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

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/

• (00:00:00) - Off-Site Podcast
• (00:01:05) - What Are You Up To?
• (00:01:59) - Good Metrics: Complex Products Worth Building
• (00:03:11) - Mark Thomas on How To Boost Startup Marketing
• (00:04:51) - Is AI SEO Even Worth Its Name?
• (00:07:28) - Top of the Filament Content Is Dead in AI SEO
• (00:10:55) - ChatGPT, Meta, and
• (00:13:53) - How to Get People to Pay for Your Startup
• (00:15:05) - Top of the Funnel vs. Bottom of the Filament
• (00:18:22) - How To Get 100% Attribution From Your Analytics Tool
• (00:23:49) - Vibe Coding: Will AI Affect Your Job?
• (00:26:17) - How AI Is Affecting the Workflow of Our Team
• (00:29:51) - How to Come Up With Ideas for the Company
• (00:36:03) - Do We Need a New 'Influencer' Strategy?
• (00:37:18) - In the Elevator With Chris Snappa
• (00:39:19) - We're In A Place Where Nothing Works
• (00:41:35) - How to Market to Facebook, Twitter, and Google Analytics
• (00:43:50) - Paid Acquisition: Should We Stay in or Exit?
• (00:49:49) - Facebook Live: Investing in Bitcoin
• (00:50:35) - How to Travel With a Child
• (00:51:42) - How Active Do You Think About Parenting?
• (00:56:30) - Should I Homeschool or Go to Public School?
• (00:59:36) - PODCAST: The Friendships
• (01:00:14) - Dietrich

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/henrypoydar
Steady:

• (00:00:00) - Off-Site Podcast
• (00:00:49) - How To Parent Your Teenage Son On The Last Day of School
• (00:05:35) - What Parents Need You To Know About Parenting
• (00:09:09) - What Makes a Family Camp?
• (00:12:29) - Good Goals, Good Reasons to Work Hard
• (00:12:42) - San Francisco
• (00:14:54) - Having just relocated from New York to San Francisco,
• (00:18:39) - Living in San Francisco vs. New York
• (00:24:25) - The Hard Job of Running an AI Startup
• (00:27:19) - Amazon's Alexa: The Voice Competitor
• (00:27:47) - In the Elevator With Elon
• (00:31:35) - Tell a Crazy Story
• (00:35:46) - Tell a Story With Your Work
• (00:37:42) - Tellers on Accountability and autonomy
• (00:41:55) - How to Manage a Middle Child
• (00:47:50) - In the Elevator With Rich People
• (00:49:44) - What are you working on right now?
• (00:52:57) - Pricing for Website Software
• (00:54:58) - Is AI Threatening Your Workflow?
• (01:01:37) - The early part of the developer career
• (01:05:05) - Amino on Twitter

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)

• (00:00:00) - Off Site Podcast: Being Candid in Your Marketing
• (00:01:42) - Aaron Rubin on How To Make His Podcast Good
• (00:05:52) - What Are You Working On This Week?
• (00:06:14) - Kevin Wagstaff Bootstrapped a Startup, Then Sold 49%
• (00:08:11) - Seven Startup Ideas I Would Never Build
• (00:10:16) - "My Job Is... Podcasting."
• (00:11:55) - Teaching at Try Hard Studios
• (00:17:26) - In the Elevator With Rob and Anar
• (00:21:18) - Facebook's CEO: The $3 Billion
• (00:21:57) - Bootstrappers: Too Shy, Too Real for Marketing
• (00:24:44) - Don't Attend Board Meetings
• (00:27:34) - Tiny Seed Board Meetings
• (00:33:40) - MicroConf CEO on the Future of the Business
• (00:38:28) - How to Make a Podcast Good
• (00:43:10) - No More Updates on Startups
• (00:46:40) - Does It Hurt to Talk About Your Business?
• (00:47:17) - On Aaron and Jordan's Disclosures