We have reached a milestone! This is the tenth interview in our Winners of WealthTech series, where I speak people who have made their mark in wealth management technology by building a track record of innovation and success.
Check out my previous interviews with Anil Arora, CEO, Envestnet | Yodlee, Angela Pecoraro, CEO of Advicent, Eric Clarke, CEO of Orion Advisor, Bill Capuzzi, CEO of Apex Clearing, Lori Hardwick, President of Advisor Innovation Labs, Cheryl Nash, President of Fiserv Investment Services, Stuart DePina, President of Envestnet | Tamarac, Bill Crager, President of Envestnet 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 firstname.lastname@example.org.
I’m excited to present this month’s Winner of Wealthtech, Brian McLaughlin, CEO of Redtail Technology. Brian founded Redtail back in 2003 and has grown it from a tiny startup to the number one vendor in the advisor CRM space with over 100,000 users.
Brian was named to the 40 Under 40 List in Financial Advice Technology by Investment News in 2015.
Why did you start Redtail?
Brian: I have always had a passion for the creativity of programming. My first job was at a small broker dealer and OSJ and I was working on solving technology problems for them such as synchronizing data and building tools to track prospecting opportunities and so forth.
I really enjoyed it. It just kept taking me more further and further down the path of building technology solutions for financial advisors. I just got hungry to find ways to solve people’s problems. It was similar an artist or something like that. When you’re a programmer you have the ability to design and build anything in your mind for solving people problems, it brings a lot of personal satisfaction.
Craig: Do you have a degree in computer science?
Brian: I don’t. No, this is just something that came naturally. I just enjoyed it.
Craig: What made you pick CRM?
Brian: I don’t think I chose CRM, it was more like CRM chose me! It was what was needed at the time and what I had an opportunity to build. I had a job that was paying me to solve problems like that. We didn’t start off building a CRM. It just grew into that over a couple of years.
I remember back around 1999 at the OSJ when we were shopping for CRMs, but there weren’t many great solutions. I remember volunteering to the business executives there and said, “I can build this.” And we wouldn’t have to spend the money and get a half-baked solution.
And they only gave me a week to do it. But anytime someone challenges me, I’m pretty competitive and that just pushed me to try and build something that’s impossible. That was the beginning of how I got into CRM, due to a business need.
What are some of the things that have become more important to you personally over the past few years?
Brian: I’ve spent 15 years building this company after just imposing myself as the CEO. When we were small, it was easy to be both the CEO and a programmer. It’s no problem when you have 20 or 30 staff members. In the last five or six years we have tried to develop business leadership skills and have also put a lot of energy into culture building.
One of the most important things to me about Redtail and the key to our success internally is that we have a very strong company culture. Of course, everyone knows the dog (company logo). But also we have a community within the organization that’s starting to get more and more stronger.
We are trying to find other people’s passion so that we can feel their passion to be great. For me it has been a lot of learning on that front. How to take off my programmer hat and sit down and look at how people actually interact with each other, what are their passions and how can I grow their successes?
Craig: Do you feel that it’s changed since you were in school? Were you forced to do more things outside of your major versus kids coming out of college now? They seem to focus just on one thing and they come out without really understanding how other people think. If they’re programmers, it’s difficult for them to think about how they would do something rather than understanding how the users would do it. So, you are looking at it from a user’s point of view, which is more difficult as your systems become more complex. Are you finding that the programmers you’re hiring now have trouble relating to users?
Brian: Programmers have a hard time seeing the business when they’re working because programmers can be perfectionists. They love structure and organization and that’s how they code. Programmers today are very task-oriented but we try and get them out of that box.
I think I have an advantage because I can see both sides. I was motivated to grow a business and I had the unique abilities to be able to code my way out of problems when they happened.
One of the things that we are doing here a couple of years ago was the concept of an innovation team. The goal is to encourage people to think creatively for solutions that don’t have to be revenue-generating. We want them to think outside their daily task work and look at things a little differently.
