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.

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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

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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/

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.

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Timestamps

00:00 – Meet Tyler Smith

1:38 The Accidental Entrepreneur

3:31 The Spark for Text in Church

4:36 The “Southwest Airlines” Epiphany

6:14 Scaling Beyond a Personal Favor

8:11 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

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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/

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/