Winners of WealthTech: Aaron Klein

This is the second post in our series called, “Winners of WealthTech.”  I conduct interviews with influential leaders in the wealth management technology space who I believe are the winners.

The format of these article is a bit of a change from our usual analysis, product reviews or industry trends.  The questions are more personal in nature because we’re trying to discover the habits that have helped to make these leaders successful.

I was inspired to start this by one of my mentors, Tim Ferriss, who is a best-selling author, 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 on Amazon or even in a brick and mortar book store.)

Our second interview is with Aaron Klein (@AaronKlein), co-founder and CEO of Riskalyze, a provider of risk profiling, compliance and digital advice tools for financial advisors and institutions.  Founded in 2011, Riskalyze has 183 employees and over 19,000 users of their platform. Aaron has led the company to twice being named one of the top 10 most innovative personal finance companies in the world by Fast Company Magazine. He’s also been honored by InvestmentNews as one of the Top 40 Under 40 in the financial planning industry.

What has become more important to you in your personal life over the past few years?

“I would say focusing on my relationship with my wife and kids. One of the things that I’ve had to realize with this job is that it’s intense and so I really had to work to minimize my outside commitments other than family and work. That’s my dual mission.”

I was serving on an elected board for my local community college. I did that for twelve years and I loved that work. But I said right now is the time to focus on work and family.  To me, that’s that’s become the most important thing. I’ve got three kids who are thirteen, ten, and eight and I’m not going to get those years back and these are important years in my career, too, so I’m just going to focus on those two missions.”

ISK – One of the other areas that is important to Aaron is giving back.  In 2010, Aaron and his wife, Cacey, helped to found Hope Takes Root, a local effort to build a revolutionary community to foster, care and adopt orphans both at home and around the world.

ISK – Aaron built and sold two other companies before co-founding Riskalyze, which led me to me next question.  

How do you stay motivated (after so much success)?Winners of Wealthtech

“You know on those on those days when it’s tough, I got to tell you, like the number one thing is that we’re a company that was built with a mission.  And when it’s a mission bigger than making the next dollar, that makes all the difference in the world in keeping me motivated. I think that there’s an impact on our team, as well.”

“Our mission of empowering the world to invest fearlessly is one that we really believe in and we really believe is going to change the world. That’s a really motivating incentive to come to work every day. It makes me excited.”

ISK – This is a catch phrase that Riskalyze is now using, ‘Helping Advisors Empower Fearless Investing’.

AK – “It’s literally our mission empowering the world to invest fearlessly because our belief is if you can help somebody understand how to react to risk appropriately in the short term and make good short term decisions that’s how you turn a fearful investor who makes a bad short term decisions into a fearless investor who makes really great short term decisions that protect their long term financial goals.”

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

“I promise this is like the last time I mention Riskalyze. Here’s the thing that I believe is true that most people would think is crazy.  I believe that the risk number will be at the heart of the world’s investing decisions in the future.”

“Understanding and reacting appropriately to short term risk is the right framework for the world’s investing decisions. Whether that’s talking about an individual, whether that’s talking about a couple, whether that’s talking about a pension fund an endowment, or a foundation. I really believe that if we understand risk correctly, that we make better investing decisions and what we’ve built is pretty multi-layered and we’ve delivered just the first few days of the innovation that we’re going to deliver to the industry in the future. It’s our belief that the risk number’s going to be at the heart of the world’s investing decisions in the future.”

What is your morning routine?  What do you do during the first 60-90 minutes of your day?Winners of WealthTech

“Well that’s an interesting one, because I just analyzed my calendar and I traveled 48% of my working days in Q2.  That’s pretty consistent quarter to quarter. The routine changes a little bit, but a standard day is a 4:45 A.M. wake up call. Do some coffee, do some e-mail, hit the gym, hit the office. Three years of almost nonstop travel sort of takes its toll, so I started working out with a trainer.” 

“They, for some reason, won’t come in before 8 am.  So, I start working from my home office for a three-hour shift and leave there at 7:45 and hit the gym. I can take my kids to school on the way there, which is kind of cool, and then hit the office a little bit later, but but that’s what it looks like for me.”

ISK – But what do you eat for breakfast besides coffee? 

AK – “I have to force myself to eat breakfast. I’m not a huge breakfast eater. But honestly, you can make me happy with a bowl of Cheerios.”

ISK – What do you eat that makes you feel most productive?

