Episode 54: Gary Beasley ’87 on Taking Calculated Risks
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Transcript:
[MUSIC PLAYING] CASSIE: Welcome to Northwestern Intersections, a Northwestern Network podcast where we talk to alumni about their careers. We'll hear what they've done right, what they've done wrong, and the stories behind both. Today I'm speaking with Gary Beasley. Gary is the CEO of Roofstock, where they're making ownership of investment real estate radically accessible, cost effective, and simple. In the past he has grown small private companies as well as steered large organizations. And he has successfully led two companies through IPOs. Thanks so much for being here with us today, Gary.
GARY BEASLEY: Great to be here, Cassie.
CASSIE: And we're so excited to hear more about what you're up to at Roofstock. But before we get there we'd like to start out where you started, and what was your first job.
GARY BEASLEY: So actually my first job out of college was with us a small computer leasing firm in Southern California. It turns out one of the things I know you wanted to talk about was career missteps. It actually dovetails nicely with this, because it turned out to not be exactly what I was expecting, for various reasons. Yeah, I did not do appropriate diligence, which I guess is a great lesson for folks looking for their first jobs. I got recruited heavily, took this position, moved out to Southern California. And turned out had some real issues with the ethics of the company and the content of the job. Ended up leaving after a few months
And moved back to Chicago and used the Placement Center again at Northwestern, which ended up to be a wonderful resource, and ended up landing my next job, which was at LaSalle Partners in Chicago. And turned out to be a fantastic experience.
CASSIE: Yeah. And that's great. And it seems like that transition really worked out in your favor. That you left for values, reasons of values and ethics. And this next company you worked for really valued that decision from you. And I'm curious if we can go back to that point where you decided to leave that organization, because the first time you and I spoke, you mentioned that this was against some advice you received from mentors. That you should stick around for a while to put your time in or whatever their reasoning may be, but you decided to go with your gut. And can you talk through the challenges of potentially going against trusted mentor's advice here, and some of your mindset around that?
GARY BEASLEY: Yeah, yeah. So I had been advised never leave a job within a year. It could be a bad sign. And so generally that's not bad advice. You want to be around long enough to give something a chance. But I think you also have to have some ethical lines that you either have to cross them and embrace those consequences, or you need to leave and vote with your feet. And I feel strongly that you should leave when faced with that situation.
And I remember calling my dad and talking to him about some of the things that the company was doing, and the way that they were treating customers, and not being truthful, and things like that. And I asked my dad, I said, is this the way business works? It was my first job. And he said, no son, it's not. And I trusted my dad's advice over the rules of thumb. And he said, listen, it may be hard for you to leave, and you're going to need to really explain yourself. But you need to end up in a place that shares your-- for whom the reasons you left will be a positive, not a negative.
And that was an important part of my next career decision is I really want to be in a place where I felt like I could be for a while. And if they had a problem with why I left my last company, I didn't necessarily want to be there.
CASSIE: Yeah, yeah. That's so interesting, thinking to back to that being your first job out of school. You might have thought if you didn't talk to your father, this is how businesses work, and this is how the world of work is. And then the fact that you had this mentor in your father to help you through that, that's great. And thinking at LaSalle, what were some of those major differences that you noticed and picked up on right away?
GARY BEASLEY: Yeah. Well first of all it's just incredibly professional. The people you could just tell were ethical in a lot of the questions they asked, and the importance of treating people with respect, and developing the people who worked at the company, doing the right things for the clients. Basically the importance of building long-term relationships, versus just being a transactional opportunity. And that really resonated with me. The founder of that company, Bill Sanders, built that company to really be the standard of professionalism in real estate. And I like the fact that they were really building long-term client relationships. And you don't do that unless you treat people well.
CASSIE: Absolutely. And your transition into LaSalle was definitely not your last career transition. I know you've done a lot of things since then and in various industries. What was your next transition point to go back to school? Can you walk us through how you approach that being your next thing?
GARY BEASLEY: Sure. So I was pretty sure I wanted to go back and get my MBA when I first started working. And actually I think we talked about this previously, Cassie. The first time I applied to schools I only applied to one school. I applied to Stanford, which was my first choice for business school, and I did not get in. And this will give you an example of how the folks at LaSalle treated their employees.
