Dave Selinger | Working With Jeff Bezos, Co-founding Billion-Dollar Redfin, and Leveraging AI To Fight Crime
Smart Business Revolution

Dave Selinger is the Co-founder and CEO of Deep Sentinel, an AI-based home protection technology. He was an early employee at Amazon where he worked directly under Jeff Bezos before pursuing entrepreneurship. Dave co-invented Amazon Advertising, now a billion-dollar division within Amazon. He also co-founded and ran Redfin, now a multi-billion dollar real estate brokerage. In addition, he revolutionized shopping experiences for Macy’s and Office Depot with his company RichRelevance. 

In this episode of the Smart Business Revolution Podcast, John Corcoran interviews Dave Selinger, the Co-founder and CEO of Deep Sentinel, about his experience working with Jeff Bezos and the entrepreneurial lessons he has learned over the years. They also discuss the value of understanding customer behavior, the challenges Dave faced building his companies, and his tips for balancing family with work. Stay tuned for more.

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Here’s a Glimpse of What You’ll Hear:

  • Dave Selinger’s entrepreneurial background
  • How Dave got to work with Jeff Bezos at Amazon and what he learned from him
  • The value of understanding customer behavior
  • Dave’s journey into entrepreneurship and the challenges he faced building Redfin
  • Dave talks about how work with international companies and nonprofits
  • How Deep Sentinel works
  • Best tips for balancing family and work
  • The peers Dave acknowledges for their support

Resources Mentioned In This Episode

Sponsor: Rise25

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Cofounders Dr. Jeremy Weisz and John Corcoran credit podcasting as being the best thing they have ever done for their businesses. Podcasting connected them with the founders/CEOs of P90xAtariEinstein BagelsMattelRx BarsYPO, EO, Lending Tree, Freshdesk,  and many more.  

The relationships you form through podcasting run deep. Jeremy and John became business partners through podcasting. They have even gone on family vacations and attended weddings of guests who have been on the podcast.

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Rise25 Cofounders, Dr. Jeremy Weisz and John Corcoran, have been podcasting and advising about podcasting since 2008.

Episode Transcript

Intro 0:14 

Welcome to the revolution, the Smart Business Revolution Podcast, where we ask today’s most successful entrepreneurs to share the tools and strategies they use to build relationships and connections to grow their revenue. Now, your host for the revolution, John Corcoran.

John Corcoran 0:40

All right, welcome everyone. John Corcoran here, the host of this show. And if you are new to listening to this program, check out some of our past interviews with interesting guests, smart CEOs, founders and entrepreneurs of companies and organizations ranging from we got the co-founder of Netflix we got Kinko’s, we got Quicken, YPO, EO, Activision Blizzard, LendingTree, OpenTable, and many more. And I’m also the Co-founder of Rise25, where we help connect b2b business owners to their ideal prospects. And my guest here today is Dave Selinger. He was an early employee at Amazon and worked directly under Jeff Bezos there later became a successful entrepreneur. Here are a couple of interesting highlights. He co-invented Amazon Advertising, now a billion-dollar company division within Amazon, then co-founded and ran the real estate brokerage Redfin, now a multi-billion dollar company, he revolutionized shopping experiences for Macy’s and Office Depot with his company RichRelevance, and now he’s working on a really interesting project called Deep Sentinel, an AI-based home protection technology, that I have to say, I was watching some of the videos and it was just blowing my mind how they combined AI with the real world. So it’s really an interesting technology to talk about here. So we’ll get into all of that.

Of course, this episode is brought to you by Rise25. We help b2b businesses get clients, referrals, and strategic partnerships with done via podcast and content marketing. And you can go to our website, rise25.com to learn all about what we do. All right, Dave, it’s such a pleasure to have you here. You’re just right across the bay from me, you’re over in Pleasanton area. I am over in the North Bay. And I want to start with your upbringing. I love to ask people about how entrepreneurial they were. As a kid, you grew up in Southern Oregon. And you said there weren’t a lot of neighbors around so you weren’t doing lemonade stands because no one’s gonna buy. There’s a lesson I was trying to tell my kids about placement of the lemonade stand kids like that’s, that’s half the decision. But what were you doing there was entrepreneurial is it? Good? Well,

Dave Selinger 2:34 

John, thanks for having me. So yeah, I grew up in a really small town in southern Oregon. It’s a town called Merlin, which right now in September 2022 is getting evacuated because of the Run Creek fire. So it’s a you know, it’s kind of an intense rural area. I grew up with wildfire. So it’s not you know, this isn’t like the worst summer of my life. It’s just another one. And part of the reality there. The population of Merlin’s a few 100 people. And we’re a suburb of a little town called Grants Pass, which is maybe 30,000 People now. And so, growing up, I, I always was trying to scheme my parents, that was how my parents knew something was going to go bad, it was gonna happen with me. And in so it’s always trying to get to make the most of whatever situation I was, in my very first entrepreneurial attempt, was probably trained to do something along the lines of of arbitrage for office supplies for my classmates, because I recognize when you went to the school store, and you wanted to buy a pink eraser, it was 50 cents. And if 10 of us got them, that was five bucks. And if you bought at wholesale, they were five cents each, but you had to pay shipping of three bucks. And I thought to myself, Man, there’s an opportunity that money, yes,

