In this episode of Outsider Inc., host Ian Hathaway sits down with Seth Levine, co-founder and longtime partner at Foundry, to explore a two-decade journey at the center of entrepreneurship, venture capital, and ecosystem building outside traditional power centers. Levine reflects on helping build Foundry into a top-tier venture firm based in Boulder, his belief in entrepreneurship as a driver of economic mobility, and the lessons behind his new book Capital Evolution. He also discusses backing overlooked founders, the philosophy of "give first," winding down Foundry by design, and his latest chapter launching Good Bread, a lending platform that expands access to capital for small business owners traditionally shut out of the financial system.

Show Notes:

(02:10) Why Entrepreneurship Fuels Job Creation and Innovation

(03:25) Capital Evolution and the Case for Dynamic Capitalism

(06:05) Long-Term Thinking vs. Short-Term Market Pressure

(08:45) Declining Economic Dynamism and Barriers to Opportunity

(12:00) Family Roots, Class Mobility, and Early Entrepreneurial Influence

(15:45) Lessons from the Dot-Com Boom, Bust, and Corporate Humility

(19:30) Entering Venture Capital After the Crash

(23:10) Founding Foundry and Betting on Non-Coastal Startups

(27:05) Backing Overlooked Founders and Scrappy Entrepreneurs

(31:40) Building a National Venture Platform from Boulder

(35:10) Deciding to Wind Down Foundry and Make Space for New Funds

(38:30) Writing The New Builders and Reframing Entrepreneurship

(41:30) Launching Good Bread to Expand Access to Small Business Capital

(45:45) What Makes Startup Ecosystems Resilient Around the World

(49:40) The Enduring Power of "Give First"

(54:00) Beyond the Bio: Seth Levine

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Seth Levine, Co-Founder of Foundry

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

In this episode of Outsider Inc., host Ian Hathaway interviews Gail Goodman, former CEO of Constant Contact. Goodman discusses her journey from her early entrepreneurial endeavors to leading Constant Contact from startup to IPO and ultimately to a $1.1 billion acquisition. She emphasizes the importance of execution over ideas and how a deep commitment to small businesses shaped her approach to building and scaling a SaaS company. She also reflects on the emotional transition after 17 years as CEO and her ongoing work supporting underrepresented entrepreneurs.

Show Notes:

(02:57) Childhood Entrepreneurial Roots

(06:59) Seeing Dysfunction Up Close and Learning What Not to Do

(08:03) The Leap to Leading Constant Contact

(12:09) Overcoming Imposter Syndrome and Building a CEO Peer Network

(18:59) Customer Research and the Art of "Following Them Home"

(21:13) Cracking Conversion and Retention in Early SaaS

(30:57) Preparing for an IPO and Leading Through Rapid Scale

(33:40) Public Company Pressures and Cultural Shifts

(36:00) The Emotional Reality of Transitioning Out of the CEO Role

(38:14) Joining Boards and Rethinking Leadership from a New Seat

(44:10) Being an Outsider in Tech and Venture Capital

(47:30) "People Gut" and the Art of Hiring Well

(51:55) Supporting Underrepresented Entrepreneurs Through EforAll

(54:00) Beyond the Bio: Gail Goodman

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Gail Goodman, Founder & CEO of Constant Contact

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.

In this episode of Outsider Inc., host Ian Hathaway interviews Kyle Porter, founder and longtime CEO of SalesLoft. Kyle shares his remarkable journey from nearly failing in the first year of SalesLoft to scaling the company to unicorn status with a $2.3 billion valuation. He discusses the core principles of leadership, such as leading with love, staying mission-driven, and valuing corporate culture. Kyle also reveals personal challenges, including childhood health issues and a transformative college experience, and how these shaped his entrepreneurial path. Finally, Kyle talks about his current life on a tangerine farm and supporting his wife's business endeavors, emphasizing the importance of family and personal fulfillment.

Show Notes:

(02:12) Leading with Love: A CEO's Perspective

(02:55) Kyle's College Turning Point

(04:55) Childhood Hustles: The Seeds of Sales Passion

(06:52) Overcoming Childhood Health Challenges

(12:57) Early Professional Experiences and Lessons Learned

(15:51) The Birth and Rebirth of SalesLoft

(26:49) Navigating the Pandemic: Challenges and Growth

(30:41) Life Changes During the Pandemic

(31:31) The Vista Equity Acquisition

(34:31) Transitioning from CEO to Executive Chairman

(37:16) Supporting Each Other's Dreams

(44:04) Building SalesLoft in Atlanta

(51:08) Beyond the Bio with Kyle Porter

✅ Host: Ian Hathway - Co-Founder & Managing Partner, FOVC

✅ Guest: Kyle Porter, Founder & fmr CEO of SendGrid

Produced by Spellbinder Media. Executive Produced by Bridge Five Ventures. Copyright ©️2025, Bridge Five Ventures, LLC, All rights reserved.

Listen & subscribe wherever you get your podcasts or at outsiderinc.substack.com.