Seed-Stage Investing

The practice of leading early-stage venture capital rounds for startups, focusing on transformational innovation, founder coaching, and building relationships before companies reach significant revenue milestones.

9 episodes

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.

Inside Secrets to Angel and Crowdfund Investing | Karen Rands, Ep 47

Inside Secrets to Angel and Crowdfund Investing | Karen Rands, Ep 47

Karen Rands, founder of the Compassionate Capitalist Movement, discusses how individuals can build wealth by investing in entrepreneurs through angel investing and equity crowdfunding. She shares her journey from IBM intrapreneur to angel investor advocate, explains revenue-share investment models as alternatives to traditional equity deals, and outlines strategies for building diversified portfolios that generate both financial returns and social impact.

Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners | Chris Thomajan, Ep 42

Bet on the Jockey, Not the Horse: A 35-Year CFO's Guide to Backing Winners | Chris Thomajan, Ep 42

Chris Thomajan, a CFO with 35 years of experience across 100+ startups, discusses his career path from English major to finance leader in Boston's biotech ecosystem. He shares frameworks for evaluating founding teams, navigating venture capital cycles, and preparing companies for IPO, emphasizing that betting on the right 'jockey' matters more than the business idea itself.

Earning Every Win: Grit, Innovation, and Knowing When to Venture | Lisa Calhoun, Ep 25

Earning Every Win: Grit, Innovation, and Knowing When to Venture | Lisa Calhoun, Ep 25

Lisa Calhoun, managing partner of Valor Ventures, discusses her fourth-generation entrepreneurial background and leading seed-stage B2B AI and SaaS investments across the South. She explains venture capital's relational nature, the 2024 venture winter that shuttered 40% of smaller funds, and how AI is eliminating coding as a constrained resource while transforming software development economics.

2025 Trends: AI, Venture Capital, and the Future of Work | Bryan Dennstedt, Ep 22

2025 Trends: AI, Venture Capital, and the Future of Work | Bryan Dennstedt, Ep 22

Bryan Dennstedt, fractional CTO at Tech CXO and sustainable investing advocate, discusses 2025 trends with host Todd. They cover venture capital's conservative shift post-SVB, AI's permeation across business (from agents to trust frameworks), the rise of niche podcasts and influencer marketing, and crypto's regulatory thaw under new US leadership. Core insight: AI and blockchain will become as fundamental as electricity, but organizations must navigate trust, compliance, and the trough of disillusionment before realizing transformative value.

Sales, Marketing, Sumerians and Avoiding Founder's Disease | James Rozich, Ep 21

Sales, Marketing, Sumerians and Avoiding Founder's Disease | James Rozich, Ep 21

Jim Rozich, founder of Wheels Up Sales and Marketing, discusses common mistakes early-stage founders make when going to market—particularly 'Founder's Disease,' where entrepreneurs lead with product features instead of customer value. He covers CRM implementation, value-based email messaging, discovery call methodology, and how AI tools should support rather than replace human sales judgment.

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.

Machine Learning at MIT to Entrepreneurial Growth and Fundraising Success | David Morczinek, Ep 08

Machine Learning at MIT to Entrepreneurial Growth and Fundraising Success | David Morczinek, Ep 08

David Morczinek, CEO of Airworks, discusses his journey from aerospace engineering at Airbus to founding a geospatial AI company at MIT. He explains how Airworks analyzes aerial data from drones, satellites, and aircraft to automate infrastructure mapping, the pivot from pure AI to AI-plus-services when customers weren't ready for full automation, and navigating multiple funding rounds from seed to private equity while maintaining work-life balance.

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

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

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 to supporting portfolio companies, the firm's focus on high-net-worth investors, and strategies for navigating the current venture market. Flickinger emphasizes the importance of board governance, team-based competitive experience, and building sustainable businesses during economic downturns.

Want to go deeper?

Work With Me
Back to all topics