John Corcoran 3:58

yes, then the pink eraser gravy train. Yes,

Dave Selinger 4:01

that’s easy, you get on that pink eraser gravy train, and you don’t ever get off. Right? And, and pens, were a big one, because you could buy pens in bulk. And I mean, what I didn’t realize at the time was that margin is just what makes you know, that’s what makes capitalism want to get in every stage of the distribution chains, you have to have some sort of margin to handle operations and distribution and support and things like that. But to me, it was like out of nowhere, I was like, so all I have to do is walk to school, which is free and hand these two people which is free and I make money and and so that was really my first introduction. Obviously I’ve learned since then that those things cost time and that’s what the compensation is for. And but it was my way of figuring that out my way of figuring out oh my gosh, these people didn’t pay. Right, so I got 20 people to order a team paid to didn’t and that crushed my profits. Oh my gosh, even though they were only this percentage of my total orders. It still destroyed my profit margins. I had issues with a partner, so I brought him friends to help me sell and they wanted 5050. And I was like, but it’s my idea. I’m the one ordering. How do you divvy that up? What else? What else I learned from that experience? It was boring as the other.

John Corcoran 5:13

You weren’t passionate about it. You didn’t want to make wire answers. You’re, you know,

Dave Selinger 5:18

there’s a cause there. Right? And so we had pinker racer.org. And, you know, we were raising money to save the pinker racers, developing countries. And you know, it just it wasn’t, I, as you said, I wasn’t passionate about it, we would do one order. I think I did sunglasses one time, because Oakleys were a really big deal about 20 bucks, and you could buy, this is just the beginning of kind of Chinese manufacturing sales, you could buy from the same factory as Oakley this same quality and, you know, and there’s no chaos. Right? And, and they weren’t the same quality. It turns out, by the way, yeah.

John Corcoran 5:55

It fell, it fell apart. And then

Dave Selinger 6:00

people demanding their money back. That was that was the less fun conversation to learn about from my peers. So you know, and that’s really one of the key lessons I learned that leads to meet today even which is it if you’re doing something that’s risky, it’s superduper important that you’re either going to make so much money, you don’t have to give a crap about anything ever again, period, or that you really care about it. Right? And those are really the only way two ways make something risky. Makes sense, is that it has to make sense outside of the context of any expected return in its entirety. Right? We’re, you know, something like, you’re going to go buy three lottery tickets and maybe make a billion dollars or whatever.

John Corcoran 6:40

Yeah, so take some big bets is what you’re saying. Yeah. And you must, you know, you end up studying computer science at Stanford. So you must have gotten into computers. At some point, were you ever did you ever, you know, crank out websites for hire, you know, in high school, for

Dave Selinger 6:57

sure. So I mean, I’m maybe a little older than then the website game for some of the young kids. So the internet really didn’t come about until, you know, call it 9596 ish. And I was already in high school at that point. So I didn’t do too much of that. During my younger years, I did do pump pumping out websites in college. So and that was, that was a little bit of a side hustle. I did while I was in school, I did get interested in computers very early, when I was about six, my mom got our first computer, it was a leading edge Model D was a, a 288, I think it was maybe three megahertz. And so I think you could probably cut off a quarter of an iPhone, it would be more powerful than 100 of those things, right? And put that in context. But yeah, I mean, I loved it, I thought that the the concept of creation within the the environment of computers was almost unbounded. You could create a world you could create an environment, you could create a simulation, you could create a model of a house, I remember one of the first pieces of software I learned how to use was AutoCAD. And I just thought that was just amazing that you would come up with an idea for a house and then there it was in absolutely clear green and black right in front of you. If you didn’t get the joke, that’s because the screens were green and black in numbers versions of them that, but I mean, it was really something that captured my imagination. And not just video games, but that again, the act of creating. And so as you mentioned, I then did apply for college and went to Stanford and found that was just an amazing opportunity for me, I look now back at kids that get get to go to Stanford. And I realize I very much took that for granted as Yes, I was lucky. But I mean, lucky in a very, very global sense. Now, the very, very select few get to get that type of an experience. And I feel very blessed for that.

John Corcoran 8:59

It is an amazing university, beautiful campus credible network. Shortly after you graduate, you go to work for Amazon. And you know, looking at your your LinkedIn history here. You were there for a lot of a lot of time. And usually the new kid who just graduated from college doesn’t go straight into inner, you know, meeting and getting mentored by the CEO. So at that point in time, when you first started, what was Jeff Bezos around was the active was he involved was he was he in meetings? What was that experience like around him?

Dave Selinger 9:31

Yeah, I mean, like you said, it was going to right out of school for me, I’d had a couple jobs. So I dropped out in the middle of college to do some startups, and then came back. So I was already 2526 At the time that I joined Amazon. And I’d had some work experience by that point, but not enough to really kind of contextualize the fact that there you are in your first week and you’re meeting with the CEO, as you just said, and he’s very interested in your work and then you’re meeting with him. Every couple of days. He’s critiquing things and providing you direct feedback. And then they actually let my manager go. And that was how I became the manager that division and promoted me to take over that whole division.

John Corcoran 10:12

And what was that conversation? Like, you’re 2526 years old, your manager gets let go. It’s like, guess what kid, you’re in the big leagues now.