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

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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/

• (00:00:00) - Off-Site Podcast
• (00:00:53) - Mark Zuckerberg In The Dream
• (00:02:15) - Summer Vacation: Where Are You Working?
• (00:02:53) - How to grow a team in Eastern Europe
• (00:09:24) - How to start a support team in the Philippines or Latin America
• (00:13:00) - Drop in Blog: How long have you been doing it?
• (00:14:18) - The New Shopify Homepage
• (00:18:38) - How to make a Framer site in 2 Minutes
• (00:23:04) - Reveal: We're Experimenting With Enterprise Channels
• (00:28:52) - How to Integrate with a Website Platform
• (00:31:02) - IBM on AI Voice Integrations
• (00:37:39) - Jesse Hanley on His New DM
• (00:39:07) - Getting Back on the Board
• (00:41:25) - What Happened at the Oracle Board Meeting
• (00:43:00) - Have You Had To Make Changes At Your Company?
• (00:44:56) - Let's Push the Website Live!
• (00:50:37) - How to get mentioned in AI on LinkedIn
• (00:56:15) - How to Stay Remarkably relevant in an AI World
• (00:58:49) - Jesse on Riffing With Kendrick

What happens when you achieve your goal but lose your purpose?

Jordan Gal sits down with his brother Assaf just two weeks after Assaf closed the sale of his six-location Crunch Fitness franchise empire. After 13 years building a 200-employee operation across Brooklyn, Bronx, and Queens, Assaf shares the emotional reality of transitioning from entrepreneurship to uncertainty. "Every day when you have a thing, you have a North Star, you have a purpose," Assaf reflects. "And now it feels like there's nothing." The conversation explores the ten-month deal process, the weight of managing 200 employees, and the challenge of finding what's next. What does freedom actually feel like when you've spent over a decade grinding? How do you process relief, guilt, and the search for new purpose?

In This Episode:

• (00:00) The Business Sale That Just Closed Two Weeks Ago
• (09:57) From Relief to Emotional Goodbye with 200 Employees
• (14:17) Why Some Exits Don't Feel Like Going to Disneyland
• (19:44) The Invisible Hand of Capital and Which Game You're Playing
• (26:41) Airplanes, Perspective, and Seeing the Bigger Picture
• (36:49) The Ocean of Capital That Needs to Find Returns
• (45:44) Why Everything Has Warts and Nothing Is Perfect
• (48:18) Italy, Tuscany, and Deciding Not to Be in the Race
• 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:

LinkedIn: Assaf Gal https://www.linkedin.com/in/assafgal/

Jordan Gal: https://www.linkedin.com/in/jordangal/
Rosie AI: https://heyrosie.com/

• (00:00:00) - The Search for Destiny
• (00:00:21) - Off-Site Podcast
• (00:01:02) - An Entrepreneur Discusses His Exit
• (00:03:05) - How a Franchisee Became a Crunch Fitness Franchisee
• (00:04:31) - In the Elevator With Entrepreneurs
• (00:07:07) - Have You Got What it Takes to Become a Franchisee?
• (00:09:53) - The Pain of a Deal
• (00:11:15) - Why I Didn't Share My Exit With Anyone
• (00:16:18) - Want to Start a Business? Here You Are
• (00:18:34) - What about the Crunch Fitness Franchise?
• (00:22:36) - Allergic to my scar tissue
• (00:23:14) - Do You Think You Know the Future?
• (00:28:26) - Flying Business on a Plane
• (00:31:02) - In the Elevator With Adam Smith
• (00:32:26) - Franchisee Incentives: Aligning With Management
• (00:35:27) - Steve Jobs on Venture Capital and Software
• (00:41:49) - Ideas for Expansion
• (00:45:37) - Israel Football Player on the World
• (00:49:31) - Jon Favreau on His Time Off
• (00:51:17) - A Week On Vacation With The Team

Is the era of grinding and hustling finally over for smart founders?

Jordan Gal hosts fellow entrepreneur Christian Genco in this candid conversation about the "two wolves" battling inside every founder. Genco, creator of File Inbox and seasoned bootstrapper, brings 12+ years of SaaS experience to discuss the eternal tension between "enough" wealth versus relentless growth. Both founders dig into their personal motivations, from Gal's immigrant drive to "slay the dragon" to Genco's struggle between minimalist philosophy and capitalist ambition. What drives someone to want "millions of dollars post-tax in a personal bank account"? How do you balance family life with business obsession? The conversation reveals the raw psychology behind entrepreneurial success and the frameworks top founders use to navigate major decisions.

In This Episode:

• (00:00) The Two Wolves Inside Every Entrepreneur
• (13:00) Shoveling Coal vs Strategic Thinking
• (23:00) How Fatherhood Changes Business Ambition
• (31:00) File Inbox: The 12-Year Dragon Hunt
• (44:00) AI Revolution in Marketing and Automation
• (52:00) The Era of the Idea Guy
• (59:00) Zuckerberg's Hundred Million Dollar Chess Game
• 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:

Christian Genco: https://x.com/cgenco

File Inbox: fileinbox.com

Jordan Gal: https://www.linkedin.com/in/jordangal/
Rosie AI: https://heyrosie.com/

• (00:00:00) - Off-Site Podcast: The American Wolf
• (00:00:41) - Christian Genko on The First Time He Met Jordan
• (00:01:26) - In the Elevator With Carthook
• (00:04:39) - Why Do I Need a Million-Dollar Budget?
• (00:10:21) - The Workaholic's Challenge
• (00:14:12) - Pushing a Direction Change
• (00:18:49) - Have You Learned to Find Time for Yourself?
• (00:22:59) - How to Limit Yourself to Limited Focus
• (00:27:43) - Having a Team at Work
• (00:31:06) - Slack's Ad Spending Slow Down
• (00:35:50) - How Much Advertising Should We Spend?
• (00:40:12) - Should You Diversify Into Other Channels?
• (00:41:23) - The Bullseye Method for Going To Market
• (00:44:30) - Go to Market: The Claude Model
• (00:50:27) - The Future of SaaS Is in the Ideas
• (00:52:52) - Zuckerberg's OpenAI Battle
• (00:59:20) - Facebook's Next Evolving Paradigm
• (01:02:07) - Drop In: File Inbox
• (01:02:44) - Offsite: Where Everything Clicks