Interview with Ben Rubenstein
What Two 9-Figure Exits Taught a Serial Entrepreneur About Investing with Ben Rubenstein
Building a successful company can create generational wealth. But once you’ve had a big exit, figuring out how to invest that money without taking unnecessary risks can be more challenging than many people would think.
That’s why I’m excited to have Ben Rubenstein on the podcast. Ben is a serial entrepreneur, investor, and the founder and Principal of SetPoint Capital, an asset-backed private credit platform and technology company. He’s had multiple 9-figure exits after co-founding Yodle, which sold for $342 million, and Opcity, which sold for $210 million. Today, Ben brings his experience as both an operator and investor to building technology and investment strategies across real estate, fintech, and private credit.
In this conversation, we discuss the lessons Ben learned from scaling and exiting multiple companies and why he believes great businesses are built around customers rather than ideas. We also talk about what separates safer forms of private credit from the risks making headlines today, and how his experience on both sides of the table has shaped how he thinks about investing his own wealth.
In this episode, you’ll learn:
✅ Why Ben uses a barbell approach to investing that combines safer cash-flow investments with concentrated opportunities where he has a competitive advantage.
✅ How asset-backed lending, aligned incentives, and new technology can create additional layers of protection for private credit investors.
✅ Why deep due diligence becomes even more important as investors move beyond traditional stocks and bonds into alternative investments.
Featured on This Episode: Ben Rubenstein
✅ What he does: Ben Rubenstein is a serial entrepreneur, investor, and is Founder and Principal of Setpoint Capital, a technology and asset-backed private credit platform serving the proptech and fintech industries. After founding Yodle, which was acquired for $342 million, Ben founded Opcity, scaling the company to over 500 employees before its $210 million acquisition by Realtor.com. Today, he combines his experience in technology, real estate, and lending to build infrastructure designed to make the movement of capital safer and more efficient.
💬 Words of wisdom: “If you build a product that’s the same for everyone, it’s good for no one.” – Ben Rubenstein
🔎 Where to find Ben Rubenstein: Website | LinkedIn
Key Takeaways with Ben Rubenstein
- Building And Scaling Yodle to a $342 Million Exit
- How Ben Built a High-Performance Sales Organization
- Why Successful Entrepreneurs Keep Building After A Huge Exit
- Turning Lessons From Yodle Into a $210 Million Exit
- Why Great Businesses Start With Customers, Not Ideas
- How Ben Went From Entrepreneur to Private Credit Investor
- Why Private Credit Is Getting a Bad Reputation
- Finding Your Competitive Advantage as an Investor
- Building Multiple Layers of Protection Into Private Credit
- How Ben Invests His Own Wealth
- Lessons Ben Has Learned After Becoming an Investor
- How to Learn More and Connect With Ben
Inspiring Quotes
- “If you want to build something that people are going to follow, it has to be credible. It has to be from people who do it.” – Ben Rubenstein
- “Every business I’ve had, the original idea was something, and then it pivots to something else.” – Ben Rubenstein
- “Do not start a business with an idea. Start a business with a customer and a need from a customer.” – Ben Rubenstein
- “That’s what I look for personally when investing, like how do I have something that everyone in the world doesn’t have access to?” – Ben Rubenstein
- “If you know more than the entrepreneur, well, then that business is in trouble, right? They need to know more than you do.” – Ben Rubenstein
Resources
- Setpoint
- Setpoint on LinkedIn
- Ben Rubenstein on LinkedIn
- Texas Stock Exchange
- SpaceX
- Tesla
- Yellow Pages
- Richard Nicholas Hair Studio
- Stellar
- S3 Ventures
- Bessemer Venture Partners
- Homecity Real Estate
- Uber
- Match.com
- Realtor.com
- Zillow
- Homes
- News Corp
- Rupert Murdoch
- Succession
- Opendoor
- Carvana
- SoFi
- Andreessen Horowitz
- Citibank
- Wells Fargo
- Tricolor
- First Brands
- Homeward
- UpEquity
- Flyhomes
- Icecap Group
- Andrea Propp
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Read the Full Transcript with Ben Rubenstein
Justin Donald: What's up, Ben?
Ben Rubenstein: I'm excited to be here. Thanks for having me. Looking forward to this.
Justin Donald: Yeah, good to have you on the show. We've talked about it for a while, so we've made it official.
Ben Rubenstein: I know. I've been to a lot of your events, met a lot of your team. I'm happy to sit down one-on-one and hang out.
Justin Donald: Well, it's always fun for us. Number one, I love featuring my friends here that have done really cool things. You've clearly done that. We'll get into some of your background. Number two, we have groups that we feel are really important to us as sponsors. You're obviously one of our key sponsors, and we appreciate that, and love all that you're doing with Setpoint, and I definitely want to dig into that while we're here. And you've also been here 15 years. I've been here 10 years. We've seen the Austin landscape change. We've seen who's coming in. I mean, Austin's a totally different city these days.
Ben Rubenstein: It is. Yeah, I've been here 15 years. It's very different than when I moved in 2011. In that time, it was going from kind of a smaller, sleepy town to, okay, this is becoming a real tech hub, more and more product and engineering. I moved here because we decided to make our sales and service hub here. We had over 1,000 people, and we could really hire some incredible talent. Then around COVID, everyone moved from California and New York, and it became a very big place for investment in technology. I was just telling my wife about this recently. I feel like I was more social during COVID than maybe before COVID because of the number of people moving here.
And now, not only do you have the tech world moving here, you now have the finance world moving here as well. Palo recently announced they're having their second headquarters here. There's the Texas Stock Exchange in Dallas, so Texas is becoming a finance hub, too.
Justin Donald: It really is. You've got SpaceX here. You've got Tesla. You've got all these different companies. You've got a bunch of companies that have already announced that they're going to be building huge factories here. Large headquarters, their second headquarters. It's really become the epicenter of a lot going on.
Ben Rubenstein: It's been fun. I've really enjoyed living here.
Justin Donald: I'm glad we're here for it. All right, your background's incredible.
Ben Rubenstein: Thank you.
Justin Donald: And I want to contrast where you were versus where you are because you've been an entrepreneur, you've founded a number of companies, you've had exits, you've had really sizable exits, right? You've had a $210 million exit, a $342 million exit. Realtor.com bought one of your companies, and you were CRO of that company, so on the executive team there for a while. So, you've got this amazing background on that side of being an operator and scaling companies, but you also have a background as an investor and building a fund and doing some things that are way different in the private credit space. So, I want to tackle this, but I think it's fun. And we'll get into why private credit's getting a bad rap, and, by the way, shouldn't be.
Ben Rubenstein: Yeah. Maybe some parts of it, yes.
Justin Donald: Some parts.
Ben Rubenstein: Not all of it, definitely.
Justin Donald: For sure. But talk about some of your earlier career in building companies, and, I mean, these are monster exits. There aren't too many people out there, number one, that have a $100 million-plus exit. You've done it two times over, and you've done sizable amounts.
