Between Two Founders

Join Jeff as he engages with Jean-Denis Greze, Co-Founder of Town and former CTO of Plaid, for an insightful dialogue about revolutionizing industries and pushing boundaries.Jean-Denis shares his remarkable experiences from scaling Plaid into a fintech powerhouse, detailing how they bridged the gap between consumers' bank accounts and their favorite apps. Now at Town, Jean-Denis is leveraging AI to redefine tax assistance for small businesses, ensuring they receive the high-quality advantages typically reserved for large corporations. Hear firsthand how he navigated the transition from being an operator at Plaid to launching his own venture with an $18 million seed round.Tune in to discover the challenges and triumphs of scaling a startup, the intricacies of leadership, and the exciting future of financial technology. Don’t miss this episode packed with insights and inspiration from two transformative thought leaders in the fintech world.

Episode 006 of Between Two Founders — Dive into an inspiring conversation between Jeff and Josh Reeves, Co-Founder and CEO of Gusto. Explore how Josh turned Gusto into a category-defining company in HR, payroll, and benefits, with insights from his unconventional leadership journey.Between Two Founders is an enlightening series of interviews hosted by Jeff Seibert of Digits, featuring seasoned founders from VC-backed startups offering rare insights from their journeys and first-hand experience.

Episode 005 of Between Two Founders — Join Jeff and Travis Hedge, Co-founder and CRO of Vouch—a tech company reimagining business insurance for startups—for an enlightening conversation packed with unique insights. Between Two Founders is an enlightening series of interviews hosted by Jeff Seibert of Digits, featuring seasoned founders from VC-backed startups offering rare insights from their journeys and first-hand experience.

Episode 004 of Between Two Founders – Jeff Seibert, CEO and founder of Digits, sits down with Aaron Levie, CEO and co-founder of Box, a cloud-based content management company that allows companies to access information from anywhere and collaborate with anyone. In this episode, Jeff and Aaron chat about Aaron’s journey starting Box — from cold-emailing Mark Cuban to his decision to drop out of USC, and the current landscape of the cloud storage space. Between Two Founders is an enlightening series of interviews hosted by Jeff Seibert of Digits, featuring seasoned founders from VC-backed startups offering rare insights from their journeys and first-hand experience.

Episode 003 of Between Two Founders – Jeff Seibert, CEO and founder of Digits, sits down with Immad Akhund, CEO and co-founder of the financial technology company, Mercury, which provides banking services to early-stage startups. In this episode, Jeff and Immad discuss the intricacies of building a high-impact fintech company, scaling a business in the face of intense competition, surviving “fintech winter,” and navigating the ever-complex regulatory landscape. Between Two Founders is an enlightening series of interviews hosted by Jeff Seibert of Digits, featuring seasoned founders from VC-backed startups offering rare insights from their journeys and first-hand experience.

Join Jeff Seibert as he chats with Christina Cacioppo, CEO & Co-Founder of Vanta, a startup revolutionizing trust management. Christina reveals her tough lessons from securing a whopping $150 million Series C round and emphasizes the dangers of hasty hiring. She shares insights on automating security compliance and the importance of customer engagement in achieving product-market fit. The conversation also touches on maintaining work-life balance in the high-stakes world of startups. Tune in for valuable lessons and candid stories!

Episode 001 of Between Two Founders – Jeff Seibert, CEO & Founder of Digits, chats with Kayvon Beykpour, Co-founder of Periscope & Former head of Consumer Product at Twitter. In this episode, Digits founder, Jeff Seibert sits down with Kayvon to discuss a serial-founder’s journey, M&A, fundraising, the importance of intuition, and the path to finding product market fit. Between Two Founders is an enlightening series of fireside chats, hosted by Jeff Seibert of Digits, featuring seasoned founders from VC-backed startups offering rare insights from their journeys, and first-hand experience.