Every argument clarity score on this site is built from rows on this page. Each
question and answer was assessed with names hidden, the host's own answers included, on
four things from 1 to 5:
directness (does it answer the question asked), coherence (do the ideas follow),
precision (concrete details and clear references), compression (says a lot per word). The weighted
mix (30/30/25/15) is the exchange score. A person's published score averages their exchange
scores on raw tape only, at least 8 of them, shrunk toward the cohort mean.
Full method →
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Fast Company once called you, uh, you said you make Jack Dorsey look lazy. Uh, you must have loved that one. So what are your productivity hacks and tactics then?
A So I, I think when that article came out, uh, I, I, I definitely wasn't true, uh, but it was, it was quite the lead. Um, I, I think there's two things that I do right now that help me to optimize my time so I can fit more in. One is, uh, meeting lengths. I always try to schedule meetings for either 25 or 50 minutes, leaving me the buffer to do whatever the follow-up tasks are so I'm not back to back to back. Um, and so giving myself 10 minutes after a fifty-minute meeting means I can send off that intro email, I can write up a summary, send it to my partners, you know, whatever it takes. The other thing I would say is that I am terrible at taking notes. However, I am great at tweeting. And so what I learned was I should send myself notes in sort of 140 character chunks. It's something I'm, I'm good at kind of compacting those things that I'm thinking about down to that. And so I actually send myself the email and it is very short, 140 to 160 character little blurbs after every conversation I have. Uh, and that's been a lot better than not taking notes at all.
AI assessment note: “there's two things that I do right now that help me to optimize my time”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q And you said absolutely, you know, venture is a business. So as a venture investor now and part of that business, you've previously said kind of what makes great VCs is Is there ability to spot patterns? Um, so talk to me about now and how you look to develop pattern recognition as a new venture investor.
A Well, first things first, I think I'll listen a lot. The Definitely listening. It'll be listening to pitches, but it'll also be listening to other investors, people we've invested with, people we might like to. Definitely listening to my partners who are all 15 plus years older than I am with 20 years of venture experience each. Um, I, you know, my two months kind of are, are just the beginning. Um, so I think there's a lot of, there's a lot of listening. There's also, we actually have a lot of data. Flybridge has been around for 15 years. In, in our deal flow product, we have We've documented over 19,000 companies that we've looked at. That's an incredible number. I mean, I, I wouldn't have guessed that if you would have asked me before I joined and over the years of flybridge funds, one through four, we've backed about 80 companies. So I think as I slowly make my way through a deal flow and I take it a piece at a time or a category at a time, I can start to ask questions and learn about what people saw or didn't see in a company that Whether they did or didn't back it. And I think everybody has their, you know, anti portfolio. Some are larger than others. Some, some funds are very public about it, but ultimately both the companies that won and the ones that didn't can both provide me a lot of insight. And eventually I'll start to be able to kind of pick these things out on my…
AI assessment note: “I think I'll listen a lot... There's also, we actually have a lot of data.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q And then favorite blog or newsletter. What are your must reads?
A Every morning, uh, I read the skim. It's one way that I feel a little bit smarter. Uh, and I think that's, I think that's the goal of it. Uh, the other one that I've more recently started following, it's not really a blog or newsletter, but it's a startup that's actually in tech stars, this disco around called purple. And it's a, a bot that actually teaches me today about the election through really, really sort of concise, uh, Simple, but personable conversational things around sort of what's happening both on the Hillary side and the Trump side. And for me, you know, being kind of as busy as I am every day, it's great to be able to see that kind of twice a day when the messages come in.
AI assessment note: “Every morning, uh, I read the skim.”
Answered raw tape
D 5 · C 5 · P 5 · Cm 4 4.85
Q Fast Company once called you, uh, you said you make Jack Dorsey look lazy. Uh, you must have loved that one. So what are your productivity hacks and tactics then?
