The Exchanges

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 →

Jason Mendelson argument clarity score 4.4/5 from 23 exchanges on raw tape · average scores: directness 4.7 · coherence 4.8 · precision 4.1 · compression 3.9 record → ← everyone

Every exchange below was scored with names hidden, four dimensions each from 1 to 5. An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression. The published score averages the raw tape exchange scores and shrinks small samples toward the cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only toward coarse estimates, never toward a full score.

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Answered raw tape D 5 · C 5 · P 5 · Cm 5 5.00

Q And then let's do, uh, one from Seth. Have you ever mistakenly bought an expensive scotch and charged it to your partner's room? The answer will be yes, but I want to hear the story behind it.

A Seth and I were at a bar with his wife and my girlfriend at the time, respectively. Uh, the girlfriends, uh, or the, his wife and my girlfriend wanted to order a 32 dollar glass of Flowers Pinot Noir, which we thought was obscene, and we, uh, said, why don't you focus on the 12 dollar ones? Meanwhile, we looked up and there was a Macallan 25. We had both just started drinking scotch. We had no idea that Prices went up with age. We had no idea. And we ordered two McAllen, 25 meats. We got the bill. It was 323 dollars. We about fell over. Um, our significant others were not happy that we had walked them down from their more expensive, uh, wine to drink 150 dollar glasses of scotch. So like any reasonable human being would do, we charged it to our partner, Ryan McIntyre's room, who was also staying at the hotel.

AI assessment note: “we charged it to our partner, Ryan McIntyre's room”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q It's interesting you said about the price there. I had Howard Linzen on the show the other day, and he said his biggest lesson from, from speaking to Fred Wilson was the That if price is the only thing stopping you from doing a deal, that's not a good enough reason. To what extent do you think you agree with that in terms of price being a stopping factor?

A You know, it depends. If price, if I'm the only VC talking to the entrepreneur and we're both in love, you're probably right that price shouldn't be a factor because at an early stage is early stage. You know, if we were late stage investors, totally different. It's a, it's a financial exercise at that point. But you know, Whether it's 10 pre or 15 pre, if the company's huge, we're all doing great, and if the company's a zero, it's the same result. Where I don't like to be in this situation is that there's multiple term sheets, and the entrepreneur is focused on price. Look, at the end of the day, I turn that same argument around to the entrepreneur and say, look, a couple points of ownership to anybody doesn't matter. You know, I'm not going to play this game of continually being walked up on price. Either you want to work with my firm or you don't. Totally cool if you don't. We got plenty Plenty of other companies we can invest in. So that's how I view price, you know, and I think Fred's right, but I would put the caveat I'm not going to be a price chaser at any time.

AI assessment note: “I think Fred's right, but I would put the caveat”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q It is eerily similar. I have to agree with you. Even the conference phones are exactly the same. Do you think then, That, uh, often it's stated that downtimes are the time of real innovation. Do you agree with that in the case of the fact that often the people who aren't really the lovers and the believers in the core technology leave in the downtimes?

A You know, I don't think the entrepreneurs ever go away. I think the best entrepreneurs in the world don't care about anything except pursuing their idea and pursuing their dreams. Who goes away are the venture capitalists, right? Venture capitalists in general are lemmings, and when the times are bad, they get out of the market. You know, we at Founder Group, we've been together 20 years as a team almost, and we consistently invest in the same number of deals every year because we want to be time diversified, and we don't care if the times are great or horrible. And if you look at our track record, some of the best deals we've ever done were with entrepreneurs in a down period where no other VCs would invest in them. We were able to, you know, invest in these great companies because we were the only people out there writing checks, and we had outsized returns from deals done in bad times.

AI assessment note: “I don't think the entrepreneurs ever go away. I think the best entrepreneurs”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Do you think there are any fundamentals, some pillars that are really necessary for an ecosystem to thrive? Maybe it could be a huge accelerator, like Techstars in Boulder, or, or what are the pillars that are needed to really generate that ecosystem?

