The Exchanges

Q But, so how did that then transition to the founding of BetterCloud?

A So I was at Vocalocity for about six years, and from Vocalocity, I went to a company that was called CloudSherpas, and CloudSherpas was very different from Vocalocity in that it was a, it's a cloud consulting company. They were helping people. When I got there, it was a very small company, and, and it was, it was helping people move off of Microsoft Exchange, Lotus Nodes, GroupWise, and And moving those people to Google Apps. They, we were migrating their email. We were setting up their Google Drive. We were training their users on how to use this new, this new platform. And they just happened to hit the timing exactly perfectly, where they were one of the first partners that signed up to be a Google Apps partner. And they were helping these companies move. And, and when I got there, my, my responsibility was to create an SMB practice, was to do, to try to figure out how to productize some of the custom applications we had been building. And what, what happened at CloudSherpa is it opened me up to this shift that was about to start. We were really at the forefront of that. We were seeing companies, big, big enterprise companies, rip and replace these legacy systems to go to Google Apps, which I don't think anyone at the time knew was really, was, was occurring. And when we were, when we were moving these customers over, I mean, they were, They were taking all sorts of risks, bu…

AI assessment note: “what happened at CloudSherpa is it opened me up to this shift”

Q 130 people in the team. And, and I want to discuss, I know people and incentivization is something that you focus on a lot. And I've heard you say before that you like to invest in everything that's not perks. So, so why is this? And why don't you believe in the kind of traditional view that perks are the most effective? And what do you think is more effective?

A Yeah, I'm pretty passionate about this subject. In general, I, I feel like incentivizing or recruiting or retaining people through perks is, is pretty lazy. I think it's superficial. It's, it's, it's unhealthy. You know, when I talk about perks, just to be clear, I mean things like free breakfast, lunch, and dinner every single day, free dry cleaning, shuttle service, yoga. I think it's bad, actually, on both sides. I think the company is going to start attracting people who are motivated by perks and may not be passionate about the vision of the organization itself, or you're just going to have to keep outdoing yourself in order to keep those people interested, and you're going to have to keep upping the game in terms of which perks you offer and And every time they, they ask for a perk, you kind of are on the hook to deliver it because that's what you, that's what you brought them in from. And I think it leaves you with an unfulfilled team, which is not really what you want. At some point it backfires. And for a person joining a company that is so focused on perks and puts that front and center, I think people would wonder, you know, not maybe people right out of school, but I think people who've been in other organizations, they start thinking if they're going to be investing this much in, in these perks, do they have enough or are they going to be investing enough? Equally …

AI assessment note: “I feel like incentivizing or recruiting or retaining people through perks is, is pretty lazy.”

Q Two, two really interesting questions to take from that. One is, firstly, what does it mean to be deliberate about What does that look like, and how have you looked to kind of infuse that into your work now with BetterCloud at a 130?

A The first way we've done that, what we've done is, one, we hired someone who's responsible to run HR. When I say that, we've had, I've had HR people in previous companies, but they've been mostly administrative, where this person we brought on was really responsible for people and, and for culture, and we needed to find someone who's really passionate about that, And ready to, to give the, you know, really invest there. And, and, and they report to me, which is also important, is that this was not something that's reporting into operations, CFO. It reports it to me, the CEO, because that's how important it is. So that's number one. Number two, we took all the things that we preach, our employee value proposition, what we expect from our team. We took all of these things and we, we wrote them down and we We wrote them down, we distributed them, and we repeat them at every meeting, company meeting that we do. We do a company meeting once a month for an hour and a half, and at the end of every meeting, we repeat these things. And, you know, the employee value prop talks about how we give people ownership over their work, talk about how we're going to be transparent, how we're going to help people grow. This is going to be a personal growth experience, a career growth experience. So we write that down, and we stick to it, and we put it out there so people hold us to it. And we tell…

AI assessment note: “The first way we've done that, what we've done is, one, we hired someone”

Q That's a very good summarization. In terms of kind of assessing your own fundraising style, what do you think you did well, and what do you think you would like to improve on for maybe a next round with BetterCloud or for a future startup?

