Vikas Gupta, CEO of Azibo: From Consultant to CEO, Nurturing Relationships, and Deciding on Business School

Vikas Gupta  00:00

If I find opportunities that might be of interest to people, I send it to them because I think it might be interesting to them not, again, not through like any calculated network maintenance, but just more of like, I want good people to have good opportunities. I think other people want me to have good opportunities. And so let's just all try to create a better environment for each other.

Callan Harrington  00:19

You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here. Welcome back to another episode of That Worked. On this week's episode, I'm joined by Vikas Gupta. Vikas is the CEO of Azibo. Azibo provides a free unified, financial and property management platform to independent real estate investors in the US. Vikas has done a lot. He's been a founder, a head of product, a head of marketing, all at various startups ranging from pre seed to Series B, across consumer B2B, SaaS, and enterprise data. He also spent time at LoopNet and McKinsey, and we went deep on a couple of topics in the episode. One of my favorite topics is the career path of consulting at a company before joining it. I think it's an excellent path. He walked us through how he personally did this and ultimately became the CEO of the company he joined. We spoke about his decision to go to business school. He gives a great breakdown and a really honest answer as to how he evaluated this and why he ended up doing it. And then we also talked about the importance of networking, and more importantly, how to nurture those relationships throughout your career. This was a fun episode to record, so I'm going to get right to it. Here's Vikas. Today's guest, we have Vikas Gupta, and Vikas is the CEO of Azibo. Vikas, welcome to the show.

Vikas Gupta  02:12

Thanks, Callan. Glad to be here.

Callan Harrington  02:13

Yeah, well I'm excited to have you on the show. How did you get involved with Azibo? Just at all? How did you originally find them? How'd you get involved?

Vikas Gupta  02:24

Yeah, that's a good question. So I was coming off of a period where I had just shut down my own startup. And I was taking a few months off - a forced sabbatical. And then after about a month of forced sabbatical, I got bored.  And started reaching out to folks to see if they had any interesting opportunities, interesting companies I should be talking to. So I reached out to Rich Boyle, who led the seed round into Azibo. He's a GP at Canaan ventures. He, when I met him, was the CEO at LoopNet.com. And I worked for LoopNet from 2006 to 2009. So that's where I got to know Rich, and Rich started telling me about Azibo. And when I took a look at the website, and I looked at the founding team, it turns out that Chris Hsu, the founding CEO of Azibo, was my boss at McKinsey and Company in 2005. And so I said, "Hey, you know what, like, I have to talk to you like, it's been a while since I've talked to Chris; let me talk to Chris and see what he's up to." And so I started talking to Chris, and this was, I think, January of 2021. And started doing some consulting work for the company, and over a few months, got to know the company. It was great to get back into that working relationship with Chris. I really liked what the company was doing. I thought that there's a clear need in the space. Most of the technology enablement in this space has been targeted towards those institutional-scale real estate investors and institutional-scale property managers, and this sub-segment of the market where, frankly, most of the units in the SFR space are, and most of the owners are. Eight million real estate investors who aren't using professional property managers who own somewhere between 35 and 40 million units. So, huge market. They've largely been left behind by technology. And it's only in the last few years where the FinTech infrastructure has been built, such that an early stage company would be able to combine payments, banking, accounting, plus the property management workflows in one place and be able to feasibly do that at early stage scale. So wonderful market opportunity. The "why now" made sense, not possible 20 years ago, while the expense of 10 years ago only sort of possible in the last few years, as I said. And I love the team! And so Chris asked me to come on full time as Chief Operating Officer, and so I joined in April of '21. And then in Q1 of 2022, Chris decided that he wanted to take a step back after three years of getting us from an idea on a whiteboard to a Series A well-funded company, he decided the time was right to make a transition. And he and the board decided to elevate me to be CEO. And I took over in April of '22.

Callan Harrington  05:22

Here's what I'm curious about - when you were consulting, were they were they looking for a COO? Was that on the radar? Or did that become, "we've started to work with Vikas, and Vikas could be a great person for a COO, so let's make that move." What did that look like?

