The Exchanges

Q to ask, I'm sorry to go off schedule this early, but I'd actually love your advice. Because I often face things where there's like that personal choice, and then there's that professional choice. And whenever I choose the personal, I feel really personally guilty that I haven't chosen the professional choice. I kind of shame myself. How did you prevent yourself from doing that? And how do you advise me?

A Well, I always listened to some advice that I got early on in my career while I was at Intuit. You know, our CEO there, Brad Smith, former CEO, I should say, he always said in life, you got to weigh the things that are rubber and those that are crystal. Things that are rubber bounce back. After some period of time, you'll, you'll never think about it again. Things that are crystal hit the ground, shatter, and you can't necessarily recover them. And, you know, I think things like a significant other, things like attending your kid's graduation or dance rehearsal, being at your parents' sixties, you know, those, those are things that are crystal. Um, you're not really going to get them back. And to me, when I did that, that internal text, the move into New York thing, the going for the girl felt like something that was crystal.

AI assessment note: “weigh the things that are rubber and those that are crystal”

Q Okay, so your favorite book and why. What's my must read for today?

A It's a pretty popular book, so you might have already read it, but I'm a, I'm a huge fan of originals by Adam Brandt. I'll tell you why. I live in a world where I'm constantly surrounded by people who Have 10, 20, 30 years more experience than me. Meaning that they can point to any number of examples about how things that they've done or seen have been successful or failed for whatever reason. I just don't have that sample size at this juncture in my life. But this book celebrates those who come to the table with a different perspective, and they call them nonconformists. And that's a view that I really cherish and love and empowers me to still have a voice despite not having the same tenure. Some of the people that I engage with.

AI assessment note: “I'm a huge fan of originals by Adam Brandt. I'll tell you why.”

Q Okay, so your favorite book and why. What's my must read for today?

A It's a pretty popular book, so you might have already read it, but I'm a, I'm a huge fan of originals by Adam Brandt. I'll tell you why. I live in a world where I'm constantly surrounded by people who Have 10, 20, 30 years more experience than me. Meaning that they can point to any number of examples about how things that they've done or seen have been successful or failed for whatever reason. I just don't have that sample size at this juncture in my life. But this book celebrates those who come to the table with a different perspective, and they call them nonconformists. And that's a view that I really cherish and love and empowers me to still have a voice despite not having the same tenure. Some of the people that I engage with.

AI assessment note: “I'm a huge fan of originals by Adam Brandt. I'll tell you why.”

Q Not at all. I'm excited, but I do want to kick off today with a little bit on you. So tell me, my friend, how on earth did you make your way from the world of venture to one of the fastest growing companies in history in UI path? What was that journey and transition for you?

A My transition, unlike most people, had nothing to do with professional ambition whatsoever. I was working for a enterprise software expansion stage focused venture capital firm out in Boston called OpenView Venture Partners. And I was there for four years working with a good friend and someone who I respect so much partnered there by the name of Mackie Craven. We're focused on the cloud infrastructure and data technology and Component practice of the firm. And I was also dating my girlfriend. We were doing distance. She got a really amazing job offer in New York. And I don't know if you've ever done the long distance relationship thing, even though, you know, Boston, New York isn't, isn't that far of a distance. It's still distance. So it creates a whole bunch of challenges, but we finally got to the point in the relationship where there's kind of a breaking point. You kind of need to make a decision. And I think for the first time in my life, I had I chose something personal over something that was more career oriented. So I made the decision first that I was going to make a move to New York. I followed her. And that was a tough decision to go through because I loved what I was doing. I think investing is one of the most fun and intellectually stimulating careers that anyone can go into. And I loved my team and the types of companies and founders that I was working with, but t…

AI assessment note: “I made the decision first that I was going to make a move to New York”

Q Not at all. I'm excited, but I do want to kick off today with a little bit on you. So tell me, my friend, how on earth did you make your way from the world of venture to one of the fastest growing companies in history in UI path? What was that journey and transition for you?

