#4: Chris Hsu, Azibo

Welcome to From Startup to Grown up, the podcast. My name is Alyssa Cohn. I'm an executive coach, an angel investor, and the author of From Startup to Grown Up. Each week I talk to founders, creators, advisors, investors and builders of all kinds about their insights and experiences in going from startup to grownup. This is episode number four and I'm thrilled to have Chris Hsu of Azeebo. Azeebo is the free one stop shop for rental property finances. I was introduced to Chris by Andre Axelrod. Thank you so much, Andre. Chris has an incredible background, from west point to McKinsey to KKR to HP. He's also an independent board director and he was an advisory partner at Andreessen Horowitz. Today in our conversation, we talk about Ranger school, his experiences there, what he wrote in his first culture document, how he met his co founders, what the first few months of building a startup are really like, and the day his wife went on strike. We also chat about the concept of the leadership selfie and how he handled all the rejection that he got when starting up a Zibo. Now, one note in the interview, we talk about Zeebo. But since then, in the fast paced startup game, Chris's company rebranded to Azeebo and launched new features. So check them out. Please enjoy this conversation with Chris Hsu.

Chris, welcome to the show. I'm so excited to have you.

Thank you, Alyssa. It's great to be here.

Thrilling. We were introduced by Andre Axelrod and he's the founder of Smartling and most recently the CTO of People AI. Now, Andrej told me to ask you about cursing, so I'm going right there. Tell us about the joy of cursing.

Well, now I'm embarrassed. That was actually a. A big doozy of a question. Well, my, my. I have three daughters, ages 7 to 16, and they call me sometimes Daddy, bleep, bleep. And I would say, I would say that I grew up in Louisiana, Chinese, Irish, Cajun, so maybe a little bit came from there. And then I spent 10 years between the military academy and the army learning and perfecting my trade. And I've tried many, many, many ways to modify that. But I'm just who I am, and I've let it all out and I say what I want to say, when I want to say it. And God bless America, I love it.

He's here for freedom of speech. Well, actually, Ben Horowitz is also a proponent of swearing in the workplace. He's like, if you don't like it, this is probably not the right company for You. That's what he said publicly.

I'm a big fan of his.

Yeah, that's great. In any case, Chris, as I understand it, your father emigrated to the US From China, and he lived through the Japanese occupation of China. He lived through the Communist revolution. He spent his young adulthood in a refugee camp. He then borrowed $500 and to a container ship to come to the U.S. is that accurate?

It's pretty much all accurate. The only thing is that there was really no refugee camps. They just were refugees. Meaning you. They kind of wandered from 1945 to 1949 all over Southern China. And then when the Nationalist army lost the Communist Chinese, they then all just got on boats and fled to Taiwan. And that was the genesis of Taiwan and spent a number of years, you know, Taiwan went from, I don't know, a couple hundred thousand people fishing island to millions and millions of refugee Chinese and just had to build what it is today, which is pretty remarkable. And then his dream was always come to the United States, but he couldn't afford it, so he borrowed money from a friend of the family and couldn't afford a plane ticket. So he got on a boat, went through the Panama Canal, ended up in South Carolina. And he had two scholarships, one to Syracuse and one to Kansas State University. And he asked the person at the port, which one's closer? And they said Kansas State. And he's like, that's where I'm going.

And I have to assume that that, you know, sort of affected your. The way you thought about life growing up, you know, could you share how that kind of imprinted your life?

Well, you know, it's funny thing is, we didn't really know a lot about that until we became more adults. And when my first daughter was born, I sat her on my dad's lap and said, dad, you know, your grandchildren, that one, and all the ones that follow are not going to know anything about you or your journey. And I'd been asking him for many years to write down a manuscript around, you know, what he went through, because we knew bits and pieces, but we didn't know the full story. And then he agreed to do it. And it took, like, three more grandchildren before he finished it.

Wow.

But we hired him an editor to help him, you know, kind of put together, because it's hard to write a book about yourself. And, you know, he wrote a book about. It's called Faith and Family. And really the theme of it is he just talks about being lucky and how at every stage of his life, somebody helped him and he wouldn't be alive or in the United States if he just didn't have people that helped him. And, you know, for me, I'm inspired by him because he's 92 years old, still alive, and he's the happiest human being on Earth. And he's lived through hell, he's lived through famine, he's lived through occupation, war, being a refugee, you know, embarking on. He was the first person in his family to come to the United States. You know, it's just kind of a crazy thing. And I always think about, like, if I risk something and fail, it can't be worse than going back to what my dad grew up in.

Yeah, I can imagine that's a real point of inspiration for you. And then I understand that he was really one of the factors that. That really encouraged you to go to West Point and that's how you maybe got to West Point. Could you tell us that story?

Yeah. I mean, we grew up always with a sense that freedom wasn't free and that we had to do our duty to ensure that it remained free. And, you know, I think a lot of people in today's day and age just forget that, you know, what we enjoy in the United States as far as security and the functioning of most of our society, despite all the social unrest, it's still a remarkably well functioning society. And people from all over the world want to be part of that. And it's not free. And a lot of people have suffered, died, and in order for that to, number one, be founded, but then to be defended over time. And so we just grew up with that view that you just had a commitment and responsibility to serve. And my brother and I both went to West Point and I mean, we were fortunate enough to be admitted, but it was just a natural extension of what we thought our responsibility in the United States was is, you know, my dad and my family was all afforded a completely different lifestyle than the family that he left behind in mainland China. And, you know, we just were so grateful for that that we thought that we needed to give back.