Vikas Gupta  05:42

No. So there was no active search at the time. It's not like there was a job posting or an executive recruiter going around saying, "hey, Azibo's looking for a COO." I think, through the course of me doing the consulting work for Chris, it became clear, I guess to him, that there was an opportunity to bring in someone with my background and my experience in startups. And it became clear to me that there was a great opportunity to join a company and have impact. I think that was sort of obvious to us. And then it was a question of, alright, what's the role? What's the title? What's the responsibility said? And I think especially for early stage companies, that's almost the better way to go about things; which is, alright, someone comes in as a consultant - obviously in this case there was a pre-existing relationship - especially if there isn't a pre existing relationship to sort of try before you buy on both sides frankly, not just for the company, but for the individual executive as well. And then see if there's an opportunity to have impact on the company. That's the most important. Then you can decide like, what do we call it? How do we title it? What is the actual role responsibility, JD? But that, I think, is the better way to go. As opposed to you know, sometimes you have to start with the JD, but when you have these sort of opportunistic hires, so to speak, it's much more about do we think there's an opportunity to create impact on both sides? Once you do, you can start putting pen to paper and sketching out what you're going to call it, but what you're going to call it is secondary to is there an opportunity to have impact?

Callan Harrington  07:11

I totally agree. Do you think that people are more nervous to do that, because of - almost kind of nervous to take a year to consult? Because I've heard before some people are worried about, well, if I do that, then that's going to look - that's gonna look like I couldn't get a job or whatever that may be. Did you have any of those concerns when you're going through this?

Vikas Gupta  07:33

I personally didn't have any of those concerns, because I wanted to take the time to find the right role for me. And so I told myself, however much time it takes to find what I think is the right opportunity for me, I'm going to take that time. And I didn't think three months, six months, frankly, even nine months of downtime, would have been much of a red flag on my resume. I think everyone understands needing to take some time off. And, you know, especially looking for the right executive role that can take time as well. So I had none of those concerns. The harder part, frankly, is the sort of managing the personal cash flow. And I was fortunate that at the time, I was in a position where I didn't really have any major cash flow concerns. That I think is the challenge, right? If if your personal burn situation, you know, you have a house, you have a family, you have kids, such that like, you need to go get that guaranteed paycheck next. I think that's what makes it tricky. And certainly, I think that would make it trickier for me, if I were in a situation where I couldn't easily go a few months making half of what I made before, just to find the right opportunity for me, because early stage startups, seed stage startups, like it's hard to pay, you know, full freight on a trial basis.

Callan Harrington  08:57

I think that's that's great advice on you know, making sure how long can you do this? And what kind of cash do you need for for you? So, well, cool. I want to circle back to this. But you started out McKinsey, right. Is that correct? Is that when you started your career out?

Vikas Gupta  09:11

That was my first full time job. I think, the destination I mean, I guess like if I think about my career in general, it's sort of it's a combination of good fortune, hard work, and planning. And I don't know what the relative weight of all those things are. It's probably even, if not more skewed towards good fortune. And so my sort of destination into, or my route into McKinsey is interesting in and of itself. So I went to UCLA for undergrad, which is at the time - I don't know if it's changed - but at that time, was not a core recruiting campus for McKinsey. So they didn't have any recruiting presence. And if you weren't on a core school, you sort of had to find your way in, and I did an internship at a Merchant Bank in Beverly Hills. And again, very, very fortunate in personal circumstance, where I could take an unpaid/ low paid internship for experience. And the deal that I made with my manager, or the deal he made with me, was do a good job here, there may or may not be a role that's of interest for you here, but if there isn't one here, then I will do everything I can to get you the job you want after undergrad. And so I worked there, and I wanted to go into consulting and he said, alright, like, I will get you your interview at McKinsey. And so he called up someone he knew. And that, frankly, like, that's how I got into the recruiting process. Now, I was able to get through the recruiting process, but the only reason I was able to get in is because he was able to pick up the phone and call someone. And, you know, I applied to an internship posting off the UCLA Jobs website to get that internship. So a lot of sort of good fortune and luck, combined with hard work and relationships is sort of what got me to McKinsey.

Callan Harrington  10:57

What was it like once you got there?

