Smart Bear Live

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

Jason Cohen — Sun, 06 Sep 2026 02:00:00 -0500

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
Founder at Paperbell
Read her blog at
Twitter

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) - Closing line: go niche down without fear

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

Jason Cohen — Sun, 30 Aug 2026 02:00:00 -0500

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 | LinkedIn

STARRING PATRIK INZINGER
appointmed
Homepage
Slow & Steady newsletter
Twitter | LinkedIn | Bluesky

WITH COHOST DR. SHERRY WALLING
ZenFounder
Exit 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

Jason Cohen — Sun, 23 Aug 2026 07:00:00 -0500

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
Twitter | LinkedIn

WITH COHOST CRAIG HEWITT
Castos
More About Craig
Rogue Startups podcast
Twitter | 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 beats best-in-class
(01:52:07) - A homepage that's a mess because it talks to everyone
(01:55:45) - The 500K offer they turned down: sell or double down?
(02:02:16) - AI should kill the busy work, not make the content
(02:18:42) - What your SEO traffic is actually worth
(02:26:22) - Stuck in a bad market, and the path to a better one

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

Jason Cohen — Sun, 16 Aug 2026 01:00:00 -0500

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

E01: Restarting growth when stuck at $32K MRR

Jason Cohen — Thu, 23 Jul 2026 13:45:44 -0500

$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