AK – “It’s probably a bowl of cold cereal.”

ISK – Is that because you have kids and that’s what usually around the house?

AK – “That’s what’s usually around the house, yeah. If you find me in a restaurant, it’s a two eggs and some strawberries.”

ISK – I’ve listened to interviews with a lot of successful people and it seems as though the ones with military backgrounds are early risers and often have just coffee of skip breakfast entirely.  People like General Stanley McChrystal (Ret.) and former Navy SEAL Jocko Willink.

AK – “I found that if I go work with a trainer and I haven’t eaten something for breakfast, those workouts are intense enough that I will feel nauseous halfway through the workout. So, I’ve got a fuel myself to be able to do that. But that’s interesting, I’ll have to think about that for some days.”

What new app have you found recently to be helpful or made you more efficient?

“Not too long ago, I switched myself and my direct team to Todoist, which is task management, but it works with teams. The thing I love about it is that it is absolutely 110% consistent across all platforms.”

“I jump between devices all day long. I’ll be walking through an airport and triaging stuff on my iPhone. I will use my iPad for the first half hour, forty five minutes of any flight. And I’ll use my Mac all the time and then sometimes I just need to log on over the Web, maybe on my wife’s computer for some strange reason. Well Todoist looks and works identically and you can do everything you need to do across every single platform no matter where you’re at. I just love that because I was stuck with some other products where their mobile app didn’t let you do half the things that their website did.”

ISK – How does your staff like it?

AK – “They like it a lot. They now can triage stuff for my day. As important stuff comes up. they have the ability to put it on today for me and that’s a really cool asset to have.”

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

“This is an interesting one. This is probably your question that I had to think the most about.”

“Once you have a basic level of success, I think that you realize that beyond making some money, real success is about building something bigger than yourself. I’ve got to point to Ben Horowitz. Who is the second half of Andreessen Horowitz, the venture capital firm in Silicon Valley.” 

“It’s because of his past work. He’s one of my heroes just from reading his book, The Hard Thing About Hard Things. Because despite a ton of adversity and competitors going bankrupt, he ended up building a company that people absolutely loved working at. Eventually, he delivered a great outcome for his shareholders and for the people who entrusted him with their careers. “Then they sold to Hewlett Packard for like $1.6 billion dollars. So, it’s an amazing story and to me that’s real success. When you can go through adversity and figure out how to get your people to the other side.”

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

“This is an interesting one as well. I would say, it’s people almost trying to copy Google to some extent. They’ll say something like, ‘you can run a business solely on a data-driven approach’. I think it’s a misnomer that Google is run solely on a data driven approach, but people sort of say that.”

“We love making decisions at Riskalyze based on data. But as Ben Horowitz would say, ‘running a business solely by numbers is a lot like doing a paint by numbers painting’. Ain’t no masterpiece ever created from paint by numbers. The qualitative does matter.”

“I think that’s probably the bad advice that I see out there all the time.”

“There’s very important uses of data in making decisions. You can’t make good decisions in business without data. It’s just that you can’t make all your decisions off of data. I’ve heard people say, ‘you can’t A/B test your way to an amazing product.'”

ISK – Many entrepreneurs are perfectionists.  I heard an interview with Reid Hofmann, the founder of LinkedIn, who was discussing his 10 Rules for Entrepreneurship.  One of them is, “Launch early enough that you’re embarrassed by your 1.0 product release.”  What do you think of this advice?

AK – “I think that’s generally right.  It’s also a perfect example of something that’s qualitative that you just cannot quantify with data. What is your embarrassment quotient about this product?  It’s impossible to quantify that.”

AK – “But it’s it’s absolutely right and I will tell you, for me, there’s a second half to it, which you can only do this second half by getting out there and it’s hindsight. But the second half is if you put out a product that you know you can see the rough edges, you can see what needs to be sanded off, and you can see what needs to be improved. But then the reaction from the marketplace is white hot. That’s what we found with Riskalyze when we pulled our product out of beta in early 2013 and shipped it. There was a ton about it that was that was raw and very rough around the edges. But we knew all of that and we chose to ship it because it we felt it was time and the market reaction to it was so intense and so positive that in hindsight it is what told us that we were onto something.” 

AK – “Because if it has imperfections and the reaction is that great, imagine what happens when you start standing off those edges and you go deeper into the bell curve of adoption and get to those customers who only buy mature products? You’ve got to get that customer reaction or you’ll build stuff that the market doesn’t really want or need.”

