Ever Onward Podcast

AI That Strengthens Human Relationships with Travis Hawkes & Aaron Klein | Ever Onward - Ep. 136

• Ahlquist. • Season 1 • Episode 136

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In this episode of Ever Onward, Tommy Ahlquist and Travis Hawkes sit down with entrepreneur and AI founder Aaron Klein to discuss what it really takes to build a successful company, create a strong culture, and lead through constant change.

Aaron shares his journey from working in his father's business to building Riskalyze into one of the financial industry's leading technology companies, achieving more than 42 consecutive quarters of growth before its acquisition. He reflects on the lessons learned through failure, hiring, leadership, and scaling a business while staying true to a mission-driven culture.

The conversation then turns to artificial intelligence and why Aaron believes AI should strengthen human relationships—not replace them. As the founder of Contio, he explains how AI can eliminate repetitive work, improve collaboration, and help professionals spend more time doing what matters most.

They also discuss:

  • Building and scaling a startup from the ground up
  • Creating a values-driven company culture
  • Hiring great leaders and avoiding common mistakes
  • Idaho's growing technology ecosystem
  • The future of AI and the workforce
  • Why entrepreneurs should focus on the craft—not just the exit

Whether you're a business owner, entrepreneur, technology leader, or simply curious about where AI is headed, this episode offers practical insights and a refreshing perspective on building impactful companies.

🎧 Listen now and subscribe for more conversations with the leaders shaping Idaho's future and beyond.

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Welcome And Aaron’s Background

SPEAKER_02

Today on the Ever Onward Podcast, we have Aaron Klein. He is the founder of Contio. It is an early stage AI company focused on helping organizations capture the value hidden in conversations. Previously, he was with Riskalize, the category-defining risk alignment platform for financial advisors. He served there as the CEO for 42 consecutive growth quarters. He led the company through its acquisition by HG in 2021, and the business was later rebranded as Nitrogen. Aaron continues to serve as the founder and on the board of directors. He is going to be a great conversation about talking about all things AI, the future of companies and venture capital and AI in Idaho. And Travis and I are really looking forward to a conversation with Aaron Klein. For those of you listening to the podcast, please give us a like, comment, and follow below. We really appreciate you listening and to Ever Onward and today's guest, Aaron Klein. Aaron, welcome to the podcast, man. Great to be here. Travis has talked so much about you. I feel like I'm ready to go here.

SPEAKER_01

Well, I pay Travis a lot to do that.

SPEAKER_02

So PR. I'm a PR guy. He is the president of the fan club. Let me tell you. There you go. It's a big deal. Thank you for coming on. Yeah, thanks for having me. Can't wait to hear your story and then talk all things uh AI and everything else in between. For sure. For sure. Tell us

Learning Grit In A Low Margin Business

SPEAKER_02

a little bit about you to start.

SPEAKER_01

Yeah, absolutely. Um, I mean, gosh, I uh my my career in entrepreneurial business, I think started at the at the age of 12 in the afternoons after school working for my dad. You could go earlier. I think I started a detective agency in the park or something like that with some friends, but that didn't work out so well. But uh, but no, no, seriously, started working in the afternoons after school for my dad at the age of 12. It was super interesting. Like uh he had this wholesale distribution company for automatic gates and security equipment and uh you know, brutal business, like 18% gross margins, uh commoditized product. Uh, your only advantages were how much inventory you had, which we had no capital, so we had very little inventory, and and and you know, just the quality of your customer relationship. So I learned a lot of things from him. You know, I learned the grit that it takes to be an entrepreneur. I learned that, you know, relationships are everything in business. Like you take good care of your clients, they'll take very good care of you. And the third thing I learned was that I wanted to be in a much more high margin business when I grew up.

SPEAKER_02

So uh so yeah, I ended up You probably like we just started the podcast, but you could probably say amen at those first two things, right? Seriously, for almost every business. Yeah, absolutely. Absolutely. Tell us a little more about your dad.

SPEAKER_01

Well, yeah, I mean, he's he's he's one of my heroes. He he worked really, really hard for his family, never, never really caught any any kind of massive break, but just you know, built like like like like literally built with his own two hands, like this company that created jobs for people and created livings for people. And um, you know, so so we worked at that and worked at that. I actually helped him sell that company to a larger competitor uh when I think I was 22 years old. I I I you know, again, no, no investment bankers, no business brokers around. I just kind of went out on the road to the five obvious buyers and helped him figure out how to sell that at 22. And uh about that time, you know, the internet had really, you know, uh come up and and started doing some interesting things. So we're we're you know, we were messing around with this idea of, well, at the time, the cloud hadn't been invented yet. So we were messing around with this thing called web-based software, right? The idea that you could make software and deploy it on the web. Uh, and of course now that's that's the only way you do it. Um but at that time, you know, so that that kind of went into a little bit of a of uh I don't want to call it an unfocused startup, but we were trying to figure some things out. And uh we we took we you know built a piece of it that was doing like uh payment processing. We were we were before Stripe, before PayPal, uh trying to, I mean, I think we broke every rule that MasterCard and Visa had ever written down. You weren't you weren't compliant. You beat PayPal, but you just weren't maybe not. I well, I mean it it was actually a pretty decent business. Um there were a couple of things we didn't think about. It's it's kind of interesting. It was for political candidates and political parties. And so uh we, you know, they couldn't get back in those days, pre-paypal, pre-pre-stripe, those kind of things, you couldn't get a merchant account unless you had three years of financials and a business plan. And a political candidate, you know, they're watching John McCain uh raise a million dollars after he wins New Hampshire in 2000, and they're like, I want to do this. This is about 2002. And uh, and so we're we're you know, we we we were building like websites for some of these guys, and they all want to raise money online. And um, and so we're like, we should be able to help them figure this out. So we we didn't know we were breaking all the rules. We just stitched together like probably six different merchant accounts that we had and wrote all the software and wrote all the underwriting, and you know, and and we we were doing that. And uh of course, the only problem was is that political candidates don't raise money during large amounts of the year, right? Because they win or lose and then they go out of business and then there's no business. It's not a great business in some of those years. So uh so anyway, all that to say, we ended up selling that to a larger competitor. Uh, and so that was okay. It wasn't like a huge home run, but it was it was good. And um and we're then we were then trying to make uh you know this kind of like business software but on the web kind of thing work. It was a little early. We also like made a ton of mistakes and like scaled it way before uh we should have. Uh, but ultimately uh that didn't really work out. And so then um, you know, it it was really it's just really interesting how uh life kind of twists and turns and works out, you know. So so that company is not working out. Um and so I need a job, like I got a kid on the way, and I I need to go like figure some things out and so make make a little bit of money. And so I get recruited