So my supervisor there, Wade Judge, was also a mentor. He had gone to Stanford and he was disappointed I didn't get in. He called the admissions director, asked, would you mind pulling out his file? Tell me why Gary didn't get in. She did and she said, well, he's a strong candidate, but he didn't really have as much work experience as we'd like to see. And his GMAT scores were good, but they weren't great.
So he pulled me in his office and said, all right, Gary, here's what we're going to do. Do you really want to go to Stanford? You need to work for me for another year. I'm going to let you run two projects start to finish, give you plenty of responsibility. And take a Stanley Kaplan course or something and nail the GMAT. And if you do those things, I think you've got a really good shot. And so that's what I did.
And when I reapplied I got in. And I'm forever grateful to Wade for going out of his way to take an interest in my career and my growth personally. And we've stayed in touch since.
CASSIE: Yeah, that's so great that you had someone who could help you both provide you the opportunities, and the insights to what were these folks at Stanford thinking that you needed. What was that missing factor, and going back to get those things. And thinking about some of the recent alumni we have out there, and people who may be applying to schools, did you ever think that this was a risky move? Or did you ever feel any pressure in applying only to one school and applying again the second time?
GARY BEASLEY: Yeah. Well I would say the first time I applied I only applied to one school, and I was fully prepared to work another year if I did not get in. The second time I applied I applied to multiple schools. So I was prepared to go then. Had I not gotten into Stanford, I had a couple of other schools I was really excited about as well, including Northwestern.
But I did want to personally have a different experience. I wanted to see a different part of the country. And had I not gone to Northwestern undergrad, Kellogg probably would have been my first choice, because it's such a fabulous business school. But I wanted to experience a different part of the country, and ended up falling in love with the west coast, and been out here since.
CASSIE: Yeah, yeah, definitely. And it sounds like that was a location that you grew attached to and then later wanted to settle down in after making a few more career changes. And so speaking to folks who are considering grad school, finishing grad school, what was your next move after that? And can you talk through the strategy behind your first role after school?
GARY BEASLEY: Sure. So coming out of school, back when I came out, a lot of folks were taking jobs in management consulting, investment banking, to a lesser degree private equity. I ended up taking a position with a small real estate investment firm based in Santa Fe, New Mexico, which happened to be a company called Security Capital. Happened to be founded by the founder of LaSalle Partners. So I started my career at LaSalle, Bill left LaSalle, started his own firm in Santa Fe, which is where he had a very large ranch.
And he came to speak at Stanford. We went out to dinner afterwards, and after the dinner he basically offered me a job and said, hey, why don't you come work for me? Help me get this company going. You could carry my briefcase. You'll learn a lot. I can't pay you much because I'm just getting this thing going. And I ended up being very intrigued by the opportunity to have a mentor like that who had seen so much and been so successful over his career.
And it was it was a low salary, it was less than half of other offers that I had coming out of school. But at the end of the day, I probably would have or should have been willing to pay him for that experience, which he was fully aware of, I think, which is why he offered me so little money. But it ended up turning out to be a really, really great opportunity. I learned a ton, and both worked for him and then worked for another senior person there learning kind of the ground up development business.
And then it's funny how life works. So I ended up getting a call from a prior boss at LaSalle who knew of a great job in the Palm Springs area, in La Quinta, working for a KKR sponsored operating company that was buying resorts. And they were basically looking for a young MBA type who would be willing to move to the desert and help them grow that business. And again, would come in without making a ton of cash, but if you proved yourself, could get a meaningful amount of equity.
And so again, I took that job because it seemed like a really interesting and smart group of people who had a very clear strategy, was well capitalized, and being willing to bet on myself that if I did a good job it would lead to real compensation and real equity. But again, early in my career I felt like taking jobs for experience was much, much more important than taking them for the money. And I firmly believe that to have paid off for me.
And I ended up being in that role for about six years working for KSL Resorts. And I ended up running the acquisitions group there. And a lot of my friends think that was the best job that I ever had. And I was flying around the country buying resort properties. And it really was a fantastic job and role and a great group of people. And again, it was a place where they treated people really well, had great ethics and great client relationships. And I just really thrived there. And so again I was able to witness-- it was a pretty small company when I got there, and witnessed that company grow. And it did get me excited about ultimately perhaps building something myself. Although at that point in my career, I was not ready to do it. But I learned a lot about how to set up and grow a company from my years at KSL.
