How do you grow a startup into a transformative force in a highly regulated, slow-moving industry? John Swigart, Co-Founder and CEO of Pie Insurance, joins David Politis to discuss the importance of decisive leadership, the balance between founder intuition and executive delegation, and how execution at scale can be a long-term competitive advantage. 

From assembling a thoughtful board to reorienting a business for profitability, John shares lessons from building a modern insurance company from scratch.

Takeaways:

• Decisiveness Around Leadership Transitions: John emphasizes making tough calls on leadership team members who may no longer be the right fit as a company evolves. Waiting too long creates compounding challenges and stalls progress.
• Balancing Founder Involvement with Delegation: He reflects on the “founder mode” concept, describing the need for leaders—founder or not—to stay close to the details while avoiding micromanagement. Clarity and context are key.
• The Decision-Making Matrix at Pie: John explains Pie’s internal framework for decision-making, which clearly defines who owns decisions, who contributes input, and how final calls are made—helping empower teams without chaos.
• Why Pie Competes in a Difficult Industry: Despite the dominance of legacy players in insurance, John saw a real opportunity: a fragmented market with outdated tech and poor customer experience. Pie’s modern, data-driven model aims to change that.
• Process Power as a Competitive Moat: Pie focuses on doing hundreds of small things better than the competition. John describes how consistent operational execution and better technology form a durable advantage over time.
• Adapting to a Profitability-Focused Environment: John details the major internal shift required when venture markets changed in 2022—from “grow at all costs” to sustainable, efficient operations. Layoffs and restructuring followed, but the business emerged stronger.
• Advice to His Younger Self: John would tell his younger self—and others early in their careers—to say yes to opportunities that offer growth. Don’t over-optimize for money or title; focus on learning and exposure instead.

Quote of the Show:

• "Early in your career, optimize on learning growth, exposure, opportunity, not on money or title or, or anything of that nature." - John Swigart

Links:

• LinkedIn: https://www.linkedin.com/in/johnswigart/
• Website: https://www.pieinsurance.com/

Ways to Tune In:

• Substack: https://notanotherceo.substack.com/
• Spotify: https://open.spotify.com/show/1NQ9oAB2XKlgWeL8iEQXg0 
• Apple Podcasts: https://podcasts.apple.com/us/podcast/not-another-ceo-podcast/id1751581707 
• YouTube: https://www.youtube.com/@NotAnotherCEOPodcast 
• Transistor: https://podcast.notanotherceo.com/ 

#NotAnotherCEO #BusinessSuccess #PieInsurance

Chapters:

00:00 Intro

01:42 Key Decisions and Leadership Challenges

07:24 Building and Evolving Leadership Teams

11:03 The Concept of Founder Mode

20:58 Competing in a Highly Regulated Market

31:13 Early Days and Customer Acquisition

31:53 Early Days of Multi-Channel Distribution

34:35 Fundraising Challenges and Successes

36:59 Building an Impressive Board

42:33 Navigating Business Challenges

48:39 Founding a Company Later in Life

53:46 Personal Growth and Mentorship

57:06 Pivotal Career Moments

01:00:48 Advice for Aspiring Entrepreneurs

01:02:17 Outro