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“There is no algorithim in the world that can replace the relationship between two people.”

— David Lyon

This month’s Winners of Wealthtech interview is with David Lyon, CEO of Oranj, a Chicago-based provider of digital technology solutions for financial advisors.

Here are a few of my interviews with previous winners:

• Brian McLaughlin, CEO of Redtail
• Angela Pecoraro, CEO of Advicent
• Eric Clarke, CEO of Orion Advisor
• Cheryl Nash, President of Fiserv Investment Services
• Bill Crager, President of Envestnet
• Lori Hardwick, President of Advisor Innovation Labs and
• Aaron Klein, CEO of Riskalyze

I was inspired to start this series by one of my mentors, Tim Ferriss, who is a best-selling author, incredibly successful investor, entrepreneur, and podcaster. Actually, Tim doesn’t know that he’s one of my mentors, since we’ve never met. But his work and his writing have been a big influence on me, so I’m going to keep saying it until he tells me to stop. (By the way, I highly recommend Tim’s latest book, Tools of Titans, which you can buy online or even in a brick and mortar bookstore.)

The feedback on this series has been overwhelming! If you have a suggestion for someone you think I should interview, please send it to me at craig@ezragroup.co.

Now hit the Play button!

Complete Episode Transcript:

Craig: Welcome to this episode of the Winners of Wealthtech series on the Wealth Management Today podcast. My name is Craig Iskowitz and I am your host today. I’m a strategy and technology consultant, I work only in wealth management, and I’m doing this podcast to help bring information to industry and share some of the trends and ideas and cool stuff that I’m finding out there in my travels. This Winners of Wealthtech series brings interviews with people I’m excited about and people I think have brought a lot to have the industry. Today’s interview is with someone I have wanted to speak to for some time: David Lyon, the founder and CEO of fintech firm Oranj.

I’ve written a lot about Oranj on my blog, you can check that out at wmtoday.com. David is the founder of Oranj, they have an RIA tech end-to-end platform for advisors. Before David founded Oranj, he was an RIA himself for 10 years. He grew his firm to over 300 million in AUM and wasn’t happy with technology out in the market, so he built his own. He eventually sold that firm and started Oranj in 2014. But even more interesting than that, David’s got a fascinating background. I’m going to tease you a little bit here before the interview, I don’t want to spoil it..

Welcome everyone to the Winners of Wealthtech series for the Wealth Management Today blog. I’m your host, Craig Iskowitz. I’m very happy to have as a Winner of Wealthtech David Lyon, the CEO and co-founder of fintech firm Oranj. Welcome David.

David: Thanks Craig, thanks for having me.

Craig: I’m so glad to have you here. I know we’ve spoken a lot in the past, and I’m glad you had the time to make for this interview and to be on the Winners of Wealthtech. We really appreciate it. We’ve got so much to discuss, besides all my list of questions and your career, where you’ve gone and how you got to where you are today, I really wanted to jump back in time and go all the way back to your first job right out of college. You were a double major at Ohio Wesleyan University in economics and journalism; why did you pick those, and how did you move from that into your first job?

David: Economics was something I grew up with. My father was a large-cap value manager, so I kind of grew up within the industry. Every Sunday we would have a Dr. Lyon’s Learning Academy, and we would read the Wall Street Journal from front to back. We started to get into stocks probably when I was about 11, so I kind of grew up in and around the industry.

Craig: That’s great. Did he have a Ph.D.?

David: No, he had an MBA. He wasn’t an actual doctor, it was more of a play on his sense of humor than anything else. But every Sunday we would do that, that was a big part of growing up in our house. So I think that was my natural passion, going into college. By about my junior year, I was pretty well on track to take all of the required courses for my major in economics and I picked up journalism as a second major, just because I’m really passionate about writing. And something I wouldn’t tell the folks at Ohio Wesleyan, but it was an easy major to tack on to my education. So that’s pretty much how I got to there.

Craig: I love that your dad did that. How did you approach that as a kid? I know most kids don’t really enjoy reading the Wall Street Journal. How did he get you to do that, and how do you make it interesting for you?

David: I’m the oldest of five kids, and he would use as part of his research, to find out what we were interested in. He always did a really good job of turning investing and learning about companies, and translating that into things that we were interested in. So we weren’t diving real deep into financials. I think the first stock that I bought was Chuck E Cheese, and I wanted to know more about Chuck E Cheese outside of the robotic characters and ski ball, and things of that nature. He did a really good job of connecting the dots between stuff that we were interested in and skills that he felt were important for us to have as we were growing up.

