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Jason Cohen

Smart Bear Live

A Entrepreneurship , Business and Management podcast Explicit

#142 in Entrepreneurship · 🇵🇭 #143 in Entrepreneurship · 🇩🇰
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About the show

The show where a startup founder takes the hot seat, opens up their business, and explains their biggest challenge. Then we dig in: a few other founders who have already solved that challenge in their own businesses. This is not an interview. There's no script. This is the messy, uncomfortable process of solving a real puzzle faced by a real company. 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. For founders, what's the difference?

Newest episodes

E13 w/ Ruben Gamez: How to Restart Growth in a Stagnant SaaS Business

1 hr 9 min

Michael Koper says Nusii, his proposal software, is simpler than its rivals, but every one of those rivals say that too. Revenue has been flat for a few years now at around $10k per month.How does he stand out? Buyers do indeed want “simple,” but what else?Cohost Ruben Gamez and I dig in: A candid working session including:- Ruben dislikes attention, until it brings paid upgrades- agencies stay with Nusii, but too few sign up- are missions only interesting to big customers?- Nusii’s homepage says “serious” but also “simple”- the loyal, paying customer who’s still a lossME ME ME!!!Subscribe on YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING MICHAEL KOPERFounder of NusiiTwitter | LinkedIn WITH COHOST RUBEN GAMEZFounder of eSign software SignWell and proposal app Bidsketch.SignWellBidsketchTwitter | LinkedIn TIMESTAMPS (00:00) - Proposal software stuck at $10k a month (02:09) - Homepage headline: why "serious" misses (07:56) - Why proposal software wins more deals (13:59) - Table-stakes features vs. being simplest (21:18) - Everyone claims simple: compete with Word (29:21) - Don't go horizontal in a crowded market (33:34) - Commodity products need a real vertical (39:00) - Marketing when it's not your strength (42:43) - Narrowing down the target customer (46:34) - Conferences: when they're worth the trip (52:46) - A mission: help customers win deals (01:00:15) - Finding a mission later, like WP Engine (01:06:02) - Standing out still needs 10x the leads

E12 w/ Tibo Maker: How can a $40K MRR SaaS be losing 20% of Its Customers

1 hr 20 min

20% of Post Bridge's customers leave every month -- massive churn that puts a hard ceiling on growth. Jack Friks’s tool sends posts to many social platforms from one dashboard, and he built it in public on X, where his personality attracted other builders, but not the business marketers he needs. How does he choose the customer to build for? Asked what Post Bridge does best, he says, “I don’t know.” Cohost Tibo Louis-Lucas and I dig in: A candid working session including:- Tibo's one-price fix: $1 per account, minimum 30- why an A/B test won't tell you your ICP- is LinkedIn where his real buyers are?- how narrowing the ICP expands sales, but it never feels like it- be himself online, or change for his customer?- users with 15+ accounts expect to pay $500, not 50 ME ME ME!!!Subscribe on YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING JACK FRIKSCurious guy who likes creating things and loves his wifewebsitepost bridgeTwitter WITH COHOST TIBO LOUIS-LUCASBootstrapped SaaS founder. Sold Tweet Hunter and Taplio to lempire in 2022 ($10m), now building Revid, Outrank, Squad, Bazzly, PostSyncer and SuperX (yeah that’s a lot 😅)Newsletter (80k+ founders) & portfolioRevid, AI videoOutrank, SEO on autopilotBazzly, acquisition on RedditSquad, AI teammates for workSuperX, grow on XTwitter | LinkedIn TIMESTAMPS (00:00) - Doubling Post Bridge despite 20% churn (04:26) - Make AI plugin signups stick (09:41) - Growth spurts, and being best at one thing (13:18) - Features you wouldn't hand to an LLM (18:20) - 20% churn and three kinds of cancels (28:06) - Fix churn at the top of the funnel (35:40) - Channel-founder fit vs. the ICP (39:51) - Defining an ICP that actually exists (45:00) - Why LinkedIn may be the best channel (49:21) - Stay yourself, but know your audience (53:58) - Which churn is worth fixing (56:25) - Is $100k MRR the real goal? (59:12) - Pricing: why fewer choices convert (01:02:40) - Who each pricing tier is for (...