Ben Rubenstein: Well, thanks. Yeah. Well, my first company I started when I was in college. I was only 21 years old.
Justin Donald: Is that Opcity?
Ben Rubenstein: No, it was Yodle.
Justin Donald: Oh, it was Yodle. Okay.
Ben Rubenstein: Yeah, Yodle. Yodle started… A good friend of mine, his father has a number of different car dealerships in Connecticut. And in the early 2000s, like 2003-2004, his dad put him in charge of the internet stuff. This is the early days. Internet is just like, "Get us a website, see if anybody would come to that website,” which was, again, innovative for a car dealership in the early 2000s. It was the early days of Google AdWords, the very early days. It was called Overture at the time. Yahoo Search Marketing was MSN, later became Bing. And we worked together, and we said, "Well, we can drive a lot of traffic to this website." And if you search for things online, all of my friends I remember in college were using Google and other search engines.
And you'd search and just be national ads for things. You'd see no local businesses. So, that was our theory is that consumers were going to the World Wide Web and nobody would use the Yellow Pages anymore. I remember I was in college, and they would del… I lived in this big building. They'd deliver the Yellow Pages in a pallet. And it would go straight to the dumpster.
Justin Donald: Oh, my goodness.
Ben Rubenstein: Right? And so, I knew my father was an attorney in Connecticut, and how expensive it was to advertise. It would be $10,000 a month to have an ad in the Yellow Pages.
Justin Donald: Yep. You guys are just throwing them out.
Ben Rubenstein: Right. This was a…
Justin Donald: By the way, I think I'm older than you, and I definitely used the Yellow Pages. And as one business trying to sell, like using it as a sales guide for prospective clients and customers and stuff. But then I used it for finding work. I used it for all kinds of stuff.
Ben Rubenstein: Yeah, I mean, it had real utility before the internet, more than just being a booster seat for some kids. Actually, I remember, we made this little ad at Yodle, which was like, "What should you do with the Yellow Pages now that nobody uses it?"
Justin Donald: Oh, that was good.
Ben Rubenstein: Because, again, businesses were spending... It was a 20 billion-plus market, right? And businesses were spending a lot of money in there, because historically, that's where consumers went. But consumers were moving online, and again, consumers move much faster than business owners. You're seeing the same thing with AI today, where consumers are heavy users, and businesses don't really know what to do. And so, back then we said, "There's this big market shift and opportunity." We understand that people are moving this way. How do we capitalize on it? So, 21 years old, I was living in a dorm. I made my first sale the day after graduation.
Justin Donald: That's cool.
Ben Rubenstein: Yep. It was Richard Nicholas Hair Studio, this hair salon in Philadelphia.
Justin Donald: Put you on the map.
Ben Rubenstein: Yes, exactly. His quote was, "It's like taking candy from a baby," really, because we would use these tracking phone numbers, and we could see, like, when you search for a hair salon in Philadelphia, he was the only one coming up. And so, he was getting tons and tons of business from that. And so, I was going door to door to small businesses. I didn't have any money. Every dollar I had, I put into the business, and I was living on an air mattress. I moved every two months with my wife for two years, until we got to about a million-dollar annual run rate. And then we decided to raise our first round of venture capital from a firm in New York, Bessemer Venture Partners. And at that time, the VCs could say to you, "Well, if you want our money, you have to move." So, we moved. I was in Philly at the time.
Justin Donald: Well, they could say, "Here's how it goes at any level, and you just have to do it."
Ben Rubenstein: The world of raising venture was so different back then, right? I remember I'd go in a room. They'd barely pay attention. There'd be someone playing on their BlackBerry. It was before the iPhone. They were very disrespectful to young entrepreneurs because there wasn't many of us. I mean, there was plenty of us and not much money in venture capital. And fortunately, we went with these guys who had a Penn connection, too, at Bessemer, which they were amazing. But yeah, back then they could say, "Okay, you need to bring in a gray-haired CEO." Back then, "You have to bring in... You have to move to do this." And they'd take a lot of your company. Today it's the complete opposite. There's so much money in venture, and there's so few good entrepreneurs out there.
Justin Donald: You have to be competitive.
Ben Rubenstein: Right. That it's all about, like, the founder is very elevated. And the founder has a lot of options, where previously we didn't. But anyway, so raised our first round, moved our headquarters to New York, and really scaled that business over about 10 years. We had about 1,500 employees. We had about 60,000, 70,000 small business customers. We had a huge call center here in Austin of over 1,000 people. We made over 80 million cold calls a year.
Justin Donald: Oh, my goodness. You guys were a machine.
Ben Rubenstein: We called every small business in the United States four times.
Justin Donald: Wow.
Ben Rubenstein: And we had just built this super repeatable process where we could bring in people who they didn't really have any sales experience, and fairly quickly make them super productive, successful, and help them make a lot of money, too. So, I was very proud of all the people in Austin and around the country that we hired.
Justin Donald: And that's where you kind of have to figure out some sort of standardization. Here's the sales script. Here's the objections. Here's how you handle them, right, so that you can train people and actually take someone who doesn't know sales that can quickly become really good at it.
Ben Rubenstein: Well, when you're making 80 million cold calls a year, we have a lot of data, right? We know very specifically when this objection comes up, what is the answer that overcomes that objection, and what the scripting should be. And we had a lot of experience in building scripting. I remember when we first started, we brought all the best sales minds in a room, and we're like, "Okay, what should we say here? What should we say there?" And we built this Frankenstein script. And nobody used it, and it didn't even work. It was terrible. And then the next thing we said, "All right, well, that's not going to work. How are we going to get everyone to say the same thing? How do we know what the right thing to say is?"
So, we found the top salesperson, who everyone wanted to be, who was making the most money by far. And he was doing something very -- he was saying the same thing every time. So, we literally wrote down all the words that he said. I remember it was this one guy. His name was Butch, and he pulled all the recorded calls. He lived in Austin, but he went in a hotel in Austin, and he was there for a week just listening to calls to understand the nuances of the script.
Justin Donald: That's awesome.
Ben Rubenstein: We wrote down word for word what this top sales rep said, and you'd think some of it was a little strange and like, "Why would you say that?" But these actual words made sales. And so, we got a lot more buy-in that they were actually his words. We knew they actually made sales in the past. And so, we became a very, very scripted team, and conversion skyrocketed because of that.
Justin Donald: That's what we noticed. So, I worked with Cutco back in the day, and I learned scripts, and I never wanted to kind of do my own thing until I had a script down that worked, and then I would innovate from there and try and figure out ways to get a little bit higher percentage closing, a little bit higher percentage average order, whatever it is. And so, I do remember at a certain time, our team and our company are under the banner of Cutco, became so efficient, so good that we ended up being the group that was recorded. And our information went out corporately to everyone else to kind of learn how to do it.
Ben Rubenstein: Well, no one's going to just take what corporate tells them to do, right? They're going to say, "Who's successful? And I want to emulate that." And so, if you want to build something that people are going to follow, it has to be credible. It has to be from people who do it. And also, we were hiring people that they didn't have a lot of sales experience, right? So, we had to help them, right? The best people we hired were former bartenders, waiters, people used to making…
Justin Donald: People skills, right?