Craig: That’s great, it’s great to have your father that involved in what is going on with you. Some fathers are too busy working to deal with their kids.

David: Yeah, he taught me a lot about how to split between being a father and a role model, and going to work every day and working really hard, and how to balance those. I try to emulate that every day; I have two young daughters that are 9 and 11, so a lot of the things that he taught me, I’m trying my best to pass on to them as well.

Craig: That’s all we can do, is try our best. So you had a very interesting first job, I think a lot of kids out of college would relish a chance for this, at least a lot of guys I know. Your first job was with the Chicago Bulls. How did you get that job?

David: I got that job purely out of luck. I was a senior and I really felt like my path was going towards being a junior analyst at a large investment firm, so those were largely the jobs that I was applying for. I got a job offer from Goldman Sachs to be a junior analyst and an analyst-in-training. I also basically took the alumni book from Ohio Wesleyan, and for those that don’t know Ohio Wesleyan is a small liberal arts school in Central Ohio, just north of Columbus. I grew up in Chicago and I knew that no matter what, I wanted to be back in Chicago and live in the big city and experience that as a young professional. So I went through and I highlighted every alumni member from Ohio Wesleyan that was listed in our alumni directory, and I sent them my resume with a cover letter. In particular, I noticed that there was one alumni member from our school that was working for the Chicago Bulls. And growing up in Chicago and being a massive Michael Jordan fan, it would have been the dream job, right? Being able to go to work at the “House that Michael Built” every single day. And I didn’t care what I did, but that was a dream of mine. My basketball skills weren’t good enough, so I figured maybe my education might serve me in some way that I could help the Bulls.

Craig: And that was in 1998, so the beginnings of the internet; no LinkedIn, you actually had to go to the paper alumni journal, pull people’s names out and type them real letters. Right?

David: Oh yeah. In college, I didn’t even have a computer my senior year. You had to go to the computer lab to type up papers and I had an email address, but I don’t think I really used it all that much. It was snail mail, print out the resumes, send it to them, go in for an interview. Basically the program was you come in, you start in June, the season’s over, the Bulls just won their fifth championship. And it was like a casting call; you were in a lobby with hundreds of applicants, and they were all trying to get an unpaid internship for the summer. They had just worked their way through four years of college, and they were all willing to come and work for the Bulls for free for four months, for the shot at getting a full-time job. So that’s what I did. I’ll never forget my first day, they hired 15 summer interns and our sole job was to renew season ticket holders. Which wasn’t really that difficult of a task, it was more administrative than anything at that point, because the Bulls were the hottest ticket in the world at that time.

Craig: Oh, exactly. Yeah.

David: Back to your earlier point about email and computers and internet, we were given a pad of paper, a list of the clients, the White Pages, a phone, and we were told to go and sell.

Craig: The good old days, like a boiler room brokerage.

David: It was similar to that. I think we had slightly higher ethics than some of the boiler rooms of the 80’s and 90’s, but it was a similar culture of, “go out there and just get it done.” There was no high tech approach to it, there was no marketing automation; it was reach out to people, have conversations, develop relationships, and get it done.

Craig: That’s awesome. Do you have any great stories from your time there?

David: I have so many great stories, I’ll tell you two quick ones. When the Bulls were on their sixth championship run, pretty much everyone knew that this was Michael Jordan’s last hurrah with the Bulls. The owner of the Bulls flew down the entire front office to Utah for game six of the NBA Finals. They chartered a United Airlines plane, flew us all down there, put us up, and we got to see Michael Jordan hit the game-winning shot to beat the Utah Jazz in game 6 of the finals. He still went on to play another year with another team, but that was an amazing experience.

Craig: That doesn’t happen very often, that’s a once in a generation event.

David: Yeah, it was a great experience. The second pretty cool thing that I got to do was go to Michael Jordan’s retirement announcement, the press conference. Being a lifelong, fanatical Bulls fan and an even bigger Michael Jordan fan, that was a pretty amazing experience as well.

Craig: Indeed. But even being a lifelong Michael Jordan and Bulls fan, you still felt your time at the Bulls was up by 2000, and you moved on. So why that direction, to Clear Channel Entertainment?

David: Yeah, it was really just looking around. My boss at the time, I knew that I wasn’t really going to be able to get his job anytime soon; I wasn’t really looking either. A young company by the name of SFX Entertainment was coming to Chicago, and SFX Entertainment was a company that was led by a radio tycoon by the name of Robert Sillerman. He went around and bought up all these radio stations, entertainment properties, concert promoters, sports agencies, you name it. He pretty much overnight formed the largest live entertainment company in the world, that was putting on more events than Disney was. They were recruiting people who were working for local entertainment companies in Chicago, and I think that was where I first got the entrepreneurial bug.