So then you found your way to West Point, and after that, if I'm not mistaken, you went to Ranger school, Is that right?

Yeah, I did. I did that really on a dare, but from some of my friends who said, there's no way you could do.

It, so it got your competitive juices flowing. So that was pretty intense. Right. So if you tell us about Ranger School and are there any takeaways you have today? Because we talked about this a little Bit earlier when I get into this. The journey of entrepreneurship is kind of hard, in case you haven't noticed. But Ranger school also sounds pretty hard. How did you. What was the experience like, and how did you get through it?

There's a lot of parallels. I mean, I remember Ranger school is about three months if you go straight through, but a lot of most people don't go straight through. I think only about 10 to 20% of the people, at least when I was there, go from starting to end. There's four different phases, and, you know, if you don't pass a phase, you go and recycle it twice. So some people spend, like, up to a year trying to get through Ranger school. I was fortunate that I got through straight through, and I honestly, I wrote on the backs of some. Some of my classmates from West Point in the last phase of it, because it's just so hard.

Yeah.

But what's up, Jack?

Can you tell us a little about Ranger school? Just people who don't know about it. Like, what is it and what's hard about it.

Yeah. So Rangers is an elite. I know everybody listens to the Navy seals, and I'm not a. You know, I'm not a Navy fan. I'm an army fan. But really, Special Forces, US Special Forces, the Delta Force, and the Army Rangers are really kind of the core of special operations and had been for a long, long time. And Rangers are really the conventional force that typically drops behind enemy lines, secures an airfield, cuts off enemy supply lines, disrupts such that the conventional forces can land and do whatever they need to do, whatever the mission is. But it's really a very elite group of people. You know, to become a Ranger, you go to Ranger school. To become a certified Ranger, it's a leadership course, a survival course, and a tactics course all in one. And, you know, for me, I was a. I was a tank officer, so I was in heavy M1A1, Abrams tanks, and we had to all compete to get a slot to go to Ranger school because Ranger school was really. It was really reserved for special ops and infantry and airborne and all that stuff. And you. I got one of the slots, and so I went. And it was probably the most challenging physical, mental thing that I've ever done. I mean, my body had broken down. I lost 35 pounds, and in the time frame, I might just look like bones all over my face. I couldn't hold my bowels by the end because my body just wasn't functioning. I couldn't take my boots off because my Feet were swollen and you don't sleep. You're doing tactical operations in. In the mountains, in the swamps, in the desert, and it's just really grueling, and you're carrying £100 of equipment and. And you're in a tactical operation where you're being attacked and you're attacking and doing all this stuff. And it's just really meant to be one of the most challenging courses that you could go through. And I remember, you know, what's parallel to being an entrepreneur is I was so hungry at one point in time. Then in the middle of the night, I started chasing a Burger King Whopper through the air because I thought I saw a Whopper with cheese flying through the air.

Hallucinating Whoppers. Wow.

And it's almost like chasing capital. Sometimes you don't have enough capital to grow or to survive. Wake up at night thinking about a million dollars in your bank.

But, like, if you think about what you had to do, how did you get yourself through that mentally? That sounds so intense. Even more intense than I realized. How did you get through that mentally? And what do you still use today in your life as an entrepreneur?

I mean, it's interesting. You know, I learned about, like, my. I learned the actual physical, mental, and emotional limits of Chris Shu during Ranger school. And I remember walking in the mountains on a ridgeline in the middle of the night, dropping my weapon, which is like a. Like a mortal sin in the military. But I had tied it to myself. We called it dummy cords. You literally tied everything to your body because if you drop something or fell asleep, you know, and the reason I dropped the weapon is I fell asleep while walking and dropped the weapon. It got caught in a bush and it woke me up. And you just. You learn that you just put one foot in front of the other, number one. It's one step at a time. It's one day at a time. It's one mission at a time. And then you have to rely on your team. You mean as a leader, you get evaluated on leadership. So you get these missions and you will be a leader. And then the next mission, you'll be the machine gun or carrying super heavy machine gun, working for another leader. And so if you're a jerk to them and screw them over, guess what goes around, comes around, and you learn the power of just putting one foot in front of the other. And then more importantly, it's all about team. I mean, I remember I got to the last phase of Ranger school and I had nothing left in my tank. And I show up and my buddy from my company at West Point, it failed the previous swamps tour and he was in our class and he showed up and he had been fat because he spent three weeks eating and his cheeks were big and his name was Pete Carrey. I love that guy. And I swear he carried me through ranger school, that last phase, because I could barely walk. And you just rely on your team and I think that's when you got nothing left. You gotta rely on that team.

Yeah. Yep. That is so powerful. And I can see also this like an interdependence. Right. It's sort of like, you know, when you rely on your team and sometimes you're the one that can carry people through and sometimes they're the one that carries you through. And so having that tight knit point of view, I think that's what's important also.

100%.

Yeah. Wow. So after West Point, after Ranger school, after you served in the army, you learned about real. And you learned about real estate investing through a radio show. And then you dipped your toe in, you became a real estate investor. Why not? And so how did you go from there to founding Zeba? What's the founding story of Zeba?

