What’s Inside
Why founders should evaluate investors as carefully as investors evaluate them
What to expect from real platform teams, and what to ignore
How to think about board seats
Greg Sands doesn’t dance around the truth.
When I asked what early-stage founders often miss when choosing investors, he got straight to it:
“Founders should expect firms to have a theory of their value add, and to have it show up in references. Because if it doesn’t, then it’s literally just Money. And everybody’s money is green.”
Greg is the founder and managing partner at Costanoa Ventures, an early-stage firm that backs AI, infrastructure and Cybersecurity companies.
He’s seen the venture cycle from both sides: as the first product manager at Netscape and now as a board member and investor in dozens of startups.
In this 30th episode of The Venture Variety Show, Greg moves fast, answering rapid-fire questions about what really matters when choosing a VC, building boards and navigating platform hype.
I started The Venture Variety Show last year to bring more dimension to venture conversations. I wanted to focus on the work behind the capital, and the people doing that work, whether or not they’re front and center and on the cap table.
Even when I speak with established GPs like Greg, I try to steer the conversation toward how they actually support founders, not just what successes they’ve had and what sectors they invest in.
I want to know how they show up in boardrooms, what’s the best way to help startups with hiring decisions and what do they do when entrepreneurs have moments of doubt.
Here is Greg’s takes on a variety of topics.
Founders pitch like crazy. But they too often forget they’re making a buying decision, too. Greg advises founders to treat VC diligence seriously:
“The way that you figure out whether a VC treats founders with respect is to call the founders who’ve worked with them, especially the ones whose companies didn’t work out.”
The term is thrown around constantly, but Greg breaks it down:
“Founder-friendly isn’t the whole picture. What you really want is someone who’s company-friendly, who has your back, tells you hard truths, and helps you win.”
Greg draws a hard line between surface-level support and deep engagement. Costanoa’s BuilderOps team helps its portcos with talent, sales and marketing. But it’s meant to complement a partner who knows the startup’s business inside and out:
“Founders don’t need another meeting. They need someone who helps them do the work, and who actually knows the context.”
Not every board seat is created equal, according to Greg. He breaks the math down:
“About 20% of VCs on boards are true difference makers. 40% are neutral. The rest are sand in the gears. And most founders have no idea until it’s too late.”
This episode is a practical guide for founders navigating the investor landscape. Whether you’re raising your first round or remaking your cap table, Greg’s advice cuts through the noise. And he helps entrepreneurs make the long-term calls.
If this episode gave you something to think about, share it with a founder you know.
Subscribe to The Venture Variety Show by following this Substack, and you can also find the show on YouTube, Spotify and Apple Podcasts.
And if you’re curious about how AI is shaping the future of work, check out my other podcast, The AI Cognitive Shift, produced in partnership with AiNews.com.