David: I thought it sounded pretty amazing, I wasn’t qualified for the job that they wanted to give me, but I felt like it was a good career move. They were going to give me a ton of more responsibility, and I would be able to do things professionally that I wasn’t going to be able to do with the Bulls. I took that job and about 10 months later, SFX Entertainment got sold to Clear Channel Communications, which was the big radio conglomerate outdoor advertising, and we became the entertainment division of Clear Channel. That’s what brought me into that world, continuing within the same industry but expanding the skillset. I was able to tap more into my economics background, where at Clear Channel I was helping different business units monetize each other’s assets. They had outdoor advertising, radio, motorsports, athlete representation, concert promotion. And live music.

Craig: Everything there was back then. No streaming video or media, it was all actual, physical entertainment.

David: Absolutely. And at that time, part of what I was doing was a concert would get booked, they would promote it and three months later you would find out how much money you made. And part of the problem that we were trying to solve (and I was a part of) was that Clear Channel is a publicly traded company. So how do they project revenue out for this company that they just bought? They bought SFX Entertainment for $4 billion. How does that not become a hindrance on their stock price when they can’t project revenue out more than three months, for something they spend $4 billion for?

Craig: Yeah, you would think they would have that under control.

David: Yeah, and they didn’t really have that figured out. I wasn’t the sole point person to help them figure it out, but I was part of a team that tried to help them figure it out. And after six or seven years of Clear Channel trying to make that marriage work between their radio division and the live entertainment division, they decided that the entertainment division would be better off as their own company. So they spun off our division, which became known as Live Nation.

Craig: I forgot how that worked. So then they became Live Nation, which is this huge conglomerate of concert promotion.

David: They’re really a multimedia, multi-content medium company today. They’re probably generating 50% of their revenue off of their streaming content; you’ll see content that they have on Netflix today. I was there at the infancy of that movement, but it was a tremendous experience and really taught me how to build a business; everything from marketing to sales to operations, and how all those pieces fit together was a tremendous experience for me. I got to be a fly on the wall during the spinoff and the IPO of Live Nation as a publicly traded company, and watched how they reinvented their business model to be a more viable, publicly traded company.

Craig: Do you have any cool stories from entertainers, hob-knobbing with rock stars, or were you just stuck in an office on the phone all day?

David: I have a lot of stories, I’m searching for which one would be most appropriate and politically-correct to share.

Craig: It’s very different in the wealth management and technology industry, the people who were willing to versus when you’re promoting concerts.

David: Yeah, yeah. I got to meet plenty of entertainers and musicians and bands; I got to meet Mary J Blige and Sheryl Crow, but I wasn’t on the front lines with the talent. A valuable lesson and experience that I had was with Guns N’ Roses. I forget what year this was, it might’ve been 2005 or 2006. Guns N’ Roses was coming back on their big comeback/grand finale tour. We had done a deal with Accenture to be the title sponsor of the Guns N’ Roses tour. Kind of an interesting brand fit, but nonetheless we went out for the opening night at Madison Square Garden.

David: All the celebrities were out there, it was a big ticket item in New York City. We’re sitting in a skybox waiting for Guns N’ Roses to take the stage; an hour goes by, two hours, three hours. Then the manager comes on the stage and says the concert has been canceled because Axl Rose had a breakdown and he won’t come out of his room. And we’re sitting there in a box with corporate executives from Accenture who wrote a seven-figure check to sponsor this tour. So that was a real lesson, from a business standpoint, in how to manage clients when you’re not able to deliver.

Craig: Seriously. That’s about as big of a failure to deliver as you can get.

David: I think more than that, the lesson is that there are things that you can control in business and there are things that you can’t control in business. It’s about how you pick up the pieces and move on, and you still find a way to deliver that value to clients. It ended up working out really, really well, we were able to deliver a tour sponsorship to them with Billy Joel and Elton John, which was probably a better brand fit for Accenture than Guns N’ Roses Comeback Tour was, but it worked out. It was a very difficult situation and I learned a lot from it. I don’t think that was the exciting artist story that I think you were looking for..

Craig: No! I was expecting, “I went to the hotel room, they trashed it. They knocked the walls down. We were partying until 3AM.” None of that though, right?

David: No, I was never cool enough to be invited to those types of soirees. But I certainly got to meet a lot of really interesting, famous people so it was a great experience.

Craig: You mentioned how you learned about how to deal with clients when you can’t deliver. How has that experience changed the way you manage at Oranj?

