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The surprising advice from a founder who built 2 unicorns | Jason Cohen (WP Engine)

23.7K views· 396 likes· 106:04· Jan 25, 2026

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How to Perform a Customer Churn Analysis (and Why You Should)

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Jira

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The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher)

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Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam:

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Pricing your SaaS product

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

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How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com)

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Jason Cohen is a four-time founder (including two unicorns, one being WP Engine) and an investor in over 60 startups, and has been sharing his lessons on company building at A Smart Bear for nearly 20 years. In this episode, Jason shares his methodical five-step framework for diagnosing stalled growth—a problem that faces almost every team. *We discuss:* 1. Jason’s five-step framework: logo retention, pricing, NRR, marketing channels, target market 2. A small tweak that’ll double response rates on your cancellation surveys 3. Why “it’s too expensive” is almost never the real reason customers cancel 4. The “elephant curve” of growth 5. How repositioning the same product can increase revenue 8x 6. When to reconsider if growth is even the right goal for your business *Brought to you by:* 10Web—Vibe coding platform as an API: https://10web.io/lenny Strella—The AI-powered customer research platform: https://strella.io/lenny Brex—The banking solution for startups: https://www.brex.com/product/business-account?ref_code=bmk_dp_brand1H25_ln_new_fs *Episode transcript:* https://www.lennysnewsletter.com/p/why-your-product-stopped-growing *Archive of all Lenny's Podcast transcripts:* https://www.dropbox.com/scl/fo/yxi4s2w998p1gvtpu4193/AMdNPR8AOw0lMklwtnC0TrQ?rlkey=j06x0nipoti519e0xgm23zsn9&st=ahz0fj11&dl=0 *Where to find Jason Cohen:* • Preorder Jason’s book: https://preorder.hiddenmultipliers.com/ • X: https://x.com/asmartbear • LinkedIn: https://www.linkedin.com/in/jasoncohen • Blog: https://longform.asmartbear.com • Website: https://wpengine.com *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Jason Cohen (05:19) Jason’s writing journey (08:25) Questions to ask when your product stops growing (18:17) Getting real customer feedback (20:27) Analyzing cancellation reasons (26:54) Onboarding and activation (29:35) Quick summary (35:46) Revisiting pricing strategies (41:46) Positioning strategies (47:52) Why pricing is inseparable from your strategy (52:06) The importance of net revenue retention (NRR) (01:00:25) Asking whether or not this is good for the customer (01:04:34) Leveraging existing customers (01:06:42) Are your acquisition channels saturated? The “elephant curve” (1:09:41) Why all marketing channels eventually decline (01:12:04) Direct vs. indirect marketing channels (1:13:36) Getting creative with new channels (01:19:04) Do you actually need to grow? (01:25:57) Deciding when to quit (01:29:27) Book announcement (01:33:21) AI corner (01:34:35) Contrarian corner (01:37:43) Lightning round and final thoughts *Referenced:* • Tyler Cowen’s website: https://tylercowen.com • How to Perform a Customer Churn Analysis (and Why You Should): https://www.groovehq.com/blog/learn-from-customer-churn • Linear: https://linear.app • Jira: https://www.atlassian.com/software/jira • Patrick Campbell’s post on X about pricing: https://x.com/Patticus/status/1702313260547006942 • The art and science of pricing | Madhavan Ramanujam (Monetizing Innovation, Simon-Kucher): https://www.lennysnewsletter.com/p/the-art-and-science-of-pricing-madhavan • Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam: https://www.lennysnewsletter.com/p/pricing-and-scaling-your-ai-product-madhavan-ramanujam • Pricing your SaaS product: https://www.lennysnewsletter.com/p/saas-pricing-strategy • M&A, competition, pricing, and investing | Julia Schottenstein (dbt Labs): https://www.lennysnewsletter.com/p/m-and-a-competition-pricing-and-investing • “Sell the alpha, not the feature”: The enterprise sales playbook for $1M to $10M ARR | Jen Abel: https://www.lennysnewsletter.com/p/the-enterprise-sales-playbook-1m-to-10m-arr • Buffer: https://buffer.com • AG1: https://drinkag1.com • How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com): https://www.lennysnewsletter.com/p/how-to-find-hidden-growth-opportunities-albert-cheng • How Duolingo reignited user growth: https://www.lennysnewsletter.com/p/how-duolingo-reignited-user-growth • The Elephant in the room: The myth of exponential hypergrowth: https://longform.asmartbear.com/exponential-growth • HubSpot: https://www.hubspot.com • Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building • Adjacency Matrix: How to expand after PMF: https://longform.asmartbear.com/adjacency/ ...References continued at: https://www.lennysnewsletter.com/p/why-your-product-stopped-growing _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com._ Lenny may be an investor in the companies discussed.

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