CASSIE: Yeah, yeah. No, that's great. And I love the concept you talked about with taking a job for the experience rather than the money. And in reality, back when you were finishing your MBA, was that hard for you to not take some of those offers where you were getting offered more when your peers were taking some of those roles? And what was your mindset there? Because I'm sure we'll have people-- folks listening in-- curious about those moments for you personally.
GARY BEASLEY: It was actually quite hard. As I think back on it, I had a lot of student loan debt. I was a Pell Grant kind of kid so, my parents did not really have much money at all. So I was able to get into school, and I maxed out the loans and work study, and ended up graduating with quite a bit of debt. So it was not lost on me that that embarking on this path was a little bit more risky than taking a banking or consulting job that would allow me to pay off my loans quicker and with more certainty. So it was a little bit more challenging the first couple of years.
And I do remember when I was at KSL, getting my first real bonus and being able to pay off my loans was an incredible feeling. And at that point it really made me feel like I'd made the right decision. And even though I took a bit of risk, I think, by taking a little bit more of a path that I felt was going to be in my long-term best interests. And it ended up working out.
CASSIE: Yeah, yeah, I can't imagine how emotional that must have in being able to pay off the loans. I'm sure there are lots of our listeners who can really resonate with. So I'm curious what you learned, because I know you had some more career transitions after that. What did you learn from those two roles being a part of something early on that has played into your success at Roofstock?
GARY BEASLEY: Yeah, so I think you learn a lot from every position. I think as long as you're open to it. One thing that I've tried to do is learn, for example, from the various CEOs I've worked for. I've had the benefit of working for some really, really interesting people and some very good CEOs, and being able to take from that what has worked well for them. And not everyone's work style is the same. And be able to amalgamate all that into what works for you as a work style.
And so I think one of the things I learned from Mike Shannon KSL was that he was really, really good at going from 30,000 feet all the way down into the weeds. And being able to go up and down. And that I think is a unique skill. And something that I-- because I am fairly analytical, and I started off as a financial analyst, and then I've had plenty of jobs where I really got in the weeds-- now that I've been CEO of a few businesses, I really feel like I can have a high level conversation but then continue drilling down into the details.
So I think letting people know that you're not only interested in what they're doing, but you could actually perhaps be helpful when you need to drill down and help people solve problems. Because at the end of the day, I think that's what CEOs are there for. So you're setting the vision for the company, but you're the captain of a team. And I think a lot times being a player coach can be really helpful. And so several of the CEOs I've worked for have been really effective player coaches. And so that's one of the things I've tried to emulate over the years.
CASSIE: Yeah, I really like that analogy. And I'm sure that's a really challenging skill to develop, to be able to do more macro level thinking, and then also micro level thinking quickly. And did you see this play out in your first role as CEO? And can you tell us a little bit more about those early experiences in some of your early leadership roles?
GARY BEASLEY: Yeah. So I remember-- it wasn't my first CEO role-- but I was just doing my career progression. So after I left KSL I went to a company called Zip Realty as CFO. And it was an early stage company that was one of the first online residential brokerages using the internet to basically bring down costs and increase transparency. So I went from being someone who's doing a more pure investment and business development to being the CFO of a tech startup. And it was an interesting challenge for me.
I ended up being there for five years. And over that period of time, not only did we grow the company and took it public-- that was my first IPO. I took it public as CFO. That was quite a great experience.
But then when the CEO left for a couple of earnings calls, I was both the CFO and the acting CEO of a public company. So that was a really interesting life experience. And I was officially president of the company, and then acting CEO. And I remember one of my board members, Don Wood, at the time said, Gary, this is going to change your career, going from being a CFO to being a president. Because having that sort of operating responsibility, once you get to that level, you really can grow from there and either be president or CEOs of other organizations.
And he was really right. From that point on, that was my last CFO role. Everything that I effectively have done since was more as a CEO type role. So that was a turning point for me. It's funny, because until you're a CEO, no one thinks you can be one. And then once you are, then everyone is convinced that you can. And it's same thing with a CFO. Once you're taking a company public, people want you to do it again. So getting that first box checked at a new level is oftentimes really, really hard. And then once you've done it, you've been validated. And so having done that, I've been able to now do it a few times in some different companies, and have continued to grow in various aspects with each of the ones that I've done.
