Offsite

Jordan Gal

The Offsite Podcast is a candid, behind-the-scenes catch-up with host Jordan Gal and the friends, founders, and thinkers he admires. Each episode kicks off with real talk about work—what’s hard, what’s going well, and what’s unfolding in the moment. But just as important is what’s going on outside the lines of work: personal growth, ambition, envy, burnout, and the chaos of building while being human. With a rotating cast of co-hosts, the show is as much about chemistry as it is about insight. This is a podcast about making sense of the mess and meaning of modern work and life, without taking ourselves too seriously. Honest updates, sharp takes, and the occasional therapy session, all recorded with a mic, a laugh, and a glass of something nearby. Brought to you by Rosie, the AI-powered phone answering service for small businesses.

  1. Ep 15 - Strategy Session

    NOV 19

    Ep 15 - Strategy Session

    What if charging upfront actually converts better than free trials for your product?    Jordan Gal sits down with Ruben Gamez, founder of SignWell and creator of BidSketch, for a tactical deep dive into SaaS fundamentals. Ruben built two successful products despite never finishing high school—a testament to execution over credentials. Should you charge upfront or offer free trials? The duo dissects data from both their companies, revealing counterintuitive truths about friction and conversion. "Everything that added friction... resulted in just more conversions later," Ruben explains about BidSketch, while SignWell required the opposite approach. They explore the grinding reality of competing in crowded markets, Google's AI disruption of SEO traffic, and Ruben's current transition from operator to owner at his 15-person company. Real strategies, zero fluff. How do you make pricing decisions from confidence instead of fear?    In This Episode:   (00:00) Catching Up with Ruben Gamez  (02:34) Homeschooling in Portland: Academic Excellence vs Public School  (08:56) From BidSketch to SignWell: The Accidental Pivot  (12:22) Ignoring Advice: Why Ruben Built SignWell Anyway  (19:46) Google's AI Disruption: The Future of SEO Traffic  (26:35) The Friction Paradox: When More Steps Increase Conversions  (30:47) Free Trials vs Freemium: What Actually Works  (43:11) Making Business Decisions from Confidence Not Fear  (46:58) Transitioning from CEO to Owner at SignWell  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:  Twitter/X: https://x.com/earthlingworks  SignWell: https://signwell.com  BidSketch: https://bidsketch.com  Rosie AI: https://heyrosie.com/  Chapters (00:00:00) - Google's Ad-Phishing(00:00:34) - Homeschooling and the Oregon Public School System(00:05:30) - How Homeschool is Working for My Kids(00:05:58) - The Social Life of Wall Street(00:08:38) - Pushing the Right Pillow(00:09:04) - Signwall: The Journey From Bizketch to(00:13:23) - How to Get Customers to Use E-Signatures(00:15:14) - In the Elevator With Elon Musk(00:17:23) - Execution has been a challenge(00:19:10) - Is Google Going AI with Search?(00:24:16) - Is Google's AI-based Search Impact on Sites?(00:28:19) - Free Trials and Paid Upgrades(00:34:40) - Facebook Reconsidering The Reverse Trial(00:39:08) - PayPal's 7-(00:43:23) - How To Build a More Confident Business With Bit Sketch(00:46:53) - SignWall CEO on Transition From CEO to Owner(00:49:41) - Boogie Island