E11 w/ Mariya Delano: How to Fix a SaaS Trial-to-Paid Conversion Problem

1 hr 12 min

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 YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING JANE PORTMAN & BENEDIKT DEICKEUserlistJane’s UI Breakfast podcastTwitter | LinkedInBenedikt’s Slow & Steady podcastTwitter | LinkedIn WITH COHOST MARIYA DELANOKalyna MarketingThe Marketing Speakeasy podcastADMD newsletterLinkedIn REFERENCED IN THIS EPISODETinySeedMicroConfSegment“Marketing Technology Landscape”—chiefmartec TIMESTAMPS (00:00) - Userlist's stalled growth: who is it for? (03:53) - Why growing customers cancel (09:10) - Email ROI is measurable: wrong customers? (12:51) - Lost champion: spread value beyond one user (20:09) - Fixing onboarding: HubSpot's forced training (24:14) - A $10K implementation fee for onboarding (31:34) - Selling to bigger budgets: the $20K client (36:29) - Priced below Mailchimp and ConvertKit (44:00) - Where are the customers for geeky features? (48:25) - Should Userlist go simple and down market? (53:52) - Do thousands of geeky marketers exist? (57:40) - Next steps: interviews and $20K onboarding (01:03:00) - Be proud of the path that got you here (01:07:11) - Imposter syndrome and perfectionism

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All episodes

E13 w/ Ruben Gamez: How to Restart Growth in a Stagnant SaaS Business

1 hr 9 min

Michael Koper says Nusii, his proposal software, is simpler than its rivals, but every one of those rivals say that too. Revenue has been flat for a few years now at around $10k per month.How does he stand out? Buyers do indeed want “simple,” but what else?Cohost Ruben Gamez and I dig in: A candid working session including:- Ruben dislikes attention, until it brings paid upgrades- agencies stay with Nusii, but too few sign up- are missions only interesting to big customers?- Nusii’s homepage says “serious” but also “simple”- the loyal, paying customer who’s still a lossME ME ME!!!Subscribe on YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING MICHAEL KOPERFounder of NusiiTwitter | LinkedIn WITH COHOST RUBEN GAMEZFounder of eSign software SignWell and proposal app Bidsketch.SignWellBidsketchTwitter | LinkedIn TIMESTAMPS (00:00) - Proposal software stuck at $10k a month (02:09) - Homepage headline: why "serious" misses (07:56) - Why proposal software wins more deals (13:59) - Table-stakes features vs. being simplest (21:18) - Everyone claims simple: compete with Word (29:21) - Don't go horizontal in a crowded market (33:34) - Commodity products need a real vertical (39:00) - Marketing when it's not your strength (42:43) - Narrowing down the target customer (46:34) - Conferences: when they're worth the trip (52:46) - A mission: help customers win deals (01:00:15) - Finding a mission later, like WP Engine (01:06:02) - Standing out still needs 10x the leads