Early Startup Wins And Hard Lessons

SPEAKER_01

into this job running product for a division of an options brokerage firm. It's really my first introduction to financial services. And um, and so I'm um, you know, very tough culture at that company, like um wasn't particularly loving life. I had a really good boss, so that was nice. She was she was great to work for, but like uh it was not the easiest company to work inside of. And um, suffice it to say, that was about four years, but I came out the other end of it. I look back now and I, and you know, and and I could not have started the next company without having done those four years in financial services because I just wouldn't have understood a lot of the insights that kind of unlocked the next company. So, you know, two 2011 comes along, uh, and I I've been excited about trying to start a new company uh, you know, for a bunch of different reasons, but uh, but we we we realized that risk was kind of a very I I was I was looking at all these people who were doing options trading. And I remember saying to my eventual co-founder who was a financial advisor, um, I said, Mike, uh, it is crazy how the average individual thinks about the concept of risk. Um, and he said, if you think that's crazy, you should see how us financial advisors think about it. Uh, you know, we just have not had the tools in our profession to really understand how much risk our clients are comfortable with and match that up to the risk in their investment portfolios. Our profession gives us basically three tools a CRM, a performance reporting tool that tells you how things have gone, and a financial plan that says how things are going to be 30 years from now. And the problem is everybody's investing for now, and and they have, and you know, we just use these old wives tales like invest your age in bonds. And it turns out there are 65-year-olds who really want to get enough money for the beach house. Okay. And then there are 35-year-olds who are just, they don't have the stomach to stay invested in the ups and downs of a 60-40 portfolio. And and we can't tell the difference. And so uh from that insight, Riskalize was born. And uh we we started that company in 2011. Uh, the the the first product for financial advisors didn't come out of beta uh until uh March of 2013. Uh came out of beta in in 2013, and and you know, we had meandered around for those two years like trying to figure out we we first thought financial advisors wouldn't buy it because they needed validation. Like who's gonna road test brand new risk technology on their clients? So we did this, we built this thing just for consumers. Uh it it got, it was kind of, I like to call it a successful failure. Okay. The successful part was uh we were in the New York Times, we were in Barron's, we were in NPR. We had uh users come in on our free website and build like $2 billion worth of portfolios, average account size $27,000. You know, they were they were is like your classical e-trade guy that was using it. Um and uh but the failure part was we could not get any of the big brokers that we were going to try to do a deal with to license this technology and fund what we wanted to do to build the advisor product. We just could not get that to happen. Uh and uh so anyway, all that to say, uh we finally just said, you know what, we got three months of money left in the bank. Like let's write if we're gonna go down, we're gonna go down swinging, we're gonna, we're gonna rebuild the product for advisors, and we are going to uh just explain the fact that we have $2 billion of validation from consumers and and and go from there. Um rolled out the product for advisors, took off like a rocket, and then it was just this crazy journey of trying to keep up. Um, you know, we we went from three people to 10 to 25 to 75 to you know 200 employees um serving 35,000 users across the financial advisor space. I mean, the the stories along that journey are just crazy. Like I remember one time we we we finally leased some office space. And I was just like, guys, we have space for 28 people here. Like this is headquarters for life. We signed a three-year lease, you know, we moved out 51 weeks later. We didn't even make it a year, uh, you know, and just like moved into the next building and started and started getting a little bit smarter about our real estate choices. Um, but in any case, what an incredible journey. And then and then sold that company in 2021 to private equity. Um and uh it was, I'm still on the board of that company, uh, ran it for the private equity firm for a couple more years, uh, passed the baton to our new CEO in uh the fall of 2023. And um, yeah, what an incredible journey. 12 and a half years of running that company.

SPEAKER_02

Can I can we go back a little bit? Sure. Because I think I think sometimes people see people like you super successful,

Discovering The Real Risk Problem

SPEAKER_02

had an exit, you know, and and you quickly glossed over those early experiences.

SPEAKER_01

So my wife would say it was a 12 and a half year overnight success.

SPEAKER_00

Yeah.

SPEAKER_02

But I think that's the point, right? Yeah, it 12 and a half year overnight success. Talk about those days, what you learned, how hard it was, and and and a little bit about Travis and I talked a little bit in our podcast we had, that's just the two of us, in the ability to grind through it, not give up, get knocked down a hundred times, stand back up and say, I'm not gonna quit. But then I think what I heard when I was listening to you, you also you also were were were you knew what you wanted, but you didn't know exactly how you were gonna get there on a few of these businesses of what was gonna be profitable and how it was gonna go. And I think that's a real common thread with people that are successful.

