In second grade, Mason Swofford won a math contest and took home a one-cent bubblegum machine. Most kids would have eaten the gum. Mason started selling it on the playground at a 2,400% markup. Within weeks, he had traded three pieces of bubblegum for a pair of pink diamond earrings from a classmate whose parents owned every Domino’s franchise in Indiana. He was seven years old.

Two decades later, that same instinct for spotting value where others see noise led Mason to build Tenzo AI, a recruiting technology company that uses AI agents to transform how large employers find and hire talent. From bubblegum arbitrage to billion-dollar hiring infrastructure, Mason points to a single trait that has driven his success so far: he cannot move past something he does not fully understand.

From Indiana to Stanford, by Way of Stubbornness

Mason grew up in Indiana, the youngest of three siblings. His father jokes that raising Mason was “payback” for his own childhood habit of asking a million questions. On 30-to-45-minute drives to school, Mason’s parents would quiz his older siblings on math. Mason just listened. By the end of three years, he had caught up to his eldest brother’s math level, simply by asking “how do you do that?” over and over.

His relentless curiosity carried Mason to the top of his high school class of 712 students. His GPA gap over the second-place student was the same as the gap between second place and 50th. He earned more fives on AP exams than anyone else in the state of Indiana. No one from his school had been admitted to Stanford in 17 years.

“My guidance counselor, everyone was like, good luck,” Mason recalled during a recent conversation on the Founder Uncovered podcast with host Kevin Jurovich.

He got in. He found out in a barber’s chair, phone buzzing with texts from friends in a group chat who had all been rejected. He checked the email, saw the acceptance, and opened a bottle of champagne with his parents opened that night.

Meet Tenzo: Agents That Recruit

At Stanford, Mason studied computer science and dove headfirst into artificial intelligence research, driven by his aptitude for statistics. He was working in AI labs as early as 2016, when the field was still called machine learning by most people outside academia. He watched every lab on campus run their work on NVIDIA GPUs, put all of his money into NVIDIA stock as a college student, and has watched that investment grow roughly 50 to 60 times since.

After graduating, Mason started a PhD at the University of Texas at Austin, then dropped out when he realized he was spending years on a path that kept moving further from what he actually wanted: to build a company. He explored for about a year, building coding agents and legal agents in early 2023, before most people had heard of either concept. One of those coding agents had more users than Cursor at the time. Mason walked away from the project, convinced that Microsoft and GitHub Copilot would steamroll any competitor.

“That’s a mistake that was costly for me. Kudos to the Cursor founders. They knew that if they built a better product, they would eventually win out.”

That lesson reshaped how he approached his next venture. Mason and his co-founder, JC, launched what is now Tenzo AI (originally called Salve) with a focus on recruiting. Tenzo builds two types of AI tools for hiring teams: autopilots, which are true agents that take actions on behalf of recruiters and hiring managers, and copilots, which assist humans in real time by pulling up context, searching information, and surfacing relevant data during conversations.

What sets Tenzo apart in a market that now has 40 to 50 competitors is its emphasis on three things most rivals treat as afterthoughts: compliance, candidate experience, and customization.

“A company is nothing more than a collection of people and contracts, and frankly, people built the contracts, so it’s really just a collection of people.”

Mason brings his Stanford research on algorithmic bias directly into the product. Tenzo’s agents operate within strict regulatory guardrails, ensuring companies avoid disparate impact against protected classes. He pointed to lawsuits against Amazon and Workday as cautionary examples of what happens when hiring technology is built without compliance at its core.

On the candidate side, Mason described a common frustration: applying to 1,000 jobs, hearing back from five, and receiving a rejection email a year later for a role long forgotten. Tenzo’s Candidate Concierge agent lets applicants have open-ended conversations with an AI that searches every available role at an organization, matches candidates to the right positions, answers their questions, and guides them through the application process.

The company primarily serves larger employers. Its largest client has more than 250,000 employees. The sweet spot starts at companies hiring at least 50 people per year.

The $4 Million Week

Mason and JC raised a $4 million seed round in just over a week, with their pick of term sheets. Mason is candid about why it came easy: both co-founders came from Stanford, and they had built credibility over years of working at strong companies where leaders could vouch for them.

The key, Mason said, was not cold outreach to investors. It was founder introductions. Friends from Stanford who had started their own successful companies, and founders at places where Mason had previously worked, made direct introductions to their VCs. One friend had previously asked Mason to be his co-founder and CTO. That endorsement carried real weight.

According to Mason, the best way to get a VC meeting isn't cold outreach. It's a founder they already back picking up the phone for you. Someone who can say, "Mason and JC are the smartest people I know. I'm putting money in."

The duo ultimately chose Abstract Ventures as their lead investor. Mason also offered practical advice for founders who lack those networks: go through an accelerator like Y Combinator, and above all, build a track record at every job that makes people say “I wish I would have met them five years earlier” during backchannel references.

Stop Planning, Start Doing

Mason’s biggest advice for aspiring founders is blunt: stop planning and start doing.

“Don’t prep. Don’t set up your legal entity. Don’t do any of those things. Get in front of customers. Don’t even build. Get in front of customers.”

He believes the recruiter role itself is undergoing a fundamental shift. Roughly 60 to 70 percent of people who call themselves recruiters today are really screeners, he argued, and that job is being replaced by AI that can screen more effectively, more consistently, and at lower cost. The recruiters who thrive will be the ones who sell candidates on why their company is the best place to work, advise hiring managers, and orchestrate the agents doing the heavy lifting.

When asked about his biggest inspiration, Mason did not name a tech icon, but mentioned his parents instead.

“I would not be where I am today without my mom having dedicated so much of her life to raising us and my dad putting up with all of our crazy questions and pushing us. There’s nothing that I look back at and I go, they did it wrong.”

His favorite book is “The Challenger Sale,” which he recommends to anyone, not just people in sales roles. “Every job, frankly, is sales,” he said. “Especially to move up.”

This season is supported by Perkins Coie. Perkins Coie is a leading international law firm known for providing high-value, strategic solutions. The Emerging Companies and Venture Capital team counsels startups and the investors who back them, supporting clients from formation to exit. In the past three years, clients have raised more than $23 billion in private markets between the pre-seed and growth stages. Perkins Coie combines tailored counsel with sector experience, so when it’s time to accelerate, whether for the next financing round, a strategic deal, or going public, your team is ready. To learn more, visit perkinscoie.com

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Katrin Kaurov and her co-founder Aleksandra Medina were taking a long walk through New York, trying to decide what kind of company to build. Their first idea was to solve climate change.

“We were like, you know what? We’re just not smart enough for that.” So they kept walking. Then something else clicked.

Money had always been the thing no one helped them with. While neither of them knew the word “fintech” yet, they went back to the small apartment they shared in Chinatown and made a pros and cons list. The cons column filled up fast: no skills, no connections, no money, no green card. The pros column had two entries. They were young. And they were (their words) “kind of tall”.

The two women looked at the lopsided list and said they were going to do it anyway. Then they named their company F*cking Rich.

“There was just a lot of delusion back then in us getting started and being committed to this.”

Katrin still has a screenshot of that pro/con list on her phone. It’s the clearest possible picture of how Frich began, and in a way, it explains everything about how it has grown. Katrin has never makes major decisions for Frich by polling a roomful of experts. She makes them by watching what her users actually do, and then refusing to be talked out of what she sees.

The Problem She Lived First

Katrin Kaurov is the co-founder and CEO of Frich, a social finance platform with 1.6 million users built around the idea that people make better money decisions when they can see what people like them are actually doing.

She is originally from a small town in Estonia, population around 100,000. At 14, she left home to start working, traveling to more than 20 countries over the next nine years. She earned and invested her own money from the beginning with no one guiding her.

Katrin’s experience being financially independent as a teenager with no safety net is the direct origin of what Frich solves. She did not build her company just because she saw a market opportunity. She built it because she had lived the problem.

She mentions the similarities between her early work as a model booking clients abroad and pitching to investors years later. “In both cases, you’re kind of selling yourself.” She found the VC world surprisingly gentle by comparison. “I was shocked that everyone was so nice.”

Pitching her company, though, required a different kind of work. Coming from Europe, where confidently talking about yourself is considered bragging, she had to learn a different register entirely. Ryan Falvey, a partner at Restive Ventures and her lead investor, helped her put her story together in a way that was coherent and memorable. Once the narrative was sharp, everything else followed. Investors responded. Media picked up the story. Users found her.

Making Money Social

Frich exists because traditional financial institutions missed two things about Gen Z. First, money decisions are social. People do not change their financial behavior because of a tool or a calculator. They change it because someone they respect made a similar move first. Second, money sits behind every major life decision, not just savings accounts. Breakups, career changes, moving cities, getting a pet. Frich starts with the life decision, not the financial product.

The platform’s first version tested this the hard way. The original product challenged users to hold their friends accountable for better money habits. “Fair to say people hate their friends around their money,” Katrin said. The real insight: people want context from strangers in similar situations, not accountability from people they know.

“If you’re 25 living in New York making 120k a year, you want to know what people exactly like you are doing with money.”

That pivot shaped everything. Users are now three to four times more likely to convert to a financial product when a peer, specifically someone slightly ahead of them in a similar career, suggests it. Close enough to feel reachable. That is the mechanism.