CASSIE: Yeah, yeah. And thinking about the CFO to CEO experience and transition, what were some of the biggest things that surprised you about that next level?
GARY BEASLEY: Yeah, it's funny. I remember thinking when we took Zip Realty public, and I was the CFO, I felt like I was doing all the work and the CEO was getting all the glory. I think a typical CFO would lament and say, yeah, god, I went to all the drafting sessions, I'm doing all the work. The CEO's just taking all the credit.
So the next time I took a company public I was CEO, and I realized it's actually a lot harder than it looks from the outside, because the buck stops with you. It's one thing to talk about the numbers as the CFO, it's another thing to deliver the numbers as the CEO. And so it's a whole other level of responsibility and pressure. And one CEO that I worked for used to say-- they always say it's lonely at the top. But actually it can be. But at the end of the day, the higher up in the organization you are, the less you actually need to do, ironically.
There are plenty of CEOs who don't do much. You could be a figure head CEO, or you could be a very active one. If you have a really great organization, as the CEO you shouldn't have to be making a ton of decisions. So it's a little bit ironic that the further up you go, the less you actually have to do. But what you do is so important and so critical. And oftentimes determines the success or failure of the organization. So it creates an incredible amount of responsibility and pressure.
And you have to be, I think, really-- know your weaknesses, be willing to engage, help when you need it, have a team around you who you trust and are vulnerable with. There's a whole host of things that we could talk about as what can make a CEO good or not good. But it's funny, I have learned over the years that as you go up, the responsibility changes, and that whole level of pressure changes. And I would say it even goes to the next level when you become a founder and it's your own company.
So it's one thing to run a company that someone else started, might have been around well before you, and hopefully be around well after you. It's a whole other thing, which perhaps we'll talk about a bit, of leaving something and starting something from scratch, and hiring every individual, having it be your idea. Bring in all the investors, hire every single person. That's a whole other level of pressure and responsibility.
CASSIE: Definitely, definitely. And so can you walk us through the next few roles that led you to where you are today at Roofstock?
GARY BEASLEY: Sure. So after we took Zip public, and I was there for another couple of years, I ended up deciding to take a year off. I left in 2007, early 2007. I taught a class at Stanford Business School, and really started to think about what I wanted to do next. I ended up doing a little bit of work in the solar business for a while, which I was very fascinated with. Wanted to end up trying my hand at private equity. And so I ended up going to work for a family office and doing some investing. Specifically in the hospitality sector which I had some experience in.
And this is, again, where it's interesting, where having a non-linear career path can be useful, since I've had operating roles and investing roles. I was working for Geolo Capital, which is John Pritzker's family office. And one of my first deals was to acquire a controlling interest in Joie de Vivre Hotels, which was at the time the second largest boutique hotel platform in the country. And Chip Conley-- who many people may know is a really successful entrepreneur-- and so Chip was the founder and CEO of that business.
As we were getting close to closing that transaction, Chip and John Pritzker came to me and said, hey, we've decided that we want you to step and be CEO for the next year or so. And Chip and John became co-chairman. And so rather than just being an investor, I went back into an operating role, and transitioned it from a founder led company-- which it was for many, many years under Chip-- to more of an independent sort of mindset. So I ended up doing that. And had I not had those operating roles in the past, that opportunity wouldn't have been presented to me.
But I got then some experience of being an investor, but also leveraging those operating skills. And so I ended up being there. We ended up merging Joie de Vivre with another hotel company called Thompson Hotels. And now several transactions have happened since, and it's all part of Hyatt. It's all got merged in recently. So good outcome for everybody.
And so it ended up in 2011 a couple of friends were buying homes during the real estate downturn, and I was an investor with them. They ended up coming to me and offering or suggesting that perhaps I come join them and build a business, to build an investment platform in housing. To take advantage of the downturn. So they really thought about did I want to continue to do the hospitality investing, or move on and actually join this early stage investment platform with my friends. And I decided to dive in and do it. And it seemed like a very interesting part of the cycle to do it.