    50 min
  2. Ep 14 - Culture Shock

    NOV 12

    Ep 14 - Culture Shock

    Are you building a business that fits your personality or following someone else's playbook?    Jordan Gal hosts Jon Ewalt, founder of Roaster Tools, a comprehensive ERP system built specifically for specialty coffee roasters. After selling his Portland coffee roastery, Jon dove into software development nine years ago and has been "playing catch up" ever since. Now based in San Miguel de Allende, Mexico, Jon discusses the challenges of building desktop software with long development cycles while prioritizing personal time alongside business growth. How do you balance sustainable business practices with ambitious goals? Jordan and Jon explore the reality of mid-40s entrepreneurship, the value of a tight-knit founder community, and why Jon chose to move his family to Mexico for immersion Spanish education. Their decade-long friendship offers insights into building businesses aligned with your personality rather than chasing hockey stick growth.    In This Episode:   (00:00) From Coffee Roaster to Software Founder  (01:39) Why We Moved Our Families to Different Countries  (04:23) The Immigrant Experience and Core Memories  (09:30) Launching Too Early: Playing Catch Up for Nine Years  (18:45) Building Desktop Software vs Web Apps  (25:30) The Founder Mastermind That Predicted Our Paths  (33:56) Mid-40s and the Question of What's Next  (38:21) Moving Up the Abstraction Layer in Business  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:    Jon Ewalt LinkedIn: https://www.linkedin.com/in/jonewalt/  Roaster Tools: https://www.roastertools.com/  Rosie AI: https://heyrosie.com/    Chapters (00:00:00) - Off-Site Podcast: The Place of Work(00:00:59) - Living as a Non-American in Mexico(00:06:19) - How To Raise An Immigrant Child(00:09:00) - How to Run a Coffee Company for 10 Years(00:13:03) - Tyler and Jordan on Their Differences(00:18:48) - Top Software Executives: How Do You Manage Your Team(00:25:19) - Roaster Company's Big Features(00:30:53) - Have You Had Any Negative Feedback From Your Partners?(00:33:09) - A Slack Group For Old People(00:38:52) - Have You Reached a Point Where You Can Exit Your Business?(00:39:59) - A Taste of Mexican food

    41 min
  3. Ep 13 - Set the Mood

    NOV 5

    Ep 13 - Set the Mood

    Are you selling AI solutions or business outcomes? (One makes money, one doesn't.)    Jordan Gal hosts Craig Hewitt, founder of Castos and an AI content creator deep into his "100 Days of AI" project, alongside Chris Gimmer, co-founder of Fathom Analytics who just launched Good Metrics, a privacy-first analytics platform. Should OpenAI go public at a trillion dollars? The trio debates whether we're witnessing a bubble or the beginning of something bigger. Craig reveals why ChatGPT is "the worst AI tool" for his work—blasphemy or insight? Chris shares the painful decision to delay his launch for months after infrastructure issues. They tackle working from home versus office space, the coming wave of household robots, and why selling AI solutions directly might be the wrong approach. When will you have a robot in your house?    In This Episode:   (00:00) Music, Mood, and Getting Into Work Mode  (06:05) The Work From Home Versus Office Debate  (12:32) OpenAI Going Public at a Trillion Dollars  (20:09) Craig's 100 Days of AI and Why ChatGPT Isn't the Best  (26:29) Chris Launches Good Metrics After Infrastructure Delays  (34:56) When Will You Have a Robot in Your House?  (35:33) Selling AI Solutions Versus Selling Business Outcomes  (42:54) Vibe Running Your Company and Analytics Reality  (48:10) Multi-Channel Attribution and Why Data Is Always Fuzzy  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 - Twitter/X: https://x.com/TheCraigHewitt  Chris Gimmer - Twitter/X: https://x.com/cgimmer  Rosie AI: https://heyrosie.com/  Chapters (00:00:00) - The Off-Site Podcast(00:00:44) - Off-Site Podcast(00:01:05) - What Kind Of Music Do You Listen To While Working?(00:06:05) - Working From Home(00:10:30) - Have You Really Need An Office?(00:12:32) - OpenAI Is Considering Going Public(00:14:34) - Semiconductor Bubble: Can We Still Ride It?(00:19:45) - ChatGPT: The Worst AI Tool in the Market(00:22:15) - ChatGPT vs. Google Sheets: The Race for AI(00:25:13) - Clickhouse's Early-Access Launch(00:26:32) - Facebook to Offer Early Access to its Website(00:27:39) - Rosie: Do We Just Launch the Product?(00:32:47) - Startups: First Impressions(00:34:56) - Are You Ready for Your Robot Home?(00:35:29) - Chris: Should I Do a Case Study on AI Agents?(00:41:11) - Will Businesses Integrate AI Into Their Analytics?(00:48:10) - How To Tell Where New Customers Are Coming From?

