Winners of Wealthtech

#WinnersOfWealthTech Ep 6: John Michel, CEO of CircleBlack

“You have to be true to what makes you excited to get up in the morning.”

— John Michel

This month’s Winners of Wealthtech interview is with John Michel, CEO of digital advice technology vendor CircleBlack. John is a serial entrepreneur with a long history of building successful businesses and innovating in financial services and wealth management.

Here are a few of my interviews with previous winners:

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

Now hit the Play button!

This episode of Wealth Management Today is brought to you by Ezra Group Consulting. If your firm is evaluating new technology or looking to improve your current wealth platform, you need to contact Ezra Group. Don’t spend another day using technology that doesn’t offer an elegant user experience. Your advisors and clients deserve better and you can deliver it to them with the help of Ezra Group.

Topics Covered in this Episode

  • How John’s military background shaped his future experiences [04:30]
  • Why he chose Merrill Lynch to begin his career [07:40]
  • The infancy of the online advice world [11:35]
  • What gave him the impetus to start Bullrun Financial [26:10]
  • The “Starbucks Effect” and early content marketing [43:00]
  • How John shifted into starting CircleBlack [46:46]
  • Why CircleBlack was self-funded [50:20]
  • What has become most important to John in his personal life [54:30]
  • Thoughts on universal service to country [1:07:30]
  • How to identify people who are a good fit for your firm [1:11:00]
  • The people he thinks of when he hears the word “successful” [1:16:00]
  • The personal failure he learned the most from [1:20:00]
  • Messages you would give to his 25 and 35-year-old selves [1:24:00]

Companies & People Mentioned:

If you are interested in more information about some of the topics John and I discussed, these blog posts would be useful:

wealth management consulting

Complete Episode Transcript:

Craig: This episode of wealth management today is brought to you by Ezra Group Consulting. If your firm is evaluating new technology or looking to improve your current wealth platform, you need to contact Ezra Group. Don’t spend another day using technology that doesn’t offer a seamless user experience, your advisors and clients deserve better and you can deliver it to them. With the help of Ezra Group Consulting.

Craig: It’s a pleasure to be here with you and thanks for joining me on the wealth management today podcast. This is your host Craig escorts and this episode is part of my Winners of Wealthtech series and it’s the first interview that I also recorded as a podcast. I’m sure you will enjoy it. You can find the transcript of this interview on my blog The Winners of Wealthtech is a special series where I interview leaders of the industry and disassemble their habits and traits that enable them to achieve their levels of success, as well as extract nuggets of wisdom and best practices that they can share.

Craig: And today on the Winners of Wealthtech, I’d like to welcome John Michel, the CEO of CircleBlack.

John: Glad to be here.

Craig: I’m so happy you’re on the show. And you know, we’ve, we’ve spoken in the past and we traveled in the same circles and I’m really excited to talk to you and sort of get into your background and history and share this with our listeners.

John: Well, that’s great. I look forward to the opportunity.

Craig: So doing some research on you and doing some reading. I wanted to go back in time. I’m sure a lot of people talk to you about CircleBlack and Bloomberg. I want to go back to earlier than that and talk about West Point. Local people in our industry don’t come from you think that the elite of the financial services are furnished technology. A lot of it’s Ivy League type of people. I didn’t go to the Ivy League, so that doesn’t affect me. But you can add it from a very different angle.

Why did you choose to go to the US Military Academy?

John: I think I was employees from an early age. I always had an interest, but I also think that service is really important in this country. And there were very blessed and I saw that even more when I was in the military and other parts of the world. And I, I don’t think people realize what a great thing we have here. And unfortunately you people have to step forward, whether it’s in the military or whether it’s you know, helping people out in health or other things. I think, I think service is an important thing. And it was something that I, I really wanted to do. And I also wanted to one to make sure that I didn’t at some point say, Gee I wish, I wish I could have done that. So I had the opportunity. And, and it was it was a great experience for me. I would say my son went to the naval academy and when I told him before he went, as I said, it’s a, it’s a great place to be from. It’s just not a great place to be at. So and I would say that about west point they, they teach you a lot, you learn a lot, but, but you, it’s definitely not a college experience.

John: I mean, I think that they they’ve been at it for 200 years plus, and I think they’ve learned their craft well and it’s designed to get you down to your inner core and your, your basic values and sort of have you understand who you are. And I think frankly, being an entrepreneur you know, has been a, it was a useful experience because there’s a lot of times where you just have to go forward and that you know, that early training has been helpful

Craig: 30 years ago, almost 40 years ago. That, how that helped you shape your future, your later experiences.

John: Well, again, I think it, I think it just, you get a sense of who you are and what you want to do. A, I think it was it’s great to get to lead men you know, at an early age you get a lot of leadership experience. I think that was useful. I mean, it, it’s not from a technology point of view we were, we were extremely advanced and the one hand m one tanks on the other hand the my computer programs were in Fortran and with punch cards. So I’m not sure, I’m not sure how much it prepared me for the technology world of today, but I just think that that leadership experience, the ability to focus on a mission and goal and accomplish them and that ability to realize that good and bad things happen and you just have to work through them. It was good training for me. Yeah. We joke about that. And one day a year, the army navy game, we were always very competitive, but he was a, he was a world class crew rower and actually competed that handily. And navy has a very competitive crew team and he’s actually in the navy hall of fame for the, for their boat were undefeated when they went to Emily and a west point. It was only club sports that sort of tip, the balance in and where he went.

Craig: Interesting. How those, the small things change a lot in your career.

John: It is. And again, I think, I think what I most appreciate about services I said is take that he actually, I was, I was fortunate to serve during the Reagan buildup years and so I never saw combat he, he served, he was actually the first class that went in after 9/ 11. And so he did, he did to kind of combat tours. And so I respect, respect what he’s, what he’s done for the country.

Why did you join Merrill Lynch and how did that change your career trajectory?

John: Two things. One is interesting when you’re leaving the military, a lot of people want to give you an interesting jobs, leadership jobs. But often when the sort of operation bent and I had always been interested in finance, I’d actually run the Investment Club at West Point when I was there and just always had an interest and I had gone to, to help pay my way through graduate school. I had gone and gotten a securities license and actually worked in one of the early sort of independent operations at a company called Anchor National quote, open an office, whatever that meant in in Pittsburgh sort of a one man person. I learned, learned a lot of things about that part of the business. But in particular, when firms were coming to recruit at Carnegie Mellon, Merrill Lynch came. And like most of my contemporaries or the time we all thought investment banking was the way to go.