A Well, I mean, the first pillar is entrepreneurs, right? You need to have a creative class of people who want to live in a particular area. Second, you need to have the support systems that support these entrepreneurs. So that's everything from From, you know, the obvious ones, which are lawyers and accountants and some venture capitalist or money that's willing to go there. But it's more importantly, the, the pillar of, of having a culture of failure is super important. I'm from Detroit. And for many years, they had creative class, they had money, they had lawyers, they had people who could work there. They had great ideas, but they lacked the ability for people to respect the culture of failure. And, you know, if you failed in Detroit, you were a failure. If your company went out of business, you were a loser in the Silicon Valley. If your company goes into the business, you're an entrepreneur. And you need to have that sort of culture infect your area in order to be able to nurture and take an entrepreneurial journey with these folks. It's also added bonus if you have a university around that's spending off ideas and smart people. Um, and it's also a bonus if you live somewhere where you can import talent from other places. Boulder is notorious for importing great people from other parts of the country who just want to live here because it's gorgeous and beautiful and wonderf…

AI assessment note: “the first pillar is entrepreneurs, right? You need to have a creative class”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q It's interesting you said about the price there. I had Howard Linzen on the show the other day, and he said his biggest lesson from, from speaking to Fred Wilson was the That if price is the only thing stopping you from doing a deal, that's not a good enough reason. To what extent do you think you agree with that in terms of price being a stopping factor?

A You know, it depends. If price, if I'm the only VC talking to the entrepreneur and we're both in love, you're probably right that price shouldn't be a factor because at an early stage is early stage. You know, if we were late stage investors, totally different. It's a, it's a financial exercise at that point. But you know, Whether it's 10 pre or 15 pre, if the company's huge, we're all doing great, and if the company's a zero, it's the same result. Where I don't like to be in this situation is that there's multiple term sheets, and the entrepreneur is focused on price. Look, at the end of the day, I turn that same argument around to the entrepreneur and say, look, a couple points of ownership to anybody doesn't matter. You know, I'm not going to play this game of continually being walked up on price. Either you want to work with my firm or you don't. Totally cool if you don't. We got plenty Plenty of other companies we can invest in. So that's how I view price, you know, and I think Fred's right, but I would put the caveat I'm not going to be a price chaser at any time.

AI assessment note: “I think Fred's right, but I would put the caveat I'm not going to”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q got a question from Brad directly related to that and your, your transition from general counsel to VC. And he asked, what was the moment that you realized that you were no longer really a general counsel and that you were actually a VC? You said there about the deal flow. Was there a defining moment you found one company in particular or one event or one specific turning point?

A Yeah, I, I remember, I don't remember the year. It was probably six years ago, seven years ago, maybe even longer. There was a point I was sitting in my office and I made the most boneheaded Lawyer mistake in the world. One that would, should get me fired. And I said, oh my God, I'm a horrible attorney. And then as I, as I had a moment of like, ah, this sucks. I've lost my skills. I thought about the 10 boards that I was on and all the entrepreneurs who I met and a couple of the companies were doing really well and just raised some new financing and one was getting sold. And I was thinking, oh, wait a minute. I, uh, you know, yeah, you shouldn't, you know, you're not a general counsel anymore. You are a venture capitalist. You know, that doesn't mean to a crappy job on the legal issues, but like you've made the transition. You, you were, Concentrating on the business, you're not concentrating on the practice of law.

AI assessment note: “made the most boneheaded Lawyer mistake in the world. One that would, should get me fired.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q You said there about investing across the US, uh, from SF to all over. I'm intrigued. When you actually make the investments, how does the deal competition differ according to the region? Is it very noticeable when you're investing in a company in SF compared to Detroit? Is that kind of intensity around the competitive nature much more?

