The Exchanges

Q I guess I'm really digging here at, like, what do you advise founders to get the most out of their board? Is it the board prep? Is it the communication that they do? Is it the Appointedness is the questions they ask. What do you advise founders to get the best out of their board?

A Communicate clearly. Communicate regularly. Communicate the wins. Communicate all of the shit sandwiches that are going on. There's not one company that doesn't have just stuff blowing up every day. Let's just say great venture investors have no problem with bad news. Our day is loaded with bad news. We have a huge problem with surprises. Don't tell me your rate. You're going to run out of money next month. Don't tell me after the fact, like three months that you lost the biggest customer. Share all of the good news, the bad news, not in a way that you're trying to paint it a certain way. And typically it comes in like, here are the wins and here's what I'm worried about. We've lost these customers. We lost these employees. Our net promoter scores down 20%, whatever it is, right? We didn't hit our revenue numbers. It also feels good because bad news is Eat you inside. If you don't get it out, if you don't share it with someone, it will just stack on top of each other, like really heavy books you don't want to read, and then eventually fall over, and either create disastrous effects for the business, or disastrous effects for your health. You know, founder depression is really a big issue, and a lot of it is because of the gap between what they think the expectations are, and the reality of their situation.

AI assessment note: “Communicate clearly. Communicate regularly. Communicate the wins.”

Q Can I ask you a bit of a weird one before we move into the quick It's like, you know, you speak with this incredible serenity and calmness, and you've just seen everything, Mike, from, you know, the incredible years building. What are your insecurities today as an investor?

A So I didn't have a ton of insecurities when we were investing out of our own balance sheet. We did about 60 deals, you know, with our own money. We never raise outside capital, and so when we decided to, you know, partner with Jim Petroni's and do Velvet Sea Ventures, you start asking yourself questions like, okay, I've gotten 250,000 to a million dollars of, like, Personal allocation for all these deals. Can we get ten million? Can we get 20? Can we get fifty million? Which is, you know, the largest deal that we've done. Are we kind of like a cute addition to the cap table, or are we like a strategic investor? Because we want to work at the highest levels of venture with the best co-investors, the best entrepreneurs. I had all these other insecurities that I hadn't felt since I started really U-Wire. At Northwestern, you know, I think everyone, no matter what they've done, you know, has this kind of imposter syndrome. And so, although I'm friends with all these VCs and I've made all this money on the investments and I was pre IPO and all these companies, including like Facebook and Tumblr and like, can I do it for a living? And so as we come out of like our first fund and we've been able to, you know, invest in companies, you know, the most important thing to me is we've product market We are people who at least 15 entrepreneurs have said, I really want you, and many of which …

AI assessment note: “Are we kind of like a cute addition to the cap table”

Q What do you do as an investor, as a board member to let me, the founder know that this is a safe space. You can tell me anything because I think it's our job to create that safe space where they feel they can tell you anything. What do you do? And what did you as an entrepreneur want from your investor to know that it was a safe space?

A Any relationship that's worthwhile is just communication. It's over communicating. I feel like as the entrepreneur who now is an investor, it's up to me to share expectations. And my expectations is keep me posted, be real, good news, bad news. What can I help with? Which is like, which are issues that are important. I don't want to run the business, but if you get an offer from a company to buy you, who else are we going to talk to? And I can help set up those conversations, right? If you're going to raise money, I can start making introductions a year before to great investors. A lot of the people who we've spoken to just sharing the expectations that I want to be a Partner. I don't want to be your boss. Now, I have the benefit of having Cass on my side, and Cass is the best CEO whisperer I've ever met, because she doesn't take board seats for the most part, and there is a dynamic as an entrepreneur that your board investors, you feel that they have more weight than your investors who are not on the board. You know, it's natural as a human being to feel that way, and so sometimes there are issues that they don't come to me. And I don't want them to. I'm on, you know, super rare NFT art marketplace. I'm on the board. John Crane has a great relationship with Cass, and Cass has helped on hiring and structure and processes. I look at, you know, Dan Separley over at Leo Labs, who …

AI assessment note: “sharing the expectations that I want to be a Partner. I don't want to be your boss.”

Q Can I ask you a bit of a weird one before we move into the quick It's like, you know, you speak with this incredible serenity and calmness, and you've just seen everything, Mike, from, you know, the incredible years building. What are your insecurities today as an investor?

