Between Two Founders

Fernside chat with founders. Presented by Digits

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.

Latest Episodes

Episode 010 - René Lacerte

René Lacerte, CEO of BILL, discusses building financial operations software for SMBs, taking the company public, and his mission to serve the "Fortune 5 Million" small businesses.

Episode 009 - Wade Foster

Wade Foster, CEO of Zapier, reveals how a Startup Weekend project became a fully remote company powering 81B+ automations. Topics include bootstrapping, remote culture, and AI's future.

Episode 008 - Siqi Chen

Siqi Chen, CEO of Runway, discusses reimagining finance tools with AI and design. The 3x founder shares lessons from gaming, startups, and building intuitive financial forecasting software.

Episode 007 - Jean-Denis Greze

Jean-Denis Greze, former CTO of Plaid and co-founder of Town, discusses scaling fintech infrastructure, building developer products, and AI-driven tax solutions for small businesses.

Episode 006 - Josh Reeves

Josh Reeves, CEO of Gusto, shares how he built a category-defining HR and payroll platform serving 400,000+ businesses. Topics include unconventional leadership and customer engagement.

Episode 005 - Travis Hedge

Travis Hedge, Co-founder of Vouch Insurance, discusses building insurance products for startups, his background at SVB Capital, and lessons in scaling a fintech company.

Episode 004 - Aaron Levie

Aaron Levie, CEO of Box, shares how he built a $1B revenue company from his dorm room. Topics include pivots, IPO preparation, competing with Microsoft, and innovation strategy.

Episode 003 - Immad Akhund

Immad Akhund, CEO of Mercury, discusses building a banking platform for startups, leadership lessons, and work-life balance as a repeat founder.

Episode 002 - Christina Cacioppo

Christina Cacioppo, CEO of Vanta, shares how she built a $2.45B security compliance company. Topics include early pivots, scaling customer success, and founder ambition.

Episode 001 - Kayvon Beykpour

Kayvon Beykpour (Periscope, Twitter) discusses M&A, fundraising, and finding product-market fit with Digits CEO Jeff Seibert. The 3x founder shares lessons from growing Periscope to 100M users.