Titans of SaaS – Details, episodes & analysis

Roby Peñacastro was a broke DJ in a mariachi suit touring Europe when he stumbled into the tech world. After landing a job at Google, he started a side project in his parents’ garage to help his brother manage WhatsApp leads. That side project became Leadsales - a conversational commerce platform now doing $3.7M ARR and backed by Silicon Valley’s SkyDeck accelerator. In this episode, Roby shares how he went from bootstrapping the MVP on credit cards to pitching on Shark Tank Mexico, reducing churn from 30% to 4%, and building a SaaS company with global ambition - all from a small town in Mexico.

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Timestamps

00:00 – Meet Roby Peñacastro

04:46 – Why He Left College and Landed a Job at Google

07:24 – The Side Project That Started in His Parents’ Garage

10:11 – Getting His First Customer for $83

11:06 – Bootstrapping with Credit Cards and Bonuses

13:37 – The Co-Founder Who Quit on the Spot After a Single Demo

16:23 – Leaving Google and Taking the Leap

17:18 – Getting Into SkyDeck with Just Two Months of Runway

19:10 – From Shark Tank Mexico to $3.7M ARR

27:28 – Success Leaves Clues: Betting Big on Retention Over Growth

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Join 30,000+ founders to get exclusive insights and tactics every week with the SaaS Summit newsletter: www.saasacademy.com/jointhesummit

Where to find Johnny Page

➤ LinkedIn: https://www.linkedin.com/in/johnnypage/

➤ Instagram: https://www.instagram.com/johnnypage13/

➤ YouTube: https://www.youtube.com/@johnnypage1/

➤ Website: https://www.thejohnnypage.com/

Where to find Titans of SaaS

➤ Instagram: https://www.instagram.com/titansofsaas/

➤ YouTube: https://www.youtube.com/@titansofsaas/

➤ Website: https://www.saasacademy.com/podcast/

What do you do when you get fired from the company you built? Cody Barbo, founder and CEO of Trust & Will, turned that moment into fuel. In this episode, Cody shares the rollercoaster path from losing his startup to building a nine-figure SaaS company that’s rewriting estate planning across the U.S. You’ll hear how a coffee chat sparked the idea, how Cody and his co-founders lobbied 13 states to change the law, and how they grew from $0 to millions in ARR - all without a legal background. If you’ve ever doubted your ability to bounce back, build big, or break into a “boring” industry, this one’s for you.

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Timestamps

00:00 – Meet Cody Barbo

01:36 – Two Failed Startups and a Firing That Changed Everything

04:45 – Rebuilding From Rock Bottom (And Going Viral Doing It)

06:19 – The Coffee Conversation That Sparked Trust & Will

08:22 – Launching a Legal Tech Company With Zero Legal Experience

10:45 – Why They Had to Change State Laws to Succeed

13:03 – The Early Growth Playbook: Micro-Influencers, FB Ads, and Grit

15:06 – From Direct-to-Consumer to Billion-Dollar B2B Partnerships

20:58 – Scaling the Team, Redefining Leadership, and Letting Go

22:53 – The IPO Vision (And Who Cody Has to Become to Pull It Off)

27:40 – Success Leaves Clues: Resilience, Reinvention, and a Relentless Vision

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Join 30,000+ founders to get exclusive insights and tactics every week with the SaaS Summit newsletter: www.saasacademy.com/jointhesummit

Where to find Johnny Page

➤ LinkedIn: https://www.linkedin.com/in/johnnypage/

➤ Instagram: https://www.instagram.com/johnnypage13/

➤ YouTube: https://www.youtube.com/@johnnypage1/

➤ Website: https://www.thejohnnypage.com/

Where to find Titans of SaaS

➤ Instagram: https://www.instagram.com/titansofsaas/

➤ YouTube: https://www.youtube.com/@titansofsaas/

➤ Website: https://www.saasacademy.com/podcast/

What would make a former Apple exec sell the only part of his business making money? In this episode, Dean Curtis, CEO of Ingage, shares how he shut down a revenue-generating agency serving Fortune 500 clients to bet everything on SaaS - before finding product-market fit. From a near-collapse in the boardroom to the client that changed it all, Dean unpacks how conviction, clarity, and ruthless product focus turned Ingage into an $8M business.

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Timestamps

00:00 – Meet Dean Curtis

02:27 – From Apple Exec to Agency Life

07:24 – Shutting Down the Revenue Engine (On Purpose)

10:56 – The Moment Ingage Found Product-Market Fit

12:03 – Why Service Businesses Make Great SaaS Incubators

13:01 – Dean’s Product Philosophy: Build Simple, Iterate Ruthlessly

14:24 – The $20M Vision and Building a Team to Match It

16:23 – Success Leaves Clues: From Math Teacher to SaaS CEO

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Join 30,000+ founders to get exclusive insights and tactics every week with the SaaS Summit newsletter: www.saasacademy.com/jointhesummit

Where to find Johnny Page

➤ LinkedIn: https://www.linkedin.com/in/johnnypage/

➤ Instagram: https://www.instagram.com/johnnypage13/

➤ YouTube: https://www.youtube.com/@johnnypage1/

➤ Website: https://www.thejohnnypage.com/

Where to find Titans of SaaS

➤ Instagram: https://www.instagram.com/titansofsaas/

➤ YouTube: https://www.youtube.com/@titansofsaas/

➤ Website: https://www.saasacademy.com/podcast/

Welcome to Titans of SaaS - a show about the real stories behind software that scaled.

In this trailer, our host Johnny Page shares what the podcast is all about, who it’s for, and what you’ll take away from each episode.

Whether you're building your first startup or scaling your next one, this show is your behind-the-scenes pass to how great SaaS companies are really built - from zero to millions and everything in between.

Catch new episodes of Titans of SaaS every week.

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Join 30,000+ founders to get exclusive insights and tactics every week with the SaaS Summit newsletter: www.saasacademy.com/jointhesummit

Where to find Johnny Page

➤ LinkedIn: https://www.linkedin.com/in/johnnypage/

➤ Instagram: https://www.instagram.com/johnnypage13/

➤ YouTube: https://www.youtube.com/@johnnypage1/

➤ Website: https://www.thejohnnypage.com/

Where to find Titans of SaaS

➤ Instagram: https://www.instagram.com/titansofsaas/

➤ YouTube: https://www.youtube.com/@titansofsaas/

➤ Website: https://www.saasacademy.com/podcast/