Aaron Klein describes Riskalyze as a twelve and a half year overnight success. That framing, which he credits to his wife, is the honest version of a story that usually gets told as a straight line: category-defining fintech company, 42 consecutive quarters of growth, 200 employees, 35,000 users, acquisition by private equity in 2021.

The actual path involved a failed payments company for political candidates, a “successful failure” of a consumer product that made the New York Times but couldn’t get a single broker to license it, and a moment with three months of runway left in the bank when the team decided that if they were going down, they were going down swinging.

On the latest Ever Onward Podcast, Klein joined host Tommy Ahlquist and co-host Travis Hawkes for a conversation that moved from those early scrapes through the hard-won systems he built to protect company culture, and into why he believes the prevailing narrative about artificial intelligence has it fundamentally backwards.

What an 18 Percent Margin Business Teaches You

Klein started working for his father at twelve, in a wholesale distribution business for automatic gates and security equipment. Eighteen percent gross margins. Commoditized product. No capital for inventory. The only real competitive advantages available were the quality of the customer relationships and sheer grit.

He took three lessons from those years. Relationships are everything in business. Entrepreneurship requires more persistence than most people understand going in. And he wanted to work in a much higher margin business when he grew up.

At twenty-two, with no investment bankers and no business brokers involved, he went on the road to the five obvious buyers and helped his father sell the company.

The Budweiser Moment

The most instructive story in the entire conversation is about the day Klein realized his company culture had slipped.

Early on, he had instituted what he called the ten-minute veto interview. Every candidate, regardless of role or hiring manager, needed a short video call with him before an offer letter could go out. Around 2016, during a period of aggressive sales hiring, the complaints mounted: Aaron, you’re the bottleneck, we’re losing great candidates waiting two weeks for your calendar.

He acquiesced and abolished the process. That, he says now, was the mistake. Not abolishing it, but abolishing it without replacing it.

Roughly eighteen months later, he walked into the company’s first all-hands retreat at a Hilton Garden Inn in Emeryville, still carrying his bags from a flight. A man he had never seen before, in sagging jeans with an eighteen-pack of Budweiser on his shoulder, looked at him and said: “Dude, you’re our CEO.”

Klein’s shorthand with his chief of staff had always been “talented jerk or nice idiot?” when someone needed to be let go. This time the answer was neither. “We have been hiring people whose sole qualification is that they can fog a mirror.”

Within about two weeks he made changes at the executive level and laid off 35 people from the sales organization. The following month the company booked the same revenue number it had with 35 more people on staff.

The Nine Values System

What Klein built to replace the veto interview is worth understanding in detail, because it solved a scaling problem without recreating the bottleneck.

He and his chief of staff hand-selected fifteen people across the company who were, in his words, keepers of the culture flame. Five from sales, five from support, five from engineering. Every candidate had to pass a nine values interview with someone from that group.

The critical rule: you could not conduct a values interview for a candidate in your own function.

The reasoning is sharp. Klein didn’t want an engineer evaluating an engineering candidate and getting blinded by technical brilliance. He wanted someone who would say, “I have no idea if this person is good at their job, but they’re not working in this organization over my dead body.”

It worked almost immediately. The bad offer requests stopped arriving, in the same way nobody had ever tried to sneak a “dude, you’re our CEO” candidate past him in a video interview. Over the remaining years, only two offer requests ever came through with a negative values interview attached.

He also keeps a list of four people he will not hire under any circumstances: mercenaries who don’t believe in the mission, jerks who tear down others, narcissists who think it’s all about them, and people with a victim mentality. He has hired all four types before. Once, he notes, all four in the same executive.

Time Allocation Is Strategy

Asked how a founder finds time for senior hiring during a period of intense growth, Klein was direct: there is always a client who wants to talk, always a current problem, always a product decision. The work never stops presenting itself as more urgent than hiring.

His answer is a phrase worth borrowing. Time allocation is strategy, and strategy should be painful. He would block a full day, or two half days, purely for executive search work.

He also had to solve a more basic problem: as a first-time CEO, he didn’t actually know what a great CFO looked like. So he asked his investors to connect him with three of the best CFOs across their entire portfolio history. Not to recruit them. Just to spend thirty minutes each downloading a mental model of what excellence in that role actually looks like.

