Between Two Founders - Digits

René Lacerte

Wed, 28 Jan 2026 00:00:00 GMT

René Lacerte has spent nearly three decades building the financial infrastructure that powers millions of small businesses. As the founder and CEO of BILL, he has created a platform that now processes over 1% of US GDP, serving nearly half a million customers and 9,000 accounting firms.

In this epsiode with Jeff Seibert, René shares his journey as a fourth-generation entrepreneur. He introduces the concept of "Owner Mode" as his alternative to the founder mode vs manager mode debate, and shares his contrarian view that SMBs don't want more AI, they want less work.

The episode also marks the launch of the Digits × BILL partnership, designed to simplify and automate financial operations in real time while reducing manual work and errors.

A masterclass in building financial infrastructure that works for small businesses.

Wade Foster

Thu, 04 Dec 2025 00:00:00 GMT

Jeff sits down with Wade Foster, Co-founder and CEO of Zapier, to uncover how a “weird,” fully remote team built one of tech’s most influential platforms, now behind 81+ billion automations.

Wade also shares Zapier’s origins, from a Startup Weekend in Columbia to a second shot at YC, and reveals how Zapier is weaving AI into its workflow engine to make automation both reliably structured and intelligently adaptive.

Stay till the end to hear Wade answer: What’s the CEO of Zapier’s favorite use of his own product?

Siqi Chen

Wed, 12 Nov 2025 00:00:00 GMT

Join Jeff as he sits down with Siqi Chen, CEO and co-founder of Runway, to explore a journey that spans gaming, virtual reality, and B2B SaaS, culminating in a mission to make finance teams 10x more efficient through AI and design.

Siqi shares why the most powerful products amplify human intelligence rather than replace it, how design principles from consumer tech can simplify even the most complex systems, and how he is building what he calls an “Ironman suit for finance teams.”

Tune in now to hear why Siqi Chen believes, "For every intellectual task, for sure, the AI will do a better job of it."

Jean-Denis Greze

Wed, 30 Jul 2025 00:00:00 GMT

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.

Josh Reeves

Wed, 16 Apr 2025 00:00:00 GMT

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.

Josh shares behind-the-scenes stories, from taking bold bets to overcome early struggles, to driving across the U.S. in an RV to connect directly with customers. Discover how Gusto grew under his leadership to serve over 400,000 businesses, processing billions in payroll while championing thriving workplace cultures.

Plus in this special episode of Between Two Founders, we launched our partnership with Gusto! Learn more here!

Travis Hedge

Mon, 10 Feb 2025 00:00:00 GMT

Join Jeff and Travis Hedge, Co-founder and CRO of Vouch—a tech company reimagining business insurance for startups.

Travis talks about his journey from venture capital to the spark that led to building Vouch. In a conversation truly between two founders, Travis engages Jeff in a raw discussion about what being a founder really means — from making challenging decisions, to being on 24/7, raising a family, and more.

Aaron Levie

Wed, 29 Jan 2025 00:00:00 GMT

Jeff Seibert, CEO & Founder of Digits, chats with Aaron Levie, CEO of Box.

In this interview, Aaron Levie shares Box's journey, from early pivots to IPO, plus insights on innovation, competition, and scaling a business.

Immad Akhund

Tue, 22 Oct 2024 00:00:00 GMT

Jeff Seibert, CEO & Founder of Digits, chats with Immad Akhund, CEO of Mercury.

In this interview, Immad Akhund discusses his early career, Mercury, and answers questions on topics like leadership, work-life balance, and more.

Christina Cacioppo

Fri, 06 Sep 2024 00:00:00 GMT

Jeff Seibert, CEO & Founder of Digits, chats with Christina Cacioppo, Vanta Cofounder and CEO.

In this interview, we speak with Christina Cacioppo, CEO of Vanta, who shares her startup journey, from modest early visions to larger ambitions.

Kayvon Beykpour

Fri, 30 Aug 2024 00:00:00 GMT

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.