Vikas Gupta  10:59

Oh, it was awesome! I loved it. As like a 22 year old business nerd, being there with a bunch of other business nerds, working on, I think, fun problems in an environment that really honed critical thinking, data, teamwork, and communication. As a first job, as a place to really like train your mind, I think it was fantastic. And then all the stuff that would cause me to not want to go into consulting today was less relevant to when I was 22. Like travel, awesome. Getting to, you know, eat fancy meals and not worry about waking, awesome. Seeing different cities, working on different problems. The sort of like, the switching from client to client was a benefit at the time. I think now I'm much more of a like, I want to be in one place and drive impact and have more ownership. But again, like 22-23 for two years, just the learning environment was amazing. And so I loved the job for two years. After two years, I was ready to move on. But for two years, I loved it. And I can't think of a better place to start my career.

Callan Harrington  12:06

Do you think that there are things from McKinsey that still impact your career as it stands today?

Vikas Gupta  12:11

Absolutely. I think relationships. I think the way that I've been trained to think and break down problems into constituent parts.

Callan Harrington  12:19

Could you walk us through that?

Vikas Gupta  12:22

I mean, it's just every firm has their own format for the way they make slides. And so like if you're familiar with the way McKinsey made slides, circa 2004, 2005, 2006, like you can tell that I worked there. I don't have experience with other consulting companies. But I've heard that like, if you've hired Bain, if you've hired BCG, if you've hired McKinsey, or if you have experience working with teams across those three, you can tell where someone came from based on the way they make their slides. It's like a fingerprint. I've also heard that like, you can tell if someone came at it with specific investment bank based on the way they built their models. So it's probably similar.

Callan Harrington  12:56

Which makes complete sense, right? You get in, and I still think of like even I was at an advertising agency and learning that type of pitch deck kind of sticks with you. It's more storytelling than anything else, like telling that story, which, to me is super valuable. And the level of design quality, that was something that still sticks me to this day, like if something's not designed well, and I am no designer, but I understand that, the value and the importance of it, that never goes away.

Vikas Gupta  13:26

Well, the funny side for me is, so in 2004, 2005, 2006, when I worked there, format was all black and white grayscale, because at the time, you couldn't necessarily rely on clients to have color printers. And so like ever since then, I don't know how to use colors. Like I never had to use colors, right? So like, I know how to like use grayscale, but I don't know how to use colors in slides. So whenever I have to use colors, if I don't have like, a template that I can work with, it just looks terrible.

Callan Harrington  13:53

So you said you were there for two years, and then then you went over to LoopNet? Why the change?

Vikas Gupta  13:57

I wanted to get into tech. I thought that tech had the best opportunity for someone like me to, frankly, like move quickly through the ranks. I had experience with large companies at McKinsey. And it just seemed a little too slow for my liking. And I thought that going into technology would get me exposure to much faster changing, more dynamic organizations. And that would give me an opportunity to progress my career faster. I mean, I actually started by- I originally wanted to go into venture capital. And through my McKinsey network, I was able to get introductions into a bunch of different VC funds. And sort of universal feedback that I heard at the time was go get some operating experience, and then come back, because right now, there's really not much you have to offer. I forget who told me that phrase. I think someone used the phrase like "you're a generic smart person right now, but there's a lot of generic smart people, so go get some operating experience, maybe you'll be a little bit less generic." And so I started looking at, alright, what are technology companies that I could work for? And LoopNet's, at the time I believe he was the VP of marketing, but he became the president over time. And then the GM of one of their business units BizBuySell.com. Both gentlemen were ex McKinsey guys. And so I got introduced to them through a partner who I'd worked with. They had known, you know, that ex McKinsey analysts could do a bunch of different things. So they created a role for me with the understanding that I'd be there for two or three years and go to business school. So it was sort of fully understood, on all sides, sort of, you know, I'm gonna be there for a short stint. And I'm there to learn a lot, and there to get what they can out of me, and then I'll go off to business school. And it was a fantastic opportunity, because I did special projects, got exposure to every single operating function of a startup. At the time, I was too early in my career, to know this, but looking back, they were an incredibly high functioning, well run organization. And so it's just being steeped in that learning, that doing projects everywhere, spanning from marketing analytics, web analytics, Salesforce compensation redesign, implementing an ad server and running the third party ad networks, monetization strategy, product pricing, the gamut of projects. Did some M&A, like really getting exposure to a high functioning technology company, and then also getting a front row seat to a management team that had just gone public, and then had to manage through a real estate business through 2007, 2008, 2009. And how they did that. And so it's just a fantastic learning experience all around. Plus, then I got to meet great folks and got to work with Rich increasingly as I stayed a little bit. Early on, not much exposure to him because he was the CEO, but as I took on more responsibility got more exposure to him. And that's obviously a relationship that's paid off as well.

