The Exchanges

Q And then post that conversation with your wife, Jeff, how did that translate into the move to CEO at Boosted?

A I get that question a lot. I have to admit, after doing almost 25 years of internet and digital media and enterprise software, one has to ask what kind of midlife crisis I was having to take a left hook into the world's leading electric skateboard provider. For me, it was actually a return home. I started out as a PhD in robotics and autonomous systems 25 years ago. And it really just left the space. I famously told my buddies, until batteries and other technologies get better, I'll see in about 20 to 25 years. And it's been almost 25 years. So I was introduced to Coastal Ventures, Samir Calder. He really wanted to do something with me on one of their portfolio companies. And then when I met the folks at Boosted, it was like coming home. So the founders at Boosted came from the exact same PhD program at Stanford that I did. Same classes, and to this day, some of the same professors. So, when we met, it was almost like meeting our long-lost brothers, where I was the brother that had gone off to 25 years of business experience, and they were the brothers that had stayed more techie and entrepreneurial. So, uh, for me, it's actually not been a left hook. It's actually been a return home, and it's the most fun I've ever had.

AI assessment note: “I was introduced to Coastal Ventures... when I met the folks at Boosted”

Q Kind of investors stepping up and switching sides of the table when you're thinking about the raise and the investors that you're presenting to you. I'm always fascinated by kind of investor selection. How do you approach investor selection, Jeff?

A Yeah, as you gather from my last name, I'm Russian, and so there's an old Russian saying, it's better to pick potatoes with people you like. And so for me, actually, I have the simplest litmus test ever. I have three daughters, and so when I meet investors, one of the first questions I ask is, If my wife and I needed to go run off for the weekend and handle some terrible emergency and leave my three daughters with this person just for the weekend without a word said, would I even think twice about it? And if the answer is I'd have to think twice, that's probably a good litmus test because if I'm not sure I can leave them to watch my girls for a weekend, why would I want to be committed to them for the next seven, eight years in a journey together where we're counting on each other to be successful for my kids' college education? So to me, it really is, are they fundamentally good people, character, Integrity. Trust. Every company hits moments of success, but it also hits air pockets. And you need to know there's somebody that's going to be there with you through thick and thin. So that really is the gut check. After that, there's a lot of investors that can provide capital. And so what's the investor value beyond the capital? Some of the things that I find really helpful is can they help with talent? Can they help source talent? Can they help close talent to a company, especial…

AI assessment note: “when I meet investors, one of the first questions I ask is”

Q And then final question here, Jeff, what would you, in terms of the next five years, For you and for Boosted, what does that future look like? Paint that picture for me.

A Yeah, I think five years from now, my hope is that we are in the midst of a second mobile revolution, where the first mobile revolution was more around anywhere, anytime, competing with the phone, and the second is really around anywhere, anytime, competing with light vehicles. We've pretty much reached a point where an automotive-based society is breaking down. The idea of people going around in 3500 pound cars that are 15 feet long being stuck in traffic It's now become probably one of the biggest inefficiencies in our lives, and so I do think that the need for less small transportation options and light electric vehicles is a fundamental revolution, and the pun is on mobile revolution, and so I'd love it if five years from now, a significant portion of the population was going around on all manner of light vehicles, you know, skateboards, scooters, bikes, wheelchairs, walkers, whatever they want to come up with, And then for Boosted, we really see ourselves as, you know, like the Apple or the Peloton of that space, and we would really love to be the Hallmark brand and benchmark for that range of class of vehicles, the way we are in skateboard today.

AI assessment note: “Boosted, we really see ourselves as, you know, like the Apple or the Peloton”

Q university. They say, Harry, I have three options. I can join the tiny startup where I have a big impact I can join your stripe of the world, which is obviously the hyper growth, multi-billion dollar rocket ship that it is, or I can join your Facebook or Google of the world and gain that corporate knowledge. What would you advise that person if they were maybe your own child?