Ben Rubenstein: People skills and also used to making commission, right?
Justin Donald: That's what you want. You want someone that's hungry, that doesn't want a base pay. They want to be able to make the outlier pay.
Ben Rubenstein: This is a hard job. I mean, you were making 100 calls a day, maybe more, and the best people were making one sale a day. So, you're facing a lot of rejection. I mean, so we nailed it down to there were three personality traits, and if you had these three personality traits, you were going to crush it at this job. But if you didn't, you weren't. And so, really, your resume was kind of meaningless. It was like who you were as a person is what we were looking for.
Justin Donald: So, did you use, like, behavioral or personality type assessments to be able to figure that out? We did that in our company.
Ben Rubenstein: We did a lot of that to understand who our top people were, take that, and use that in the interview process as an initial screen. But ultimately, so the three things were coachability, right? I mean, we had a script that we knew worked. And coachability isn't just saying you want feedback. It's like loving feedback. It's when we give you feedback... And I remember there was a leader in my company who said, "Feedback is a gift, and I have a present for you." When you truly think like feedback is this present that you're being given, you appreciate it, and you're able to adapt and absorb that and change. So, I'd say that was probably the number one.
The second one is work ethic, as you were just talking about there, right? If you make $200 a day and somebody else makes $100 a day, you're going to get there faster even if you're not as skilled. It's just by sheer volume of effort. And the third and probably most important was attitude.
As I was saying, this is a job with insane rejection. Right? I don't know. The exact analogy is, in baseball, if you're a great hitter, what do you hit? Like 300.
Justin Donald: 300, yeah. But you're talking about…
Ben Rubenstein: That means you failed 70% of the time.
Justin Donald: 20%, 25%. 200 calls, one sale.
Ben Rubenstein: One sale. Right? And so, like failing 99 out of 100 times, 199 out of 200 times, you could look at that in two ways like, "Well, I made 99 calls. The next one's going to be terrible." Or you say, "The odds are the next one's in my favor, right? I made 99. Statistically, it's got to happen.” And so, the people who were able to overcome that rejection, were positive every day were the best people by far.
Justin Donald: And those people can go into any industry and they can crush it. I mean, early days for me, I sold newspaper subscriptions door to door. Same thing. You get rejected. Now you get some nasty people that slam doors in your face or won't let…
Ben Rubenstein: It's the worst cold call you think of, right?
Justin Donald: So, it's this, like you build up a callus to know, and you kind of get past the personal nature of feeling like you were rejected. Really, it's like, no, that was just the outcome of what happened here, and maybe I need to improve, or maybe I just need to make more calls. It's a numbers game, right?
Ben Rubenstein: Our number one sales rep when he was early in his career before us, worked at this company where they sold encyclopedias door to door. Do you remember? Do you happen to know this company? The Southwestern company?
Justin Donald: Oh, yeah.
Ben Rubenstein: And what they would do is they'd send somebody into a small town, and the first thing they had to do was find housing, because they didn't provide housing for people. So, they had to go door to door convincing someone, "Can I live in your basement?" And then they would go door to door selling encyclopedias.
Justin Donald: It's intense.
Ben Rubenstein: Most people do not make it in that. But if you're able to make it there, you can make it in anything you do. And that's why one of my favorite question to ask new hires in my company is, "What was the first thing you sold? How old were you? What did you do?” And you learn a lot about people. The paper route or the lemonade stand or whatever they did, and how much did they have to hustle. Because if you didn't have to hustle. Like, you need that early training.
Justin Donald: You need that backdrop. That's right. Yeah. That's awesome. I love hearing that. And you've scaled a number of companies. Okay, so what happened with this company?
Ben Rubenstein: So, Yodle, we expanded across the country. As I said, we had 60,000, 70,000 small business customers, and then we sold for $342 million in early 2016 to Web.com.
Justin Donald: Okay. Another big brand there.
Ben Rubenstein: Yeah, Web.com, they were public at the time. They've since gone private.
Justin Donald: So, help me understand something. I've got to imagine with an exit that sizable, regardless of, you know, and I know. Like I've started a company called Stellar with some buddies, and that did really well, and it's still doing really well, and maybe we end up having a full exit this next year. But we raised money from S3 Ventures and did... So, that was our Series A. Did a Series B, as well. And so, there's some dilution along the way, but at that number, you had to have hit the jackpot, and you could've just mailed it in. So, why not be complacent? Why not just go live life on your terms, live a crazy wildlife? Like, why start the next company?
Ben Rubenstein: Well, I still think I am living life on my terms. I think, when you have it in you, because I know a number of entrepreneurs who've started companies and kept going. When that's in you, and you keep fighting through it, it is part of who you are. You don't really have a choice. Like, it's part of your nature of I enjoy building things. I also thought at the time like, "Man, I've made so many mistakes. I've learned so much stuff. How could I not use this?”
Justin Donald: Yeah. For the next one, right?
Ben Rubenstein: I have this huge network of people I love working with. I've made so many mistakes. I know how to do it better the next time. Like, I'm just going to do nothing and stop? I remember when I left Yodle, I went and traveled with my wife. It was five, six weeks.
Justin Donald: Yep.
Ben Rubenstein: And not that long, and I was like-
Justin Donald: You got to do something. Yeah.
Ben Rubenstein: I got to get back at it, right? Like, there are so many things running around my head, so many opportunities that exist in the world, so much I want to prove. I was saying about Yodle, although I was one of the founders of Yodle, I wasn't the CEO of Yodle, right? Because in those days, we had to bring in some gray-haired CEO. So, I think I had a chip on my shoulder of I can run this whole thing. There was probably one. I think it was, I want to... I just saw all the mistakes we made, and we can do it better.
Justin Donald: Yeah. I love that, and I had my first exit, and it was nowhere close to the size of yours, just for everyone tuning in here. I wish it was. But it was good enough to just give me time. I had a bunch of passive income anyway at that time. We had gotten into mobile home parks and other types of real estate, so my lifestyle income well exceeded my cost of living, right? So, I took a year off, and at five weeks I started getting really antsy. At five months, I started getting really antsy. So, I kept pushing. I had a mentor tell me, "If you can do a year, if you can just push to a year, it's ama… And just say no. Just say no to everyone. It's amazing the doors that will open and the clarity that you'll get."
And so, I did that, and ultimately that's where Lifestyle Investor came from, was that time off and figuring out what I wanted to do next. You were able to figure that out a lot quicker, and I don't know that I had the clarity quite as early as you did. So, talk about this next company.
