing product.

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Poor distribution, not product, is the number one cause of startup failure, and getting your product in front of the right people efficiently is increasingly what separates winners from losers.

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There are seven early-stage distribution advantages: pre-existing audience, unique viral loop, being first on an emerging platform, remarkable story, pre-existing relationships, strategic partnerships, and extraordinary hustle.

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A strong 'why now' is helpful but not essential for building a large business; companies like SpaceX, Airbnb, Pinterest, DoorDash, and Facebook had little or no why-now at founding.

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A strong why-now creates one of two advantages: it unlocks the ability to provide a 10x better product (like smartphones enabling Uber) or it creates a new untapped market need (like remote work enabling Zoom).

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There are eight fundamental business model types: sell a thing, rent a thing, take a cut, charge a subscription, charge for usage, sell access, sell attention, and charge per transaction.

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The most important factor in early-stage hiring success is the effectiveness of the company's mission or vision in compelling top candidates.

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Hiring compounds: great early hires create a snowball effect where the quality of the existing team organically attracts more exceptional people.

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Podcast Moments

Dharmesh Shah00:00:00
Some of the best startup advice I've heard is startups should focus on one thing and be really, really exceptionally world-class at that one thing. And one of our early zigs is we are going to do exactly the opposite of that.

Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO) · Dharmesh Shah

Sarah Tavel00:00:00
I think a lot of people think about markets almost like these bodies of water, it's like it's this big body of water that we're going after. I actually think that the most interesting markets, you have to think of them like currents where there's something happening in the market that's creating this current where you can have a plank of wood that you've put on the river and it's going to pull you forward.

The hierarchy of engagement | Sarah Tavel (Benchmark, Greylock, Pinterest) · Sarah Tavel

Sarah Tavel00:00:00
Versus a market that doesn't really have that momentum to it, you're going to have to build something really big and fancy to make any progress.

The hierarchy of engagement | Sarah Tavel (Benchmark, Greylock, Pinterest) · Sarah Tavel

Brian Balfour00:00:33
If you're a late-stage company, you place multiple bets. For startups, it's a totally different ballgame. You have to choose one and go all in.

Brian Balfour: 10 lessons on career, growth, and life · Brian Balfour

Julia Schottenstein00:00:00
M&A is always about creating plan Bs. And the way I would think about it is for any one company, there's only ever two to three buyers that find what you're building to be extremely strategic.

M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs) · Julia Schottenstein

Lulu Cheng Meservey00:11:34
If you're a startup your enemy is the status quo. When you don't take risks, when you minimize risk by doing nothing, you're letting the status quo win. I always encourage people to try to make mistakes of commission rather than omission. Because if you make a mistake of commission you can observe it, you can learn from it. Whereas if you make mistakes of omission you're not observing, you're not learning, and you're maybe not even noticing opportunities slip by.

Navigating comms and PR | Lulu Cheng Meservey (Substack, Activision Blizzard) · Lulu Cheng Meservey

Cutting Room Floor

Guest insights on this topic that Lenny hasn't (yet) written about in his newsletters. Potential material for future posts.

Dharmesh ShahUnsynthesized
Some of the best startup advice I've heard is startups should focus on one thing and be really, really exceptionally world-class at that one thing. And one of our early zigs is we are going to do exactly the opposite of that.

Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO) · Dharmesh Shah

Sarah TavelUnsynthesized
Versus a market that doesn't really have that momentum to it, you're going to have to build something really big and fancy to make any progress.

The hierarchy of engagement | Sarah Tavel (Benchmark, Greylock, Pinterest) · Sarah Tavel

Julia SchottensteinUnsynthesized
M&A is always about creating plan Bs. And the way I would think about it is for any one company, there's only ever two to three buyers that find what you're building to be extremely strategic.

M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs) · Julia Schottenstein

Lulu Cheng MeserveyUnsynthesized
If you're a startup your enemy is the status quo. When you don't take risks, when you minimize risk by doing nothing, you're letting the status quo win. I always encourage people to try to make mistakes of commission rather than omission. Because if you make a mistake of commission you can observe it, you can learn from it. Whereas if you make mistakes of omission you're not observing, you're not learning, and you're maybe not even noticing opportunities slip by.

Navigating comms and PR | Lulu Cheng Meservey (Substack, Activision Blizzard) · Lulu Cheng Meservey