Oh, man, that's a, that's a crazy one. Well, it is funny. I have to tell you, now that we're actually recording a podcast, I was telling some of my team this story about how I got into it and you know, how I listened to this show and you know these guys that had made a bunch of money as real estate investors. I was poor as anything when I got out of the army. I'm like, man, I got to find a way to like, provide for my family. And. And they're like, oh, man, what, what podcast was that? And I'm like, dude, that was before podcasts, man. That was even almost before the Internet. AM radio. Like what's that? AM radio just goes to show you. Like, this is. I always tell people being an entrepreneur is a young person's game. Yeah, there's definitely a generational gap here.

Yeah, yeah, I totally get that. But so what happened? So you became a real estate investor and then what happened?

So look, I, you know, I basically had been a real estate investor for 21 years and you know, I love real estate as a hobby. And at one point in time I thought that, oh, well, that's, that's really what I'm going to do on the side and that's going to end up being. And then my career took off and I didn't have Time for it. So then my wife actually started taking on a lot of the responsibilities. And then one day when I was the chief operating officer at HP&I, I didn't have any time to deal with anything outside of work. My wife came into my office and she's like, I quit. I'm like, what do you mean you quit? She's like, I'm not going to be your property manager anymore. And I said, what do you mean? I said, you're the best, most efficient property manager in the world. And she said, that's because you don't pay me squat.

She went on strike.

She quit.

I love it.

So for 21 years, I've lived every pain point of owning rental property. And you know, I was an advisory partner helping Andreessen Horowitz companies in people. AI Andre was one of them. And I got a chance to help coach Andre and you know, really helping him think about how to position the company, build it, go to market, and you know, the discipline around that. And I met these guys who had this idea to start a financial services platform focused on independent landlords. And you know, I, I thought to myself, and actually it took one of the these people to say, hey, you'd be the perfect fit for this. Because my hobby was being an independent landlord. I had spent many years in financial services at KKR and McKinsey and HP and in the last probably decade of my career I had been in tech and software. And I was like, wow. Oh, you're right. It's like the intersection of my hobby with an industry that I'm fascinated by, with building software in a modern cloud native environment. So the idea of being able to create the one stop shop financial services platform for the 8 million landlords in the United States and property owners and short term rental owners who own real estate and are just trying to make it work and having lived through all the pain that they have, I mean, I have Airbnb properties and long term rentals and have done everything from apartment buildings to duplexes to single family homes. Like, being able to put all that together in a modern cloud native software stack with an integrated financial services marketplace was super exciting. And I just said, look, that's what I want to do. That's what I want to go Bill.

And your co founders, I think, sorry, Gregor Watson and Rob Blomker. Right.

That's right. Serial real estate entrepreneurs.

Yeah.

Who built multiple companies in and around the space. Lending companies, hedge funds that buy mortgages, roof stock where you could buy fractional or whole rental properties. Online. I mean, just a really remarkable set of guys.

Yeah, so they, you, you met and they came to you and they talked to you about their idea and you said it was magic. It was a magic, magical sort of co founding team. Tell me what the magic was like and tell me how well you got to know those guys before you decided. Sure, I'm in. I'm going to co found with you because co founding is like a, we're going to get to your marriage a little bit later. But co founding is like its own marriage. And so I'm just curious how much did you guys sort of talk through the strategy and your values and kind of what you were about before you just jumped in together?

Yeah, look, I think, you know, it is, it's really. Co founding company is really hard. I would say number one, first and foremost was I just really liked the idea and I just thought that there was a massive opportunity and all of us brought a little bit something different to the table. And I think that was one, I would say two. Both of them had just a remarkable reputation in the industry. And I think that really helps a company with fundraising with, you know, the getting the door opened and hiring a team, which is one of the hardest things you have to do as a, as a startup entrepreneur when you're starting from nothing. And I mean, I will tell you that's probably the most humbling aspect of it. And then just getting aligned around, you know, before I ever even agreed to, to to build this together with them, I wrote down on an airplane flight the culture of the company I wanted to build. And you know, that was cathartic in and of itself because there was nothing, there was no company, there was no people, There was just like, okay, well look, if you're going to get aligned around something, you know, the strategy may change, the products may change, people may change. But the end of the day, the thing that's gotta be, you know, rock solid is the culture that you want to build and you know, how you want to build it. And, and that's really what we spent a lot of time talking about. And getting aligned around was like, what is the culture of the company that we want to build? And we co developed like I wrote a strawman and then, you know, the guys put stuff in and we've, you know, I would say we're two and a half years in and I just did a whole rev to our, our culture. And with input from the team that's now on the ground, we have, you know, yeah, we have almost 50 people. So what I wrote, you know, before didn't necessarily apply to today, but it's interesting, it ended up being pretty consistent.

Oh, you're throwing me red meat here for a coach. So when you were on the plane and you wrote down that culture, first of all, how did you think, why did you do that? What catalyzed that? What structure did you use to write that down? And of course, what actually did you write down? What are the specifics of the culture you wrote down that day?

Well, the structure was just a Word document. It was just like a, literally just, it was just a brain dump in a Word document with bullet points. And, and it was kind of, you know, Back to my McKinsey days. Tried to put some, some structure to it. I think I had five right now we have four kind of key points. I think I had five at the time.

Yeah.

