Offsite

Craig Hewitt, founder of Castos and creator of the "100 Days of AI" project, joins Chris Gimmer, co-founder of Fathom Analytics and founder of Good Metrics. They debate whether OpenAI should go public at a trillion-dollar valuation and discuss the implications of AI solutions versus selling tangible business outcomes. Craig shares why he believes ChatGPT is the worst AI tool for certain tasks. They also explore infrastructure challenges in product launches and ponder the timeline for household robots becoming a reality.

Christian Genco, a software engineer and entrepreneur behind FileInbox, discusses the intersections of vulnerability and business during his insightful chat. He shares how admitting shameful moments, like getting fired, can lead to unexpected opportunities. Christian reflects on balancing work with family life, especially after welcoming his second child. The conversation dives into the challenges of engineering productivity amid constant interruptions and explores the emotional concept of 'Sanskara,' and how it can block personal growth.

In a thought-provoking chat, Jesse Hanley, the founder of Bento, shares his unique approach to building a multi-million dollar email marketing business as a solo operator from Fukuoka, Japan. He discusses the emotional journey of building Bento through personal grief and the strategic importance of customer support on social media. The conversation also covers living abroad, financial arbitrage, and the evolving email marketing landscape, while emphasizing the power of patience and reputation-building in entrepreneurship.

Henry Poydar, CEO of Steady and builder of an AI copilot for teamwork, shares insights on personal and professional transitions as an empty nester after dropping off his twins at college. He discusses the emotional journey of entrepreneurship and how it offers family flexibility. Henry dives into business strategies, advocating for team-based pricing over per-user models, and the importance of customer feedback in shaping products. He also shares innovative trial strategies to improve user engagement and highlights challenges in scaling AI tools for teamwork.

Are you still hiring humans when AI could 10x your output for a fraction of the cost?Jordan Gal hosts entrepreneur Christian Genco on the Offsite podcast, where they dive deep into optimizing personal performance for business success. Christian, a solo developer building File Inbox, shares his recent breakthrough with sleep onset insomnia through a carefully crafted supplement cocktail including melatonin and creatine. "I can create these tools now where I'm hunting," Christian explains about his transition from managing human teams to leveraging AI agents for development work. The conversation explores how small, nimble companies can demand extreme leverage through AI while legacy Fortune 100 companies struggle with outdated processes. How do entrepreneurs maintain focus during chaotic news cycles while building sanctuary spaces for meaningful work? In This Episode: (00:00) Sleep Onset Insomnia and Supplement Solutions (08:54) Creating Human Movement in Digital Work (12:00) Managing News Cycles and Mental Health (18:11) Building Work Sanctuary Spaces (24:43) Team Dynamics and Growth Velocity (34:03) AI Replacing Traditional Business Teams (46:09) Demanding Extreme Leverage from AI Tools (50:20) Direct Outreach Strategy for Competitor Customers 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/cgencoJordan Gal: https://www.linkedin.com/in/jordangal/Rosie AI: https://heyrosie.com/

Jordan Gal hosts Craig Hewitt, founder of Castos, in a raw conversation about entrepreneurial stress and competition. Craig's deep expertise in podcasting and YouTube content creation shines as he shares his "100 Days of AI" experiment—publishing daily videos to build authority in the AI space. The discussion reveals how both founders are pivoting from traditional SaaS playbooks toward distribution-first strategies. "The most important thing on YouTube is the packaging," Craig explains, detailing his shift from $19/month models to higher-value consulting. They explore AI tools like Manus for scaling outreach and debate whether conventional marketing still works. How do you compete when everyone has access to the same AI tools?   In This Episode:    (00:00) Better Than Yesterday But Still Stressed  (04:10) The Great Lock-In of September to December 2025  (08:57) Email Marketing Project with Mark Thomas  (15:46) YouTube Strategy and the 100 Days of AI Experiment  (26:10) Confronting the Reality of AI Competition  (36:05) Building Integrations in Hours with Claude Agents  (46:01) The Opportunity in Corporate AI Training  (53:20) Positioning for the Coming Job Market Disruption  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: Craig Hewitt: https://x.com/TheCraigHewitt Jordan Gal: https://www.linkedin.com/in/jordangal/ Rosie AI: https://heyrosie.com/

Should you build your audience before you build your product?  Jordan Gal reconnects with Brian Casel for their first Bootstrapped Web reunion in eight months, diving deep into the realities of scaling SaaS businesses. Jordan shares Rosie's rapid growth to $1M ARR in eight months, followed by painful plateau challenges when advertising optimization went wrong. "Bad data is worse than no data," he reflects on lessons learned from over-relying on analytics. Brian discusses his pivot to Builder Methods, a creator-first approach focusing on building with AI, growing his YouTube channel from 2,000 to 12,000 subscribers. How do you balance YouTube content creation with monetization? Both founders explore the tension between data-driven decisions and gut instincts while building sustainable, profitable businesses.   In This Episode:   (00:00) Catching Up After Eight Months Apart  (05:33) Croatia Travel and European Vacation Wisdom  (10:31) Mixed Results and Growth Challenges in 2025  (16:00) When Advertising Data Leads You Astray  (25:05) The Creator-First Approach to Building Business  (35:15) YouTube Growth from 2,000 to 12,000 Subscribers  (46:50) Finding Product-Market Fit Through Customer Stories  (58:19) Surveys and Data Collection Strategies  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: Brian Casel: https://x.com/CasJam Jordan Gal: https://www.linkedin.com/in/jordangal/ Rosie AI: https://heyrosie.com/

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/  

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/

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/