What price are entrepreneurs willing to pay for presence?  Jordan Gal, founder and host of Offsite, reconnects with Henry Poydar, CEO of Steady, to discuss the personal and professional transitions of being an empty nester entrepreneur. Henry, who recently dropped off his twin boys at college, reflects on the emotional journey while pivoting Steady from a per-user pricing model to team-based pricing for their AI copilot for teamwork. "You get 18 summers with your kids, and then it's over," Henry shares about the transition. The conversation explores how both founders chose entrepreneurship precisely for family flexibility, with Jordan questioning whether true work-life balance exists or if it's about accepting trade-offs.   In This Episode:   (00:00) Empty Nester Entrepreneur Reality  (05:53) The Entrepreneurial Path to Family Balance  (08:25) Trading Career Greatness for Presence  (12:05) Rosie's Seven-Day Trial Strategy Shift  (18:36) The Psychology of Phone Coverage  (25:21) Steady's Team-Based Pricing Revolution  (33:04) Building Customer Advisory Relationships  (42:59) Pilots vs Trials in Enterprise Sales  (54:02) SimpliSafe Marketing Masterclass  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: Henry Poydar Twitter: https://x.com/henrypoydar Steady AI: https://steady.app Tiny Seed accelerator: https://tinyseed.com MicroConf conference: https://microconf.com Jordan Gal: https://www.linkedin.com/in/jordangal/ Rosie AI: https://heyrosie.com/

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/

What's the real reason traditional SEO and content marketing are dead?  Jordan chats with Chris Gimmer, who's bootstrapping GoodMetrics.io and co-founded Snappa.com, and Craig Hewitt, CEO of Castos podcasting platform, about the current state of customer acquisition. Gimmer explains building Good Metrics as an alternative to Google Analytics, while Hewitt reveals how hiring marketer Mark Thomas increased trials by 30%.   The conversation digs into AI's impact on marketing automation, with Gimmer noting that Python scripts can identify potential customers on Twitter and Reddit. "Nothing is working for us" in terms of new acquisition channels, admits Hewitt. How are seasoned entrepreneurs adapting their strategies when traditional marketing playbooks fail? The trio also discusses AI-powered SEO strategies and the challenges of scaling beyond paid advertising in today's saturated market.   In This Episode:     (00:00) Welcome and Introductions - What Are You Working On?  (01:16) Chris Gimmer's Good Metrics Beta Launch Journey  (03:11) Craig Hewitt's 30% Trial Increase with Strategic Marketing  (05:20) The Future of AI SEO and Content Distribution  (12:41) Why Nothing Works in Customer Acquisition Anymore  (24:04) Vibe Coding and AI Automation for Lead Generation  (40:04) The Reality of Building Without Traditional Channels  (50:35) Parenting as Entrepreneur Fathers - Travel and Life Balance  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:   Christopher Gimmer: https://x.com/cgimmer  Craig Hewitt: https://x.com/TheCraigHewitt  Jordan Gal: https://www.linkedin.com/in/jordangal/ Rosie AI: https://heyrosie.com/ 

What if the greatest human technology isn't AI or the internet, but something much simpler?Host Jordan Gal welcomes serial entrepreneur Henry Poydar, founder and CEO of Steady, an AI-powered coordination intelligence platform. Henry has had extensive experience with multiple exits and backing from notable investors, including the founder of Red Hat. The conversation explores Henry's philosophy that "the greatest human technology is a story" and his belief that authentic storytelling must never drift between personal, investor, and sales narratives. What makes storytelling so crucial for entrepreneurs? How do you maintain authenticity while scaling your message? The discussion spans personal reflections on parenting and family dynamics to deep dives into AI pricing models, competitive positioning, and the challenges of category creation. Henry shares insights on building high-performing remote teams through trust, shared context, and balanced autonomy. Topics include the evolution of San Francisco's tech culture, the tension between outcome-based versus user-based pricing in AI, and concerns about career paths in an increasingly automated world. Jordan and Henry examine how middle children develop natural storytelling abilities and debate the future impact of AI on entry-level careers. In This Episode:    (00:00) The Greatest Human Technology Is A Story (12:42) San Francisco's Tech Culture Transformation (20:24) Competing Like New York Bankers in Silicon Valley (28:23) Where Are You in Your Storytelling Journey (35:03) Creating Shared Context for Remote Teams (43:01) Middle Child Dynamics and Natural Storytelling (50:16) Pricing Challenges in the AI Era (57:40) Labor Replacement and the Future of Careers (1:01:40) Learning to Think vs Rote Memorization (1:03:17) This Is Water and Reaching for the Stars 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: Henry Poydar: https://x.com/henrypoydarSteady:

How do you balance honesty with effective marketing in 2025?  Welcome to the inaugural episode of the Offsite podcast. Host Jordan Gal, founder of Rosie AI, teams up with seasoned entrepreneurs Rob Walling and Aaron Francis for our first episode. Rob Walling, founder of TinySeed and host of Startups for the Rest of Us, brings 15 years of podcasting experience and deep SaaS expertise. Aaron Francis runs Try Hard Studios and co-hosts Mostly Technical, focusing on screencast education and course creation. Both guests offer contrasting perspectives on building sustainable businesses - Rob through his venture fund and content empire, Aaron through his personality-driven education business.   The trio dives deep into the realities of running different business models, from Jordan's VC-backed growth strategy to Aaron's bootstrapped course business to Rob's venture fund operations. They explore the psychological challenges of founder life, including comparison traps and social media facades. "What I find myself and others like yourselves is that it does hold us back in our marketing because we are too shy, too real, too careful," Jordan observes. How do successful entrepreneurs balance authenticity with effective marketing? What's the real difference between income-focused and outcome-focused business strategies?   In This Episode:     (00:00) Welcome to the Offsite Podcast  (01:13) How Rob Walling Helped Jordan Break Into Tech  (06:14) What Rob and Aaron Are Working on This Week  (14:18) The Psychology of Comparison and Competition  (21:57) Why Authenticity Can Hold Back Your Marketing  (24:49) Jordan's Board Meeting Experience as a VC-Backed Founder  (32:04) The Challenge of Running Non-SaaS Business Models  (38:31) How to Make a Podcast Good - Expert Advice  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:   Rob: https://x.com/robwalling  Aaron: https://x.com/aarondfrancis  Jordan Gal: https://www.linkedin.com/in/jordangal/ Rosie AI: https://heyrosie.com/ Startups for the Rest of Us Podcast (Rob Walling)  Mostly Technical Podcast (Aaron Francis & Ian Landsman)