Callan Harrington  17:07

What were some of those things that you learned there? When you mentioned that this was something that was super high? Just a really efficient, well-ran? What were some of those pieces that you had picked up?

Vikas Gupta  17:18

Yeah, I mean, I think one thing that stands with me is like, I think we're getting there at Azibo, but relative to many other companies I've worked for, and this was in 2006, so like pre-SAS explosion, they had the best data and analytics infrastructure, almost any company I've seen at that stage. And so just having full insight into the business, having rich data that lets you run predictive models, having a really high caliber analytics team that's able to build those models and drive the business. They had a data lead scoring model, that every day would rank, everyone based on propensity to buy a premium membership, take off the top X percent of those leads, distribute them to the sales team. And they had that sales machine down to a science. And it was known, hey, if you're an effective sales rep, and you make your 50 calls per day, that you should get your 35 sales per month. And because we know the quality of our leads, and we know when people are likely to buy, and we know what the sales script is. So if you make your 50 calls, like you'll get your sales, and then the whole machine works. And that was incredible, right? Like that level of science, in a sales organization, pre-SAS, right, pre- all of these lead scoring tools and AI driven models and big data. And this was all running off of you know, SQL Server and homegrown models.

Callan Harrington  18:47

They were way ahead of the curve when it came to, how can we get predictive and what we're doing so we can have more accurate forecasts. And as a result, we can decide which levers that we want to pull in order to expedite our growth. One of the things that you mentioned is you had already made the decision before going to LoopNet that you were going to business school, is that correct? I guess a couple of things. Why was going to business school important? And why was it kind of a foregone conclusion that that you were going to do that? How did you come to that decision?

Vikas Gupta  19:18

At McKinsey at the time, I was an analyst, and so analysts were generally straight out of undergrad. And then you have your associates who sort of like a another semi-entry-level position. But they typically come in out of grad school, the majority of which came out of business school programs. And every single person I spoke to, in the Associate Program, who came out of business school said, "go to business school, it's going to be two of the best years of your life."

Callan Harrington  19:46

So was this more of, "I'm gonna have fun?" Okay, so it was "I'm following this path. Everybody loved that. This is where I'm going." Was that the main kind of deciding factor for you?

Vikas Gupta  19:58

Yeah, that was the main factor for me. I mean, there's there's obviously right, there's a lot of benefits, right? There's the network benefit of business school. Most of them had told me that the educational benefit of business school, at least from the curriculum, is going to be relatively low given that I had studied a lot of business topics in undergrad, and then I had gone to McKinsey, and then I had two more years - three more years of work experience after. But you know, you learn a lot from the experiences of other students who you're in class with, and you just get to make great relationships and have a lot of fun. And then it's also an opportunity to experiment with internships with projects, it's very easy to, for whatever reason, if you pick up the phone and call someone and say, "Hey, I'm a student; I have some questions for you." They'll answer the phone for whatever reason. So it's somehow like socially less acceptable to do that, if you're not a student. Doesn't make any sense to me. But just carrying the student title, like, lets you get access to people. And so, you know, those were all like, secondary benefits that were in the back of my head. But yeah, I mean, the main thing was, like, everyone had said, "This is gonna be two of the best years of your life." It was amazing. I loved it. It was so much fun.

Callan Harrington  21:10

So I got a couple of questions. What about it was amazing? And then looking back on it, what were some of the benefits that you had out of it, that you got out of it just in general?

Vikas Gupta  21:22

Other than undergrad, and then graduate school, I can't think of another time when you're with a bunch of people in the same age, going through the same experience on the same schedule. And so the on the same schedule part is important, because, like, I guess there's, there's a reputation of business schools travel a lot. And certainly I traveled a lot. But like, you're with a bunch of people who are at the same place in their life, who like- who are largely of similar mindsets, who are trying to do largely similar things, who are also on the same schedule. And so like, it just creates an opportunity to have a lot of fun, because it's not like oh, like, you know, I can't take these two weeks off. It's like, well, we all get the same time off, we all have the same class schedule. The school I went to, Friday's didn't have classes. So we all had Fridays off. And so it just creates a propensity for, whether it's weekend trips, or nights out or large trips overseas, just being on the same schedule creates a lot of opportunities to do things that it's just harder when everyone is, you know, sort of running their own life.