A So I didn't have a ton of insecurities when we were investing out of our own balance sheet. We did about 60 deals, you know, with our own money. We never raise outside capital, and so when we decided to, you know, partner with Jim Petroni's and do Velvet Sea Ventures, you start asking yourself questions like, okay, I've gotten 250,000 to a million dollars of, like, Personal allocation for all these deals. Can we get ten million? Can we get 20? Can we get fifty million? Which is, you know, the largest deal that we've done. Are we kind of like a cute addition to the cap table, or are we like a strategic investor? Because we want to work at the highest levels of venture with the best co-investors, the best entrepreneurs. I had all these other insecurities that I hadn't felt since I started really U-Wire. At Northwestern, you know, I think everyone, no matter what they've done, you know, has this kind of imposter syndrome. And so, although I'm friends with all these VCs and I've made all this money on the investments and I was pre IPO and all these companies, including like Facebook and Tumblr and like, can I do it for a living? And so as we come out of like our first fund and we've been able to, you know, invest in companies, you know, the most important thing to me is we've product market We are people who at least 15 entrepreneurs have said, I really want you, and many of which …

AI assessment note: “Are we kind of like a cute addition to the cap table, or are we like a strategic investor?”

Q Can I ask, you know, it is also, you mentioned, you know, obviously the three children. You want to bring them up also with that in mind and with the right relationship. How do you think about instilling and implementing the work ethic, the desire that you had when the financial profile for your children is maybe very different?

A It's hard. I didn't grow up in New York City, first of all. I didn't grow up around money. Our hope, and this is a work in progress, so our kids are, you know, we're talking about 19, 17, and 14, so by no means do we think we have nailed this, but we think that if we model the behaviors that we think are important, That's the only way to learn. There's nothing we can say to them. We can't say be a good person. We can't say to them, you know, any of these traits that we would love to give to them, self-awareness and compassion and empathy. You can't talk about them. You just have to show it to them. Part of that is being there for them. And, you know, I used to say every night before my kids go to bed, and I still do if they're around, you know, love you, always be here for you, and everything will be okay. Right? Like, kids want to be supported, they want to have guardrails up, and they want to learn, like, what does it mean to, you know, to have a meaningful life, to be a good person. I think the only way to do that is to model it. Unfortunately, if you model it on the other side of not doing those things, that's where you see a lot of, you know, kids spiral out of control. But it's hard for kids these days with, you know, social media, always on, external validation, a little more difficult than when I was a

AI assessment note: “if we model the behaviors that we think are important, That's the only way to learn.”

Q What do you do as an investor, as a board member to let me, the founder know that this is a safe space. You can tell me anything because I think it's our job to create that safe space where they feel they can tell you anything. What do you do? And what did you as an entrepreneur want from your investor to know that it was a safe space?

A Any relationship that's worthwhile is just communication. It's over communicating. I feel like as the entrepreneur who now is an investor, it's up to me to share expectations. And my expectations is keep me posted, be real, good news, bad news. What can I help with? Which is like, which are issues that are important. I don't want to run the business, but if you get an offer from a company to buy you, who else are we going to talk to? And I can help set up those conversations, right? If you're going to raise money, I can start making introductions a year before to great investors. A lot of the people who we've spoken to just sharing the expectations that I want to be a Partner. I don't want to be your boss. Now, I have the benefit of having Cass on my side, and Cass is the best CEO whisperer I've ever met, because she doesn't take board seats for the most part, and there is a dynamic as an entrepreneur that your board investors, you feel that they have more weight than your investors who are not on the board. You know, it's natural as a human being to feel that way, and so sometimes there are issues that they don't come to me. And I don't want them to. I'm on, you know, super rare NFT art marketplace. I'm on the board. John Crane has a great relationship with Cass, and Cass has helped on hiring and structure and processes. I look at, you know, Dan Separley over at Leo Labs, who …

AI assessment note: “sharing the expectations that I want to be a Partner. I don't want to be your boss.”

Q What do you do as an investor, as a board member to let me, the founder know that this is a safe space. You can tell me anything because I think it's our job to create that safe space where they feel they can tell you anything. What do you do? And what did you as an entrepreneur want from your investor to know that it was a safe space?

A Any relationship that's worthwhile is just communication. It's over communicating. I feel like as the entrepreneur who now is an investor, it's up to me to share expectations. And my expectations is keep me posted, be real, good news, bad news. What can I help with? Which is like, which are issues that are important. I don't want to run the business, but if you get an offer from a company to buy you, who else are we going to talk to? And I can help set up those conversations, right? If you're going to raise money, I can start making introductions a year before to great investors. A lot of the people who we've spoken to just sharing the expectations that I want to be a Partner. I don't want to be your boss. Now, I have the benefit of having Cass on my side, and Cass is the best CEO whisperer I've ever met, because she doesn't take board seats for the most part, and there is a dynamic as an entrepreneur that your board investors, you feel that they have more weight than your investors who are not on the board. You know, it's natural as a human being to feel that way, and so sometimes there are issues that they don't come to me. And I don't want them to. I'm on, you know, super rare NFT art marketplace. I'm on the board. John Crane has a great relationship with Cass, and Cass has helped on hiring and structure and processes. I look at, you know, Dan Separley over at Leo Labs, who …

AI assessment note: “sharing the expectations that I want to be a Partner. I don't want to be your boss.”

