Between Two Founders

Digits

5.0 (9)
ENTREPRENEURSHIP
UPDATED MONTHLY

An enlightening series of fireside chats, hosted by Jeff Seibert of Digits, featuring seasoned founders from VC-backed startups. Gain rare insights from their journeys, and first hand experience.

JAN 28

René Lacerte: Building BILL to Process 1% of US GDP

Episode 010 of Between Two Founders: 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. Connect with us here: 1. René Lacerte- https://www.linkedin.com/in/renelacerte/ 2. Jeff Seibert- https://www.linkedin.com/in/jseibert/ 3. Digits- https://www.linkedin.com/company/digits-financial/ 4. BILL- https://www.linkedin.com/company/bill/ 00:00 Trailer 01:25 Introduction 03:02 René’s Entrepreneurial Roots 05:36 Innovations in Payroll and Financial Operations 07:44 The Genesis of ⁠Bill⁠ 22:59 The Evolution of Leadership 26:19 AI and the Future of SMBs 29:26 Building an AI Platform 34:10 Leadership Reflections and Advice 37:25 Advice for First-Time Founders

42 min
12/01/2025

Zapier, AI Workflows, and the Future of Integration | Wade Foster

Episode 009 of Between Two Founders: 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? 00:00 Trailer 01:09 Introduction 02:45 Wade Foster's Journey: From Missouri to Zapier 08:14 Building Zapier: Challenges and Successes 22:40 Navigating Unconventional Business Strategies 25:48 Innovative Practices for Remote Teams 31:56 AI Integration and Future Prospects

46 min
11/11/2025

Building AI That Multiplies CFOs: Runway

Episode 008 of Between Two Founders: 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." 00:00 Trailer 01:20 Introduction to Siqi Chen and His Journey 02:36 Early Career and NASA Experience 07:38 First Venture and Facebook Platform Success 29:23 Building Accounting Software from Scratch 31:23 The Role of Excel in Financial Planning 37:17 The Future of AI in Finance

58 min
07/30/2025

Between Two Founders (Episode 007) - Jean-Denis Greze

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.

1h 27m
04/23/2025

Between Two Founders (Episode 006) - Josh Reeves

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.

1h 12m
02/05/2025

Between Two Founders (Episode 005) - Travis Hedge

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.

1h 5m
12/03/2024

Between Two Founders (Episode 004) - Aaron Levie

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.

45 min
10/22/2024

Between Two Founders (Episode 003) - Immad Akhund

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.

1h 4m
09/06/2024

Between Two Founders (Episode 002) - Christina Cacioppo

Episode 002 of Between Two Founders – Jeff Seibert, CEO & Founder of Digits, sits down with Christina Cacioppo, CEO & Co-Founder of the trust management platform startup, Vanta.In this episode, Digits founder, Jeff Seibert and Christina discuss Vanta’s monster, $150 Million Series C round, never hiring when hungry, and knocking on doors in SoMa to find PMF.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.

1h 14m
07/09/2024

Between Two Founders (Episode 001) - Kayvon Beykpour

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.

1h 19m

10 Episodes

5

out of 5

9 Ratings

An enlightening series of fireside chats, hosted by Jeff Seibert of Digits, featuring seasoned founders from VC-backed startups. Gain rare insights from their journeys, and first hand experience.

Creator

Digits
Years Active

2025 - 2026
Episodes

10
Rating

Explicit
Copyright

© Digits
Show Website

Between Two Founders