John: And I met with the recruiter for investment banking and Merrill, and he looked at my series seven license and the experience I was having. And he said, hey, I have a good friend who works in national sales organization at Merrill Lynch and I really think you should talk to this guy. It turned out to be Bob Silver, who ultimately was the number two it at Paine Webber under Joe Grant. But anyway, so I came to, I got based on that experience, I ended up doing a summer internship for Merrill works for Bob and Joe Grant. Oh, by association. And then and then ended up getting an offer and coming back to, to Merrill Lynch and, and was just a great experience. I mean, from my perspective, that culture, that mother Merrill Culture that people refer to, it was really sort of magical. And you know, there was this Lani, Stephen’s was there and when Smith and guys like that and you know, this focus on the customer and bringing main street, I mean, bringing Wall Street to main street was, was really people a embodied that in some regards. You know, it’s a, you always look back in the past and think you know, sort of, there’s always this kind of idea that things were better back then or whatever. And I don’t know that there were better, but it was a great culture and a great place to work.

John: It was a lot of fun. We I got I was fortunate, I got some early experiences and I think I did pretty well. And so I asked him, I got to run the, their retirement plans business and then build a couple of new business, including their online Maryland’s direct and and the thing that we originally called the investment center. And then ultimately those things became combined into what now is Merrill Lynch Edge. Those were the early predecessors.

Craig: You’re following my script perfectly. You’re coming from the military and you’re moving into Merrill and you’re, you’re getting seeped in this culture, which unfortunate doesn’t really exist anymore. But that was the heyday of investing when the market was zooming up and things were doing very well. And then what moved you from where you were at Merrill to go directly to the online world? It was very new any the time. People thought it was a fad. So how did you make that decision?

John: Well, when I was running, one of the things that happened was that Fidelity had come out with basically a no fee IRA and we had an IRA that started at $35 and went up to $100 depending on how much assets you had in the IRA. And we did a lot of surveys to understand why people were investing at Merrill. And that was a lot of money. I think when I started it was 60 million and by the time I moved on to another job, it was 130 million. So I mean it, it was a lot of money that we’re generating through the, through the retirement plans business, but other people were, were in effect giving that service away for free. And when we got behind that, we found out that it had a lot to do with the fact that people were paying.

John: It was another way to sort of pay for the advisory relationship as we went along. We did a lot of research about what our competitors were doing as part of that process. And I, I think I sort of became the Cassandra of the organization saying, Hey, there’s things happening out here that we have to, we have to adjust to. So, and there’s one meeting in particular that I remember where one you know, we were talking about what was going on and because I had ended up on as part of the retirement plan business, also getting a, we started to do market segmentation and I was given a segment called next generation marketing, which was to capture the people under the age of 40 what people tell focus on millennials this is the idea of whatever’s coming up and giving them in the queue early.

John: And so as you looked at that, this was an area where Merrill was struggling. And, and, and in particularly at the time fidelity and Schwab, we’re were in fact gaining client and market share. And, and so as part of that, we had come up with the idea that we needed to do something about it. And I remember one regional director saying all we need is a good bear market and people are going to come back to us because they’re going you realize that doing this on your own doesn’t work. And then we had a bear market and I think it was 92. And the interesting thing about that was our market share didn’t have been decreasing when the bear market came. It, it didn’t decrease as much as sort of level out. But phenolics market share actually didn’t stop progressing up word.

John: And so then we went out and we did a lot of research. And what we found is that if you, and I call it sort of, I don’t know if you have you know, high school children, but you know, when kids were in high school, if somebody had like a bad grade or something, they’re low grade, they may come home and say well I did better than the seven guys. You know, what do you expect? And I think that’s sort of what happened with research showed was if you were investing in yourself and the market went down and you came home and said, yeah, but what do you expect the market went down. I did the best I could that kind of thing. But if you hired an advisor, if you had a guy you know, so to speak, and they were typically men at the time and the market went down, you didn’t come home and say, she look, I did the best I could.

John: You go, that guy didn’t do what he was supposed to do. And so you would not everybody, but people would either change advisors. We did find there was a lot of channel stickiness, but you know, the movement was in a certain direction. And so as a result of that, we started talking about what are the other things how do we get some more competitiveness space. And initially it was to sort of have a call center, which was this thing that became invested in center, which ultimately became, as we went along to make it work and to get an a scale. We also looked at what quality control of advisor’s dealing with clients. And we found that somewhere around 180 to 200 relationships, the quality control, the quality of the advisors, general ratings would start to go down with a significant amount of clients.

John: And a lot of advisors had built their book. And you got to remember in the 80s you could still cold call, et Cetera, generating a lot of customers and then sort of some of them would mature and get wealthy and they would be great customers, but other ones would sort of still be with you. And, and advisors are always worried at that time that you know what I called win the lottery, that somehow one of these customers, maybe they would change jobs and going to roll over or maybe something they didn’t hear it, but you know, nobody wanted to give away these guys because every once in a while one of them would pop up and all of a sudden have some money. But the research was that it really affected their whole book. So we did a bunch of things to sort of one, demonstrate that to people, educate them, et cetera.

John: And then secondly to incentivize them. Originally to move into this call center idea accounts with $25,000 or less. And you know, then it went over to and $50,000 and it was $250,000 I think by the time that I left Merrill. And so what happened is you would get transferred into this call center and we did a bunch of things then, right? Because we wanted the client to be successful. We didn’t want them to feel like they had been downgraded. So we built all sorts of technology to both track activity to reach out to them at the right times. You know, it was sort of the early versions of CRM on steroids and you know, Meryl had a lot of technology and capability to do that. And so that’s sort of was the, the first part of that. And then as time of all this was the 90s the I, it’s hard to think about now actually how primitive we were, but, but there was a lot going on and everybody wanted to do more things then.

John: And you had firms like e trade coming up, et cetera. And so quickly we said, hey this is great, but we have some of these customers that just want to trade online. And then there were advisors, we started doing the research and we found that we looked at where checks were being written out of CMA account. And often they were going to some of these discount and online brokers and we said, look, we would go to the advisor and we’d say, look, they’re going to do this. They’re doing this business anyway. Maybe you can keep it if we have this Merrill Lynch direct. That was sort of what drove the decision making around that. I will tell you that was, that was a very controversial decision at the time.

Craig: How’d you overcome their objections mean those long before people realized how the innovator’s dilemma work and how to cannibalize yourself?

John: One with the lower end, that would be the investment center or a, Oh, what became the financial advisory center? There were incentives. If you kept the client under a certain amount we did different things with compensation. In some cases we would reward you to move it. In other cases we would penalize you to keep it. We did a bunch of those things. So that’s how that business really grew. And in a short period of time, year and a half, two years I think we got about 300,000 accounts in there relatively quickly in. I know it’s continued to grow ever since then. I think on the Maryland online and Merrill Lynch direct, it was not, we weren’t necessarily saying to advisors you needed to move the client. We were making it clear to advisers when their clients were maybe doing business away and that was an option that they could introduce to their clients. We were not on the online side as aggressive about marketing as we were on the smaller accounts side. Generally we had built a pretty good system. We’ve got very good marks from people like Barron’s, et cetera. And so the business we naturally were, were picking up business. We were not doing all the marketing stuff that say Ameriprise or at the time or e trade was doing. So you know, it was a, it was a, it was a business, but it was not a core business.

