Founders: These Are the Mistakes You Don't Know You're Going to Make | Steve Walsh, Ep 52

Founders: These Are the Mistakes You Don't Know You're Going to Make | Steve Walsh, Ep 52

Steve Walsh, an angel investor and startup advisor, shares lessons from 25 years building multi-billion dollar B2B divisions at Cox and Comcast before transitioning to helping early-stage founders. He discusses common founder mistakes, when to raise capital, the importance of customer validation before building product, and how he filters 6,000 conversations down to 69 investments through rigorous vetting and founder education.

The CEO Is the Salesperson: Why Founders Can't Hand Off the Pitch | Jen Bonnett, Ep 49

The CEO Is the Salesperson: Why Founders Can't Hand Off the Pitch | Jen Bonnett, Ep 49

Jennifer Bonnett, a longtime tech entrepreneur and former ecosystem builder at ATDC and Invest Atlanta, discusses her transition back into technology through AI experimentation. She shares lessons from building a search engine in 1997, her current work vibe coding consumer apps with Claude, and her philosophy that CEOs must personally sell for at least the first year before delegating. The conversation explores how AI is lowering barriers to entrepreneurship while emphasizing that founders still need strong networks, customer discovery skills, and the discipline to market early.

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

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

Katherine O'Day, partner at Atlanta Ventures, discusses her journey from employee number nine at Pardot through two successful acquisitions (ExactTarget, then Salesforce) to becoming an early-stage investor and venture studio operator. She shares lessons on bootstrapping companies, building culture through core values, and why consistent execution over time—like training for an Ironman—matters more than short bursts of effort in entrepreneurship.

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

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

Chris Caparon, co-founder and former CEO of Sephoria Software, shares his 20-year journey building an accounts receivable automation company from a garage startup to a successful exit to private equity. He discusses navigating multiple economic crises, evolving technology platforms, and the relentless customer focus that enabled his bootstrapped company to serve Fortune 500 clients across 110 countries.

Winning Strategies from Gridiron Grit to Healthcare Innovation | Jay Kleinman, Ep 05

Winning Strategies from Gridiron Grit to Healthcare Innovation | Jay Kleinman, Ep 05

Jay Kleinman, a 30-year healthcare sales and business development veteran, discusses how lessons from playing D1 football at Auburn under Pat Dye shaped his approach to building commercial teams for early-stage healthcare companies. He covers segmentation strategy, discovery-based selling, and the transformation of elder care through digital health and telemedicine adoption accelerated by COVID-19.

Want to go deeper?

Work With Me