Smart Bear Live
Smart Bear Live is a business therapy podcast hosted by Jason Cohen, also known as "A Smart Bear" online. He and a rotating co-host provide brutally honest advice to founders of real companies facing genuine puzzles and struggles. The show cuts to the heart of issues and helps rebuild with ideas, options, strategies, and decisions. It's like a therapy session for businesses.
Episodes
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 o
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 — in
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?======
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 WordPres
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 Lau
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 o
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 va
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. =======
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 h
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