People don't realize how long it takes to figure out if a company is good or not. I mean, when you're investing in inception, where there's no lines of code written, so you're talking about companies are two to three years old. I told you earlier how- Seeds like three years old. Block Damon had seven seed rounds, okay? So Block Damon, sneak, customer, big ID, our best companies had no other A round investors sitting behind validating

what we're doing. And yet we're pounding the table saying, these companies are awesome. Like, check this out. Yeah. It's moving in the right direction. But on the flip side, you were able to like invest a little bit more in the companies and own more for your investors. We own a lot more. Yeah. Yeah. And so like, so think about that challenge. We didn't have outside validation.

Frankly, if you want to get real institutional LPs, they like to call their brother and up that they've backed before and say, who are the ones that you're following? Who are the ones that you want to get deal flow from? That fund for was so hard for us because we didn't have enough of those at the time. And so that fund took us, I don't know, two years to raise. We didn't get it close fully until end of 2019 or somewhere around there. And seven closes, we almost didn't even get our first clothes done. But it was probably one of the most painful experiences where I didn't even know if Bullsear was going to keep going on at some point in time. Wow. Because we had a hard time raising capital because people didn't believe in enterprise or infrastructure. We wins, but not enough proof points. The world's 10 around Silicon Valley. But we were laying around, we're in the boards, but yet these companies didn't inflect enough at the time to prove it out. And then Fund Five was a different story because by then a lot of the companies just hit inflection. They all raised a bunch of capital, but it was the Valley of Death, man.

Welcome to the Peel, where we explore the world's greatest startup stories.

I'm your host, Turner Novak, founder of Nanda Capital, venture capital firm that helps you cross the Valley of Death. Today, I talked to Ed Sim, founder of Bold Start Ventures, which partners

with bold founders reinventing the

enterprise stack at the inception stage. Ed takes us inside key moments of building Bold Start,

including creating the seed category with their first $1 million fund in 2010, the grind

of raising each of the next three funds, why Ed didn't join a larger firm in 2012, and inside being the first

investor in companies like sneak, superhuman, customer, big ID, block Damon, and protect AI.

Ed also shares the five P's of inception stage investing, how he analyzes new markets without

a market map yet, how to build relationships with potential customers and advice

for closing them, the three Cs of a good board member, how his board role evolves from inception

to IPO, his approach to LP fundraising, and who he thinks will be the winners and losers in

AI. I talked to a bunch of people preparing for this episode. A special thank you to Shomakosh

a bold start, Scott Yara at Sutter Hill,

and Guy Pajarnie at Sneak for all your help. Let's jump in after a quick word from our sponsors.

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