AK – “So that’s a really good question because the risk was it was a start at one point and now it’s your company now you’ve got thousands of clients.”

How do you maintain the entrepreneurial spirit in order to avoid The Innovator’s Dilemma?

“That’s a that’s a great question.  You know as much as that is true, we’re still a company of one hundred eighty three people. We expect of our people that we will be more flexible, more nimble, and more innovative than a lot of our counterparts in the industry.”

“But I think a big part of that is simply being willing to do new things that might even threaten your disrupt your core business. Now that we’ve got a pretty sizable core business, we find ourselves stuck with those kinds of questions and decisions all the time. We’ve got a lot of research projects going on deep in our labs. You know if somebody invents a better way of understanding an investor’s risk number and that makes our risk questionnaire component of our product obsolete? Well, so be it! We’re going to ship that and it might be a little painful in the meantime, But we’ve got to be willing to go through those kinds of transitions if we’re going to ensure that we build that long term independent partner, the one hundred year company, that that we’ve always said we were setting out to build.”

Who was your biggest influence when you were growing up and why?

“I was thinking about how it wasn’t incredibly tough for me to figure out the answer, but it made me think for a minute. Why do I say my dad when I say who who was my biggest influence? So it’s true. I did I started working for him at the age of twelve. I joke that he knew nothing about child labor laws or minimum wage laws but it but it worked out.

“You know the really interesting thing about my dad is that the industry that he knew was changing dramatically over that point in time. There was a lot of consolidation going on there were shrinking margins. He was in wholesale distribution for automatic gate and security equipment. This is like where I first learned the core concepts of business. At twelve, fourteen, sixteen, eighteen years old.”

“I’ll just put it this way. First of all, it’s probably what gave me my love of technology businesses. Unlike technology businesses, we were dealing with 18% gross margins with a commoditized product that you could get anywhere. So it was all about relationships and it was all about velocity. I think that’s played a huge role in how we’ve built Riskalyze’s customer success team because we believe relationships matter more than just about anything.”

“The other big thing that my dad taught me was, ‘Never give up.’ He fought through so many setbacks in that company. He fought through so many massive industry shifts and so many hurdles with customers choosing a more well-funded bigger competitor who could keep more stuff in inventory. He was just relentless and never, ever, ever gave up.”

“He didn’t get rich off of this company. But he provided great jobs for a bunch of people for a long time. Then he made some money off of it when he sold it to a larger competitor.  I helped him negotiate that deal in 2002. To me, that was a huge success and it just proved the virtues of that grit that he showed of never ever giving up and just putting your head down and fighting hard for every customer and every relationship.”

Is there a quote that you live your life by?

I would say what I strive to live my life by is, ‘There is no limit to the good you can do if you don’t care who gets the credit.’ That quote is attributed to both President Reagan and Ralph Waldo Emerson. But the funny thing is I don’t think either of them care who gets the credit for that quote.”

ISK – According to a website called, Quote Investigator, this quote first appeared in 1863 in a diary entry of a Jesuit Priest named Father Strickland.

What book have you gifted most often?

“Right now, I have five copies of this book sitting here on my credenza and I give them to any employee who agrees to read it and send me back a paragraph on what they love the most about it.”

“It’s required reading for my entire senior leadership team. In fact, we’re having a dinner soon to talk about the book. We’ve almost turned it into a book club internally.”

“The book is Extreme Ownership by Jocko Willink.”

“He’s amazing guy. Navy SEAL. I got to tell you, I think most business books are just B.S.. Most of the business books that I’ve read, in the first chapter in there might be an interesting nugget there. But then there’s fourteen more chapters which were required in order to get the $24.99 price for the book. But this book is incredibly. The principles that Navy SEALs use to execute their missions have such applications to our world in business. I’m a huge fan of of Extreme Ownership and I’ve been gifting it a ton.”

ISK – One thing I remembered from Tim Ferriss’ interview with Jocko was about discipline and using everything to your advantage. When I went back and looked it up, the quote was actually from a different SEAL, but is still memorable, “I think it’s hilarious when some [special operations] guys get grumpy if they don’t have protein powder every 2 hours. I have a huge advantage if I can turn anything into fuel, including garbage, or go without food.”  The concept is that you build up your own discipline in all aspects of your life, including eating, in order to outperform.

