Andrew Ackerman, 2x startup founder, venture capitalist, and author of The Entrepreneur’s Odyssey, joins us on Inside the Fund to talk about valuation, investor psychology, and what founders get wrong about fundraising process.
In this episode, Andrew explains why most founders have less leverage on valuation than they think, why competing term sheets matter so much, and why investor FOMO is often the only thing that speeds up a deal. We also get into spray-and-pray outreach, deck mistakes, governance rights, liquidation preferences, and the fundraising process errors founders make over and over again.
Andrew also shares lessons from building through the dot-com era, moving into angel investing, helping build industry verticals at Dreamit, and working closely with founders across proptech and construction tech. It’s a practical conversation about credibility, process, and how to raise more effectively in a tougher market.
Topics we cover:
Why founders usually have less valuation leverage than they think
The only real way to improve a term sheet
Why investor FOMO speeds up deals
Why spray-and-pray outreach hurts credibility
The sales discipline founders need in fundraising
What Andrew looks for when evaluating founders
Common pitch deck and process mistakes
What founders should do after receiving a term sheet
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