Venture Capital22 Apr 2025

What Questions Should Founders Ask VCs? Insights from Jon Bradshaw and Peter Harris

In this episode of the Venture Capital Podcast, hosts Jon Bradshaw and Peter Harris dive into one of the most critical yet often overlooked topics for startup founders: the questions you should be asking venture capitalists before taking their money. Drawing on their extensive experience, Jon and Peter discuss common pitfalls that founders face when negotiating deals, including the hidden terms in contracts that can come back to haunt a company years later.

The hosts stress the importance of doing deep due diligence on potential investors—not just their financial terms, but their character and how they handle failure. They emphasize asking tough questions about how a VC firm supports struggling portfolio companies and their philosophy on valuation and terms. Jon and Peter also reflect on the delicate balance founders must strike in pushing back while maintaining a constructive relationship.

Listeners will gain valuable insight into the realities of venture capital beyond the pitch room—the importance of understanding who is investing in your company, how VCs behave when things go wrong, and how to spot red flags early. This episode is an essential guide for founders preparing to raise capital and aiming to build a strong, lasting partnership with investors.

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