A You know, for us, not really. I think our brand, which is ironic because we don't really try to create one, but there's four partners and there's no associates. So if you want to work with Foundry Group, We're going to work with you. You know, if we want to work together, we'll work together. We're not going to chase deals on price. We're not going to chase deals because of some other term sheet. If an entrepreneur is sincere and wants to work with us and is one of our type of people, to us, there's really no difference no matter where we go. There's probably on the margin a little more valuation creep in the Silicon Valley in New York, but it's not material.

AI assessment note: “to us, there's really no difference no matter where we go.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q How do you think then you can detect BS? Because I, I interview so many VCs and they all say, obviously I'm sure all the VCs I've interviewed are very lovely, but they all say we're founder friendly, founder first, I'm here for you. How do you detect BS in VC speak, do you think?

A For one, I look at how much money the VC Uh, firm spends on PR and marketing. We don't have a PR firm. We don't have a marketing person. Our marketing is every once in a while we lose our brains and put up a music video or write a book. And that's not marketing. It's just, we do whatever we want. And we're one of the very few venture firms, if not the only venture firm who behaves that way. I'm not saying all venture firms are bad, but in my opinion, at least 50% of them hurt entrepreneurs and 25% of them don't do any good. There's only really a quarter of the VC firms that I've worked with that really help the And frankly, um, it's amazing in a world to me where there's somewhat transparent information going on the internet that the opacity of, of reputation still exists. I, I would say just on the boards that I'm on, a good half of the VCs that I share these boards with, I don't respect. I don't think they're transparent. They've got the right buzzwords. They've been coached up to say the right things, but it's not how they act. And so I think, you know, in order to really know who the good folks are, it's really about talking to the entrepreneurs. And of course they, they don't want to go out publicly and say, oh, this guy's But if you have deep relationships with entrepreneurs, you can know pretty quickly which VCs act well and which ones don't behave the right way.

AI assessment note: “I look at how much money the VC Uh, firm spends on PR and marketing.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q You said that about respect. I'm intrigued just from a personal perspective. What makes you really respect someone, have a profound respect for someone and their mission?

A I mean, in general, I, I respect people who tell me what they're going to do and get it done and do it in a way that is on the balance good and doesn't have to require somebody else losing to win. And I think being self-aware and resilient and thoughtful and empathetic, uh, these are the types of qualities that make me respect that person. Respect is not, uh, to me, a mission statement. When I see a company that says one of our mission statements is respect for each other, I go, you know, respect is earned. It's not something that's forced upon people. And I, and to me, I, I have a set of very stringent criteria, and when people meet those criteria, I respect them, and I'm very loyal to them for a very long time.

AI assessment note: “I respect people who tell me what they're going to do and get it done”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q But I'd love to start then today with, with a topic which I know we're both very passionate about, and that's the need for transparency between entrepreneurs and VCs. So I'd love to first start with that, and where are we at today, do you think, in terms of the transparent nature of VC and entrepreneur relationships?

A I think we're sort of in a, in a local minima, if I use a math term. So if you go back in history, Through circa early 2000, certainly through 2003 or four, there was almost no transparency between entrepreneurs and venture capitalists. It was a game. It was a, what VCs can, can extract from entrepreneurs. Um, it was a very VC driven world. We had the checkbook. We had the power. There weren't a lot of, a lot of us around and it was really a travesty. You know, when Brad and I decided to write the term sheet series on the blog, um, we had two goals. One was to educate entrepreneurs and remove Some of the opacity and the fundraising process, but two, we wanted to screw over all the jerk VCs that we had met who were, who were screwing over entrepreneurs. And it was amazing that, you know, the initial feedback was very polar. The entrepreneurs loved it and the VCs, you know, skewered us and said, how dare you give away all our secrets over time, given social media, given the media's attention to venture. I mean, you know, you think about television and radio and, you know, podcasting and blogs didn't exist. You know, a little more than a decade ago. The information's gotten out there, so things become more transparent. Unfortunately, I think a lot of these tools now are being used the wrong way. There are a lot of VCs who like to claim they're transparent or say, trust me. You kno…

AI assessment note: “I think we're sort of in a, in a local minima”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q What do you think the entrepreneur needs to do then? That's from the VC perspective. What do you think the entrepreneur needs to do from the initial, uh, investment to, to really get the relationship off onto the transparent and clear footing?