On the interviews themselves, his rules are specific:

Minimum two hours per important candidate. Three to four for senior executives. His theory is that everyone has roughly an hour of BS in them, and you need to get past it.

Ask indirect questions. Not “how would you handle a difficult board member,” but “tell me about a time you handled a difficult board member.” When candidates respond to the second question with a framework instead of a story, that tells you they’ve read the book but never lived it. Klein’s move in that moment is to politely interrupt: give me names, places, the actual story. The ones who haven’t done it will slide right back into the framework.

Replace “tell me about yourself.” Klein abolished the question entirely after too many candidates filibustered through most of an interview slot. His replacement: “The Wall Street Journal is writing a profile about your life and career. Give me the three-sentence introduction to that article.”

Why He Started Over

Hawkes asked a question most founders never get asked directly: how did the exit actually feel?

Klein’s answer was that the best moment wasn’t the close. It was the night before the announcement, bringing early employees into his office one at a time and telling them they were millionaires. At its peak the company was the largest employer in Auburn, California, a town where you couldn’t walk into a restaurant without seeing a Riskalyze badge on someone’s belt.

He was also candid that the more meaningful financial moment came years before the exit, in 2016, when a growth investment let him pay off everything except his mortgage after years of being deep in debt.

His advice to founders is unambiguous: “If you’re doing this for the love of the exit, I’m not sure it’s going to work out for you. You’ve got to be doing it for the love of the craft.”

Which is why, rather than retiring, he started Contio and went back to zero. “I love building impactful things with smart people. That’s the craft God has given me a few talents around.”

AI That Amplifies Rather Than Replaces

Klein spent 2024 decompressing and watching the AI conversation unfold. What struck him was the rhetoric coming from foundation lab leaders: this technology is like a nuclear bomb, it will eliminate jobs, it will put us all out of work.

Having just spent twelve years serving financial advisors, professionals whose entire value lies in relationships with the families they shepherd through college savings, retirement, and charitable giving, he found that framing both wrong and uninspiring.

The alternative thesis behind Contio is that AI should take rote work off relationship-driven professionals so they can reinvest that time into the relationships themselves. The product captures conversations, from video calls and in-person meetings alike, without a bot joining the call, then flows that conversation data directly into the work that follows.

The example he gave is concrete. Fifteen meetings across three weeks debating a new software feature, with arguments going back and forth. At the end, he can ask the system to synthesize all of it into a three-page product brief capturing what was decided and why, ready to hand to an engineer. “It’s incredible what happens when you turn what gets said into what gets done.”

The larger build is an agentic workflow platform for complex business processes that begin with a human conversation. The first vertical, with committed design partners, is being built entirely in Boise.

Building in Idaho by Choice

Klein and his wife decided around 2014 that they wanted to end up in the Treasure Valley. Running an in-person company with 125 people coming into a California office made that impossible until COVID changed the equation. When one of his longest-tenured engineers told him that everyone on the team had received offers from Facebook and Airbnb for $40,000 more in base salary and turned them down, but that forcing them back into an office might change that math, Klein accepted the new reality. If everyone else could live where they wanted, so could he.

He pushed back firmly on the suggestion that he’s building in Boise merely because it’s convenient. Having previously built a technology company in a town of 30,000 with no local talent base, he described Idaho’s current technology ecosystem as a plethora of riches, built on foundations laid by Hewlett-Packard, Micron, Simplot, and more recently companies like Clearwater and TSheets. He has hired top-shelf engineering and AI talent locally and intends to keep building here.

The Optimistic Case for the Future of Work

Klein closed with a framing that cuts against most AI anxiety.

In the early 1900s, a person had to work roughly 60 hours a week just to put enough calories on the table to survive. Today that number is around 31 hours. He believes it drops to about 20 within five to ten years.

What that produces, in his view, isn’t mass unemployment. It’s an expanding range of choices about how people spend their lives. He expects fewer employees at high-growth technology companies but significantly better-paid ones, and thinks the future belongs to businesses with high revenue per employee rather than large headcounts.

“I don’t want to work 120 hours a week and sleep on factory floors,” he said, contrasting his own choices with Elon Musk’s. “God bless him. That’s his set of choices. I’m going to work my 60 and enjoy building impactful things with smart people.”

Learn more about Contio at contio.ai. Aaron Klein can be found on LinkedIn and on X at @AaronKlein.