What were they? And I, you know, I think so. I'll tell you what the current four are. And we basically just combined two into one of them. But the first and foremost, the thing that matters most to me especially really building a B2SB company or B2 consumer, is the customer's gotta be the North Star. And a lot of companies say that. But when you actually really build a company around that, there's things that you do that are just truly remarkable. If a customer has a problem, you drop everything you're doing to go solve that problem. And that's the kind of company I wanted to build. And because I've been around lots of companies, you know, I probably worked in or around 100 companies in my career, I was super lucky. Between KKR and, and, and McKinsey and then the various other different jobs I had in M and A that we did at HP to really see just a huge host of companies. And that is the overarching core guideline of our company.

Yeah. So customer.

Customer, absolutely. It centers everything we do. And then the second thing is really we are action oriented innovators. And the reason I like, I always, I think it said something before, like we have a bias for action. And then we had a separate one for innovation. But innovation is about being action oriented. It's about not overthinking. It's really hard for teams to release stuff into production that's not fully baked. But if you're an early stage startup, you gotta get stuff in the customer's hands because you can talk yourself in your own brain and your own team into something and you release it and they don't use it, they don't like it doesn't work. You over engineered. What they wanted was something super basic. And so, you know, that was kind of really an important element. That was our second element. The third element is we're a high performance team made up of talented, diverse individuals. And in team comes before the individual in that statement, because it's a little bit back to what we talked about in Ranger school is like, and I was talking to my team today, we had an all employee meeting and we went through all the metrics for every aspect of the business. There's some that are doing great and some that are not doing so great. And I said to the team and said, look, we're kind of hitting on a lot of different cylinders. But the thing that makes me most proud is that I had dinner with a couple of my team members last night and they told me, they said that we're so proud to be a part of Zebo. And the reason why, the reason they told me is because everybody on this team was. Works together as a team, cross boundaries with one goal in mind. And I was like, wow, blown away and super, super proud. And I've also been told by people, we never talk about diversity in our company. We don't talk about it, we just do it. I will tell you that there's a lot of people that talk about in Silicon Valley that don't do it. And I look at those guys and just kind of laugh. Yeah, we do it. We do it. And we do it every day. And we do it with our talent and we do it with our customers.

Yeah.

And that's just always been my philosophy since I was a kid. I learned that from my mom. And, you know, how'd she teach you that?

How'd she teach you that?

I mean, for one, she's a white woman from Buffalo, New York who married a Chinese guy off the boat.

Yeah, yeah.

In the 60s, right? Yeah, yeah. And then, you know, we always grew up with. I grew up in Louisiana where 50 plus percent of the people are African American, and they were always our friends and came to the house and had dinner and, you know, I had a family that one of her nurse friends was white who married a black man at our house and we called him uncle growing up, like, and we didn't know any, like, we didn't know any different. And you know, that's just like.

So it was embedded in your upbringing, really.

Just. My mom taught me. Yeah, yeah. And then, and then the last one is we're honest, genuine and respectful always. And when we talk to the team about that, you know, it sounds like a soft and fluffy one. We're honest, genuine, and respectful always. But our culture is not a, you know, passive aggressive. Everybody is like, everybody's happy and everybody's nice, and we're honest and we're genuine. So when, like, people tell me, like, Chris has a stupid idea, and I'm like, yeah, why? Why? Why do you think it's stupid? Like, we argue. Like, we argue about stuff because everyone has a different point of view. But in the day, we make a decision, we move on. But if we do that on a basis where people are willing to take feedback and they're willing to give feedback openly, you know, that to me, makes a really strong culture. And in fact, I Learned that from McKenzie. I mean, McKinsey, you had this belief around obligation to dissent. And oftentimes a McKinsey problem solving session would start with the most junior person in the room sharing their point of view and being encouraged to argue with the most senior person in the room. And it was how you got to a better answer and you respected everybody's point of view. Now, you don't necessarily do what they say. At the end of the day, the leader's got to kind of make the call. That's what a leader's job is. But, you know, those are some of the things. And I think most of what we had has just been refined and maybe streamlined. But again, it's. It's. It's this. The customer brings all of that together.

Yeah. So, like, that's a centerpiece, as you said. That's so interesting. So, like, you were on the plane, you were writing this down, thinking about starting this company. You brought this to Rob and Gregor. And I'll just say, for myself, as a coach, I regularly talk with founders about culture. And some are like, yeah, culture. And some are like, oh, yeah, we'll do that in. We'll do that in the future, you know, once we're more established or, you know, it's like a nice to have. But it sounds like that was, like, one of the first things you did and that you and your co founders talked about. Why was that so important to you?

Because that's one of the reasons why I wanted to start a company. I wanted to build a company with no legacy issues. And actually, it's funny, it took me a little while, probably a year in, because the first six months were frustrating and really hard. Like, not knowing, like, what is really the strategy. There's no such thing as a strategy if you don't have a Product like, you know, we kind of like, kind of had a vision, kind of had a strategy, had to find partners and suppliers, had to find people. And like, you know, it was to recruit people. You needed to be able to show them something other than like a PowerPoint deck. And so funny enough, what I relied on was that Word document that we did on the culture of the company and, and also, you know, making sure that my co founders and investors were all aligned around that. And I think that really what was remarkable to me because I just did this, we've hired so many people and we did like a culture session where I shared it with everybody, you know, a year, year in. But then like fast forward two and a half years, I realized we, like the vast majority of people in the company, hadn't seen it, but they've been living it. So I redid it, tightened it up a little bit, got some input from a bunch of the team members and then redid it with the team. And what's remarkable to me is I hear them playing it back to me now. And you know, everybody has access to the culture document and they could edit it. It's a Google Doc, so it's a, you know, we turned it from a Word document into a Google Doc and then turned it into a Google slideshow. And everybody can edit it, they can go in, they can type comments or whatever, but it's a living, breathing thing. And you know, and who knows, maybe it changes. You know, the thing that I challenge my team on is because the parts of the culture that they really love that I think also make us successful. You know, how do we keep that when we're 500 people?

