Smart Bear Live

About half of Userlist’s paying customers never fully set up the email automation they paid for. Jane Portman and Benedikt Deicke built Userlist over nine years for sophisticated SaaS marketers, but its onboarding is free and optional. 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 Mariya Delano and I dig in: A candid working session including: - an onboarding fee that “needs to hurt” - a one-person business that spent $20k on consulting - when a low price looks “suspicious” to buyers - a cofounder admits she can’t do enterprise sales - the $149 tier Jane says should be eliminated - they can’t name one podcast their buyers hear ME ME ME!!! Subscribe on YouTube Subscribe via Podcast 📘 Get my book 📘 My bio + 20 years of articles Twitter | LinkedIn STARRING JANE PORTMAN & BENEDIKT DEICKE Userlist Jane’s UI Breakfast podcast Twitter | LinkedIn Benedikt’s Slow & Steady…

Brett Lindenberg’s startup Mindstamp puts six figures of profit in his pocket every year, helping businesses create interactive videos for training and sales. But growth has leveled off, and he’s having trouble changing that. 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 and I dig in: A candid working session including: - the cheaper plan that has him fishing in bad waters - why his best buyers aren’t searching for him - SOC 2, and why Mindstamp should never issue the certificate - certifications people care about at the identity level - teaching better interactive video as the marketing ================= ME ME ME!!! ================= Subscribe on YouTube Subscribe via Podcast 📘 Get my book 📘 My bio + 20 years of articles Twitter | LinkedIn ============================= STARRING BRETT LINDENBERG ============================= Mindstamp Twitter | LinkedIn…

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…

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…

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…

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 +…

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…

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 |…

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…

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"…

$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…