And one of the things that I guess we had talked about before, bits of advice. And one of them was think about where you are in the market cycle. And if you could do something where the tide is rising, there is a much better chance that you're going to have a successful business. And so I felt like joining a platform and buying houses that had dropped in some cases 50% or 60%, figuring out how to rent them out profitably. And starting to attract institutional capital to what's the largest asset class in the United States, which is US housing. If we could figure that out, the best case would be we actually built a platform that had real value. The worst case is we're buying a bunch of cheap houses that someday will be worth more. So the downside was it was a good trade. The upside was we could actually build a company around it.
And so I ended up leaving to go do that. And it turned out that the upside case happened. And not only was it a good trade, but we actually, through the application of technology and some innovative business practices, actually built a company in that space. We were early investors and advocates for bringing institutional capital into single family rental housing. And we ended up forming a public company. Then we took it public in partnership with Starwood Capital. In 2014 formed and took public a REIT called Starwood Waypoint Residential Trust. It's now part of Invitation Homes, which is the largest single family rental platform out there.
CASSIE: Wow. And so this is so interesting hearing through how you eventually started this organization. You said the risk was that it was a good trade. The upside was that you would have this awesome company and be able to move forward with that. I know you also mentioned to me early on that you're out there on the west coast founding a tech startup, and you're a little bit older than some of the other startup founders in the area.
GARY BEASLEY: Thanks for reminding me of that.
CASSIE: What are what are some of the aspects that are different for you? Because you're more experienced, I should say.
GARY BEASLEY: Thank you. I much prefer that characterization. I would say it's interesting because yeah, our company Roofstock was recently named one of the Forbes 50 fintech startups. And so I think I'd mentioned to you that there were six real estate platforms, and I was the oldest founder by probably 15 years maybe, or even more.
But what I found was in starting the company, because I guess as you say, the flip side or the advantage of being older is you have more experience. And so I was able to have, I think, really productive conversations with investors around-- having run businesses before-- be the type of entrepreneur where if this business works, could actually be here for a while and take it through many stages. And not necessarily be a 24-year-old startup founder who, after the series B, needs to get replaced by some grown ups. That's not always the case, but oftentimes is.
Had deep industry relationships, because I was running a public company. And had a lot of conviction around my idea. And I think if you've got experience, understand the dynamics of a particular market intimately, have relationships that can help get you started, and it's a big market, all those things-- at least for us at Roofstock-- led to a pretty attractive opportunity, I think, to bring in capital. And my co-founders also had quite a bit of experience. And so I think it's one thing to have a good idea. There's a lot of good ideas. It's another thing to have a good idea and have enough of a track record and team around you who have experience and the capability to really execute on it.
CASSIE: Yeah, yeah, absolutely. And thinking about some of these influential people in your life, the co-founders, mentors, folks from various communities, how has the Northwestern Network more broadly impacted your career?
GARY BEASLEY: Yeah, so the Northwestern Network has been fantastic for me. As I mentioned, got me on the right track career-wese when I came back, and was able to use the Placement Center, which was super helpful. Stayed in touch with several professors over the years, which has been super helpful, even in terms of getting recommendations for grants [INAUDIBLE] and things like that. That was fantastic. It always seems that as I'm looking at companies or coming across ideas, there's people in my network-- my Northwestern Network-- who are dialed in. It's just been a fantastic resource for me over the years. And there's just something about sharing that common bond that it's just a lot easier to reach out to someone if you have that shared experience.
And I know I try to be helpful to Northwestern, either alums or students who reach out to me, because I have appreciated how people in my past have been generous with their time and been helpful. I mentioned Wade at LaSalle Partners. When I have an opportunity, if I could spend 30 minutes with someone and perhaps be helpful, and making a few phone calls, or providing some insights, I'm happy to do it. Because without people taking that time and helping me, I would have been on probably a different track. And I find that very satisfying.
CASSIE: Yeah, definitely. And thinking about the things that you were able to accomplish throughout your career and your journey, it's so interesting to hear the various transition points. What are some of the things that you're personally most proud of?
GARY BEASLEY: Yeah, so you know I think one thing that I'm proud of is I don't think that there's ever been-- I can say with certainty-- that I've never left a company on bad terms. Like not burning bridges, I think-- as people say, don't burn bridges. Actually, it's amazing how small the world is. And one of the things that I do myself when I'm looking to hire somebody, we do deep diligence we find out where people have worked. And people remember how you arrive at a company and how you leave. So I think I'm proud that pretty much everywhere I've worked I have tried to do as good a job as I can and leave on very good terms. And so that's something I'm proud of.
