Heroes in Business - Spencer Rascoff, Co-founder & fmr CEO @ZillowGroup, Co-Founder & CEO of 75 & Sunny Ventures getrecon.app

Episode Date: March 21, 2025

Spencer Rascoff is an American entrepreneur and businessman. He was the co-founder and former chief executive officer of Zillow Group, as well as one of the co-founders of Hotwire.com. Rascoff was on the board of directors of Palantir. He's also the Co-author of Zillow Talk and a Host of Office Hours podcast. He was interviewed by David Cogan at the Eliances Heroes Show. getrecon.app

Welcome back to alliances heroes. We're heroes in business aligned to be part of our super community and find out more about alliances visit www.alliances.com. That's right. And we just had on the CEO bitly. So thank you again to for the feedback we got during that show. And later on, we're going to have, are you ready for this? He's part of NASCAR. He's got a NASCAR car. He owns the team.

He owns a giant company called Leaf Home. If you haven't heard of that, they own a bunch of different companies. So make sure you continue to stay tuned. But I'm very excited about our next guest today. I'm sure you probably heard of one, two, maybe three of his companies, but welcome to the show. We have with us Spencer Raskoff. He is the co-founder of Zillow.

Yeah, we all know Zillow. It pops up all the time, right? Hotwire.la, Picasso and more. And we're gonna get into what he's doing now which is absolutely amazing but before we do is is spencer talk to us about this little small company you started that just became enormous of being the co-founder of zillow like i think everybody on you know at least in the united states has heard of zillow thank Thank you, David. I appreciate it. Yeah, look, you know, I started Zillow with a couple other folks back in 2005, it feels like a million years ago. And the goal of Zillow was trying to empower

people with access to information about real estate so they can make smarter decisions about their home. And I'm so proud of the team that I worked with over 15 years to build that into the company that it is today. I retired from Zillow about three years ago to start other companies and to be an investor and to do lots of other different projects, including some of the ones we'll talk about today. But certainly Zillow was an incredible experience and I'm so happy to have played a part. I mean, do you ever just look back and just go like, you know, this came from an idea

and just became enormous. Everybody uses it. It is a little surreal to be honest. I remember, it wasn't that long ago that when I would meet somebody, I would say, oh, I'm the CEO of Zillow and they'd say, what's that? And I remember when it sort of tipped,

it felt like it was around 2010, 2012, when I kept saying like, hey, I'm Spencer, I'm the CEO, it felt like it was around 2010, 2012, when I kept saying, like, hey, I'm Spencer, I'm the CEO of Zillow. And I'd say, oh, it's a real estate website. And they said, no, no, I know what Zillow is. And so when that changed, that was a fun moment, a fun tipping point for me. But yeah, it's a little surreal still to this day. And if that wasn't enough also to Hotwire, I mean, like the list just keeps going. Like, you know, I think we just need to keep you

like in a room and just spit out all these ideas and sell for, you know, a few hundred million each. Well, if you kept me in a room, I wouldn't accomplish anything because it, and then I'm not just saying this, but each of these companies has been the result of a great team that's worked hard together. And so, you know, my, my, my work at Hotwire was an incredible team, and we sold the company to Expedia, and then we left Expedia to start Zillow, and that was an incredible team. And now Picasso, it's all about the team. So none of these things are done. Entrepreneurship is a team sport. It is not a solo endeavor. So Spencer, how do you find the team then? And how do you know that you're part of the right team?

It's a great question. Something I still struggle with every day. In fact, I keep a spreadsheet called Great People, which is literally a list of all the great people that I've worked with in my career and all the positions and their experiences and I use that as really a database. And actually, here's a good tip for listeners. One thing I did when I retired from Zillow three years ago, and it was time to look at a blank slate and start coming up with ideas again and start assembling new teams, I sent an email to about 100 people and said, Please tell me the three best

people you've ever worked with in your entire career. Just you know, names, LinkedIn profile,, you know anything and I got an incredible amount of great material from that of people to work with So, you know, how do you know when you're part of a great team? It's it's hard because there's no such thing as a great team for all stages I mean there are people that are great at a role for a particular point in time, and then perhaps the company scales past their abilities and you need to change out that person or even a team or group of people are maybe great at a particular stage, but then maybe they as a team don't scale. So as when you're working with these dynamic companies and startups, especially as they go through a high growth period, you have to keep reassessing whether you have the right people and the right teams in place at different stages. I love that idea, you know, asking others, getting a list, and did you see any crossover with the list? Did anybody name the same person? Oh, yeah, many times. Those, and those get extra, extra gold stars next to them, but for sure.