SPEAKER_01

Yeah, absolutely. Um I I I've heard it said once um be stubborn about your your big vision, be highly flexible on the specifics of how you get there, right? Yeah, that's it. And and I think that um, you know, we had a vision for uh for for really uh uh empowering the world to invest fearlessly. Uh and I think that uh that that broader vision uh was something that just stuck. And and yeah, we figured out which channel was gonna work. The financial advisor turned out to be the great channel that was gonna work. Uh and and we started scaling that. And then it was just a bunch of backbreaking work to get there. I mean, I made every mistake, I'm sure, in the book. And and that's why, by the way, I decided to start another company so I could make a whole new set of mistakes again, right? But you got to make different mistakes in life, otherwise you don't learn anything. But um, no, but but like I you here's one example. Um, you know, I I had been through that tough organization, and there were a bunch of things I'd written down. I said, you know, um, I don't really uh want to run an organization with these kinds of of problems, you know. Um I Patrick Lancioni wrote a book called The Five Dysfunctions of a Team, right? And I remember reading that book. It's a wonderful book, and I remember reading that book during that time, and I was like, oh my gosh, we have all five. Yeah. Okay.

SPEAKER_03

Living in this.

SPEAKER_01

Yeah, I'm leaving in this book. I'm living in this book. And so I take the book into the office, and I'm I'm gonna date myself here, but like I that we have a photocopy machine still at this point in time, right? So I I copy a few key pages because I have a one-on-one with my boss later that day, and I walk into that uh that meeting, and I just said to her, I said, uh, hey, um, you know, I've been reading this book, and and this is really interesting. And I think you would find it really compelling. Like, I photocopied you a couple of these pages. She's looking very nervously at the book, at the book spine, you know, and the title on the side, and she's like, I hope nobody saw you carry that book here into the office. And I said, uh, yeah, lack of trust. That's one of them. You know, that's one of the five dysfunctions of the team. Great story. Yeah. So so suffice it to say, I had a bunch of things, I had a bunch of PTSD from that. You know, I was very

Riskalyze Growth And The Long Grind

SPEAKER_01

fortunate to have a great boss who she she she was wonderful to work for there. But I left there and I and I was like, you know, if if I'm gonna start a company, not only do I want to accomplish some great things with it, but I also want to do it the right way. And I want to build an organization that that people are really proud to work for and excited to work for. And if you can bring the right talent in and the best talent in, like that's what ultimately drives success. And um, you know, I'm I'm I feel so fortunate that in hindsight, um, that is that continues to be true. Like we have this tight-knit diaspora that is now like all across that industry, which is kind of cool. Um, at a bunch of different companies there, but there's a bunch of risk-lize alumni across all those companies, and we uh stay in tight contact, and that's a wonderful thing. But it it went off the rails a little bit during that time. So here's how that happened. I instituted one of the things, you know, we wrote down all these core values. We had these nine core values that really talked about how we operated, things like, you know, uh how we communicated and how we held each other accountable and um you know, and all these different things. And and I had this list of four four people that I just cannot have in this organization, right? And I still live by this list today. Um, I say mercenaries who don't believe in our mission, uh, jerks who tear down others, um, narcissists who think it's all about them, and people with a victim mentality. That's really my ultimate kryptonite right there. So I just can't handle those four kinds of people. I don't want them. Um I I've made the mistake of hiring all four of those kinds of people before. One time I hired a senior executive who was all four, rolled into one. Okay. But but I what what I did is is I I instituted this thing. I was like, hey, I I approve all offer requests. So even if we have managers who are hiring people, like you don't get to hire somebody just because you want to hire them. Like I'm gonna, I'm gonna screen these people. So I had this thing called the 10-minute veto interview. Okay. And I had to do a video call with any candidate uh before you could get an offer letter for that candidate. And that was that was the rule. So somewhere around 2016, I had a new head of sales, you know, we we're we're growing like crazy. And I have a new head of sales coming in, and he's got a strategy for this massive expansion of the sales team. We're gonna do all this hiring and all this stuff. And um, to be honest, like if I had known more myself at that point in time about like sales capacity planning, I probably would have like looked at that and gone, that doesn't work for our TAM and our market. But nonetheless, I didn't know anything about that. So we're we're embarking on this, on this journey with this new head of sales. And um, and he's gonna do all this hiring. And pretty quickly, I get this um very vehement complaint from a number of people coming from a number of directions. You are the bottleneck, Aaron. Like, I can't get, I'm losing great candidates because I can't get a veto interview on your calendar for two weeks. And, you know, I'm reading all these things about how I'm supposed to scale and I'm supposed to let go and I'm supposed to empower people and all of this baloney, which I I I I barely believe it. Like it's it's it's all got a kernel of truth, but it, you know, I I I learned a very key lesson here. I went ahead and acquiesced and I abolished that process. And that was a huge mistake on my part because what I should have done is I should have replaced the process. And and I ultimately learned that lesson, but I had to learn it the hard way. So here's how it turned out. Fast forward a mere year and a half later, okay. And and you know, we're a high-flying, high-growth company. I used to tell people, people would come to me so frustrated, we have all these problems and they're talking about all these things. I'm like, listen, I get it. Like from the outside, we are Cinderella. Like we are just the Cinderella story. Inside, we got 99 problems, and that one is like 72. And I'm gonna get to, you know, we're gonna get to it as soon as we can, you know. Um, but but we are so we're running like crazy, and we got I I'm just feeling this thing that like I don't know that we have the right, like we, I sense some culture slip. I sense some