“Community is not just a fluffy word around finance. Community and peers around you are what drives you to make certain financial decisions.”

The platform’s AI-powered feature, Frich Scoop, lets users take a screenshot of anyone’s LinkedIn or Instagram and receive an estimated income and lifestyle breakdown, covering spending patterns, brands worn, restaurants frequented, and career trajectory. When it launched, over 90% of users scooped themselves first. Nobody anticipated that. People were more curious about how they were being perceived than how anyone else was living.

Frich’s core user skews female, something Katrin attributes directly to her own team’s makeup and the creators they chose to work with early on. “We accidentally built for that community,” she said. That user is typically 23 or 24, one or two years out of school, often already feeling behind.

“They’re seeing TikTokers already retired by the age of 19. By default, even though you went to the best school and have a six-figure job, you already feel like you’re behind.”

One of the sharpest early product lessons came from the onboarding flow. When users were asked to pick a financial goal, most of them froze. They did not know what their goals were. “It’s not a math problem. Anyone can go and figure it out, but people don’t do it because they’re afraid of money.” The app now builds the framework before it asks for the commitment.

To illustrate where she wants to take this, Katrin points to a recent unconventional partnership. Frich collaborated with a prominent New York prima ballerina to reach a community that had essentially no relationship with financial services. A dancer’s career is short. “You’ve got to make very smart financial decisions to protect your future.” The campaign activated millions of dancers and connected them with fertility insurance, directly relevant to their situation. It became one of Frich’s most successful campaigns.

“Fintech is not just for people who work in finance. Fintech is for everyone, and these people are so underserved.”

Building the Expert From Scratch

When Katrin started Frich, she had no fintech credentials, no industry connections, and no roadmap. She and Aleksandra googled how to build an app with no money or skills. There was no ChatGPT yet.

But Katrin had two things: proximity to the problem, and the discipline to document everything she was learning from her users.

“I realized that there’s not going to be a moment when someone is going to label me as an expert if I don’t do it myself first.”

She began posting data and user insights on LinkedIn, launched a newsletter, and positioned herself as a Gen Z money expert. She kept showing up in that lane consistently until the label was accepted as fact.

“If you just build in silence, no one is going to know that you have actually accumulated all this industry knowledge. Building in public, especially in today’s era, is really important.”

The same thinking shaped how she approached her personal story. “You’ve got to spend a lot of time to get to that perfect personal story. But once you’re there, you can’t really deviate. You’ve got to stick to the same story over and over again.” The goal is not self-promotion but clarity, a sharp, repeatable angle that travels.

“Investors are kind of looking for misfits and weirdos. It’s actually easier to stand out if you’re the weird one. At least it’s going to get you the first meeting.”

Getting in the room with investors was one problem. Holding her ground once inside was another. An early advisor told her Frich needed a real CEO, someone with credentials and experience. She was offended. VCs later pushed her to pivot into NFTs and Metaverse events. “I remember thinking, are these people stupid?” She had not yet learned that pushing back was an option. She was doing this every single day, and she understood the Gen Z relationship with money better than any generalist investor operating from the outside.

“The moment I learned to push back, that’s also when raising became much easier for me.”

109 Conversations

Katrin had heard the statistic before she lived it: Go through a hundred VC conversations to get one check. When she hit number 102, she tried to stay optimistic. “I was like, we’re across the mark, so it means we must be close.” The round closed at conversation 109.

One of those discussions started with the investor hanging up the call because he said her idea was stupid. She could not let it go. So she reached back out and got another call. He passed again. She applied to an accelerator his fund opened. No response. She emailed asking if they had received her application. No response. She emailed again. Her final message was black and white: “Are we doing this or what?” The partner replied and wired the money.

“I still today think the first check was a mercy check just to shut me up.”

But for every investor worth chasing past every no, there were conversations she knew were dead and stayed in anyway. “Any time the vibes are off, I wish I would have just dropped those calls. If you know that the conversation is not going anywhere, there’s no reason to send even your materials.” She notes that a clean, respectful exit tends to make investors more curious about you than a slow drag that neither side believes in.

The investors who came through were the ones who understood the vision without needing to reshape it. Frich’s lead investor, Restive Ventures, has invested in the company three times.

“They really understood what we were trying to build. They valued that weirdness and my story and were not trying to push us toward a different direction.”

On evaluating investors, Katrin knows the product will change twenty times, the team will change, the deck will be unrecognizable in two years. The only thing that should stay constant is the core premise.

“If they push back on the vision, I don’t think it’s even your job to try to push it.”

Despite being a female-founded, immigrant-led company, minority-focused funds produced the least traction for Frich’s funding. “We actually got no traction at all with VCs like that. I still until today I’m not sure why.”

The larger lesson she took from all 109 investor conversations is about whose input actually matters. “Anyone’s early investor, early advisor, early anyone’s opinion is irrelevant if you have conviction in your idea.” She wishes she had spent less time building hypothetical four-year revenue models for investors who would never write a check, and more time in front of her actual users.

“The audience chooses. Your user or customer is what’s going to make or break your business, not what some advisor in a cushy job told you on a Zoom call.”

The Extended Marriage

Aleksandra and Katrin were best friends before they were co-founders. They shared an apartment. Katrin describes the shift plainly.

“It’s kind of like going from dating to marriage. You suddenly have this child who’s almost dying every day.”

They handled the structural side before it could become a source of conflict. Equity agreements with vesting periods were in place before Frich had any meaningful traction. “It’s kind of like a prenup. If everything goes right, which has gone right so far, we never have to use them.” Katrin is outward-facing, managing growth, investors, and partnerships. She describes herself as “the person who chats.” Aleksandra builds and executes. “She will hear me on a call talking about something that’s almost ready, and then she’s like, oh my God, we’re going to have to build this faster.”

Katrin says they historically underinvested in celebrating wins, and have worked to correct that. The startup grind produces problems every single day. The relationship needs to be fed, not just tested.

“You need to take in the win and fill your work relationship with that happiness before you go back to the war zone.”

The same philosophy extends to how she runs the company. She does not believe in the all-nighter as a marker of commitment. Her mornings run on airplane mode. She boxes, runs, practices Muay Thai, and does a weekly sauna and cold plunge session.

“You’ve got to treat your body like an athlete. You’ve got to be at peak performance. There’s no glory in treating your body like trash and then probably not being that productive.”

The culture at Frich is locked-in focus during work hours, followed by genuine rest. “This is not a sprint. It’s a marathon.”

On hiring, Katrin’s thinking has shifted with the company. Early Frich needed generalists, people with tenacity and adaptability. Scaling Frich requires specialists. “At some point as you scale, everything I believed in was no longer true. You get so much value from someone who’s been around the block for a decade or longer.”

Follow the User, Not the Room

Katrin is building Frich toward a platform version where every distinct community has its own space, its own benchmarks, and its own financial entry point. The ballerina campaign pointed to something bigger: there are entire communities of people making consequential financial decisions with no tools, no context, and no peers to learn from. First-generation workers. Creators. Blue-collar workers. Artists. Each one underserved in a different way, and each reachable if you start with their life rather than a product. The users who found Frich at 22 are now 27 and 28, and the financial decisions they make only get more complex from here.

“I really think following the user and customer is the most important thing when you’re building a business.”

Katrin builds for people who are afraid to take the wrong financial step, so they take no step at all. People who froze when asked to pick a goal because they don’t have a benchmark for what normal looks like. People who need to see someone like them make the move first. That is who Frich exists for. Katrin’s clarity around this focus didn’t originate from an investor meeting or an advisor call, but from watching her users and building for them.

The room will always have an opinion. The customer will always have the answer.

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Cosmin Nicolaescu is mid-conversation when he mentions it almost as an aside: while we’re talking, code is being written in the background. By tools he has set in motion, iterating on a product already inside some of the largest accounting firms in the United States. He will check in between meetings, course correct, and keep it moving. This is how he works.

That detail is the clearest window into how Cos built Accrual, and why the company looks the way it does.

Meet Cos, and Meet Accrual

Cos spent years as CTO at Brex, one of the most technically demanding fintech companies of its generation. He sat on the board, participated in every fundraising round, and scouted for Sequoia. He had a front-row seat to what great financial infrastructure looks like, and what happens when it breaks. When he left Brex to explore his next move, he spent time reading, traveling, and, by his own account, writing more code than he read books.

“Writing code is one of the most satisfactory things in my life. Almost every day, if I had a choice, I would end up writing code.”

That instinct pointed him toward the problem he founded Accrual to solve.

Accrual builds software for accounting firms, specifically the top 50 to 100 firms in the United States by revenue. The product helps accountants process tax returns faster and with far greater accuracy, sitting on top of existing tax engines and rebuilding the workflows around them from the ground up. This past tax season, the platform processed roughly 15,000 returns, ingested approximately 1.5 million pages of documents, and generated 99.7% of all worksheet fields using AI. Across that entire volume, fewer than 1,000 fields required a human correction.

Cos built this alongside co-founder Siddarth Chandrasekaran, known as Sidd, also a deeply technical engineer and the person who manages the majority of the builder-side work at Accrual day today.

A Neglected Market, by Design

Accounting attracted very little venture attention before the current AI era. Cos is direct about why.