Absolutely. A lot of repeats. All right, so if you haven't created enough companies already, enough jobs and enough things to make your mark in the world. Yep. You're not stopping. In fact, why don't you steal the thunder of what you're doing now? Sure. So the most recent, I started two companies recently.

One was called Picasso, which I co-founded with Austin Allison, who I know has been on the program before. And he's a great entrepreneur that started a company and sold it to Zillow. So I worked with him at Zillow. And Picasso is helping people buy a portion of a second home. So it's a great way to democratize access to second home ownership. The other startup that I'm doing is with my co-founder,

my daughter, my 16-year-old daughter, who's a junior in high school. And it's called Recon Food. And it is a social network for food, whether it be home cooking or food at restaurants. And what we're trying to solve with Recon Food is the fact that social media is really broken in a lot of ways.

If you spend time on Instagram, spend time on TikToks, spend time on any social network, it can be exhausting and also it makes you feel bad about yourself. And the the hurdle to post on these platforms is very high because there's this need for perfection. You know, do I look good enough? Is this thing that I'm doing interesting enough? Is this vacation that I'm on extraordinary enough to post? Recon food tries to strip it down just to the bare essentials of just food. And by having a food specific social network,

it creates a safe community where people are posting the dishes that they've cooked, whether they be good or bad. And it's a safe space to talk just about food. And we see this in other verticals too, where social media is unbundling. So you have all trails for hiking or Strava for running or Peloton or Fitbit for fitness. You know, you wouldn't post on Instagram your run like, hey, I just ran five miles in this time.

But on a social vertical social network for sports or for athletics like a Strava or Fitbit, of course, you would post that there. Likewise, that's why recon food exists to share your food creations in a safe food specific place rather than on horizontal social media. So It's been fun incredibly fun working with my daughter on recon food And the product has many dedicated users that love posting their food creations there And uh both video and and photos And how does it come to be? It's a it's a great question, David, because it

shows the importance of diversity in teams, the recon founding story. So when I pitched Sophia and my family on this idea during quarantine, I said, I want to create a way for people to discover restaurants based on their friends' recommendations. And my daughter said, you know, we're on quarantine. Social media is supposed to be this respite, this place to escape from the

challenges of everyday life. But when you open your Instagram, it's people upset about things. It's people complaining about politics, complaining about mask mandates and vaccines and election hacking and climate change and all these challenges and issues that have permeated through social media because most people get their news on Instagram and Facebook now. So in my daughter's eyes, social media was exhausting. And so we kind of combine these two ideas and created a vertical social network just for food, one that would leave you feeling good about yourself at the end of 10 minutes of browsing. You're just looking at pretty pictures of food. That's it.

That's all it is. There's no debate. There's no Republicans or Democrats. There's no politics. There's no peacocking about, you know, my life is better than your life or, you know, do I look good enough or am I doing enough interesting things? It's just food. And so the founding genesis was really the combination of these two problems, one that I had around restaurant discovery and one that my daughter had around creating and enjoying social media in a more simple stripped down version

just focused on a single category of food. Now we're gonna be asking you here soon about how it is working with your daughter, 16 year old daughter, because we have with us Spencer Raskol, he was the one that co-founded Zillow, Hotwire, Picasso, and many more, and now is working with his daughter. And they are, you can reach them by going and getting the app and going to getrecon.app. It's also too below, you'll see it in the image below here, the banner, getrecon.app. That's G-E-T-R-E-C-O-N.A-P-P. Because you're watching, listening to me, David Cogan,

host of the E-Lionces Heroes Show. Make sure you go to elliances.com, E-L-I-A-N-C-E-S.com. Because as you know, it's the only place where entrepreneurs align. All right, Spencer, you're working with your 16-year-old daughter. Tell us how that is. I mean, you know, first of all, how do you not stop talking about work

when you're at the dinner table? It's it is it is a challenge. You know, I walked into her room last night at 1030 because I have my wife and I was time to go to sleep and she's of course up doing her homework. And before I could say goodnight to her, I had to file a couple bugs with her, you know, show her some things that I found in the app that I think should be changed. And before I could say goodnight to her, I had to file a couple bugs with her, you know, show her some things that I found in the app that I think should be changed. And she of course dutifully puts them into Slack and, and our other forms of collaboration where she manages the engineering team. So so yeah, I mean, we're always on from breakfast, from

breakfast through through bedtime. You know, it's what I've enjoyed about working with her has been, uh, seeing the diversity of skill sets. I mean, she's a software engineer. I'm not. So she actually knows how to code and review code. I don't. Um, uh, you know, she experiences social media constantly through the eyes of a 16 year old. I don't.