A So I, I think when that article came out, uh, I, I, I definitely wasn't true, uh, but it was, it was quite the lead. Um, I, I think there's two things that I do right now that help me to optimize my time so I can fit more in. One is, uh, meeting lengths. I always try to schedule meetings for either 25 or 50 minutes, leaving me the buffer to do whatever the follow-up tasks are so I'm not back to back to back. Um, and so giving myself 10 minutes after a fifty-minute meeting means I can send off that intro email, I can write up a summary, send it to my partners, you know, whatever it takes. The other thing I would say is that I am terrible at taking notes. However, I am great at tweeting. And so what I learned was I should send myself notes in sort of 140 character chunks. It's something I'm, I'm good at kind of compacting those things that I'm thinking about down to that. And so I actually send myself the email and it is very short, 140 to 160 character little blurbs after every conversation I have. Uh, and that's been a lot better than not taking notes at all.
AI assessment note: “two things that I do right now that help me to optimize my time”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q That's such a good segue into, into the question that I'm about to ask in terms of the WeWork experience, and what was the biggest takeaway that you've taken with you now to your time as an investor with Flybridge? What was it from operations that you've taken?
A I think the thing that I realize is that, so the venture world is a business of, of outliers, right? The, of Fund could return, and I've heard you talk about this with other investors on the show, you know, funds will return all different amounts, but if you wind up backing one Uber, one WeWork, one Airbnb, uh, one Facebook, you know, that's, that's, you know, that's the winner. That's the big thing there. What I realized through being at WeWork and having talked to thousands of companies over the last number of years is that the companies that tend to, the operators that tend to be the most successful, uh, Um, tend to be the ones that are just amazing at putting their heads down, not trying to do everything at one time, but being capable of doing everything at one time. And the reason it's important is that in the earliest days of a, of a company, you actually don't know when your first customer might come along or when your first, uh, you know, God forbid problem in the company happens. Uh, some servers go down and, and now you're getting terrible calls at three in the morning being yelled at. Um, you need to be able to turn on to every one of those roles on a dime, and I think my time at WeWork was spent, I guess, six official roles during my time that I was there, but I probably worked on 10 different groups during that time, and that actually spanned from everything from b…
AI assessment note: “now that I'm on the venture side, I would say that I am absolutely looking”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q And you said absolutely, you know, venture is a business. So as a venture investor now and part of that business, you've previously said kind of what makes great VCs is Is there ability to spot patterns? Um, so talk to me about now and how you look to develop pattern recognition as a new venture investor.
A Well, first things first, I think I'll listen a lot. The Definitely listening. It'll be listening to pitches, but it'll also be listening to other investors, people we've invested with, people we might like to. Definitely listening to my partners who are all 15 plus years older than I am with 20 years of venture experience each. Um, I, you know, my two months kind of are, are just the beginning. Um, so I think there's a lot of, there's a lot of listening. There's also, we actually have a lot of data. Flybridge has been around for 15 years. In, in our deal flow product, we have We've documented over 19,000 companies that we've looked at. That's an incredible number. I mean, I, I wouldn't have guessed that if you would have asked me before I joined and over the years of flybridge funds, one through four, we've backed about 80 companies. So I think as I slowly make my way through a deal flow and I take it a piece at a time or a category at a time, I can start to ask questions and learn about what people saw or didn't see in a company that Whether they did or didn't back it. And I think everybody has their, you know, anti portfolio. Some are larger than others. Some, some funds are very public about it, but ultimately both the companies that won and the ones that didn't can both provide me a lot of insight. And eventually I'll start to be able to kind of pick these things out on my…
AI assessment note: “learn about what people saw or didn't see in a company”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Do you think you'll miss being in the weeds? I mean, some investors play very active roles, um, with portfolio companies, even in the weeds to an extent. Um, so, so do you think you'll miss that element?
A Uh, it's a good question. I spent 10 years as an operator across being a, you know, a network security consultant through being in a public company through starting startups. I will say that I don't miss it today. I may miss it in the future. I think the nice thing about what I'm doing now and with my partners here at Flybridge is that we are able to invest kind of across the spectrum from, you know, relatively early seed, a 250,000 dollar check on up. And because of that, I will get the opportunity to invest in and to participate in very actively at the earliest stages of a company. The question that I sort of ask myself is, as a company grows and it becomes more successful, the question for me is whether or not not playing an active role in those major decisions post Series A or Series B becomes something that I miss. And the lucky thing for me is, That will probably take me a couple of years to have to face that problem. Uh, when I'm investing in a company at a, at a seed stage, you know, I will get the opportunity to really sit in the room, whiteboard on ideas, and, and really work through the challenges, uh, that they're facing with them, and ultimately, I do think that'll be as much as I want to get into the weeds today, and, and I'll learn over time if it's something that I, I really need to get back into.
