The Exchanges

Q Fantastic. And all of those can be found on the blog at www.thetwentiminutevc.com. And finally, what was your most recent investment and why you said yes?

A Uh, most recent investment and why we said yes, um, Most recent investment was in, uh, so we did a, done a, a number of them recently, but, uh, it was Hello Giggles, and why we said yes, um, was because of the power of what they'd achieved on no money at the end of the day, um, and they'd gone from zero to fifteen million uniques with no capital, um, Based on a narrative, and again, I go back to narrative and story, of Zooey Deschanel as she came into Hollywood and Um, and was being torn apart by, uh, you know, getting press for how she dressed, and a lot of snipey and negativity, and she said, I want a place where women can have a positive place to talk about important things in their life, and that was the genesis of, uh, Hello Giggles, which, you know, is a, uh, maybe a, a, uh, Uh, you know, people sometimes scratch their name on, you know, their head regarding the name, but, um, at this point, they are, um, uh, one of the largest sites for women, represent a huge portion of Refinery 29 traffic, and, uh, I just love the, when you have a, a situation like that where, um, uh, uh, A strong mission and purpose drives a company with a strong narrative to growth in a very efficient manner. Um, the other, another deal that we recently did, um, it's coming called Viv, V-I-V. Um, and it's, uh, next generation Siri. It's Dag and his team who, um, were the founders of Siri.

AI assessment note: “Most recent investment was in... Hello Giggles, and why we said yes”

Q Now, when investing in a startup, what's your normal investment size?

A So we have, the advantage we have is with the Pritzke Group, we have a seven billion dollar, uh, evergreen pool of capital to invest off of. So our core investment focus is series A and B, and that's, you know, four to ten million dollars on the downstroke, but we have a very active seed program we use strategically. Um, it, uh, you know, so that can be as little as two 50 or a 100,000, but really our core focus is that, but Because of our capital base, once we're in, we have the ability to run with a company all the way. So, uh, we've written up to sixty million dollars into a deal. Um, one of my companies, SMS Assist, um, we put fifteen million in. The company was doing well, needed another forty-five million, and we wrote the check. And so we've got the flexibility to do that, but again, we're not stage agnostic. Um, we are A, B investors, but we've got, uh, flexibility to support our companies, especially Um, we might talk a little bit later about, uh, where we are in the cycle, but if there's a, a, or when there's a downturn in the market, you know, we've got the ability to protect our companies because we don't have a fund per se.

AI assessment note: “our core investment focus is series A and B, and that's, you know, four to ten million”

Q And again, if our listeners are lucky enough to have read your blog, it's, it's clear that you love your commencement speeches. What is that? And are there any that you'd recommend To, to our audience.

A Yeah. I mean, I would say that the, the granddaddy of, of, of commencement speeches is obviously Steve Jobs's speech, which was absolutely incredible. Um, what I think is wonderful about commencement speeches is it's a good commencement speech is someone looking at their life, um, pulling the nuggets and insights from it, putting an inspirational wrap around it, And in a very short window or period of time, communicating their very essence in many cases, um, to the next generation of students. And, uh, so it's very powerful. Um, there was an, another one that I have on my website, um, It was, uh, Admiral, uh, I'm blanking on his name now. You can find it on my website, the VC Confidential, which was incredibly powerful.

AI assessment note: “granddaddy of, of, of commencement speeches is obviously Steve Jobs's speech”

Q And again, if our listeners are lucky enough to have read your blog, it's, it's clear that you love your commencement speeches. What is that? And are there any that you'd recommend To, to our audience.

A Yeah. I mean, I would say that the, the granddaddy of, of, of commencement speeches is obviously Steve Jobs's speech, which was absolutely incredible. Um, what I think is wonderful about commencement speeches is it's a good commencement speech is someone looking at their life, um, pulling the nuggets and insights from it, putting an inspirational wrap around it, And in a very short window or period of time, communicating their very essence in many cases, um, to the next generation of students. And, uh, so it's very powerful. Um, there was an, another one that I have on my website, um, It was, uh, Admiral, uh, I'm blanking on his name now. You can find it on my website, the VC Confidential, which was incredibly powerful.