ISK – Now I know why Aaron sets three different alarm clocks.  It’s a tip from Jocko who says, “Two is one and one is none.”  When you have two of something and one breaks, you’re left with only one and no backup.  So, if possible, you want three of everything.  That way, even if one breaks, you still have a backup.

AK – “Jocko has a whole chapter talking about discipline. He says, “You can’t control all these different things that are going to happen, but you can control when you set your alarm for the next morning.”

How would you describe Riskalyze’s culture?  How did you maintain it during your rapid growth?Winners of WealthTech

“We have had like tremendous ramps of growth and that’s been a big challenge of ours that we have tried to be incredibly intentional about. We thought about it and we struggled for first two years while we were doing R&D on the core technology since our initial strategy for monetizing it was not working out. We weren’t planning to go build an advisor product until like 2015 and we ended up basically saying, ‘well look, if we’re going to go down let’s let’s let’s die trying! Let’s go down swinging!’ 

“So we rebuilt the product for advisors and it just exploded and the company started growing like crazy. We found ourselves in probably June of 2013 with all of a sudden needing to start building a company around the startup that had struggled. I think that most startups that struggle, if they make it, although most of them don’t, but if they make it they usually have this motley collection of B and C players and they’ve got to build a company around that. We look at them said, ‘Oh my gosh, we’ve got six hard core A players here,’ in June or July of 2013. And so we said, ‘All right, well our mission our job is to make sure that we just don’t screw this up.’ So we instituted a mission and values training that I still teach. I teach it personally. Not by video. In person to every class of Riskalyzers that come aboard.”

“It is it is what has allowed us to be the same organization when we went from 6 to 11 at the end of 2013 and then 11 to 25 at the end of 2014. And then, we went from 25 to 70 and 70 to 90 and we’ve gone from 90 to 183 people since last October. The way that we’ve stayed the same organization is we’ve been very intentional about training our mission and our values. If you look at our culture, it’s exemplified by our values that we really live by and we talk about and we actually operate by all the time. I would say the hallmark of this is of our culture is:

  1. We’re not about just doing what our customers want, we’re about listening to them but we’re about having a vision of where our industry should be and and building what we believe will delight them rather than just doing what they want.
  2. We’re a high feedback culture with very open and direct communication.  But you have to do it with respect. We have a firm ‘no jerks’ rule. We empower every single Riskalyzer to walk up to somebody else and with utter respect say, ‘hey look, that needs to be better or you’re going to screw up our company. I know that that’s important to you as much as it’s important to me.’ And that kind of teammate to teammate accountability and teamwork and communication has allowed us to ship the products that we’ve shipped and build the company that we’ve built and still be that same organization that we were back in 2013.”

What message would you send to your 20 yr old self?  30 yr old self?

“At twenty, I was just starting to move on from my dad’s business and I ended up starting a company, it was moderately successful. Then I started another company, but it was not very successful. I learned a ton of things from those two experiences. In hindsight, if I could send a message to my twenty-year-old self is ‘find someone building something great and go to work for them and learn from them. It’s the cheapest education ever because they’ll pay you to do it.'”

“Thirty was not too many years ago. Riskalyze is like six years old, so that’s two years before that. I would send a message to myself that risk is going to be really big!

What message would you put on a billboard?

“Do you know you know your risk number?”

How do you identify people that would be a good fit to work at Riskalyze?

“I would say we look for three things. First of all, we’re looking for a combination of I.Q. and E.Q. We need smart people and we need them to be people who can relate to other people. Because relationship is so important in business when you’re fighting for every customer. Second, we look for ability to handle our high feedback communication culture. If you come from a blame-based culture we’ll still take a risk on you, but but we need you to demonstrate that you can make the transition and not turn that into political behavior where you’re trying to play “Game of Thrones.” 

“The third thing is courage. And this is a really hard thing to interview for and figure out. Courage to me is about having having the willingness to make the right decision even when it might cause some short-term pain. Having the willingness to make a decision when none of your options are really all that good.”

“To me, that’s that’s really what courage is all about. I say to every class of Riskalyzers that I welcome in mission in values training, ‘We’re looking for leaders here. I can’t tell you how big our company is going to get. But I need you to be the leaders of our company tomorrow if we’re two or three or four times our size.’ And sure enough here we are with 183 people. Well we’ve got 90 people who took that very seriously a year ago and we’re building them up as leaders. If we’re not building leaders who have the courage to make great decisions, we’re not going build scale as a company or as an organization.”



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