Callan Harrington  22:28

Makes complete sense. What would your advice be to somebody that's considering business school?

Vikas Gupta  22:32

A lot of it depends on what you want to get out of it. And that depends on your own motivation. So if we sort of segment what are the value drivers at business school. Let's take education, for example. So if you're coming from a non-business background - you didn't study it in undergrad, you didn't work in a specific business function in, you know, in between undergrad and when you're thinking about going to business school - then you're going to learn a lot of basic business fundamentals in business school: finance, accounting, marketing strategy, like just core fundamental. Nothing about the curriculum is unique, right? Like, you could do open courseware, you could look on YouTube, you could teach yourself this stuff. But that's where sort of the personal motivation comes in. If you benefit from the structured, like, I'm forced to do this, I have classes that have homework. There's value there, right? So that's the education. Second, I'll take career in recruiting. There's a very structured recruiting process in business school, that if you don't have access to it, it can make it harder to get certain types of jobs. So if you want to go into consulting, you want to go into investment banking, they recruit out of business schools. They'll come to campus, you apply, they'll do internship programs for people on campus. And that is a very exceptionally hard to get into certain fields if you don't go through these doors. And so there's value there as well. Now, let's take the network, you know. There's the alumni network, and then there's the people you meet and make friends with. The alumni network side, right? Again, people are much more willing to pick up the phone, if you have some reason to reach out. So they'll have alumni directories. You can look up people, you can call them, there's an instant connection there, something to talk about that can help. And so there's value there. And then from the relationships you build, there's sort of personal life value, and then there's career value. Many of my closest friends today, I made through business school, and traveled together, we share a life together, we've gone to each other's weddings, first kid's birthday parties. Like you know, we, we went to school when we were 27, 28, 29. Now I just turned 40. We sort of like become more fully fledged adults together. And so that, you know, there's something about like, making like, friends contribute a lot to your life and you meet people who are similar to you. And then from a career perspective, you have your alumni network. Or people in your class who you went to school with who you can hire, who you can call, and that's certainly been a source of value to me as well. So those are sort of like some of the key value dimensions. What does that mean for an individual? They have to make their own decisions about where are they in their life. What opportunities they have, what access to these networks do they have independent of these things? What industries do they want to go into? And how much of going to school or not going to school is the gating factor to going into that industry? Do they have to pay for it? Does someone else have to pay for it? What is the, you know, fiscal situation that they're in? These are all things that I think make an individual decision. So I can't say whether or not it makes sense for any given person to go. But I think like you sort of have to think across these different value drivers, and then you can make up your own decision about whether or not you want to go.

Callan Harrington  25:36

That is interesting. I have not looked at it from the standpoint of, you know, you're kind of going through this shared experience with other people. And you're a little bit older at that point, which is really interesting. Actually, it's almost like you're, you're on the cusp of being a real adult and starting to make that transition at that point. It's almost like a last hurrah. So after that, and it looks like, and correct me if I'm wrong, but you were a summer associate. So I'm assuming that was an internship at Rustic Canyon Partners. Which the company that you went to after was Factual, which is a portfolio company of- at the time- of Rustic Canyon partners, if I understand that correctly?

Vikas Gupta  26:13

No.

Callan Harrington  26:14

It was not? Okay, what was that?

Vikas Gupta  26:16

So, LoopNet was a portfolio company of Rustic Canyon partners.  So if you remember, I'd said, you know, coming out of McKinsey, I wanted to go into venture capital. And I wasn't able to get in, they said, go get operating experience. So then I went to LoopNet. So then I went to business school, but I still had my "I want to work in venture capital" dream in the back of my head. And Rustic Canyon partners was one of the premier, early-stage VCs in Los Angeles at the time. The LA tech community was significantly smaller than it was today. So there were only a handful of local VC funds, and they were one of them. And they had a lot of connections to UCLA Anderson, they were looking for a spring - summer associate. And they had invested in LoopNet. So I asked Rich, "hey, can you give me a warm recommendation into Rustic Canyon?" Which worked out. And so I worked there for six months. After that experience, I decided, you know what, I don't think venture capital is for me.