“If you look at some of the modern solutions, things built over the last 10 years in the accounting space, none of them are really Silicon Valley startups. The caliber is different. The investors are different.”

The sector was considered unsexy, lumped in with legal and other professional services that generalist investors tended to pass over.

That neglect left accountants with tools built in the nineties, a constellation of three to seven disconnected point solutions that firms stitched together manually, importing and exporting between systems and losing efficiency at every handoff. The tools were not good, and the firms knew it.

“The amount of over-promise and under-delivery in this space was much higher than in other industries,” Cos said. “Over and over again, I would talk to firm owners who would tell me: we tried this tool, trained people, deployed it, spent weeks on it, and then it ended up being a disaster.”

That history of failed deployments explains why accountants often appear conservative from the outside. They have been burned by change, repeatedly, and have learned to protect their practices accordingly.

Accrual’s decision to focus on accounting firms, rather than in-house accounting teams at businesses, came down to breadth of impact. The majority of small and mid-sized businesses in the United States rely on outside accounting firms entirely. If the goal is to improve financial outcomes at scale, the firms are the lever. Internal teams at large enterprises represent a narrower slice of the work.

Cos chose to target the largest firms first, a deliberate inversion of the typical startup playbook. His reasoning rests on a principle he stated plainly: change management is harder than technology. That holds whether you are deploying software at a $5 million firm or a $100 million firm. The complexity of training staff, navigating tax seasons, and earning practitioner trust does not scale down proportionally with firm size. Given that, he reasoned, you might as well capture the complexity premium by going upmarket from the start.

There is also a structural risk that shaped the decision. Smaller accounting firms are being acquired at a rapid pace by private equity-backed roll-ups, and when a firm gets absorbed, the acquirer’s technology typically displaces whatever the acquired firm was using.

“You run the risk of going and deploying your software with these smaller firms, and then a larger firm ends up acquiring them and then displacing you because they’re like, well, whatever the acquirer uses is what’s going to be the end solution. You end up potentially spending two years on the wrong thing in a market that has high M&A activity.”

The product direction follows the same logic. Accrual started with the most complex client profiles: ultra-high-net-worth individuals, family offices, multi-entity returns, and worked outward from there. Simpler cases are a subset of that complexity, and the journey is much harder to make in reverse.

“If you start at the bottom and try to move your way up in terms of complexity, it’s really hard to prove your way versus the other way around.”

The Engineer Who Stayed

Most technical founders reach a point where the company grows large enough that management, fundraising, and strategy consume the calendar. The code stops. Cos describes that transition at Brex plainly. He needed to make it, and he understood why it was the right call. He also found it deeply frustrating.

“It’s been the most frustrating thing moving into more senior roles. At Brex, I spent the first few months mostly writing code because I wanted to learn the codebase. And then beyond that, I spent almost no time writing code just because that was not the job and not what I needed to be.”

When he reflects on how he structured Accrual, the answer keeps coming back to not wanting to recreate that condition. Today he writes code daily, though he is careful about what that means in practice. He avoids putting himself on the critical path for anything major, knowing his pace will always be slower than a focused engineer given his other responsibilities. Instead, he gravitates toward the bottom of the priority stack, features that a dedicated engineer could finish in a day or two, where a week-long timeline on his end creates no real drag. He also uses builder time to prototype new product directions and develop intuition on ideas before bringing them to the team.

Sidd, by contrast, spends roughly 95% of his time on the builder side, overseeing not just what gets built but how the architecture evolves over time.

The AI tooling has changed the practical trade-off in ways Cos finds meaningful. “Before, I would spend the next three hours on one problem. Now I can spend those three hours on five things at once.” He puts the practical ceiling at two to four concurrent workstreams before output quality starts to degrade. Beyond that, he said, “it probably ends up becoming slop if you don’t pay enough attention.”

He has also developed a pointed opinion about the “I had to stop coding” narrative common among senior engineering leaders, one he offers as a personal observation rather than a researched claim. In his experience, founders and executives who genuinely love writing code return to it the moment they have unstructured time, between jobs, on weekends, wherever they can find it.

“My spicy thought is that most folks who move up the management chain don’t actually enjoy building code as much as they enjoy management. It’s very few engineering leaders who use time between jobs to just write code, despite the fact that they hadn’t done it in their job.”

The harder adjustment, he said, has been learning to work with people who operate at a different analytical pace. Early on, when a prospect would go quiet after a pilot, his instinct was to diagnose it as a product failure. More often, it was simply the rhythm of their world. “Assume good intent and don’t read into it until someone explicitly tells you something” is now a principle he tries to hold onto.

Cap Table as Culture

Cos came into fundraising with context most first-time founders do not have. He had been present for Brex’s rounds, participated in board meetings as a CTO, and spent his gap year in deliberate conversations with investors at top funds, not to pitch, but to understand how they think. That background informs a framework for investor selection that is more deliberate than the standard advice.

His first principle is quality over quantity. A small check from an investor who is not genuinely bought in creates more downside than most founders account for. That investor might pass on the next round, fund a competitor, or simply not return calls when the situation gets complicated.

“If investors are not really bought in, they don’t really care that much. They won’t necessarily hurt you, but they might not spend that much time with you either.”

His second filter for investor selection: whether he actually wants to spend time with the person.

“I’ve seen founders where they hate the idea of meeting with this investor. They’re a pain in the ass. And I tell them, why did you let them on your cap table? It wasn’t even that they had no choice. They just didn’t think through that angle.”

His third consideration is time horizon clarity. A seed-stage investor who is excellent at the earliest stages but adds little value by Series B is a known limitation, and that needs to be understood before the check clears. Discovering it years later is a different problem entirely.

“I’ve seen investors go with seed funds and feel very good about it, and then several years later they’re like, that seed fund investor is not helping me at all, but they still own 10% of my company. I’m like, yeah, but that was very obvious in hindsight.”

Cos is candid that his network access is not typical. The ability to be selective with investors is partly a function of having the right early traction and the right relationships coming in. Still, the underlying principle applies more broadly: founders tend to have more agency over their cap table than they exercise, and the cost of ignoring that surfaces years down the road.

When the Product Proved Itself

Cos describes two inflection points that mattered most. The first was technical: proving that Accrual’s integration with existing tax engines could actually work, that accountants could experience their workflows as something fundamentally different rather than incrementally improved. That came together in the summer before their first live traffic, then got real confirmation during extension season.

The second was harder to engineer: unsolicited feedback from end clients. High-net-worth individuals who had no direct relationship with Accrual, some of whom Cos had never met, reached out to say their experience working with their accounting firm had noticeably improved.

“Until you actually have that sort of live traffic, it’s really hard to get confirmation that the bets you’ve made will pay off. Getting that confirmation was extremely rewarding.”

That confirmation points toward what Accrual is ultimately building toward. Cos’s thesis is that the tools available to accounting firms have historically driven one outcome: efficiency. Getting the books closed faster, reducing hours per return, cutting outsourcing costs. Those gains matter, but they do not grow a firm.

“Our thesis was always that while we’re optimizing for the accountants, there’s an end client that they’re serving whose primary optimization is time.”

If the client experience improves meaningfully, firms using Accrual should see higher growth, not just higher efficiency. That is the differentiation Cos believes the industry has been missing. The accounting software market has spent decades solving for the accountant. Accrual is betting that solving for the client changes the economics of the whole firm.

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Carlos Chavez doesn’t sell in the traditional sense. He walked into investor meetings for Sytrex looking for the answer to a couple simple questions: How does this investor view the world? Do they believe what I believe? He was there to find out whether the investors across the table shared his thesis. The result? Seven term sheets.

With two successful companies behind him, Carlos learned to lead with conviction rather than salesmanship, whether he’s talking to prospective customers or future investors. “If that person that’s on the other side of the table doesn’t believe in your vision of the world, then it’s obvious why you should not continue the conversation. The fundamentals that you believe are different.”

In his early days as an entrepreneur, he admits to the natural instinct of approval-seeking, scarcity thinking, or trying to win over every room he walked into. But he realized this fundraising persona was undermining the power of authenticity.

Today, whether he’s across from prospective investors or closing the next customer, Carlos cares more about finding alignment with the person on the other side of the conversation. “If somebody believes in [the reason you’re building], it’s gonna be automatic why that person wants to be involved with you in business.”

Sytrex recently crossed $1 million in annual recurring revenue, all through founder-led sales. Carlos and co-founder Danny Palacios have personally closed every customer on the books.

From the Reinsurance Table to the Founding Table

Carlos grew up in an entrepreneurial family, watching his parents run their own companies from an early age. His family also owned a reinsurance brokerage firm. Entrepreneurship was the baseline in his household, the example he saw modeled every day. As he puts it, when that is normal, you are simply more accustomed to doing it.

Chavez has a simple question to determine whether something is worth his time. “Does this give me energy?” Entrepreneurship, apparently, does.

He launched his first company in healthcare, a sector where insurance touches almost everything. His second business was in real estate, where he again encountered the insurance industry. By the time he founded Sytrex, Carlos had been navigating the chaos of insurance across multiple contexts for years. He describes the sector as messy, document-heavy, and full of pieces that do not connect to each other. That familiarity, combined with what he calls a lifelong pull toward the space, is what brought him to build in it directly.