Culture Slip And A Hiring Wake Up

SPEAKER_01

we don't have the right people here in some of these roles, and it's just a feeling, but I couldn't really put anything to back up that feeling. And then we were gonna do our first ever all company retreat. We called it Celebration of Awesomeness. And we were busing all of the California employees over to the Bay Area, and then we flew in all the employees from Atlanta and we and and all the other locations where they might have been spread out uh from. And so we're all gonna come together. And so I'm I'm on some trip. I fly into the Bay Area from that trip and literally just land from a trip and I'm walking into celebration of awesomeness at the at the Hilton Garden Inn in Emeryville, California, because that's all we can really afford. Okay. You know, so not very high-flying retreat. Oh, yeah, sure. Absolutely. Um, we broke the elevator four times that weekend. But anyway, um I I walk into the hotel, and there is a guy in sagger jeans um with, you know, uh the chains and the and the neck tattoos and the face tattoos and the piercings, and he looks like he's high. And he's got an 18-pack of Budweiser on his shoulder, and he looks at me in the face and he goes, dude, you're our CEO. And that's when I knew.

SPEAKER_03

That's when you knew there'd been culture slip.

SPEAKER_01

That's when I knew there'd been a little bit of a culture slip. I was just like, I seriously, I'm just, you know, this this guy apparently was like in the Atlanta office. I'd never met him, you know, never, never hadn't been out there since he'd been hired. I don't know. I I my my then chief of staff, she's now chief operating officer of the company, uh, still today. Um, she and I had this shorthand. She would say, we have to let this person go. Uh if if something like that happened. And I would, and I would look at her and I would say, talented jerk or nice idiot? Like which one is it? Right? You know, because because that's typically what we have. And I I I pulled her aside and I said, We don't have a talented jerk or a nice idiot problem. We have been hiring people whose sole qualification is that they can fog a mirror. Okay. So, so we have a problem and we're gonna have to fix it. So it it was tough. It was really tough. I mean, it was it was September, that was probably September 25th. Um, you know, October 1st, uh, we started making changes, and I I made some changes at the exec level, and October 10th, I laid off like 35 people out of that sales organization. We had the same num, you know, the same bookings number the next month that we had the month prior with 35 less people. Uh, and you know, we continued our meteoric growth, but at a much better efficiency. And um, you know, so what did I do? I learned that lesson the hard way. We created, I sat down with that chief of staff and we created the nine values team. We went through and handpicked 15 people across our company that were the keepers of the flame, of the culture flame. And what we did is we split them functionally. So I had five of them that were salespeople, five of them that were support people, five of them were that were software engineers. And the rule was um, you could not do a nine values interview with somebody in the same function that was being hired. Because, see, I didn't want an engineer on that team to be blinded by your brilliance. Yeah, I wanted them to go, I have no idea if this person is a good salesperson or a good support person, but they're not working in this organization over my dead body. And guess what? I stopped getting these offer letters, just like how I never got bad veto interviews because nobody had the gall to put, you know, dude, you're our CEO in a video veto interview with me, right? I stopped getting these kinds of offer letter requests because they couldn't pass the nine values interview, and I would have it right there in the email. And I I think I only had two people that ever put in an offer letter request with a negative nine values interview after that. It worked.

SPEAKER_02

That's some awesome stuff. Talk to me about uh I have a lot of follow-up questions, but executive level team management. Yeah, growing

Building A Values Based Hiring System

SPEAKER_02

during growth when you're just busy. Yeah. So as the CEO, founder. You you know where you're going and you need to build this team around you. Um advice for me or others that because sometimes you're going so fast that hiring and taking the time to get the right person is just painful because you don't have time for it. But you it it's the most critical thing.

SPEAKER_03

It is and cultivating those people.

SPEAKER_02

And cultivating those people. I mean I mean what advice would you give? Because because it you know, I you know, I sat with Ryan in my office today, and I said, we gotta that's something we gotta figure out, but it's finding the time to figure it out, yeah, the energy to put into it. Yeah, we know it's critical, and then where do you find them? How do you cultivate them?

SPEAKER_01

Yeah. I mean, the the first thing I would say is um you know, it it's something that I constantly had to remind myself that that that the the the highest leverage thing I could do was to allocate time to that because it doesn't matter how successful you are, there's always that next client that wants to talk to you. There's always a current problem or a current opportunity or a product thing that you could work on or this that you know, there's a million great things you can do.

SPEAKER_02

You can lie to yourself that hey, I I I can't right now, right? I can't right now. When you and and there's also pain associated with those changes, big pain.