David: I think every entrepreneur is going to say under promise and over deliver. But I think largely what that means at the root level is to really think about what you’re taking on, and to be emphatic about planning. I don’t know if that approach would have put us in a better position with Axl Rose and Guns N’ Roses, but going back we could’ve done a better job of trying to position them into a different tour. And I take that back to what we’re doing today, and looking at realistically how can we deliver on new features that advisors are requesting, or new business initiatives that we have as we want to grow and continue to grow our business? It’s really about right-sizing those opportunities and putting a plan together that everybody is invested in, to be able to deliver that. But certainly don’t promise people things before you know you can deliver on them.

Craig: That’s very well thought-out advice that any firm could use, in my opinion. So after 8 years the Live Nation, how did you make the decision to start Main Street Financial?

David: That was a big leap for me, going from the live entertainment business to starting an RIA. In like 2005 my father was diagnosed with leukemia, and it really upended our family. I became more involved and had to be there for my mother, and also help them with their finances. I knew pretty much what I needed to know, from an investment perspective, but there were so much more than that. We were dealing with life insurance and their monthly expenses and things of that nature. And my mother was really not equipped or educated to deal with that stuff, as my father was going through treatment. During that time I discovered a passion for helping people with their finances, and was able to educate myself in areas I wasn’t educated in. Things around life insurance and medical expenses and all of that. My father ultimately lost his battle with leukemia in 2007.

Craig: I am sorry to hear that.

David: Thank you. It was tough. We’re very, very involved, myself and Oranj as a company; we give back to the Leukemia Lymphoma Society and we’re involved with a couple other charities as well. That was really an inflection point for me, where I was about to become a father myself; my wife was newly pregnant when my father passed away, and I did a lot of reflecting. At the same time, my mother really needed a lot of help as well. So I said, “If I don’t do this now, if I don’t go off and try to start my own business, when will I ever” And it wasn’t the most ideal time..

Craig: It is never a good time for that.

David: Yeah. Going off and starting your own business and becoming a father at the same time is pretty challenging.

Craig: It’s scary, yes.

David: It is very scary. But I knew that the passion that I had for this, and being able to afford my family (primarily my mother) and the ability for me to help her and then grow a business at the same time, was a calling for me. I started my RIA in 2008, which was also an interesting time to go off and start an RIA. So that’s pretty much how I made the leap there.

Craig: You didn’t pick that time, it just happened to you.

David: Yeah, yeah. People always say things happen in threes: between the recession, my father passing away, and me becoming a father, it was kind of that factor of three. I was fortunate to be able to build a business in something that I was really passionate about doing.

Craig: Do you think the recession helped you, considering what the business was and that a lot of people were afraid to invest on their own after that?

David: I do, I think there were two things as I look back on what helped me grow that business. One was hard work. The second was that there was a feeling from do-it-yourself investors that weren’t prepared for this, and I think there was a growing demand for someone to have a personal trainer in their life. But I also think because I did choose the route to independence and I chose that RIA route. I think a lot of investors were really disenfranchised with the larger wirehouses that were showing up and testifying in front of Congress every month; they were really questioning the intention and ethics of a lot of the larger institutions.

Craig: Yeah, on the one hand it was a terrible time to be in the market, but on the other hand it could be a good time to hang out your own shingle as an advisor.

David: Absolutely.

Craig: So that was successful, I imagine. I know the last time I interviewed you for my blog (about 4 years ago) you told me the story, but tell me the story again about how you came around to the idea for Oranj.

David: Where it really originated was, what was my core value proposition going to be as an advisor? How was I going to hold myself out to clients and prospective clients, and what did my service model look like? Largely my story was that, I’m going to do things for my clients that they just don’t have the time to do themselves. And that story really resonated with a lot of the clients that I brought on early on. I didn’t have any book of business, but I was fortunate that I had a pretty large natural network. There wasn’t mad anything magical that I did, outside of a really high level of activity, to build that book of business.

David: I was fortunate to grow my AUM pretty quickly within a two year period, and going through that type of growth I was really able to see where the holes were in my business. And it wasn’t so much back-office facing as it was front-office facing. I was really good at getting referrals, and I was tracking that and looking at the fact that I was only meeting with a small percentage of the referrals that I was getting. In order for me to continue to grow the business, I had to get better at having a lot of those first meetings. If I was able to get those first meetings, my ability to bring on and acquire new clients was really good.

