Dave and Jon Willson had sold a financial-services business doing more than $2.5 million a year. Then they took some of the money and started building another business.
A software business. With financial data. Which, as Dave explained, has to be accurate every time.
So, about halfway through our conversation, I asked the question that seemed pretty reasonable to me: Why didn't you just retire?
Their answer involved a problem they couldn't solve for their own customers, a lot of time spent building something people could actually use, and a business failure that had changed their entire family's life.
Let me back up.
Jon started working for his entrepreneurial dad at 17. His younger brother Dave started a pastry business at 11. They later worked at Countrywide, then left to start their own mortgage bank heading into the mortgage crisis. Since then, they've built businesses that sold and businesses they were perfectly comfortable calling failures.
Their most recent exit was Proven CFO. Their next business is Level Up.
When we spoke on June 30, 2026, Level Up was in beta, with more than 600 companies on the platform. But to understand what they were building, I first needed them to explain what the thing actually does.
In this episode, you'll learn:
- what changes when an accounting firm needs to understand 200 businesses at once;
- how the problems inside Proven CFO became the product for Level Up;
- how the brothers get customers through relationships and referrals;
- why they took angel investment after bootstrapping earlier businesses;
- why making financial software accurate is only part of getting it ready;
- how they're using AI to make differently organized financial records comparable;
- why their father's business failure still shapes the work they choose; and
- what makes marketing awkward when your profession trains you to keep people's secrets.
What Exactly Does Level Up Do?
I like to start with a very basic question: What's your business? What's the product, and who's buying it?
Especially when the business involves financial services. My listener isn't necessarily the most informed person in the universe on that subject. Neither am I.
Jon described Level Up as financial reporting for businesses, with a particular focus on people responsible for a portfolio of them: accounting firms, venture capital firms, private equity funds, family offices, and franchisors. Banks and credit unions were also part of the longer-term picture.
The problem comes into focus when you look at what the brothers were doing at Proven CFO.
They were managing financial reporting for more than 200 businesses every month, alongside bookkeeping, payroll, sales tax, and helping owners understand the numbers.
That's a lot of businesses to understand.
And, Jon explained, the software they were using generally let them look at one company at a time. They could open an individual company's books, but seeing how the whole portfolio was doing was another problem.
Who's doing well? Who's struggling? Where does somebody need help?
Multiply that by 200, and individually opening every company's financials becomes a pretty bad way to keep track of the whole thing.
They Sold the Service Business. Now They're Building the Tool It Needed.
At first, this sounded like they had sold a company and started another company doing the same thing.
So I asked them about that.
Proven CFO was the service business. Its team did the bookkeeping, ran payroll, and produced reports. Level Up is software that brings financial information together and helps people understand it.
That distinction matters because the software grew out of problems they had already experienced doing the work.
Visibility was one. Quality was another.
Dave said they couldn't simply open a piece of software and see, quantitatively, whether the financial statements their team produced were an accurate reflection of the work. They relied on their people, customer conversations, and survey feedback.
Were the books reliable? Were the accountants doing a good job? If you were the accountant, how could you tell whether you were doing a good job?
Those were questions inside their own company before they became product questions.
Level Up is intended to combine information from the financial software those businesses already use, giving an adviser a view across the whole portfolio and the ability to zoom into an individual company.
Jon gave a useful example with franchises. A franchisor might know what each location sold. But top-line revenue doesn't tell you the whole financial picture of that location.
Their goal is to make that fuller picture visible.
And the 600-plus companies on the platform? Jon said those were primarily businesses being served by accounting firms, with others connected to investment firms, family offices, and franchisors. That number described companies on the platform, not 600 separate accounting-firm customers.
Getting Customers Starts With the Relationships They Already Have
Once I understood the product, I wanted to know how they got people to buy it.
I initially meant Level Up, but I also wanted the story from Proven CFO. How did the service business get its customers?
Relationships, Jon said.
Neither brother described marketing as his natural strength. What they were good at was doing valuable work for people and building relationships through that work.
Proven CFO got a foothold working for a family office. They helped source debt, refinance, and restructure parts of its portfolio. Over time, that expanded into accounting and putting information systems into the businesses so the family office could understand what it owned.
Then came referrals.
They were using a similar approach with Level Up: start with people and companies they already knew, demonstrate value, and let those relationships introduce them into circles where they didn't already have a direct connection.