Callan Harrington  26:21

Okay.  What made you decide that?

Vikas Gupta  27:18

What I know today is that at the time, I did not know how to think about early stage investing properly. And I think it's a very different mindset than someone who had come through my background of college, McKinsey public company, and then business school. And, you know, the early stage investing mindset is, has to be very much like what do I think this could be? Not, what does it look like today? Because nothing, almost nothing today looks good. When you're looking at like seed Series A companies. Why? Why would you? Like a risk adjusted basis, like base- if you're like, traditionally trained, you're like, none of this makes any sense to me. I don't think I fully recognized it. I don't think I could describe it that way at the time. I didn't have the language to describe that. But something in my head was like, this doesn't feel right to me. I don't know how to think about this properly. I couldn't have said that. But that was like, this doesn't feel right to me. So that was one thing. The other thing was, and it's still frankly, with me today, I've learned a lot about how to do this. But I am not the person who likes to go out to an event and shake every hand and meet every person. And there is an aspect of generating deal flow that that requires. And that was just not, not my strong suit, not something I enjoyed doing. So if you sort of say, hey, like, something about how to evaluate these businesses doesn't feel right to me. And the whole, like, generating fuel for process is not fun for me. It just like wasn't a fit. And so fortunately, I realized that. And then I started deciding, hey, I want operating roles. And let me figure out who are the companies in LA I should be speaking with. And I talked to the Rustic guys, I talked to- again, like, I think there were like five local VC funds in LA at the time or something. And so I was able to talk to all of them. I think every single one of them said some version of- Gil, who's the founder of Factual, Gil is doing something interesting. We don't really know what it is. But he's the type of guy where if he's doing something interesting, you want to be a part of it. And so with that, sort of in my head, I said, alright, let me go talk to these Factual people. Eva Ho, who was running marketing for Factual- Rustic had invested in what her previous startup, and so they were able to give me an intro to Eva. And then Eva brought me on as an intern. And then I was able to parlay the work that I did as an internship into creating a full time role for myself, and then ended up sticking around there for about six years.

Callan Harrington  29:42

Gotcha. Okay. So, again, I mean, it's a similar theme, right? It's the theme that we kind of started this with, is you had that opportunity to try before you buy, right? In this scenario, it was in kind of an internship capacity. And this- is this is one of the, probably one of the most common themes on the show just in general. Where, I can't tell you how many times somebody has come on and was like, this was my dream job, like I wanted to get here, and this is- I was doing everything I could to get here, got in the job, not what I thought. The idealization of what that job is, versus the reality once we're in it, are often so different where, you know, I used to think this was crazy. You know, you heard it in business books, especially entrepreneurship books for years, right? Go in there and sweep the floors, if you can sweep the floors. You want to own a restaurant? Go volunteer. And I was like, that's the stupidest thing I've ever heard. Like, that is such a waste. Why would I do that? That's such a waste of time. Like, if I'm going to go in here, I'm going to be a manager or whatever that may be. Now when I think about this, it's like, I'll sweep the floors. I just want to get a feel for like, will I even like this? What is the lowest risk measure that I can take to try this out to decide? Do I even like doing this? Because if go to just commit to that, if you would have just went that VC full time, what are the odds that you would have just after six months- you probably would've gave it some time, right? And six months- you could be hating that- but were you just gonna say, "nope, not for me." Highly doubtful, for all the reasons that you mentioned before you built these relationships, they helped you get in there. So yeah, I think and I would say this, especially if you're earlier in your career, where you typically have more- like you mentioned earlier, right and personal cash burned may not be as big of a concern earlier career. Go try something, not necessarily maybe be able to get an internship. But if you can find somebody, shadow them for a day, any of these things that you can think of to get a feel for, you know, what that job is. Because you may see it and think, "this is not what I thought." So I think that's such a good route to try that. So I want to fast forward a little bit. So you're at Factual, worked your way to the ladder. You know, your business school is behind you, you can kind of sink your teeth into whatever you were doing it at this point, moved up to an executive level. I think you took a brief position at the Baby Box Bompany, is that correct? And then you started your own company? Why did you want to start your own company?