Q How do you not let personal situations infiltrate into business decisions? Because you could have a fight in the morning, and then you're in an investment committee later, and she's still pissed at you for what you did earlier. How do you create that divide?

A So there's trust, And there, and we're all in. So there is no difference between work and life. Cass is Cass. Mike is Mike. I tried to retire after leaving Salesforce. I did an awful job at it. And this is what we do. We build businesses. We invest. We feel very fortunate to do it. And so when we have a disagreement, we're not passive aggressive. We're aggressive, aggressive. We work through it and we get to a better place. And after you do something with someone for 20, we've been married 22 years almost, and we've been together for 25 years, you learn how to take care of the me, take care of the we, personally, and that business, and we've just been very fortunate. Having said that, it's not always been easy, as all of our board members and anyone who's worked with us knows, like, any co-founders have disagreements, but we think we are incredibly lucky having what we have, and, you know, we've built just amazing, not only success in business, but But with the three kids and the life that we, uh, that we've built.

AI assessment note: “there is no difference between work and life... when we have a disagreement, we're not passive aggressive.”

Q Can I ask, you know, it is also, you mentioned, you know, obviously the three children. You want to bring them up also with that in mind and with the right relationship. How do you think about instilling and implementing the work ethic, the desire that you had when the financial profile for your children is maybe very different?

A It's hard. I didn't grow up in New York City, first of all. I didn't grow up around money. Our hope, and this is a work in progress, so our kids are, you know, we're talking about 19, 17, and 14, so by no means do we think we have nailed this, but we think that if we model the behaviors that we think are important, That's the only way to learn. There's nothing we can say to them. We can't say be a good person. We can't say to them, you know, any of these traits that we would love to give to them, self-awareness and compassion and empathy. You can't talk about them. You just have to show it to them. Part of that is being there for them. And, you know, I used to say every night before my kids go to bed, and I still do if they're around, you know, love you, always be here for you, and everything will be okay. Right? Like, kids want to be supported, they want to have guardrails up, and they want to learn, like, what does it mean to, you know, to have a meaningful life, to be a good person. I think the only way to do that is to model it. Unfortunately, if you model it on the other side of not doing those things, that's where you see a lot of, you know, kids spiral out of control. But it's hard for kids these days with, you know, social media, always on, external validation, a little more difficult than when I was a

AI assessment note: “we think that if we model the behaviors that we think are important”

Q How do you not let personal situations infiltrate into business decisions? Because you could have a fight in the morning, and then you're in an investment committee later, and she's still pissed at you for what you did earlier. How do you create that divide?

A So there's trust, And there, and we're all in. So there is no difference between work and life. Cass is Cass. Mike is Mike. I tried to retire after leaving Salesforce. I did an awful job at it. And this is what we do. We build businesses. We invest. We feel very fortunate to do it. And so when we have a disagreement, we're not passive aggressive. We're aggressive, aggressive. We work through it and we get to a better place. And after you do something with someone for 20, we've been married 22 years almost, and we've been together for 25 years, you learn how to take care of the me, take care of the we, personally, and that business, and we've just been very fortunate. Having said that, it's not always been easy, as all of our board members and anyone who's worked with us knows, like, any co-founders have disagreements, but we think we are incredibly lucky having what we have, and, you know, we've built just amazing, not only success in business, but But with the three kids and the life that we, uh, that we've built.

AI assessment note: “when we have a disagreement, we're not passive aggressive. We're aggressive, aggressive. We work through it”

Q Can I ask, you know, it is also, you mentioned, you know, obviously the three children. You want to bring them up also with that in mind and with the right relationship. How do you think about instilling and implementing the work ethic, the desire that you had when the financial profile for your children is maybe very different?