A So the thing we did well, not on purpose, but it has come out of the, out of these rounds, is we've ended up with a very good, very well-rounded investor syndicate. We have people on the West Coast, on the East Coast. We have people who are really big in the New York Tech scene. We have people really big in enterprise IT. We have people who are, who are operators, people who are full-time investors. We have people, you know, and so we, we got this really, really good mix and really good syndicate that I, I feel is undervalued in terms of, as I talk to other founders, some people have challenges where you have all the same type or whatever that type may be, and you only get one point of view. You only get one set of connections. You only get one. So having this really interesting, well-rounded syndicate, again, not really on purpose, so I don't really give myself a lot of success for, you know, I wasn't going out and looking for that, but we, I think that was very successful, and I would do that next time more purposely than I did this time, because I think it's played out really well. And then in terms of what I could have done better, I think what I could have done better, I did not do a good job in any round. Really articulating the really, really big vision for BetterCloud. I kind of take this under-promise, over-deliver approach, and I'm just conservative in, in my approach…

AI assessment note: “in terms of what I could have done better, I did not do a good job”

Q cause it's too interesting for me to actually let you continue on BetterCloud. So I want to first discuss then the lessons that you learned on what to do and what not to do. As a first time CEO, it's an incredibly daunting proposition to have a company completely under your command. So what were the lessons that you learned to do first and then what not to do second?

A Well, to do, I, I think that part of the benefit of being so young and, and really not having experience is that there really wasn't any fear, um, and there wasn't any preconceived notions about what was possible, what was impossible, and, and so the first thing I, and I still follow this today, is just really to trust, trust your gut, and, and that really, if you put your mind to it, anything is, is possible. You need to figure out the right solution to get there, but to I think that was the thing that I learned that I was lucky enough to learn early on. That was one. Two, I learned that I was actually capable of doing and building this business, and that if I was able to do that, then there must be other people at my age or, or my level of experience who, who could really punch above their weight, and that I needed to give that opportunity to people like that, because they could really make a big impact, and, and I followed that Throughout my, my career since then, those are some of the, the, the things I learned. I mean, I learned everything about how to, how to build inside sales organization, how to do customer support, how not to do customer support, how to do, how to build product, how to hire fire. I mean, we, we, I learned so much and, and the mistakes, again, really way outnumbered the, the, the things that I would do again. And I've been working my whole career to, t…

AI assessment note: “Well, to do, I, I think that part of the benefit of being so young”

Q Absolutely. In terms of kind of the culture that that creates around perk incentivization, uh, you've been part of many companies. So with regards to that culture, what have you learned about the limits of culture? Is there a limit to culture? Do you think?

A Yeah. So, so I think that there is some limit, you know, I, I think when a company, when a company is founded, uh, The culture just is. It just, it's created organically. It's, it's almost unknowingly, and you have a couple people in the room, a couple dozen people across a couple rooms. It, it, it just, it just happens, and in many cases, it takes on the personality of the, of the founder or CEO, and, and no one's really thinking about it, and over time, that may grow, that continues to grow organically, but when you get to 80, 90, a hundred people, that's at least where I've seen it, if you're not deliberate about it, It breaks down. It breaks down because there's just, especially if you think about how many people you've been hiring and how fast, usually at that point in the company history, in the company journey, you're almost hiring too fast to really indoctrinate people and get them brought in and have it, have it through osmosis reach that person. I mean, you have to really start trying. And so for me, I've, I've seen that culture, if it's not deliberate, if you're not preparing for it, then it starts to break down when you reach that 80, 9000 people mark. So that, that's kind of where I've, where I've seen in the first two companies I was a part of, and I was part of the executive teams, and I feel like that happened at those two companies. We, we never really invested…

AI assessment note: “I think that there is some limit... when you get to 80, 90, a hundred people”

Q Two, two really interesting questions to take from that. One is, firstly, what does it mean to be deliberate about What does that look like, and how have you looked to kind of infuse that into your work now with BetterCloud at a 130?