AI assessment note: “I will say that I don't miss it today. I may miss it in the future.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q And then favorite blog or newsletter. What are your must reads?
A Every morning, uh, I read the skim. It's one way that I feel a little bit smarter. Uh, and I think that's, I think that's the goal of it. Uh, the other one that I've more recently started following, it's not really a blog or newsletter, but it's a startup that's actually in tech stars, this disco around called purple. And it's a, a bot that actually teaches me today about the election through really, really sort of concise, uh, Simple, but personable conversational things around sort of what's happening both on the Hillary side and the Trump side. And for me, you know, being kind of as busy as I am every day, it's great to be able to see that kind of twice a day when the messages come in.
AI assessment note: “Every morning, uh, I read the skim.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q That's such a good segue into, into the question that I'm about to ask in terms of the WeWork experience, and what was the biggest takeaway that you've taken with you now to your time as an investor with Flybridge? What was it from operations that you've taken?
A I think the thing that I realize is that, so the venture world is a business of, of outliers, right? The, of Fund could return, and I've heard you talk about this with other investors on the show, you know, funds will return all different amounts, but if you wind up backing one Uber, one WeWork, one Airbnb, uh, one Facebook, you know, that's, that's, you know, that's the winner. That's the big thing there. What I realized through being at WeWork and having talked to thousands of companies over the last number of years is that the companies that tend to, the operators that tend to be the most successful, uh, Um, tend to be the ones that are just amazing at putting their heads down, not trying to do everything at one time, but being capable of doing everything at one time. And the reason it's important is that in the earliest days of a, of a company, you actually don't know when your first customer might come along or when your first, uh, you know, God forbid problem in the company happens. Uh, some servers go down and, and now you're getting terrible calls at three in the morning being yelled at. Um, you need to be able to turn on to every one of those roles on a dime, and I think my time at WeWork was spent, I guess, six official roles during my time that I was there, but I probably worked on 10 different groups during that time, and that actually spanned from everything from b…
AI assessment note: “now that I'm on the venture side, I would say that I am absolutely looking for”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Do you think you'll miss being in the weeds? I mean, some investors play very active roles, um, with portfolio companies, even in the weeds to an extent. Um, so, so do you think you'll miss that element?
A Uh, it's a good question. I spent 10 years as an operator across being a, you know, a network security consultant through being in a public company through starting startups. I will say that I don't miss it today. I may miss it in the future. I think the nice thing about what I'm doing now and with my partners here at Flybridge is that we are able to invest kind of across the spectrum from, you know, relatively early seed, a 250,000 dollar check on up. And because of that, I will get the opportunity to invest in and to participate in very actively at the earliest stages of a company. The question that I sort of ask myself is, as a company grows and it becomes more successful, the question for me is whether or not not playing an active role in those major decisions post Series A or Series B becomes something that I miss. And the lucky thing for me is, That will probably take me a couple of years to have to face that problem. Uh, when I'm investing in a company at a, at a seed stage, you know, I will get the opportunity to really sit in the room, whiteboard on ideas, and, and really work through the challenges, uh, that they're facing with them, and ultimately, I do think that'll be as much as I want to get into the weeds today, and, and I'll learn over time if it's something that I, I really need to get back into.
AI assessment note: “I will say that I don't miss it today. I may miss it in the future.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q the fan, so to speak, for the first time with my business, and other than weeping on the floor for hours, uh, I had to kind of deal with a big problem for the first time. I'm really intrigued, how, how do you deal with big problems when the shit hits the fan? How do you approach it mentality-wise and, and get up and try to move on from it?