SPEAKER_01

And time allocation is strategy, and strategy should be painful, right? And so so I I sit that I I I had to push myself, and I didn't always get it perfect, but like I had to push myself that like time allocation was strategy. So therefore, if I wanted to get great executive leaders to help me, I was gonna have to invest some time. Um, so I I would literally like block out a day. I would block out a day with super painful, or I block out two halves of a day or something like that, but I would block out time and just go like that is my time that I'm going to spend on that. So that's number one. Number two, um, you then use that time in a couple of ways. One is, and and this was really hard for me because I was like, okay, great, but I don't know what a great CFO looks like. I don't know. I mean, I I I I'm a first-time CEO of a company of this size, okay. Every day I was the first time CEO is the first time I'd ever managed a company of that size, every single day of that 12 and a half years, right? Except for the two years where it was a flat, flat line. But anyway, after that. Um, so so I I one of the things that I was very fortunate uh to be able to do was to just draw on either mentors or great people I'd had the chance to meet, generous uh investors. You know, our our our our main investor at the time was a firm called FTV Capital. They were extremely good about being willing to help me set up this kind of thing. So I would just say, I would say, hey, I need connections to like three of the best CFOs that you've ever worked with, that you've ever experienced across all the different portfolio companies you've worked at. I'm not gonna try to hire them. I'm not trying to poach them. I just want 30 minutes of their time so I can download into my brain a mental model of what a great CFO is, right? But again, it's time. So I had to allocate, I first I had to block the time, which was painful. Then I had to allocate the time to learning like that. Then I could build like the learning model, you know, of like a CFO, so you know what you're looking for. And then I had to spend a lot of time thinking about how to design interviews. And and I I'll tell you, my philosophy of interviewing, I have I have um over time just had to invest a lot of time in getting good at it because I spend a minimum of two hours interviewing any candidate that I think is an important hire. And uh, if you're hiring somebody who's unimportant, why are you hiring them, right? So a minimum of two hours. My theory on that is everybody has about an hour of BS inside of them.

SPEAKER_03

So you're wearing them down.

SPEAKER_01

You have to, and and senior executive, long format podcast, maybe. Yeah, there you go. Do that, invite them for a podcast. There you go. No, but like senior executive 30 minutes in. Yeah, by the way, if they work in sales, you probably need four hours of interviewing. Um,

Executive Hiring And Interview Tactics

SPEAKER_01

but you know, because all salespeople who are bad at selling are very good at selling themselves. Um, that is just true. Um, but but like in all seriousness, like senior executives, three to four hours in all seriousness. Now, now I would do maybe two hours of interview, be able to cut some.

SPEAKER_02

I'm just laughing over here because this morning we had someone come in that wants to work with us, pitching us, you know, and it was a we carved out an hour for him. And a guy came in from out of out of state and sat down. And one of the questions I like asking very first, like I just think it's it's a polite thing to do. So tell me a little bit about yourself. Yeah. And 52 minutes later, that's the 52 minutes later. Yeah. And we had an hour. So 52 minutes later.

SPEAKER_01

You know what? I abolished that question. I did. Do you know what I say instead? Here's here's my question that I say instead. So the Wall Street Journal is writing a profile about your life and career. Give me the three-sentence introduct introduction to that article.

SPEAKER_02

I should have done that.

SPEAKER_01

That's what I say because of exactly that problem.

SPEAKER_02

I got up and left and I walked in Ryan's office, and I'm like, holy crap, what was that?

SPEAKER_03

There are people who are really good at just answering questions, like taking so much time answering questions and uh filibustering. They think they can filibuster their way into a job. And it's like if they're talking, they're controlling what it is, and so you'll ask them a question and they'll talk for so long about whatever they want. They filibuster. And then all of a sudden you realize like an hour's gone by and you've asked them two questions.

SPEAKER_01

I have, I in all seriousness, like, and I I've had to get better at this because it's really hard to grow a company without it. But like I have a game plan with a lot of questions, and I'm going to get to these.

SPEAKER_03

So you'll cut them off. I'll just cut them off.

SPEAKER_01

Sorry, I just need three sentences because I got a lot that I got to get to here, or you've got no chance.

SPEAKER_02

And I like the fact that you've got it.

SPEAKER_01

So you're like, hey, there's a lot to get through to just keep it in focus. Yeah. Yeah. I also I also really like to um I you have to ask indirect questions. And what I mean by indirect questions is what I what I mean is I'm asking them to tell me about a time that they dealt with X. Yeah. Okay. And here's the other thing I found is if you're if you're hiring for experience, um, particularly like a senior executive. So I'll say I you I never saw this until somebody told me this. And then I like I saw it with clear eyes. So you you say to somebody, tell me about a time, you know, CFO candidate, tell me about a time you had to deal with a tough board member who was really giving you a hard time about the reporting, and yet their their ask was just kind of ridiculous. Like, how do you deal with that? Okay. Um and and so uh the person will say, now you're hiring this person to be a senior executive to manage, to help you manage this kind of stuff and take heat off of you, and and like you don't have to worry about that kind of thing, right? So this person, here's what they say they go, Well, when you're dealing with a demanding board member, you really want to think about this and this and this and this. Okay, they're listing to you the table of contents of a book that they have read. Right? I said, tell me about a time that you handled this, that you dealt with this, right? So I'll just say to that person politely, oh, whoa, whoa, time out. I I I need to read that book. I know I'm very I need you to take me into the story. I want to hear names and places and the exact experience here. This all stays between us. We're not on a podcast, we're on an interview. Okay, so like this is all between us, but I want to hear like the name, the place, the story. Like they take me into the story with you, make it fun, go. And then they they you know, the ones who have not actually done it look back at you and they go, Well, I'd love to do that. So, like when you're thinking about how to handle this, you just you know, and they just go right back down the same list. So that's when you know they haven't actually had the experience of doing that, right?

SPEAKER_03

That's really good.

SPEAKER_01

That's awesome.

SPEAKER_03

We need pivot. Yeah, can I can I ask a question? Changing gears. You can ask whatever you my friend. So you built this business in California. Yeah. You had this uh really big exit, really successful exit. It was a great accomplishment of what you built. Thank you. Um, I I guess to two related questions of that time in your life. One, how did it feel when after you exited, like in the immediate aftermath? Because I think that so many founders, this is like all they think about, like, oh, I'm building this to exit, I'm building this to exit. And then they get there and it's like, oh, well, this feels different than I thought it would. So how did that feel? But then the other thing I want you to get into is what led to your decision to move here to the Treasure Valley. Sure.