John: I will tell you the plan was back then, I mean before I left in 2001 the plan of what became Marilyn. Chad, you didn’t have that name, but of bringing those two things together and continue to grow a business, God existed then to your point about incenting or you know, getting the advisors to do it. I do believe the one thing about bank America buying Merrill Lynch, that allowed that to happen because the bank was willing to sort of fried this is from my perception, I wasn’t there. This is from an buyer, but I think it was willing to ride over that objection, which I don’t know that we would have gotten over as an independent company.

John: Yeah, and I think they, the power dynamic shifts over time. Back in Merrill Day, there was, the branch was very much the power based. I don’t know, again, I’m looking at this from afar, but the recent articles about how advisors need to sell so many mortgages, so many loans and they’re dropping the name and this and that. I think that the bank is going at it more like a bank, which is one of the reasons, frankly why we haven’t gotten to where I am currently. But I think the independent advisory model is really interesting. And you know, I don’t see anything that’s going to slow that model down. I don’t think that necessarily that model is growing because people are flooding out of the wire houses. But I do think that all of the direction that growth, the increasing sizes there, and I think that’s because frankly it’s some of the things that made wirehouses rate, I mean, if you think about this industry, when the it started, they were using chalkboards and as we went along, eventually they talked about why are houses being you put the, you put the order in a tube and then you wire it in.

John: And so we still use those names. But if you go back through the history of this industry has adapted technology over and over and over again, and partly it’s because it’s not a commodity so it’s not the travel business where a flight from here to Chicago is the same. A flight from here to retirement for people is different. And so advisors can add a lot of value. But what has happened over time, if you go back when I was there at Merrill, Merrill had a bunch of competitive advantages. One, they had training classes so you could come in and you could get trained in the industry. Second thing they had was new issues which was a big deal originally back then. The third thing was you’ve got research. So you know, arguably Merrill’s research was better than somebody else’s research. And the fourth thing you got was technology.

John: And if you now, if you go forward now, 20, 30 years there, there are very few, if any training classes, people can, can find training and other ways to get licensed. We’ve done some things in the industry to make that a little easier. Secondly, new issues are maybe that will change at some point here in the market, but it’s just not what it was. And you don’t have people getting called up and I’ve got this new issue and here it is, etc. And maybe when some of these unicorn stopped being private, so maybe that will change. But at least right now that doesn’t seem to me to be a big tissue. Third is research because of all the things that happened in the late nineties it’s sort of somewhat embargoed and you can go out like go to places like Cfra, the old S&P 500 research and you can get as an independent really, really good research in many ways that not very cost effectively.

John: And so the fourth, the fourth rail was technology. And now if you look, I would argue the same way that you know, things like the iPhone and Vance. So aggressively in the technology space, you’re seeing exactly the same thing in the independent space. And I look at what you can get often in technology, the wirehouse and what you can get as independent. And I would argue in many cases the independent have a more flexible, more open architecture, better technology solution today. I know I sort of jumped ahead in your interview process, but I think that’s a trend that is going to continue in the price of technologies coming down. The ability for it to integrate is going up the choices just like on your you know, I, I often say that people don’t think of it a smartphone this way, but a smartphone allows a consumer to have his or her unique technology stack because they can just put whichever apps they want and they will just work. And I think you’re seeing the same thing in the financial and wealthtech space.

What was the impetus behind starting BullRun Financial?

John: Yeah, so I had well one I was associated with Dave Command city. I had been a strategic planner, a number of things that at, at Merrill and I had been around long enough to know sort of the old team new team thing. So there was some so I was sort of watching as the, as the water was changing, but more importantly, I think it was the late nineties and early two thousands and all of us and companies like Merrill were watching people in the Internet world doing all these interesting things, et cetera. And I think I very much wanted to try my hand. And then I had been talking to a board member at one of the online companies and he was associated with this company, which was actually called on their board. And they had, they had some issues that they thought I could solve.

John: And one of the reasons I was talking to this board members, they had tried to recruit me to, to go to another company that was the middle of the, of the country. And because my son was getting ready to go to the Naval Academy, I didn’t want to move. And so he had approached me and said basically that anybody who would look at this other job as long as I had obviously might be interested in doing something else, then staying at, at, at Merrill and they had this really cool company, they thought et Cetera. It was a semi virtual company and they would move the headquarters to New Jersey. And so I bet on that actually started on August 20th of 2001 and we opened our New Jersey headquarters or office on September 10th, 2001 and, and needless to say, the t one, and this is how you know how much things have advanced, right? I mean literally one to one right now your anything, you can get multiples of hundreds of that right, but did not show up on September 11, 2001. So the interesting for me as I went through what people call a nuclear winter and the sort of startup space and and learned all sorts of interesting lesson through that process.

Craig: I was at a startup as well at that time. So it was a, it was definitely a not a great time for startups. And then the fact that you persevered through the financial services nuclear winter and then eventually sold the business I think speaks volumes to maybe your background, dedication and connections and just your drive to succeed

John: What I said earlier about West Point. I think that was probably there. My wife would tell you it was just hard-headed man.

John: And that maybe I should, maybe I shouldn’t have spent so long doing it. But yeah, we did. To your point, we take it to a exit and, and then after a lockup period I went to work at Bloomberg. But it was it was an interesting time. It was also an exciting time to, I learned a lot about, I guess what I would call solving pain points. So at Merrill we did a lot of research and we talked about it earlier, but what I learned quickly in the, if you’re going to sell to a financial advisor, and especially back then, again, a lot of it we were, we were targeted at our product was basically performance measurement and attribution and much other things that people thought were cool and consumer facing. But target market was portfolio managers and very high end wealth advisors.

John: The, there is a difference between a nice to have product and a have to have product. It has to have products, has to solve real pain points. And so over the roughly seven years I was at BullRun financial we learned a lot about that as we persevered and ultimately got a product that worked and then ultimately exited the company. I also learned a lot about how, you know venture capital works and fundraising and all those kinds of things. Most of which you know, I probably would have preferred not to learn that way. I can just be stubborn and hardheaded and persevere. That’s a positive and a negative.

Can you tell me about venture capital and how that works?

John: Yeah. Well, and I will tell you this, this is I when I think when somebody comes for a big company guy for a venture firm, they’re either really likely to be close to becoming a Unicorn and flipping or, or you know, they have their bigger problems and they’re dressing up a little bit. And, and in hindsight, I think we were in the second category, not the first. I think we were able to ultimately get there successfully. But you know, one of the things which you don’t see any more, but you know, the investment round before I joined the company, he had included three time preferences for the venture capital firm. And we actually had an offer to be bought in 2006 by Reuters. But it wasn’t high enough from the venture firms point of view. And so they had they basically blocked it with their, with their three times preferences and you know, their theory was that already in, in Reuters selling product and you know, go another six months to a year and waiters will pay a higher price.

John: And I’m sure that most of the time that’s good business decisions. What what we didn’t know, what they didn’t know is the Thompson was going to buy Reuters and Thompson had a competitive product. And so we went from, we went from being an acquisition to being thrown to the side of the street. And so we did successfully exit two years later, but you know, we would have been better at exit in 2006 at the earlier time. And pray.