A Yeah, I think there's one major thing that I probably do when, when kind of to your point, the shit hits the fan. And I think that is, I try to kind of look at what the problem is at face value. And I try and say, this could be worse. First off, it could always be worse. But the other thing is, the question is, what kind of an opportunity arises when you have that problem? So when your site is down, you know, for you, the thought may go through your head first, you know, But the second thing may be, oh, well, this gives me a great opportunity to kind of think about how I make this better for the future, and I think that, you know, we had many stories in the earliest days of WeWork where we, we didn't have power for a floor for whatever reason, and you learn really amazing things about your customers and, and for us, our members. In that moment, a story that I can't think about is, is the way that our members handled when we moved to our second We work labs location, which was on Varick street. And we walked into the building on opening day and construction wasn't done. We had 220 people that were going to move into this floor and, and they couldn't move in on opening day. You know, we fortunately don't have this problem anymore. Uh, however, what was amazing to me was we actually not only were able to kind of smooth it over, and I think we took everybody out to the bar maybe, a…
AI assessment note: “I try and say, this could be worse. First off, it could always be worse.”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q entrepreneurs there. And you said earlier about WeWork's, uh, insane vision, uh, from the start. Um, I'm really intrigued at what stage is vision actually stubbornness, you know, say Kevin's system, uh, with bourbon, it's really cleverly, um, pivoted to law to Instagram. Um, If he had an unwavering vision with Bourbon, he would never have done the pivot. At what stage is then, um, vision stubbornness, do you think?
A Well, look, I wish there was a perfect formula for it, but I think that I, I wrote something, I think it was a couple years ago now, about kind of it being really important to have a hypothesis. In order to prove whether or not your hypothesis is correct, you have to have one, right? It's pretty simple. I think that the vision matters from day one, because you need to know that if things go well, Where sort of the goal line is, where the end goal is. The other reason to have the vision and to have this hypothesis as to where that vision is going to be is you also need to pay attention to sort of the signals around you. And when you start to learn that either that vision is incorrect, that hypothesis that you had about the business that you're entering isn't correct. You need to be able to take a step back, and so great founders both need to be visionary and stubborn, to your point, but also have to be self-reflective and have to be able to kind of look at what's happening around them and look at both the market and their team and their company and their customers and be able to actually say, wait, I think that vision needs to be put on hold. I think it needs to be shifted a bit. Sometimes shifted a bit could be a massive Shift, like, you know, bourbon to Instagram. Uh, and, and in other cases, you know, it's just a little tweak on the model. It's, you know, we thought we were g…
AI assessment note: “great founders both need to be visionary and stubborn... but also have to be self-reflective”
Answered raw tape
D 5 · C 5 · P 4 · Cm 4 4.60
Q Basically you're like AI. You're just processing data from machine learning and I love it. Um, but I, I do want to ask, and this sounds very amateur, but it's, it's an interesting one for me is, is venture everything you expected it to be? Did you have a preconceived idea?
A It's a great question. I think that I didn't know exactly what to expect sitting on this side of the table. I think what I did realize is that I am extraordinarily excited to be doing this thing that I believe I really enjoy doing. And in all honesty, I Knowing if you're any good at venture takes, you know, five years, seven years, sometimes 10 years, so I can't really speak for if I'm But what is really interesting is that there's a, there's a fundamental shift in how this business operates versus any other business I've been in. And while I understood the shift or the change or the difference, I, I don't think I could really grasp how large that was. And that, that change is that you go from a business where every decision you make every single day could affect change in the To run a marketing campaign at WeWork, let's say, and by tomorrow, we could see results. In the venture world, it is a, it is a slow-moving business. It's not to say, you know, we as a fund make decisions relatively quickly, but those decisions that are made tend to take years to sort of see the outcomes from, and even when you sit at a board meeting, you know, every quarter, you might make choices, but you're not down in the weeds every day, and so I think for me, It's everything I expected it would be, but there, that, that major mind shift is something that I'm still getting used to. And I, I love, I l…
AI assessment note: “It's everything I expected it would be, but there, that, that major mind shift”
Answered raw tape
D 5 · C 5 · P 4 · Cm 3 4.45
Q Basically you're like AI. You're just processing data from machine learning and I love it. Um, but I, I do want to ask, and this sounds very amateur, but it's, it's an interesting one for me is, is venture everything you expected it to be? Did you have a preconceived idea?