David: So it was about being able to demonstrate to prospective clients the value that I can provide, but more importantly, what it was like to work with me. At this time robot advisors were starting to pop up; Uber, Amazon, Netflix. There was so convenience being created through technology, and I was looking at what I was doing, how I was connecting with prospective clients and how I was serving existing clients. I was looking at my business model and my workflows and processes and saying, I’m in the stone age. I’m asking clients every quarter to meet with me for 90 minutes, then we do the big bang annual review, and people just weren’t living their life like that anymore. I really felt like I needed to have technology as part of the service and value that I provided that help people’s lives be easier, not more difficult. And that was what paved the way for me to conceptualize Oranj, that’s pretty much how the idea and the concept came to fruition.

Craig: That’s really interesting. I love to hear how those sort of ideas percolate and come out and then how they actually take shape and get executed. Because that’s also a pretty big change for you, from a financial advisor into running a technology company in effect. You really changed what your business is. You’re still helping people, but it’s a very different service model, providing software versus providing financial advice.

David: Absolutely. I’m glad that you mentioned that, because that is exactly how we feel here at Oranj. We view that we’re helping people through experts and professionals that care about their clients, and are there to serve their clients and help their clients achieve their goals, and help them make smarter financial decisions. Anything that we can do or any software that we can build to help facilitate that relationship is core to our mission.

Craig: Indeed, I’m sure your clients appreciate that. So moving from your history and how you got to where you are.. This is where I start asking questions more about you and how you see the world, and how you see business beyond what we just spoke about in your career. At this point in your life, what’s become more important to you in your personal life over the past few years?

David: It’s definitely the time that I have with my family. When I first started at Oranj, there was about a two-year overlap where I was running an RIA and also building a technology company at the same time. And I missed out on a lot of events and special moments with my kids, and I had a real challenge and difficulty in trying to balance that, and knowing when to hit the pause button on my business to make time for my family.

David: Over the last few years, I’ve gotten much better at that. Part of that’s been, as the company’s grown, there’s other people to do many of the things that I was doing and many of the hats that I was wearing. But it’s definitely making sure that I hit the pause button. Every night I’m home for dinner with my family, unless I’m traveling on the road, which I manage much better today than I did a couple of years ago. I need to be at home for dinner with my family; it really helps me to stay centered and understand what’s the most important thing that we’re doing here. I think that’s probably the most important thing that I’ve been able to change over the last few years.

Craig: I’m glad you did that; I feel the same way and did that myself. I’ve got three daughters, so I know what position you’re in. You see as a change in how you approach things, how you feel, how you deal with stress when you’ve got that family time. You don’t realize how important it is when you’re just grinding it out of the office 20 hours a day.

David: Yeah, 100 percent.

Craig: I want to take a little break from this episode to talk to you about one of my favorite sponsors, the Invest in Others Foundation. Invest in Others is a non-profit, you can find them at investinothers.org, and they look to raise money and give out awards to charities that are sponsored by financial advisors. So it’s financial advisor’s favorite charities and charities that they spend a lot of time supporting. So Invest in Others looks to get sponsorships from the industry and funnel that money to advisor’s favorite charities. I really like this charity and this non-profit, I think you should take a look at it. Again, investinothers.org. They’ve got a couple other programs; one is a Grants for Good program, again delivering money to different needy organizations and needy groups. They’re also starting a corporate awards program, which is going to be a little bit different but still within the industry. Another way for financial services and wealth management corporations to help donate money to people in need. I really like Invest in Others, I think you should take a look at it. Investinothers.org

Craig: With your success and how well things have gone (you’ve been running Oranj for five years now), how do you stay motivated and keep that entrepreneurial spirit going?

David: That’s a great question. I think two different ways. One is the people that work at Oranj; the opportunities that we’ve been able to create for everybody that works at Oranj keeps me motivated. I’ve always felt that in starting a business, what was core to my mission was building a company with really great people who are passionate about what we’re doing. That whatever business that I created, that we’re able to help people grow personally, professionally, and financially. That, in a nutshell, is what keeps me motivated and keeps my entrepreneurial spirit going. Once you start to build the beginnings of that, you’re able to start to see everybody else take on that entrepreneurial spirit and them start to come up with the ideas and the direction of where they want to take things. Whether that’s a feature or whether that’s a way that we want to service advisors better than others out there in the space, that is definitely what keeps me going.

Craig: So you’ve made your entrepreneurial spirit contagious, so everyone in the company catches it?

David: Yeah, we try really hard to do that. I think we’ve created a pretty good culture; we never sit back on our laurels, we’re always trying to find new ways to make our culture better. I don’t think that you’re ever done with that. Everybody here has a sense of ownership of what they’re doing and what we’re building. We release software every week, and we have a company-wide meeting where our product team displays to everybody what we’re releasing that week. And everyone in our company goes to that; our accounting manager, our operations director, marketing, sales, development. Everyone stops what they’re doing, and everyone has insight and feedback for what we’re doing. So that’s pretty special and something that we’re really proud of.

