The Exchanges

Q I really want to kind of talk about that sounding board element there, because I know that you have a CEO coach in the mutual friend and CEO whisperer that is Jerry Kelowna. So with that in mind, I have to ask, what was the, and please do tell me if it's too personal, what was the catalyst for your desire to have a CEO coach?

A Yeah, it's actually pretty interesting. There was a thread going around about CEO coaching that Brad had started on the Foundry CEO email distro. And I'd read a little bit about Jerry, and then I saw one thing he did in Boulder at Naropa University, and it was this actual event where I got in a fight with my wife, and it was about snow shoveling. It was like, six-thirty in the morning, and in Boulder, Colorado, we get snow pretty frequently, and I hadn't shoveled my snow, and people get pretty upset because we live on a high-traffic pedestrian street, and people slip and fall, and she got pretty upset with me, and my neighbor... Who was also a CEO, was out there shoveling my snow and my walk, and I tried to use the excuse with her, like, hey, look, I'm a busy CEO. I'm this busy guy. I don't have time to shovel the snow. Let me just find somebody to do it for me, and she sort of just said, you know, look, our neighbor's a CEO, too, but a much bigger, more successful company, and he's shoveling his walk and your walk and has two kids, so what's your excuse? And I just kind of felt like a failure as a husband, as a CEO, as a person, and I just went to Brad, and I said, I need to talk to somebody. I just, I feel like I'm sucking at life, and then I got connected with Jerry.

AI assessment note: “I just went to Brad, and I said, I need to talk to somebody.”

Q Now, should all CEOs have them, do you think, in that case, or do you think it should only be a time when you have self-doubt, you value, you kind of question your own self-worth, or do you think actually it would be relevant for every CEO?

A I would encourage every CEO to try it out. I think it's really important to have mentorship and coaching and an environment where you You can actually talk about what's going on. So I use the framework that Brad suggests, which is if you're not spending 10% of your salary every year in your company on your own personal growth and development, like you're literally suboptimizing the company. And the argument I make is like, look, if it's 10 or 20,000 dollars a year or whatever it is, do you think that that's a good investment that could make your company one percent better or one percent more valuable? Probably. Look at what that, what the impact could be on your business, and your investors should be supportive of this type of thing. So, I actually absolutely recommend it.

AI assessment note: “I would encourage every CEO to try it out.”

Q I really want to kind of talk about that sounding board element there, because I know that you have a CEO coach in the mutual friend and CEO whisperer that is Jerry Kelowna. So with that in mind, I have to ask, what was the, and please do tell me if it's too personal, what was the catalyst for your desire to have a CEO coach?

A Yeah, it's actually pretty interesting. There was a thread going around about CEO coaching that Brad had started on the Foundry CEO email distro. And I'd read a little bit about Jerry, and then I saw one thing he did in Boulder at Naropa University, and it was this actual event where I got in a fight with my wife, and it was about snow shoveling. It was like, six-thirty in the morning, and in Boulder, Colorado, we get snow pretty frequently, and I hadn't shoveled my snow, and people get pretty upset because we live on a high-traffic pedestrian street, and people slip and fall, and she got pretty upset with me, and my neighbor... Who was also a CEO, was out there shoveling my snow and my walk, and I tried to use the excuse with her, like, hey, look, I'm a busy CEO. I'm this busy guy. I don't have time to shovel the snow. Let me just find somebody to do it for me, and she sort of just said, you know, look, our neighbor's a CEO, too, but a much bigger, more successful company, and he's shoveling his walk and your walk and has two kids, so what's your excuse? And I just kind of felt like a failure as a husband, as a CEO, as a person, and I just went to Brad, and I said, I need to talk to somebody. I just, I feel like I'm sucking at life, and then I got connected with Jerry.

AI assessment note: “I just went to Brad, and I said, I need to talk to somebody.”

Q What would you most like to see change, both in VC and startups?

A The thing that I would like to see most is emotional vulnerability and empathy being more at the forefront of these things. I'm obviously Blessed to have guys like Brad Feld and Jerry involved in my company, and at Full Contact, we really go deep on the emotional aspects of entrepreneurship. I don't think we talk about it enough that it's not just business, it's actually pretty personal, too, and this notion that we can try to separate those things is kind of false, so let's actually acknowledge the emotional dynamics that are going on inside these companies, and inside the investors, and their relationships with their LPs, and So on and so forth. Let's actually talk about that more.

AI assessment note: “The thing that I would like to see most is emotional vulnerability and empathy”

Q Now, should all CEOs have them, do you think, in that case, or do you think it should only be a time when you have self-doubt, you value, you kind of question your own self-worth, or do you think actually it would be relevant for every CEO?