I just had a meeting yesterday with a really fantastic group of our data engineers and we challenged them to find new ways to repurpose our data to improve the daily lives of advisors. And I guess a part of our job as leaders is to challenge our people to take more advantage of the potential they have. They should avoid getting stuck in a task mentality.
Craig: Is there anything that’s come out of the innovation team that’s really changed the way Redtail works or the way customers work with it?
Brian: Yeah, the biggest one has been our Redtail Speaks product. (this allows advisors to communicate with customers via text messaging in a compliant manner.)
Craig: I didn’t know that.
Brian: Yeah, that was an innovation project and then it was tied in Orion’s Fuse event (their annual weekend hackathon) which gives a great platform to kind of showcase something we were thinking about and to weddings. And again, thankfully, a couple of years later it actually turned into a product.
So, we’re also innovating in other ways that aren’t directly related to CRM or any current product features. We setup an Innovation Team to work with 3D printing technologies like Mini Maker or Maker Faire which are linked to local schools’ STEM programs for students of all ages. And they actually built this really cool, 3D terra forming sandbox that’s being installed at a local children’s museum.
And people get these days and see projects completely unrelated to of work every day. But it benefits children of the day.
How would you describe Redtail’s culture and how do you feel that helps move the company forward?
Brian: We live by one big mantra, which is “build raving fans”. Every employee here knows that’s our number one objective. And it’s not only customer-facing it is also employees-facing where we make raving fans out of all the different teams and personalities among the different groups that we have within the company.
Living by a couple of basic rules really helps define a culture and an organization. People know what to expect from their leaders and they know what to expect from the company’s direction when they make a decision when you have well-defined ethics.
How do you identify people who will be a good fit for the Redtail culture?
Brian: That is interesting for us. We’re very picky and take our time with hiring and selection. One of our goals is to have very low turnover and keep our employees for 10 years or more. Our very first employee is still working here. She’s now in charge of all customer support.
A couple years ago, we started an interesting idea to bring people into our support team that were temp-for-hire. The support team is one of the toughest groups to work in so it gives us a chance to understand them better and see if they’re a cultural fit. It is also an opportunity for them to make a decision if they like us, so it has to be mutually inclusive.
And if not, then we have an opportunity to let them go find a place that fits them better. Or maybe we absolutely love them and want them to be part of the team, let’s bring them up full time and move them into another part of the organization.
All of our job postings are started internally first. We always hire internal first and bring people up through the ranks, usually through support or human resources.
How do you stay motivated after running Redtail for 15 years?
Brian: I guess it’s the challenge of all. That’s how we started it, it was a challenge. We were bootstrapped organization. We’ve never taken money from anybody and I was looking to pinch pennies and stretch them. And every day is another challenge, every day is another opportunity to solve a problem or make somebody happy or do something good for the world.
There are consistent challenges that come from running a business like this. This would wake me up even if I saw no one every day. I don’t feel like I’m working. I think that’s the catch. I don’t feel like it’s work. I feel like it’s a passion that I get to do every day. I don’t count hours so much like that. With the software business, there are so many things we can do, it’s never ending and it’s fantastic. It’s always something new and fresh.
What‘s the best advice you can share about how to launch a startup software company?
Brian: You better have a crazy amount of passion for it because you’re going to spend your life doing it. It’s seven days a week, 24/7 especially in the beginning. Actually, it’s more like 24/7 forever. You’re going to have to figure out different challenges that are harder than just an employee in an organization where you have to figure out things like work-life balance and all that stuff.
Those challenges are going to be harder for a business owner. If it’s not something you love, you’re never going to succeed at it. You might have a great run in the beginning, but you’ll get exhausted and it will start breaking down. But when it’s something you have complete passion and love for it never stops and you just keep going. Then your family and your friends and everybody else feels it with you.
How do you maintain your work-life balance as the CEO of this fast growing start up?