A It's hard. I didn't grow up in New York City, first of all. I didn't grow up around money. Our hope, and this is a work in progress, so our kids are, you know, we're talking about 19, 17, and 14, so by no means do we think we have nailed this, but we think that if we model the behaviors that we think are important, That's the only way to learn. There's nothing we can say to them. We can't say be a good person. We can't say to them, you know, any of these traits that we would love to give to them, self-awareness and compassion and empathy. You can't talk about them. You just have to show it to them. Part of that is being there for them. And, you know, I used to say every night before my kids go to bed, and I still do if they're around, you know, love you, always be here for you, and everything will be okay. Right? Like, kids want to be supported, they want to have guardrails up, and they want to learn, like, what does it mean to, you know, to have a meaningful life, to be a good person. I think the only way to do that is to model it. Unfortunately, if you model it on the other side of not doing those things, that's where you see a lot of, you know, kids spiral out of control. But it's hard for kids these days with, you know, social media, always on, external validation, a little more difficult than when I was a

AI assessment note: “we think that if we model the behaviors that we think are important”

Q How do you not let personal situations infiltrate into business decisions? Because you could have a fight in the morning, and then you're in an investment committee later, and she's still pissed at you for what you did earlier. How do you create that divide?

A So there's trust, And there, and we're all in. So there is no difference between work and life. Cass is Cass. Mike is Mike. I tried to retire after leaving Salesforce. I did an awful job at it. And this is what we do. We build businesses. We invest. We feel very fortunate to do it. And so when we have a disagreement, we're not passive aggressive. We're aggressive, aggressive. We work through it and we get to a better place. And after you do something with someone for 20, we've been married 22 years almost, and we've been together for 25 years, you learn how to take care of the me, take care of the we, personally, and that business, and we've just been very fortunate. Having said that, it's not always been easy, as all of our board members and anyone who's worked with us knows, like, any co-founders have disagreements, but we think we are incredibly lucky having what we have, and, you know, we've built just amazing, not only success in business, but But with the three kids and the life that we, uh, that we've built.

AI assessment note: “when we have a disagreement, we're not passive aggressive. We're aggressive, aggressive.”

Q deconstruct that, I'm too interested. This is a shit question, so you can forgive me for it. But like on the winner's win element, I'm totally with you. For me, a leading signal of a winner is like someone who's done great at a poor platform before is a good example. Like, what are the indications to you of winners? Like, how do you sense the eye of the tiger?

A Well, first of all, serial entrepreneurs, you know, produce great results. And the reason is you learn so much in the success or the failure. And so sometimes when you lose, you've done all that you can, but market turns against you for whatever reason, it didn't work out. That's the easiest way. And I just feel it myself. The first company was really hard at Northwestern. Second one was easy earth. Third one was easier. They're all hard, but you stop making some of the big mistakes and it's easier to raise money. The only way a company goes out of business is they raise money. Show me a failed product and twenty million in the bank. They still have a shot. Show me a successful product that can't raise money and, uh, you know, it'll go out of business. And so I think it gets back to one of something it's hard for me to do, but I have to continue to do it. Your gut reaction is usually right about people. And so that's The first gut reaction that you have is so critical. The problem is the next two weeks, you try to talk yourself out of that gut reaction. So you say, oh, like this isn't feeling great, this pitch or this person or whatever it is. And then you start justifying why they're great and why you're wrong, right? And so I think kind of winners have a few characteristics. One of them is they can build networks and teams and get people on board with their missions. So, you …

AI assessment note: “winners have a few characteristics. One of them is they can build networks”

Q deconstruct that, I'm too interested. This is a shit question, so you can forgive me for it. But like on the winner's win element, I'm totally with you. For me, a leading signal of a winner is like someone who's done great at a poor platform before is a good example. Like, what are the indications to you of winners? Like, how do you sense the eye of the tiger?

A Well, first of all, serial entrepreneurs, you know, produce great results. And the reason is you learn so much in the success or the failure. And so sometimes when you lose, you've done all that you can, but market turns against you for whatever reason, it didn't work out. That's the easiest way. And I just feel it myself. The first company was really hard at Northwestern. Second one was easy earth. Third one was easier. They're all hard, but you stop making some of the big mistakes and it's easier to raise money. The only way a company goes out of business is they raise money. Show me a failed product and twenty million in the bank. They still have a shot. Show me a successful product that can't raise money and, uh, you know, it'll go out of business. And so I think it gets back to one of something it's hard for me to do, but I have to continue to do it. Your gut reaction is usually right about people. And so that's The first gut reaction that you have is so critical. The problem is the next two weeks, you try to talk yourself out of that gut reaction. So you say, oh, like this isn't feeling great, this pitch or this person or whatever it is. And then you start justifying why they're great and why you're wrong, right? And so I think kind of winners have a few characteristics. One of them is they can build networks and teams and get people on board with their missions. So, you …

AI assessment note: “winners have a few characteristics. One of them is they can build networks and teams”