The work they had done for years gave them both a problem to solve and people to talk to about solving it.
Angel Money, Their Own Money, and a Different Kind of Launch
I thought they had taken venture capital. Dave corrected me.
Angel investors. No VC money yet.
They expected venture capital to come later, but at the time of our conversation, the outside money had come from individual, non-institutional investors.
“They're just really nice people,” Dave said.
Hence the name.
This was unfamiliar territory for me. My businesses are bootstrapped, and so are most of my entrepreneur friends' businesses. I wanted to understand the sequence. Were they trying to prove the product worked, and then what happened next?
Dave explained that this was their first experience taking angel money too. They already knew what it felt like to put their savings into a company, leave the safety net of employment, and throw their energy into making it work.
Their Proven CFO exit gave them money they could put into Level Up. But software required substantial spending before they had a finished product to sell.
Even with AI, someone still has to spend the time to build something valuable.
And with financial information, “valuable” comes with some pretty demanding requirements.
A Product Can Have the Features and Still Be Crappy to Use
Dave kept coming back to accuracy.
The software needed to be stable and secure. It needed to be a safe place for financial data. And it needed to solve real problems with financial information people could rely on.
He described the standard they were working toward as 100% accuracy. Someone looking at their company's financial information needs to be able to trust what they're seeing.
Getting there had taken longer than launching their other businesses.
Their initial customers were accounting firms, which might serve 100, 200, or 500 different businesses. Those clients don't all operate the same way. Every one brings its own problems, and Level Up has to sit above that complexity and help make sense of it.
At the time we spoke, they had users and paying customers. They were still working through the final stretch of making the feature set, explanations, and interface ready for a broader launch.
Dave reached for the iPod and the iPhone to explain what he meant.
Think about the single scroll wheel on the iPod. Or being able to open an app on a phone and understand what to do with it.
Then think about the devices that had a lot of features and were a pain to use.
I had a Palm Pilot as a teenager. So, yes. I could follow this example.
Dave's point was that the experience of using the product matters. A long feature list doesn't help much if the person looking at it can't figure out what to do.
They were aiming for a product a trained CPA could use, but also someone fresh out of high school without an accounting background. Jon didn't want people to feel they needed a finance degree or a particular level of sophistication to get value from it.
Between them, he said, they had served more than 500 businesses over the decade before Level Up. Service companies, software businesses, product businesses, medical businesses. They'd spent years looking under the hood.
They wanted someone else to be able to connect their accounting software and get useful financial intelligence without spending those same years learning how to assemble it.
Jon also pointed out something very recognizable: entrepreneurs can end up watching one number, their bank balance, and using that to decide how the business is doing.
Their goal was to give owners more to work with when making decisions about growth.
When we recorded, Dave described a planned third-quarter public launch. That was their plan at the time of the interview.
So Why Didn't They Just Retire?
By this point, we had spent a good chunk of the conversation on how hard the new business was to build.
Which brought me back to the money they'd made selling the previous one.
Why take that money and start another really difficult business?
Jon's first answer was simple: he and Dave enjoy working together. They also enjoy complicated problems. And this particular problem had bothered them while they were running their own firm.
He saw a big opportunity in the gap between information about public companies and information about private businesses.
He was looking at a U.S. market he described as more than 30 million small businesses, and a much larger opportunity globally. He emphasized how much employment and economic activity small businesses support, while arguing that financial intelligence for them remains underserved.
Public markets have enormous amounts of data available. With private businesses, he said, the information is fragmented and hard to compare. That makes useful benchmarking difficult.
To explain the problem, he walked me through a chart of accounts.
Think of the categories in your personal budget. Income. Expenses. Rent. Gas for your car.
Businesses categorize their financial activity too, but the categories get more complicated. And one business organizes its books differently from another. Even two competitors that look similar from the outside can look very different underneath.
For individuals, you might track net worth. In a business, you're also looking at the balance sheet.
If you're trying to compare companies, those differences in organization become a real obstacle.
Jon and Dave thought AI could help them solve it. In particular, they believed large language models could help make those differently organized accounts understandable in a consistent way.
But believing that and getting it to work reliably were separate stages.
Jon described the first year-plus as scary. They were putting a lot of money into the business while figuring out the data layers and whether the model they were training could consistently do what they needed.