Brian: Yeah, it is definitely a challenge for me. I have a wonderful support group at home that helps. I think a lot of it is just scheduling, for me, probably. We are moving really fast in this organization and that makes it challenging to take those breaks. One great advantage that think we have is one of our slogans “work where you want”. I try to take advantage of that as much as possible. So it’s common for someone to be working somewhere else remotely, and by work it could be a simple idea like being available or doing phone calls or meetings or whatever. But I’m not required to be here.
One of my goals and my objective through the last few years has been to get my leadership team in a position where I don’t have to necessarily be in the office every day. Operational and strategic decisions can be made by a team and by their council of leadership and work on solving problems and only bring me in as needed.
Craig: How’s that working out?
Brian: It’s getting better. It’s a work in progress. I have a fantastic leadership team. I’m really lucky to have a strong people that can run this organization. We’re pretty flat management structure with only six directors who report to me. People operate the company and now they refer to me and we fill up you know a lot of times you know team building and so forth.
We’re a cohesive team. I try to empower them to make smart decision to be able to free up my time. The thing about the bigger picture things, so that’s the work in progress, we meet on a regular basis. For us communication is constant, it’s not scheduled, it’s just learning every day. So, everybody is in the loop, everybody knows what’s going on. And of course, like most companies we have an open door policy and people feel free to speak their minds.
Some of the directors, like the gal who runs people operations, have been working with her for almost 20 years. A few other ones, like Allison is the head of support, and she has been here for 13 years. So, we have had a long run with these people and they know me very well.
When you get up in the morning, what is your morning routine? What do you do in the first sixty to ninety minutes of your day?
Brian: Well first of all, I am not a morning person! I am a night owl. First thing I do is check what went on overnight. Then it’s coffee, hang out, chat with the family to see what’s going on with the game plan for the day.
That’s just like what today was. I generally go into the office around 9. I’m a late starter. I’m not like other people. I read all those articles about people who get up at five o’clock and do their exercise routines, but that’s not for me. For me, all of that is shifted to the evening, so I usually roll out of the office around 7, pretty late in the day.
Craig: What’s your evening routine?
Brian: We do family dinners and all that kind of stuff. Actually, the answer is that I don’t have a routine.
Craig: Your routine is no routine.
Brian: Yeah, the routine is whatever feels good for that day.
Craig: It gives you a lot of flexibility.
Brian: It does. It gives me the opportunity to do whatever the day calls for. Sundays off or getting out early and taking the family out to a movie, a play, to a lake, or whatever. Some nights I stay here [at the office] and we have a video game session with a whole bunch of people. Whatever the day calls for.
Craig: It sounds like fun.
Brian: We trying to have a lot of fun here. It’s hard work. It’s hard to do the jobs here every day and so we try to unwind every now and then. Yesterday, we set up badminton and volleyball courts in the backyard, which is a piece of property behind our office. I would say we probably spent a good couple hours with different groups going out there and playing games and having fun. We’re here to enjoy what we do and that requires breaks and things that take our minds off of everything.
Craig: That goes back to building the company culture.
Brian: It does. People have their dogs here and we have an annual Zombie Attack War and things like that. Last year we bought and renovated an old building here in Sacramento. And when we built it, we have almost no offices, it’s completely open until we open and we built a lot of great places for people to hang out and socialize. And not so much for them to go to meetings. We built it for more open collaboration and that helps our culture as well.
And it’s National Bring Your Dog to Work Day and we have like fifteen dogs here today.
What would your close friends say that you are exceptionally good at?
Brian: I think I’m especially good at running an organization that cares for people. Our advisers, our customers, our staff. I’m also exceptionally good at being organized. I’m a pretty detailed person and it comes from being a programmer and stuff like that.
Who was your biggest influence when you were growing up?
Brian: Probably my parents. There are pieces that I remember growing up that have stuck with me forever. My dad in particular. I’ll tell you a quick story. I remember we had a hardware store in Mill Valley, CA just across the bridge from for the bridge from San Francisco. My parents are divorced and in the summers I would go and work with him in the business.