Vikas Gupta  32:09

I can't remember when I wanted to start my own company, when that first crystallized. But for a long time, I thought, "I want to start my own company." And it was almost like the challenge of can I do this, but I was, you know, I had to wait until I found what is something I'm passionate about? What do I think, is a solution that I can bring? What is a problem that I want to solve? Because starting a company for the sake of starting a company is not a recipe for success. So I had to wait until I actually had the right idea or what I thought was the right idea. So I had this idea around facilitating a more structured or a better process for career growth and professional development, specifically focused on the relationship between managers, individual contributors. And really trying to give a tool to individual contributors take more control over their own career growth. And sort of the genesis of the idea was sort of seeing what McKinsey had from a very structured, very programmatic, well designed, honed over generations of people doing the same job, professional development and growth journey, and then going into operating companies that don't have the same level of ability to invest in their people functions, have fifty unique job functions - whereas at McKinsey, we add Analyst, Associate, Engagement Manager, Associate Partner, Partner, Director, right, we had like six. And then also when you start getting to more and more early stage, you don't have the time or the bandwidth, and you have a lot of first time managers, and you have all this, you have basically the exact opposite of the infrastructure McKinsey yet, but it's still vitally important. I know that when I first started managing people at Factual, I struggled heavily with how do I create the right growth environment for people on my team. And what I learned, which in hindsight, is not that much of a learning (sort of self evident), but it was a learning to me at the time, is the individuals who pull the growth, who pull the feedback, who really sort of take more control over their careers are the ones who got the most out of me, and the ones who got the most out of the organization, right? The person who is coming into the one on one with these are the three things I want to talk about. Can you explain to me what the company's doing over here? Every three months saying, let's look back, where am I in my career? What do I need to do better? What's the next step? Like those are the ones who got more out of me as a manager than the ones who just sort of came in and said, these are the things I'm working on and sort of waited for it to come to them. Now like that's obviously, ideally I could have done right by them too, but just the reality of the world is the people who demand it are gonna get it more than the people who don't demand it. And so I wanted to create some sort of software tool to make it easier to demand that, and track it, and hold people accountable, not just the manager, but also frankly, the individual. Becuase if the individual is saying, you know, I need this, then the manager creates the opportunity that they actually execute on. So that was sort of the genesis of the idea. And I felt like I wanted to do it. But I wasn't so sure that I wanted to go raise money immediately. And so I did a EIR role at Alpha Edison. And going back to relationships, one of the founding GPs at Alpha, Nate Redmond, was a GP at Rustic Canyon. So that's how I got to know Nate. And then the other one of the other founding GPs at alpha Edison, Nick Roth, he was a business partner of a gentleman named David Waxman. And David Waxman was a GP at TenOneTen Ventures, which is also where Gil, who was the founder of Factual, was a GP there too. So like all these relationships in the LA tech world, right, led to them, and so- and they had invested in Baby Box, and that's how I got into Baby Box, I got to know them better. They offered me an EIR gig. I spent six months there, doing market research, learning how to code, building a prototype, testing the prototype with some folks, gaining more confidence, both that I felt like there was a problem to be solved here, but then also that I wanted to go commit X years of my life towards solving it. And that I wanted to ask people to give me money to go solve it. So then I raised a pre-seed round from again, my relationships, Alpha Edison, TehOneTen, and Fika Ventures. Fika, which is where Eva Ho was the founding GP, and she was the one who hired me to Factual, and then you know, off to the races.

Callan Harrington  36:28

How do you nurture these relationships?