Craig: Yeah, there’s lots of hindsight and seeing what mistakes people make of not selling is probably more often than people will say. Well, we sold too early. That happens less often than let him, we sell at this time.

Craig: So tell me about the after the exit of BullRun. Did you take some time off? You know, how long before between BullRun?

John: Well, I think it’s probably by two years. December of 2008, I’m not 100% sure of this, but I think I was one of four deals that closed in 2008 after the market crash. And the only reason we closed as we had actually started negotiating the deal way back in the spring. And again, I think it was, that’s where the sort of perseverance and west, I just refuse to let the partner that had agreed to acquire us, not to, to walk away from that. I think in some regards after 2008 after, after a October, 2008 people want to do lots of things. But anyway, we closed the deal and I was locked up, which is why basically I was out of the market for a year. As part of that then I got you know, as I was looking for what I wanted to do and what I actually thought I wanted to do at the time was sort of an IRA roll up.

John: I could see that sort of in the marketplace, there’s sort of like, focuses on are dying, she’s done. But as I was going around talking to people, I’ve met with a private equity firm, we said, hey I don’t know what they’re doing, but this guy Tom Secunda over at Bloomberg I think he’s wants to do something with IRAs. I think he’d probably love to talk to you about your experience, et Cetera. So I went over there and, and the interesting thing was that they had actually hired a search firm from California and they had been because of what they wanted to build was, or at least what Tom wanted to build the time was it was a Robo advisor or the equivalent of that. I mean, that word did, I don’t think he just did at the time.

John: They could see that sort of coming in and they want to move in the consumer business. They had a, they had open things like a real estate business, a law business or sports business. Tom wanted to, to open this Bloomberg wealth business, a direct to consumer business, and they’d actually in their SPEC had defined, one of the guys who were looking for was a guy who would go Marilyn’s direct, et cetera. And so how the search firm hadn’t found me, I don’t know, but you know, it’s not like I was all that hidden. But anyway, so I’m started meeting with Tom and you know, it was a he had this idea they wanted to build this this direct to consumer business. And you know, it was a, it was a relatively short, a couple of conversations and I was like, this is cool.

John: This is what I’d like to do. And as I said, I’d been through the raise capital and all that and I thought, I don’t want to, I don’t want to do that again. I’d rather just listen. Mrs like Merrill Lynch again, right. You have you know, he got plenty of capital. You don’t worry about making payroll. You’ve got a business plan. Yeah. You have to do all the politics and the PowerPoint presentations, et cetera. But as long as once it’s approved, you run hard. And so I got hired to do that. Interestingly, a guy named Bill Harris was a consultant at the time. And for a number of reasons he ended up exiting not because of anything I was doing, but more of some of the business things that Bloomberg wanted to do and not do. We were building this team and we were building, we were going to build an equivalent personal capital.

John: If you go back and look at the, all the design, just stuff in the first six months from that period. And but Mike Bloomberg had the right to he was married at the time, but he has like a strategic review for things that were considered strategic and we were considered strategic. And so about six months into that, I’m doing a briefing for him. And he said, this is great, but you can’t I’m not going to let you charge on assets. I don’t want to compete, compete with my customers. So you know, figure out whether you can you have a business here doing something else. So we then spent a bunch of money doing a bunch of research, sort of back to the early days of marrow when I got about the research that we did and, and, and we asked what I would call the third order question which is, so the first order question was you know, if you go out and you ask people, what do you think advisors, they get very low as a group rating, sort of similar to Congress.

John: And if you ask them how much they pay, they’ll stay too much. And if you really push them, they may come up with 1%. And I think this is what that kind of research, that kind of communication at first or a question drove a bunch of people from betterment and Wealthfront and all these guys to say, Hey we can do this. What advisors do is they managed portfolios and we can just go out and do that. And we can use technology. And here’s all this research that says you, you don’t need to, you have active management or whatever it is, right? And so they went down that path. We did that research back in Maryland in the early nineties and we had gone to what I call the second order question, which was weigh the same but, but why do you have an advisor, right?

John: Because you have an advisor and they would go, oh, he’s not like everybody else if he’s not like those other guys. And that’s why, again, I use the congress analogy, right? We all go, we hate congress, but we sent our congressman back every year because we like him because he’s not like all those other guys. And so I was thinking in many regards, that’s what we sort of discovered at Merrill and lots of other firms did too. And I think that drove a decision generally in the industry that, okay, what you need to hire is likable relationship guys, because you do business with PBL. Like if I like you, I’m going to do business with you. And I think that drove a lot of the industry for the next 10 or 15 years. But at Bloomberg, cause we were really trying to figure out like is there a problem here because we felt there was a problem.

John: We ended up asking the third order question, which is well wait a second. If you look at all the research you don’t as people, we don’t have all of our assets without advisor. Right? So why don’t we have allied I with your visor? And then what we heard was, well I liked him but I don’t know if I can trust him, but it wasn’t like him personally. It was like, cause I don’t know if you can trust anybody in today’s world and you know, and we’ve got lots of examples 50% divorce rate, right? So you can’t trust your spouse at the time or this or that, whatever it is. Right. And there’s lots and lots of examples and you see getting played out in the politics today. Also. I mean people have this. So when we ended up then doing is saying, okay, the problem is trust, can Bloomberg pet play a role in that?

John: And what we decided was, and it fit with sort of the culture of Bloomberg and the business model of Bloomberg, we could deliver an information management system that BullRun that help clients know what was going on with their money and therefore a de facto also trust or not trust, but either way prove that what they were being told, what’s happening when their money wasn’t that happy with their money. And, and so then we did a bunch of research and determined that there were basically four pain points. And first one was how much money do I have? Because people, as we said already, they spread it out. And originally when I started this, I thought they, I thought it was just that some people were sloppy. Right. You know, I have an account here, I have an account there. It’s just it’s too cold.

John: When we really got behind the research and we talked to over 6,000 people in various different instruments. What we found was, no, this is pretty much an intentional thing that nobody, that they grew up in either because they read about Madoff, and remember this was 2010 so he was very, 2011 he was very much in sort of the news and people’s mind a but, or you know, your mom said, don’t put all your eggs in one basket, but whatever. This is the, this is a pretty deep cultural thing we saw. The first thing is how much how much money do I have because I haven’t spread all out. And when I was 30 I put it on a spreadsheet and I can figure it out. But now I’m married, I’ve got two kids, I’m 42 which was sort of our core client base and, and I have $1.8 million again, which was sort of the core.

John: And that was, that was what the averages were coming in when we were alive in the business. And I’m too busy. I I got, I got kids in soccer, I got ballet practice, whatever it is, I need some system to do this cause I don’t have time to sit down and put it in a spreadsheet. So the first thing was how much money did I have? The second thing was how’s it doing? And so from Bloomberg point of view, this was very, because everywhere. So we basically figured out how to aggregate assets and do performance reporting assets wherever they were. One of the things we found out though, why we also found out that again on this idea of trust and we asked why you don’t trust your advisor necessarily give them all this. And one of the things we heard over and over again was that when I say, how am I doing?

