How do you scale when the funnel's already working?

Jordan reunites with Brian Casel of Builder Methods for their biannual check-in. Jordan's pushing Rosie from unichannel to multichannel, adding SMS to phone answering with a bold 5M ARR goal for 2026. Brian's hitting his stride with Builder Methods Pro, where YouTube content fuels his membership business—December already matching November's revenue halfway through. "The funnel is working as it stands today," Brian notes. But he's feeling the pressure: can one platform sustain growth? Both founders tackle the challenge of doubling down on what works while strategically diversifying. What happens when success creates its own constraints?

In This Episode:
(00:00) The Biannual Bootstrapped Web Update Returns

(02:01) Finding Focus Beyond the News Cycle

(07:16) Building With AI: Claude and Cursor Are Game Changers

(23:14) Rosie's Big Leap: From Unichannel to Multichannel

(36:40) The Challenge of Selling Additional Products

(49:30) Builder Methods Growth Strategy for 2026

(54:33) Leveraging YouTube Content Across Multiple Platforms

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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:
Brian Casel: https://x.com/CasJam
Rosie AI: https://heyrosie.com/

• (00:00:00) - Offsite Podcast: The AI Team
• (00:00:40) - Bootstrapped Web
• (00:03:58) - A Year in Review: 2017
• (00:06:36) - Pushing the pivot at Rosie
• (00:10:23) - Rosie: Going Vertical With AI
• (00:11:28) - Reveal: The Pivot
• (00:12:53) - How to Build with AI
• (00:19:50) - How to Build a Website with a Human Interface
• (00:21:15) - Agent OS: The Demand for Software Developers
• (00:24:49) - How to Start a New Business with Builder Methods Pro
• (00:28:26) - Developers' Confidence in the New Future
• (00:33:35) - Building your own tech stack
• (00:39:08) - In the Elevator With Rosie
• (00:41:49) - WSJD Live: Looking Back on 25
• (00:49:01) - How to Build a Business on a YouTube Channel with a 6-
• (00:54:34) - Is YouTube the Anchor for Your Business?
• (00:56:22) - Happy Hanukkah!

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/

• (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

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/

• (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