We used to deliver barbecue, Weber barbecues, to people in Sausalito with all fancy, cool homes. I’ll always remember driving with him down by a beach area on a Tuesday afternoon and there were all these people playing and kite surfing and wind surfing. I asked him how they can do that on a Tuesday afternoon? Don’t they have to work?
And his reply was that the goal in life is to find something that we love to work at and can make money doing so that we can enjoy the luxury and make free time for us. And we have to pay attention to the career and the work that we do and the earnings we make will enable a life like that. This drove me to work hard and build a business that would give me flexibility.
My mom was a single parent and she just recently retired. But she worked her butt off to send me to Catholic school and take care of every need when I was a kid. She was very active in my life, in the community and my social life, between church and the Boy Scouts, which was a big thing for me.
She showed me the characteristics of how to love, share and build a community and how important that is. Boy Scouts was a big thing for me and taught me a lot of lessons about life. I remember that I got to a point as a teenager where I said, “I’m not doing this Boy Scouts thing anymore.” But she kept pushing and pushing and saying “you are going to finish Boy Scouts and become an Eagle Scout”.
And I did.
At 17, I became an Eagle Scout. It was really hard for me in high school to get through it. But when I reached that goal and realized what I had achieved, I thought, “Wow! That was amazing!”
I’m so glad I did! “Thanks, Mom, for making me do it.”
Who do you think of when you hear the word successful?
Brian: I think of all the big names in our industry. Like Eric Clark (CEO of Orion Advisor) or Aaron Klein (CEO of Riskalyze). They’re a lot closer to me than some giant celebrity.
I probably relate more to a Steve Jobs-type personalities as successful. Hard work and creativity and drive. That’s one of the great advantages of being a leader in our space. Being connected with these amazing people that have different stories and different lives.
Watching people like Aaron Klein adopt children and then how he balances his family with the challenges of growing a business. It’s amazing to me watching Eric Clark working in the family empire and how he’s built an incredible company culture.
What bad advice do you hear being given out most often?
Brian: Saying that you can’t. That a problem can’t be solved. I believe anything can be solved if you put your mind to it. It’s bad advice to say that you can’t do it. Whether it’s in life or work or whatever you just have to figure out what the solution is for you.
“You can’t learn this or you can’t learn that,” it’s bullshit. You can actually learn to do anything you want. You just have to be passionate and you have to be interested in it. You have to want to do it and you have a reason or want to be or you’ll do anything in life.
Do you have a favorite smartphone app that you found recently that you find it helpful and makes you more efficient?
Brian: You know, for me is, I live on Slack and we use it heavily. I use a lot of Evernote for note taking and stuff like that. It’s a very simple app.
Craig: I’m typing in Evernote as we speak.
Brian: I keep Evernote on my front home page there. To keep me on task, I benefit from an amazing executive assistant. She’s worked for me for a number of years.
What’s the kind of book you give as gifts?
Brian: I don’t really do that very often. Although, the other day, I did give out a book called Getting Things Done, by David Allen. Most people know that particular one.
Craig: What about for yourself? Do you read a lot of books?
Brian: No, not business books. Because I’m a programmer, I lean more towards technical stuff. A lot of blogs.
Craig: What technology blogs do you read the most?
Brian: Mostly stuff about Ruby on Rails, which is the programming language we use for Redtail.
Craig: I have a computer science degree, but I never learned Ruby on Rails. I moved away from programming way before that came out.
Brian: Back in the day, we were a Microsoft.net shop, which was the first enterprise language that I learned and what the original version of Redtail was programmed in. Around four years ago, we switched the whole company over to Ruby and Rails and re-wrote the CRM code. We also do a lot of stuff with Amazon Web Services and we’re doing a lot of learning on that front.
And about six months ago I bought a Tesla, so now I’m totally geeked out on electric stuff.
Craig: I haven’t done any programming in years, but in my business, it’s quite helpful to understand both the technology side and understand how things are put together as well as understanding the business side. I can relate to your comment about programmers not understanding the business. I know it took me a while to get to a point where I felt comfortable moving back and forth between the two worlds.