Craig: In your approach to business and your strategy, is there something that you believe that you think other people in the industry might disagree with, or even think is crazy?

David: I don’t think that there’s anything that we do that people think is crazy. That might be a strong term, but our business IS going against the grain, in terms of our business model. We’re providing free software to advisors, and we’re trying to adopt a business model that others within our industry haven’t adopted, we get that feedback a lot. Our goal is to build the highest quality, world-class software, and provide the best service that we can. We want to be the leaders in that, in the industry; it’s what we aspire to every day. I think in order to do that, you’ve got to look at who the best is. We want to build a company, and we’re working towards building a company that is really modeled after some of the leaders in the technology industry, not just within financial services. Companies like Adobe, Dropbox, and Evernote, just to name a few. Part of our philosophy around that is that critical mass is key to building good software, and that’s why those companies have been able to build such great software platforms in such a short amount of time.

Craig: Is there something specific about those company’s software that you’re trying to emulate, or the way they’re directing their strategy?

David: I think each one has its own unique focus around that. I think what Adobe does really well is they give people what they want and what they need, and they allow people to grow as their needs change. I think something that we’ve seen is that advisors in our industry will license technology, but they’ll only use a small percentage of the features in that technology. And that’s not a great feeling as a consumer, no matter what kind of dollar value you’re paying for the software or any type of product or service for that matter. So from that aspect, I think we really look to Adobe. Dropbox, they’re continuing to grow their features and evolving into other avenues and feature sets. But at the heart of what Dropbox does really well, is it just works – and it works really, really well. I think our thesis on that is that they went to market, they let millions and millions of users go in and use their software and that’s how they got to where they are. They weren’t really looking at each user and saying, how do we monetize each user? They were looking at, how do we grow and build a really good software platform, that a lot of people see a lot of value in? They decided they would figure out how to monetize and grow it after that critical mass, and we’re largely taking the same approach.

Craig: With that approach and with your company growing, adding more clients, and becoming more successful, how do you identify people that will be a good fit at Oranj?

David: People who want to join our team?

Craig: Correct.

David: I think finding the right fit for employees and people that want to join our team is really hard; there’s countless books about it. I think that the more complex you make your hiring process and your evaluation of talent, it lends itself more to the analogy of “paralysis by analysis.” We try to boil it down to something that I think is pretty simple, which is we want to hire people who are smart and get things done. And I think if you find a good group of people who are passionate about their careers and who were smart and get things done, you’ll find the right people. There’s plenty of people out there who have really great resumes, 10 years of experience, but their hearts are just not in it; they don’t want to move at the pace that we want to move at. They’re probably not a fit, but people who are smart, people who can problem solve and connect the dots and just work really hard to get things done, you’ll end up with a really good team.

Craig: Yes you should. In your travels and meeting with people and hearing what’s going on, do you hear any bad advice that’s being given out a lot? If so, what would that be?

David: Something I hear that I think is bad advice is largely relating back to an old way of doing business, where a lot of business owners are looking at each relationship as their own separate P&L, and how do you monetize each relationship that you have? I think that that generally is bad advice, I think it often steers you into making bad long-term business decisions, and you end up not having as much flexibility in your business, ultimately to grow it. That’s what sticks out in my mind when you’re asking me about bad advice. The best companies that we’ve seen in the last two decades have grown their business by not thinking about monetizing each relationship and they think about things from a bigger picture view. The world has changed; we’ve got Warren Buffet out here telling all the Berkshire Hathaway investors that Berkshire has to change the way that they find value in the market. It’s no longer about price-to-book value, it’s about companies who are spending money on R&D to find the next value companies. And I think that that is true to how you need to grow your business, and you need to spend money to create a good culture and work environment, and spend money in ways that I think many businesses haven’t in the past.

Craig: What would your close friends say that you are exceptionally good at?

David: If I had to put words in their mouth, I think they would say that I’m good at connecting the dots; looking at what’s going on over to the right and what’s going on over to the left, and finding a way to make everybody meet in the middle. My friends view me as a connector and a solver of problems, so I think they would say that I’m good at connecting the dots.

Craig: That seems quite valuable, especially in this day and age where networking is so important.

David: Absolutely. It’s all about relationships, and I think that that’s really an underpinning of what we’re doing at Oranj. Not to bring this back to Oranj, but there’s no algorithm in the world that can replace the relationship between two people. And that’s why we’re building technology to help connect people and to help solve problems.