Vikas Gupta  36:30

It's a good question, I probably should be doing a better job at it. I mean, I think the way that I think about it is there's, there's a few different elements. The first is is that it can't or shouldn't be all one sided. Although when you're junior in your career, it ends up being, I think, more perceived as one sided because you have less you can contribute. But as I've gotten more advanced in my career, it is more common for asks to come my way. It is still not as common as me sending out asks at this point. But whenever those asks come in, try to be very responsive and, you know, handle them. And that sounds very transactional, but frankly, like, I'm happy to help people, right, like, they're genuine- I feel like they're genuinely happy to help me, I'm happy to help them. There's another element of if you fundamentally believe that you're good at what you do, then it is beneficial for both people. So like, I genuinely believe, rightly or wrongly, but I believe I'm good at my job. And so me asking rich, Hey, who do you think has an opportunity for me? Well, Rich also has a vested interest in making sure his companies find good people. And so creating more liquidity in the market is beneficial for everyone. Now, you're still asking people to do things, but it's not like, I'm bad at my job and asking them to hire me anyways. Right? And then I think it's, you know, just just the third piece is being genuine with people. And, you know, when you're at the same event, like making sure you go say hi to the people that you know, and taking interest in their lives. And when, you know the other day, I went to the Carta homepage, and I saw a picture of Eva. She was like on the Carta homepage. So I took a screenshot and sent it to her. Not because I was like, "oh, let me maintain my relationship." I was like, genuinely excited. I was like, "this is awesome! Like, Eva, you're on there!"  I mean, she is a remarkably successful person and has been for twenty years. So I don't know where that rates on, like, her personal level of success. But I'm like, "you're featured on the Carta homepage! Look who I just ran into!" And I sent her a note, you know, like, look, how are you doing? Right? And, like it was, it was from a genuine place. It wasn't calculated, like, oh, I haven't emailed her in 275 days, let me find something to email her about, right? It was just genuine, like serendipitous, like, oh I see you - let me send... And you know, if I find opportunities that might be of interest to people, I send it to them, because I think it might be interesting to them not, again, not through like any calculated network maintenance, but just more of like, I want good people to have good opportunities. I think other people want me to have good opportunities. And so let's just all try to create a better environment for each other.

Callan Harrington  39:18

I think the key is what you said, and it's, you know, how can you put yourself in position to find those articles. So when you do come across one of those article- I'm using article as an example, an article comes up that you do find really interesting, but you've taken the time to know why that why would that be interesting to Vikas? If I sent you an article, and I said, "hey, Vikas, this is something that I found interesting. Here's why I thought you would you'd get value out of this." And there's no ask, and that's it. And I think that's one of the- it's a great way to nurture a relationship just in general. I tell people all the time like don't ever stop. Never, never, ever, ever pull your foot off the gas on on networking and building relationships, because you have no idea where they'll take you when that will happen, where that will be. And where you can, you know, as you mentioned, it's kind of like that bank account, right? If you keep making deposits in that, you don't know what that's going to happen to somebody else's. You could change somebody else's career, life, whatever that may be. So I think that's all excellent. The last question is, if you could have a conversation with your younger self, totally up to you on what that age is, what would that conversation be? And what advice would you give that person?

Vikas Gupta  40:31

That is a great question. This is not going to answer your question, but it's a prelude to answering your question. You know, you sort of have gotten, I guess, variants of this question, or along the same thread of like, you know, what if this happened, like, what if I got into a different school and I didn't go to UCLA? You know, I had my heart set, like every ex-McKinsey analyst, I had my heart set on Harvard or Stanford, and I didn't get into either. So I went to UCLA. Like, what if I got in? Who knows? Who knows the way my life would have? What if I took this other job instead of Factual? Who knows? But I really like where my life is today. And who knows what that other road would have been? So part of me is like, that time traveling conundrum of like, oh, like, what do I tell myself? And what does that for my life today? Because I like where my life is today. If I change one small thing, does it end up where it is today? Which is a cop out answer. But that's actually the way I like to think about things. I like where my life is today. So whatever happened in the past, it was all getting me here. So I'm not necessarily going to like think too much about what changed it. That being said, to answer your question fairly, in the spirit of like, what advice and to set aside the cop out like investment advice stuff, I think the one thing that I would say is learn to code sooner than I did. The one piece of advice I'd have, at least if you're interested in technology, businesses and software businesses. And if you want to start your own business, being able to hack something together yourself is such an unlock for being able to try something relative to being dependent on I have to hire someone, or I have to find someone or I have to partner with them. Now, there's all sorts of good reasons to have a co-founder. But like just the power it gives you, if truly the business you want to be in is in creating and selling software, the ability to create some of that yourself is this massive unlock. And then I think the credibility and power that that influence, that that gives you within an organization to actually have some level of understanding of how your product works, and what's hard and what's easy. I think that's the advice that I'd give.

Callan Harrington  42:38

I love it because you always hear the other take and I think that's an interesting side, on how you kind of look at it and how that can make it easy or easier. It's never gonna be easy. This was a lot of fun, Vikas. You went into some great things here that, you know, I just appreciate you sharing. So thanks for coming on the show.

Vikas Gupta  42:56

Well, thanks for having me. I really enjoyed it as well.