Right.

That's, that's the hardest thing right now. I interview everybody in the company. Can I interview everybody in the company when we're 500 people? I don't know when I stop, like right now I'm getting to the point where I'm pretty busy with interviews.

Yes, I can imagine.

You know, I still like it.

Yeah. Well, I spoke to the founder of Better, Alexi Robichaux, and he said that he and his co founder were committed to interviewing personally the first 500 employees because those are their cultural co founders, he said. And it was so important to make sure that that culture fit was there early on because they're going to hire other people. And if you're going to build a massive company, you know, these are your early seed stage. Right.

So important that's.

So when you have a few different questions for you about, oh, I have one Other.

Sorry, I have one other point around that I kind of lost my train of thought. But one of the things that about a year in, I realized was, you know, I went into this thinking, hey, I really want to do this, because I can hire every person. I build the strategy, I build the culture. And it all really. It's. It's. It's. It's really a reflection of. Of. Of what I'm building. And then a year in, when I was frustrated around a number of things, I realized that I built the culture, I built the strategy, I hired the team, I decided what we did, like, and I was kind of, like, really depressed because I realized, like, it's my fault. And so I. I actually coined. I don't know if this is. If I coined this phrase, but I use it with my team is I call it the leadership selfie. And anytime you want to know what a problem is, you go like this and you take a selfie.

That's a leadership selfie. I can almost guarantee you've coined that. You should TM it.

And I really do believe that when you're a founder of a company and you're operating it as well, it really is the leadership selfie.

Yeah.

And it's hard. I mean, God, all of us, as human beings, want to make excuses for our shortcomings. I mean, I. But. But it is. It's so true. Yeah.

And it's also. I mean, it's a selfie that you then look at and you sort of see all the warts and all the wrinkles and all the difficult parts. So what's that like for you? So when you took that first leadership selfie, what did you see?

A lot of everything that you said. And, you know, I still do. I mean, it's really interesting. I've. You know, I've had a lot of leadership roles since I was really young. I mean, I started having meaningful leadership roles when I was probably 15 years old, and I had a disciplinarian in high school who basically, I was a very troubled child in my high school. And I became famous the second week of my freshman year for nothing, something that wasn't very good. And so I spent a lot of.

What was it? Come on.

I'm not going to say it was. Let's just say that there was a fine line between me being a very constructive leader in my high school and going to West Point and, you know, ending up in jail. And I just had a disciplinarian took me under his wing, and he started getting me involved in Leadership stuff. And, and then I actually had this brilliant idea that well, everybody in the school now knows me so why don't I run for student government? So I, I leveraged the fact that I was busted in a very public manner in the whole school to, to, to be elected into student council and then became a leader all throughout that time frame. But like, so I've been doing a lot of, you know, leadership for a long time and I, I just realized like as a startup CEO there's so much stuff to screw up and you don't have the systems and people and processes in place to kind of keep you, you know, kind of the guide rails and you just, it's hard, it's hard. And you don't like, unless you've been a three time founder, you don't know what you're doing. And I mean my team is not listening to this. But you kind of just figure you figure a lot of things out as you go and, and you know, sometimes you think oh my co founders know this but they're not in it every day, they're not operating it. And you know, the investors know it but like they're super busy. So like they're counting on you to figure it all out. They give you advice but they don't have all the context, don't know the people as well and you just start figuring stuff out and you make mistakes. Yeah.

So what is something that you've sort of figured out either recently or in the early days that you sort of figured out by yourself? You're first of all you're confronted by an obstacle, you figured it out by yourself. And either maybe let's say one of the things you made a mistake on and you had to then course correct. What's an example?

Well, as long as you, I mean the great thing about building a team is that you're, you don't have to take as many leadership selfies because if you build a team with the right culture, they're just taking pictures of you failing and then showing you it's a little bit of a team. Yeah, well, look, I mean we, you know, I hired a, a guy in, in March who's completely restruct our go to market. He's completely restructured our channel partnerships and we had partnerships and we were operating in a way that probably wasn't going to get us there on some of our core products. And I'm not going to go into the details, but it really took having a new set of eyes and fresh blood with some experience in the company and really giving them the empowerment to change a lot of things that we were doing. Till you realize, like, oh, my goodness, that, like all that stuff, you know, we could have done it way better.

But you know what? That, that is how you learn kind of figuring it out. I mean, I guess I'm just coming back to what you said before, which is before we started recording, you said, oh, I was just telling my wife that, like, this entrepreneur stuff is a humbling experience. What, what else has been humbling about it? Because I have to say, Chris, I look at you, you are indeed an experience and a pedigreed person at this point, and yet you're finding it very rough, right, to be on this journey. Tell us more about that.