E12 w/ Tibo Maker: How can a $40K MRR SaaS be losing 20% of Its Customers

1 hr 20 min

20% of Post Bridge's customers leave every month -- massive churn that puts a hard ceiling on growth. Jack Friks’s tool sends posts to many social platforms from one dashboard, and he built it in public on X, where his personality attracted other builders, but not the business marketers he needs. How does he choose the customer to build for? Asked what Post Bridge does best, he says, “I don’t know.” Cohost Tibo Louis-Lucas and I dig in: A candid working session including:- Tibo's one-price fix: $1 per account, minimum 30- why an A/B test won't tell you your ICP- is LinkedIn where his real buyers are?- how narrowing the ICP expands sales, but it never feels like it- be himself online, or change for his customer?- users with 15+ accounts expect to pay $500, not 50 ME ME ME!!!Subscribe on YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING JACK FRIKSCurious guy who likes creating things and loves his wifewebsitepost bridgeTwitter WITH COHOST TIBO LOUIS-LUCASBootstrapped SaaS founder. Sold Tweet Hunter and Taplio to lempire in 2022 ($10m), now building Revid, Outrank, Squad, Bazzly, PostSyncer and SuperX (yeah that’s a lot 😅)Newsletter (80k+ founders) & portfolioRevid, AI videoOutrank, SEO on autopilotBazzly, acquisition on RedditSquad, AI teammates for workSuperX, grow on XTwitter | LinkedIn TIMESTAMPS (00:00) - Doubling Post Bridge despite 20% churn (04:26) - Make AI plugin signups stick (09:41) - Growth spurts, and being best at one thing (13:18) - Features you wouldn't hand to an LLM (18:20) - 20% churn and three kinds of cancels (28:06) - Fix churn at the top of the funnel (35:40) - Channel-founder fit vs. the ICP (39:51) - Defining an ICP that actually exists (45:00) - Why LinkedIn may be the best channel (49:21) - Stay yourself, but know your audience (53:58) - Which churn is worth fixing (56:25) - Is $100k MRR the real goal? (59:12) - Pricing: why fewer choices convert (01:02:40) - Who each pricing tier is for (...

E11 w/ Mariya Delano: How to Fix a SaaS Trial-to-Paid Conversion Problem

1 hr 12 min

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 YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn STARRING JANE PORTMAN & BENEDIKT DEICKEUserlistJane’s UI Breakfast podcastTwitter | LinkedInBenedikt’s Slow & Steady podcastTwitter | LinkedIn WITH COHOST MARIYA DELANOKalyna MarketingThe Marketing Speakeasy podcastADMD newsletterLinkedIn REFERENCED IN THIS EPISODETinySeedMicroConfSegment“Marketing Technology Landscape”—chiefmartec TIMESTAMPS (00:00) - Userlist's stalled growth: who is it for? (03:53) - Why growing customers cancel (09:10) - Email ROI is measurable: wrong customers? (12:51) - Lost champion: spread value beyond one user (20:09) - Fixing onboarding: HubSpot's forced training (24:14) - A $10K implementation fee for onboarding (31:34) - Selling to bigger budgets: the $20K client (36:29) - Priced below Mailchimp and ConvertKit (44:00) - Where are the customers for geeky features? (48:25) - Should Userlist go simple and down market? (53:52) - Do thousands of geeky marketers exist? (57:40) - Next steps: interviews and $20K onboarding (01:03:00) - Be proud of the path that got you here (01:07:11) - Imposter syndrome and perfectionism

E10 w/ Jessica Malnik: Plateaued at six figures, but still hungry

1 hr 11 min

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 YouTubeSubscribe via Podcast📘 Get my book 📘My bio + 20 years of articlesTwitter | LinkedIn =============================STARRING BRETT LINDENBERG=============================MindstampTwitter | LinkedIn ==================================WITH COHOST JESSICA MALNIK==================================HomepageSubscribe on NewsletterSubscribe on YouTubeThe Remote Work TribeTwitter | LinkedIn ================================REFERENCED IN THIS EPISODE================================“The Iterative-Hypothesis customer development method”“Not Business Advice” books—Alex West TIMESTAMPS (00:00) - Plateaued SaaS: niche down or stay general? (04:11) - Too general, or just customizable? (08:21) - Who sticks? Medical continuing education (13:05) - A cheaper plan is fishing in bad waters (17:38) - Where do your best customers go? (22:25) - Nobody knows interactive video exists (27:20) - Making videos for customers as a service (34:21) - Certification partners: the SOC 2 case (45:38) - Win certifiers who want to stand out (54:18) - Content marketing: teach better videos (01:00:25) - 90-day plan: interview your customers (01:04:47) - Box-tickers vs. buyers who really care (01:07:15) - Energized, with...