What Sytrex Actually Does

Sytrex builds AI-native infrastructure for the insurance industry. Carlos describes it as the “glue that’s in the middle of everything,” sitting between a sector where the pieces have never connected well. The platform integrates with the major systems of record that insurers already use, including Guidewire, Duck Creek, Salesforce, PPL, Whitespace, and VIPR, and layers agentic workflows on top of those connections.

The practical result is that insurance companies can automate end-to-end operations using agents that carry embedded industry knowledge. One example Carlos gives is an agent that already understands what underwriting property in Texas involves, the technical mechanics and the business logic specific to that geography and line of business. Companies can also configure agents to reflect their own internal processes, so the system works the way their organization works.

Building the Team Around a Simple Test

When it comes to hiring, Carlos looks for candidates who are genuinely hard to get. If recruiting someone feels too easy, he takes that as a signal he may not be aiming high enough. The people worth pursuing, he says, usually have a lot of opportunities and they know it.

His interview process includes a specific tell he listens for. The signal is when a conversation with a strong candidate starts to feel like a class, when the person is teaching him things he did not know and he finds himself wanting the conversation to keep going. He also keeps a handwritten notebook where he records the names of standout people mentioned across all his interviews. Ask enough candidates who the best person they have ever worked with is, and the same names start appearing. That list becomes the hire list.

In the current environment, Carlos prioritizes soft skills and attitude over specific technical capabilities. The tools Sytrex uses today may not be relevant in six to eight months. Someone with the right disposition will learn the new ones. As Carlos puts it, “it doesn’t really make sense to me to bring in people to the team based on a unique hard skill,” because models will eventually handle those capabilities anyway.

On the AI-native side of the team, Sytrex runs agents across sales development, content creation, design, and coding functions. But Carlos is careful about what gets green-lit. Before the team creates a new workstream, they ask one question: Can at least 80% of the execution be automated? If the answer is no, the opportunity cost usually makes it a poor trade.

Culture as Fuel, Not Decor

Carlos is candid about how culture can look to early-stage founders: a heavy lift with a low immediate return on investment, easy to defer until the business is more stable. The lesson he has taken from building multiple companies is that the return is very real, it just shows up in less obvious ways. Getting culture right, he says, is “a huge accelerator,” and getting it wrong decelerates a company by just as much.

At Sytrex, four cultural pillars govern how the team executes. First, extreme accountability means that once a number or a timeline has been committed to, that commitment is fixed. There is no renegotiating after the fact. Second, bias for action means people are expected to exercise judgment and move, not wait for permission. Third, an emphasis on thoughtful disagreement means Carlos is actively building a team that argues with evidence and pushes back when they think he is wrong.

“You don’t want a committee of people clapping at you because no one person can have all the good ideas.”

The fourth pillar is intellectual curiosity. When someone on the team discovers a new tool or technology and brings it back to the group, the whole team learns from it. Carlos describes the effect simply: if you have 10 different people reading and learning and having 10 different conversations, and they bring that back, everyone benefits.

In the past year, Carlos has brought the full Sytrex team to San Francisco three times, each for a full month of in-person work. The team lives together, runs internal hackathons, and opens the space to interactions with other companies. When asked about the cost of in-person meetups, his thinking is clear: if you’re building toward a billion-dollar outcome, that expense is marginal. The information and conversations that come from that kind of team proximity can change the outcome in ways that are infinitely powerful, if harder to quantify.

Fundraising as a Worldview Test

Carlos describes his early approach to fundraising as trying to be “that golden coin that everybody wants.” What shifted was his willingness to walk into a meeting with a genuine thesis: how he thinks the world is going to evolve, what bet he is making on that view, and whether the investor on the other side of the table sees it the same way. If they do not, Carlos says, that is normal. It is an obvious reason to move on. As he puts it, if the fundamentals you believe are different, the conversation should end there.

The Sytrex seed round generated seven term sheets because Carlos applied that filter consistently. He also ran simple qualification tests early in conversations with potential investors. Basic questions about whether they are using AI tools themselves, or whether they have built their own agent, reveal quickly whether someone can engage substantively with the decisions Sytrex will actually face in a boardroom. He also paid attention to whether investors were willing to make introductions on request. From that, he says, "you get a sense of the potential value that they could bring to you later."

For future rounds, his framework shifts based on stage. Pre-seed and seed rounds are bets on people, so the strongest conversations happen with investors who already know you. Series A and beyond should be raised on inflection points, with the clearest possible signal that a distribution channel is repeatable and scalable. When you have that data and can show it, Carlos says, “that’s the easiest sell in the world.”

Playing the Long Game from the Right City

Carlos made a deliberate decision to base Sytrex in San Francisco, and he is candid about what it required. Family-wise, San Francisco is very far from Colombia, and the cost of living demands real trade-offs. He made the move because the pace of what is happening in the city, he says, is unlike anything he has seen elsewhere.

He travels frequently for work, visiting London, New York, South America, and Dubai. Nowhere, according to Carlos, matches the speed of San Francisco right now. He has had conversations on a Monday that changed how he was thinking about a problem, only to change again by Thursday as the conversation evolved around him. That kind of environment, he says, is “such an unfair advantage” if you are inside it. The density of people building in AI, the quality of the dialogue available on any given day: these are things he has not found replicated anywhere else.

The work ahead for Sytrex is to continue building the connective infrastructure that a fragmented, document-heavy industry has long needed, now with a team past $1 million in ARR, a clear sales process, and the kind of cultural foundation Carlos spent two previous companies learning how to build correctly. He is exactly where he wants to be, and by his own measure, the energy has not let up.

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When Dori Yona needed to figure out how to shut down his startup, he did what most people do when they’re lost: he Googled it.

It was late. He had just come home from a board meeting where investors told him his company, a consumer fintech called Earny, was running out of runway and needed a shutdown plan. He sat down and searched “how do you shut down a startup,” expecting to find a clear process or a service built for exactly this moment. What came back was a blog post from a boutique law firm that looked like it had not been updated in two decades.

That gap between what founders need at one of the lowest moments of their professional lives and what actually exists for them is the entire reason SimpleClosure exists. And Dori’s willingness to plant a business in that gap, in a space most of the startup world treats as taboo, is what makes his story worth understanding.

The Founder Behind the Company

Dori is a serial founder now in his mid-career, running his third company from Santa Monica with four kids and a wife at home. He grew up in Israel, served as a captain in the Israeli Navy, and started his first company in 2014, a mobile dating app that launched before Tinder had fully defined the category. His research process for that product included signing up for every competitor platform available, including Ashley Madison, a detail that became unexpectedly relevant years later when the site suffered a massive data breach. He had to warn his wife in advance. She knew. He had shown her everything.

When asked how he stays a high-performing CEO, his answer bypasses the expected talk of morning routines and workout schedules. “I actually think that having a very supportive wife and kids and family helps me be a higher performing CEO,” he says. “I could not imagine a world where I came home and didn’t have a supportive family and support system.” For Dori, the foundation of his performance at work is built at home.

That same instinct to go all the way in, to use and understand what he was building before claiming he understood it, runs through everything he has done since. SimpleClosure is not a pivot or a trend play. It came directly from personal experience and from listening to dozens of other founders describe the same experience after the fact.

What SimpleClosure Actually Does

SimpleClosure is a platform that helps companies wind down their operations in an organized, legally sound way. The problem it solves is not just paperwork. It is the entire hidden infrastructure that founders need when they decide, or are forced, to close: understanding severance obligations, resolving office leases, managing vendor liabilities, filing the right state and federal dissolutions, and avoiding the kind of financial exposure that can follow a founder long after the company is gone.

More recently, Dori’s team launched a product called Asset Hub, which helps shutting-down companies monetize the value they have left: code bases, workspace data, domains, patents, trademarks, and in some cases the talent on their teams. The idea is that a company coming to SimpleClosure to close should ideally leave with more money than it arrived with. According to Dori, that has already happened for customers who came to the platform with barely enough to cover shutdown costs and walked away with six figures.

A Market Hiding in Plain Sight

Most people assume the shutdown market is small because they never see it. No one posts about it on LinkedIn. Founders quietly remove failed companies from their profiles or describe their tenures in ways that obscure what happened. The silence creates the impression that this is a rare event, when the data says otherwise.

In the United States, roughly 4 million companies close every year. About 1 million of those have employees. The number that incorporates in a given year is nearly identical, which means the overall count of active businesses in the country has stayed roughly flat at around 30 million for decades. Dori started SimpleClosure focused entirely on venture-backed and technology startups, but the platform has since expanded to serve the broader small and midsize business market. Based on how states categorize industry data, Dori estimates technology companies represent somewhere between 10 and 15 percent of annual closures.

The market is not small. It is just invisible.

Three Parallel Workstreams Nobody Can Know About

When a startup begins its decline, the founder rarely gets to deal with just one problem at a time. Dori describes what he hears from customers as three simultaneous workstreams, each one requiring a different story to be told to a different audience.

First, the founder is still trying to run the business. Second, they may be in active conversations with existing or new investors, selling optimism and forward momentum. Third, they may be quietly exploring whether the company can be sold for whatever it can get. Each of these tracks has to stay separate because the moment any one group learns about the others, the whole situation collapses.