A The first way we've done that, what we've done is, one, we hired someone who's responsible to run HR. When I say that, we've had, I've had HR people in previous companies, but they've been mostly administrative, where this person we brought on was really responsible for people and, and for culture, and we needed to find someone who's really passionate about that, And ready to, to give the, you know, really invest there. And, and, and they report to me, which is also important, is that this was not something that's reporting into operations, CFO. It reports it to me, the CEO, because that's how important it is. So that's number one. Number two, we took all the things that we preach, our employee value proposition, what we expect from our team. We took all of these things and we, we wrote them down and we We wrote them down, we distributed them, and we repeat them at every meeting, company meeting that we do. We do a company meeting once a month for an hour and a half, and at the end of every meeting, we repeat these things. And, you know, the employee value prop talks about how we give people ownership over their work, talk about how we're going to be transparent, how we're going to help people grow. This is going to be a personal growth experience, a career growth experience. So we write that down, and we stick to it, and we put it out there so people hold us to it. And we tell…

AI assessment note: “The first way we've done that, what we've done is, one, we hired someone”

Q That's a very good summarization. In terms of kind of assessing your own fundraising style, what do you think you did well, and what do you think you would like to improve on for maybe a next round with BetterCloud or for a future startup?

A So the thing we did well, not on purpose, but it has come out of the, out of these rounds, is we've ended up with a very good, very well-rounded investor syndicate. We have people on the West Coast, on the East Coast. We have people who are really big in the New York Tech scene. We have people really big in enterprise IT. We have people who are, who are operators, people who are full-time investors. We have people, you know, and so we, we got this really, really good mix and really good syndicate that I, I feel is undervalued in terms of, as I talk to other founders, some people have challenges where you have all the same type or whatever that type may be, and you only get one point of view. You only get one set of connections. You only get one. So having this really interesting, well-rounded syndicate, again, not really on purpose, so I don't really give myself a lot of success for, you know, I wasn't going out and looking for that, but we, I think that was very successful, and I would do that next time more purposely than I did this time, because I think it's played out really well. And then in terms of what I could have done better, I think what I could have done better, I did not do a good job in any round. Really articulating the really, really big vision for BetterCloud. I kind of take this under-promise, over-deliver approach, and I'm just conservative in, in my approach…

AI assessment note: “So the thing we did well... And then in terms of what I could have done better”

Q Absolutely. In terms of kind of the culture that that creates around perk incentivization, uh, you've been part of many companies. So with regards to that culture, what have you learned about the limits of culture? Is there a limit to culture? Do you think?

A Yeah. So, so I think that there is some limit, you know, I, I think when a company, when a company is founded, uh, The culture just is. It just, it's created organically. It's, it's almost unknowingly, and you have a couple people in the room, a couple dozen people across a couple rooms. It, it, it just, it just happens, and in many cases, it takes on the personality of the, of the founder or CEO, and, and no one's really thinking about it, and over time, that may grow, that continues to grow organically, but when you get to 80, 90, a hundred people, that's at least where I've seen it, if you're not deliberate about it, It breaks down. It breaks down because there's just, especially if you think about how many people you've been hiring and how fast, usually at that point in the company history, in the company journey, you're almost hiring too fast to really indoctrinate people and get them brought in and have it, have it through osmosis reach that person. I mean, you have to really start trying. And so for me, I've, I've seen that culture, if it's not deliberate, if you're not preparing for it, then it starts to break down when you reach that 80, 9000 people mark. So that, that's kind of where I've, where I've seen in the first two companies I was a part of, and I was part of the executive teams, and I feel like that happened at those two companies. We, we never really invested…

AI assessment note: “I think that there is some limit... when you get to 80, 90, a hundred people”

Q But, so how did that then transition to the founding of BetterCloud?

