One founder. One real conversation. 30–50 minutes on what it actually took to build, raise, and scale.
52+
Episodes
30–50
Minutes each
1
Founder per episode
All Episodes
Cody Graham
COO, SoGo
Cody walks through the mindset shifts required to move from corporate operator to startup builder — covering AI integration, building community-driven products, and why the best founders stay deliberately uncomfortable.
Steve Ramona
Founder & Podcast Host
Steve breaks down his ASLA framework — Ask, Listen, Learn, Act — and demonstrates how authentic networking can turn a casual conversation into a long-term business relationship. One of the most practical episodes on relationship capital we've recorded.
Iliana Alvarado
Founder, N6 Systems
Iliana built a tech venture across three countries after a career defined by embracing the unpredictable — from odd jobs to international roles. She makes a compelling case that cultural agility is the most underrated founder skill.
Sharon Gai
Former Alibaba Executive & Keynote Speaker
Sharon went from leading Alibaba's global growth to building her own personal brand — and discovered that documenting failures outperforms polished success stories. She shares the counterintuitive rules of digital presence and why AI is the great equalizer for solo founders.
Russell Breuer
Founder, Spot & Tango
Russell left management consulting to cook dog food in his apartment. Nine figures later, Spot & Tango is one of the fastest-growing DTC pet brands in the country. He breaks down the direct-to-consumer playbook and the bet on personalized nutrition that changed everything.
Gadareth Higgs
Investment Analyst, Grander
Gadareth went from the Bahamas to Yale to the front lines of life sciences investing — and shares how he evaluates early-stage biomedical companies, why continuous improvement is his operating system, and how AI is reshaping the due diligence process.
Robie Webster Jr.
Founder, Mtrc
Former Division I athlete Robie Webster Jr. turned the discipline of competitive sport into a fitness technology company. He talks about finding a co-founder, the grit it takes to build without a safety net, and why learning never stops for a first-time founder.
Chris Tsakalakis
Former CEO, StubHub · Venture Partner, Starhawk
Chris ran one of the most recognizable B2C marketplaces in the world before pivoting to venture. He traces the lessons from Bain to StubHub, the aggressive marketing bets that paid off, and why he believes AI's impact on business will be bigger than the internet.
Chris Yeh
Co-Author, Blitzscaling · Investor & Speaker
Chris co-wrote the book on blitzscaling with Reid Hoffman — and in this episode he goes deeper on what actually separates companies that scale from those that plateau. He covers conviction, lifelong learning, and building the kind of collaborative network that compounds over decades.
Andrew Ackerman
Two-Time Exit Founder & Author
Andrew has navigated two startup exits and written a book about it — The Entrepreneurial Odyssey. He shares the resilience frameworks that got him through the hard parts, the mental models he wishes he'd had earlier, and what he tells first-time founders who are just starting to feel the pressure.
Frances Pratt
Founder & CEO, Metisan
Frances built a sales consulting firm for founders who are brilliant at their craft but uncomfortable in the room. She explains why most selling fails at listening, how storytelling closes deals that decks can't, and the community-building strategies that create revenue without cold outreach.
Aya Kikimova
Founder & Former Microsoft
Aya left the stability of Microsoft to build from scratch — and she's honest about how different the two worlds are. She maps the psychological and operational challenges of the transition, the obstacles she didn't see coming, and how she found her footing as a first-time solo founder.
Be on the show
We only record with founders who have real reps — a raise, an exit, a lesson hard-earned. If that's you, reach out.
Pitch yourself as a guestStart to Scale is produced by Gildre. New episodes drop monthly.