Ben Rubenstein: Yeah. So, Yodle was online advertising for small businesses, right? Like, we were replacing the Yellow Pages, helping people get a website, get online, social media marketing, reputation management, review solicitation. But what it was, it was a very horizontal product. And that was one thing I realized was, if you build a product that's the same for everyone, it's good for no one, right? You want vertically specific stuff. So, that was one frustration we had. And so, we had pretty high churn because of that. The other problem with Yodle was selling leads to people. If I get a plumber, I promise him 15 leads a month, and you get him 17, well, that's too much. He just quits. If you get him too few, he wants to kill you because you didn't do what you promised. You get him right on the number, that's nice, and they…
Justin Donald: I've something else I want to spend my money on.
Ben Rubenstein: So, churn in SMB was really painful, and selling leads was really painful. So, I wanted to start another business with all that learning. I know how to build a very large call center team. I know how to generate leads. And so, let me pass them to people as referrals and only get paid when they're successful. Let me go into one vertical that I know really well, real estate, right? Residential real estate. Real estate agents pick up their phone, right?
Justin Donald: That's right.
Ben Rubenstein: They publish their cell phone numbers. So, I can get ahold of people, and I can pass referrals. And a friend of mine had started a residential real estate brokerage here in Austin and Dallas. They weren't huge. They were like 2% of the Austin and Dallas market, but they were buying over 40% of the online leads. So, these guys were an online lead conversion machine. So, I said, "I can take what's happening in this one brokerage and scale this out to brokers across the whole country."
Justin Donald: Yeah. This is Opcity.
Ben Rubenstein: This is Opcity, yeah. So, that was the idea for Opcity. Well, actually, the original idea for Opcity was something very different. Every business I've had, the original idea was something, and then it pivots to something else.
Justin Donald: Isn't that funny? Same here.
Ben Rubenstein: Yeah. So, if I was a very early-stage angel investor, my question would be, "I don't even want to know about your business because it's not what you're going to be doing. I want to know who you are," right? Like, "Tell me why you're going to win, and someone else isn't going to win." Also, I don't, and I advise a lot of other entrepreneurs, because they're like, "Oh, I have this idea. Don't tell this person. You need to sign an NDA." It's like the idea is meaningless. Don't start a business with an idea. Start a business with a customer. So, at Yodle, we started the business in the car dealership, right? At Opcity, we started within a brokerage here in Austin called Homecity Real Estate. That was why it's Opcity. Homecity there. And so, we had our first customer that we could really intimately... We were in their office, intimately built for them.
Justin Donald: Except you got to see the behind-the-scenes type of work, right? What they need and…
Ben Rubenstein: Yeah, I remember at Yodle, we bought this company called Lighthouse that did appointment reminders for dentists. I know you have your dentist say, "Your appointment's tomorrow," and then you hit C, and then it writes to their practice management system. The guy who built that, his wife was a dentist, and he built it for her, right? And so, to be great in product, to build a great business, you have to intimately understand your customer. And that customer can't be somebody who's just random business. They're not going to tell you the truth, and they're not going to give you the time to really build the right product. So, we had an embedded customer, which was this first real estate brokerage. I had all this talent that I could bring with me from Yodle.
I had all this understanding of how to scale a large company like this. I knew how to generate leads at massive scale and convert those leads. And so, we had all the right pieces together to build.
Justin Donald: And you had no non-compete, or you just had to wait a certain time to be able to bring the people over?
Ben Rubenstein: Well... Oh, you're saying non-solicit?
Justin Donald: Or non-solicit, rather.
Ben Rubenstein: Yeah. I didn't. Plus, it had been by that point almost, like... So, I left. I then took a number of months off, then had the ideas going. Until we were doing real scale hiring. It was probably about a year by that point anyway.
Justin Donald: Yeah. So, you outlasted it. That's awesome. And so, what ended up happening there? I mean, you had, I think, thousands of employees there too, right?
Ben Rubenstein: Well, by the time, in less than three years, we went from zero to about 500 employees. We had over 100,000 US residential real estate agents on our app. So, the model was, you know how an Uber driver gets a ping on their phone and they know there's a ride. It was very similar, right? It was a real estate agent got a ping on their phone, and they knew we had a consumer ready to talk to them who wanted to go see a property. But at the same time, it was like Uber meets Match.com, right? So Match.com, there's a lot of information about the two people, make a match between the two parties. Uber, it's who's available now, and we were doing a combination of the two. Who is the right real estate agent for the right consumer, made that match, and who is available right now, through our app.
Justin Donald: And how did that company come to exit? What did that process look like? And I've got to imagine you learned a lot through the first exit, to-dos, not-to-dos, just even on that M&A process.
Ben Rubenstein: Yeah. So, our largest partner was Realtor.com. The way our business model worked is we worked with Zillow, Realtor, Homes, all the big portals, and a lot of the inventory that they hadn't sold to other agents as leads, we were able to work and then refer that out to people. So, by far, they were our largest source of revenue. We were their largest partner. So, we got to know them very well. And really a lot of the pitch to them, and them to us is we can help enhance their business model, right? Because their business model was just selling leads. I knew the frustrations intimately well of selling leads, and I said, "Well, what if you can actually make more money and make your customers happier by having a win-win on a success model with them?"
And Realtor's owned by News Corp, so that was a very in, you know, so that's Rupert Murdoch. Yeah. So, it was a very interesting experience of…
Justin Donald: Well, the show, Succession, if anyone's watched that.
Ben Rubenstein: Yes, at the time there was like three or four different shows about the Murdochs, at the same time, happening when I was there.
Justin Donald: Yeah. Fascinating. I mean, if you get behind the scenes there, that's an interesting company and group and family dynamic.
Ben Rubenstein: I spent a lot of time at News Corp in New York. By that point, News Corp and Fox had separated into two different businesses, but it's all in the same building, and I got to watch, I mean, that's a... I had always been in startups, and to move into not only Realtor, which is a larger company, right? They're the second-largest portal in the United States. They have over 100 million unique users a month. It was crazy.
Justin Donald: 100 million unique users a month. That's crazy.
Ben Rubenstein: Yeah. And moving to the CRO role, where now, where before it was us versus the world. Here's, I think, the biggest difference between a small company and a big company. When you're a small company, there's not many of you, and nobody knows who you are or cares who you are. And so, it's you as a team versus the world. When you have something like Realtor.com that's been around for close to 30 years, and everyone knows who Realtor.com is, so you don't need to... I mean, obviously you're spending a lot on marketing, but it's not you versus the world. You have this amazing asset. It's you almost versus yourself of, how do you get this big machine to work with itself?
And you often have some adverse selection is the more entrepreneurial people want to go do other things. And so, the people left are less entrepreneurial people. And so, how do you get that steady Eddie worker group to move things to the next level? It's very difficult in a big company.
Justin Donald: Now with that one, did you not raise VC money?
Ben Rubenstein: Opcity we did.
Justin Donald: You did, okay.
Ben Rubenstein: Yeah. We raised a Series A, where at Yodle, we had raised many, many more rounds because we'd been going a lot longer.
Justin Donald: So, let me ask you this. When you exited both, did you have any sort of earn-out or anything that tied you to it? I mean, I know you did on one.
Ben Rubenstein: Yeah. At Realtor.com, the earn-out was longer than the company existed.