A So I was at Vocalocity for about six years, and from Vocalocity, I went to a company that was called CloudSherpas, and CloudSherpas was very different from Vocalocity in that it was a, it's a cloud consulting company. They were helping people. When I got there, it was a very small company, and, and it was, it was helping people move off of Microsoft Exchange, Lotus Nodes, GroupWise, and And moving those people to Google Apps. They, we were migrating their email. We were setting up their Google Drive. We were training their users on how to use this new, this new platform. And they just happened to hit the timing exactly perfectly, where they were one of the first partners that signed up to be a Google Apps partner. And they were helping these companies move. And, and when I got there, my, my responsibility was to create an SMB practice, was to do, to try to figure out how to productize some of the custom applications we had been building. And what, what happened at CloudSherpa is it opened me up to this shift that was about to start. We were really at the forefront of that. We were seeing companies, big, big enterprise companies, rip and replace these legacy systems to go to Google Apps, which I don't think anyone at the time knew was really, was, was occurring. And when we were, when we were moving these customers over, I mean, they were, They were taking all sorts of risks, bu…

AI assessment note: “what I saw at CloudSherpas was these organizations moving, and when they got over to Google”

Q 130 people in the team. And, and I want to discuss, I know people and incentivization is something that you focus on a lot. And I've heard you say before that you like to invest in everything that's not perks. So, so why is this? And why don't you believe in the kind of traditional view that perks are the most effective? And what do you think is more effective?

A Yeah, I'm pretty passionate about this subject. In general, I, I feel like incentivizing or recruiting or retaining people through perks is, is pretty lazy. I think it's superficial. It's, it's, it's unhealthy. You know, when I talk about perks, just to be clear, I mean things like free breakfast, lunch, and dinner every single day, free dry cleaning, shuttle service, yoga. I think it's bad, actually, on both sides. I think the company is going to start attracting people who are motivated by perks and may not be passionate about the vision of the organization itself, or you're just going to have to keep outdoing yourself in order to keep those people interested, and you're going to have to keep upping the game in terms of which perks you offer and And every time they, they ask for a perk, you kind of are on the hook to deliver it because that's what you, that's what you brought them in from. And I think it leaves you with an unfulfilled team, which is not really what you want. At some point it backfires. And for a person joining a company that is so focused on perks and puts that front and center, I think people would wonder, you know, not maybe people right out of school, but I think people who've been in other organizations, they start thinking if they're going to be investing this much in, in these perks, do they have enough or are they going to be investing enough? Equally …

AI assessment note: “incentivizing or recruiting or retaining people through perks is, is pretty lazy.”

Q cause it's too interesting for me to actually let you continue on BetterCloud. So I want to first discuss then the lessons that you learned on what to do and what not to do. As a first time CEO, it's an incredibly daunting proposition to have a company completely under your command. So what were the lessons that you learned to do first and then what not to do second?

A Well, to do, I, I think that part of the benefit of being so young and, and really not having experience is that there really wasn't any fear, um, and there wasn't any preconceived notions about what was possible, what was impossible, and, and so the first thing I, and I still follow this today, is just really to trust, trust your gut, and, and that really, if you put your mind to it, anything is, is possible. You need to figure out the right solution to get there, but to I think that was the thing that I learned that I was lucky enough to learn early on. That was one. Two, I learned that I was actually capable of doing and building this business, and that if I was able to do that, then there must be other people at my age or, or my level of experience who, who could really punch above their weight, and that I needed to give that opportunity to people like that, because they could really make a big impact, and, and I followed that Throughout my, my career since then, those are some of the, the, the things I learned. I mean, I learned everything about how to, how to build inside sales organization, how to do customer support, how not to do customer support, how to do, how to build product, how to hire fire. I mean, we, we, I learned so much and, and the mistakes, again, really way outnumbered the, the, the things that I would do again. And I've been working my whole career to, t…

AI assessment note: “the first thing I, and I still follow this today, is just really to trust”