Lenny’s Podcast103 min
Dalton Caldwell · Apr 18, 2024
Key learnings- Keep the startup alive: the core mantra is 'don't die,' since much of startup success comes from persisting through near-death…
- Before quitting, ask whether you still enjoy the work, your co-founders, and your customers; if you love those, lean toward…
- A good pivot moves 'warmer,' toward domains you already know or have built experience in, and often grows out of what you learned…
Lenny’s Newsletter · Free post♥ 330
Jul 5, 2022 · 64 min
“As a startup founder, you need to do the impossible. You build something that has never been built before, with a team that’s never worked together before, while learning dozens of new skills, making countless no-going-back decisions, all before you run out of money (and energy). It’s like being lost in the wilderness, in the dark, with only a vague sense of where you’re heading. Imagine if you had a map. From TikTok to Reddit to Uber…”
Lenny’s Newsletter · Free post♥ 494
Aug 8, 2023 · 40 min
Lenny Rachitsky opens a seven-part B2B startup playbook by examining how successful B2B companies found their original ideas. Drawing on dozens of founder interviews, he argues that a strong B2B idea combines an…
Lenny’s Podcast98 min
Uri Levine · Jun 9, 2024
Key learnings- Start with a meaningful problem you feel personally passionate about, since the journey is long and hard and passion sustains…
- Validate a problem by speaking with many people outside your close circle; if they describe the problem in their own words, it is…
- Expect a journey of failures and iterate quickly; failing fast leaves time for more attempts, which raises the odds of success.
Lenny’s Newsletter · Free post♥ 148
May 10, 2022 · 56 min
Todd Jackson, a seed-stage investor at First Round Capital, interviewed founders of eight companies (Vanta, Flexport, Cocoon, Good Dog, Snackpass, Rec Room, LaunchDarkly, Pinwheel) about how they chose and validated…
Lenny’s Newsletter♥ 326
Sep 12, 2023 · 35 min
Subscriber post — summary onlyPart five of a B2B startup series argues there is no formula for product-market fit, but founders' stories reveal a pattern. It proposes a five-step progression from one loving customer, to a paying customer, to…
Lenny’s Newsletter · Free post♥ 204
Oct 31, 2023 · 11 min
Jake Fuentes, co-founder of Cascade, reflects on the lessons from shutting down his B2B data-visualization startup after four years. He argues that failure rarely gets studied carefully, and that several decisions which…
Lenny’s Podcast150 min
Jason Fried · Dec 17, 2023
Key learnings- Software businesses have very low physical costs, so bootstrapping can be practical; treat cash flow and profit as the core skill…
- Venture-scale is an outlier path; most viable businesses sit in the large space between small and unicorn, so consider whether…
- Keep teams small and products simple; Fried argues constraints and a single product offering prevent the complexity that comes…
Lenny’s Newsletter · Free post♥ 108
Nov 22, 2022 · 26 min
Suril Kantaria, co-founder and CEO of Savvy, recounts the arc of a fintech startup that let employees buy their own health insurance with payment cards, from early missteps to a 2022 acquisition by a market incumbent…
Lenny’s Podcast193 min
Eric Ries · Oct 29, 2023
Key learnings- Treat a startup as an experiment: state the hypothesis, identify the leap-of-faith assumptions, and design the cheapest test that…
- An MVP is defined by the hypothesis being tested, not by a fixed level of stripped-down quality; it can be a brochure, a…
- Quality is defined by the customer, so teams that don't know their customer can't really know what a quality bar means; get early…
Lenny’s Newsletter · Free post♥ 243
Sep 17, 2024 · 24 min
Seed fundraising is presented as one of the most high-stakes and confusing parts of a founder's job, and this guide, co-written by two seed investors who have been involved in over 1,000 seed rounds, aims to make it…
Lenny’s Podcast116 min
Todd Jackson · Apr 11, 2024
Key learnings- Treat product-market fit as a progression across four levels rather than a binary, and expect it to take several years for most…
- At the nascent level, prioritize delivering insanely satisfying results to three to five customers; inefficiency such as manual…
- When stuck, change one or more of the four Ps (persona, problem, promise, product), and recognize that some companies keep one…