Justin Donald: Wow.
Ben Rubenstein: Like, at Yodle, I mean, Opcity was around for less than three years, and my earn-out was a little more than three years.
Justin Donald: Wow. That's intense.
Ben Rubenstein: But I don't know. I saw the earn-out as like this time. I had a chip on my shoulder of what I could prove. I think all these scenarios are like, I think I could do things better, and so I want to be up to the challenge, right?
Justin Donald: Well, now you have a playground of a much bigger company, a much bigger industry. It's like, what can I do at the top, right?
Ben Rubenstein: Yeah. So, I'm here. It's like, wow, now I have access to this amazing amount of consumer traffic.
Justin Donald: Unlimited tools.
Ben Rubenstein: Tremendous portal. You have so many resources. And I see things are broken all over the place, and I have a point of view of why they should be different. I don't want to just be the armchair quarterback just talking about it. I want to be in the arena and say like, "This is what I think's going to happen, and let me go show you."
Justin Donald: So, this was a $210 million exit.
Ben Rubenstein: Yep.
Justin Donald: Nice payday again. How long did you take between that exit? So, you put in three more years, and it's always harder when you're running someone else's company than when you're kind of building your own. How long until you kind of moved and pivoted to the next thing, which I believe was Setpoint?
Ben Rubenstein: No time, really. Yeah. So, what happened was so I had some cash from Yodle and Opcity, and I'm working at Realtor.com. And while I'm at Realtor.com, I'm meeting all the founders and CEOs of all these really interesting proptech and fintech models. And I started advising some of them, and I started doing some angel investing in these businesses. I joined the board of a few of them. And I then started personally providing debt to them. As a lot of the advice you give at Lifestyle Group, I wanted that steady cash flow of income. My co-founder and I were doing it. And it wasn't direct lending to these businesses. It was asset-backed, so all of the models needed to have... They used, typically, US residential real estate in a bankruptcy-remote SPV. And I really liked this type of lending, saw really high returns. And I was just kind of doing it on the side.
And then I was telling some friends and family about it. Other people got excited about it, and so we launched a fund. And so, this was happening right around the time I was leaving Realtor, and I was like, "Well, I've never really managed a fund before or managed other people's investments at scale. But man, we have something, and we have a real competitive advantage of understanding this space."
Justin Donald: That's right.
Ben Rubenstein: But at the same time, because again, I'm coming from a tech company background, I see I'm operational in these businesses, and I see, whoa, these guys, where most people are underwriting these deals, they're looking at consumer default or what's going to happen to price fluctuation of properties. I see a risk that other people don't see, which is I'm in operations in these businesses, and these guys are buying and selling assets of real estate daily, and the tracking is horrific. Everything's tracked in email and Excel. They'll fund with a thumbs up in Slack, right? There's fat-fingering happening here or there. And I was like, this... And because I'm new-ish to the type of lending, and we're not doing it at massive scale yet. And there's not a better system to track all of this?
Justin Donald: From a systems guy.
Ben Rubenstein: Right. Yeah.
Justin Donald: You know, built successful companies based on that.
Ben Rubenstein: And especially you see there's been so much innovation on the front end of fintech, right? I don't know, Opendoor in housing, Carvana in auto, SoFi in student loans, right? There were all these big companies being funded to solve this consumer problem. But then there's the back end of fintech where all the money comes from, with all the banks and private credit funds and LPs, and that's all very manual, because nobody had invested anything there. So, we said, "Oh, wow, this is an interesting opportunity, not only to solve a problem for ourselves, but to solve a problem for the larger market." And that's when we launched Setpoint Technologies, which is software for originators of loans and their source of capital, which are typically big banks and private credit funds.
Justin Donald: And, by the way, this technology company is really, I believe, what kind of created your moat in the space, right?
Ben Rubenstein: Right. So, it's this wonderful, symbiotic nature of the two, right? It feeds the credit fund origination opportunities. It makes it so we can do the high-velocity funding that we do, where we're funding multiple times a day, where others can't, so it gives a real competitive advantage in that. It makes our capital much safer because we understand what's happening within an originator. So, it does all these wonderful things, and at the same time is a software company that's very needed in the world. We raised our first round from Andreessen Horowitz. We then raised our Series B from Citibank and Wells Fargo. And now we're in most of the large private credit funds, many of the big banks. Like, it's a really important piece of infrastructure we are building, which makes capital move easier and is safer, and thus brings down the cost of capital for everybody.
Justin Donald: Well, it's kind of like that dentist that built the technology for their own practice, and then it ended up becoming huge, and they kind of white-labeled it or sold it as a service to other people. You did that same thing with your technology moat, right?
Ben Rubenstein: Because we were our first customer.
Justin Donald: So, you proved it on you, and now everyone wants it.
Ben Rubenstein: You got credibility because you're like, "Well, you're a private credit fund. I'm a private credit fund. We're the same, right? Let me tell you my problems. We built something for it. Would you like that as well?" And so, yeah, that is kind of what I preach to people is do not start a business with an idea. Start a business with a customer and a need from a customer. Yodle, Opcity, Setpoint have all been built because there was a customer pain that we were intimately involved in and can iterate very quickly with that.
Justin Donald: And let's talk about private credit now because recently it's gotten kind of, you know, it's been dragged through the mud a little bit with, there's some groups that are doing more risky type of loans to companies. And then there are other private credit that is going to be more collaterally backed, right? And so, there's a big difference here in the two, and I'd love for you to kind of explain that, because what you're doing is different than the profile of what people would say, "Oh, that's really risky in private credit."
Ben Rubenstein: Yeah. Well, I'd start with scale is the enemy of alpha, right? If you have massive amounts of money to deploy, it is very hard to generate alpha in a lot of money, right? If you have so much money, you make more money on the management fees than you do on the carry. And so, you are incentivized just to deploy money, not necessarily to make money. Especially because it's such a long time horizon, no one's even going to know, right? You just deployed the money. I mean, I'll go back to the Yodle story from 20 years ago. Back then, venture was a cottage industry. There was not that much money in venture. So, they could treat the entrepreneurs however they wanted. And they had their pick of the litter and took a lot more of companies.
And guess what? Their returns were really, really high. What's happened over the last few years, there's so much money in venture. These are massive funds, and they make a lot of money on management fees. But they have to deploy a lot more money, but the number of entrepreneurs hasn't changed that much. And thus, the terms they're getting are much worse, and thus, their returns are going to be much worse.
Justin Donald: Yeah. And it's a longer hold, so they're getting fees for quite a long period of time.
Ben Rubenstein: They are, and there's not a ton of accountability there. Private credit, something similar happened where you had... Private credit was not this gigantic of a space, and then you had all this money pour in.
Justin Donald: Yep. Trillions of dollars. It went from nothing a decade ago to trillions of dollars. A few trillion dollars.