A Yeah, and it is advice that I look forward to giving to my children one day when they're ready. The first thing I'm going to say, which is not going to sound fully satisfying, is there's no right answer without looking at who you are and where you are. For a lot of people in their twenties, If you have that entrepreneurial drive where you really just need to go do it, that's going to end up being the path that may make the most sense for you. I do actually think, and this is a bit countercultural sometimes to Silicon Valley, I think for a lot of people to go spend the twenties and the thirties in larger environments and being able to have the chance to get that education across different functions of a company, different business models, different types of product. How to be an executive in a company and get things done. Those are incredible skills to learn, and I do think people that have come through that environment and then come back to entrepreneurship do bring a tremendous amount of value to growth companies, and the entrepreneurial gene may also have been there all along. The funny thing is you look back at age 50, and you realize that people that took both paths end up kind of happy and about the same level of success 30 years later either way, and so you start to realize there's less of a Right path than you felt like when you were 21 or 22. So it really comes down to,…

AI assessment note: “there's no right answer without looking at who you are and where you are.”

Q I mean, so, so many things to unpack there, and so unfair of me to go off schedule, but I do have to ask, how do you think about determining between air pocket and potential kind of flight failure mode?

A I mean, as I said before, transparency is, it's, it's helpful just to push the metaphor a little further. It is helpful if your plane is well instrumented, and you know whether or not you can understand what's going on, but it also, there's no replacing experience. If you've been in a, that plane a hundred times, you know instinctively when to investigate versus when to not worry. If it's your first time in the plane, then it can be, you know, more alarming, and it would be helpful if you have a co-pilot or somebody next to you that, that has been in that plane a hundred times, and just to go with their guidance. So, combination of experience and just read your instrument panel. Is something, are little arms going off, or is it just a little bouncing around?

AI assessment note: “So, combination of experience and just read your instrument panel.”

Q university. They say, Harry, I have three options. I can join the tiny startup where I have a big impact I can join your stripe of the world, which is obviously the hyper growth, multi-billion dollar rocket ship that it is, or I can join your Facebook or Google of the world and gain that corporate knowledge. What would you advise that person if they were maybe your own child?

A Yeah, and it is advice that I look forward to giving to my children one day when they're ready. The first thing I'm going to say, which is not going to sound fully satisfying, is there's no right answer without looking at who you are and where you are. For a lot of people in their twenties, If you have that entrepreneurial drive where you really just need to go do it, that's going to end up being the path that may make the most sense for you. I do actually think, and this is a bit countercultural sometimes to Silicon Valley, I think for a lot of people to go spend the twenties and the thirties in larger environments and being able to have the chance to get that education across different functions of a company, different business models, different types of product. How to be an executive in a company and get things done. Those are incredible skills to learn, and I do think people that have come through that environment and then come back to entrepreneurship do bring a tremendous amount of value to growth companies, and the entrepreneurial gene may also have been there all along. The funny thing is you look back at age 50, and you realize that people that took both paths end up kind of happy and about the same level of success 30 years later either way, and so you start to realize there's less of a Right path than you felt like when you were 21 or 22. So it really comes down to,…

AI assessment note: “there's no right answer without looking at who you are and where you are.”

Q kind of turning on the afterburners, you know, you're a seasoned operator, and now kind of CEO of Boosted. In terms of kind of the environments we're in, I think we'd agree that they're quite Profit, so to speak, in terms of funding, how do you think about and maybe approach capital efficiency today, thinking about kind of the sixty million raise and the next milestones for the next round?

A Yeah, I'll come back to the frothy part in 1:02. I think in any market, you've got this reality as you grow a company through seed series A, B, C, D. As a growth company, particularly around on B, B, C, you need to keep a healthy balance between getting excited about the froth and the market opportunity with running an increasingly capital efficient business. When you're at seed in series A, where you're pre-revenue or first establishing a product in the market, it's almost a hundred percent about establishing the vision and is the product in the market category going to be successful. And then on the flip side, when you're already up at CDE, you've already got the recipe, you're at larger scale, and it's really just about pouring capital into something to scale it. In the middle around series B, you're at this really interesting inflection point where it catches a lot of Management teams by surprise, where you're still maybe growing at hundreds of percent, but you need all of your financial metrics and operational metrics to start performing, because you're kind of going from all vision in A to it's already working in C, and so B's that point where the numbers really start to matter, and how are your revenues scaling, and are your gross margins improving, and is your OPEX getting more efficient, and are you reducing your customer acquisition costs, and 20 other really critical…

AI assessment note: “you need to keep a healthy balance between getting excited... with running an increasingly capital efficient business”

Q What do you find the most challenging in terms of that between a stage being the Series B stage, where you have everything that you want needs to succeed potentially on the foundational level, but also not in terms of necessarily all the data points proven out? How do you think about the biggest challenges at that stage?