A I think one of the biggest mistakes they can make is over promise and under deliver. Now that doesn't mean on everything. We all know that revenue numbers are made up, right? If we all know that getting products done on time, that's a very difficult thing, but on the expense side, you should have total control telling me what you're going to do and do it. And if you think you're off the rails, Telling me quickly, never surprising me at a board meeting. These sort of things make me feel like you're being open with me. When I come to a board meeting, and there's 40 pages of marketing materials, and then all of the problems are shoved on the last slide that they're maybe hoping we run out of time at the board meeting, that's an erosion of trust, an erosion of transparency. So I want to deal with the hard issues up front, and the most important issues up front. And in that case, if I feel like the entrepreneur is being open with me, uh, the relationship usually works really, really well.

AI assessment note: “deal with the hard issues up front, and the most important issues up front.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q Do you think there are any fundamentals, some pillars that are really necessary for an ecosystem to thrive? Maybe it could be a huge accelerator, like Techstars in Boulder, or, or what are the pillars that are needed to really generate that ecosystem?

A Well, I mean, the first pillar is entrepreneurs, right? You need to have a creative class of people who want to live in a particular area. Second, you need to have the support systems that support these entrepreneurs. So that's everything from From, you know, the obvious ones, which are lawyers and accountants and some venture capitalist or money that's willing to go there. But it's more importantly, the, the pillar of, of having a culture of failure is super important. I'm from Detroit. And for many years, they had creative class, they had money, they had lawyers, they had people who could work there. They had great ideas, but they lacked the ability for people to respect the culture of failure. And, you know, if you failed in Detroit, you were a failure. If your company went out of business, you were a loser in the Silicon Valley. If your company goes into the business, you're an entrepreneur. And you need to have that sort of culture infect your area in order to be able to nurture and take an entrepreneurial journey with these folks. It's also added bonus if you have a university around that's spending off ideas and smart people. Um, and it's also a bonus if you live somewhere where you can import talent from other places. Boulder is notorious for importing great people from other parts of the country who just want to live here because it's gorgeous and beautiful and wonderf…

AI assessment note: “the first pillar is entrepreneurs, right? You need to have a creative class”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q got a question from Brad directly related to that and your, your transition from general counsel to VC. And he asked, what was the moment that you realized that you were no longer really a general counsel and that you were actually a VC? You said there about the deal flow. Was there a defining moment you found one company in particular or one event or one specific turning point?

A Yeah, I, I remember, I don't remember the year. It was probably six years ago, seven years ago, maybe even longer. There was a point I was sitting in my office and I made the most boneheaded Lawyer mistake in the world. One that would, should get me fired. And I said, oh my God, I'm a horrible attorney. And then as I, as I had a moment of like, ah, this sucks. I've lost my skills. I thought about the 10 boards that I was on and all the entrepreneurs who I met and a couple of the companies were doing really well and just raised some new financing and one was getting sold. And I was thinking, oh, wait a minute. I, uh, you know, yeah, you shouldn't, you know, you're not a general counsel anymore. You are a venture capitalist. You know, that doesn't mean to a crappy job on the legal issues, but like you've made the transition. You, you were, Concentrating on the business, you're not concentrating on the practice of law.

AI assessment note: “I made the most boneheaded Lawyer mistake... you're not a general counsel anymore.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q You said there about investing across the US, uh, from SF to all over. I'm intrigued. When you actually make the investments, how does the deal competition differ according to the region? Is it very noticeable when you're investing in a company in SF compared to Detroit? Is that kind of intensity around the competitive nature much more?