And so she has problems with social media and identifies problems with social media that recon food can help correct In ways that I don't experience social media. I have other skills, of course that complement hers I'm a much more experienced, you know tech executive and founder and so she can learn from me So just like when you're building any team It's important to have diversity of experiences diversity of viewpoints with diversity of backgrounds at recon food, we certainly have that even though the two co-founders are father daughter. That's right. I'm sure it makes for interesting conversations at the dinner table. It does. It does. And our other kids have gotten into it too. You know, our 10 year

old, my 10 year old, Katerina is constantly on recon food posting cupcakes that she makes or last night she made snickerdoodle cookies all by herself. She's a 10 year old. And, you know, it's a good example, right? She she's not allowed on Instagram. And even if she were, I wouldn't let her post on Instagram, because she would see all this other content on Instagram that I wouldn't want her to consume. But she loves recon food. She uses it to reconnect. That's where the term recon comes from to reconnect

with friends and family over a shared love of food. And there's my 10-year-old posting her snickerdoodle cookies on recon. Well that's excellent that you're working with your daughter Sophia. You know it's just and I'm sure in ways it's brought you together closer too. It has, it has for sure David, yes. So talk to us about some of the secrets maybe you share with your children about making their mark. I mean, clearly, Sophia is already now on the track for that. And what about your younger son?

But you know, you've had an extremely successful career. I mean, you've made your mark, you're continuing to do it. But how do you also share those secrets with your kids? So, I think it's very important for children to learn grit. And quite frankly, you know, my kids are growing up in a very affluent household. And so it can be difficult to learn grit if you grow up affluent. And so my wife and I do our best to model behavior for them of prioritizing hard work, first of all, you know, even though I've had success Prioritizing hard work first of all, you know, even though I've had success previously I'm still working hard my wife is a doctor and nobody works harder than my wife and so my kids see that and they learn the importance of hard work and

You know, they also know that nothing's gonna be handed to them. So Even if you are raising kids in a household that has had good fortune I think it's important to still teach kids that they're gonna have to make it on their own and That you know, nobody's gonna hand anything to them. So those are lessons that my wife and I frequently teach our kids. And where was the idea born of even wanting, you wanting to become an entrepreneur?

I mean, is this something you learned from your parents? I did, yeah, so I did learn it really from my parents. So my dad was a an accountant. He was graduated from Wharton undergraduate School of Business at Penn in 1967, went to work on Wall Street as an an accounting firm, and was the youngest partner at a big eight accounting firm. And in 1972, he was in the men's room at his accounting firm in New York.

And there was a gentleman next to him washing his hands, kind of grumbling under his breath saying, oh, this fancy accounting firm won't take on my client, British guy with a British accent. And my dad said, you know, what's the problem? He says, my client is the Rolling Stones. And, you know, I flew here from London to try to get your accounting firm to take us on

and audit our tour. And they wouldn't have anything of it because the Rolling Stones back then were throwing TVs out of windows and doing all sorts of drugs and were kind of unsavory characters. And so my dad said, well, that sounds interesting. And so he quit his partnership and joined as the tour accountant on the 1972 Rolling Stones European Tour. And by the time I was born in 1975, his career, which became a 40 year career in entrepreneurship had gone on to become the business manager

and tour producer for the Rolling Stones, U2, David Bowie, Pink Floyd, Paul Simon, the police, 38 Special, Leonard Skinner, and on and on. And so I grew up watching my dad Having carved out a career of entrepreneurship From what started in a very safe place, you know he could have just stayed as an accountant and had a very successful career as a partner in an accounting firm and He threw it all away to take this leap for this risky career path which turned out to be fascinating and fun certainly fun as a kid, but also fun for him and

And that was a very formative experience for me as a young person learning from him. You ever wonder what you would be doing if you weren't being an entrepreneur, if you weren't having had so much success with the companies you have? I think I'd be a teacher of some sort. I mean, that's really what I feel I am right now.

