Bootstrapped Growth Strategy

Ep 39—Neal Miller-Decades of Financial Strategy Across 70 Companies and Still Going

Neil Miller, a partner emeritus at Tech CXO with 19 years at the firm, shares his journey from public accounting through CFO roles at multiple public companies to fractional executive work. He discusses his involvement with 70+ companies including Cloud Sherpas and Boomtown, offering insights on fundraising challenges, the fractional executive model's value during economic uncertainty, and how AI is compressing business cycles while changing capital requirements.

Ep31 Mike Biwer—The Hidden Engine of the Economy: Unpacking the Power of Distribution with Cavallo

Mike Biwer, CEO of Cavalo, discusses how his company helps wholesale distributors optimize profitability through technology that controls pricing and margins at the line-item level. Founded by a distributor who built software to solve his own business problems, Cavalo evolved from a Microsoft Dynamics add-on to a multi-platform solution serving the $10 trillion distribution industry. Biwer shares insights on navigating ERP migrations, maintaining product-market fit, and competing in a fragmented market where average pre-tax profit margins are under 5%.

Ep22 Antonio Pagano—Phishing, AI Scams, and the Ever-Intensifying Cybersecurity War

Ep 19 Kathryn O'Day —Triathlons, Startups, and Success: A Playbook for Entrepreneurs

Ep12 Katherine Hunter-Blyden: Tips on the Modern Marketing Landscape from a Seasoned Expert

Katherine Hunter-Blyden, a fractional CMO, discusses her career journey from Fortune 500 companies like Ford and Progressive to serving small businesses. She shares insights on modern marketing strategies, the importance of email marketing and content distribution, measuring business growth, and how AI tools are transforming marketing efficiency. The conversation covers practical approaches to brand building, direct response marketing, and the critical differences between marketing at scale versus scrappy startup environments.

Ep 10 - Chris Caparon: Hard-Won Lessons from a Long and Successful Tech Journey

Chris Caparon shares his 20-year journey building Sephoria Software, an accounts receivable automation company that grew from a garage startup in 2001 to serving Fortune 500 companies across 110 countries before its private equity exit. He discusses navigating multiple economic crises, evolving technology platforms, and the critical importance of customer-centric product development and maintaining strong founder relationships throughout the company lifecycle.

Ep 04 - Mark Flickinger: From Rowing to Venture Capital - Lessons in Teamwork and Growth

Mark Flickinger, partner at BIP Ventures, discusses his journey from mechanical engineering and competitive rowing to venture capital. He explains BIP's platform-heavy approach with 50 employees supporting both investors and portfolio companies, their focus on high net worth LPs, and strategies for helping founders navigate the current market environment. Flickinger emphasizes the importance of solving real problems, building strong boards, and maintaining discipline during economic uncertainty.