SPEAKER_01

Absolutely. Well, first of all, um, yeah, I I'd honed by choice because uh my my wife has had extended family up here for years. Okay. Um, we uh we've had so many friends uh that moved up here in the past. So I think it was probably 2014 or 2015 that we said, we want to end up in Boise, we want to end up in the Treasure Valley. And um uh we uh unfortunately we did not have any money with which to buy our property then, or we would have gotten a much better deal on it. Uh, but uh such is such is life. Uh so and and you

The Exit Feeling And Moving To Idaho

SPEAKER_01

know, it just felt like it was impossible to do uh because I'm running that company, uh, we have a headquarters, we are in person. I about had about 125 of our 200 employees coming to work every day in that building. Uh so then COVID hit, and it was very interesting because um we lived in the Idaho part of California. Okay. So to put it just bluntly, like COVID was not uh it you didn't get the classical California COVID experience where we lived in California. Okay. Um we had a little bit more of the Idaho uh COVID experience, a little bit more common sense uh in that part of the of the state per se. Um but all that to say, um it so it didn't kind of drive us out, but it did enable it because um all of a sudden we went to um, you know, nobody like I don't think that office has gone gotten over six people since then. Oh, so they went all we went all remote, and then you couldn't get a California software engineer back into the office to save your life. Like I called one of them who'd been with me for eight years uh in November of 2020, and you know, and I said, Dan, I think I think we're gonna I think we're gonna bring everybody back in. He goes, Don't do it. I'm like, tell me why. You live 10 minutes away from the office. Like it, you know, collaboration is hard. I by the way, I had no productivity problems with people. People worked really hard. Okay. It was all about collaboration and it was all about innovation. It was all about being able to iron sharpen iron and and being able to spark off of each other with ideas. So uh, but I just said to him, I said, tell me why. You're 10 minutes from the office. He goes, look, he goes, every myself and every person on this team that I lead for you has gotten an offer over the last couple of months from Facebook and from Airbnb for $40,000 more in base salary than you pay us. Not a single one of us have taken it. We we we don't want to be a cog in their machine. We love our mission, we love our culture, we love our values, we love what we're about. Force us to start putting pants on again in the morning, and we might have to take the money.

SPEAKER_03

And I was like, That's a social media clip.

SPEAKER_01

It doesn't match. I don't I don't know what to say to that, you know? So so I just had to accept that. Like that was really hard. It was really hard for me. And um, but I just said, okay, well, guess what? If everybody else can live where they want to live, we can live where we want to live too. So we were on track to, you know, to sell the business in 2021, sold the private equity, told every buyer during that process, hey, um, I I, you know, I'm a to the extent that you want me to continue to run the company for you after the sale, I will be doing so from uh my new home in Idaho because we're gonna move up there, you know, uh at some point soon. And all of them were like, great, no problem, you know, no big deal. And so um did a great deal with HG Capital um out of London and they acquired the business and uh I ran it for them for another two years uh and I'm still on the board today. So, you know, to go back to your other question, I I I think, you know, it's it's super interesting. First of all, I would just say, um, man, if you're doing this for the love of the exit, I'm not sure that it's gonna work out for you. I'll just be really amazed. You know, um, I think you got to be doing it for the love of the craft. And people have said multiple times, why in the world would you go back to ground zero and do this again from scratch? Yeah. Uh you don't have all the trappings and all the people and all the all the stuff, you know. And I and I say, well, I love building impactful things with smart people. You know, that that's that's the craft that God has given me a few talents uh around and that and that I I've had this this love of doing. And so um, you know, so that that's that's what I feel like he's got me on earth to do. And so that's what I'm gonna do. Um, you know, so so first of all, I think you got to do it for the love of the craft. Um, second of all, I will say, um, you know, for sure, I mean, we were up to our eyeballs in debt when we started that business. We were paycheck to paycheck. And um, you know, it wasn't quite the exit. It was a little bit before the exit. It was 2016, maybe four and a half years before the exit, that we did um a deal with uh our our first institutional capital. That was the FTV capital firm that I that I mentioned before. And they had a minimum investment size that was more than the cash that I wanted to put on the balance sheet. And we'd built a pretty decent business at that point. Uh, and so I just sat down with them. I said, look, here's what I want to do. I want to put this much on the balance sheet and the rest of that, I want to go out and um and and let some of my angel investors take some money off the table. And I would like, I don't want to get rich off of this, but like I would like to just get out of debt. You know, I've been up to my eyeballs in debt. So I literally paid off everything but my mortgage and just kept paying my mortgage. And um, you know, so I wouldn't say that we were, you know, floating or wealthy at that point in time, but um, but but we at least could breathe, you know, and it was it was a really that was a really good feeling. That was a that was even a bigger feeling than I would even argue the exit. Okay, and the exit was great. The best moment of the exit, I have to tell you, was bringing some early employees into my office the night before it was announced and telling them that they were millionaires. That I could do that all day. So awesome. Oh my gosh. Like to to get to see the impact that we got to make on families. Um, you know, we were seeing impact on families just while we were operating as a company because we had created a bunch of really great high-paying jobs. You know, at our high point, we were the largest employer in little old Auburn, California. You couldn't go into a restaurant in town without seeing our logo dangling off of a badge, you know, on somebody's belt. And um it was, I would get our pens with the bill uh at restaurants, which was hilarious,

Why Contio And Relationship First AI

SPEAKER_01

um, you know, all the time. So, so that it was incredible to see the impact. Houses were getting bought, and kids were going to school, and you know, and and people were living lives because of the jobs that that we had collectively been able to create together. Um, and then to see the massive, you know, impact that that made on some of those early employees is just something else. So yeah.

