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Smart Bear Live

Jason Cohen

A room of founders, a different crew for each episode,
taking the time to dig into the details of a real, live business,
being brutally honest with facts (and with love for people),
being vulnerable (but with hope),
explaining our approach, mindset, frameworks, and life experiences,
so that listeners learn tactics but also strategic thinking,
and the star of the show — the founder in the arena — makes progress.

No ads, no affiliate links, no heavy editing, no follow-on courses or consulting.
We're doing this for each other and for the love the game.

It's a workshop, but also it's therapy. Because for founders, there's little distinction.

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  • 4 episodes
  • Avg 2 hr 11 min
  • English

Episodes 4

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  • #4
    Today · 1 hr 56 min

    E04 w/ Dr. Sherry Walling: He built a great business, but it doesn't feel like it

    Every founder faces this eventually. You spend every waking second just trying not to fail completely, so when it's actually working, you barely recognize it and don't know what to do with yourself. That's where Patrik Inzinger is. appointmed is calm and profitable at €2M ARR, ~1% churn, and a team of 8 that no longer needs him day to day. Which leaves: who am I, and what do I even want out of life? Cohost Dr. Sherry Walling and I dig into that question — and discover it was never about a bigger revenue number. It's about being seen. A candid working session including: - comparing yourself to other people's headlines - is a calm, profitable company "enough" - why hypergrowth isn't fun, it's fulfilling - the hunger to be recognized - the failure story he's carried for 15 years - choosing the right mirrors, ignoring the trolls - separating the company's mission from your own - the "what would have to be true" growth test ME ME ME!!! Subscribe on YouTube 📘 Get my book 📘 My bio + 20 years of articles Twitter | LinkedIn STARRING PATRIK INZINGER appointmed Homepage Slow & Steady newsletter Twitter | LinkedIn | Bluesky WITH COHOST DR. SHERRY WALLING ZenFounder Exit Strategy (book) Touching Two Worlds (book and show) Website | Twitter REFERENCED IN THIS EPISODE "Momentum without a mission" — Patrik Inzinger "Mission, Vision, poTAYto, poTAHto" "Max MRR: Your Growth Ceiling" TIMESTAMPS

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  • #3
    August 23 · 2 hr 30 min

    E03 w/ Craig Hewitt: Restarting growth after stuck at €16k/mo

    Tiago Ferreira and João Amaro bootstrapped their AI podcast-repurposing tool Podsqueeze from zero to €16K/mo in less than a year, but then watched it sit flat for two years despite more features, better SEO, and free trials. Cohost Craig Hewitt (Castos) and I dig into the real problem: the self-serve podcaster market is structurally brutal—most shows fade within months, so the product's value fades with them—and the real money is up-market, with agencies and media companies who barely churn. A candid working session including: - why "too expensive" is never the real churn reason - pricing to value - the 5x price test that proved they're nowhere near the ceiling - enterprise vs. just-big customers - positioning an all-in-one tool - what a plateaued "sideways" business is actually worth when someone offers to buy it ME ME ME!!! Subscribe on YouTube 📘 Get my book 📘 My bio + 20 years of articles Twitter | LinkedIn STARRING TIAGO FERREIRA & JOÃO AMARO Podsqueeze Tiago's podcast, Indie Founder Twitter | LinkedIn Twitter | LinkedIn WITH COHOST CRAIG HEWITT Castos More About Craig Rogue Startups podcast Twitter | LinkedIn REFERENCED IN THIS EPISODE "Pricing determines your business model" "How repositioning a product allows you to 8x its price" TIMESTAMPS (00:00) - Meet the founders: bootstrapped to 16K, then stuck for two years (03:09) - Riding the GPT wave to 14K, then two flat years (09:03) - Podcast fade: why most customers quit within months (20:26) - Why 'too expensive' is never the real reason they cancel (26:50) - The Portugal B2B win, and why it won't travel abroad (34:35) - Enterprise vs. just a big customer: Joe Rogan isn't enterprise (49:43) - The 5x price test: they raised it and nobody blinked (57:33) - The Shopify model: how brutal churn can still win (01:03:40) - Charge for what grows as the customer grows (01:14:40) - Selling to agencies: why the demos never close (01:20:53) - Why enterprises take the meeting, then never buy (01:37:48) - The all-in-one bet: good enough beats best-in-class (01:52:07) - A homepage that's a mess because it talks to everyone (01:55:45) - The 500K offer they turned down: sell or double down? (02:02:16) - AI should kill the busy work, not make the content (02:18:42) - What your SEO traffic is actually worth (02:26:22) - Stuck in a bad market, and the path to a better one