Then, even after they believed they had solved that problem, they still had to turn it into something simple and enjoyable for someone else to use.
The technical breakthrough didn't finish the product.
Their Dad's Business Failed. The Whole Family Had to Start Again.
Dave had another answer to my retirement question.
After 17 years in business, their dad's company in South Africa shut down. That failure was part of what brought the family to the United States to start over.
I asked whether he'd seen the fallout in his own family.
“Oh yeah,” he said.
He described the financial pressure, the emotional turmoil, and the changes a failure can bring into family relationships. He also described the economic conditions and crime in South Africa as part of their family's decision to leave.
They came to the United States hoping to build something. And they did. But that earlier failure stayed with them.
It also helped explain why they kept choosing accounting.
Dave said their popcorn business had been the most fun. They had run an accounting firm at the same time, and accounting wasn't the fun part.
It was necessary, though. People need reliable financial information to make decisions.
Dave talked about how many businesses fail, reaching for rough statistics while acknowledging the numbers weren't quite right. His question was about the response to that failure.
If a huge percentage of students were failing at school, he said, we'd start asking what was wrong with the system. With businesses, the blame often lands on the owner.
He acknowledged that owners have things to learn. But he also believed the systems around them weren't giving them what they needed. He pointed to financial decision-making as a contributor to failure, referring to material from the Small Business Administration.
That's the work they wanted their talents to go toward: helping people make better decisions before a business failure becomes a family crisis.
“We don't want other people to fail.”
That was Dave's explanation for why they kept building.
Surviving Is One Problem. Being Able to Sell Is Another.
Jon added another concern: what happens when an owner has kept a business going for years and wants to get out?
A successful business doesn't automatically produce a successful exit.
He talked about owners struggling to find a buyer and turn all those years of work into a payout. He cited a one-in-six figure for listed businesses selling; that was his estimate in the conversation, not a verified rate established for this article.
Level Up's starting point was financial reporting: help the owner and the advisers around the business understand what's happening.
Accounting firms, franchisors, and other advisers could use that visibility to help owners make better decisions and be more accountable for the businesses they were responsible for.
The brothers' larger vision included the challenges around business exits. But the thing they were building first was that clearer financial picture.
Marketing Is Awkward When You're Trained to Keep Secrets
Near the end, I asked where people could follow them.
Dave said they'd been hiding in a cave building software and nobody was following him.
I pointed out that he had around 3,000 LinkedIn followers.
Yes, he said. And he told them nothing.
That took us down another trail.
I had worked as a marketer for a financial-services company, and I'd noticed how different the expectations could be. Earlier, Dave had been explaining that financial data needed to be accurate every time. In marketing, I said, you were trying to get attention while telling the truth.
Jon added another reason: people in financial services are trained to be fiduciaries.
They learn people's secrets. And they're responsible for keeping them.
So, when you ask that person to become more public, there's another set of questions running in the background. What can I share? What can't I share? What's appropriate?
That helps explain why “just post more” can be a pretty incomplete answer.
They planned to become more public as Level Up became generally available. For listeners who wanted better financial reporting, they pointed to Level Up and invited people to connect with them on LinkedIn.
What I Took From the Conversation
- Look closely at the problems inside the business you already run. Proven CFO gave the brothers firsthand experience with the visibility, consistency, and quality questions Level Up is trying to solve.
- Useful work can open the next relationship. Their family-office work led to referrals, and their existing network gave them a starting point for the software business.
- A different business model can require a different way of funding and building. Software put more cost and development time ahead of a broader launch.
- The interface is part of the work. They were trying to make complicated financial information usable by people without years of accounting training.
- Getting the technology to work is a milestone. It still has to become a product people can understand, trust, and use.
- The reason someone keeps building can come from a failure. Dave connected their work directly to what happened when their father's business shut down.
- Understanding the numbers matters across the life of a business. That includes the owner trying to grow and the owner hoping to sell.
- Understand what makes someone reluctant to market. For financial professionals, confidentiality can be part of the hesitation.
I asked them why they didn't retire, and both answers were sitting inside the work itself. They liked tackling the problem together. And they knew what was at stake when a business stopped working.
For someone trying to understand their own company, Jon's question is a useful place to start: How do you make good decisions about growth if you don't know how the business is doing financially?
