The Last Mile

Before describing where we are today, it is important to provide some color on what it took to get here. There have been tons of mistakes, bumps, and ugliness along the way. Most of it was failing forward.

When my partners and I took over Wiss in 2011, the firm was in rough shape. There was in-fighting, factions, a culture that had been badly damaged by a leader who put himself above the firm. We were merging firms in, de-merging firms out, still reeling from the 2008 crisis, and fighting with an insurance company because someone’s ego had gotten in the way of filing a legal claim on time.

The first few years weren’t about building anything. They were about repair. Restoring trust. Getting back to the foundational layer that made Wiss special before someone spent a decade dismantling it. That work isn’t glamorous and you don’t get to talk about it in press releases, but it mattered. Everything we’ve built since then sits on top of it.

By 2016, we finally felt like we had the culture we wanted to build upon. And that’s when I felt ready to attack this question I’ve been obsessing over since I began my career. How can we make accounting feel like a more exciting profession?

The First Attempt

We launched something called WEST in 2016. Wiss Early Stage Technology. The name was a little ambitious, but so were we.

The idea was to bring real accounting and advisory to pre-seed, seed, and early-stage companies at a price they could actually afford. A few hundred dollars a month. Matt Barbieri led the charge. We got a ton of clients fast, which felt great until it didn’t. The math never worked, and there were two reasons for that. First, investors had flooded the outsourced accounting space with capital, funding companies like Bench and driving pricing down aggressively. Second, accounting is nuanced. The existing tools in the market couldn’t create capacity. The only way to scale was to add more people, and the margins made that impossible. Clients felt like they weren’t getting enough. We felt like we were giving too much away. Nobody was happy.

To try to solve the scaling problem, we built software on top of it. An alert system that could tell a founder when their cash dropped below a certain threshold, when a check was written outside of normal parameters, when something was off before it became a real problem. Insight, not just reporting. We were genuinely excited about it.

But the labor component never went away. The market wasn’t ready. We took our lumps and brought the business back into Wiss to create a better version. We were determined to fix it. Little did we know we were planting the seed for what would eventually become our AI technology “lab”.

I think about that period a lot. Not with regret, exactly. More like the feeling after a loss you could have prevented. We saw something real. We weren’t wrong about the problem, we were just wrong about the timing and what the technology could actually solve at that point.

But we didn’t stop.

What I Learned Losing a Soccer Game

Sports have always been my thing. Soccer especially. So when the opportunity came up to help coach varsity soccer at Hanover Park High School while working at Wiss, I jumped at it. I loved every minute of it, and there is one game that I still think about in particular.

Once in a while, a team has that one player who just isn’t fair. Ours was Jake Edwards. Kid went on to play professionally in England, eventually became President of the USL, and now runs Huddersfield Town FC. My son plays FIFA and is always complaining that certain players are so overpowered they ruin the game. Jake was that guy. Except it was real life and he was on our team, so it was great haha.

We were playing Chatham late in the season in a nail biter that was winding down to the last few minutes. Their gameplan was pretty simple and they ran it the whole game. Swarm Jake every time he touched the ball, double teams, shadow marking, the whole thing. He couldn’t do anything with it. I saw it happening in real time and kept telling my guys to find Jake anyway. Same instruction, every possession, even as it stopped working right in front of me. I couldn’t bring myself to change the plan. Whether that was pride, stubbornness, or a combination of the two, we gave up the lead with less than a minute left, lost in overtime, and Chatham went on to win the entire state tournament that year.

I hate losing. What makes it worse is when you know the other team didn't outclass you… they just found a crack and walked through it. That kind of loss sits differently.

I knew what was happening and did nothing about it. That has stuck with me for a long time. The older I get the more I believe that the best leaders are the ones who can look at a situation honestly, admit when something isn’t working, and trust the people around them enough to change course without it feeling like a crisis. That’s harder than it sounds when you’re standing on a sideline with a lead and a plan you’ve been running all season. But that’s the job. Read it, adjust, trust your guys, and move. I’ve tried to bring that into everything I do at Wiss ever since.

A Random Meeting

In 2022, one of our colleagues, Mike Castle, got a LinkedIn message from a Babson College alumni connection. Two guys wanted to come in and talk about what they were building. I didn’t know what to expect. I have been in enough of these meetings to know most of them go nowhere.

But these guys were different in a way that was hard to put my finger on at first. They weren’t selling a product. They were trying to solve a problem that had been bothering them the same way it had been bothering us for years. Big dreamers swinging at something genuinely hard in an industry most people ignore. That resonated with me. We had done the same thing with WEST and taken our bruises for it, so I knew exactly what that kind of ambition felt like and what it cost.

Beyond the idea, I just liked them. Good character is hard to fake in a room. You can tell pretty quickly whether you are dealing with people who are in it for the right reasons. We had good chemistry, genuine mutual respect, and a shared belief that accounting deserved better tools than what existed. I trust people before I trust products. These were good people.

We wrote one of the first checks into what is now a billion-dollar company. Not a bad bet.

The Last Mile

We had proven something with our early bet. That the right founders, working on the right problem, could actually change how accounting worked. But one great partnership wasn’t a strategy. It was a proof of concept.

The question became what we do with it.

There are hundreds of tools being built for this industry right now. AI that handles month end close, accounts payable and receivable, cash flow forecasting, expense management, revenue recognition, the list goes on. Some of it is genuinely impressive. A lot of it is noise. Most firms don’t have the time, the technical fluency, or the live environments to figure out which is which. So they either chase everything and get nowhere, or they ignore it entirely and fall behind. Both are versions of standing on that sideline watching something fail and doing nothing about it.

That is the gap we kept seeing. We had been doing this work quietly for years, dedicating real resources to evaluating tools and then actually stress testing them before they ever got near a client. After enough positive feedback we figured it was time to formalize it and give it a name. That is Wiss Labs.

Where This Actually Goes

Here is what I know after thirty years. The firms that win are not the ones with the best resources or the most prestigious names. They are the ones willing to look at a situation honestly, change course when something is not working, and bet on the right people before it is obvious to everyone else that they should.

We have been building toward this moment since 2011. The culture repair, WEST, the early bets, the failures and the adjustments. None of it was wasted. It was preparation.

What makes Wiss Labs different is not one thing, it is the combination of all of them at once. Decades of institutional accounting knowledge that every fintech startup needs but cannot replicate. AI that is finally powerful enough to do something meaningful with that knowledge.

And a firm with the DNA to actually move on it rather than study it from a distance. We have never been the kind of place that waits for permission or consensus. We try things. We adjust. We go again.

That is a hard thing to build. It took us a long time to get here. But we are here, and the timing has never been better.