I teach, I mentor, I coach, I literally teach a course on entrepreneurship at Harvard, at Harvard Business School and Harvard College. But in everything I do, I'm teaching. So when I angel invest in early stage startups, I'm teaching and coaching those startups. When I sit on boards and I'm on a couple of boards, I'm teaching and coaching those executive teams. The companies that I co-found, whether it's Recon Food with my daughter or Picasso with Austin Allison, I'm teaching and coaching those management teams.

So I'm a teacher. I just happen to get paid through the stock value appreciation in the companies that I invest in or the companies that I help create. So if I weren't able to be an entrepreneur or a tech founder, I do a teach in some way or another. That's really what I love to do. What do you think's the best way though to learn of those that aren't going to Harvard

or taking the classes and those that have listened and watched this and yet want to? A lot of people dream of making their mark and starting their business, but how do you like even start? Well, it's so much that that question is so much easier to answer today than it was 30 years ago, because there are so many resources at people's disposal now. I mean, you can, you know, between YouTube and podcasts like this one, and books and blog posts and Twitter, you know, you can learn so much from these people that are pretty inaccessible in day-to-day life.

So I call this hacking mentorship. And I'll give you a couple examples. Sacha Nadella, the CEO of Microsoft, or Jeff Weiner, the co-founder and former CEO of LinkedIn, I consider them both to be mentors of mine. Now, they are mentors of mine even though I've hardly met them. I've met them a couple times. They kind of sort of know who I am, but we're not close. We don't talk frequently, but they are mentors of mine.

Why do I say that? Because I read everything they write. I listen to every podcast they're on. I follow them on social media. I stalk them. And whether it's Sacha talking about how he's turned around the culture at Microsoft and went on to write a whole book about it or Jeff talking about the mission and vision and strategy of how he built up LinkedIn, like I'm a student of theirs and a mentee

of theirs. So that wouldn't have been possible even 10 years ago for aspiring entrepreneurs to have access to those types of insights from these icons. So, I encourage people to go to town on all these resources that exist. To certainly start with Twitter as a starting point. Follow, start with 10 or 20 people and then Twitter will do a great job of recommending other people for you to follow.

You'll quickly get sucked into these people's worlds and then you'll see what they're reading because they'll post it there. And if you follow them on social media, for example, I'm going to post most of my Harvard class or kind of tidbits from it on my different social media platforms, whether it be my LinkedIn or my TikTok or elsewhere. So there's a lot to be learned from these people, even if you never meet them in person. Wow. Now, Spencer, I know you've done a lot of interviews, again, being, you know, co-founder of Zillow and Hotwire and all these other companies. And now again, you can be reached

at getrecon.app, getrecon.app that he started with his daughter Sophia. What's something you haven't been asked that you're like, you'd like to answer and tell the world? Something you haven't been asked. Because I know you've been asked a gazillion questions. I have been asked, yeah, that's a good question. When will you stop? Like when will you be done? I haven't really been asked that very much,

except by my wife and by myself sometimes. Of course. What? Well, actually, she doesn't she asks it really in the negative because she's not anxious for me to stop. She she you know, she likes that I'm that I'm keep working really till the bitter end. But I'm, I am change, you know, I'm 46 now and I'm definitely changing the way I approach work. Like, I'm not on the field anymore. So being on the field as a tech founder and entrepreneur, that is a young person's game. It is very difficult in your 40s, 50s, 60s, to have the, you know, the energy and focus and

the lack of other things going on in your life that is required to devote all your time and focus to a startup. And so I'm on the sideline now coaching or maybe even in the skybox coaching, you know, with the headset on. And I'm coaching games that are happening on a couple different fields at the same time. And that's a very rewarding place to be, you know, in my mid-40s, where I can have leveraged impact on games that are going on in a couple different fields, a couple different companies at the same time, without actually being on the field, you know, suiting up for the game every day, getting injured, you know, having crowds, you know, cheer and boo when things go well and not so well, you know, that is that is all consuming and is I'm past that stage of my career. You know, I love how you brought that together. I almost picture you in the

field box of a football game, right? You're managing all. Well, I gotta tell you, Spencer, you're a serial entrepreneur. You've created some of the most recognizable brands that have changed the way people book travel, search for home, and now working with your daughter, Sophia, on a new venture, that's a hero.

Spencer Raskoff, co-founder, Zillow, Hotwire, Dada Lae Picasso. You can reach them now with Recon Food. Go to GetRecon.app. This has been David Cogan with the Alliance of Heroes show.