Is the "bootstrap or die" mentality actually killing your business growth potential?

Jordan Gal hosts entrepreneur Jesse Schoberg, co-founder of Drop-In Blog, a headless blogging platform that seamlessly integrates blogs into existing websites. Jesse, a nomadic founder currently between Bangkok and Europe, shares his journey from bootstrap mentality to embracing enterprise sales. After hitting a growth plateau at seven figures, Drop-In Blog pivoted their positioning and hired full-time marketing staff in Eastern Europe. "After a plateau for about a year, all of a sudden doing a demo doesn't sound so bad," Jesse admits, about his evolution from credit-cards-only to enterprise contracts. The conversation explores remote team building, the global talent arbitrage, and how Jesse discovered AI-powered SEO as their hook for LinkedIn growth. How do founders know when it's time to abandon their original playbook?

In This Episode:

(00:00) Mark Zuckerberg Yacht Dreams and Global Nomad Life

(02:38) Building Remote Teams in Eastern Europe vs America

(06:38) The White Collar Manufacturing Revolution

(14:34) Drop-In Blog Business Model and 10-Year Journey

(25:02) Hitting the Seven Figure Growth Plateau

(31:02) The Integrations Game and Partnership Strategy

(39:05) Board Meetings and Business Accountability Systems

(50:03) From Bootstrap Mentality to Enterprise Sales

(55:21) AI SEO Strategy and Getting Mentioned by ChatGPT

Share with someone who would benefit, like and subscribe to hear all of our future episodes!

About the Show

Jordan Gal, founder and CEO of Rosie AI, hosts the Offsite Podcast where he teams up with rotating entrepreneur friends to explore what's happening in their work and beyond. After successfully building and selling CartHook, Jordan now leads a VC-backed company while sharing candid insights about the realities of startup life. The show combines real-time business updates with deeper conversations about founder psychology, growth strategies, and the personal side of entrepreneurship that rarely gets discussed publicly.

Resources:
Jesse Schoberg: https://x.com/JesseSchoberg
Jordan Gal: https://www.linkedin.com/in/jordangal/
Rosie AI: https://heyrosie.com/

#1105 - The Moral Madness of Atheism

The Counsel of Trent

A Modest Moral Argument Proposal

The AI-powered Podcast Player