Watch the Interview and Find Level Up
Watch the full conversation with Dave and Jon Willson on YouTube.
The website they shared during the interview was levelup.ai. Jon's LinkedIn profile also identifies him with Levelup.
Interview recorded June 30, 2026. Customer counts, funding, product stage, and launch plans reflect that conversation.
A note on the statistics
Dave explicitly qualified the business-failure percentages he recalled. They are not used here as verified rates. For comparison, a Bureau of Labor Statistics review reports five-year establishment survival rates of roughly 50% to 57% for selected starting years. Establishments are not the same measure as all firms. Jon's listed-business sale estimate and the broader small-business economic claims were also not independently established here.
Read the complete episode transcript26-minute timestamped transcript
Computer-generated transcript supplied with the interview. Page breaks and line wrapping have been cleaned up; the wording may contain transcription errors. The recording ends at 26:31.
00:00:04
Timmy Bauer: Today on the podcast, I have an entrepreneurial duo, Dave Wilson and John Wilson. John started his first entrepreneurial thing or did his first entrepreneurial thing at age 17 when he started working for his entrepreneur dad. Dave, his younger brother, started his first pastry business at age 11. Together they started working for the largest mortgage lender in the US called Countrywide and they left to found their own mortgage bank going right into the mortgage crisis. Several businesses together later, most recently they have built and sold a financial services and CFO advisory firm called Proven CFO that was doing over two and a half million in annual revenue. And now together they are building another business together called Level Up. And that's what we're going to be talking about today. Dave and John, thank you so much for being a guest on my show.
Dave Willson: Yeah.
Jon Willson: Thanks for having us.
Dave Willson: Awesome.
Timmy Bauer: Did I get any of the details on that intro wrong?
Jon Willson: No, you did a fantastic
Dave Willson: Ter,
Jon Willson: job.
00:01:09
Timmy Bauer: Awesome. Awesome. The question that I always like to ask is right out of the gate, what exactly is your business?
Dave Willson: terrific.
Timmy Bauer: So, we're talking about level up here. What exactly is your business? as in what's the product and who are you selling to?
Jon Willson: How deep do you want us to
Timmy Bauer: Well,
Jon Willson: go?
Timmy Bauer: um my listener is not going to be necessarily the most informed person in the universe when it comes to financial
Jon Willson: Yeah. So, we we're building financial reporting for every business.
Timmy Bauer: services.
Jon Willson: Um, what's making us unique is we're standardizing the financials. uh for uh the accounting um but we're also geared up uh primarily to serve portfolio uh port portfolio managers. So examples would be accounting firms, VCs, uh private equity, family office, franchiseors and then eventually financial institutions like banks,
Timmy Bauer: Yeah.
Jon Willson: credit unions that are servicing business portfolios.
Timmy Bauer: Yeah. Okay. And you said before I hit record, you said you're in beta right now and then you gave me a number of people that are users, I think.
00:02:14
Timmy Bauer: What is that? What exactly does that mean?
Jon Willson: So we've got over 600 companies on our platform currently. Um these are primarily businesses being serviced by accounting firms. Some of them are uh BC, private equity, family office, some franchise or So, um, we've been testing,
Timmy Bauer: Mhm.
Jon Willson: um, a lot of features that are kind of unique to portfolio management. And the reason why we're tackling that is because of the company proven CFO that we sold. You know, we were we were managing over 200 businesses every single month in terms of doing their financial reporting and payroll, sales tax, um, helping them understand what their financials look like. Um the biggest challenge that we had running proven CFO was that um we were actually blind to a lot of how the portfolio was doing. The way that a lot of accounting software is structured, it's structured so that you can view one company at a time. So um when you have 200 companies,
Timmy Bauer: Okay.
Jon Willson: it's just not humanly possible to go and look at how all 200 companies are doing all at the same time.
00:03:23
Jon Willson: So that that's what we've been building since our exit at Proven CFO.
Timmy Bauer: Mhm. Okay. Um, to someone who's listening who's not like in financial services, they probably heard that intro and they were like, "It sounds like you sold a company and then built another company just like it." I'm sure that's not true.