A Yeah, I think the biggest challenge at that point is you've got the biggest stretch between the vision and the metrics Being in your hands and proven. And so you need to do a very good job of being able to demonstrate to yourself and to investors, maybe leading indicators or things that indicate that the metrics are pointing the right way. Cause it's the biggest bet for the investor at that point where you're asking, you're starting to ask for real money, but you're still finalizing the recipe and you're not fully efficient. So you have to do a few things. You have to be very transparent when you're at vision stage, you can paint a dream. When you're in series B, you can still point to the vision, but there'll be stuff that's working and the stuff that's not. You have to be very transparent with your investors and help them understand and diagnose why what is working is working and why what is not is something that will work as opposed to what's a fundamental thing about your business. And it's something that's addressable and operational versus fundamental. And so you need to do that for them, but also for yourself. If you can do that really well, then you can gain the confidence to keep gathering funding and keep going. But that is the toughest thing for most companies going through that stage where you're not yet profitable. You're growing like crazy. It's mostly working. Fe…

AI assessment note: “the biggest challenge at that point is you've got the biggest stretch between the vision”

Q I love that thinking of the return home, but you mentioned the names of Adobe, Symantec, SAP. I do have to ask then, Jeff, what were the takeaways from For you from seeing the first-hand hypergrowth of these organizations?

A You learn a lot. I think entrepreneurship, but also leadership, there are a lot of learned and apprenticed elements to that and that experience. And so I think once a company hits some kind of initial product market fit, experience and the general management skills really start to kick in and become critical to scaling. So things like business problem solving, strategy, building an organization, developing people, Being able to think about multiple products, multiple geographies, multiple business models, it really does pay to have been in growth and scale many times before, and having seen the movie multiple times, different angles, different industries, different types of companies, different cultures, and to have the ability to know what things should look like at scale and to have an urgency to get there. And so coming into a company like this one, boosted, we've grown from two countries to 34, expanded from one channel to multiple, And expand it from one business model to multiple. It really helps to have just seen the movie multiple times before. And so the larger companies are an amazing development ground because within each company, you've got dozens of products, dozens of geographies, different business models, and you just get exposed to a lot in those environments.

AI assessment note: “general management skills really start to kick in and become critical to scaling”

Q more graduates that now I don't need to answer. I do want to start though today, Jeff, as one could guess from the title of the show on the theme of funding, but more importantly, maybe the construction of business alongside it. So I'd love to start on this. Being at the epicenter in SF, how do you assess The current sentiment of funding, specifically with regards to business construction?

A You know, I think it's changed a lot. You know, I think about what the fundraising community was like 25 plus years ago, 30 years ago when I was coming out of college. By contrast, back then, VCs tended to have very deep expertise in certain industries or technologies and could go very deep on, on diligence, whereas today's investors tend to be more generalists. So you're less likely to find investors today who develop a proprietary view versus have more of a consensus mentality. The math has also changed. Whereas maybe 25, 30 years ago, a VC would tell you, you know, I'm looking to make 10 investments and have one be a hit to a mindset of every investment I need to invest in needs to be able to be the one to return my entire fund. And so it tends to be more home run ball versus looking to hit a lot of singles, doubles, and triples, you know, to use a baseball analogy. It can cause investors to look past, you know, solid to great businesses with a high likelihood of return to more venturous businesses with a lower likelihood of a return, but a return that may be at a fantasy level of return. And so more investments tend to be flyers seeking network effects with more willing suspension of disbelief than I think maybe we saw a few decades ago. I think a second thing that's changed or a third thing that's changed is I think we're seeing less investment in consumer hardware and fun…

AI assessment note: “I think it's changed a lot... today's investors tend to be more generalists”

Q Kind of investors stepping up and switching sides of the table when you're thinking about the raise and the investors that you're presenting to you. I'm always fascinated by kind of investor selection. How do you approach investor selection, Jeff?