Ben Rubenstein: And so, when you're one of these funds that has so much money to deploy, you're going to start... You got to put it into something, and you make riskier and riskier decisions, or you go higher up the tree from the low-hanging obvious fruit. And so, what happened was a lot of these funds, they started to do a lot of direct lending, which is just lending to businesses based on with no actual assets behind them. And these businesses were ripping, and so everything looked good. And then you had the SaaSpocalypse and other things, and the value of those businesses went down significantly. And they had no collateral, and they had a lot of debt. You marry on top of that, they had all these redemptions at the same time, right?
Because it used to be in private credit, or you see in venture and private equity, these are closed-end funds. So, they'll have highs and lows, but there aren't an opportunity for everybody to take their capital out. Then people got spooked and started all taking their money out at the same time, which creates this kind of snowball effect of…
Justin Donald: Yeah, it's like a bank run.
Ben Rubenstein: Yeah, it's a bank run. But they have gates and hurdles, which makes people who felt like their capital was liquid realize it's not actually liquid. So, that is kind of what's happened in the backdrop of a lot of direct lending, which private credit is the overarching bucket, but direct lending is where I think a lot of the news has been. One other thing that happened in private credit recently was, I don't know if you've heard of Tricolor and First Brands, but there's been a lot of fraud in private credit. Because, as I said, there's not a lot of infrastructure. There's not a lot of tracking. So, you'd have somebody like Tricolor double-pledge their assets. They'd have one facility that they had pledged the cars to, and then have another facility and say it was the exact same cars, right? That's fraud.
Or you'd have others who would manufacture invoices or alter invoices, right? And nobody was tracking, and there's no way to know. So, you have massive funds with pressure to deploy, bad deployment in direct lending, like with no collateral, you have fraud, and you have kind of the run-on-the-bank redemptions, which led to lots and lots of news. Fortunately, what we're doing is like different than all of this, like every one of those.
Justin Donald: Well, your niche to me is the most unique I've ever seen in private credit, so that's why I'm excited to kind of dig in.
Ben Rubenstein: Well, that's how you make money is having something. You have a competitive advantage.
Justin Donald: That's right.
Ben Rubenstein: If you are trying to do something that everyone can do, there's not that much of an advantage to it. Like, I'll say something that's controversial. I don't do much in Bitcoin, for example, right? Because I have no competitive knowledge. Somebody does. I don't. No structural advantage in any way, no hookup with anything in any way. So, doing something that everyone can do, I'm not going to be able to generate alpha on any of that, right? So, that's what I look for personally when investing of like how do I have something that everyone in the world doesn't have access to? And so, I did, right? Because of all of my network of the proptech and fintech customers, I had that. Because of our technology, we are able to lend in ways that others can't.
And so, we're never the cheapest source of capital, but they're more sufficient for our borrowers, which has been how we've grown. But with this niche strategy, our fund is a $500 million fund. We couldn't deploy 3 billion-4 billion, and we're not trying to deploy 3 billion-4 billion in this fund, right? We know what we're good at, and it's our own money. We have $43 million of our own money in this thing. I'm not going to…
Justin Donald: That says a lot. For me, as an LP, it's important that I know you as the GP have a lot of money in, that you have skin in the game. So, like that gives me a lot of confidence that, hey, you're going to do what's best. I know you, so you're going to do what's best for your clients, your LPs.
Ben Rubenstein: No, but our incentives are aligned.
Justin Donald: But your incentive, yes. We are very aligned.
Ben Rubenstein: Yeah. We built this for ourselves, right? We built this for our own capital, for our own family offices. I make more money on the interest on my LP position than my GP position.
Justin Donald: Wow.
Ben Rubenstein: Right? I mean, I'm doing it for the LP position. And that's why we've brought friends and family to be part of it. But by it not being massive amounts of money, we're able to maintain this niche strategy. So, I think that's one. We are not an AUM shop. We pretty much make no money on the fees. It's like keeping the lights on. And we only make money when there's carry, right, when we actually generate returns. It's all asset-backed, right? So, obviously, we underwrite our borrowers. We want them to be healthy and standing, to be good businesses. But if something were to happen to them, we still have the asset, which is US residential real estate, single-family residential real estate held in a bankruptcy-remote SPV that we control.
Justin Donald: Yep. Huge.
Ben Rubenstein: So, asset-backed is super, super important. And in terms of fraud, I mean, we are the software. We are the cops. We're the ones who are providing software to prevent fraud to the big banks, to the private credit funds, right? Had those guys used our software, maybe these big fraud events wouldn't have happened.
Justin Donald: That's right.
Ben Rubenstein: And so, we have a huge competitive advantage in safety too, because we are building the software for it.
Justin Donald: And so, when I think about some of what you do in your business, is it HomeAway? Is that one of the…
Ben Rubenstein: Homeward is one of our borrowers. And I'm on the board of Homeward.
Justin Donald: Yeah. And so, for anyone that has ever wanted to buy a home and you're having a hard time selling your home, or the dates don't line up, you have this company that you then can borrow from, close on this home. Whenever you sell your current residence, then you kind of take care of that, you pay some interest, and you win. Everyone wins. It's a brilliant thing, and I love that you guys are some of the financial backing to that company and others like them in that space, in that proptech space to be able to help people.
Ben Rubenstein: Homeward, UpEquity, who's based here in Austin, Flyhomes. There's a bunch of these different models out there, and I'm very passionate because there are so many people who want to move, who need to move, who can't, right? Because of friction that doesn't exist in any other purchase that you make.
Justin Donald: Yep.
Ben Rubenstein: And your home is the biggest financial decision most people make in their entire life and making that an easier process. I mean, I know many people who've... They own one house. They have to move. Maybe they're in the military. They have to move. Maybe there's a death in the family. There's a new birth, and they need an extra bedroom. There are just so many. Maybe you have a new job.
Justin Donald: Come back to work. You got to go to the office.
Ben Rubenstein: Come back to work. Right. You have to move closer. There are so many reasons people need to move and often don't necessarily get to pick the timeline in which they're going to move.
Justin Donald: So, you could sell a home in a bad market, right? And have a hard time selling it.
Ben Rubenstein: Right. And so, what happens is, so if I want to buy another house, right, especially your average American, 99% of people cannot buy their new house with cash. They just don't have that cash lying around. But they also can't get a second mortgage, right? Because they have the mortgage on their first house, and no one's going to give them another mortgage because their debt-to-income will be too high until they get rid of this mortgage. So, it's this terrible chicken-and-egg thing, right? So, what most people do is make a contingent offer, contingent on selling their first house.
Justin Donald: Which is a weak offer. Yeah.
Ben Rubenstein: Now, as the seller, I don't want that contingent offer, right? So, I'll take a cash offer any day of the week. And so, if I'm the contingent offer, I'm going to either lose or I'm going to have to overpay for my house. I'll have to offer more and not be able to negotiate with the seller anymore. And it seems wrong that people who have less money have to overpay for their houses. Like, just because of this timing and structural imbalance.
Justin Donald: But that's the reality.
