Titans of SaaS

How His Company Nearly Died - And What Saved It | David Cristello

Join Johnny Page as he sits down with David Cristello, founder of Jetpack Workflow, to unpack how he went from hating business to scaling a multi-million dollar SaaS company for accountants. David shares the story behind his first $2,500 pre-sale, the dangers of easy funding, and how he rebuilt his business by falling back in love with solving customer pain. This is a masterclass in resilience, customer discovery, and building a business that lasts. -- Timestamps 00:00 – Meet David Cristello 03:41 – Discovering Entrepreneurship by Accident 07:16 – The Hunt for a Painful Problem 11:29 – When No One Wants Your First Idea 15:04 – Cracking the Accounting Market 18:59 – How a $2,500 Pre-Sale Changed Everything 22:58 – Building the First Version (and Learning the Hard Way) 27:34 – The Rise (and Trap) of Fast Facebook Growth 34:01 – Escaping the Money Trap and Rebuilding 41:33 – Success Leaves Clues: Mastering Customer Secrets and Staying Profitable -- 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/

From “That’ll Never Work” to $7M ARR | Tyler Smith

Tyler Smith never planned to be a founder - but a moment of frustration led to a product that now serves over 10,000 customers. In this episode, Johnny sits down with the accidental entrepreneur behind Text in Church, a SaaS platform that turned follow-up chaos into connection at scale. From running a photography company to managing $7M in ARR and pulling off three acquisitions in six months, Tyler shares how he built a category-defining company through grit, education, and service. -- Timestamps 00:00 – Meet Tyler Smith 01:38 – The Accidental Entrepreneur 03:31 – The Spark for Text in Church 04:36 – The “Southwest Airlines” Epiphany 06:14 – Scaling Beyond a Personal Favor 08:11 – Churches Don’t Want Tools - They Want Outcomes 10:21 – Why Education Became Their Best Marketing 12:13 – Pricing, Trials, and the Power of Loyalty 14:10 – How Acquisitions Became a Growth Engine 17:59 – From Fear to Confidence: Building the M&A Muscle 20:26 – Sitting in Satisfaction… Then Finding the Next Gear 24:22 – Success Leaves Clues: 6 Big Lessons from Tyler’s Journey -- 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/

How an Ex-DJ Built a $4M SaaS in His Parents' Garage | Roby Peñacastro

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. -- 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 -- 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/

He Got Fired From His Own Startup... Then Built a Nine-Figure Company | Cody Barbo

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. -- 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 -- 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/

Why He Walked Away From Apple to Fix a Broken Business | Dean Curtis

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. -- 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 -- 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/