A Yeah, as you gather from my last name, I'm Russian, and so there's an old Russian saying, it's better to pick potatoes with people you like. And so for me, actually, I have the simplest litmus test ever. I have three daughters, and so when I meet investors, one of the first questions I ask is, If my wife and I needed to go run off for the weekend and handle some terrible emergency and leave my three daughters with this person just for the weekend without a word said, would I even think twice about it? And if the answer is I'd have to think twice, that's probably a good litmus test because if I'm not sure I can leave them to watch my girls for a weekend, why would I want to be committed to them for the next seven, eight years in a journey together where we're counting on each other to be successful for my kids' college education? So to me, it really is, are they fundamentally good people, character, Integrity. Trust. Every company hits moments of success, but it also hits air pockets. And you need to know there's somebody that's going to be there with you through thick and thin. So that really is the gut check. After that, there's a lot of investors that can provide capital. And so what's the investor value beyond the capital? Some of the things that I find really helpful is can they help with talent? Can they help source talent? Can they help close talent to a company, especial…

AI assessment note: “to me, it really is, are they fundamentally good people, character, Integrity. Trust.”

Q I mean, so, so many things to unpack there, and so unfair of me to go off schedule, but I do have to ask, how do you think about determining between air pocket and potential kind of flight failure mode?

A I mean, as I said before, transparency is, it's, it's helpful just to push the metaphor a little further. It is helpful if your plane is well instrumented, and you know whether or not you can understand what's going on, but it also, there's no replacing experience. If you've been in a, that plane a hundred times, you know instinctively when to investigate versus when to not worry. If it's your first time in the plane, then it can be, you know, more alarming, and it would be helpful if you have a co-pilot or somebody next to you that, that has been in that plane a hundred times, and just to go with their guidance. So, combination of experience and just read your instrument panel. Is something, are little arms going off, or is it just a little bouncing around?

AI assessment note: “combination of experience and just read your instrument panel”

Q What moment in your life has served as an inflection point and maybe changed the way you think?

A I think for me, I definitely had an inflection point about halfway through my career to date. Early in my career, I was definitely the classic, I'll call it brain on a stick. You know, go get the, go to the best school, go get a PhD, join the biggest brands, and there's a right answer, and there's a meritocracy kind of mindset, and if you do great work, and you, you've got a great resume, great experience, you keep going up, and then you get to this point where you get, particularly for me, as you get into real life and large companies where, That's not really how it works. Being bright is helpful, but you start to realize there's 15 other skills that really matter. Leadership, common sense, experience, the ability to influence others, uh, relationship building, building long trusted relationships. And these things matter as much, if not more, than just the, the pure business problem of the situation you're in. And so a lot of us would just connote that as EQ, you know, as a coworker and as a leader. And so I found about halfway through my career, I started just thinking differently. My office is a living room and invite everyone in and suspend your own agenda. Always ask people what their agenda is first and work on that with them first, because if you love working together and feel people feel comfortable around you, you might only get 80% of what you wanted to get done today…

AI assessment note: “I definitely had an inflection point about halfway through my career to date.”

Q kind of turning on the afterburners, you know, you're a seasoned operator, and now kind of CEO of Boosted. In terms of kind of the environments we're in, I think we'd agree that they're quite Profit, so to speak, in terms of funding, how do you think about and maybe approach capital efficiency today, thinking about kind of the sixty million raise and the next milestones for the next round?