Ben Rubenstein: Well, but that's why 8, 10 years ago, a lot of these new models came up, the Homewards of the world, UpEquities, Flyhomes, that have said to consumers, "We will solve this problem for you. Pick out the house you want. We will buy it with our cash." Consumer then moves into that house. They then help them sell their old house in the open market, and they have more time to sell that house. And so, they can buy their new house for less, because they're a cash buyer and sell their old house for more.
Justin Donald: That's right.
Ben Rubenstein: We love this model, because we are financing the power buyers, the proptech companies who are doing it, that it's super prime consumers. Average FICO score is 750.
Justin Donald: Nice.
Ben Rubenstein: These are people who've been living in another house, paying their mortgage, qualify for this. It's all positively selected properties and assets. So, that's another thing in asset-backed lending. It's, well, what are the assets? And if you had to liquidate them, does anyone want them? These are homes that required a cash offer to win. If it was some junky home, you could've done the contingent offer. It wouldn't have even mattered. So, they're positively selected. And these are well-funded, venture-backed companies that we require have enough of a big enough balance sheet.
In our model, six of our borrowers through the seven years we've been doing this have ultimately wound down their business, either gone out of business or shut down this line of business. In every one of those situations, we were fully repaid, without even having to go to the collateral, because of all the layers of protection we have at the borrower level.
Justin Donald: As an investor, I love that.
Ben Rubenstein: We've been battle-tested.
Justin Donald: It gives me a lot of peace of mind.
Ben Rubenstein: Yeah, I think a lot of people have funds…
Justin Donald: You've got three different layers of protection, as I remember from just talking to me about it before.
Ben Rubenstein: Yeah. Well, the first layer of protection is the corporate counterparty, right? This is the power buyer, the venture-backed company who has a big enough balance sheet. We require them to have typically 12 to 24 months of runway. And if they ever get to six months, 6 to 12 months, we stop funding and unwind the facility.
Justin Donald: Okay.
Ben Rubenstein: We have really aggressive advance rate step-downs. So, if the property itself is not selling, our advance rate on that property goes down through time, so if anything's going wrong there. We have a separate reserve account where they have three to six months of interest. We can sweep their operating account. So, we have a lot of controls in place that if something goes wrong, we'll be fully repaid there. But if for some reason that borrower spends 12 months of runway in a day, we have, as you're saying, the second layer of protection, which is that super prime consumer who put 5% down and is living in a house. And if all of them went away, we have the US residential real estate at a very low advance rate that's positively selected. So, the model is…
Justin Donald: It's a brilliant model.
Ben Rubenstein: And I was saying we've been battle-tested, right? I mean, we've lived through COVID, where lots of people lost their jobs in a short period of time, and the credit markets froze up. And our only exposure was the homes that were purchased the 60 to 90 days before that. Then we had the run-up of housing prices, which completely threw the real estate market into a tailspin. Then we had interest rates tripling from 2%, 3% to 7+%. And a lot of our borrowers couldn't raise equity in 2022 and 2023, which was very stressful for them. And recently we thought that there was going to be more interest rate cuts, and that hasn't necessarily happened.
Plus, there's not enough inventory in the United States, which has really locked up, and people are stuck in 2% to 3% more. So, there's been a lot of turmoil in US housing, and throughout that, we've maintained our returns and have had zero loss, and our borrowers have been very healthy.
Justin Donald: Yeah. And as an investor with you, I can vouch for that, which is awesome. Like, I feel so good knowing all these backstops that you have and the control. You basically have the hammer, or you get your claws into the collateral. So, in a worst-case scenario, you've got a few different tiers here, but in a worst-case scenario, you're coming out positive.
Ben Rubenstein: Yeah, and that's why private credit, back to your question before, it is a big bucket. And I think a lot of it, asset-backed private credit has done very well. In credit, when things go well, you make money. When things go poorly for your borrowers, you often make more money. And your IRR is even higher because of all the protections and what you're sweeping in. So that's why, to me, asset-backed real collateral is very important.
Justin Donald: Well, I had Andrea Propp with Icecap…
Ben Rubenstein: She’s awesome. Yeah.
Justin Donald: …on one of our previous episodes, and she's a member, and we love her. We love her company, and she sponsored our Napa trip last year.
Ben Rubenstein: She is so awesome, yeah.
Justin Donald: She's just a blast, and so we really dug into private credit. But I believe you're the person that introduced me to her.
Ben Rubenstein: I did. Yeah.
Justin Donald: And I'm so thankful for that introduction.
Ben Rubenstein: Well, she lives in Austin, and so we were just talking about power buying, but we also lend capital to originators of RTL loans, fix and flip loans. And she's in that RTL world. So, I was like, "You are raising money from LPs in RTL and live in Austin? There's not many of us. We need to hang out."
Justin Donald: That's right. That's right. So, that's awesome that we've been able to really dive into private credit, with both you and her, and for our audience to get a chance to understand the nuances and intricacies in how do you do it safely versus what's risky. So, I appreciate you sharing that.
Ben Rubenstein: Well, both she and I, like a lot of people want exposure to real estate, but they don't want the headache of managing real estate. Like, if you own a bunch of properties in Austin, you could get a return, but you got some work. You've got to go find tenants. You got to either hire a property manager or do the property management. Owning real assets is work. And if you're trying to get passive income, but you like the exposure of US residential real estate, because you know it's really safe, there are other opportunities to do that without having to do all the legwork.
Justin Donald: Yeah. Well, I'm excited to talk to you about your life on both sides of the table, right? So, you've been this operator and founder, and you've scaled companies. You've had exits. You know that side of the world. But you've also now been on the investment side of the world, raising funds and with your own funds in it, right? And so, I'm curious, as you think about both sides, what do you think is the better opportunity? Is it starting and scaling a company? We know the odds are super low over there, but if you hit it right, you can make a ton of money, or investing, and investing in great funds and finding a way to earn a return there. What do you see as the better way to earn a living, the safer way to get a return on your investment, whether it be time or money?
Ben Rubenstein: Well, better's hard because I think you actually got to separate out time and money. So, I'll start with just how I think about my own money and wealth, and then I'll next go to how I think of my own time, which I think there's some conflict in there at times. So, I try to treat my portfolio like in the barbell approach, where I'm doing some very, very safe stuff. So, we'll talk about the credit fund, where it's all asset-backed, where it's real-time passive income, where I feel very confident that I'm not going to lose. But you're not going to have a huge winner there either. Nobody's getting completely rich off of the private credit returns. It's just nice, steady, healthy income.
Then the other side of the barbell is something I also control, which is a tech company, which is an illiquid asset that I don't know if and when there will ever be an exit on that. But if there is an exit, it'll be much, much larger. But it's risky, and I don't know what it's going to be. And so, I think where people make a mistake is they try to do things in the middle, where it's kind of risky, but not that big of an upside, and you think it's liquid, but it's not really liquid.
Justin Donald: Or you don't know that it's risky. We see a lot of people in that space, right? You think, "Oh, shoot, I just lost all my money. I didn't realize this thing that I was doing was that risky."
Ben Rubenstein: And there wasn't even that much upside in the first place.
