What happens when investors have to pitch a deal to other investors? In this episode, Mike, Ben, and Jacob turn the tables and talk about the art of selling an investment without sounding like you’re selling it too hard. The hosts discuss everything from putting your own “chip on the table” to asking about founders' salaries, ownership, and even what happens if a husband-and-wife founding team gets divorced. They also get into the challenge of syndicating deals with friends and fellow investors, where credibility matters just as much as enthusiasm—and where overselling a deal can come back to bite you the next time you have something to syndicate.

Ultimately, the hosts come back to a pretty simple idea: good investing conversations aren't about convincing someone to say yes. They're about being honest enough to share both why you believe in the opportunity and where you think it could go wrong.

Key Topics

• Why syndication becomes necessary for larger fundraising rounds

• Investor-to-investor communication vs. founder-to-investor communication

• The importance of knowing your audience when pitching a deal

• The risks of pushing an investment too aggressively

• Using smaller checks to reduce investment and relationship risk

• Separating current-round participation from past investment

• Reading signals from investors who choose not to follow on

• Asking uncomfortable questions during investment diligence

• Planning for personal and professional contingencies at a startup

Connect

Mike Kelly

• LinkedIn

• Website

• Developer Town

Ben Pidgeon

• LinkedIn

• VisionTech

Jacob Schpok

• LinkedIn

• Elevate Ventures

Hear more interviews and stories like this one at www.VentureDeclassified.com

The information provided on the show is not intended to be investment advice and should not be relied upon as such. The investors on today’s episode are providing their opinions based on their own assessment of the businesses or topics presented. Those opinions should not be considered professional investment advice. If they start up pitched as a part of this episode, it is for informational purposes only and is neither an offer to purchase nor a solicitation of an offer to sell, subscribe for or buy any securities.