E09 w/ Jon Sturgeon: AI changed his agency's model. Should he grow or sell?

1 hr 54 min

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 articlesTwitter | LinkedIn ==========================STARRING MARIO PESHEV==========================DevriXPersonal siteNewsletterTwitter | LinkedIn ================================WITH COHOST JON STURGEON================================Dingus & Zazzyuhoh.com (an IT company for businesses that don’t have IT problems)NewsletterTwitter | LinkedIn ===============================REFERENCED IN THIS EPISODE===============================“The Effortless Experience”—Dixon, Toman & DeLisiHypergen, 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

E08: Creating customer interview questions before you have customers

1 hr 1 min

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 articlesTwitter | LinkedIn STARRING RISON SIMONPainPointyBlogSubstackTwitter | LinkedIn REFERENCED IN THIS EPISODEThe Iterative Hypothesis MethodAI 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

E07 w/ Dan Martell: 1 big logo won't get him the next 10

1 hr 8 min

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 YouTubeGet my bookMy bio + 20 years of articlesTwitter | LinkedIn =======================STARRING GEORGE PALADICHUK=======================NaiLGeorge's siteLinkedInYouTube =======================WITH COHOST DAN MARTELL=======================Dan MartellGrowth Stacking Show (podcast)Martell Method (newsletter)YouTubehttps://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

E06 w/ Bryce Adams: Pivoting his strategy into his strengths

1 hr 41 min

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 articlesTwitter | LinkedIn STARRING CARL ALEXANDERYmirYmir ReportsBlogTwitter | LinkedIn WITH COHOST BRYCE ADAMSMetorikTwitter 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 $1,0...

E05 w/ Laura Roeder: Scared to commit to his best customers

2 hr 1 min

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 articlesTwitter | LinkedIn STARRING HASAN CAGLIPostPlanifyTwitter | LinkedInYouTube WITH COHOST LAURA ROEDERFounder at PaperbellRead her blog atTwitter 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)...

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

1 hr 56 min

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 articlesTwitter | LinkedIn STARRING PATRIK INZINGERappointmedHomepageSlow & Steady newsletterTwitter | LinkedIn | Bluesky WITH COHOST DR. SHERRY WALLINGZenFounderExit 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

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

2 hr 30 min

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 articlesTwitter | LinkedIn STARRING TIAGO FERREIRA & JOÃO AMARO PodsqueezeTiago's podcast, Indie FounderTwitter | LinkedInTwitter | LinkedIn WITH COHOST CRAIG HEWITT   CastosMore About CraigRogue Startups podcastTwitter | 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...

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

2 hr 14 min

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 articlesTwitter | LinkedIn ==========================STARRING JESSE SCHOBERG==========================DropInBlogHomepageTwitter | LinkedIn ==========================WITH COHOST ROB WALLING==========================All About RobTinySeedMicroConfStartups For the Rest of Us (podcast)The SaaS PlaybookTwitter =============================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 wall5:56 Big companies were visiting his site — and he had nothing to sell them12:17 "Useful" isn't "delight": why nothing in the pitch excites buyers19:27 Going upmarket without wrecking the simple product people love22:19 How to price when a $49 and a $999 plan share one page25:53 Marketing budgets are getting cut — sell them their job back from AI36:43 Marketer or engineer: who actually clicks "book a demo"?45:49 Run ads to discover your message, not for ROI51:19 Stop fishing in the pond you like — go where the best customers are1:04:40 The agency channel: land one, get many customers over time1:14:33 Account-based marketing: courting a few whales for years1:21:20 Run your own event to become the category expert1:28:29 The seven types of SaaS plateau — which...

E01: Restarting growth when stuck at $32K MRR

2 hr 4 min

$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 2...

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