Justin Donald: Yeah, right.
Ben Rubenstein: Right? So, that's why I really like the barbell. Part of your money is in incredibly safe stuff that you know nothing's going to go wrong, and the other part is in risky stuff that you can influence, that you have unique access to, that maybe somebody else doesn't, and you can shoot for the moon. So, I'd say that's how I think about money management. In terms of time management, some of this is kind of who you are, right? So, I remember leaving Opcity, and I was thinking at the time, "Well, I could have 50% of a new company if I start it." Or maybe I could have 5% of 10 companies." I still get to that same number, but I'd have more diversification if I have 5% of more companies.
It seems a little safer if I have 5%. And I could still maybe get the upside on those companies, but I have 5% of them. That was my theory. So, I started doing some in, as I was saying, angel investing in these companies. I joined the board of some of these companies, and I got really frustrated. Really frustrated, for a few reasons. One, in VC, if they have one grand slam out of 10, they've returned the fund. So, 9 out of 10 things can fail, and they make money. But what you don't realize is that means 9 out of 10 of their boards are failing.
Justin Donald: That's right.
Ben Rubenstein: Nine out of ten of their businesses, something's going wrong with. And so, when I was doing this in angel investing, I found the companies that are doing well, I'd talk to them sometimes. They didn't really need me. I could be helpful here and there. But, man, the companies that were having problems…
Justin Donald: They need you all the time.
Ben Rubenstein: Oh my God, they were sucking me into everything. And it was clear that, one, they weren't listening to me, but even if they did, this thing wasn't going to turn around. And again, that's the law, the power law. Most things don't work out. So, with your time, most of the companies you're working on are losers. And that started to bother me. Then it was, I'm used to asymmetric information where I know much more than my investors, right? And I like that position that... And when you flip to the investor side, it's all about pattern recognition. But if you know more than the entrepreneur, well, then that business is in trouble, right? They need to know more than you do.
And so, I didn't love the dynamic of knowing less, not being in as control. And even if I was making money, most of my time was on broken boards that needed a lot of my help. So, I don't know if this fully answered your question about kind of my journey.
Justin Donald: Well, I like you dissecting this. Very interesting.
Ben Rubenstein: But I like the barbell approach for my own capital, but I enjoy operating my own fund, operating my own tech company much more than maybe diversification over many.
Justin Donald: So, what did you believe about being an investor before you were one that maybe you learned some things as an operator, founder, having exits, but now as an investor you're like, "Oh, that wasn't true," or, "Oh, it's really like this, and I had no idea"?
Ben Rubenstein: I thought being an investor was much more glamorous than it was. It was like, "Oh, these guys, look at them. They got all this money. A lot of it's not even theirs. They get to just decide what to put in." It turns out it's a lot less glamorous. You know a lot less information. And I think another thing I thought was it's good to diversify and put in a lot of things, but by its nature, if you are diversifying, investing in a lot of things, you don't have as much information on any of those things. And so, I don't think I appreciated, until I ran a fund and even invest my own money, the importance of deep due diligence, like how much work it is. I remember when you guys were diligencing Setpoint, you had two different companies doing the diligence who weren't even talking to each other. I don't even know if they knew each other.
Justin Donald: They were doing it intentionally.
Ben Rubenstein: You had multiple background checks. Like, the amount of time, collective time that was spent in diligencing Setpoint was really intense. And it's worth it for you as Lifestyle because it's not just one check you're writing, it's about a lot of people's checks. But as an individual, I don't have that time or money or resources to do that deep diligence. And so, as an investor, I knew people who were angel investors spreading money all over the place, and that, I've learned, is very, very risky because you're not doing the diligence. You just can't. You don't have the time to or the resources to do it.
Justin Donald: That's right. Or even the abilities, right?
Ben Rubenstein: Yep, the abilities and maybe the desire. It's a lot of work.
Justin Donald: It's daunting.
Ben Rubenstein: And so, it's like, "Whoa. I thought I made all this money so I didn't have to do this stuff. And now it's more work than running a company. So, at that point, I might as well run a company."
Justin Donald: That's right. Well, and this is why I love Lifestyle Investor for our members. We're spending $300,000 to $350,000 a year vetting the deals, vetting the sponsors, doing background checks. We have a couple of different groups that dig in, as you said. And I want both of their... I don't want them to communicate. I want to hear what each of them have to say about a deal. So, we get a chance to kind of understand the process, the different processes, and then the end results. I think that's good, and I just always want to keep our due diligence teams honest. And so, we hear all the time, "Your due diligence is one of the deepest dives, if not the single deepest dive we've ever had from the sponsors that we work with. And I'm very proud about that, and it's awesome to see. But for our members to then invest in those companies, get great returns, get the cash flow that they want, it's a really fulfilling experience for me.
Ben Rubenstein: It's very important. Look, if your members didn't have Lifestyle, they would still invest in things.
Justin Donald: That's right.
Ben Rubenstein: I don't know what. They would invest in something, and they wouldn't be able to do that diligence because that diligence only works when you're doing it as a collective, that someone has enough money and resources to be able to do it for a large group of people. So, I think it's very… Alternatives didn't used to be hot, right? It used to be, oh, just put it in stocks and bonds, which was safer for your average person who didn't have tremendous amounts of wealth. Once you start going the alternative route, the whole world opens up. And everyone thinks, "Oh, I know this. I know that." And you don't. You really need to do insane diligence. So, you need to do it yourself or have a lot of money or join something like Lifestyle who's going to do that for you.
Justin Donald: Yeah. Well, it's been awesome having you on the show, having you part of our community, getting a chance to do life with you. We appreciate you and sharing some wisdom.
Ben Rubenstein: Yeah. I'm so happy we got connected, and we hang out, and we're here in Aus- Austin's a great place. I hope more and more members move here.
Justin Donald: I do too. I do too. So, where can we learn more about you, Ben, and more about Setpoint?
Ben Rubenstein: Yeah. So, Setpoint, you can go to setpoint.io. You can reach out to me. I'm ben@setpoint.io, or Jeremy on our team, jeremy@setpoint.io. Through the Lifestyle community, all of our contact is there. We have a discount for Lifestyle members because you guys have come in as a collective, so please reach out there too. And I'm hopefully super accessible, so if anybody wants to talk or meet up for anything, feel free to email me and reach out.
Justin Donald: Well, we appreciate you working with us and giving us some awesome preferred terms as Lifestyle Investor members. And I'm excited for more people to experience some of the cool stuff that you're up to. But appreciate you joining us here today.
Ben Rubenstein: Thank you, yeah.
Justin Donald: I love ending every episode with a question for our audience. So, my question, my desire, my hope is: what is one step you can take today to move towards passive income and move towards living a life by design? So, most people are living a life by default. What does it look like to live a life of intentionality, doing the things that you want to do, living life on your terms? And what's something you can take from Ben today to help you move in that direction? Thanks so much, and we'll catch you next week.
Ben Rubenstein: Yeah. Thank you.
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