A My transition, unlike most people, had nothing to do with professional ambition whatsoever. I was working for a enterprise software expansion stage focused venture capital firm out in Boston called OpenView Venture Partners. And I was there for four years working with a good friend and someone who I respect so much partnered there by the name of Mackie Craven. We're focused on the cloud infrastructure and data technology and Component practice of the firm. And I was also dating my girlfriend. We were doing distance. She got a really amazing job offer in New York. And I don't know if you've ever done the long distance relationship thing, even though, you know, Boston, New York isn't, isn't that far of a distance. It's still distance. So it creates a whole bunch of challenges, but we finally got to the point in the relationship where there's kind of a breaking point. You kind of need to make a decision. And I think for the first time in my life, I had I chose something personal over something that was more career oriented. So I made the decision first that I was going to make a move to New York. I followed her. And that was a tough decision to go through because I loved what I was doing. I think investing is one of the most fun and intellectually stimulating careers that anyone can go into. And I loved my team and the types of companies and founders that I was working with, but t…

AI assessment note: “My transition, unlike most people, had nothing to do with professional ambition”

Q to ask, I'm sorry to go off schedule this early, but I'd actually love your advice. Because I often face things where there's like that personal choice, and then there's that professional choice. And whenever I choose the personal, I feel really personally guilty that I haven't chosen the professional choice. I kind of shame myself. How did you prevent yourself from doing that? And how do you advise me?

A Well, I always listened to some advice that I got early on in my career while I was at Intuit. You know, our CEO there, Brad Smith, former CEO, I should say, he always said in life, you got to weigh the things that are rubber and those that are crystal. Things that are rubber bounce back. After some period of time, you'll, you'll never think about it again. Things that are crystal hit the ground, shatter, and you can't necessarily recover them. And, you know, I think things like a significant other, things like attending your kid's graduation or dance rehearsal, being at your parents' sixties, you know, those, those are things that are crystal. Um, you're not really going to get them back. And to me, when I did that, that internal text, the move into New York thing, the going for the girl felt like something that was crystal.

AI assessment note: “in life, you got to weigh the things that are rubber and those that are crystal.”

Q I absolutely love that. And I haven't heard that rubber and crystal before, but it's a good lens to look at the world through. I do want to also, you know, the transition, it's a big transition from venture to operating. So I want to ask, what have been the most surprising elements to you in your transition from investor to operator? Let's start with that.

A Yeah. You know, there's two things that really struck out to me in the first 12 months of this role. And so the first is you realize how much of a loan sport investing is. And it's not really a good or bad thing. It's just by nature of how investment teams are structured. You know, you, you work in deal teams of two to three people that are on the financing at any given time and really drive the relationship, the diligence, and ultimately work with company and the executive team post investment. You know, I, I contrast that, you know, with my current role where I feel like I'm going to battle every day, you know, with a full on army, me, Daniel, our CFO or CMO, In the thousands of people, you know, that we lock arms with to go capture this market, it's just amazing. We're in constant communication. We're all up to date on each other's priorities, constantly lending support, guidance, feedback. So it's really a true team sport inside the company. So that's .1. The second thing that surprised me is just how challenging it is to build a highly responsive company that allows customers to know that you care. The organizational complexity of Building teams across pre-sales, field, customer success, delivery channel, and then tying it all together into this cohesive experience that makes it pleasant and makes customers want to be part of that story. You know, it's really tough. One of…

AI assessment note: “there's two things that really struck out to me in the first 12 months”

Q I think that's a brilliant title that will confuse absolutely every listener. What's rubber and what's crystal by the 20 minute VT? Tell me, what would you most like to change about the tech ecosystem state? You've sat on the VC side, now you're on the operator side. What would you like to change?

A I think we've gotten to an era where there's just a lot of arrogance and entitlement in the ecosystem. As an investor, part of my job was talk to a bunch of companies and extract data points. But even today with, you know, our open ecosystem and our partner model, I'm still speaking with a lot of people. It's amazing. People, they get to like a 1,000,002 million dollars in ARR, and they think that, you know, they're God's gift to earth and this is, you know, they're like their next jobs or something. And I look at our company, which is over a quarter billion, and we never, Daniel in particular, never has that aura of arrogance around him. So, you know, I'd like everyone to just get back to being humble and building great products that solve really amazing challenges.

AI assessment note: “I'd like everyone to just get back to being humble and building great products”

Q I absolutely love that. And I haven't heard that rubber and crystal before, but it's a good lens to look at the world through. I do want to also, you know, the transition, it's a big transition from venture to operating. So I want to ask, what have been the most surprising elements to you in your transition from investor to operator? Let's start with that.