John: And the advisor has to give me a 30 page performance report and it’s got lots of graphs and charts and numbers, etc. And he starts talking in effect Mumbo jumbo about it. It doesn’t increase my trust. I’m like, I just asked a simple question, how am I doing? What are you hiding here in all of this stuff? So it actually lowered trust. So one of the things we spend a lot of time at Bloomberg was what are you going to, how to communicate performance. And it’s really much simpler than most advisors do. The third question was, is it being watched? And this drove that because most people, if I liked the guy and he’s good, he’s good relationship guy. I played golf with him, I have dinner with him, but you know, he’s not checking his, his phone all day to see what all the other clients are doing.

John: So who’s watching my money? And, and then we did some research and we found that most people think that technology is better able to watch things, that they’re not convinced that it can manage things. So it’s not like they want to say you should be trading my stuff, but they do want it to be alerting their adviser and themselves if there’s a problem. And so we could solve that one. The fourth problem they wanted, which we didn’t solve it. Bloomberg where we’ve solved since was a will I meet my financial planning goal. We did a bunch of things around that at Bloomberg, but there was an internal debate about the effectiveness of financial planning when you’re looking at 10 or 20 years and whether that’s really a valid thing, et cetera. So in Bloomberg, we didn’t do that, but those were the four questions.

John: And so it was there. So that was the first thing we set out to solve. And they wanted, as part of that, some ability to talk to humans. So Bloomberg, we put in a whole customer relationship module so they could call up and get questions and we could talk to them, et Cetera, about what the technology was telling him. Not, not should they buy or sell a security, but you know, how it works, et Cetera. And that was very important in the value proposition for them. But what we also found out was after you answered that question, those four questions, the pain point that you have goes away because tomorrow if I have 1,000,008 350,000 today, tomorrow I’m going to have plus or minus a little bit. And if performance is 6.7% today, tomorrow’s going to be 6.7% plus or minus a little bit.

John: So people weren’t like, okay, I got this answer cause I need to go get this answer tomorrow and the next day, et cetera. It usually goes away for about six to nine months unless there’s really something going on in the market. So then what happened, which was not in the research but which we discovered primarily because Bloomberg has a lot of content and they said, hey, can you use some of this content, a sentence here, free anyway. And in particular they had bought Business Week. So there was a lot, sort of more consumer friendly investor-friendly content. And so we started testing what what was valuable and cause if you go out and ask them the research, do you want more content? People will say, no, we’re all feel like we’re overwhelmed with emails and all the rest of their stuff. But when we found is if you gave them content just often enough.

John: And so we created scoring miles to figure out which is just often enough for each client. And they got more and more sophisticated as we learned more and more about the clients. It was somewhere between every two weeks and every six weeks was probably about right, depending on who you were. But the second thing was it had to be relevant to you. You had to understand why you got that content and you didn’t want a middle of the class newsletter. You wanted to know something that would be valuable to you. And so the example I use now, I wasn’t at the time, but you know, maybe that Brexit, what does Brexit mean generally? That might be cause you have European exposure. We did a bunch of things to learn to try and do that. And we had very sophisticated expert systems.

John: And in some of the stuff where you have carried forward, now people call it artificial intelligence, but basically figure out who you are, what content is relevant to you, give it to you just often enough that it’s valuable to you. And now in our current world and the view it, we as coming from the advisor versus coming from it’s in Bloomberg where it was coming from Bloomberg. That turned out to be very valuable. And people would check in on that periodically. And now where we do it, back then we didn’t have an APP, but today we have an APP and I call it the Starbucks effect or the coffee shop effect. If you don’t want to use the brand, which is I’m standing in line in the morning, I’ve checked my email, I’ve checked my Facebook, I’m still waiting for the right coffee.

John: And I look and I see that there’s a little notification on my, on my app. And I open it up and I read the content and again, assuming it’s relevant, I then find it to be useful and it increases my level of trust that we’ve added to this. Now, we didn’t have this ability of Bloomberg and we’ve added to this ability, the idea that we don’t just do investment content. So you know, if the advisors put it in the CRM that you like red wine or you liked the Yankees or whatever it is, you will periodically get some content about that. And, and if you go back again to those roots of the nineties and late eighties guys used to get the wine spectator and if I knew you liked a certain wine and there was an article on it, I would rip it out. I’d photocopy it to the four guys that liked that wine. I put a note on it and say hey, I thought you’d find this of interest right? And nothing to do with investments. What it did is it said, you and I know each other, we have a relationship and I, and, and I’m reinforcing that with the content. And now would you find this technology more and more as able to also do that? So anyway, that was sort of the Bloomberg field.

How did you start CircleBlack?

John: We launched the product in May, May 1st of 2013 we’ve done a ton of research. We’ve done a ton of testing. It was the kind of thing you can do in a place like Bloomberg. And we launched and every month we doubled the customer base. And remember this is a product we were charging. It was in the information product we were charging $100 a month for. By the time we closed down for four, four and a half months later we were at over a billion and a half in assets and 700 clients paying us $100 a month. The average client was a, as I said, 1,000,008. They were aged 40 to two kids. I mean, we did all this stuff that you can do again with research to understand who they were. We would seem that we saw the hockey stick effect you know, and, and honestly and it, I believe that Bloomberg and I know there are some people in Bloomberg and believe it was that they, they should have kept going with it.

John:  But there was at the time was a guy named Dan Doctoroff and he believed, even though we had done all these things to prove that we were not competing with any of the Bloomberg client base, that somehow it was still competitive, the client base. And so like a lot of big companies, there was a, there was some politics involved with that and they ended up exiting from all of the consumer businesses in one way or another as far as I could tell, except for Businessweek and, and the, and the TV and radio, which I think is as much about influencing the general discussion as anything else. I think that we hadn’t launched I would have probably not made the decision to build CircleBlack and, and cause again, the, the, the things I learned in the early two thousands about apple raisin, et Cetera, and how hard it is to be an entrepreneur in this space.

John: You know, I, I was you know I probably would not have said, hey let’s do this. But we had seen the hockey stick. We had been actually working on a version of the product for advisors in Bloomberg because we had a lot visors that thought originally we were going to be a robot advisor cause that rumor had been out. And so they ended up coming in and testing the product initially. And then deciding to say, Hey, can you do a version of this for me? So we had started on that. So when we ended up leaving with Bloomberg splashing they were, they were fine. That we could we could do something we can take whatever it was in our head and we could do it.

John: And we weren’t, we weren’t taking the technology and there were some things they wanted and we made sure we complied with those. So we decided to, after some debate and discussion, et Cetera, a number of us said look, we really think that the market needs this product in particular, advisors need this product because we could see the stress thing. And so we decided to go Bloomberg, it was B2C and, and that made sense from Bloomberg’s point of view. But for us now being an independent company, we wouldn’t be B2C. We spent two years building the product. We launched January, 2014 we spent two years building the product and then we went live on January one, 2016. And glad to talk about your current business as much as you want. I know you were more interested in the history. So tell me talking about why you CircleBlack is a great thing, et cetera. But tell me what you want me to talk about.