AI assessment note: “granddaddy of, of, of commencement speeches is obviously Steve Jobs's speech”

Q Now, when investing in a startup, what's your normal investment size?

A So we have, the advantage we have is with the Pritzke Group, we have a seven billion dollar, uh, evergreen pool of capital to invest off of. So our core investment focus is series A and B, and that's, you know, four to ten million dollars on the downstroke, but we have a very active seed program we use strategically. Um, it, uh, you know, so that can be as little as two 50 or a 100,000, but really our core focus is that, but Because of our capital base, once we're in, we have the ability to run with a company all the way. So, uh, we've written up to sixty million dollars into a deal. Um, one of my companies, SMS Assist, um, we put fifteen million in. The company was doing well, needed another forty-five million, and we wrote the check. And so we've got the flexibility to do that, but again, we're not stage agnostic. Um, we are A, B investors, but we've got, uh, flexibility to support our companies, especially Um, we might talk a little bit later about, uh, where we are in the cycle, but if there's a, a, or when there's a downturn in the market, you know, we've got the ability to protect our companies because we don't have a fund per se.

AI assessment note: “four to ten million dollars on the downstroke, but we have a very active seed”

Q What book or resource would you recommend to an aspiring founder?

A What book a resource would you recommend? Ah, no, there's always the generic, uh, you know, Eric Reese, um, yeah, lean startup is always good. Number one predictor of success, um, is amount of capital raised. Um, I would also say one of the books on narrative, um, Stephen King has a great book that, uh, he did on, uh, on narrative, um, Uh, let's see if I can, I can actually pull a couple of these up here very quickly, but I believe at the end of the day, venture is about storytelling, as we just talked about, and, um, uh, I'll just pull a couple of these names up here. Um, these are the kind of well-known narrative books that people in Hollywood will use, uh, Klinkenborg, uh, it's called Several Short Sentences About Writing, uh, Um, down to, uh, writing down the bones by Natalie Goldberg. Um, this one's a great one. Stephen King on how he writes on writing, um, a memoir of the craft. And then last but not least, it's, uh, well, uh, Robert McKee. This one, a lot of people in Hollywood use M C K E E story, substance, structure, and style. And then, uh, near and dear to me, it's a long book, but very powerful. It's called The Writer's Journey, Mythical Structures for Writers.

AI assessment note: “Eric Reese, um, yeah, lean startup is always good.”

Q Okay, absolutely. Um, honing a little on your personal investment strategy, you've been named to the always on top a hundred VCs list, leading me to ask, how's your investment strategy changed over the years, do you think?

A Um, You know, I think that every year, the, every year I'm convinced that I've learned everything I need about venture capital, and every year I realize that I'm still in third grade. Okay. So what happens is, as you go through market cycles, uh, there are large, uh, sector trends, things moving, for example, the rise of the millennials, the rise of female entrepreneurs, um, you know, the, the, the crash in They force you to reevaluate how you think about investing. What I would say is that where we've made, where I've made my most money over the years is by backing, um, authentic, um, uh, passionate entrepreneurs where there's open communication and trust. So no matter what happens at the end of the day, um, That is the most important thing I tell all of my, uh, associates and VPs is you have to protect that trust and communication. So that's the first thing. Um, where I've always ended up getting into trouble is where I convince myself that it's not that important and the opportunity is really, really good. The second is, um, someone who, um, Is, got, uh, a strong sense of purpose and mission, but more importantly, as it relates to the domain that they're going into. So they, they know the nuances of the domain, and they can zig and zag as need be, um, at the end of the day. That, I think, is, is critical. And then when you look back at it, the thing that, you know, right now…

AI assessment note: “They force you to reevaluate how you think about investing.”

Q So now on your blog, you've written about the 15 year tech cycle and you've quoted Steve Tubertson If you can see it, it isn't the revolution. Leading me to ask, where do you stand on a tech bubble? Is it occurring now? And, and why do you think that?