A Yeah. You know, there's two things that really struck out to me in the first 12 months of this role. And so the first is you realize how much of a loan sport investing is. And it's not really a good or bad thing. It's just by nature of how investment teams are structured. You know, you, you work in deal teams of two to three people that are on the financing at any given time and really drive the relationship, the diligence, and ultimately work with company and the executive team post investment. You know, I, I contrast that, you know, with my current role where I feel like I'm going to battle every day, you know, with a full on army, me, Daniel, our CFO or CMO, In the thousands of people, you know, that we lock arms with to go capture this market, it's just amazing. We're in constant communication. We're all up to date on each other's priorities, constantly lending support, guidance, feedback. So it's really a true team sport inside the company. So that's .1. The second thing that surprised me is just how challenging it is to build a highly responsive company that allows customers to know that you care. The organizational complexity of Building teams across pre-sales, field, customer success, delivery channel, and then tying it all together into this cohesive experience that makes it pleasant and makes customers want to be part of that story. You know, it's really tough. One of…

AI assessment note: “there's two things that really struck out to me in the first 12 months”

Q I think that's a brilliant title that will confuse absolutely every listener. What's rubber and what's crystal by the 20 minute VT? Tell me, what would you most like to change about the tech ecosystem state? You've sat on the VC side, now you're on the operator side. What would you like to change?

A I think we've gotten to an era where there's just a lot of arrogance and entitlement in the ecosystem. As an investor, part of my job was talk to a bunch of companies and extract data points. But even today with, you know, our open ecosystem and our partner model, I'm still speaking with a lot of people. It's amazing. People, they get to like a 1,000,002 million dollars in ARR, and they think that, you know, they're God's gift to earth and this is, you know, they're like their next jobs or something. And I look at our company, which is over a quarter billion, and we never, Daniel in particular, never has that aura of arrogance around him. So, you know, I'd like everyone to just get back to being humble and building great products that solve really amazing challenges.

AI assessment note: “there's just a lot of arrogance and entitlement in the ecosystem”

Q I mean, I didn't really listen to my own advice, but I totally agree with you. I do want to ask one personal thing though, and it's, you know, the company's changed so much with the scale, and you've been at the forefront of that for the last 18 months. How have you seen yourself change as a leader first, and then maybe as a person? Quite a deep question.

A Yeah, that's a really tough question. First of all, I look at the people around me and I say, wow, these are real leaders. These are people with 30 plus years of industry experience. They hail from large successful companies that they've either been intricate part of the story of, or several cases that have actually built themselves. They sit on big company boards and all that's just like the professional stuff. And there's no, the actual real life stuff. These are people that have gotten married, raised families, and experienced things in life that just given the constraints of time, you know, I haven't had an opportunity. I'm just a 30 something year old guy in New York trying to connect the dots as best I know how. You know, what I can say though, is that in the last 18 months on this journey, I've been changed in some pretty foundational ways. You know, I, I remember back to, you know, my first job right out of school, I was working for a big tech company on the West coast into it. And I was, every day I was just so focused on like getting to the next level, the quote unquote, climbing the corporate ladder. Everything was just, it was so tactical. It was, you know, get this partner signed up, release this feature, script this announcement. You know, do it well, get some hopefully some, some nice praise from whoever my manager was and try and move on. It was a very inwardly …

AI assessment note: “in the last 18 months on this journey, I've been changed”

Q I mean, I didn't really listen to my own advice, but I totally agree with you. I do want to ask one personal thing though, and it's, you know, the company's changed so much with the scale, and you've been at the forefront of that for the last 18 months. How have you seen yourself change as a leader first, and then maybe as a person? Quite a deep question.

A Yeah, that's a really tough question. First of all, I look at the people around me and I say, wow, these are real leaders. These are people with 30 plus years of industry experience. They hail from large successful companies that they've either been intricate part of the story of, or several cases that have actually built themselves. They sit on big company boards and all that's just like the professional stuff. And there's no, the actual real life stuff. These are people that have gotten married, raised families, and experienced things in life that just given the constraints of time, you know, I haven't had an opportunity. I'm just a 30 something year old guy in New York trying to connect the dots as best I know how. You know, what I can say though, is that in the last 18 months on this journey, I've been changed in some pretty foundational ways. You know, I, I remember back to, you know, my first job right out of school, I was working for a big tech company on the West coast into it. And I was, every day I was just so focused on like getting to the next level, the quote unquote, climbing the corporate ladder. Everything was just, it was so tactical. It was, you know, get this partner signed up, release this feature, script this announcement. You know, do it well, get some hopefully some, some nice praise from whoever my manager was and try and move on. It was a very inwardly …

AI assessment note: “I spend most of my days speaking with employees, trying to understand how I can help”

Q in terms of the distributed nature of the team earlier, and you mentioned Daniel inspiring the team itself. I do want to start on before we move into the quickfire. This is kind of the large part of leadership team being distributed. How have you made this work across the country? Now, this was a question from pretty much everyone on the board. So how have you made it work?