A It's a great question. I think that I didn't know exactly what to expect sitting on this side of the table. I think what I did realize is that I am extraordinarily excited to be doing this thing that I believe I really enjoy doing. And in all honesty, I Knowing if you're any good at venture takes, you know, five years, seven years, sometimes 10 years, so I can't really speak for if I'm But what is really interesting is that there's a, there's a fundamental shift in how this business operates versus any other business I've been in. And while I understood the shift or the change or the difference, I, I don't think I could really grasp how large that was. And that, that change is that you go from a business where every decision you make every single day could affect change in the To run a marketing campaign at WeWork, let's say, and by tomorrow, we could see results. In the venture world, it is a, it is a slow-moving business. It's not to say, you know, we as a fund make decisions relatively quickly, but those decisions that are made tend to take years to sort of see the outcomes from, and even when you sit at a board meeting, you know, every quarter, you might make choices, but you're not down in the weeds every day, and so I think for me, It's everything I expected it would be, but there, that, that major mind shift is something that I'm still getting used to. And I, I love, I l…
AI assessment note: “It's everything I expected it would be, but there, that, that major mind shift”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q the fan, so to speak, for the first time with my business, and other than weeping on the floor for hours, uh, I had to kind of deal with a big problem for the first time. I'm really intrigued, how, how do you deal with big problems when the shit hits the fan? How do you approach it mentality-wise and, and get up and try to move on from it?
A Yeah, I think there's one major thing that I probably do when, when kind of to your point, the shit hits the fan. And I think that is, I try to kind of look at what the problem is at face value. And I try and say, this could be worse. First off, it could always be worse. But the other thing is, the question is, what kind of an opportunity arises when you have that problem? So when your site is down, you know, for you, the thought may go through your head first, you know, But the second thing may be, oh, well, this gives me a great opportunity to kind of think about how I make this better for the future, and I think that, you know, we had many stories in the earliest days of WeWork where we, we didn't have power for a floor for whatever reason, and you learn really amazing things about your customers and, and for us, our members. In that moment, a story that I can't think about is, is the way that our members handled when we moved to our second We work labs location, which was on Varick street. And we walked into the building on opening day and construction wasn't done. We had 220 people that were going to move into this floor and, and they couldn't move in on opening day. You know, we fortunately don't have this problem anymore. Uh, however, what was amazing to me was we actually not only were able to kind of smooth it over, and I think we took everybody out to the bar maybe, a…
AI assessment note: “what kind of an opportunity arises when you have that problem?”
Answered raw tape
D 4 · C 5 · P 4 · Cm 4 4.30
Q entrepreneurs there. And you said earlier about WeWork's, uh, insane vision, uh, from the start. Um, I'm really intrigued at what stage is vision actually stubbornness, you know, say Kevin's system, uh, with bourbon, it's really cleverly, um, pivoted to law to Instagram. Um, If he had an unwavering vision with Bourbon, he would never have done the pivot. At what stage is then, um, vision stubbornness, do you think?
A Well, look, I wish there was a perfect formula for it, but I think that I, I wrote something, I think it was a couple years ago now, about kind of it being really important to have a hypothesis. In order to prove whether or not your hypothesis is correct, you have to have one, right? It's pretty simple. I think that the vision matters from day one, because you need to know that if things go well, Where sort of the goal line is, where the end goal is. The other reason to have the vision and to have this hypothesis as to where that vision is going to be is you also need to pay attention to sort of the signals around you. And when you start to learn that either that vision is incorrect, that hypothesis that you had about the business that you're entering isn't correct. You need to be able to take a step back, and so great founders both need to be visionary and stubborn, to your point, but also have to be self-reflective and have to be able to kind of look at what's happening around them and look at both the market and their team and their company and their customers and be able to actually say, wait, I think that vision needs to be put on hold. I think it needs to be shifted a bit. Sometimes shifted a bit could be a massive Shift, like, you know, bourbon to Instagram. Uh, and, and in other cases, you know, it's just a little tweak on the model. It's, you know, we thought we were g…
AI assessment note: “great founders both need to be visionary and stubborn, to your point, but also have to be self-reflective”
Answered raw tape
D 5 · C 4 · P 4 · Cm 4 4.30
Q And I'm so pleased you mentioned the fiscal duty there of being a venture investor as opposed to an angel investor, because I'd love to hear about how that transitioned for you. Now you're a venture investor with fiduciary responsibility. Have you seen a mindset shift in your investment patterns?