“Your employees, your partners, your customers, your investors,” Dori says. “Like it’s all, you’re kind of doing something behind the scenes.”

The only people typically inside the full picture are co-founders, if any are still around, and a senior finance person. Everyone else operates on incomplete information while the founder holds the rest together. It is a structural loneliness built into the final phase of a startup.

Why Grit Becomes a Trap

Dori does not use the word “failure” much. He has clearly thought carefully about how language shapes a founder’s ability to make clear-eyed decisions under pressure.

The core problem, as he sees it, is that the qualities that make someone a capable founder are exactly the qualities that make it nearly impossible for them to call it quits. Founders are trained to believe in tenacity, grit, and persistence. They carry examples of it in their heads constantly: the Airbnb founders who sold cereal boxes when they ran out of money, the Slack team that pivoted from a failed gaming company, the entrepreneur who put $50,000 of personal debt on a credit card and turned it around. These stories reinforce the idea that running out of options is never a valid reason to stop.

Even the word “shutdown” carries psychological weight. Dori recalls that at his previous company, he and his co-founders were all privately wondering whether they needed to close long before anyone said it out loud. To name it was to accept it. So no one named it.

“It goes against everything in your soul to do it,” he says.

His framework for when to actually make the call is less about specific financial thresholds and more about a gut check: do you still believe this can become a large business, and are you still genuinely excited to be building it? If both answers are honest yeses, then the more analytical questions about market size, economics, and product fit are worth working through. If the excitement is gone, no amount of logic saves the situation.

For the business outcome, he also notes that many founders wait too long for a cleaner exit. Companies that could have been sold at a decent price a year or two earlier become unsaleable by the time the founder is ready to consider it. The peak is only visible in hindsight.

What Founders Say Six Months Later

Dori makes a point of staying in contact with founders after their shutdowns, not just while they are in the process. The contrast between those two conversations is part of what keeps him motivated.

When founders are in the middle of a shutdown, they are often in one of two places. Some come in fragile and emotional, having spent years tying their professional identity to a company that is now closing. Others come in pragmatic and direct, focused on logistics and ready to move on. Most land somewhere between those poles.

But when he talks to those same founders six or twelve months later, the pattern is consistent. Almost all of them say they wish they had done it sooner. The relief is real, and the forward motion that follows tends to be faster than expected. Dori says 65 to 70 percent of founders using the SimpleClosure platform are already starting their next company while they are still in the shutdown process.

That number is the actual reason he built this. Not the legal filings or the asset liquidation, but the part after it.

Getting Founders Back to Building

Dori’s pitch for what SimpleClosure ultimately is has nothing to do with shutting things down. The mission, as he frames it, is about compression: taking a process that historically consumed a year of a founder’s life, burned their savings, and left them exhausted, and condensing it into something manageable enough that the founder can get back to the next thing.

“How do we get these founders back to building as fast as possible?” he says. “That’s ultimately what drives us.”

The company is hiring, growing its platform, and expanding beyond its original tech-startup core into the broader SMB market. Asset Hub is new and expanding. The VC community, which was initially slow to understand the thesis, has started to come around as traction has built.

He has seen the worst of what happens when founders try to navigate shutdown alone. His bet is that the ecosystem is better when that process has real infrastructure around it, and when the founders who go through it come out the other side ready to build something new.

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Dr. Ashley Benne built her entire identity around becoming a surgeon, achieved it, and then chose to walk away from it completely. The piece centers on what it actually takes to shed a hard-won identity and start over from scratch, including sleeping on couches, being thrown out of offices, and learning an entirely new language of business while still fluent in the old one.

The Identity You Have to Leave Behind

Most people work their whole lives toward a goal. Fewer actually reach it. And almost none of them walk away from it once they do.

Ashley, co-founder and CEO of Rue Four, spent her entire childhood pointing toward medicine. Her mother’s side of the family is full of pediatric and prenatal surgeons. By the time she was eight years old, she was handing out Tic-Tacs to neighbors and telling them she was curing them. That was not a hobby. That was a preview. She went on to practice reconstructive hand and burn surgery, completing one of the most demanding professional paths available to anyone in any field.

Then she left.

What made her go was not dissatisfaction with medicine. It was a recurring frustration that the tools available to doctors were failing them in basic, fixable ways. Fragmented systems, paper charts, and workflows that had no business existing in a modern clinical setting. Ashley was wasting time on infrastructure, not patients.

“I always felt like what I was doing could be a lot more efficient,” she said. “That was the first thing that showed me.”

She started small: a no-code app, something closer to a well-organized spreadsheet with a cleaner interface. She shared it with colleagues. They used it. And then she started wondering whether the problem was big enough to build a real company around.

Meet Rue Four, and the Sister Who Co-Founded It

Rue Four is building an operations platform for medical practices. The company connects clinical workflows to the financial and administrative systems doctors rely on, creating what Ashley describes as a single front door for communication between teams that rarely share the same information. The target customer is a surgeon or practice owner who is moving fast, has no patience for friction, and would rather focus on patients than toggle between five disconnected tools.

The company she built to solve this problem was co-founded by her sister, Jessica de Mier, who came from a journalism career that included time at CNN. The two of them grew up moving across continents, including stints in Germany, California, Mexico, and Spain, and their closeness as siblings traces directly to that peripatetic childhood. When you keep changing schools and cities, you hold onto whoever stays constant.

Jessica is the growth engine and Ashley executes. “Jessica’s a little bit more of a visionary and a dreamer,” Ashley said, “and that balances out someone like me, who gets really deep in the details.” Their roles do not overlap much, which is part of why the partnership works.

When investors first learned they were siblings, reactions were mixed. Typically, investors were already 20 conversations deep into due diligence. “I mentioned it down the line,” she said. She believes their relationship is one of their biggest superpowers.

Getting Kicked Out on Fifth Avenue

The first serious test of whether any of this was real came when Ashley stopped building for herself and started trying to sell to others.

She was in New York, working out of a “WeWork” on 18th Street, and she needed early customers. So she went to get them the only way available to her: walking up and down Fifth Avenue in the cold, knocking on doors at plastic surgery practices. “Nine out of 10 times I got kicked out,” she said. Surgeons were in surgery. The front desks had no idea who she was. Nobody was interested in whatever a stranger was selling from the street.

She tried paying for lunch-and-learns to get five minutes of a surgeon’s attention. She tried booking patient appointments. She did whatever it took to get face time because cold emails and calls were getting her nowhere.

What eventually worked was credibility. Once a practice realized she had actually been a surgeon, the dynamic shifted. She walked into a plastic surgery office on the Upper East Side, pitched the founding surgeon on the product, and walked out with her first angel check: $50,000. He had first tried to hire her. When she made clear she was going to start the company, he invested instead.

“For any founder,” she said, “the first time you find a paying customer or someone who believes in what you’re doing, that was enough for me.”

Two months later she left medicine entirely.

That transition was not clean. She had no apartment in New York. She was sleeping on friends’ couches while launching a product and learning a profession she had never trained for. The financial language, the operational language, the venture language: all of it was new. She had spent years mastering how to mend a broken bone. Now she was figuring out what an engineering manager actually does.

“Ask me two years ago,” she said, “I would have never thought I would be doing this.”

What Building Actually Looks Like

The early mistakes were predictable in retrospect but painful in the moment. Hiring moved faster than judgment. The initial go-to-market approach created friction that only became visible after repeated failure to grow past it. “I was approaching it from the wrong side,” she said. “I realized I was going to bang my head against the wall a million times.”

The correction required slowing down, interrogating the assumptions baked into the product, and reframing who it was actually for and how it was being sold. Rather than treating the pivot as a failure, she used it to fuel her initial assumptions. The learning-from-mistakes posture she developed in medicine, where the stakes of overconfidence are permanent, carried directly into how she runs the company. “Surgeons, you’re always kind of learning with what’s happening,” she said. “You never grow out of imposter syndrome in the clinic, and it keeps you very humble.”

On hiring, she has landed on a framework that several of her peers recommended: take your time bringing people in, and move fast when something is not working. When evaluating whether someone belongs on the team, she asks a simple question: Knowing everything she now knows about this person, would she hire them again? If the answer is not a confident "yes," she treats it as her answer.

Her broader philosophy for navigating decisions she does not yet know how to make is equally direct. When she needed to build out an engineering team, she cold-messaged Uber's former chief technology officer on LinkedIn. He responded. One conversation led to introductions, and some of those introductions became the engineers now leading Rue Four’s technical team, people who came from Uber and DoorDash. “One of them ended up leading our team,” she said.

That approach, asking people who have already done the thing, has become her primary operating system. She calls friends with companies when deals start going sideways. She reaches out to people she has never met when she hits a question she cannot answer alone.

“You’re only as smart as what you know,” she said. “The ability to just ask people has 10x’d anything I could have done by myself.”

This is a meaningful shift from the culture she trained in. “The motto in the clinic was, at the end, you’re always alone,” she said. In a tech company, that kind of isolation is a liability.

Where Rue Four Goes From Here

In 2026, Ashley’s focus is on building the team that can carry the product to the next stage. Rue Four has onboarded hundreds of clinics and is continuing to grow. The engineering team is expanding. The product roadmap includes Agentic workflows, AI forecasting and streamlining supply chain built specifically for clinical operations, capabilities that did not exist in a form that worked for the people who needed them most.