SPEAKER_02

That is awesome.

SPEAKER_01

Yeah.

SPEAKER_02

So then you know, there's so many lessons from what you're saying are so obvious that we don't have to restate them, but the journey, right? Yeah, the passion, why you do it, your why did you change? Yeah. So it makes sense that now you start the new thing. Yeah. So talk about that because I should start that.

SPEAKER_01

Yeah. And uh it's it's a blast. We're having a lot of fun. Um, it is a very interesting time to be a software company right now because AI makes software abundant and makes attention and distribution scarce. And so you have to think very differently about it. Um, I am very used to being called Boy Wonder. I'm not as used to being called old dog who has to learn new tricks, but I'm just embracing my new role, you know. Um, and so so we're figuring it out. Uh and grateful to have Capital 11 along uh for the for the journey as as uh as really our our only institutional capital that uh that is in Contio right now, but we're but we're still very early. We're we're we're figuring things out. You know, the passion for this is I I I was sitting there um, you know, I had that amazing journey with Riskalize, um, passed the baton to my successor, um, and you know, kind of took 2024 off to just decompress and and and and just kind of look out at the world. I had three kids in high school that year, a freshman, a junior, and a senior. And I was like, this is just a good year. I promised my wife I would take some time off at whatever that finish line looked like. And so, so it kind of took that year off. And I was looking out of the world and I am watching these big AI foundation lab CEOs come out and say, Oh, this artificial intelligence technology is just incredible. It's it's like a nuclear bomb. It's going to eliminate jobs, it's gonna like put us all out of work, we're all gonna be, and I'm I'm you know, this is the rhetoric that we're hearing from a lot of these AI Foundation Lab CEOs. And I'm looking at this technology and going, look, I I've just come off of a 12 and a half year journey of serving professionals in relationship-driven businesses where they are making this incredible impact on other human beings every day. And you have not really, I mean, like the the I I to digress for a second, like we're serving financial advisors who are literally multiplying the impact that we were trying to make about empowering the world to invest fearlessly, because every financial advisor we were serving had a hundred families that they were shepherding from, you know, to success in their financial lives, whether that meant that their kids got to go to college, whether that meant that they got to retire with dignity, whether that meant that they got to make world-impacting nonprofit gifts, you know, with what they did. I mean, this is this is just good old American capitalism at work helping people succeed and financial advisors helping them get across to that other side. And so, so I'm sitting there going, I look at at AI and I'm like, yeah, we we need to build this technology in a way that amplifies the impact on human relationships. We need to build AI that is going to uh, you know, take take the conversations that humans are happening, or are having and just flow that right into the work because if we can take all of this rote work off of these professionals, it just frees them up with more time to reinvest back into those human relationships and to drive the value of those. So to me, that's what's really exciting. So we we we built Contio, uh, we like to say we turn what gets said into what gets done. Uh, it starts at a very basic level. I use Contio in every meeting that I'm in. I'll sit down for a meeting. Uh, I either pop open the mobile app on my phone or I've got my computer with me and I hit capture. And we now have this compounding workspace intelligence of all the things that we're talking about and figuring out going into our secure workspace. And it, you know, it sits in the background on your Mac or or

From Meeting Capture To Agentic Workflows

SPEAKER_01

on your Windows computer. Uh so no annoying bot joining your video calls. It works for in-person meetings. It's not an AI note taker that most people are for kind of hate. Yeah, we got to go beyond the AI note taker and just go, how do we get conversation data to flow into the work that we do? And then, and then the next step of the journey that we've uh been been building, which we're we're very excited about, we've just been starting to roll out the first pieces of it, but it's a it's a full-blown narrative workflow platform. So any kind of complex workflow that a business runs that starts with a meeting or a conversation with human beings, uh, you can you can literally have that flow in as data to an agentic process that is going to be able to push it all the way through. So for you know, can't quite announce it yet, but like we have the first target vertical with a bunch of committed design partners, all right here in Boise, Idaho, uh, where we are building a full-blown end-to-end AI agent that starts with a meeting with human beings, flows all of that data in. The agent helps take all the rote work off of those people, and they can turn around and reinvest all that work back into the human relationship. Love it.

SPEAKER_02

Incredible. Where do I sign up?

SPEAKER_01

Well, we'll get you started right away, Contio.ai. Because seriously, while we are really focused on, I mean, like we're what's gonna scale revenue for us is the agentic workflow platform that we're just talking about. Um, but uh at a pretty low cost, you can you can go, it's basically it's like 29 bucks a month, right? You can go to contio.ai and you can use this. I love this thing of my life, my my life. My wife uses it. She's in a master's degree program for uh becoming a counselor with an emphasis in adoption trauma. That's that's her passion. Uh and and she uses it in all of her classes and all of her interactions with people, and like it like it like flows stuff right into the work. Um, I use it in every meeting I'm in. We talk about, you know, we'll have like 15 different meetings over the course of three weeks to debate this new software feature that we're gonna build, right? And we're arguing about it, we're going back and forth. And at the end of all of that debate, I can literally go in and say, hey, give me, give me the the product brief to describe exactly the feature that we're gonna build. And it synthesizes all of that conversation and all of the different arguments that we've had and what decisions we made, and spits out a perfect three-page product brief that we can drop right into the process for an agent to go off and start coding uh for one of our engineers to shepherd to completion. It's it's it's incredible what happens when you turn what gets said into what gets done. Amazing.

