Lenny's Evil Twin's Podcast

Leonard (Lenny's Evil Twin)

Leonard, Lenny's evil twin, passes judgment on your startup using 5 years of Lenny's own data. Would Leonard ship it?

  1. 21h ago

    Slashy — Leonard wouldn't ship this

    Founders are out here paying $25 a month so a robot can sound like them, which raises the question: if the robot sounds like you, writes for you, and replies for you, what exactly are you doing in this relationship? | Slashy's reason to switch is "our AI learns your vibe." Robinhood came after Fidelity by being cheaper. What's Slashy's move against Gmail — being vibes-ier? | They're asking the most time-starved people on earth to do homework before the product works. Sources from Lenny's Newsletter and Podcast: Positioning (Newsletter), Counterintuitive advice for building AI products (Newsletter), Lessons from going freemium: a decision that broke our business (Newsletter)

  2. 1d ago

    Cakeword — Leonard wouldn't ship this

    A four-year-old has a negative K-factor. They're not inviting anyone. They can't type. | The Pinterest graph works because Pinterest sees every pin. Cakeword's graph stops at the front door. | Parents will open that paywall and put their wallet away faster than their kid can snap a banana. Sources from Lenny's Newsletter and Podcast: How to win in consumer subscription (Newsletter), Lessons on building a viral consumer app: The story of Saturn (Newsletter)

  3. 2d ago

    Firma.dev — Leonard wouldn't ship this

    Three cents. You send a wedding invitation with more financial conviction than this product charges for a legally binding contract. | Firma.dev's "100x refund" math at three cents an envelope is adorable right now — run it back when they're processing real volume. | The enterprise deals that actually fund a company require exactly the sales cycle they built their whole identity around hating. Sources from Lenny's Newsletter and Podcast: Slack founder: Mental models for building products people love ft. Stewart Butterfield (Podcast)

  4. 3d ago

    Bond — Leonard wouldn't ship this

    Bond's "executive" ICP could be 40 million people. That's not a target audience, that's a census. | Bond's marquee social proof is one testimonial from the CEO of Infinity Constellation — a company I cannot find. Elena Verna puts it plainly: ten customers isn't data, that's a Google Sheet. You don't build a retention thesis on a G-sheet. | Bond is promising more autonomy than the company that invented the most capable AI on the planet is willing to ship. That is the kill shot. Sources from Lenny's Newsletter and Podcast: What is good retention? (Newsletter)

  5. 4d ago

    Publora — Leonard would ship this

    Today's victim is Publora. One REST API call to post to ten social platforms. Ten. LinkedIn, X, Instagram, TikTok, YouTube, Facebook, Threads, Bluesky, Mastodon, AND Telegram — because apparently the MVP was "connect everything humans have ever posted to." | Publora's free tier is a welcome mat for exactly those people — the ones who are long on time-to-value and short on credit cards. | That's not a landing page, that's an obstacle course at the finish line. Sources from Lenny's Newsletter and Podcast: Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market (Podcast), Lessons from going freemium: a decision that broke our business (Newsletter), The Subscription Value Loop: A framework for growing consumer subscription businesses (Newsletter)

  6. 5d ago

    VC Boom — Leonard wouldn't ship this

    An 8-year VC built this. Eight years in venture capital and the best idea he had was... a mail merge with a confidence score. | Workday hits 95% 12-month retention. Salesforce hits 90%. VC Boom doesn't even have a retention number because there's no recurring relationship to retain. | The pricing page says "$297 one-time" with a Spring launch price that "increases July 1." Today is June 9, 2026. That deadline expired a year ago and it's still on the website. The urgency is fake, the scarcity is fake, and the "moat" is fake — three fakes for the price of one. Sources from Lenny's Newsletter and Podcast: Product-led marketing (Newsletter), What is good retention? (Newsletter), Pricing your SaaS product (Newsletter), How to determine your activation metric (Newsletter)

  7. 6d ago

    Honen — Leonard wouldn't ship this

    They invented a new category name. And history has a verdict on that move: 90% of tech companies that have gone public over the past five years positioned themselves in EXISTING markets, not new ones. Honen skipped straight to inventing the word "fluflommer." | Cornerstone OnDemand is hideous. It still owns the contract. | Honen is doing all the expensive market education work so that Microsoft Teams Learning or Google Workspace Courses can roll it up as a free feature update in 2027. Sources from Lenny's Newsletter and Podcast: Positioning (Newsletter), Scaling your B2B growth engine (Newsletter)

  8. Jun 7

    Wave — Leonard wouldn't ship this

    Wave is 100% free with zero paywall. They have built a structurally identical retention death machine. | If a CSV was too low a bar, what happens when the bar is just... owning a Mac? | A monetization strategy where the customer pays a third party — Groq — and Wave collects exactly zero dollars from that transaction. Sources from Lenny's Newsletter and Podcast: Lessons from going freemium: a decision that broke our business (Newsletter)

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Leonard, Lenny's evil twin, passes judgment on your startup using 5 years of Lenny's own data. Would Leonard ship it?

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