A Yeah, I mean, I think that as I looked at doing my first deal, which we haven't announced yet, I definitely had to put on a slightly different lens, and I think the biggest thing is what I was talking about earlier, that it's a business of kind of outliers, and so I actually asked my partners this question, which was, I saw this company that we were looking at, and I felt unwavering belief based on my history that That this company could be a billion-dollar company or more, right? This is sort of the line. You're a seed investor, and you're going to get diluted later on in rounds if these companies do really well. You want to make sure that there's enough ownership, that it's worthwhile, and that ultimately, if it's big enough, it can pay back the whole fund, or it's, it could be the one winner. I had this view, this vision, that, that, and this deep-seated belief that this company was one of those companies. And I asked my partners, I said, You know, how often do we feel this way? Like, how often did the first investors in Uber or Airbnb or WeWork, you know, feel the way that I'm feeling now? And I think the answer is it's, it's a mixed bag. I think sometimes you feel stronger than others, but what I realized in the process and what I learned from my partners and others in the industry is that that's probably one of the biggest changes from being a personal investor to being a…
AI assessment note: “that's probably one of the biggest changes from being a personal investor to being a venture investor”
Answered raw tape
D 5 · C 4 · P 4 · Cm 3 4.15
Q Do you intend to, um, apply that same internal dialogue with founders then, now as an investor, when things aren't going right, you know, maybe they're raising a follow-on round, and the product market fits just not there, and it doesn't seem right. Do you, as an investor, how do you approach that situation, do you think, going forward?
A I very much hope that I do approach it the same way. I can tell you, sort of, anecdotally, uh, one company in, in my personal angel portfolio, which is Currently, 15 companies, you know, was struggling at a point before they ultimately did shut down, and I think one of the things that I kind of shared with them was, as your investor, and as your friend, and as your advisor, my goal should be to try to help you to be the most successful you could be, and as an angel, it's slightly different than venture because it's your own personal capital, and so you can decide kind of on your own, or I could decide on my own, How much that mattered to me if I lost that capital or not when there's other people's money involved, you know, there's a different kind of fiscal duty, but I think that the story is still the same, which is you're trying to make sure that you help people to be the best that they can be. And ultimately giving hard or critical feedback in, in a, in a friendly and helpful way is, is definitely an acquired skill. It's something that takes time. I think my time as an operator across, you know, public companies and private managing all different people, people that were local and people internationally helped me a lot early on to kind of understand the cultural differences and allowed me to kind of have those more difficult conversations. And I, I really do hope that I, and…
AI assessment note: “I very much hope that I do approach it the same way.”
Answered raw tape
D 5 · C 4 · P 4 · Cm 3 4.15
Q And I'm so pleased you mentioned the fiscal duty there of being a venture investor as opposed to an angel investor, because I'd love to hear about how that transitioned for you. Now you're a venture investor with fiduciary responsibility. Have you seen a mindset shift in your investment patterns?
A Yeah, I mean, I think that as I looked at doing my first deal, which we haven't announced yet, I definitely had to put on a slightly different lens, and I think the biggest thing is what I was talking about earlier, that it's a business of kind of outliers, and so I actually asked my partners this question, which was, I saw this company that we were looking at, and I felt unwavering belief based on my history that That this company could be a billion-dollar company or more, right? This is sort of the line. You're a seed investor, and you're going to get diluted later on in rounds if these companies do really well. You want to make sure that there's enough ownership, that it's worthwhile, and that ultimately, if it's big enough, it can pay back the whole fund, or it's, it could be the one winner. I had this view, this vision, that, that, and this deep-seated belief that this company was one of those companies. And I asked my partners, I said, You know, how often do we feel this way? Like, how often did the first investors in Uber or Airbnb or WeWork, you know, feel the way that I'm feeling now? And I think the answer is it's, it's a mixed bag. I think sometimes you feel stronger than others, but what I realized in the process and what I learned from my partners and others in the industry is that that's probably one of the biggest changes from being a personal investor to being a…
AI assessment note: “one of the biggest changes from being a personal investor to being a venture investor”
Answered raw tape
D 5 · C 4 · P 4 · Cm 3 4.15
Q Do you intend to, um, apply that same internal dialogue with founders then, now as an investor, when things aren't going right, you know, maybe they're raising a follow-on round, and the product market fits just not there, and it doesn't seem right. Do you, as an investor, how do you approach that situation, do you think, going forward?