A You know, for us, not really. I think our brand, which is ironic because we don't really try to create one, but there's four partners and there's no associates. So if you want to work with Foundry Group, We're going to work with you. You know, if we want to work together, we'll work together. We're not going to chase deals on price. We're not going to chase deals because of some other term sheet. If an entrepreneur is sincere and wants to work with us and is one of our type of people, to us, there's really no difference no matter where we go. There's probably on the margin a little more valuation creep in the Silicon Valley in New York, but it's not material.

AI assessment note: “for us, not really. I think our brand... there's really no difference”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q But I'd love to start then today with, with a topic which I know we're both very passionate about, and that's the need for transparency between entrepreneurs and VCs. So I'd love to first start with that, and where are we at today, do you think, in terms of the transparent nature of VC and entrepreneur relationships?

A I think we're sort of in a, in a local minima, if I use a math term. So if you go back in history, Through circa early 2000, certainly through 2003 or four, there was almost no transparency between entrepreneurs and venture capitalists. It was a game. It was a, what VCs can, can extract from entrepreneurs. Um, it was a very VC driven world. We had the checkbook. We had the power. There weren't a lot of, a lot of us around and it was really a travesty. You know, when Brad and I decided to write the term sheet series on the blog, um, we had two goals. One was to educate entrepreneurs and remove Some of the opacity and the fundraising process, but two, we wanted to screw over all the jerk VCs that we had met who were, who were screwing over entrepreneurs. And it was amazing that, you know, the initial feedback was very polar. The entrepreneurs loved it and the VCs, you know, skewered us and said, how dare you give away all our secrets over time, given social media, given the media's attention to venture. I mean, you know, you think about television and radio and, you know, podcasting and blogs didn't exist. You know, a little more than a decade ago. The information's gotten out there, so things become more transparent. Unfortunately, I think a lot of these tools now are being used the wrong way. There are a lot of VCs who like to claim they're transparent or say, trust me. You kno…

AI assessment note: “I think we're sort of in a, in a local minima, if I use a math term.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q You said that about respect. I'm intrigued just from a personal perspective. What makes you really respect someone, have a profound respect for someone and their mission?

A I mean, in general, I, I respect people who tell me what they're going to do and get it done and do it in a way that is on the balance good and doesn't have to require somebody else losing to win. And I think being self-aware and resilient and thoughtful and empathetic, uh, these are the types of qualities that make me respect that person. Respect is not, uh, to me, a mission statement. When I see a company that says one of our mission statements is respect for each other, I go, you know, respect is earned. It's not something that's forced upon people. And I, and to me, I, I have a set of very stringent criteria, and when people meet those criteria, I respect them, and I'm very loyal to them for a very long time.

AI assessment note: “I respect people who tell me what they're going to do and get it done”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q What do you think the entrepreneur needs to do then? That's from the VC perspective. What do you think the entrepreneur needs to do from the initial, uh, investment to, to really get the relationship off onto the transparent and clear footing?

A I think one of the biggest mistakes they can make is over promise and under deliver. Now that doesn't mean on everything. We all know that revenue numbers are made up, right? If we all know that getting products done on time, that's a very difficult thing, but on the expense side, you should have total control telling me what you're going to do and do it. And if you think you're off the rails, Telling me quickly, never surprising me at a board meeting. These sort of things make me feel like you're being open with me. When I come to a board meeting, and there's 40 pages of marketing materials, and then all of the problems are shoved on the last slide that they're maybe hoping we run out of time at the board meeting, that's an erosion of trust, an erosion of transparency. So I want to deal with the hard issues up front, and the most important issues up front. And in that case, if I feel like the entrepreneur is being open with me, uh, the relationship usually works really, really well.

AI assessment note: “telling me what you're going to do and do it. And if you think you're off the rails, Telling me quickly”

Answered raw tape D 4 · C 5 · P 4 · Cm 4 4.30

Q It is eerily similar. I have to agree with you. Even the conference phones are exactly the same. Do you think then, That, uh, often it's stated that downtimes are the time of real innovation. Do you agree with that in the case of the fact that often the people who aren't really the lovers and the believers in the core technology leave in the downtimes?

