E02 w/ Rob Walling: $1M ARR, how to expand into 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.
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ME ME ME!!!
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Subscribe on YouTube (youtube.com/@asmartbear)
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STARRING JESSE SCHOBERG
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DropInBlog (dropinblog.com)
Homepage (schoberg.net)
Twitter (twitter.com/JesseSchoberg) | LinkedIn (linkedin.com/in/schoberg)
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WITH COHOST ROB WALLING
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All About Rob (robwalling.com)
TinySeed (tinyseed.com)
MicroConf (microconf.com)
Startups For the Rest of Us (podcast) (startupsfortherestofus.com)
The SaaS Playbook (saasplaybook.com)
Twitter (twitter.com/robwalling)
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REFERENCED IN THIS EPISODE
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"Max MRR: Your growth ceiling" (longform.asmartbear.com/max-mrr)
"The Elephant Curve & the myth of exponential growth" (longform.asmartbear.com/exponential-growth)
"The Seven Types of SaaS Plateaus" — Rob Walling, MicroConf talk (youtube.com/watch?v=Sv1IO5mmTKY)
"How to Get Mentioned in ChatGPT (Data from 2,000 Sites)" — Jesse Schoberg, MicroConf talk (youtube.com/watch?v=Nyq38GvRm44)
"The SaaS Playbook" — Rob Walling's book (saasplaybook.com)
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