A I very much hope that I do approach it the same way. I can tell you, sort of, anecdotally, uh, one company in, in my personal angel portfolio, which is Currently, 15 companies, you know, was struggling at a point before they ultimately did shut down, and I think one of the things that I kind of shared with them was, as your investor, and as your friend, and as your advisor, my goal should be to try to help you to be the most successful you could be, and as an angel, it's slightly different than venture because it's your own personal capital, and so you can decide kind of on your own, or I could decide on my own, How much that mattered to me if I lost that capital or not when there's other people's money involved, you know, there's a different kind of fiscal duty, but I think that the story is still the same, which is you're trying to make sure that you help people to be the best that they can be. And ultimately giving hard or critical feedback in, in a, in a friendly and helpful way is, is definitely an acquired skill. It's something that takes time. I think my time as an operator across, you know, public companies and private managing all different people, people that were local and people internationally helped me a lot early on to kind of understand the cultural differences and allowed me to kind of have those more difficult conversations. And I, I really do hope that I, and…
AI assessment note: “I very much hope that I do approach it the same way.”
Answered raw tape
D 4 · C 4 · P 4 · Cm 3 3.85
Q And talking of the weeds, the weeds is where, Uh, most problems tend to happen, and, and as you said, you have kind of six roles in the operations with WeWork just alone. So, so I'm intrigued to hear, and you, you specialize with problem solving. So, so what kind of inherent characteristics do you think made you so good at problem solving?
A That's a great question. I actually had a conversation with my mother a couple of weeks ago. My, I have a son who's now about five and a half months old, and I, we were talking about just kind of school in New York. It's a whole Another topic. Uh, one of the things is, you know, having your child, you know, kind of tested and they do, you know, kind of aptitude tests and IQ tests and things like that. Um, and I said to my mother, I said, you know, did I ever get these tests when I was a kid? And she said, yeah, actually, when you were young, they did this aptitude test and said, well, you, well, you scored kind of in the middle of the road for mathematics and English and social studies, things like that. She said, there was this one area that they called problem solving that you scored in like the And she said, quite honestly, we had no idea what that meant, and we also had no idea what you would do with that, right, uh, later on in life. And, and what it turns out is that being a great problem solver entails kind of, I think, two things. One is being able to learn rapidly about almost any subject, and I think I've been really good at that as I face kind of each of those six roles that we work. In some cases, I was starting off from, from less than zero. I mean, I had never participated in an organization like that, and other times I had a little bit of knowledge about the indu…
AI assessment note: “being a great problem solver entails kind of, I think, two things.”
Answered raw tape
D 4 · C 4 · P 4 · Cm 3 3.85
Q And talking of the weeds, the weeds is where, Uh, most problems tend to happen, and, and as you said, you have kind of six roles in the operations with WeWork just alone. So, so I'm intrigued to hear, and you, you specialize with problem solving. So, so what kind of inherent characteristics do you think made you so good at problem solving?
A That's a great question. I actually had a conversation with my mother a couple of weeks ago. My, I have a son who's now about five and a half months old, and I, we were talking about just kind of school in New York. It's a whole Another topic. Uh, one of the things is, you know, having your child, you know, kind of tested and they do, you know, kind of aptitude tests and IQ tests and things like that. Um, and I said to my mother, I said, you know, did I ever get these tests when I was a kid? And she said, yeah, actually, when you were young, they did this aptitude test and said, well, you, well, you scored kind of in the middle of the road for mathematics and English and social studies, things like that. She said, there was this one area that they called problem solving that you scored in like the And she said, quite honestly, we had no idea what that meant, and we also had no idea what you would do with that, right, uh, later on in life. And, and what it turns out is that being a great problem solver entails kind of, I think, two things. One is being able to learn rapidly about almost any subject, and I think I've been really good at that as I face kind of each of those six roles that we work. In some cases, I was starting off from, from less than zero. I mean, I had never participated in an organization like that, and other times I had a little bit of knowledge about the indu…
AI assessment note: “being a great problem solver entails kind of, I think, two things.”