BusinessEntrepreneurshipManagement

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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9 episodes
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Avg 1 hr 50 min
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#9
October 4 · 1 hr 54 min
E09 w/ Jon Sturgeon: AI changed his agency's model. Should he grow or sell?
Mario Peshev reduced his agency from 60 to 30 employees thanks to his own AI innovations. But almost nobody there is working on landing new clients. Pouring money into sales means building a machine he has never had. He could sell, but then he has to prove that this agency is worth a lot of money. Cohost Jon Sturgeon and I dig in: A candid working session including: - agencies in the world of AI - why an NPS of 90 proves nothing - bench time: waste, or a feature clients pay for? - a live cold-call role-play =============== ME ME ME!!! =============== Subscribe on YouTube 📘 Get my book 📘 My bio + 20 years of articles Twitter | LinkedIn ========================== STARRING MARIO PESHEV ========================== DevriX Personal site Newsletter Twitter | LinkedIn ================================ WITH COHOST JON STURGEON ================================ Dingus & Zazzy uhoh.com (an IT company for businesses that don’t have IT problems) Newsletter Twitter | LinkedIn =============================== REFERENCED IN THIS EPISODE =============================== “The Effortless Experience”—Dixon, Toman & DeLisi Hypergen, cold email TIMESTAMPS (00:00) - Can AI-run agencies survive the next five years (02:21) - Eighteen years building DevriX to a crossroads (07:10) - The walk-away number game (10:01) - Why productizing DevriX would be a mistake (18:23) - One and a half salespeople for a 35-person agency (30:45) - Why an NPS of 90 proves nothing (36:50) - Agencies in the age of AI: adapt or die (50:45) - Bench time: waste or a feature clients pay for (01:01:25) - Rebuilding go-to-market from scratch (01:24:22) - Live cold-call role-play (01:28:40) - Is a 6 million dollar exit even realistic (01:40:34) - EBITDA multiples and the AI-narrative buyer (01:44:35) - The real path forward: spin off, sell, or stay
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#8
September 27 · 1 hr 1 min
E08: Creating customer interview questions before you have customers
He built it, and they didn't come. Rison Simon built PainPointy to scan Reddit so that marketers could learn the pain points of their customers and come up with article ideas. The problem is he's never had more than six customers. So he has to go interview customers and potential customers, which means first knowing what to ask them. We workshop that with my Iterative Hypothesis method — inventing the questions, then working out which ones are best. ME ME ME!!! Subscribe on YouTube 📘 Get my book 📘 My bio + 20 years of articles Twitter | LinkedIn STARRING RISON SIMON PainPointy Blog Substack Twitter | LinkedIn REFERENCED IN THIS EPISODE The Iterative Hypothesis Method AI skills that implement the Iterative Hypothesis Method TIMESTAMPS (00:00) - He sold his last startup the week he launched it - this one has almost no customers (02:09) - What PainPointy actually does, and why Rison can't say who wants it (08:37) - The Iterative Hypothesis Method: write down what you think before you ask (14:19) - Why does it have to be B2B? Interrogating your own assumptions (19:08) - The question that doesn't lead the witness (28:33) - Quantity vs quality of leads: the customer who's actually easy to win (39:08) - The real problem isn't a shortage of ideas, it's knowing which one to pick (50:23) - Powers of 10: turning vague guesses into testable numbers (58:11) - Where to actually find people who will talk to you
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#7
September 20 · 1 hr 8 min
E07 w/ Dan Martell: 1 big logo won't get him the next 10
How can George Paladichuk take his startup NaiL from 1 huge customer, to the next 100 customers? Cohost Dan Martell and I dig in: A candid working session including: - finding early adopters in public data - reading job postings to find your buyer's software - the $15K way inside a global franchise - products for many instead of a product for one - should he chase elephants or mid-market? ======================= ME ME ME!!! ======================= Subscribe on YouTube Get my book My bio + 20 years of articles Twitter | LinkedIn ======================= STARRING GEORGE PALADICHUK ======================= NaiL George's site LinkedIn YouTube ======================= WITH COHOST DAN MARTELL ======================= Dan Martell Growth Stacking Show (podcast) Martell Method (newsletter) YouTube https://twitter.com/danmartell https://ca.linkedin.com/in/dmartell ======================= REFERENCED IN THIS EPISODE ======================= "Buy Back Your Time"—Dan Martell "Crossing the Chasm"—Geoffrey A. Moore TIMESTAMPS (00:00) - Intro: NaiL runs on 90% revenue from one client (01:23) - George introduces NaiL, an AI receptionist for franchise brands (02:58) - Standing out among 800 AI receptionist competitors (04:53) - The real bottleneck: enterprise deals are too slow (08:59) - Why chasing Main Street customers is harder than it looks (12:33) - Money vs speed: mapping enterprise, mid-market, and small business (18:26) - Crossing the chasm: finding customers who already want new tech (23:00) - George commits: doing franchise, not vague "enterprise" (27:02) - The three Fs for spotting early adopters: follow, fund, frequent (35:21) - The holding company angle: land ten brands through one parent (42:59) - Selling a low-cost pilot to get a foothold in new brands (47:41) - Dan's Irving Oil story: the danger of concentration risk (59:12) - Is NaiL a real product, or a bespoke dev shop for one client? (01:04:02) - Dan's homework: partners, conferences, and non-competing locals