A I would encourage every CEO to try it out. I think it's really important to have mentorship and coaching and an environment where you You can actually talk about what's going on. So I use the framework that Brad suggests, which is if you're not spending 10% of your salary every year in your company on your own personal growth and development, like you're literally suboptimizing the company. And the argument I make is like, look, if it's 10 or 20,000 dollars a year or whatever it is, do you think that that's a good investment that could make your company one percent better or one percent more valuable? Probably. Look at what that, what the impact could be on your business, and your investors should be supportive of this type of thing. So, I actually absolutely recommend it.

AI assessment note: “I would encourage every CEO to try it out.”

Q Why, okay, why, why don't you think you're a good negotiator?

A You know, I don't know. Maybe it's, It's just imposter syndrome at the core, but I actually think I'm just a great deal maker in terms of just finding a win-win scenario for both parties to me is the best rather than trying to create a scenario that is you're adverse in competition. You try to align each other's interests. I try to put myself in the other party's shoes and think, where would a win for me be? So I try to understand their strategic objectives, what they're optimizing for, what they're thinking about, and then Think creatively about how can I fulfill that request while meeting my own needs? And so I think creativity has a lot to do with it. Um, but you know, back and forth negotiation. I mean, I actually don't have the patience for it. I optimize for time often on deals. And then this is back to the portfolio allocation standpoint. I mean, some people obsess about these little things in a deal that ultimately are not going to actually matter in the long run. Like if you think about it, is it going to be a 10 X deal or a hundred X deal? Back to the seed investing thing. I mean, it's the success of negotiation hinges on if the IRR is 12% or 14%, and it's that close, like, it's probably not a good deal. It's got to be, like, no-brainer stuff that is just like, oh, if it works, it works. If it doesn't, it's a zero. Great. But let's have a portfolio of things we're doi…

AI assessment note: “back and forth negotiation. I mean, I actually don't have the patience for it.”

Q How's it changed the way you see people work? How's it changed the way you work and think, too?

A First of all, when you go on a paid-paid vacation, It takes about three days to digitally detox, where you're not reaching for your phone, or you're just like, oh my gosh, I'm missing like a limb. So I noticed that people actually wake up to the world around them after about three days, and everybody I talk to about this starts seeing things and noticing things, noticing nature, noticing their loved ones, going back and activating parts of their brain that are sort of dormant, and anxiety and stress levels dramatically reduce. And so when they come back, they realize, A, They should do that more often. B, they were unnecessarily in a stress, anxiety, feedback loop created by the digital devices of today's era, and three, they actually realized that the world didn't end without them, the company didn't end, and oh, that's actually a good thing, right? They don't need to be the hero all the time, and so we've actually noticed processes improve because people know they're going to be gone. We've noticed mental health improve. People realize that you don't actually have to work 70 hours. You can actually knock it out in 35 hours, maybe, and if Just actually focus and simplify and declutter.

AI assessment note: “processes improve because people know they're going to be gone. We've noticed mental health improve.”

Q Why, okay, why, why don't you think you're a good negotiator?

A You know, I don't know. Maybe it's, It's just imposter syndrome at the core, but I actually think I'm just a great deal maker in terms of just finding a win-win scenario for both parties to me is the best rather than trying to create a scenario that is you're adverse in competition. You try to align each other's interests. I try to put myself in the other party's shoes and think, where would a win for me be? So I try to understand their strategic objectives, what they're optimizing for, what they're thinking about, and then Think creatively about how can I fulfill that request while meeting my own needs? And so I think creativity has a lot to do with it. Um, but you know, back and forth negotiation. I mean, I actually don't have the patience for it. I optimize for time often on deals. And then this is back to the portfolio allocation standpoint. I mean, some people obsess about these little things in a deal that ultimately are not going to actually matter in the long run. Like if you think about it, is it going to be a 10 X deal or a hundred X deal? Back to the seed investing thing. I mean, it's the success of negotiation hinges on if the IRR is 12% or 14%, and it's that close, like, it's probably not a good deal. It's got to be, like, no-brainer stuff that is just like, oh, if it works, it works. If it doesn't, it's a zero. Great. But let's have a portfolio of things we're doi…

AI assessment note: “back and forth negotiation. I mean, I actually don't have the patience for it.”

Q No, absolutely. I agree. My question was more, how do you differentiate between the two, though? Are there signs that suggest a relationship is either one or the other, be it language, be it, ah, kind of actions, be it email,

A Yeah. I mean, if, if people are really, this goes back to the negotiation piece, if you can tell that they're maximizing for the monetary value and on day one, and they're not thinking longer term, that turns me off. That's fair transaction. That's a very clear sign. So, you know, and a lot of times sales reps do this where there, there's clearly a bigger opportunity, but they're optimizing for their commission this quarter and they're actually leaving a Big pile of money on the table because they're optimizing for their commission this quarter. You know, how they actually thoughtfully take the time to get to know and understand your problems versus trying to close something too quickly when it's not yet fully baked.

