Smart Bear Live

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

Smart Bear Live

Show Notes

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

More from Smart Bear Live

Oct 18, 2026

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 ================================== WITH COHOST JESSICA MALNIK ================================== Homepage Subscribe on Newsletter Subscribe on YouTube The Remote Work Tribe Twitter | LinkedIn ================================ REFERENCED IN THIS EPISODE ================================ “The Iterative-Hypothesis customer development method” “Not Business Advice” books—Alex West TIMESTAMPS

Oct 4, 2026

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

Sep 27, 2026

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

Sep 20, 2026

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

Sep 13, 2026

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

See all episodes →