Is CircleBlack self-funded?

John:  We’ve self-funded and privately funded. So we have you know, besides you know the money that I’ve put in, we have about 25, 27 investors that have invested in the company, almost all of which come from the industry. And this, this is a little bit related to my background with the venture world. I think that, I think one, fintech takes a certain gestation period. It’s a little longer than some other things I think. And so we wanted to make sure that we had sort of the right capital structure for that. We also have intentionally sort of done what I call it as sort of New York focus, which is we’re very focused on a business that is that is a, is a, is a business versus just growing market share and trying to go fast and raising more money and raising more money. So we’ve tried to be very capital efficient, maybe two capital efficient and sometimes but in particularly, we look for investors that you know, not only could add capital, but more importantly could add their intellectual capital and their connections and came from the came from the industry. We’ve been pretty successful about that. And I think that’s paid off well for us.

Craig:  I’ve heard that before were mostly from New York people that they feel that firms at launch on the east coast are more capital efficient and more about building a business. Whereas firms at lunch in the west coast are more about building a company that they can sell.

John: Yeah. And again, I don’t, I don’t know. I mean, I’m not on the west coast. I’m on the east coast. Big Dollar checks being written out there. But I think we you know, for us it is very much about trying to be capital efficient and build a business and solve those pain points and grow look, from my perspective, I’d rather sell products then stock. I will say we haven’t made it easy on ourselves. I think it’s a harder way to raise money then sort of just going and finding a venture firm and taking a big check and, and, and, and going forward. But it, you know so I don’t, I don’t know if there’s a right or a wrong way. I will say as a call out to New Jersey, they have a number of programs that that we’ve leveraged that are in that encouraged technology and also biotech.

John: But I mean, we’re from the technology side, so we’re you know, so our you know, we’re a New Jersey based company. Do have our primary development office in Jersey City right next to exchange place, which allows me to get all the young, New York talent, you know, that, that wants to, it wants to work for cool growing Fintech company. We also we also have done some partnering. Right now we are, we’re leveraging their capstone process where they have teams of people work on projects for industry. So we have four projects with 17 of their students working on that. And that’s been very helpful to us. I think there’s a lot of, I think there was a lot of reason to be in the greater metropolitan New York area in particularly in New Jersey.

John:  It’s worth talking to the NJ ADA. I think they’re trying to do a lot of stuff to encourage firms like us to be here and, and it’s been, we’ve been we’ve been very happy with the talent center. I will tell you the interesting thing about BullRun financial the company in the, in the early two thousands, we were actually located in Hamilton, New Jersey, right on the northeast train line. And I thought it would be easy to get programmers to come out in New York City because they could just take the train line, literally they could walk to her office. And I found that I could get lots of senior technologists who were tired of the commute, but I couldn’t get the young people. So that’s one of the lessons learned from the prior war. That’s why we’re in Jersey City.

Craig:  So let me just transition a little bit. So that was awesome. I really, I mean, I like to hear people’s history and, and you know, there’s a lot inside of try. I could have done another hour on that, but I didn’t want to dive too deep. I thought you did a really good job of spending a lot of those, a lot of different steps in, in your career journey. But let me transition to a different set of questions, which I have adapted from someone that I respect him in the podcast and what his name is, Tim Ferriss, who has a podcast called the Tim Ferriss show. And he asked these very interesting questions and I adapted some of them for my own podcast.

What has become more important to you over the past few years?

John:  I think, I don’t know if it’s become more important. I think it’s always been really important. I think that I also think you have to be true to what makes you excited to get up in the morning. And I’ve seen a lot of people in the financial services industry that chose it or do it. And then some other professions like law or whatever because of the money. And I think it’s important to you know, we talk about this a lot as, as a society. But I mean I think there’s a lot of truth to do to figuring out what makes you happy and trying to and trying to make, and then trying to find things that allow you to be productive and do that. And I would argue that for many people you go to work because you find it interesting and you enjoy the solving the problem or whatever it is that you’re focused on. But at the end of the day, the benefits of whatever you make and use it for us is, is usually somewhere related back to your family relationships and try and I think we all want to, to feel like, hey I didn’t, I didn’t, I didn’t miss those opportunities. At least I do. So I’ve always tried to make sure that I was connected in that regard.

Craig:  Yeah. That reminds me of the work, the work life balance and how you and the different areas of this four different areas of your life and is it something you enjoy doing something you could make a lot of money at, something that’s good for society and how those things, all the overlap of those is the perfect job.

John:  I think that’s correct. I do think we have as a society, and I think we’re coming back to the heat, go back and look at the agrarian society. There wasn’t this, what I hear people say when they got about work life balance is like I work eight hours of my job and then I go home and I now I have my personal life balance and you know, I try and balances out and what I’ve seen, and I think technology brought this back, you went back to the farm you lived and worked in the same place and now today a lot of people are, are we? And we all try and figure out what the right balance is, right? But we’re connected 24 seven right? We are always connected. And so in some regards, work can always be there. Now you can, you can be, you can let that overwhelm everything else, but you can also, it does allow you to do things like go to a kid’s basketball game and, and, and yet still be able to check out or check.

John: In fact, back to the Bloomberg black days we used to have this one of the research guys, I still remember him. He took us, he took us his phone. I didn’t probably back then it was a blackberry and held it up. And he said, if you can make this 30 seconds of checking time so that I can be at a soccer game and check my wealth or be waiting for a plane and a train and check my wealth, that’s really valuable to me. But you gotta make it 30 seconds. I don’t want to be like having to get my computer out and turn it on and you know, blah, blah, blah. And I think, I think that’s what the, what the, what we as a society are trying to figure out when we go about work life balance. I think it’s now in a connected world and I don’t think it’s an honor I’m off. I think it’s, how do I check in? How do I check out? How do I make sure there’s a balance that, and when I’m having a conversation with somebody, am I focused on that conversation? Can I ignore that technology? But then when I check it on a technology, can I, can I be focused on it and then and then be out

How do you stay motivated and keep your entrepreneurial spirit going?

John: Oh listen, I like you got to be solving a problem. And I think we’re, we’re very focused on,

John: I believe the industry needs more things to help advisors and their clients stay connected and that build that trusted relationship. And I think that clients want to have relationships with people that can add value. And that most of us think that again, from the research, most of us think that finance is very important, but about 80% of us would rather do other things with our lives and worry about that. So I want to have a partner and I want to be able to trust that partner. And so I want to, to do this. So we spend a lot of time saying, are we solving, are we solving a pain point either for the end investor or for the advisor? Because obviously we want the end investor to get the technology, then the advisor has got to have his or her problem solve. And so, I mean, I just, I find that hugely interesting. And I think the space is moving very quickly. I think there’s a lot going on with technology, etc. I do think I have you know, as you said, I’m older, so I have millennial children and some of them are worried about, yeah, I know. That’s all right.