Dave Willson: uh a better analogy is we built we built one company
Timmy Bauer: What
Dave Willson: did quite well but in that company there's problems that we just couldn't solve with available technology. There was nothing in the marketplace that we could go and find that would help us solve a bunch of problems. One of those problems is visibility. Managing 200 companies all at once, seeing who's doing great, who's not doing great. The other thing that we just couldn't do is we couldn't tell if we were doing a good job quantitatively. We we couldn't tell uh like did we provide the financial statements that are an accurate reflection of the work. We we had to rely on our people.
00:04:19
Dave Willson: We couldn't just go into a software and say did we do a good job. It was like hey guys did we do a a good job talk to the customer hey are we doing a good job trying to get survey data. Um so the problems that we were experiencing within that company is something that we are now solving. So after after exiting the company with here's a bunch of problems we're doing just fine. the company that we're building is solving the problems for that company that we sold plus thousands of other companies. Anyone that ends up dealing with looking at financials for a single company or multiple companies ends up with these problems like are my are my books reliable? Are my accountants doing a good job? Am I as accountant doing a good job? Uh so that's what we're building right
Jon Willson: Yeah. And and to your listeners,
Dave Willson: now.
Jon Willson: um, Proven CFO was a service company.
Timmy Bauer: Okay.
Jon Willson: So, we were doing the actual service component of the bookkeeping, running the payroll, uh, creating the reports, etc. Level Up is strictly a SAS business.
00:05:22
Jon Willson: So,
Timmy Bauer: Mhm.
Jon Willson: it's it's an aggregator of all the different types of financial softwares out there that we had access to as an accounting firm, but it wasn't aggregated for us. We didn't have it in one place. So uh what we're building at level up is going to allow an accounting firm to have a global view on
Timmy Bauer: Mhm.
Jon Willson: how every single company is doing with the ability to zoom in at the company level to see how each individual company's doing. So it's both a very high level tool so you can globally see everything but also zoom in individually to each company to see how each company is actually
Timmy Bauer: Yeah.
Jon Willson: performing.
Timmy Bauer: And you said that avatar for Level Up is an accounting company that's managing multiple
Jon Willson: That would be one. It could be a VC that's invested in lots of uh portfolio companies.
Timmy Bauer: companies.
Jon Willson: It could be a private equity fund or a family office that owns lots of different companies. It doesn't have visibility across everything that they own.
00:06:17
Jon Willson: Could also be a franchiseor that has franchises. And if a franchiseor wants to see how every single franchisee is performing financially holistically, a lot of franchiseors just look at topline revenue in a company like what did this crumble location sell top line. They don't necessarily know the rest of the financial picture. Level up will actually produce the entire financial picture for a franchiseor as
Timmy Bauer: Nice. Um,
Jon Willson: well.
Timmy Bauer: talk to me about um what it takes and maybe this is too early based on where you're at in the business, but what it takes to for you to get clients.
Jon Willson: Depends on the business, right? Um, which business do you want to talk
Timmy Bauer: Well,
Jon Willson: about?
Timmy Bauer: we could talk about proven CFO or we could talk about level up. I was specifically thinking of level up when I asked the question, but I'm curious. I'm curious how you did it with your service business
Jon Willson: Um,
Timmy Bauer: also.
Jon Willson: you know, what's worked really well for Dave and I is relationships.
00:07:15
Jon Willson: Um, neither of us has what I would call a uh pensions or a really strong leaning towards marketing. Um, what we're very good at is building uh relationships produced by producing high value services. So for proven CFO, we um we actually got our foothill hold by working for a family office. Um producing all kinds of financial services for that family office,
Timmy Bauer: Mhm.
Jon Willson: sourcing debts, helping refinance, restructure some of their portfolio. Um eventually we actually started getting involved in the actual accounting putting information systems into the businesses trying to create that holistic view for the for the uh family office so they can understand how the companies were performing. Then from that we ended up getting a lot of referrals. Uh level up is functioning I would say the same way. Although it's a SAS business, uh we're using our existing network. Um trying to demonstrate value for the individuals, companies that we already know. And then as we as we do that,
Timmy Bauer: Mhm.
Jon Willson: we're we're getting introduced into a lot of other circles that we don't necessarily have firstderee contacts
00:08:31
Timmy Bauer: Yeah.
Jon Willson: into.
Timmy Bauer: And you said this one is a mixture of bootst like you're you had four businesses that were bootstrapped to to sold and this business you've taken BC funding. Yeah.
Dave Willson: Not not VC funding yet, but we have angel investors.
