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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