John: Yeah. But you know, they’re worried about will there be this society and in teen years where there’s the haves who have jobs and are working and interesting. And then the, the, these other people that aren’t, don’t have jobs. Now I tend to be an optimist and think this is all going to work out. But I do know that it makes sense to be looking ahead to where they used to say where the puck is going. And I think that understanding how technology and humans interact and what that’s going to be. Those are very interesting problems from my perspective. So you know, one of the things that I don’t see, like I don’t have this image that the, hey, I need to be playing golf in five years, five days a week or whatever. You know, I probably don’t want to work quite as hard as I’m working, but I really enjoy what I’m doing. I think it’s important just to figure out why you’re doing that, how you stay connected with the other parts of your life. Like family.

John: Well, I have a father in law is 96 years old and I think he worked till he was in his eighties. He had that he was he had, he was an entrepreneur also. And I think this one of the reasons why he’s lived so long, I think it’s I think you have to have a perfect, one of the things I guess you have to have as a purpose. And I’m not saying that retirement’s not a purpose, but I think most of us need a reason to get up in the morning. And if it’s doing the job that it may be doing volunteer work or, and, and, and all that, fine whatever, whatever’s new makes you happy. That’s, that’s sort of what the focus ought to be. But I just I like what I’m doing so I don’t, I don’t see not doing it. At least I might be doing it differently. I might be doing it for a different company. I might not be doing it as much, but I, I see sort of, this is interesting stuff.

What is something that you believe that other people might think is crazy?

John: I’ll tell you what I do. I don’t know if it’s crazy. There are two ideas that I would love. I’m going to slightly work over in politics now from a particular view, but I would love to, things happening in this country. One is I firmly believe that we need universal service for a year or two. And I think we should call it a different word. I think we should call it a hack. And I think everybody, regardless of your income level, could pay this tax and somewhere in between 18 and 25 or whatever it is locked out of the country that can do it. And I don’t think it needs to be the military. I think it will take be a choice. You could, you could work on an Indian reservation, you could change bed pans.

John: And I think this is important because I think what ought to happen is if we did this and required and I think it has to, you can’t be able to get out of it. Whoever you are, you have to do something. And I think you also have to do it in some other part of the country than where you live. And because what I saw in the military, one of the things about the military was it mixed people from all sorts of different parts of society. And I think that actually does a lot to break down these barriers that exist about what we think about each other and what I would call the others. Whoever the others are in your life. Could you actually meet those people? You spend some time with them. And I think it also expands everyone’s arrived. And so frankly that I’ve been on that from my personal belief.

John: I don’t understand why that doesn’t happen because I don’t talk to anybody in the mix is a bad idea, but it never seems to move forward. The second idea, and this has to do more with my current business, which is I firmly believe that there should be a program for firms like ours. It say if you hire a programmer over the age of 40 who is a first time program or there’s a tax incentive or there’s a tax incentive for somebody else to train them or whatever, because I hear from people all the time, you know that well you have to be in your 20s to be a program you had to grow up with technology, et cetera. And to me programming is just language. And I see lots of people that learn French when they’re 60 or whatever. Right. And I haven’t seen any reason why they can’t learn programming when they’re 40 and I will tell you pro, at least from where I sit, generally programmers are hard to find.

John: And so we will hire programmers out of computer science program for will also hire them out of programs like General Assembly, which is I think six months of sort of basic coding. And then they get a lot of OJT right when they come to work there. But I, I just, I think that as a society we have sort of this and, and if you go back and economic books they talk about the car and the horse and buggy and there’s this, whenever you have these massive technology shifts, there are people that get left behind. But interestingly, I don’t think in all cases they need to get left behind because this is a skill that can be learned at any age. And, and, and we should encourage people that are for whatever reason whatever they were doing isn’t, isn’t as much of or as available. This seems to me like we should encourage them to get this training. I think it will only make our society richer.. So I guess that’s as close to the crazy ideas.

Craig: I have a computer science degree, and I can say that programming has changed tremendously in the last 30 years. It’s a lot easier to program. There’s a lot more languages available, a lot more things you can do using scripting languages and such that people who don’t need to have the engineering or math backgrounds that we had to have. That that you can still perform programming and programmatic type tasks.

John: Right. And, and firms like ours are looking for those guys and gals.

Craig: Give us an opportunity we can explore.

John: Yeah.

How do you identify people that will be a good fit for your firm?

John: I think it’s all about culture. Culture comes from both sides, right? It’s the people you hire are, they bring some culture to it. And then it’s also culture that from management love where you’re sort of driving down and you know, listen, I, I don’t think any of us, at least, we’re not perfect at it, but we try and be clear about what differentiates us, what we’re trying to do, what we think is fun. You know, we have sort of the normal interview processes, et Cetera. We make sure that, that people spend some time with us before we make them an offer so they can, they can see what we’re liking, what they’re like. I mean one of the benefits of you know, firms like ours is pretty, there’s a lot, there’s a lot more flexibility than they might be in in a, in a big firm.

John: Back in the day at Merrill or even when I was a Bloomberg there was a lot of wear a coat and tie and we’ll bring your badge, Danny’s badged out and all this kind of stuff. And there’s nothing bad about that, but you know, it you know, CircleBlack if you want to come in shorts or tee shirt or whatever and you know, you we have lots, I mean the Thai initially story that, so the, the, the guy that is our landlord, where are our tech center is he had I wanted to make sure when we did believe that we had 24 by seven access and I said to him hey, I got guys and work late theoretically, well he had a, he had an alarm on his door that when somebody went out in or out between 12 and five, it would camera would go on, an alarm would go off in his house and in effect wake him up because I think very rarely that happened.

John: So it was sort of a security measure. So we started working there and you know, after about three months, he complained because she woke up almost every night if somebody was leaving it at two or three in the morning because if you like what you’re doing, we had guys that that they were involved in a project and we were we were building things and they wanted to do them and so they stayed till they were done. Not because we said you have to do this, but because they found what they were doing really cool.

Craig: You’ve got people who are getting paid to do something you enjoy. So what is your morning routine? What do you do during the first 60 to 90 minutes of your day?

John: Some of it is aspirational. I typically try and exercise you know I’m a I’m a guy who likes to set, so I’ll sit down, set my priorities and then the night before. But even if I do, I’ll review them in the morning. Depending on schedule, they have a breakfast meeting or whatever, but if I, if I’m going to the office, I probably typically will spend after, after checking my priorities. I and I know periodic, I tell myself it’s not the most efficient thing, but I usually found through you know, the first set of emails and then and then I’ll hit the priorities and then sort of do the same thing at the, at the end of the day. But I tend to be very much focused on a to do list, which is always way too long. I’ve found different technologies and different ways to sort of prioritize it into the into the top five, the top 10 whatever. But that, that’s seems to be I don’t know though that I am the you know, I’ve probably read every efficiency book, but I don’t know that I would say I am the poster child of that.