A Yeah, I'll come back to the frothy part in 1:02. I think in any market, you've got this reality as you grow a company through seed series A, B, C, D. As a growth company, particularly around on B, B, C, you need to keep a healthy balance between getting excited about the froth and the market opportunity with running an increasingly capital efficient business. When you're at seed in series A, where you're pre-revenue or first establishing a product in the market, it's almost a hundred percent about establishing the vision and is the product in the market category going to be successful. And then on the flip side, when you're already up at CDE, you've already got the recipe, you're at larger scale, and it's really just about pouring capital into something to scale it. In the middle around series B, you're at this really interesting inflection point where it catches a lot of Management teams by surprise, where you're still maybe growing at hundreds of percent, but you need all of your financial metrics and operational metrics to start performing, because you're kind of going from all vision in A to it's already working in C, and so B's that point where the numbers really start to matter, and how are your revenues scaling, and are your gross margins improving, and is your OPEX getting more efficient, and are you reducing your customer acquisition costs, and 20 other really critical…

AI assessment note: “B's that point where the numbers really start to matter”

Q And then post that conversation with your wife, Jeff, how did that translate into the move to CEO at Boosted?

A I get that question a lot. I have to admit, after doing almost 25 years of internet and digital media and enterprise software, one has to ask what kind of midlife crisis I was having to take a left hook into the world's leading electric skateboard provider. For me, it was actually a return home. I started out as a PhD in robotics and autonomous systems 25 years ago. And it really just left the space. I famously told my buddies, until batteries and other technologies get better, I'll see in about 20 to 25 years. And it's been almost 25 years. So I was introduced to Coastal Ventures, Samir Calder. He really wanted to do something with me on one of their portfolio companies. And then when I met the folks at Boosted, it was like coming home. So the founders at Boosted came from the exact same PhD program at Stanford that I did. Same classes, and to this day, some of the same professors. So, when we met, it was almost like meeting our long-lost brothers, where I was the brother that had gone off to 25 years of business experience, and they were the brothers that had stayed more techie and entrepreneurial. So, uh, for me, it's actually not been a left hook. It's actually been a return home, and it's the most fun I've ever had.

AI assessment note: “when I met the folks at Boosted, it was like coming home.”

Q more graduates that now I don't need to answer. I do want to start though today, Jeff, as one could guess from the title of the show on the theme of funding, but more importantly, maybe the construction of business alongside it. So I'd love to start on this. Being at the epicenter in SF, how do you assess The current sentiment of funding, specifically with regards to business construction?

A You know, I think it's changed a lot. You know, I think about what the fundraising community was like 25 plus years ago, 30 years ago when I was coming out of college. By contrast, back then, VCs tended to have very deep expertise in certain industries or technologies and could go very deep on, on diligence, whereas today's investors tend to be more generalists. So you're less likely to find investors today who develop a proprietary view versus have more of a consensus mentality. The math has also changed. Whereas maybe 25, 30 years ago, a VC would tell you, you know, I'm looking to make 10 investments and have one be a hit to a mindset of every investment I need to invest in needs to be able to be the one to return my entire fund. And so it tends to be more home run ball versus looking to hit a lot of singles, doubles, and triples, you know, to use a baseball analogy. It can cause investors to look past, you know, solid to great businesses with a high likelihood of return to more venturous businesses with a lower likelihood of a return, but a return that may be at a fantasy level of return. And so more investments tend to be flyers seeking network effects with more willing suspension of disbelief than I think maybe we saw a few decades ago. I think a second thing that's changed or a third thing that's changed is I think we're seeing less investment in consumer hardware and fun…

AI assessment note: “a greater focus on business models that really complement the VC filter, particularly around SaaS”

Q I have to say, I absolutely love that element of the litmus test, leaving your daughters with them. I do have to ask, you mentioned the element of air pockets there. Absolutely. They happen. Can I ask, how do you personally deal with air pockets? I go to the gym and run like a maniac. How do you personally deal with air pockets?

A I would say two things. So it's part of growing or scaling or hyper scaling. You're going to make bets. Um, and some are not going to work out, and you're going to learn from them. If you're very transparent when you hit air pockets, when you do a really good job of analyzing what have you learned from it, then I actually think those are things that strengthen the company and build credibility. But separately, if I were to push the metaphor of air pockets a little bit further, and this is probably back to big company versus small company. One thing that's interesting for a lot of folks when they come into the companies of this size is Air pockets really catch your attention. When you're in a big company, you're like in a jet airliner. You barely notice all but the biggest air pockets, and it's this pretty smooth ride. When you go into a startup or growth company, it's more like getting into a two-seater little airplane that's like a kite with an engine on it, and so you bounce around, and you get buffeted a lot more by the wind and the events, and so it's very natural to become alarmed or freaked out the first time you suddenly plunge 25 feet. But after a while, you get used to it, because you realize that's just the nature of being in a small plane. There's 25,000 feet of air between me and the ground, and so the wings will catch. And so it's the ability to understand what's a…

AI assessment note: “If you're very transparent when you hit air pockets, when you do a really good job”

Q What do you mean by that in terms of the business model element, and what would one like to see more in the VC class then when digging deeper into the hardware stack in an opportunity?