A You know, I don't think the entrepreneurs ever go away. I think the best entrepreneurs in the world don't care about anything except pursuing their idea and pursuing their dreams. Who goes away are the venture capitalists, right? Venture capitalists in general are lemmings, and when the times are bad, they get out of the market. You know, we at Founder Group, we've been together 20 years as a team almost, and we consistently invest in the same number of deals every year because we want to be time diversified, and we don't care if the times are great or horrible. And if you look at our track record, some of the best deals we've ever done were with entrepreneurs in a down period where no other VCs would invest in them. We were able to, you know, invest in these great companies because we were the only people out there writing checks, and we had outsized returns from deals done in bad times.

AI assessment note: “I don't think the entrepreneurs ever go away. [...] Who goes away are the venture capitalists”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q How do you think then you can detect BS? Because I, I interview so many VCs and they all say, obviously I'm sure all the VCs I've interviewed are very lovely, but they all say we're founder friendly, founder first, I'm here for you. How do you detect BS in VC speak, do you think?

A For one, I look at how much money the VC Uh, firm spends on PR and marketing. We don't have a PR firm. We don't have a marketing person. Our marketing is every once in a while we lose our brains and put up a music video or write a book. And that's not marketing. It's just, we do whatever we want. And we're one of the very few venture firms, if not the only venture firm who behaves that way. I'm not saying all venture firms are bad, but in my opinion, at least 50% of them hurt entrepreneurs and 25% of them don't do any good. There's only really a quarter of the VC firms that I've worked with that really help the And frankly, um, it's amazing in a world to me where there's somewhat transparent information going on the internet that the opacity of, of reputation still exists. I, I would say just on the boards that I'm on, a good half of the VCs that I share these boards with, I don't respect. I don't think they're transparent. They've got the right buzzwords. They've been coached up to say the right things, but it's not how they act. And so I think, you know, in order to really know who the good folks are, it's really about talking to the entrepreneurs. And of course they, they don't want to go out publicly and say, oh, this guy's But if you have deep relationships with entrepreneurs, you can know pretty quickly which VCs act well and which ones don't behave the right way.

AI assessment note: “For one, I look at how much money the VC Uh, firm spends on PR”

Answered raw tape D 4 · C 4 · P 3 · Cm 3 3.60

Q of the, the transparency and the clarity of relationships, I recently interviewed a founder who said that he doesn't tell his VC anything because he knows the dangers of telling the VC too much. So I'm intrigued when you make an investment, uh, how do you look to instill that relationship of clarity and trust from the very beginning? What does the core onboarding process look like in the relationship?

A Well, for me, I've decided that having no filter is both my biggest asset and my greatest curse. And it's an asset that Not having a filter that when you meet me or when you work with me, you very quickly know what I'm all about. You know what my expectations are. You know what's in my brain. At the same time, it can be off-putting to some people. Sometimes bluntness is, you know, off-putting. There's people who think I might be mean or, or, or too aggressive, but I will say for the people who I work with, I think they appreciate that they never, ever have to ask themselves, what is Jason thinking? And so if we get along The relationship becomes where I can be a mentor to them. I can be a business partner to them. I mean, look, let's be honest, being a CEO is a really lonely job. You really don't have anyone to talk to about the company. Yeah, you're gonna have some co-founders and some other people, but you're gonna have some deep, dark secrets that you're not sure who to speak to, and I really hope that we have a level of trust between myself and the entrepreneurs, given my bluntness, that we can just have an open conversation, fix the problems, and move on.

AI assessment note: “having no filter is both my biggest asset and my greatest curse”

Partly raw tape D 3 · C 4 · P 4 · Cm 3 3.55

Q I have to say, though, I'm intrigued because obviously board meetings take up a lot of time in terms of preparation and then actual attendance, and I know with you guys, you know, there's only four of you. How do you look to manage the time around boards, and what does the board to investment ratio look like for you in terms of how many boards you sit on?