AI assessment note: “That's fair transaction. That's a very clear sign.”

Q Can I double click on that? What do you mean by understand capital allocation?

A Yeah, so as a CEO, as your company grows and scales, your job becomes more about capital allocation and where you're placing your bets, right? And inside your different departments or on different markets or on different products or whatever, and you're sort of zooming out and saying, okay, we're going to allocate a few million here and a few million here, and let's see how this works and what's the return. And at a micro level, when you're making a seed stage investment, that's what you're doing, right? You're essentially constructing a portfolio. And so I've learned a lot about portfolio thinking both in venture world, as well as in the company and thinking, okay, what does, what does my, Series of bets I'm making as a company. And so, you know, I find it very useful. More importantly, the most important thing I think though, is the emotional element. My role at V one VC is actually diving into the entrepreneurs about the emotional gut wrenching difficulties of entrepreneurship. And, you know, I try to serve as a coach and a sounding board for, you know, whatever terrible thing they're dealing with that particular day. And that's very helpful to get that perspective and, and have a sort of community of CEOs and founders that you're Genuinely talking about your problems with.

AI assessment note: “your job becomes more about capital allocation and where you're placing your bets”

Q Can I double click on that? What do you mean by understand capital allocation?

A Yeah, so as a CEO, as your company grows and scales, your job becomes more about capital allocation and where you're placing your bets, right? And inside your different departments or on different markets or on different products or whatever, and you're sort of zooming out and saying, okay, we're going to allocate a few million here and a few million here, and let's see how this works and what's the return. And at a micro level, when you're making a seed stage investment, that's what you're doing, right? You're essentially constructing a portfolio. And so I've learned a lot about portfolio thinking both in venture world, as well as in the company and thinking, okay, what does, what does my, Series of bets I'm making as a company. And so, you know, I find it very useful. More importantly, the most important thing I think though, is the emotional element. My role at V one VC is actually diving into the entrepreneurs about the emotional gut wrenching difficulties of entrepreneurship. And, you know, I try to serve as a coach and a sounding board for, you know, whatever terrible thing they're dealing with that particular day. And that's very helpful to get that perspective and, and have a sort of community of CEOs and founders that you're Genuinely talking about your problems with.

AI assessment note: “your job becomes more about capital allocation and where you're placing your bets”

Q do want to dive in quickly on the world of VC slightly here, because you've got a very interesting perspective. Being both a founder with Full Contact, and then also your role as an LP and an MD with V-One and Brett Jackson. So, I'm really intrigued. How does this role on the other side of the table affect how you first view and analyze startups? Let's start with that.

A Yeah, I mean, um, you know, my role at V-One VC, uh, you know, just sort of as a natural evolution. We have a five million dollar seed fund focused on helping crazy entrepreneurs that want to change the world. And I've been an angel investor for many, many years and been doing angel investing with Fred Jackson, as well as actually Benny Joseph, as well as the other managing director. And we just decided to create a fund. So to me, it's actually very helpful to be quote simultaneously on both sides of the table, because you can actually, often I'm actually evaluating a business or looking at a company or helping one of our portfolio entrepreneurs view NBC. And it gives me insight into something I might be screwing up at full contact. And so the act of, like, coaching somebody else to a problem sometimes reveals things inside your own company that are screwed up, and we all have things that are screwed up. It also helps me understand markets and understand capital allocation.

AI assessment note: “to me, it's actually very helpful to be quote simultaneously on both sides of the table”

Q do want to dive in quickly on the world of VC slightly here, because you've got a very interesting perspective. Being both a founder with Full Contact, and then also your role as an LP and an MD with V-One and Brett Jackson. So, I'm really intrigued. How does this role on the other side of the table affect how you first view and analyze startups? Let's start with that.

A Yeah, I mean, um, you know, my role at V-One VC, uh, you know, just sort of as a natural evolution. We have a five million dollar seed fund focused on helping crazy entrepreneurs that want to change the world. And I've been an angel investor for many, many years and been doing angel investing with Fred Jackson, as well as actually Benny Joseph, as well as the other managing director. And we just decided to create a fund. So to me, it's actually very helpful to be quote simultaneously on both sides of the table, because you can actually, often I'm actually evaluating a business or looking at a company or helping one of our portfolio entrepreneurs view NBC. And it gives me insight into something I might be screwing up at full contact. And so the act of, like, coaching somebody else to a problem sometimes reveals things inside your own company that are screwed up, and we all have things that are screwed up. It also helps me understand markets and understand capital allocation.

AI assessment note: “gives me insight into something I might be screwing up at full contact.”