Smart Bear Live

Jason Cohen
  • 5.0 (2)
  • Entrepreneurship

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

  1. 5 days ago

    E02: DropInBlog: Expanding from $1M ARR, workshopping how to enter 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.  ====================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 one is yours?1:37:07 How to roll out a new strategy without scaring your team1:48:44 Every big bet needs one owner who thinks of nothing else2:04:13 What agencies want more than a kickback

    E02: DropInBlog: Expanding from $1M ARR, workshopping how to enter a new market

  2. 23 Jul

    E01: ScreenshotOne: Restarting growth at $32k/mo using both feelings and metrics

    $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 25 years, both bootstrapped and VC-funded, resulting in two exits and two unicorns (Smart Bear & WP Engine), I've also been writing about everything I know for 18 years. Now I'm making some videos. More about me

    E01: ScreenshotOne: Restarting growth at $32k/mo using both feelings and metrics
  • 2 Episodes

Ratings & Reviews

5
out of 5
2 Ratings

About

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.

Information

  • Creator
    Jason Cohen
  • Years Active
    2026
  • Episodes
    2
  • Rating
    Explicit
  • Copyright
    © 2026 Team Cohen
  • Show Website
    Smart Bear Live