A I think when people say hardware is hard, almost by All businesses can be hard, and simply no matter what flavor of hard, but all businesses can be successful. And I say this because I've been in all the above. In hardware, you've got a lot of pain up front. It might take you a year to get out the product. The product has to be perfect before you get it out the door, because once you get out the door, you can't get it back, and it takes a lot of capital to, to get going. But once you launch it, if it's successful, it can be incredibly easy to hyperscale. Just because people love the product, and they just start snatching it up like hotcakes, and then you can build defensive moats around brand and channel. In software, I think the thing that people miss is, look, launching the product is easy. Heck, in enterprise software, it doesn't even need to be fully baked. It could be 40 to 60% made, and you have a great PowerPoint, and so you don't need this painful year and all this capital to launch the product, but then you've got to sell the product, and now you can be in sales cycles that are nine And 12 months long. And if you've ever tried to sell enterprise software to HR or marketing departments, now you've got a year of selling. And then once you sell it, then you have months of them getting them to adopt the product and use it. And then you have to come back 12 or 18 months lat…

AI assessment note: “In hardware, you've got a lot of pain up front. It might take you a year”

Q Well, that is very, very kind, but I'd love to get started on you. So tell me, Jeff, how did you make your way into the world of startups and really come to be CEO at Boosted?

A Yeah, so thanks for asking. Um, I'm definitely a CEO that came into startups really mid-career. I spent the first 15 to 20 years of my career in Fortune 500, SIP, Adobe, Semantic, Yahoo, and only really about eight, nine years ago, started getting into growth. I had always done very entrepreneurial things within larger companies and had that gene and was always itching to try things that were more around growth and scale. So after my fourth big company, I was finally able to look at my wife and say, okay, house is paid for, college is set aside for the kids one day, I really need to be doing something else for my growth, and she was very supportive.

AI assessment note: “I'm definitely a CEO that came into startups really mid-career.”

Q Well, that is very, very kind, but I'd love to get started on you. So tell me, Jeff, how did you make your way into the world of startups and really come to be CEO at Boosted?

A Yeah, so thanks for asking. Um, I'm definitely a CEO that came into startups really mid-career. I spent the first 15 to 20 years of my career in Fortune 500, SIP, Adobe, Semantic, Yahoo, and only really about eight, nine years ago, started getting into growth. I had always done very entrepreneurial things within larger companies and had that gene and was always itching to try things that were more around growth and scale. So after my fourth big company, I was finally able to look at my wife and say, okay, house is paid for, college is set aside for the kids one day, I really need to be doing something else for my growth, and she was very supportive.

AI assessment note: “I'm definitely a CEO that came into startups really mid-career.”

Q I love that thinking of the return home, but you mentioned the names of Adobe, Symantec, SAP. I do have to ask then, Jeff, what were the takeaways from For you from seeing the first-hand hypergrowth of these organizations?

A You learn a lot. I think entrepreneurship, but also leadership, there are a lot of learned and apprenticed elements to that and that experience. And so I think once a company hits some kind of initial product market fit, experience and the general management skills really start to kick in and become critical to scaling. So things like business problem solving, strategy, building an organization, developing people, Being able to think about multiple products, multiple geographies, multiple business models, it really does pay to have been in growth and scale many times before, and having seen the movie multiple times, different angles, different industries, different types of companies, different cultures, and to have the ability to know what things should look like at scale and to have an urgency to get there. And so coming into a company like this one, boosted, we've grown from two countries to 34, expanded from one channel to multiple, And expand it from one business model to multiple. It really helps to have just seen the movie multiple times before. And so the larger companies are an amazing development ground because within each company, you've got dozens of products, dozens of geographies, different business models, and you just get exposed to a lot in those environments.