Well, so first of all, hiring people is really hard. When you have nothing, you. You really are selling a dream. And, you know, you really are selling a culture. And you know, in, in your, in like in the early days, like, so I had, I worked in some of the best companies in the world and we never had problem sourcing the top talent ever. And it's never like, you know, from West Point to the army to, you know, to General Mills To McKinsey, KKR, HB, we could always source great talent. And then it was all about the process to wean it down to get that right person. But like, in the first year, I was literally had a backpack and tennis shoes on and I was going to all over the Bay Area walking for most of the time because pre Covid traffic sucked. Yeah, that's right. And so I would just walk with my backpack all day long for weeks at a time, getting told, no, no, no, no, you're too early. Too early. I had hire.

You mean not for funding. To hire.

Yeah, to hire you in front of the door.

Yeah.

And funding is no different. I mean, I'll tell you the thing that it'll bring this back full circle on ranger school, but like, you know, getting told no and no and no. And I remember I interviewed this really young, you know, late 20s, smart ex Stanford guy and for a product role. And he looked at me and he said, look, I'm just going to be honest. Like, you know, I'm looking at you and I don't think you can be successful as an entrepreneur. And he's like, you just know how to do big companies. And I had a venture capitalist saying the exact same thing. I went and did a partner meeting. These guys didn't even pay attention. Literally. I'm telling you, I almost like, if you look at my Background. Usually when I walk in the room and I present, people give me at least the respect of looking me in the eye and listening to what I have to say. These guys met me in a bar, they canceled. They stood me up. The first time they met me in a bar with a partner, all the partners, and they're eating and like on their phones and like not even engaged in what I had to say. And they, then afterwards they like ding me and they're like, no. And I said, hey, look, you know, can you give me the, you know, the benefit of giving me feedback? And the feedback was, yeah, no one thinks you're going to be successful because you came from big companies. And so the combination of rejection, which I really hadn't had a lot of professionally, but it was just so hard and it was so emotionally taxing. And I remember I used this analogy before. It's like, you know, when I got out of Ranger School, 35 pounds lighter, but then I started eating a lot of food. My belly just swole, so I was like skinny everywhere. My belly was swollen, I had no hair on my head, it was completely shaved and had bad skin from being in the swamps. And I go to a bar and try and meet somebody because it's single. It didn't work so well. I can see that that's kind of like what it's like in the first six months of trying to build a company.

Wow, that's a great metaphor. So, so how did you handle that rejection? And also, that's not well. Yeah, so what was it like? And how did you handle? Because again, it was not one day, it was six months. It was like a period.

Yeah.

How do you, how do you withstand that?

I mean, I think you just figure out how to, how to plant a stake in the ground and say, okay, that's what we're going towards. And you know, it might not like you as a startup, you could go anywhere. You have a white. You have an idea. We're going to make a financial services company for landlords. Okay, what landlords? What geographies? What products? What do you need to build that? Like, do you need any licensing or regulatory requirements? You know, how much money do you need? Like, who should you look? I mean, literally every dimension is just, there's no like path. And, and so, you know, after a couple months of just kind of like we had a kind of a high level vision, but just kind of spending. Where do you start? I just said, look, here's where we're starting. We're starting here.

What Was the here.

So we actually basically planted the flag around. We're going to build a landlord bank as our core operating thing. One of the things I fundamentally believe it goes back to customers at the center of everything you do is deep customer insight. And so we hired a woman, Anne Beale in Chicago, and we just talked to 40, 50 independent landlords and tried to create archetypes and what were their core needs and what were the big gaps, what were the things that they were happy with, not happy with. And we tested this concept of, you know, building a one stop shop for financial services and none of them, all of them love it, none of them believe it could be done. Kind of like a lot of stuff I've done in my life. Yeah, that would be amazing. But nobody's gonna do that. And like a lot of people were like, well, there's not a lot of opportunity. I'm like, there's opportunities kind of like, you know, dumb and dumber. When she says like, there's no, there's a one in a million chance that you can date me. And the guy's like, oh yes, I could date. There's a chance.

That. So that's where you started. It sounds like.

Yeah. So we said, well, so we learned from that research that the core of the operating system for accounting in the day to day was the bank account and that they had lots of bank accounts and trying to keep all that straight and the record keeping associated with that was really challenging. Also in that research we discovered that 95% of landlords, when asked, do you have the right coverage for the right price for insurance, said number one, either no or I don't know, 95% of them. And when you qualitatively talk to them and say, listen, it's the most opaque. I gotta have it, I don't have a choice. I get a loan, I gotta have it. I bought it from my brother in law who was, you know, a high school linebacker and probably got hit in the head too many times. But you know, like, like that's it, that's the industry.

Yeah.

And, and, and, and so they're just a massive, massive opportunity to go solve a recurring pain point around, help me know when I'm being paid, manage my cash flow and stay organized.

Yeah.

That is daily, weekly, monthly pain point. And then, oh, by the way, I don't even know about this insurance thing. Like help me learn about am I getting the right stuff for the right price?

Yeah, yeah.

And oh, by the way, I also need to finance things.

Yeah, yeah. So it Sounds like you're almost like your first job and your first as a CEO. Your first job and your first six months was around like, what the heck are we building here? And then you figured that out with your customer insights and you eventually be able. We were able to hire people hopefully in attuned with that culture you talked about. And now it's like two, two and a half, three years later. How has your job as CEO changed?