A So, um, I'd say I'm a, I'm a horrible forecaster, but, but the good news is from time to time I do blog posts just to at least put my stake in the ground. So I did a blog post in June, 2008 saying that the venture cycle was done, um, and to get ready for the winter. And then another one in November, 2008 saying, uh, you know, start, uh, start investing. And the reason was in 2008, it was, uh, in one week, um, all of the term sheets from West Coast firms in Chicago vaporized. And so what I like to say is that As you get deeper and deeper into a cycle, people move into either geographies or sectors or types of investors come into the market that normally don't until it feels like the world's risk free. Right? Absolutely. Um, and in one week, all the term sheets into Chicago, which the Valley guys hate flying to Chicago because it's a four hour, four and a half hour flight into the snow into O'Hare. Um, but you know that they've so overfished their own market, they'll, they'll stretch to Poland and, and wherever they can to find deals. But then what'll happen is you'll start to see a pullback. We haven't seen that quite yet. Um, and so, and also everyone's waiting for a market crash, so I don't think we're going to see a market crash until people are tired waiting for it. Um, but I will tell you that we've been thinking of creating a, uh, a Google Doc of yet another sign that we'v…

AI assessment note: “these are all signs that were late on the stage.”

Q So now on your blog, you've written about the 15 year tech cycle and you've quoted Steve Tubertson If you can see it, it isn't the revolution. Leading me to ask, where do you stand on a tech bubble? Is it occurring now? And, and why do you think that?

A So, um, I'd say I'm a, I'm a horrible forecaster, but, but the good news is from time to time I do blog posts just to at least put my stake in the ground. So I did a blog post in June, 2008 saying that the venture cycle was done, um, and to get ready for the winter. And then another one in November, 2008 saying, uh, you know, start, uh, start investing. And the reason was in 2008, it was, uh, in one week, um, all of the term sheets from West Coast firms in Chicago vaporized. And so what I like to say is that As you get deeper and deeper into a cycle, people move into either geographies or sectors or types of investors come into the market that normally don't until it feels like the world's risk free. Right? Absolutely. Um, and in one week, all the term sheets into Chicago, which the Valley guys hate flying to Chicago because it's a four hour, four and a half hour flight into the snow into O'Hare. Um, but you know that they've so overfished their own market, they'll, they'll stretch to Poland and, and wherever they can to find deals. But then what'll happen is you'll start to see a pullback. We haven't seen that quite yet. Um, and so, and also everyone's waiting for a market crash, so I don't think we're going to see a market crash until people are tired waiting for it. Um, but I will tell you that we've been thinking of creating a, uh, a Google Doc of yet another sign that we'v…

AI assessment note: “these are all signs that were late on the stage.”

Q Okay, absolutely. Um, honing a little on your personal investment strategy, you've been named to the always on top a hundred VCs list, leading me to ask, how's your investment strategy changed over the years, do you think?

A Um, You know, I think that every year, the, every year I'm convinced that I've learned everything I need about venture capital, and every year I realize that I'm still in third grade. Okay. So what happens is, as you go through market cycles, uh, there are large, uh, sector trends, things moving, for example, the rise of the millennials, the rise of female entrepreneurs, um, you know, the, the, the crash in They force you to reevaluate how you think about investing. What I would say is that where we've made, where I've made my most money over the years is by backing, um, authentic, um, uh, passionate entrepreneurs where there's open communication and trust. So no matter what happens at the end of the day, um, That is the most important thing I tell all of my, uh, associates and VPs is you have to protect that trust and communication. So that's the first thing. Um, where I've always ended up getting into trouble is where I convince myself that it's not that important and the opportunity is really, really good. The second is, um, someone who, um, Is, got, uh, a strong sense of purpose and mission, but more importantly, as it relates to the domain that they're going into. So they, they know the nuances of the domain, and they can zig and zag as need be, um, at the end of the day. That, I think, is, is critical. And then when you look back at it, the thing that, you know, right now…

AI assessment note: “as you go through market cycles... force you to reevaluate how you think about investing”