Lenny’s Newsletter♥ 566
Dec 9, 2025 · 12 min
Subscriber post — summary onlyGuest author Terrence Rohan shares how five early employees who joined multiple iconic companies, including Palantir, OpenAI, Stripe, and Spotify, spotted breakout startups early. The post argues that three signals…
Lenny’s Podcast83 min
Ivan Zhao · Mar 6, 2025
Key learnings- Hide a grand vision inside a product people already want: Notion's 'sugar-coated broccoli' approach meant shipping familiar…
- Test whether your early adoption comes from real users, not just from your own taste: Ivan warns that building too much for…
- Don't be afraid to reset the codebase when the foundation is wrong, and favor better abstractions, since a small core can…
Lenny’s Newsletter♥ 275
Jan 9, 2024 · 20 min
Subscriber post — summary onlyA founder whose product isn't gaining traction gets seven concrete options: talk to more users, narrow the target audience, rework positioning, try growth 'kickstarts', pivot to whatever shows pull, allow more time, or…
Lenny’s Podcast111 min
Andrew Wilkinson · Jul 3, 2025
Key learnings- Choose a business in an area you're genuinely interested in, but look for the unglamorous niche where competition is low…
- Pick a first business that delivers a quick, simple win, since early success builds the confidence and narrative needed to keep…
- Look for a unique edge (skills, background, or access to audiences) and pivot toward the most profitable customer segment for…
Lenny’s Newsletter♥ 239
May 16, 2023 · 11 min
Subscriber post — summary onlyLenny explains what investors mean by a "venture-scale" startup: a credible path to roughly $100M in annual revenue and a $1B+ valuation within about a decade. He argues most ideas, including many successful products…
Lenny’s Podcast131 min
Mike Maples Jr · Jul 7, 2024
Key learnings- Look for inflections: external turning points, whether technological, regulatory, or shifts in belief, that newly empower people…
- Stress-test any inflection by asking what specific new thing exists, how it empowers specific people, and under what conditions…
- A strong insight is non-obvious and non-consensus but also right; if everyone likes your idea, it is probably too similar to the…
Lenny’s Newsletter♥ 305
Aug 15, 2023 · 37 min
Subscriber post — summary onlyPart two of a B2B startup series examines how founders validate an idea before committing. Drawing on interviews with about two dozen companies, it lays out four validation paths (manual, listening, prototype with…
Lenny’s Newsletter · Free post♥ 92
Sep 1, 2020 · 21 min
Marc McCabe, an experienced angel investor who has helped dozens of startups raise money from pre-seed to Series C, argues that fundraising is best treated as a structured, trust-building process rather than a scramble…
Lenny’s Podcast84 min
Raaz Herzberg · Nov 17, 2024
Key learnings- Early in a startup, look for signs of real pull, such as prospects asking about pricing, timelines, or introducing you to their…
- Be willing to say 'I don't understand' in product discussions; a healthy culture makes admitting confusion a strength, and…
- Run a high volume of customer conversations (10 to 15 a day in Wiz's case) to find what actually resonates rather than relying on…
Lenny’s Newsletter♥ 93
Jan 25, 2022 · 25 min
Subscriber post — summary onlyLenny Rachitsky reviews more than 140 of his angel investments, sharing seven surprises, a practical path into angel investing, and his startup evaluation criteria. His core argument is that access to good deals and a…
Lenny’s Podcast102 min
Patrick Campbell · Feb 19, 2023
Key learnings- Define your values by the trade-offs they force, and assess candidates against them during interviews so misfits are filtered out…
- Ask whether your business can plausibly reach around $1 billion in annual revenue; if not, bootstrapping or building a…
- Campbell argues ProfitWell should have raised money earlier, since it could have pursued a larger outcome sooner, so match…
Lenny’s Podcast75 min
Pete Kazanjy · Dec 15, 2022
Key learnings- Founders should personally run sales first, since outsourcing it early breaks the feedback loop on whether the product and…
- Build a repeatable sales motion before hiring: aim for roughly a 15-25% conversion from first meeting to customer across cohorts…
- Iterate on your pitch continuously: after each objection, update slides, talk tracks, and collateral so the next cohort of…