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  • #2
    August 16 · 2 hr 14 min

    E02 w/ Rob Walling: $1M ARR, how to expand into a new market

    DropInBlog's Jesse Schoberg has 2,000 happy customers, 2% monthly churn, a Bangkok-nomad life—and a growth curve that has plateaued. I and co-host Rob Walling tear into the real problem: a proven new cohort without a go-to-market plan. Two hours on pricing, positioning, AI/LLM visibility, the agency channel, ABM, and how to expand without breaking the business people already love. ==================== ME ME ME!!! ==================== Subscribe on YouTube 📘 Get my book 📘 My bio + 20 years of articles Twitter | LinkedIn ========================== STARRING JESSE SCHOBERG ========================== DropInBlog Homepage Twitter | LinkedIn ========================== WITH COHOST ROB WALLING ========================== All About Rob TinySeed MicroConf Startups For the Rest of Us (podcast) The SaaS Playbook Twitter ============================= REFERENCED IN THIS EPISODE ============================= "Max MRR: Your growth ceiling" "The Elephant Curve & the myth of exponential growth" "The Seven Types of SaaS Plateaus" — Rob Walling, MicroConf talk "How to Get Mentioned in ChatGPT (Data from 2,000 Sites)" — Jesse Schoberg, MicroConf talk "The SaaS Playbook" — Rob Walling's book Timestamps: 0:00 The $1M-a-year nomad founder who hit a growth wall 5:56 Big companies were visiting his site — and he had nothing to sell them 12:17 "Useful" isn't "delight": why nothing in the pitch excites buyers 19:27 Going upmarket without wrecking the simple product people love 22:19 How to price when a $49 and a $999 plan share one page 25:53 Marketing budgets are getting cut — sell them their job back from AI 36:43 Marketer or engineer: who actually clicks "book a demo"? 45:49 Run ads to discover your message, not for ROI 51:19 Stop fishing in the pond you like — go where the best customers are 1:04:40 The agency channel: land one, get many customers over time 1:14:33 Account-based marketing: courting a few whales for years 1:21:20 Run your own event to become the category expert 1:28:29 The seven types of SaaS plateau — which one is yours? 1:37:07 How to roll out a new strategy without scaring your team 1:48:44 Every big bet needs one owner who thinks of nothing else 2:04:13 What agencies want more than a kickback

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  • #1
    July 23 · 2 hr 4 min

    E01: Restarting growth when stuck at $32K MRR

    $32K MRR, 9% churn, flat growth, but we figured out a strategy for how to restart growth. The thought process behind the analysis and determining a strategy, not just knee-jerk answers. Subscribe to A Smart Bear on YouTube 📘 Pre-order my book! 📘 Dmytro runs a profitable screenshot-API SaaS: ~1,000 customers, $32K MRR, four years in — and dead flat. He wants to triple it to $100K MRR, so he did something almost no founder will do on camera: he opened his entire dashboard and let me poke at all of it. (Dmytro's company is ScreenshotOne) (Follow Dmytro on Twitter) We work backward from the numbers. First, the math nobody wants to see: Deriving a hard ceiling around $40K — at 9% churn he literally can't reach $100K without changing something structural. Then the harder truth underneath it: in four years and thousands of customers, no single big, repeatable market for screenshots-as-an-API has ever shown up. That's the real crux — not the churn number, the missing market. (I might be wrong, and we pressure-test that too.) Instead of one "fix," we put four honest options on the table, all based on his personality and goals, and talk through how each one actually feels, not just whether it pencils out. If you've ever hit a plateau and couldn't tell whether to push, pivot, or quit, this is the whole reasoning process, out loud. 📄 Articles from the conversation: • The churn-ceiling math — why ~$40K is a wall: "Max MRR: Your growth ceiling" • The growth-curve chart I showed on screen — why real SaaS grows linearly until PMF: "Product/Market Fit: Experience & Data" • Why even "hypergrowth" isn't exponential (the acceleration trap): "The myth of exponential hypergrowth" • How to interview customers — the method for vetting Option D: "The Iterative-Hypothesis customer development method" Pre-order my book, Hidden Multipliers 📘 Follow A Smart Bear on: Twitter | LinkedIn | Bluesky | Newsletter 📩 About Jason Cohen (a.k.a. A Smart Bear): As a four-time entrepreneur across 25 years, both bootstrapped and VC-funded, resulting in two exits and two unicorns (Smart Bear & WP Engine), I've also been writing about everything I know for 18 years. Now I'm making some videos. More about me

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