The vision is to make modern operational infrastructure available to every medical practice, a category that has historically received less attention from technology builders than its size and complexity warranted. Ashley sees AI as the accelerant that makes this moment different from what came before.

But the North Star she returns to is simpler than any roadmap. “When I have a doctor get on the platform for the first time and say, you’ve changed my day-to-day,” she said, “that’s what makes me so bullish on the decisions we're making.”

She built her first career around the idea that one person with the right training could help one patient at a time. She left that career when she realized the math could be better. The identity she shed to get here was not a sacrifice. It was a trade: one kind of impact for another, larger kind, scaled through software instead of surgery.

This season is supported by Perkins Coie. Perkins Coie is a leading international law firm known for providing high-value, strategic solutions. The Emerging Companies and Venture Capital team counsels startups and the investors backing them, supporting clients from formation through exit. In the past three years, clients have raised more than $23 billion in private markets between the pre-seed and growth stages. Perkins Coie combines tailored counsel with sector experience, so when it’s time to accelerate, whether for the next financing round, a strategic deal, or going public, your team is ready. To learn more, visit perkinscoie.com

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By the time CK closed his second company’s $510 million acquisition, he had not taken more than two consecutive weeks off in roughly 20 years. Not during the dot-com boom. Not through four years at Google. Not through nine years of building a mobile publishing platform from a napkin sketch to a near-institutional exit. The only real pause in his adult life had been his honeymoon.

For most founders, the narrative would end there, somewhere between the wire transfer and the celebration dinner. For CK, that moment was less a finish line and more a hard stop sign he finally had the permission to read.

From Seoul to Silicon Valley, One Accidental MBA at a Time

CK did not grow up thinking about startups. He grew up in Korea in an academically rigorous household. His father, a university professor, set an expectation that anything short of a PhD represented personal failure. CK aimed for medicine, studied natural sciences, and enrolled at the University of Michigan, though military duty pulled him back to Korea before he could finish his degree.

That detour, as it turns out, was the sharpest education he ever received. The Korean government ran a program during the dot-com era allowing men to fulfill their mandatory military service by working at designated tech companies. CK landed a role at a 30-person startup with no engineering background and no business training. He was, by his own description, cheap labor. When nobody else could handle the non-technical work, including fundraising materials and eventually the company’s listing on the Korean Stock Exchange, it fell to him.

“I was grumbling a lot,” he said. “I was working until midnight. But in hindsight, that was the best real-life MBA I could ever have.”

The company grew from 30 to 300 people during his tenure and went public. Then, like many ventures that succeeded too fast during that era, it struggled under the weight of its own capital. The IPO was successful enough to attract investors and partners with ideas in every direction, and the discipline that had built the business gave way to scattered priorities. CK watched it happen and filed the lesson away.

After completing his degree at Michigan and a four-year stint at Samsung, where he kept one foot in the startup ecosystem even while drawing a corporate paycheck, CK co-founded his first real company with a serial entrepreneur named Chester. They built the leading blogging software platform in Korea during the Web 2.0 wave, growing the service into the country’s top destination for content creators. Three years in, Google came calling.

Korea is one of only three countries in the world where Google does not hold majority search market share, alongside Russia and China. A dominant local player had walled off its content from outside indexing. Google’s response was to acquire a content platform of its own. CK and Chester’s company fit the brief. The deal took nearly a year to close, and on a Friday it was done. CK was at the Google Seoul office on Monday morning.

Nine Years, One Number, and What It Actually Cost

The Google chapter lasted four years and carried CK to California, where he eventually earned his green card and his fully vested stock. Before he officially left, he had already been quietly building the foundation for his next company on evenings and weekends, refining the idea for six or seven months before making any move. That preparation mattered, because what came next was not a sprint.

His second company operated in the mobile publishing and storytelling space, a content creation platform built for the smartphone era. It took nine years to reach acquisition. The exit price was $510 million.

The financial outcome rippled outward in ways CK still speaks about with visible satisfaction. The company had about 70 employees at the time of the deal. Roughly 15 percent of them became millionaires. Investors who came in at the Series B, a round of approximately $7.5 million, achieved a 30x return. Earlier investors did considerably better. “I was really happy about that,” he said simply, and the simplicity of the statement was its own kind of credibility.

But nine years is a long time to carry something. CK describes the founder experience during those years as permanently occupying one edge of his awareness, even when the business was performing well. Sleep was difficult. Stress was ambient. He was expected to project certainty in every room, regardless of what he actually knew. “You’re supposed to know things,” he said. “You’re supposed to be the smartest person in the room even though you may not be.”

When the deal closed and he eventually walked away from the acquiring company two years later, he made a decision that no previous version of himself would have made. He would take a year off. He ended up taking a year and a half.

What Listening Taught a Lifelong Builder

CK approached his sabbatical the way most founders approach a product launch, with research. He read Lenny Rachitsky’s newsletter piece on the subject, absorbed the recommendation that a year is the minimum useful duration, and then did something fundamentally out of character: he refused to make a plan.

“I wanted to kind of unlearn that,” he said, referring to the reflex to schedule and optimize. “I’m not doing work here, so let’s not plan things and see what happens.”

What happened surprised him. He started meeting people. He invested as an angel in 55 companies and participated in a number of funds. He took calls that gave him energy rather than drained it, a distinction he had never meaningfully considered before. Having moved from the Bay Area to Los Angeles in 2020, he deliberately sought out people outside the technology world, people working across entertainment, hospitality, and any number of other industries. He asked them a single question: how is your life going?

“People would speak for 20 or 30 minutes,” he said. “People want to be heard and they have amazing stories.”

His wife noticed the change before he fully did. She told him he was a different person. Coming from the person who had watched him work through 20 years of uninterrupted intensity, including the sleeplessness and the constant edge of stress, he took that seriously.

The sabbatical also produced a question that became the seed of his current company. A friend suggested an exercise: imagine a doctor tells you that you have three years to live. What would you do immediately? CK’s answer included a desire to share what he had learned, to write more, and to build something that helped other people express and distribute their own knowledge. He had built blogging platforms and storytelling tools twice before. This time, he wanted to do it with artificial intelligence.

Building the Platform That Listens Back

CK is the co-founder and CEO of Saywise, a company that uses AI to help people extract and share their knowledge through conversation. Rather than asking users to write, Saywise asks them to talk. The platform generates topic suggestions and talking points, then conducts a voice or video conversation with the user, or calls them directly by phone. The AI listens, asks follow-up questions, and transforms the exchange into polished written content or video.

The premise is a deliberate inversion of how most AI content tools work. “There’s so much AI-created content and it’s going to flood the internet,” CK said. “What we want to do is take it upside down. What if humans continue creating their authentic content, but AI is helping them?”

The 2026 roadmap centers on building team-based use cases, allowing companies to use Saywise to involve multiple contributors and keep company accounts active and substantive. The platform is also integrating with meeting notes, internal tools like Notion, and employee profiles to surface content opportunities from existing internal discussions.

For CK, the arc from a Seoul military posting to a $510 million exit to a platform designed around human expression is not a detour. It is a straight line. Every company he has built has placed the act of sharing knowledge at its center. The only thing that changed during the sabbatical was who was doing the listening.

“What would I do if I’m not doing this?” he said, describing how he kept going through the difficult years of his second company. “I’ll probably do something about content creation. That’s the same thing I’m doing right now.”

He kept going then. There is little reason to expect anything different now.

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There is a particular kind of pressure that comes from being right about something before anyone else agrees with you. John Taylor Garner knows this well. In late 2021, he and his co-founders shut down their first company and pivoted to a new thesis: that airlines and hotels had quietly broken their loyalty programs during COVID, and that the credit card industry would soon face a churn crisis because of it. The only problem was that nobody had noticed yet.

For roughly two years, John built what would become Odynn in near-complete stealth, selling a solution to a problem that was still invisible to the banks he was pitching. “We were a little early,” he says, with the calm of someone who has since been proven right. “But it also took a while to build out all the tech, so it ultimately didn’t matter.”

That ability to stay the course on an unconfirmed thesis, without external validation to lean on, is the through-line of John’s story as a founder.

From the Trading Desk to the Builder’s Table

John spent six years at Merrill Lynch as a volatility trader, eventually running the International National Macro Cross-Asset Volatility book on the index desk with record profitability. The role covered currencies, commodities, fixed income, high yield, and emerging and developed markets simultaneously. He describes the appeal of it plainly: “It is impossible to fully manage everything. You’re always one step behind, which sounds annoying, but it was actually what made it engaging.”

That comfort with managed chaos would prove useful later. Trading floors are finite, though. Markets close. Founders are always on. The transition required a real adjustment, and John acknowledges it. He now frames his earlier career not as preparation for pressure, but as a different category of it entirely. A senior contact at a large bank recently told him he might be the only founder they had met who had taken a less stressful job by leaving trading. He paused when he heard it. “I hadn’t thought about that,” he admits. “That is a valid point.”

Before launching Odynn, John built Card Curator, a mobile super-app for credit card management that he describes as “a fully automated version of NerdWallet.” He began working on it at the end of 2018, and the early traction was strong enough to justify building it out fully. Then COVID arrived and gutted the travel category the product depended on. He went to Wharton for his MBA, continued working on Card Curator during that time, relaunched it in January 2021, and grew it to roughly 40,000 monthly active users. The team, by his own description, knew nothing about B2C marketing. They grew anyway, largely because the product resonated.