    52 min
  4. Envy Fuel

    OCT 29

    Envy Fuel

    Could sharing your most shameful moment actually accelerate your career?    Jordan Gal teams up with fellow entrepreneurs to discuss work and life beyond business. In this episode, Jordan sits down with returning guest Christian Genco,a software engineer and entrepreneur navigating the challenges of scaling products while maintaining focus. Christian recently welcomed his second child and shares insights on balancing creative work with reactive demands. What's the real cost of constant interruptions on engineering productivity? The conversation explores vulnerability as a business asset, the concept of "Sanskara" (emotional wounds from Sanskrit that block growth), and practical strategies from 37signals' Shape Up methodology. Christian opens up about getting fired from a startup and how sharing that vulnerability created unexpected opportunities. Can founders really separate engineering focus from customer chaos?    In This Episode:     (00:00) How Sharing Shame Creates Unexpected Business Opportunities  (05:48) Christian Announces His Second Child  (13:52) The Creative Satisfaction Problem in Business  (24:52) Managing Reactive Engineering vs Deep Creative Work  (42:19) Founder Intentions and Life Philosophy Beyond Money  (56:22) The Engineering Productivity Challenge Every Startup Faces  (59:37) 37signals' Approach to Protecting Engineering Focus  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 X: https://x.com/cgenco    37signals (company) - basecamp.com Rosie AI: https://heyrosie.com/  Chapters (00:00:00) - Off-Site Podcast(00:01:52) - Why I Talk About My Mistakes on My Podcast(00:05:48) - Baby Luca's First Birthday(00:08:39) - What Do You Need To Know For A 3-Year-Old(00:10:54) - Has Having a Baby Impact Your Worklife?(00:14:40) - Sponsoring an AI startup(00:15:05) - How to Focus On Work and Family(00:16:50) - "You Ruined My Wedding!"(00:18:46) - How to Stop Reacting to Customer Support Emails(00:23:51) - Patrick Collison on His Personal(00:28:28) - The Secret to A Nice House(00:31:10) - How to Let Go Of Envy(00:34:47) - "I Can't Control My Own Life"(00:38:12) - The Lean Startup on Postmortem(00:42:42) - A Boss Had a Fight With His Employee Over Communication(00:47:32) - How To Deal With Conflict In Your Relationship(00:51:03) - How to Manage Expectations in the Software Development Process(00:56:30) - How to Manage a Non-Technical Team(00:59:37) - Software Development: The Hill Chart

    1h 2m
  5. Two Different Approaches

    OCT 22

    Two Different Approaches

    Could a single technical person who enjoys talking to customers really build a ten million dollar business alone?    Host Jordan Gal sits down with Jesse Hanley, founder of Bento, an email marketing platform, for an exploration of contrasting entrepreneurial approaches. Jesse operates solo from Fukuoka, Japan, building Bento into a single-digit-millions business through patience and deliberate choices. What drives a founder to stay lean while his company scales? The conversation traces back to 2012 when Jordan first met Jesse during his supplement store days, revealing how both founders evolved from those scrappy beginnings. They dissect everything from the arbitrage of living abroad to managing investor expectations versus staying bootstrap. Jesse's commitment to doing support on Twitter after years in business isn't masochism—it's strategy.    In This Episode:   (00:00) How Jordan and Jesse First Connected in 2012  (08:41) Why 2015 Was a Unique Era for Building Products  (10:18) Building Bento Through Grief and Finding Focus  (13:15) The Reality of Living and Working in Japan  (16:04) Customer Support as Long-Term Reputation Building  (24:07) Living Without Financial Goals or Ambition  (29:00) The Evolving Email Marketing Landscape  (42:29) Staying Solo While Scaling to Millions  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 Hanley: https://x.com/jessethanley    Jordan Gal: https://www.linkedin.com/in/jordangal/  Rosie AI: https://heyrosie.com/  Chapters (00:00:00) - Crazy Start to Cardhook(00:04:04) - Ron Wright on The Right to Travel(00:04:24) - Cardhook on Full-Page Payout(00:05:55) - In the Elevator of the 2015s(00:08:41) - In the Elevator With Bento(00:10:49) - Living in Japan(00:13:45) - The Patience of a Startup Founder(00:19:55) - How to Live a Happy Life(00:20:13) - How Much of an Impact Does Your Environment Have on You?(00:23:56) - Bento CEO on Working On His Own Email(00:29:07) - Marketing and Email: The Future of Email(00:34:39) - Have you considered doing letter drops?(00:36:05) - Where's the Company's Growth Coming From?(00:40:47) - The Paying Channel Challenge(00:42:13) - Bento on the Challenges(00:46:59) - Rosie Is to Mailchimp as Klaviyo Is(00:50:16) - What is your day to day?(00:52:31) - On Managing the Company(00:55:19) - Ideas for hiring a full-time employee(01:00:19) - How To Build a Software Company With Just One Person(01:03:10) - Six is a great team size for startups(01:08:10) - Bento on Managing Investor Expectations(01:13:40) - In the Elevator With Steve Jobs(01:14:03) - Priority Stack vs Valuation(01:19:47) - Catching up with Steve Jobs