AI assessment note: “experience and the general management skills really start to kick in and become critical to scaling”

Q I have to say, I absolutely love that element of the litmus test, leaving your daughters with them. I do have to ask, you mentioned the element of air pockets there. Absolutely. They happen. Can I ask, how do you personally deal with air pockets? I go to the gym and run like a maniac. How do you personally deal with air pockets?

A I would say two things. So it's part of growing or scaling or hyper scaling. You're going to make bets. Um, and some are not going to work out, and you're going to learn from them. If you're very transparent when you hit air pockets, when you do a really good job of analyzing what have you learned from it, then I actually think those are things that strengthen the company and build credibility. But separately, if I were to push the metaphor of air pockets a little bit further, and this is probably back to big company versus small company. One thing that's interesting for a lot of folks when they come into the companies of this size is Air pockets really catch your attention. When you're in a big company, you're like in a jet airliner. You barely notice all but the biggest air pockets, and it's this pretty smooth ride. When you go into a startup or growth company, it's more like getting into a two-seater little airplane that's like a kite with an engine on it, and so you bounce around, and you get buffeted a lot more by the wind and the events, and so it's very natural to become alarmed or freaked out the first time you suddenly plunge 25 feet. But after a while, you get used to it, because you realize that's just the nature of being in a small plane. There's 25,000 feet of air between me and the ground, and so the wings will catch. And so it's the ability to understand what's a…

AI assessment note: “If you're very transparent when you hit air pockets, when you do a really good job”

Q What do you mean by that in terms of the business model element, and what would one like to see more in the VC class then when digging deeper into the hardware stack in an opportunity?

A I think when people say hardware is hard, almost by All businesses can be hard, and simply no matter what flavor of hard, but all businesses can be successful. And I say this because I've been in all the above. In hardware, you've got a lot of pain up front. It might take you a year to get out the product. The product has to be perfect before you get it out the door, because once you get out the door, you can't get it back, and it takes a lot of capital to, to get going. But once you launch it, if it's successful, it can be incredibly easy to hyperscale. Just because people love the product, and they just start snatching it up like hotcakes, and then you can build defensive moats around brand and channel. In software, I think the thing that people miss is, look, launching the product is easy. Heck, in enterprise software, it doesn't even need to be fully baked. It could be 40 to 60% made, and you have a great PowerPoint, and so you don't need this painful year and all this capital to launch the product, but then you've got to sell the product, and now you can be in sales cycles that are nine And 12 months long. And if you've ever tried to sell enterprise software to HR or marketing departments, now you've got a year of selling. And then once you sell it, then you have months of them getting them to adopt the product and use it. And then you have to come back 12 or 18 months lat…

AI assessment note: “all business models are hard. It's simply where in the cycle is it hard”

Q Okay, totally agree with you there in terms of that. Sometimes it doesn't work. Where do you think, and I'm sure you've seen over the 25 years, Why do you think people maybe make mistakes in trying to instill this foundational change and it doesn't work? What are the root causes?

A Yeah, so I'll answer that with a small aside. When you're looking for, as a CEO or potential CEO to come into, to a growth company, 19 out of 20 times, the story is something like the following. The company is, is growing like crazy and has this revenue. It's near profitability. The investors are excited and there's plenty of money around the table. The founders are excited to bring in some additional help. There's plenty of energy, uh, to, to go the next mile with the company. And what quite often is, is the case is don't divide the revenue by two divided by four, but just because the, the investors are optimistic, um, and almost giving you next year's projection, which means that it's not near profitable. It's still potentially losing a lot of money. The relationship between the founders and the investors may be, uh, strained. And the investors are looking to bring in a professional CEO to help, and the founders may not be fully supportive. The founders and the management team by that point be somewhat fatigued, and the relationship between them and the investors may be somewhat toxic. That's more typically that case than not. And if you've seen the movie enough times, it gets easier to see. And so I think where it works well, and what you tend to look for is the things about the company that you want to be great, Are great. So in the case of boosted, for example, amazing pro…

AI assessment note: “Yeah, so I'll answer that with a small aside.”