Craig: That’s a continuation of what you’ve been doing in your career, solving problems in different ways. So in your career, with all of the different careers you’ve had, they say that we learn more from our failures than from our successes. Do you have a favorite failure that you learned the most from?

David: There’s so many of them, I couldn’t even count. Way more failures than successes, and I think anyone that tells you otherwise is not being honest with you. I have a lot to choose from. Growing up, my passion for the Bulls didn’t start when I was working there. I was a 12-year-old who thought he was going to be the next Michael Jordan, but I was a terrible basketball player. There wasn’t a sport that I didn’t want to play. I remember having a conversation with my father and he told me, just pick one. Don’t play four sports, pick one thing and be really good at it.

Craig: Parent should do that today. I’m sure you see, parents who think five sports are good for their kids.

David: Yeah. The kids are way over-programmed today, and it’s a challenge. I remember I had failed miserably playing basketball, and one day driving home from one of the games I was about 14 and my dad said to me, are you sure you really like basketball? It was his indirect way of saying, pick another sport. And he was doing it in a very nice way, but it took me a long time to figure that out. Once I did, it was a really valuable lesson. I think all of your failures together is what would be my favorite failure, because you draw on those failures constantly. And I think having the mindset that a failure isn’t a failure, right? It’s not leading you to the glass is half empty, it’s leading you to the glass is half full. With each failure, you’re that much closer to achieving the goal that you want to achieve. I think that’s the most valuable thing that I learned from all of my failures; the way to think about it, to internalize it, and to not let it slow you down, deter you, or get you down in any way.

Craig: Good advice, you have to stay focused on where you’re going. Do you give out books as gifts, and if you do, what’s the book(s) that you have gifted most often?

David: I love to read and I think it’s an invaluable part of continuing to learn and to grow, and to adapt and apply other people’s thoughts and knowledge. I think the book that I’ve gifted the most is “The Intelligent Investor,” because I think most people believe that investing is some unknown science, that you have to have some advanced degree to know how to invest. I think that there’s some general guiding principles for that, but I also think that whether you do it yourself or you work with an advisor – I always believe that you’re far better off working with a personal trainer than you are at doing it yourself, but you still need to be educated about the general principles and the building blocks of investing. And, you know, I think everybody should read that book.

Craig: And who is the author of “The Intelligent Investor?”

David: The godfather himself, Benjamin Graham.

Craig: The godfather, that’s a good one. Any other books, or is that the main one?

David: I think that’s the main one. I also love to read biographies. Walter Isaacson has a great biography he wrote about Abraham Lincoln. I also like to read other people’s stories, Andre Agassi has a great biography. His life was a real struggle from when he was a little kid, and I think there’s a lot of really good life lessons to be learned in that book as well.

Craig: Those are all good. Is there a favorite app that you have found recently to be really helpful or make you more efficient?

David: Slack. It hasn’t been super recent, but without Slack I’m not connected to what’s going on in our business. It’s a huge efficiency tool within our business; it connects sales to marketing, to product and development to our business operations. Everybody can have a pulse on what’s going on in the business on a daily basis, just by using Slack. They’ve really changed what used to be pretty static, rigid processes within a business, and they’ve made it more dynamic and agile, to where you can react to things as they’re happening in real time. It’s an invaluable tool, I think it’s probably the most valuable tool that we have at our company,

Craig: Yeah, we use Slack at my company as well. I remember when I first started using it, I felt that I traded my one email inbox for 95 smaller inboxes.

David: There is a little bit of channel management that has to go on, it can definitely get out of control. It’s not just great for business, but it’s also great culturally. Something that we really try to promote within our company is having people being able to share their interests and funny little things that they see going on in the news, or whatever it might be. Every interaction internally within our company doesn’t have to be about bringing a new client on board or a new feature release; you want your team members to interact with each other on a personal level as well. So it’s also good for that.

Craig: I find It’s hard to find the balance between technology interaction or face-to-face interaction. People in the same room will be texting each other or sending Slack messages to each other, rather than picking their head up and talking. So you have to find that good balance.

David: Absolutely. That’s why we don’t have any walls in our office. There’s really no place to hide, but you do that through other things too. You want to make sure that you’re getting the team together for social opportunities as well, whether that’s a lunch or a happy hour, whatever it may be. Yeah, it is definitely a balance.

Craig: What is the most recent social event that the Oranj team has been at?

David: Well, two people in our office are expecting babies.

Craig: Mazel tov!