A Yeah, so I'm sort of at the point, having done this for a lot of years now, where board meetings to me are spelled B-O-R-E-D. I could see a music video coming out someday about board meetings. I'd say about 25 Some of the boards I'm on run really, really well and tight where it, you know, they send out the information beforehand. There's discussion, whether it's over a Google doc or over email beforehand, and you come in and you hit the important stuff. It's efficient. It's mutually beneficial. The board meetings aren't about me or, and they're not about the outside board members. They're about all of us together, helping the entrepreneurs have a better outcome. And so long as we're all getting some mutual benefit, learning, understanding, and feeling like we're having an impact on the business, that's good. But unfortunately that's not the majority. And what you find is a lot of board cultures, uh, dumbing down to the lowest common denominator, right? There's somebody on the board who doesn't read the materials. There's somebody on the board who's not mentally engaged and the discussion quickly takes over and getting this person up to speed. And I have very little patience for that, but unfortunately it's a regular happenstance in my life.

AI assessment note: “I'd say about 25 Some of the boards I'm on run really, really well”

Partly raw tape D 3 · C 4 · P 3 · Cm 3 3.30

Q of the, the transparency and the clarity of relationships, I recently interviewed a founder who said that he doesn't tell his VC anything because he knows the dangers of telling the VC too much. So I'm intrigued when you make an investment, uh, how do you look to instill that relationship of clarity and trust from the very beginning? What does the core onboarding process look like in the relationship?

A Well, for me, I've decided that having no filter is both my biggest asset and my greatest curse. And it's an asset that Not having a filter that when you meet me or when you work with me, you very quickly know what I'm all about. You know what my expectations are. You know what's in my brain. At the same time, it can be off-putting to some people. Sometimes bluntness is, you know, off-putting. There's people who think I might be mean or, or, or too aggressive, but I will say for the people who I work with, I think they appreciate that they never, ever have to ask themselves, what is Jason thinking? And so if we get along The relationship becomes where I can be a mentor to them. I can be a business partner to them. I mean, look, let's be honest, being a CEO is a really lonely job. You really don't have anyone to talk to about the company. Yeah, you're gonna have some co-founders and some other people, but you're gonna have some deep, dark secrets that you're not sure who to speak to, and I really hope that we have a level of trust between myself and the entrepreneurs, given my bluntness, that we can just have an open conversation, fix the problems, and move on.

AI assessment note: “having no filter is both my biggest asset and my greatest curse.”

Partly raw tape D 3 · C 4 · P 3 · Cm 3 3.30

Q I have to say, though, I'm intrigued because obviously board meetings take up a lot of time in terms of preparation and then actual attendance, and I know with you guys, you know, there's only four of you. How do you look to manage the time around boards, and what does the board to investment ratio look like for you in terms of how many boards you sit on?

A Yeah, so I'm sort of at the point, having done this for a lot of years now, where board meetings to me are spelled B-O-R-E-D. I could see a music video coming out someday about board meetings. I'd say about 25 Some of the boards I'm on run really, really well and tight where it, you know, they send out the information beforehand. There's discussion, whether it's over a Google doc or over email beforehand, and you come in and you hit the important stuff. It's efficient. It's mutually beneficial. The board meetings aren't about me or, and they're not about the outside board members. They're about all of us together, helping the entrepreneurs have a better outcome. And so long as we're all getting some mutual benefit, learning, understanding, and feeling like we're having an impact on the business, that's good. But unfortunately that's not the majority. And what you find is a lot of board cultures, uh, dumbing down to the lowest common denominator, right? There's somebody on the board who doesn't read the materials. There's somebody on the board who's not mentally engaged and the discussion quickly takes over and getting this person up to speed. And I have very little patience for that, but unfortunately it's a regular happenstance in my life.

AI assessment note: “Some of the boards I'm on run really, really well and tight”

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