Brian: Yeah, as a programmer I had to learn things for Redtail. I had to learn how to do budgeting and finance, of which I had no real knowledge or experience. It took a couple of years to really get up to full steam. Now we have a CPA who works for us, but I still have to know it.
One of our board members actually was the one who pushed me to learn the other parts of the business like hiring practices, legal and human resources. It’s also about surrounding yourself with people who are experts in these areas.
Craig: Were you a self-taught programmer?
Brian: I was.
Craig: Learning programming in the ’90s was very different than learning programming now.
Brian: Not even close, it’s so different. I remember I was sixteen when my mom got me my first computer. She had to save a ton of money for it because it was very expensive back then. It was PC clone in a big old beige box with a modem that was built from parts by a friend of ours in his garage. The thing probably weighed 50 pounds and had a crappy monitor. I think it was running Windows 3. I might still even have it.
Back then, you would geek out and run down to CompUSA or someplace like that and you’d buy the new reference card or we’d double the RAM virtually using Stacker software.
Brian: The first programming that I ever really did was in Qbasic. You’d build a menu system, press 1 to do this and it would launch a program. I kept tinkering with computers and programming for a while. Then when I moved to Sacramento for school, my first job was an entry level position at a financial services company. Two days or so before that, my future business partner, Andy, had been hired as their director of I.T. We hit it off right away and developed a great working relationship.
I was just happy to be getting paid for programming that I would have been sitting at home and doing for free.
Craig: I was a big Visual Basic programmer for a while in the early 90s. I used version 1.0, I was one of the beta testers.
Brian: Yeah, we started back when Microsoft.net first came out. I pushed from ASP scripting right to .NET right away. The version 1.0 beta and never looked back. But I never made it to C#.
Craig: I was the same. Anything that needed to be compiled, didn’t appeal to me. So I migrated to Visual Basic and stayed with scripting languages until I moved away from programming altogether.
Brian: Thankfully, there were smarter people than us who built those big application programming languages that required compiling.
Craig: Yes exactly. If we didn’t have those guys I don’t know where we would be.
What message would you send back to your 20 or 25-year-old self?
Brian: Think bigger. Just think bigger.
Brian: When you’re 20-something, I feel you’re working in the moment. You have a much narrower focus, you’re not seeing the bigger picture of what you can do and what you can achieve in life. I loved learning and geeking out on programming, but I wasn’t looking at the big picture stuff.
I probably could have moved faster when I was building Redtail or done a dozen other cool things early on. If I had only taken the time sit down and maybe find a mentor and learn how companies are built. Working hard was not the issue since I was working 100 plus hours a week.
When you’re young, you have all the energy in the world and all the time in the world and no family. So I wish I’d seen or had been taught what I could have done with my skills.
What was your favorite failure? The one that you learned the most from?
Brian: There are too many. My favorite failure, one of the tougher ones for me was probably learning empathy. In my 20’s when Redtail was just staring and we hired our first employees, my mentality was that they were just objects that the business needed to operate. I didn’t see them as having a personal life or their own stories or families or anything outside of work.
And I think from being a programmer made me treat things as binary. Either 1 or 0, on or off with nothing in between. So, I don’t have one specific failure, just a number of experiences over time that helped me to learn empathy for other people. I wish I had learned that much earlier in my career.
Craig: Was there a specific project or task or confrontation that resulted in your realization that you needed to learn to be more empathetic?
Brian: The one that I had most in my mind, was when we were a small organization, it was difficult balancing professional life and friendships, especially if they are employees. There have been a couple of cases in my life and in my career that I didn’t balance that as well as I could have. I used those as a learning lesson for me.
Do you have a favorite movie?
Brian: Top Gun.
Craig: They’re remaking that.
Brian: I know, thank God! Finally! It only took them 30 years or something like that.
Craig: It’s going to be Top Gun in the old age home.
Brian: I saw it when I was 12 years old and it was the coolest thing ever.
Craig: It still works.