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#6
September 13 · 1 hr 41 min
E06 w/ Bryce Adams: Pivoting his strategy into his strengths
Carl Alexander built Ymir — a serverless AWS platform that deploys WordPress and PHP applications onto a customer's own AWS account — and the twenty-five customers who run production stores on it never leave. They also all pay $39 a month, and nobody new signs up. Did four years falsify the market, or was it the wrong buyers? It's the second one. The $39, the self-serve signup, the WordPress developer he kept aiming at — every piece of the offer points away from the thing he's world-class at, which is teaching people how this works. Cohost Bryce Adams bootstrapped Metorik on the same platform, and he's been telling Carl to charge more for years. He and I dig into who the buyer actually is, and what Carl should be selling him. A candid working session including: - five years of talks, zero customers - $39 versus "bet our company on it" - the joke tier he shouldn't have deleted - what Metorik charged from day one - should he stop going to conferences? ME ME ME!!! Subscribe on YouTube 📘 Get my book 📘 My bio + 20 years of articles Twitter | LinkedIn STARRING CARL ALEXANDER Ymir Ymir Reports Blog Twitter | LinkedIn WITH COHOST BRYCE ADAMS Metorik Twitter REFERENCED IN THIS EPISODE "Using the Needs Stack for Competitive Strategy" "SaaSocalypse" video by Jesse Hanley TIMESTAMPS (00:00) - A business customers love but that nobody buys - framing the puzzle, then Carl Alexander and cohost Bryce Adams (Metorik) (04:08) - Diagnosing 4 years of failed WordPress-developer marketing - and proving the market already exists (12:40) - Rejecting the succession-plan fix, then hunting the buyer pattern in Carl's 4 paying customers (17:22) - Engaged developers aren't buyers: why the "resonating" marketing wasn't actually working (22:45) - Finding the real decision-maker: not the developer who claps, the CTO who signs (26:40) - The $39/mo price that contradicts "mission-critical, dependable" (40:10) - "Carl as a service": the $20K consulting offer bundled with $500/mo software (54:29) - Landing on $1,000/mo, validated by Bryce's own Metorik pricing history (59:32) - Redefining the ideal customer: a $5M+ GMV WooCommerce store (01:09:29) - Sell to agencies, not individual stores (01:19:25) - The ICP crystallizes: an agency already committed to AWS that just needs expert help (01:31:25) - The conference rule: only go for leads or credibility (01:37:56) - Carl commits to raise the price before this episode airs (01:40:29) - Closing: the WordCamp party story
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#5
September 6 · 2 hr 1 min
E05 w/ Laura Roeder: Scared to commit to his best customers
Hasan Cagli tripled PostPlanify to $3K MRR the month he started selling to agencies instead of indie hackers. The agencies use it every day, ask for features, and stay. Everyone else signs up, pokes around, and churns. Which means the niche is already sitting in his own customer list. But winning there means giving up customer number seven -- the one he's actually worried about. Cohost Laura Roeder built MeetEdgar in this exact category, scaled it past $5M ARR, and sold it. She and I dig into what it costs to stay vague -- including the years MeetEdgar spent on a niche defined by a feature instead of a buyer. A candid working session including: - "agency" is not a niche, it's one facet - the number 7 customer trap - sizing the market with powers of ten - what MeetEdgar's niche got wrong - pricing by workspace, not by account ME ME ME!!! Subscribe on YouTube 📘 Get my book 📘 My bio + 20 years of articles Twitter | LinkedIn STARRING HASAN CAGLI PostPlanify Twitter | LinkedIn YouTube WITH COHOST LAURA ROEDER Founder at Paperbell Read her blog at Twitter REFERENCED IN THIS EPISODE "Your target market isn't demographic" "The Ultimate Sales Machine" — Chet Holmes TIMESTAMPS (00:00) - Intro: the agency vs indie hacker churn problem (03:13) - Hasan's numbers: 3.5K MRR and why agencies stick (06:59) - The pricing tiers and the missing workspace math (10:12) - The case for going all in on agencies (26:51) - His Turkish identity: the advantage he is not using (36:37) - Mapping the niche: agency, simple, local (45:30) - The number 7 customer trap (52:38) - Niching case studies: WP Engine, Toast, Shopify, Acquia (01:04:43) - Sizing the market with powers of ten (01:07:08) - MeetEdgar's niche mistake, from Laura herself (01:23:10) - Even Apple and Uber started niche (01:28:16) - The product fork: agency tool vs client login (01:42:26) - Pricing by workspace: the rule of thumb (01:49:25) - Go to market: Dream 100 and cold outreach (01:56:51) - Nathan Barry's dissatisfaction pitch trick (02:00:06) - Closing line: go niche down without fear
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#4
August 30 · 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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