What if the biggest mistakes founders make when raising capital have nothing to do with their pitch -- and everything to do with timing, team, and expectations?

This fast paced, founder friendly episode features Alan Wink, recently retired Managing Director of Capital Markets at EisnerAmper, one of the largest accounting and advisory firms in the U.S. With decades of experience in venture capital, private equity, and capital strategy, Alan breaks down what entrepreneurs really need to know before taking on outside investment.

What You'll Learn

• Why investors bet on people, not products – and why team quality outweighs early metrics.
• How much to raise and when – the misconceptions that derail founders early.
• VC vs. PE vs. family offices – who they are, what they want, and how they think.
• Why coachability matters – and how alignment influences investor decisions.
• The "game of thirds" in venture capital – and what 10x expectations mean for founders.
• Why fundraising always takes longer than expected – and how to plan for 18–24 months of cash flow.

Alan shares why Investors care far more about future projections and unit economics than historical performance. Founders must show they can solve a meaningful problem, scale efficiently, and deliver returns that match investor expectations. Alan also emphasizes that taking on third party capital is a marriage – one that brings accountability and investor oversight. Alan shares how founders can perform effective due diligence to vet investors as carefully as investors vet companies.

Why This Episode Matters

Alan’s experience advising technology, life sciences, clean tech, and emerging growth companies gives him a unique vantage point on what separates fundable startups and mid-stage companies from the rest. His guidance is practical, realistic, and essential for any founder preparing to scale.

A concise, high-impact conversation packed with insights you can apply immediately.