    1h 21m
  6. Our Cake and Eat It Too

    SEP 24

    Our Cake and Eat It Too

    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/ Chapters (00:00:00) - Off-Site Podcast: When You Should Have Started a Business(00:00:45) - Steve Jobs on Working in the Summer(00:01:33) - On The Drop Off of Kids(00:04:25) - Coming soon: The Balance Between Work and Family(00:08:31) - How We're Redoing Our Minutes Onboarding(00:13:46) - The Secret to Good Trials(00:15:29) - The Value of Out-Of-Office Training(00:18:44) - How to Start a Business With a Baby(00:20:39) - Management Persona 6: Stories for Collaboration(00:25:22) - Reasons We're Optimizing Pricing(00:31:31) - What Is the Leverage of Your Business?(00:35:27) - Are You Still Using Agents in Your Sales?(00:37:32) - The Percentage of AI Pilots Are Failing(00:39:17) - What is an AI Agent?(00:40:46) - Pilots: The Need to Connect With Your Team(00:44:40) - Initiating AI in the Workforce(00:47:45) - Reaching Out to Your Customers(00:52:28) - How to Build a Million-Revenue Startup with a Marketing Plan(00:57:05) - Separation of Marketing and Integrations

    1h 1m
  7. Get Some Sleep

    SEP 18

    Get Some Sleep

    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/cgenco Jordan Gal: https://www.linkedin.com/in/jordangal/ Rosie AI: https://heyrosie.com/ Chapters (00:00:00) - Small Business Offsite: A Legacy Company vs. a Small Business(00:00:57) - How To Pronounce Christian's Last Name(00:01:31) - A string of good days for Andy(00:01:54) - Sleep Quality Improvement(00:06:38) - Workaholics on a Desk(00:11:49) - How Do You Contain The News Cycle(00:16:14) - Work Is a Sanctuary for Political Discussions(00:20:35) - Philosophically, The Separate spheres(00:24:36) - Feeling more involved in the company's culture(00:28:40) - WSJD Live: Revenue growth is lagging(00:34:44) - Tim Ferriss on His Team(00:35:08) - How to Manage People On a Solo Company(00:44:33) - How to Build a Virtual Sales Team(00:50:08) - How To Design a Lead List for Wetransfer(00:56:41) - How to Find the Right Message for Your Customers(01:00:17) - How to Build a Strategic Survey(01:03:41) - Should You Be Able To Carry A Concealed Pistol?(01:05:59) - Happy Holidays!

    1h 6m
  8. Good Stress

    SEP 10

    Good Stress

    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/ Chapters (00:00:00) - The most important thing on YouTube(00:00:20) - Off-Site Podcast: How To Get Out Of Recession(00:03:20) - What is it about stress in the year?(00:06:09) - Summer Business: Will It Slow Down?(00:08:25) - How to Send More Emails(00:12:13) - How To Avoid Legal Issues With Text Messages(00:14:25) - How to Do a Podcast and a Video Every Day(00:18:17) - How To Make a Video on YouTube(00:20:59) - How to Make a Scriptment on Screen(00:22:04) - Jordan on Making His Own Ad(00:24:00) - The Competition in AI Voice(00:29:17) - How to Get More Out of Content Marketing than B2C Marketing(00:31:36) - How to Cheat at AI-based Deals(00:33:50) - Kastos Integrations: The Right Partner for AI?(00:39:14) - Onboarding and the Drop Off Points(00:40:57) - A Hundred Day Project: Building an Audience(00:42:20) - B2B AI Training(00:46:34) - The Future of Small Law Firms(00:49:19) - How to Build a Billion-Dollar Business With AI

    52 min

About

The Offsite Podcast is a candid, behind-the-scenes catch-up with host Jordan Gal and the friends, founders, and thinkers he admires. Each episode kicks off with real talk about work—what’s hard, what’s going well, and what’s unfolding in the moment. But just as important is what’s going on outside the lines of work: personal growth, ambition, envy, burnout, and the chaos of building while being human. With a rotating cast of co-hosts, the show is as much about chemistry as it is about insight. This is a podcast about making sense of the mess and meaning of modern work and life, without taking ourselves too seriously. Honest updates, sharp takes, and the occasional therapy session, all recorded with a mic, a laugh, and a glass of something nearby. Brought to you by Rosie, the AI-powered phone answering service for small businesses.