And proud of that I've been at a couple of companies I've been able to take public, which is-- early in my career I was hoping I could be part of one IPO. And I've been able to be part of a couple, which I'm really fortunate to have done that. And I think I'm extremely proud of having started Roofstock and gotten it to the stage where we are today, almost four years into it.
And one of the things that I never knew was whether I could do it. It's one thing to join a company that's early. I joined Waypoint Homes early with my partners there. I joined Zip Realty fairly early. But both of those were already going. And with Roofstock, I left running a public company, a fairly comfortable position. And I could have stayed there for some time, and gave that up to start from scratch and see if I could build something. I was confident that I could do it, but still realistic about how difficult it is to start a company, and then go from, as Peter Thiel would say, from zero to one. Going from zero to one is very hard.
And so that I would say [INAUDIBLE]. And I guess why it's so hard is so many things have to go right. You have to have a good idea, you have to hire the right people, you have to attract capital, you have to attract customers, you have to build the right culture. All these things have to happen. And if any one of those things doesn't happen, these things oftentimes get off the rails and only go so far. And so that I'm very proud of.
CASSIE: Yeah, yeah, definitely. That's great. And I know that we did talk a few minutes ago, a little while ago, about some of the missteps, if you will, or challenges throughout your career. But have there been any other challenges that have left a lasting impact on you that you might want to mention today?
GARY BEASLEY: Well, I would say obviously the first one was that was the most difficult, taking a job that ended up not working out right out of college. I think it's always difficult to know when it's time to leave something and do something else. And I feel like each time that I've left it's-- actually, I've been fortunate to have had things to work out reasonably well. You never really know. You never really know.
And so I guess what I would say is you have to be willing to bet on yourself and be willing to take calculated risks if you want to advance and go to the next level. And I think everyone has to think about their own personality and their own personal goals. And I think I've been fortunate that a lot of these calculated bets that I've made have worked out reasonably well. Who knows? Had I not made them it might have worked out better. But there's no way to rewind the clock.
But I think because of my early experience where I was sort of snake bitten by that first bad decision that I've been very, very careful when I've made these other choices. So in a way it's a little bit like getting inoculated. It was my inoculation early on to making a rash career decision. So in a way it was a little bit of a blessing, I think, in disguise. That when I've made some of these moves, which to the outside might look pretty bold-- leaving a public company job to start something, or some of the other moves that I've made-- to me they made a lot of logical sense.
And I always thought about, so OK, well, what's the worst thing that can happen if this doesn't work out? And the worst thing that could happen is, well, it didn't work out. I'm sure I'm going to learn some stuff from it. And I'm going to go back, and I could get another job [? for it. ?]
So I think a lot of times people maybe don't really think about-- and actually think about-- what happens if things don't work. And is it the end of the world? And oftentimes it's not. And I think sometimes people might be a little bit too concerned about how something might look on their resume. And it's one of the things that I really liked about Stanford and being in Silicon Valley is failure is, to a degree, celebrated. As opposed to, wow, that guy was in a business that didn't work.
And so it's very liberating. So I really did feel like if Roofstock didn't work, it's not the end of the world. It's OK. And then you learn from those reasons it didn't work and use that for your next thing.
CASSIE: Yeah, absolutely. So many alumni will come to the Alumni Association asking about those career transitions, and when is the right time, and for resources and making those decisions. And I just love that advice that you gave. Bet on yourself and take calculated risks, because there really isn't a right or wrong way or a perfect time ever. So it's just a matter of when is right for you. So that's great.
And as we've been talking, Gary, there have been aspects of your identity that have come through. How have your identities impacted your career?
GARY BEASLEY: Yeah. So what I've realized about myself is I really like the building aspect of companies as opposed to maintaining them. And so I'm uncomfortable with that ambiguity that comes with having a blank piece of paper, or a business model that needs to be created or refined rather than just maintaining companies that have been stabilized. And I think we have to ask ourselves kind of what type of person are. We are we a builder, or are we more comfortable with running something and optimizing something that's already there?