John: Yeah. I will tell you why things I do try and do is and I got this, I worked for a guy in line, he’s stepping back at Merrill and he used to talk about people should spend an hour a day thinking about their business or whatever.  think you’re always thinking about your business, but I do try and, and take a couple of minutes every day to sort of think about a problem. And I usually I have I don’t do it. I do an online sort of Evernote. It’s kind of journaling kind of thing. And so I have, I have lots of these like problem x and I’ll spend 10 minutes you know, sort of brainstorming myself about how it ought to be or, or, or you know, what might be potential solutions. And I I find that helps in this business, like any other business, there’s a, there’s a balance between creativity and technology and, and you know, you’re successful if you can get that creativity brought, at least from my perspective.

Who do you think of when you hear the word successful?

John: You know, it’s I, I don’t, I mean I think there’s some obviously I figure people like politicians and generals and some guys in industry, but I tend to think, I tend to measure it in a different way. I guess in my personal life is there are people that are happy or happier and, and I think they’re successful. I know some people that are viewed as successful on the outside. We all have, we all have internal struggles. You know, it’s like you know, if you drive by somebody’s living in a big house, she go, that would be nice. Or I don’t know how many people go, oh it must be great to run your own company or whatever. And it’s great, you know? But it’s also there’s a, there’s a, there’s a challenge to it and you know, every day is your number away from it. You’re never you’re never like, hey you know, so I don’t, I don’t know that I, as I said, I try and I try to, I guess I spend more time trying to think about as what I’m doing hopefully making myself and my family happy and those I care about and less about gee, this is this is Uber, let’s say, and I’m a, I’m a unicorn.

John: You know what I mean? Yeah. I’d love, I’d love that to happen, but you know, that’s not my fault. That’s not my focus. My focus is on, are we solving problems and does it make me happy to solve the problems I’m solving?

What bad advice do you hear being given out most often?

John: That’s an interesting question.

John: I’m involved in some entrepreneurial organizations. I think that, I don’t know if it’s bad advice. I see people that very much feel like their children should follow them, whatever they’re doing. And, and I, I think it’s important to not that they shouldn’t come into the business. I mean, you know but it needs to be their choice and it needs to be, and it needs to be in their way, whatever that means. You know, I think, I think too many of us just didn’t envision a day where things are going to happen away and don’t have enough conversations about that. So I guess if you’re that would be more on the entrepreneurial side, but I don’t, I don’t have a, I don’t have a long list of bad advice because again, I think it’s customized to who you are. And my wife has the same. It’s like here I’m a tell you what I think, take what you want and leave the rest behind. I think that’s, I think that’s sort of true. I mean even if somebody who’s listening to this interview, I assume that they’re only going to go, some things will resonate with them and they’ll be like, oh, that guy doesn’t know what he’s talking about.

Craig: So with many different business ventures and different careers, some succeed and some don’t succeed. They say we learn more from our failures than from our successes.

What is your favorite failure that you learned the most from?

John: I learned the most from the, the seven or eight years of BullRun financial. We’ve tried to incorporate those lessons into CircleBlack. The challenge of that though, I am reminded that you had to be careful not to fight the last war. So one of the, you asked earlier about what is our funding and why we had chosen to only fund privately and not do a venture round that we so far. That probably has a lot to do with my experiences at a BullRun financial. They may not be those, those you have to, you just, you have to be careful that you don’t you know, as I said, fight the last war, you’d have to recognize that it’s a different environment, it’s a different business, different things are different.

John: So I think that the challenge you, I think we all have to continue to challenge ourselves to say you know, am I making the right decisions? The, I guess the one, I guess the one thing I would say that I don’t know if it’s bad advice, but I think too many of us also look backwards. And, and by that I mean you know, whatever the decisions weren’t good or bad, they can’t be changed. So my mind, I tend to look at every day I get up, and maybe this is back to your earlier question and say, what are the, what are the things I should be doing today? Because whenever I did yesterday, even if it was wrong, I can’t change it. You know what I mean? It happened. So, and I sort of look at that also from a time point of view I hope that I’ve got another 30 years left or whatever, but I also recognize that as you, as you never know whether tomorrow is really going to come.

John: You can be driving down the road. We use this phrase and my company to do we have the right do we have enough cross training? And if somebody gets hit by a bus and you know, you don’t really think about that, but you know, and it doesn’t happen very often, but you know, people do it and get hit by that proverbial bus every once in a while. And so you just want to make sure that you’ve, you’ve thought that through, both for yourself and for your family and for your investors and for your company.

What book have you gifted most often?

John: It tends to be within the company. Where I’ve given business books like the one that I think has been most useful to us as a book called Traction: Get a Grip on Your Business.

John: I have also given books to friends. One that I particularly like is one called New York, The Novel by Edward Rutherford. And the reason I like is one, because I’ve spent so much time in New York, I just found it fascinating how he does a very good job of describing how the city grew up. But the other thing I sort of found fascinating is, and this may just be because I have three sons, but he does a lot of who does a lot of discussion about a father son relationships and how if you sort of go through the book sign generally are the sons are generally successful but almost never at exactly what the father did. So, and I think the impact of the earlier discussion, I think that’s a good we all, especially as fathers, we all sort of we can be very like, you should do this or you should do that. And I think it’s important to sort of recognize that everybody has, their paths are going to be influenced but different.

It was if it was possible, what message would you send it to your 25-year-old self?

John: I think I would have been less worried about laying everything out. I mean I took in one hand, but you were asking him about professor. I had read the people that there was a study I think at Harvard or where people that wrote down their goals were more successful and people that did so I’ve been one of those guys who writes down the goals. I still do, I have a bucket list now. I read a book, Bucket List Journal and he created a hundred things on his bucket list. And I thought that’s an interesting idea. I tried to do that. I think I came up with 25. It’s really hard to like find a hundred things that you have to do or whatever. At least from my perspective. Maybe that’s because I’ve traveled the world a lot and seen a lot of things already. But I think that sometimes it can become too focused on sort of the goal and less on the journey. So I guess I would say try and enjoy the journey more.

Craig: That’s a good one. And would that change if you were sending the message to your 35-year-old self?

John: Yeah. You get, you get, you do get in the battle. You know what I mean? It’s like sometimes you’re just like, hey, we’ve got to get this shot off today. And you know, sometimes what you thought was really so important today, if you look back at a year later or six months later, it just wasn’t a big deal you thought it was.

Craig: And just to end things, I really appreciate your time.

John: Thank you. I hope it, I hope it turns out well. I’m, I’m sort of interested in seeing how it looks.

Craig: It’s going to look and sound fantastic because there’s a lot of interesting stuff that came out of it and I appreciate your openness and willingness to talk and to kind of share this with all of the listeners.

wealth management consulting



The Wealth Tech Today blog is published by Craig Iskowitz, founder and CEO of Ezra Group, a boutique consulting firm that caters to banks, broker-dealers, RIA’s, asset managers and the leading vendors in the surrounding #fintech space. He can be reached at