SPEAKER_03

Yeah. It's incredible. I think, you know, as as Tommy gave me this opportunity to co-host some some episodes with them, and and what I was passionate about was just like, let's showcase people who are building great companies, creating jobs, moving here, live here, whatever. And and what we've seen with Jeremiah, with Eric, with Aaron, it's just such an example of the quality of people that are here. In that are building. And I'll share, you know, Aaron did a uh a retreat that he put together. People flew in from around the country. He was kind enough to invite me. And I walked in and quickly realized I was like the least accomplished person in the room. And there's true. There's Fortune 100 CEOs there. And I was talking to one of them and I was like, this is incredible that Aaron got these people to all fly into Idaho for a two-day retreat at his home. And he looked at me and he said, Well, if Aaron invites you to something, you come. And I mean, we again, people fly in from New York to just come to his house for this two-day, you know, uh retreat. And so it really speaks to the the quality of him. We've seen that today in what he said. You can tell what kind of leader he is and what kind of builder he is. But I just I hope people take away from this. This is what's happening in Idaho. This is the quality of people. And and

Building In Boise And The Future Of Work

SPEAKER_03

I I before we one thing before we finish, I want you to just share a little bit about you've you've hired a full engineering team. You're you're you're building this in Eagle, Idaho, in office, in person, with a bunch of people. And so maybe you just share a little bit about that.

SPEAKER_01

Absolutely. I mean, we we I listen, I just pinch myself that I get the chance to be in Idaho and by choice. Okay. Um we live in the greatest state. And I know we're not allowed to say that too loudly because I think the Constitution says we're supposed to tell everybody we're full or something like that. But um, but no, I I we we just live in the greatest state. We we have we have so many advantages. And um, and I just feel really, really grateful. I I I look back at this valley and I look at the foundation that has been laid by, you know, you you would you would point to Hewlett-Packard, you would point to Micron, you would point to uh, I mean, you'd you'd then have to point to even Simplot, even though it's not a technology company, just helping to plant some of those seeds, right? And and and help. And then you think about, you know, uh companies like Clearwater and companies like T-Sheets and companies like uh, you know, Count and so many great companies that have created this technology ecosystem here. So for what it's worth, I had a couple of people who said to me, you know, don't kid yourself. You're you're you're you're you're building this in Boise, Idaho, because um, you know, that's just convenient for you. And I said, no, no, no, you you you don't understand. I I used to live in a little town of 30,000 people, like very far away from Silicon Valley and very far away from that. I had to scratch and claw to build a technology company without a talent base. This is a plethora of riches in terms of the of the technology ecosystem that we have here. And and we have found incredibly top-shelf talent here um, you know, uh across AI, across architecture, across, across all the different aspects of technology. Um, and so I just feel incredibly grateful in that regard. I feel like we've got an incredible team. Um, and we're we're gonna continue to grow it right here from Idaho for as as long as we can. And I I don't know how many employees the company grows to. I don't know exactly what that journey looks like and what it's gonna scale to in that regard. Uh, you've been able to do more with uh I think I think the future is probably uh companies, uh particularly in technology that are are not that have pretty high revenue per employee and are not um as as as large scaled as I was, you know, with with riskalize. I think, in other words, riskalize could probably, I could probably have run that at 100 people instead of 200 people today. But I'll tell you what, those are going to be even more highly paid people, right? Those are gonna be higher quality jobs. I I I look at the future, I feel some people hear that and they go, oh, so a lot of people are not gonna have work. No, no, no, no, no, no, no. I uh a lot of people, we're we're headed for a time of like some real abundance here. You only had to go back to you know the early 1900s, and people had to work about 60 hours a week just to get the calories on the table to survive. That's down to 31 hours now. And I'll be clear, I don't work 31 hours. I hope not. Yeah, no, no, I invest. I don't work 31 hours. But I'm talking about like what is required to survive. Okay, what is required just to put the calories on the table to survive? Okay. And we all know that our grandparents, right, uh, who, you know, you think of them in in in many of them farmers, okay? They had to work an insane number of hours just to put the calories on the table to survive. That number is down to 31 hours today. I think that number is down to 20 hours in a matter of five to 10 years, somewhere in that range. And so what that means is we're we're we're gonna have a lot of options. People are gonna have a lot of options and a lot of choices. And I think that we should be excited about the fact that there are options and choices and not buy into the rhetoric about, oh, that's gonna create more inequality. I think it's gonna create a wider range of choices. Like I'll be clear, Elon Musk is both smarter than me and a lot wealthier than I am. And that's okay because guess what? I don't want to work 120 hours a week. I don't want to work 31 hours a week, but I don't want to work 120 hours a week and sleep on factory floors. So God bless him. That's his set of

Where To Follow Aaron And Closing

SPEAKER_01

choices. And let him do that. And I'm gonna work my 60 and um I'm gonna I'm gonna enjoy building impactful things with smart people.

SPEAKER_02

Uh, for our listeners that want to follow you or learn more. This has been fast. I could sit and listen to you. Thank you. Are you gonna write a book?

SPEAKER_01

I've thought about it, but I haven't done it yet. You should write a book. Thank you.

SPEAKER_02

There's a lot of there's a lot of wisdom and pearls here. Thank you. Um, how do we follow you?

SPEAKER_01

Um Yeah, I I I'm on um, let's see, I'm on I'm on X at uh Aaron Klein, A-A-R-O-N-K-L-E-I-N. I'm on LinkedIn, love connecting with people, and then you know the company is Contio, Contio C O N T I O dot AI. And uh love connecting with people, especially here in uh the greatest state in the union. Fantastic. Amazing, thank you so much. Thanks. Gotta do it again. Thanks, everybody.