I think this kind of soul searching for me when I was running the public company, is this what I want to do? Or do I want to create something? And I've described it before that what we do in building a startup is much more like jazz than sheet music. Sheet music is you have your playbook. And running a public company is very much sheet music. And you go quarter to quarter, and you have your plan.
When you're running a startup, every day, literally things happen that you have to react to. And so again, much more like jazz. And so I am comfortable with that sort of level of ambiguity and building the teams and making quick decisions and trying to do all that. I enjoy it very much. So again, there's no right or wrong.
But I think as individuals you figure out what pushes your buttons and where you might be most effective. And I think at the end of the day I felt like there's probably other folks who could run a public company or my public company just as well or better than me. But I felt like I had a unique combination of skills and experience to where starting this business, there weren't as many folks who could actually have a reasonable shot at building a marketplace in a space like I could.
CASSIE: Yeah, no, that's really interesting. And figuring out that that's the pieces of something that you enjoy is building up and being a little bit more agile. And that's really interesting. And Gary, thinking about some of these mentors and folks in your networks, have you received any advice from any of those people that's really stuck with you throughout?
GARY BEASLEY: Yeah. I think we did talked about this earlier, but this advice of earlier in your career not taking the job for money but doing it for experience I think with such wise advice. And I did it with my first couple positions. It's definitely paid it paid off. And this idea of being willing to bet on yourself and not necessarily ask for everything upfront. So I come across people, even today, who we're looking to hire, who really try to sweep out the corners and maximize everything as part of their offer.
And I'm always a little bit cautious about that, because if people are really confident in their own abilities, they should not be, in my view, super worried about that. Because in fact, with some of the folks who we've hired who very quickly realize that they are so good, and we give them more stock and we raise their salary because we want to keep them because they're good. So I guess just being willing to have the confidence to bet on yourself. And not necessarily not get a position because you negotiated so hard for all of your upfront compensation.
To me it's much more important to join the right company and the right people. And if you can do that and you're good, the outcome is likely to be much better than just optimizing for your upfront compensation. And that was some advice that I got earlier in my career. And really believe that it has served me well, and I think is advice that people should really consider.
CASSIE: Yeah, no, that's great. And it's been really fun, Gary, talking with you about your career journey, and all the twists and turns, and the winding through different roles and different aspects. And I'd love to ask you if you have any other advice that you want to leave the Northwestern Network with today?
GARY BEASLEY: Yeah. I guess I would say work for people you respect and can learn from. Really at any point in your career, but early on for sure. But I think always that's a really important point. I think thinking about ideally if you could work in an area you have some passion for, some interest in, I think that is awesome. You can't always do that.
But for example, when I worked at KSL, I love to golf and I love the idea of working in the resort industry. I worked as hard in that job as I had anywhere in my career. But I was working in an area that I really had a passion for. And I think that's super interesting and helpful if you can combine your vocation and avocation.
I would say don't be afraid of a non-linear career track. Mine has been pretty non-linear, but when you think about the skills that you build and the kind of portfolio of experiences, all of that helps inform who you are later in your career in, and you draw upon that. I think that reservoir of experience is super helpful. And I would encourage people if you've got the entrepreneurial itch, don't be afraid to scratch it. I couldn't be happier having started Roofstock, and have learned so much and had so much fun. Again, I've worked harder doing this than probably anything I have done.
But it's a whole different level of stress. It's much more of an excitement, more like a sports type stress getting excited for the game. And if things don't work out it's like, all right, we lost today. How are we going to win tomorrow type thing. It's not the external stress that can come from being in a place where exhaustion factors influence you so much. So at the end of the day if you start a business and it doesn't work, you can always go back and get another job or start another company. But if you don't dive in you never have that opportunity to see if you could do it.
CASSIE: Yeah, yeah. Gary, this is great and so helpful. Thank you so much for sharing all of these really great insights and pieces of advice, and being so honest about your career journey. It's really great to feature that non-linear career path and the way that you have found such great success through each of those different roles. So Gary, thank you again for being here with us today.
GARY BEASLEY: My pleasure, Cassie. Enjoyed it.
CASSIE: Thank you for tuning in to today's episode of Northwestern Intersections. To find more information about the podcast, please visit northwestern.edu/intersections. That is northwestern.edu/intersections. Have a great rest of your day, and go cats.