Did becoming an investor yourself cause you to be more compassionate toward founders or more demanding from

founders? Yes and yes, I guess.

You know, there's among the best founders, there's a little bit of a preference to work with VCs who also have their own startups because they get it, rightly or wrongly.

But being a founder doesn't mean you're a great VC.

Right.

Because there's so many other things about recruiting, assessing.

You can be great at building a business, not be great at assessing 20 other businesses.

So what have accelerators taught you about how entrepreneurs learn, adapt and mature under pressure?

Can't

not do it like they feel so passionate about something that they will keep banging their head against the wall until the wall breaks.

So I had a founder.

This was in one of my colleagues investments in the health tech space.

He was a student at the time.

He was a medical student and a PhD student at a very, very prestigious school.

His mother got breast cancer and he was at the radiologist and they were talking about like how they were going to take the two streams of radiation and cross them so that the cancerous tissue would get a lethal dose of radiation.

Now, what is one piece of advice that you find yourself repeating over and over again? Because people just continue to overlook it.

Yeah.

So they had, like, Code Year, so you're supposed to, like, learn, like, it was like, uh, HTML and CSS, a little bit of JavaScript, and you could do that all.

And I was actually between two startups at the time and, and, like, it hadn't been announced publicly that I'd left.

So I just sat down, I had, like, a month or two, and I just banged through it.

And when I'm done, I'm like, "I don't really know if I've learnt this," 'cause I was just doing their, their exercises.

So I had to set for myself my own little project that I wanted to do, and then I'm like, okay, I really understood it.

So the limitation here is, like, here I am in the venture world, or at the time in the venture world, but I was consulting for other VC funds mostly rather than doing my own investments, doing some of my own SPVs.

Mm-hmm.

Oh, okay.

So one of the things that I talk about is it's worth having a premortem.

So what that means is, you know, before you start something, you're gonna make a big decision about a direction you want the company to go or a partnership you wanna enter in.

I ask my founders, "Pretend it's three years from now and this failed, right? It failed.

I want you to kind of brainstorm why it failed.

Come up with like three, four, even 10 stories that would get you to the and then this thing didn't work the way we wanted it to." And what I find is as they start to think about, you know, what those premortems might look like, that surfaces risks they weren't thinking about, right? It's like, "Well, you know, we, we wanted to go with this freemium model, but it turns out that not enough people upgraded from free to premium, so the model didn't work." I'm like, "Well, okay, that's great.

If that's your premortem, let's take it to the next step," right? For each of those premortems, like, or for that one in particular, how do we test this? Well, okay, and this is a true story.

Um, how did, how did becoming an investor change your perspective?

So then I

laid out, I'm like, listen, like, you know, I, I think that, you know, you might have something really good, but like, I've seen a lot of companies that are going to make this up.

I see a lot of companies that are freemium, right? They get started off free and they need people to upgrade the, you know, it's really, really hard to get people to make that jump from free to paid.

And I feel like your company is one of those where you're not going to get enough people to do that.

So I think you need to change.

Yeah.

So that's actually really interesting information for you because that will say, hey, you know what? That percentage of upgrades, that may be a make or break assumption for my model.

So I automated that.

You had a, a crazy thing happen on a bike ride when you were young.

Yeah.

When I was five years old, uh, my mom and dad were sticklers to be home for dinner time, and I looked at somebody's watch, and I was gonna be late.

And I said, "Oh, God, I gotta get home or I'm gonna be in big trouble." And this gal says, "I'll give you a ride on my bike." So I thought, "Fine." I jumped on the back of her bike, and we went a block or two, and jumped a curb, and kind of swerved a little bit, and my, uh, left heel went into the spokes.

And it twisted my leg, and I heard a pop.

And, uh, she got me home, and, uh, I was kind of whining.

And Mom, you know, was nice and saying, you know, "Are you okay? What's wrong? What happened?" And Dad got home, and he said, "Pull yourself up by your bootstraps." He was a Marine in Guadalcanal, Iwo Jima, and Okinawa.

Sure.

You had a, a crazy thing happen on a bike ride when you were young.

Yeah.

When I was five years old, um, my mom and dad were sticklers to be home for dinner time, and I looked at somebody's watch and I was gonna be late.

And I said, "Oh, God, I gotta get home or I'm gonna be in big trouble." And this gal says, "I'll give you a ride on my bike." So I thought, "Fine." I jumped on the back of her bike, and we went a block or two and jumped a curb, and kind of swerved a little bit and my, uh, left heel went into the spokes, and it twisted my leg and I heard a pop.

And, uh, she got me home and, uh, I was kind of whining.

And Mom, you know, was nice and saying, you know, "Are you okay? What's wrong? What happened?" And Dad got home, and he said, "Pull yourself up by your bootstraps." He was a Marine and got in Guadalcanal, Iwo Jima, and Okinawa.

And, uh, he, uh, was German, and he never told me once in his life that he loved me.

Sure.