A All businesses these days are for the most part So distributed leadership teams aren't really something new. I mean, it's not something we invented. Time spent together is extremely valuable, and you learn to cherish that time, you know, with your colleagues because, you know, you never get it as often as you'd like. I'd say the biggest challenge is the cultural gap and bringing people together to better understand how you work. In different cultures, saying certain things can mean different things across the globe and picking up on those nuances. It's especially challenging, right? When founders or the original exec team is non-US, non-Western Europe, it's also a ton of fun because it creates a different learning experience beyond your quintessential, you know, corporate America entity where everyone's on the same floor five days a week. I think one thing that we did a really good job of early on, and it was a strategic decision, but it was building a hub and spoke type model where we knew we were going to be a global company from day one because we were born Right. Started in Romania and expanded to APAC, EMEA, and the likes. But we tried to place offices around a leader. Daniel is based in New York, so we have, you know, a lot of leadership in New York. London's a really great hub for us, and EMEA, Tokyo, and Japan. So we've got people spread in a bunch of different places, …

AI assessment note: “building a hub and spoke type model where we tried to place offices around a leader”

Q in terms of the distributed nature of the team earlier, and you mentioned Daniel inspiring the team itself. I do want to start on before we move into the quickfire. This is kind of the large part of leadership team being distributed. How have you made this work across the country? Now, this was a question from pretty much everyone on the board. So how have you made it work?

A All businesses these days are for the most part So distributed leadership teams aren't really something new. I mean, it's not something we invented. Time spent together is extremely valuable, and you learn to cherish that time, you know, with your colleagues because, you know, you never get it as often as you'd like. I'd say the biggest challenge is the cultural gap and bringing people together to better understand how you work. In different cultures, saying certain things can mean different things across the globe and picking up on those nuances. It's especially challenging, right? When founders or the original exec team is non-US, non-Western Europe, it's also a ton of fun because it creates a different learning experience beyond your quintessential, you know, corporate America entity where everyone's on the same floor five days a week. I think one thing that we did a really good job of early on, and it was a strategic decision, but it was building a hub and spoke type model where we knew we were going to be a global company from day one because we were born Right. Started in Romania and expanded to APAC, EMEA, and the likes. But we tried to place offices around a leader. Daniel is based in New York, so we have, you know, a lot of leadership in New York. London's a really great hub for us, and EMEA, Tokyo, and Japan. So we've got people spread in a bunch of different places, …

AI assessment note: “it was building a hub and spoke type model where we knew we were”

Q What do you know now that you wish you'd known at the beginning of your time with UiPath?

A I think this is just general good advice even before UiPath. You know, I think all of us tend to get really caught up in the moments of life. It could be a tough deadline for a project, something going on with your significant other, just a stressful life event. And the truth is that all this stuff is temporary. Life goes on. But it's really easy to get stuck on the negative things and let it consume you. And I don't think that's worth it at all. So, you know, I say just enjoy the ride. Don't sweat the small things. The hard part is knowing how to classify what's small in the moment, and the way to check that is to ask yourself, and what we started this podcast on, talking about what's rubber and what's crystal.

AI assessment note: “all this stuff is temporary. Life goes on.”

Q I totally get you, and, like, it's repetitive, it's boring, it's kind of low-level jobs and low-level kind of processes. My question to you is, though, from a societal perspective, is this not replacing or partially replacing the jobs of these people in these maybe lower-level process-orientated jobs, and how do you feel about that and respond to that suggestion?

A Yeah, it's a great question. We live in a world of analogies. So rather than just give you a simple, yeah, it's replacing or no, it's not. But let me tell you an interesting story about a Russian chess grandmaster, really the greatest chess player to ever live, a guy by the name of Garry Kasparov. So this is a guy who from 1986 until his retirement in 2005 was ranked the number one chess player in the world for some ridiculous amount of time. It was like 225 out of 228 straight months. And there's this You know, great moment in history. I don't know if you recall, but in 97, this guy lost to IBM's supercomputer, Deep Blue. And this match was the first defeat of a Reagan world chess champion by a computer under actual tournament conditions ever. And this created, you know, a ton of press and news about the race between man and machine. It's obvious why it was significant. This was a sign that AI was catching up to human intelligence and could defeat any one of humans' great intellectual champions. What's interesting, we fast forward to today, Over 20 years later, that paradigm isn't the case. Today, a computer is no longer the world champion, and actually, neither is a human. Today, the best chess matches in the world are played by a combination or team of humans and computers, and what's even more interesting than that to me is that the best teams have no grandmaster and no sup…

AI assessment note: “a team of human plus robot working together Beats any standalone person or machine”

Q The single best investor meeting that you've ever had, Brandon, and why?