Ah, oh, my goodness. I mean, in the early days, there was a lot of sitting around looking at the wall because it was only me. I could. I could edit my own document and present it to myself if I wanted to. But like, you know, I had some money in the bank actually. It was funny the first month, I'll tell you the story, like, we got. We raised money, we got in a bank account. And then I'm like, so do I just cut myself a check? Like, how does this work? Like, how do I pay myself? Yeah. And I talked to a couple founders and some of the VCs. They're like, oh, yeah, we need. You need some payment system. And I'm like, okay, like, what, what, what can I use? And somebody's like, oh, yeah, there's this place, this thing called Gusto. I'm an advertisement. I'm like, okay, what does it do? Well, it's a HR payment system. I'm like, well, I didn't even know what an HR payment system was because, like, you know, I ran it for hp. Like, it reported to me at the cio. I didn't know what. Like I just said, hey, make the payments thing work. Yeah. You know, and then we had a whole HR team that made the, you know, workday work and the peoplesoft work and whatever it was work. And, you know, I just like logged in and stuff happened. So pay myself at his. Set up an HR payment system. I mean, start with that to like roll forward a year later. Like given day, I'm talking to investors, you know, trying to raise money. I'm going through the customer operations we have every week we have an hour and a half long all employee customer operations meeting where our frontline customer success people present all the data and statistics on all the problems customers have, all the, the requests they have, the escalations that we've had from a support perspective. And everybody in the company is required to sit on that because I want them all to know it starts with the customer. And I've got a lot of slacks and flack around that because it's time consuming to spend an Hour and a half. And it is the people that talk to the customer all the time telling the company product design, engineering, strategy, ops, me, what's working, what's not working. At the end of the day, you know, you got to balance because there's a lot of things that customers want that we just don't have capacity to build for six months. And so really trying to figure out like how do you balance those things where it's urgent and important versus it's really important, but like it's not urgent. That's really hard. That's. I spent a lot of time doing.

How do you balance that? How do you think about?

I think, I think you have to kind of really focus on what are the things you're trying to drive. So right now in the stage that we're at, we're trying to drive customer acquisition, retention and payment volume, revenue. Like I mean, payment volume just going through the platform and so keeping the team focused on that onboarding process in the, the first moments of truth that the customer has with Zebo are so critically important to our long term success and that those take precedence over things that might be, you know, the right thing to do and might impact a lot of customers, but ain't going to impact that. Those metrics in the early, in the early days, it's really hard actually. I actually listen to the, the, the, the founder of, of LinkedIn at a conference talking about this and I was really blown away, was really impressed where he, he said, we had a couple of times where customers were really unhappy and they wanted certain features and functions that we didn't have. And the hardest thing to do as a customer focused company was to focus on the roadmap that would really deliver a much more holistic thing that would be much more valuable to them and ignore the near term noise. And that's really hard to do, especially when you have customers or the North Star and your team saying, well, the customer's saying this. So I didn't answer the question. I just think it's a lot of listening to the team and then ultimately making a gut call. I go against the team a decent amount and it's not because I'm not listening to him, it's just that I think that there's a longer term vision that sometimes we just need to focus on and sometimes we don't have facts to support the decisions. We just got to make a gut call based on where we think the market is, where it's going and what the customer we think really wants. That's tough.

Yeah. How do you know when to make that gut call versus when to use data?

My gut, I know it sounds stupid, but like, it's just like if I feel so deeply convicted about something, like, I really value the team and their perspective and I want to hear it, but if I hear it, all the perspectives, but I still feel deeply convicted about something, I'll try and explain to them why I feel this convicted. But they know that at the end of the day, somebody's got to make the call. And, and ultimately, if you're a young company, the thing that fuels your engine is capital. And if I and nobody else knows in the company what stories resonate with investors because no one else is talking to them every day. And so sometimes I make trade offs in what might drive things now with customers to plant seeds for things that will help us get fuel for growth. And that's hard. That's hard.

Yep, I hear you. Wow. Just a few more questions. I'm just curious. When you, when you have to have complicated or difficult or delicate conversations with your employees and with your executives, what are some of the most awkward or the most challenging like that you wish you had a script to use to help you with that? Oh.

