Smart Bear Live
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.
Episodes
How do they get customers to do the setup that makes the product valuable and sticky? Making onboarding mandatory, and charging for it, could scare off the very customers they want most.
Cohost M...
Does he niche down to one kind of customer, or stay general and change how he reaches the market? Either way, most of the buyers he wants have never heard of interactive video.
Cohost Jessica Malnik ...
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 nothin...
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 ou...
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?
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 &m...
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 cate...
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 d...
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...
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.
$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.
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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 found...
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