The end came when airlines and hotels shifted from static to dynamic loyalty pricing. The recommendation engine Card Curator had built became unreliable overnight. Rather than rebuild it, the team made a sharper call: go build the dynamic pricing infrastructure itself and sell it upstream to financial institutions.

That decision became Odynn.

The Problem That Took Two Years to Become Obvious

To understand what Odynn does, it helps to understand what happened to loyalty programs during the pandemic. Airlines and hotels, which generate the majority of their profits through loyalty programs rather than core operations, needed liquidity fast. The solution was to sell points and miles in bulk to their banking partners. Amex, Chase, Citi, Capital One and others bought billions of dollars worth of them to help keep travel suppliers solvent.

The result was predictable in hindsight. Flooding a market with currency while keeping its price pegged causes rapid inflation. When the peg eventually had to float, airlines and hotels shifted to dynamic pricing for redemptions. Points that once bought a predictable flight now bought an uncertain one. Most cardholders did not notice immediately, because most cardholders were not traveling.

By late 2023, that changed. The first visible signal was Delta’s October 2023 standoff with Amex over lounge access, status earning, and point payouts. Longtime Delta loyalists left for other carriers. The underlying cause was structural: Delta, like every major airline, had sold so many miles during COVID that it could no longer honor the old terms without going backward financially.

“It turns out we were right,” John says. “And it turns out churn is at all-time highs for these cards and only increasing.”

Odynn sits at the intersection of this problem and the financial institutions trying to solve it. The company builds travel portal infrastructure for card issuers, complete with embedded loyalty solutions that help cardholders understand what their points are actually worth in real time. Customers include banks and fintech platforms that want to offer a fully branded, modernized travel experience without building the underlying tech themselves. John describes the vision as “a Shopify for travel portals.”

The competitive landscape is remarkably concentrated. John names four major players in embedded travel: Expedia, Booking, Hopper and Arrivia. Between Expedia and Booking alone, more than 80% of the market is accounted for. Every one of those companies is valued in the billions. Odynn is the sixth.

The Investor Search in a Niche Within a Niche

Finding the right investors for a company this specialized required recalibrating what “relevant experience” even meant. John was direct about his criteria. Financial capital was the baseline. What he actually screened for was domain expertise.

“There are really only five major players,” he explains. “So if you’re taking a step back, there’s only a limited set of individuals that can really provide that insight for us.” A pure embedded travel background was nearly impossible to find in a VC. So the team expanded the filter to include loyalty experience, fintech experience, or adjacent travel verticals, and looked for any meaningful combination of those.

Bonfire Ventures led the round, with Fiat Ventures co-leading. Odynn raised $9.5 million in a seed round that was completed at the end of 2025 and announced in February 2026. John’s confidence in Bonfire came partly from watching their work with Wildfire, a portfolio company on the retail loyalty side. Fiat’s roots were in embedded fintech, which mapped directly onto what Odynn was building. “It’s kind of a perfect match,” John says.

His broader point to founders thinking about investor relationships is worth noting. He does not distinguish between financial and non-financial value as though one is primary. For him, a check without relevant knowledge attached to it is a diminished asset in a vertical this narrow.

Staying Grounded When the Market Hasn’t Caught Up

John runs a team of 28 people, 19 of whom are engineers. His co-founder and CTO Anuj Patel, who he met at Wharton, leads the technical side. John focuses on fundraising, investor relations, sales, go-to-market, and overall strategic direction. He also taught himself Python to build the core algorithm behind Card Curator and Odynn, and vibe-coded the company’s agentic AI travel concierge during the summer of 2025 because he had a specific vision for how it should work.

He is candid about what keeps him level during the harder stretches. Going for a run is his most reliable reset. “If I’m working on a problem and I can’t get over it, removing yourself and clearing your head a little bit, you’ll come back with new ideas or a new approach.” He travels extensively, often taking calls from beaches, ski mountains, or wherever he happens to be, because the flexibility of not being office-bound is something he protects deliberately. He also credits his wife, a PhD in clinical psychology, as what he calls his “secret sauce.” “I kind of have an in-house therapist,” he says. “Very few people can take advantage of that though.”

The motivation underneath all of it is structural. The loyalty industry has always wrestled with whether a loyalty program is a cost center or a revenue driver. John’s view is that it is always both, but only the companies that treat it as a long-term investment get the return. “Every dollar invested into a successful loyalty program should be paying between five and 10x back,” he says. “Not immediately. This is a multi-year long investment.”

The Roadmap Ahead

By mid-2026, Odynn expects to have transferable loyalty live, with select partners already lined up. Luxury hotel offerings comparable to Amex’s Fine Hotels & Resorts program are in the pipeline, along with the full rollout of car rentals. The agentic AI travel concierge, currently in beta with active customer testing, is expected to move to production before year end.

The most significant milestone on the horizon is a fully self-managed version of Odynn’s modular infrastructure. The current version is already live for customers in production. The self-managed release would allow clients to build their own travel portal independently, using modular SDKs, APIs, and model context protocol access so that large language models can handle the build process directly.

The company that John describes is one still assembling its final form. But the thesis it was built on, that cardholders would eventually notice their points were worth less than expected, that churn would follow, and that financial institutions would need better tools to respond, has held up. Being early, it turns out, was not the same as being wrong.

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It all started with conversations. A lot of them. The salespeople Steve Ancheta called didn’t know each other and they worked at different companies, in different cities, at different stages of growth, from Fortune 10 corporations to early startups. He asked each of them to walk him through their ideal week in sales: what they should be doing, what they actually do, and how those two things differ.

Every single answer was different, until it wasn’t.

No matter when it fell in the week, Monday morning or Thursday afternoon, each salesperson described a block of time they had to set aside for tasks that had nothing to do with selling. CRM updates. Follow-up notes. Lead research. The details varied, but the pattern held across seven conversations with people who had never met.

“They all had that commonality,” Steve says. “At some point, I have to stop generating revenue to focus on things that don’t generate revenue.”

That informal research exercise, conducted with his two co-founders to help them understand what sales really feels like from the inside, became the organizing principle behind zig.ai. The company’s premise is straightforward: identify every step in the sales process where a human is doing something a machine could handle, then build the infrastructure to handle it.

Meet Steve, Founder of zig.ai

He grew up in Boyle Heights, a working-class neighborhood in East Los Angeles where he lived with his great-grandmother in the Estrada Courts housing projects. Raised by parents he describes as young and blue collar. What they gave him wasn’t a pep talk. It was something more durable.

“It wasn’t in an encouraging way like in the movies,” he says. “It was more like, go try it, figure it out. If you screw it up, it’s on you. Take accountability and move on.”

He left college after one semester, decided he wanted a career in sales, and called everyone he knew to find a way in. An organization took a chance on him, and he spent the next 16 years climbing through roles as a sales rep, sales engineer, and eventually the head of sales organizations. That accumulated experience, not a whiteboard hypothesis, is what zig is built on.

zig is an intelligence and execution platform for sales teams. Organizations plug in their existing data, including email threads, ongoing conversations, and CRM records, and zig assembles what Steve calls a “compounding context layer.” Think of it as a shared memory bank that every workflow, every AI agent, and every automated process inside the platform draws from. It learns what has worked historically, adjusts based on new behavior, and uses that evolving picture to make better decisions over time.

The goal is to give salespeople back the hours they currently spend doing things that feel like work but don’t move deals forward.

The Problem Generalists Kept Missing

Steve raised zig’s initial funding from Superset, a venture firm made up entirely of former founders. Getting there required convincing investors who hadn’t spent careers in sales that the problem was real and worth solving.

That turned out to be harder than he expected.

“Explaining sales to non-sales folks is very difficult,” he says. When talking to investors who came from product and engineering backgrounds, he found that some saw sales as a profession where likability and product strength were the primary variables. The operational weight, the quota clocks, the cognitive load of managing a funnel across multiple disconnected tools, didn’t register as structural problems worth solving. They registered as noise.

His advice to founders who hit the same wall is direct. “If you spend your time wondering why a VC said no and why they don’t see your vision,” he says, “you’re going to drive yourself crazy.” The better use of energy is to find the investor who already understands the vertical deeply enough to recognize what the founder is describing. For Steve, that was Superset.

One thing that made the Superset relationship work: all the general partners have built companies themselves. That background, Steve says, produces a different kind of engagement. When he is working through a decision, he walks across the shared office, pulls a GP into a quick conversation, and uses the exchange to organize his thinking. They don’t decide for him. They ask the questions that help him decide faster.

“It speeds up the decision making process,” he says, “much faster than them not being there.”

For early founders trying to evaluate investors, Steve offers a practical filter: find out whether the people writing the check have built something from zero to one before. The intangible value of that experience, he says, becomes clear in the first 30 to 60 days of building.