I mean, just kind of building off of the last point we just made. What's really hard is when the company feel strongly about going in a direction and you feel strongly about going in a different direction. And by the way, when you make that decision, because I've made a lot of them in my career, it's the riskiest decision you make because if you're right, everyone's like, oh my God, Kris was right. And if you're wrong, everyone's like, he screwed up and we were right and he was wrong. And the natural tendency of a human being is to say screwed up, we were right, he was wrong. And so I weigh those decisions remarkably difficultly. And like, I'll just tell you, you know, you're almost not a year ago, but pretty close to a year ago, we were having major issues with kind of core infrastructure and technology all because we've stitched together a number of different technologies and providers in order to create a very unique customer experience. Doesn't exist anywhere. And it's hard stuff and it breaks and it's not stable because if one provider changes something and you've integrated it in a way that interfaces with another, but it just doesn't work. And the team wanted to re platform everything thing and, and I listened and they, it was about two months of like the team doing a ton of work. And, and I, I really knew deep, like, deep down inside that didn't want to do that. And I knew, like, I just had a gut feel that that would be really challenging, eat up all of our innovation resources and put us in a situation where our back would be against the wall from a financing and Runway standpoint. I just finally said, guys, there's. I appreciate all the work. You guys are really. There's zero situation, zero circumstances where this CEO in this company at this point in time is going to re platform not happening. I said, maybe my fault, but I'm not making that call. And so I said, look, you guys can continue to work on this, but there's no scenario in which we're re platforming before we get to certain milestones. That's super hard because the team was completely convinced that was the right thing to do, and we just had to put it behind us and execute. And we've executed well, and now the platform's stable. The one on one conversations. I've had so many of them throughout my entire career. When I was 17 years old and I was at West Point, they taught us how to give feedback and, you know, you have leadership and you. And it's always about being genuine and caring about the person. Even when I've had to fire people, you know, making sure that you understand that, like, I would. Sometimes I fire people because they don't work for me, and I tell them, like, I'm just a different animal. Like, we just don't work well together. You're super valuable. You should go work with somebody who works better with you. And other times it's, you know, look, you have some substantial developmental deficiencies that you need to go work on, and we need to bring in somebody who can deliver. And those are hard conversations, but the more you do them and the more that you realize that the world's a small place and that people are going to call those people for reference checks on you. And if you do it the right way, those people might be your customers, they might be your partners, they might be your supporters. Long term, a number of people where I've had to fire that ended up being one of those. And, you know, like, if you do it the right way, you treat people with respect, you're honest, you're genuine and respectful always, you know, you'll maintain a good relationship. Yeah, yeah, I think never makes it easier.

Yeah, I hear you. But it is. It is kind of the best way to do it, as opposed to just like string people along and also kind of obfuscate your message. It sounds like you also focus on straight talk, but you're also that you're genuine. And you see, no matter what, there's a person there, and that's what she is.

Perfect example. We just gave a woman first job out of college. She'd been at Zebo for over a year. We just gave her her first review, and I was adamant to her supervisor that. That he put in the development needs and, like, real development needs. And she sent an email after her review. We promoted her. She's doing great, but we gave her very direct feedback about her development needs. And the things he said in her email wasn't thank you for the promotion. It was thank you for giving me real developmental feedback. Isn't that something?

Yeah.

People want. People want to hear what can they do to improve.

Yeah, totally.

Yes.

Chris, what do you wish you had known earlier in your journey?

Somebody would have told me how hard it is to build a company from scratch. I don't think I'd be here today.

So maybe you didn't want to hear that.

Oh, man. No, you know, it's just. It is. You got to be a little bit crazy to start a company. You really do. And you got to have a lot of thick skin and endurance. You have to believe. You really, truly have to believe. Like, the number of times that people around you don't believe in what you're doing. Your own team, sometimes your customers, I mean, some of the stuff some pissed off customers say is pretty bad. Your investors, like, your family. I mean, my wife is like, okay, you went from doing that and making that to doing this. Like, are you crazy? You're working harder than you ever have in your whole life. And. And you know that. You know, that's hard. You got it. Like, I wish. I wish I knew. I guess if I knew it, I probably wouldn't do it. But, you know, I was always. I think I mentioned this when we were off air. I was always a wantrepreneur. I was always a guy who was, like, doing well in my career, but I always wanted to be that entrepreneur. And, you know, I would look at somebody's business and be like, oh, you know, they screwed this or that and the other thing up. And, you know, I could have done that better or whatever. But then when you're in the seat building company, like, it's just way, way more complex and harder, and you're always, you know, you're always really close to, like, it not working. Like, it's just Remarkable how close you are to the hard reality of failure and, you know, great companies. I mean, I think it's the founder of Airbnb, like, he has this great chart where he, he has all the rejections that he received from VCs along the way. When I read that, it was like, so inspired.

Yeah, that's true. He's got them all up on his wall, I think, in a frame. Brian Chesky.

I need to do that. I think I, I think I've got, I think I got way more than he does.

Well, my last question is, what advice do you have for other founders as they embark on their own journey to grow into, into leaders.

From a leadership perspective. Man, I tell you what, I, I, it's so funny. I see guys like Oleg Raginski, who's people, AI CEO, who, who was, I was an advisor to and spent a lot of time with. I was so remarkably inspired by him. And I told him when we went, when I, when I started my company and he invested in it, and I said, I've learned more from you than you learned from me. And just, you know, the conviction, the endurance, surrounding yourself with good people and letting them do their jobs and pushing them hard, hard, not being afraid to push when you need to push and staying, you know, keeping the vision. You know, your, your investors are investors. They're not going to tell you what to do, how to build the company. It's not, they got lots of ideas. They're super valuable. They really want to help you be successful. But, like, at the end of the day, it's up to you and your team and you guys got to make the calls and you got to deliver the results. Because end of the day, investors invest around a dream. But it's the, Somebody told me this. It was actually a combination of Sebastian Troon from Udacity and Kitty Hawk and Oleg. And it's like the idea isn't worth anything. It's the execution that matters. And execution is about building the right team, getting focused in the right direction, and empowering them to do their jobs.

Chris, what a great last word. Thank you so much for joining me today and for adding value to this podcast. And I know that the people who listen to you are going to get.

A lot out of it.

So thank you.

Thank you, Elizabeth.

Thanks again, Chris.

Thanks for listening to From Startup to Grown Up. If you like what you heard, give it a review on Apple Podcasts so other people can find it. And if you know of a founder or someone else who is meant to be on this podcast, drop me a line through my website alyssacon.com.