David: Thank you, these are the first Oranj babies. So we had a big event, a dual baby shower. We surprised them with their spouses coming in, and we got them a diaper cake with their own pairs of Oranj sneakers.

Craig: Was it a cake made out of diapers, or a cake in the shape of a diaper?

David: It was a cake of actual diapers. So much has happened since I had children, right? No one was having gender reveal parties or giving diaper cakes, but that’s the thing now. So we gave them diaper cakes (actual diapers) with some onesies, and we gave them their first pair of Oranj sneakers.

Craig: The Oranj sneakers! That’s become a symbol of your company.

David: Yes, everybody at our company gets a pair of Oranj sneakers. Our motto is, “stay calm and run Oranj.” We’ve built the brand around “run Oranj,” and that’s parlayed into sneakers and all kinds of other fun stuff that we make a part of our culture. But that was a really fun event, it was a great time to take time out of our business and celebrate family. Everybody here is in the office more than they’re at home with their family, so we like to take time out for that. Aside from that we do lots of other fun events together throughout the year. Every summer Lollapalooza, the three-day music festival, takes over Chicago and we take off the Friday of Lollapalooza and we all go as a company.

Craig: Is that because of your Live Nation days, that you instituted that? Are there any other companies doing that that you know of?

David: I’m sure there are some other companies doing that, I hope. It’s a great opportunity to get out of the office, and I believe that music is the great connector. It’s something that we do in the office as well. It is a little bit about my background in the music industry, but it’s more about all of our team members being able to share what they’re interested in. And so three days a week we have a record player, we have a huge record collection in our office, and our employees get to play records in the office. We also do tie it back to our business, because the music industry has gone through a tremendous transformation over the last 20 years. And our industry, the financial services industry, is really in the early innings of that transformation. So we really use music as a way to help everybody here understand what it is that we’re doing, and what our mission is. Which is to continue to help people make better financial decisions in their life, they’re just going about it differently. Working with an advisor is better than not, and we want to use technology to help bridge that gap in the same way that the music industry used technology to further their mission and provide artists platforms that they wouldn’t have had otherwise.

Craig: David I’ve only got two questions left, but first I just want to thank you for being so patient with me, for answering all my questions and for being on the show. So the last two questions I have for you: one is, is there a quote that you live your life by?

David: A quote by the infamous Mick Jagger, from The Rolling Stones. In the song “Ruby Tuesday,” Mick Jagger said, “Lose your dreams and you might lose your mind.” I think back to when I decided to go and start my own business, that was a dream that I had and it was very, very difficult; it’s still very difficult, no matter how many milestones you hit. But don’t ever lose sight of what your dreams are.

Craig: That’s a great quote. Now I’m drawing a blank, I was trying to come up with my quote. My favorite Rolling Stones song is “Gimme Shelter.”

David: I love that song.

Craig: I’m into the in-depth background to music and how things were created, so I’m always reading up on how the artists created the song and how they built it or crafted it, or the musicians who helped them on that. It’s an awesome song, but no good quotes from that. Unless, “War is just a shot away,” but that’s not a great quote for living your life by.

David: Might apply to other things, but not to live your life by,

Craig: Still a great tune. And looking back, if you could send a message back in time to your 25-year-old self, what would that message be?

David: I would say to take more chances. I always had the bug to be entrepreneurial and start a business, I just wish I would’ve done that earlier. I remember back to when I was putting in my notice to leave Live Nation, and I was terrified; I couldn’t sleep. I had a mentor who’s still a great friend and mentor of mine, and she told me, what’s the worst thing that could happen?

Craig: Yep.

David: If you don’t succeed, you either decide to start another business or you go back to work for some other big company. Right. I wish that I would have taken a chance a little bit earlier, but I don’t regret the path that brought me here.

Craig: Yeah, that’s great advice for your 25-year-old self. I’ve heard that before, that thing about the worst case scenario. The worst case scenario is it fails, and you go back to working for another big company. And oftentimes thinking through your fears helps you realize that they’re not so bad, and you should go ahead and take that chance.

David: Absolutely. I think at least now today, the younger generation has a lot of examples of that. When I was 25, there weren’t too many examples of younger professionals out there blazing a trail the way that they are today.

Craig: It’s a brave new world, Dave.

David: Absolutely. If only we had a time machine, right?

Craig: Speaking of time, our time is just about up. This has been a wonderful conversation. I’m so happy you were able to make it and that we could coordinate this and get this on the podcast. So thank you very much for being here with me.

David: My pleasure, I enjoyed it. And the next time that we’re in the same city we should talk more about our favorite songs and the origins of them, I would love that.