The Longer View on Sales and AI

Steve has a clear perspective on where AI agents fit inside a sales organization, and where they don’t. The rapid rise of AI sales development representatives, or AI SDRs, producing high-volume cold outreach has already started to desensitize buyers to cold email. When every company targeting the same prospect is sending automated sequences, the volume stops being an advantage. Messaging quality becomes the only differentiator, and most AI SDR tools, Steve argues, operate with too little context to improve their messaging over time.

zig’s outbound functionality takes a different approach. Rather than maximizing volume, it layers context onto outreach, adjusting tone, content, and timing based on industry, team size, and the profile of deals that have closed before. The bet is that precise, well-informed outreach will outperform broad, generic outreach as buyers get better at ignoring the latter.

As for the longer-term question of whether AI replaces salespeople entirely, Steve draws a comparison to what has happened in software engineering. AI has given strong engineers the ability to produce significantly more output without additional effort. He expects the same pattern to play out in sales: the best performers get a meaningful productivity lift, while the gap between top and bottom performers becomes harder to ignore. AI doesn’t directly eliminate roles, in his view, but it reduces an organization’s tolerance for underperformance.

What Steve Would Tell a Founder Starting Today

zig’s thesis was not built on research reports or market surveys. It was built on 16 years inside the profession, a series of direct phone calls, and a willingness to be told no by investors until the right one said yes.

For founders navigating the same early stages, Steve closes with a framing he uses internally: if you are a non-technical founder, be able to explain the micro as clearly as the macro. If you are a technical founder, make the inverse your discipline. Build the skill in whichever direction is harder for you.

“It allows everyone around you to move fast, but with intention,” he says,“Meaning you don’t sacrifice direction for speed. Forward is all that matters.”

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Sam Gibson left a stable engineering job in Kansas City with $10,000 in his bank account and a plan to build a miniaturized nuclear power plant. Two and a half years later, his company is merging with a publicly traded entity at a $1.2 billion valuation. The story between those two facts is the one worth telling.

A Cold DM and a Calculated Leap

The first move Sam Gibson made toward building Hadron Energy was sending a direct message to a founder he had never met. He was living in Kansas City, working a steady engineering job, and describing a business idea that even his eventual mentor, podcast host Kevin Jurovich, privately filed under “crazy or genius.” Kevin, a founder himself who makes a point of responding to early-stage builders, got on a phone call with Sam. Then another. Then several more.

“I thought you were partly crazy,” Kevin admitted during their recent sit-down on the Founder Uncovered podcast. That was in 2023. Sam was 22 years old.

By July 2024, Sam had packed his car and driven to what he thought was the Bay Area’s promised land. He landed in East San Jose, a neighborhood Kevin described diplomatically as “the opposite of quintessential San Francisco,” and signed an Airbnb lease that doubled as his founding office. He officially incorporated Hadron Energy there, with roughly $10,000 to his name and no investors yet on the cap table. The first check he received was $2,000. He took it.

What Hadron Actually Builds

Hadron Energy is developing what Sam calls Lightwater Micromodular Reactors, a compact nuclear power system that produces 10 megawatts of electric output, enough to power 10,000 homes simultaneously. The company is targeting data centers, critical infrastructure, and remote communities as its first customers, positioning clean nuclear energy as the most direct answer to what Sam describes as the defining constraint of the AI era.

“Power is the limiting factor for AI,” Sam said. “When you’re talking to hyperscalers and data centers, that’s the most important thing.”

The company’s engineering headquarters remains in the Bay Area, where Sam draws from a hiring pipeline anchored at Berkeley and other regional universities. Sam himself now lives in New York City, where he leads the capital markets work for the company’s pending NASDAQ listing.

To date, Hadron has raised just over $8 million across pre-seed, seed, and a small Series A. The company is currently merging with GigCapital7, a Special Purpose Acquisition Company (SPAC) with $212 million in trust. Bankers have valued Hadron at $1.2 billion. Sam expects net proceeds of approximately $200 million after what he anticipates will be a low redemption rate, plus an additional private investment in public equity (PIPE) raise he is actively leading.

The Builder Behind the Company

Sam’s background is in mechanical engineering and engineering leadership, which explains both how he got here and how he thinks. He does not describe himself as someone who woke up one morning with a billion-dollar idea. He describes himself as someone who always knew he would start a company and spent years building toward the moment when it made sense to stop preparing and simply move.

“There always comes a day when you have to stop studying and just make the jump,” Sam said. “There’s always the analysis paralysis where you get stuck in a loop of doing constant research. There’s something to be said about trusting your instincts.”

At 24, Sam leads a team that includes engineers and professionals significantly older than he is. He addresses the age dynamic with a straightforwardness that reflects how he approaches most things. “If you surround yourself with the right people, age doesn’t matter,” he said. “There shouldn’t be an age requirement for success. I don’t subscribe to that mentality.”

His personal routine reflects someone who treats operational consistency as a professional edge. He goes to bed early, wakes up early, and keeps regular dinner hours. He called himself “an old soul” with a laugh, but the point underneath the joke is a genuine one: he structures his days to protect his capacity to work.

Two books he returns to are Robert Greene’s “The Laws of Human Nature,” which he recommends for any founder navigating investor and team relationships, and “Meditations” by Marcus Aurelius, which he credits with shaping his long-term mindset. “If you have the right mindset, you can do basically anything,” he said.

How Survival Became Scale

The hardest stretch of the Hadron story is not the merger or the regulatory meetings in Washington. It is the months between Sam’s first $2,000 check and the point when checks started arriving fast enough to keep the company alive.

“I started the company when I had like $10,000 in my bank account,” Sam said. “Many months later, I had $20,000 and I’m like, I’m going to be patient. We’re going to keep pushing. There were many times where I felt if I don’t receive this investor check, this is going to put me in a really hard spot.”

He does not frame those months as a crisis he survived. He frames them as the natural cost of operating at the idea stage in a capital-intensive industry during a difficult fundraising environment. What kept him moving was a belief that persistence in the right direction compounds over time. The first round target was $500,000. It took longer than he expected, but he closed it through friends, family, and former colleagues. Then the checks grew. A $100,000 investment. Then $200,000. Then several at $500,000. Then the first million-dollar check arrived.

“It’s a lot of work and legwork to get from the early day angel checks to the more institutional, sophisticated investors,” Sam said. “Those are the folks we’re talking to now.”

The regulatory side presents its own sustained challenge. Nuclear energy requires ongoing engagement with the Nuclear Regulatory Commission, the Department of Energy, and other federal bodies. Sam travels to Washington frequently, describing the process as one that rewards consistency and direct contact. “It’s about showing up and having boots on the ground, face to face interaction,” he said. “That is really what drives the ball forward.”

He described the diligence process behind the SPAC merger as something he will never forget, and not because of the valuation number. “I cannot believe how much diligence went into that merger and going through the process,” he said. “It was obviously very exciting.”

What the Next Chapter Looks Like

Sam’s goals for 2026 center on completing the NASDAQ listing, scaling the engineering team, and making measurable progress on the licensing work that will eventually allow Hadron’s reactors to connect to the grid. He also wants to build the brand into something recognizable beyond the capital markets audience currently paying attention.

“I really want to make Hadron a name brand so that when people think of clean energy, they think Hadron,” he said. “A nuclear reactor is pretty complex, but what we’re doing is trying to make it as simple as we possibly can for the average person to understand.”

The mission framing is consistent and specific. Sam has repeated throughout this journey that the valuation and the capital story are tools, not the destination. Putting reactors on the grid is the destination. Everything else is infrastructure toward that goal.

When Kevin asked Sam what personal quality he credits most for how far Hadron has come in under three years, Sam did not hesitate. “I am very stubborn and very persistent,” he said. “If you truly believe this is the right way, you stick to your guns. Naturally, people will follow that the longer you do it. I know for a fact where I’m going. It’s a matter of if this person wants to join.”

That is not the language of someone chasing a valuation. That is the language of someone who once sent a cold DM from Kansas City with a nuclear energy idea and a very clear sense of what came next.

This season is supported by Perkins Coie. Perkins Coie is a leading international law firm known for providing high-value, strategic solutions. The Emerging Companies and Venture Capital team counsels startups and the investors who back them, supporting clients from formation to exit. In the past three years, clients have raised more than $23 billion in private markets between the pre-seed and growth stages. Perkins Coie combines tailored counsel with sector experience, so when it’s time to accelerate, whether for the next financing round, a strategic deal, or going public, your team is ready. To learn more, visit perkinscoie.com

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Back in 2019, I used to walk around SoMa in San Francisco listening to founder podcasts, trying to figure out if what I was feeling was failure…or just the process.

How I Built This, Masters of Scale, then later Lenny’s Podcast and My First Million.

That was my founder education.

I was obsessed with learning from people who came before me.

Because when you’re in the desert as a founder...trying everything, hitting dead end after dead end, it helps to hear that the people you admire went through the exact same thing.

Behind every “overnight success” are years of doubt, false starts, and almost quitting.

That’s why I’m excited to announce the launch of Founders Uncovered.

I’ve teamed up with Drew Glover and Nick Madrid at Uncovered Media to host a podcast focused on the real stories behind building companies...the good, the bad, and the uncomfortable parts we usually skip.

There are so many incredible founders out there quietly changing the world. Their stories deserve to be told.

Season 1 drops next month. Our hope is that you walk away feeling educated, inspired, and a little more optimistic that you can get it done too.

One conversation can change everything.

Can’t wait to see more founders win. 🚀

-Kevin

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