A Well, the best investor meeting that I never had is actually a better story. Several months ago, my, our CMO, Bobby Patrick, and I were invited down to New York Stock Exchange to witness a public offering of another tech company, and it, you know, it was a really, it was a really exciting event for us. You know, we got a private tour of facilities, front row seat, and the bell ringing, and we were feeling a bit high that day. We were, we were levitating above ground a little bit, and we happened to be 10 feet from Jim Cramer as he was about to get on and do his show, and we were with this woman, the president of the New York Stock Exchange, and we said, hey, do you think it'd be possible for us to I mean, of course, we're with the head of marketing. Of course, he's going to want to see if we can get something in front of Jim. So we asked him, hey, can we say hi to Jim Cramer? And she goes, let me, let me see, you know, he's, he's getting ready for work. Let me see if we can get him. She goes over and we could hear what she was saying. We were close enough. And she said, hey, Jim, you know, we're with this really interesting automation company, UiPath, just raised an evaluation. They're doing all this stuff. Would you be interested in chatting with them? Just saying hi quickly. And he looks up from his piece of paper. He goes, I've never at the end heard of them. And just walked…

AI assessment note: “the best investor meeting that I never had is actually a better story.”

Q early stage founders, I'm absolutely for the vulnerability, but they go, Hey, I can't be that vulnerable. If I admit to market that I'm struggling like hell, my head of sales just left and I've lost my biggest client. You know what? Funding will be quite hard. How do you think about kind of vulnerability for startup founders? And what would your advice be there if you think about that?

A Yeah, it's a tough line. I mean, it doesn't mean you want to go out into the world telling them every little intricacy about your business, all the fears that you have at once. But you can show leadership in different ways. And leadership to your employees can mean, you know, one thing. Leadership to your customers can be another. Leadership in front of investors can mean something completely different. And it's just how you present it. And it's not about making up a different story or changing the messaging. It's about how you're presenting yourself and how genuine you're being. And people pick up on that, right? It's, it's not really what you're saying. It's really about how you're saying it.

AI assessment note: “it doesn't mean you want to go out into the world telling them every little intricacy”

Q early stage founders, I'm absolutely for the vulnerability, but they go, Hey, I can't be that vulnerable. If I admit to market that I'm struggling like hell, my head of sales just left and I've lost my biggest client. You know what? Funding will be quite hard. How do you think about kind of vulnerability for startup founders? And what would your advice be there if you think about that?

A Yeah, it's a tough line. I mean, it doesn't mean you want to go out into the world telling them every little intricacy about your business, all the fears that you have at once. But you can show leadership in different ways. And leadership to your employees can mean, you know, one thing. Leadership to your customers can be another. Leadership in front of investors can mean something completely different. And it's just how you present it. And it's not about making up a different story or changing the messaging. It's about how you're presenting yourself and how genuine you're being. And people pick up on that, right? It's, it's not really what you're saying. It's really about how you're saying it.

AI assessment note: “it doesn't mean you want to go out into the world telling them every little intricacy”

Q I totally get you, and, like, it's repetitive, it's boring, it's kind of low-level jobs and low-level kind of processes. My question to you is, though, from a societal perspective, is this not replacing or partially replacing the jobs of these people in these maybe lower-level process-orientated jobs, and how do you feel about that and respond to that suggestion?

A Yeah, it's a great question. We live in a world of analogies. So rather than just give you a simple, yeah, it's replacing or no, it's not. But let me tell you an interesting story about a Russian chess grandmaster, really the greatest chess player to ever live, a guy by the name of Garry Kasparov. So this is a guy who from 1986 until his retirement in 2005 was ranked the number one chess player in the world for some ridiculous amount of time. It was like 225 out of 228 straight months. And there's this You know, great moment in history. I don't know if you recall, but in 97, this guy lost to IBM's supercomputer, Deep Blue. And this match was the first defeat of a Reagan world chess champion by a computer under actual tournament conditions ever. And this created, you know, a ton of press and news about the race between man and machine. It's obvious why it was significant. This was a sign that AI was catching up to human intelligence and could defeat any one of humans' great intellectual champions. What's interesting, we fast forward to today, Over 20 years later, that paradigm isn't the case. Today, a computer is no longer the world champion, and actually, neither is a human. Today, the best chess matches in the world are played by a combination or team of humans and computers, and what's even more interesting than that to me is that the best teams have no grandmaster and no sup…

AI assessment note: “combination of knowledge workers and robots will transform the enterprise”