Timmy Bauer: I see.
Dave Willson: So So we will take VC funding later,
Timmy Bauer: Okay.
Dave Willson: but right now we've the money that we've collected is from angels, which are which are non-institutional investors.
Timmy Bauer: Gotcha.
Dave Willson: They're just really nice people.
Timmy Bauer: Hence the name. Um, what's the what does the the So, this is so far outside my my world.
Dave Willson: Yes.
Timmy Bauer: So, my businesses are all bootstrapped. Um, and I told you about mine before we hit record. And most of my friends that are entrepreneurs bootstrapped their business. Um, I I'm trying to think if I have any friends that built their business through investors. I have a couple, but I don't I I haven't dug into their story so much. What's the growth plan look like for you?
00:09:25
Timmy Bauer: Like, how like how does it work exactly? Right now, you're just trying to prove that the product is really good at what you say it's good at. Is that is that where you're at right now? And then what comes
Jon Willson: You want to tackle that, Dave?
Dave Willson: Yeah. So,
Timmy Bauer: next?
Dave Willson: you know,
Jon Willson: Yeah.
Dave Willson: this is also our first venture into taking a angel money or eventually venture money as well. So, so we know what it's like a lot by starting a business, putting your savings and your heart onto the line, not having employment to ensure that you've got a safety net, and then just pouring all your energy and attention into launching a business just right out of the gate. Um, because of our exit at Proven, we were able to have some funds and to be able to put funds into the launch of Level Up. Because it's software, it's very capital intensive on the front end. uh in order to to build something even with AI in order to go build a good product you have to spend a lot of time ensuring that you created something of value and in the in the world of accountants and VCs and franchises especially around financial data we've really needed to make sure that our product was not only stable and secure and all of the the criteria around making sure that it's a safe place for financial data it also has to be something that provides immense value
00:10:47
Dave Willson: as well as being like 100% accurate all the time. Not not a lot of softwares that exist, SAS softwares don't have those same strict requirements around them.
Timmy Bauer: Mhm.
Dave Willson: This this financial data needs to be you know nailed down 100% perfect. Nothing can be wrong. So the way that we've gone about launching this business has been very timeconuming. We've spent lot a lot more time launching the business than we have any other of our business. So where we're at right now is we're we're at the tail end of making sure that the product and the feature set is robust enough to satisfy a lot of the problems and solving problems that accounting firms you primarily that's our our ICP right it's our initial customer profile the the people that we target first they have a host of problems because they're trying to solve other people's problems uh an accounting firm might have 100 200 or 500 clients and those 500 clients are completely disparits. None of them are the same. So everything that they're tackling, each client of theirs presents its own unique problem.
00:11:51
Dave Willson: And our solution needs to be able to sit on top of that whole mess and help them fix that mess. So where we're at right now is we've got a robust enough product that we've got users, we've got paying customers. Uh we're not ready to go and like wave our flag around and say, "Hey, we're ready for the whole entire market because there's uh in the US, you know, millions of small businesses. there's you 80 plus thousand accounting firms. Uh they service those small businesses. Uh and that's where that's where we're at. We're at the tail end of that. Just making sure that the the new accounting firms that we're bringing on are sufficiently happy with all the feature sets, that it's uh articulated well, that the user interface makes a lot of sense to them, that we're getting rid of complexity. Uh think Steve Jobs, right? The first iPod, single scroll wheel and a button. um the iPhone just a a blank screen blank canvas with a bunch of little icons that that tail end of the products product might be good right like a Zoom I don't if you remember Zoom and like the the early the the Palm Pilots and stuff they
00:12:58
Timmy Bauer: Oh, I had one as a teenager.
Dave Willson: were but but they were kind of crap right which is which the the the the
Timmy Bauer: Yes.
Dave Willson: feature set was robust but it was crap to use and which is why the iPhone did so
Timmy Bauer: Yeah.
Dave Willson: incredibly well is because it had all the same feature sets as everyone else, but it was what it was streamlined and smooth and beautiful and easy to interact with. And so that's where we're at in in our our building process. Um, and when we say like we're we're in third quarter, we're ready to publicly launch,
Timmy Bauer: Yeah.
Dave Willson: it means that we feel sufficiently good enough about our products in all of those aspects like problem solving and security, but also that it's it's a beautiful thing to interact with because financial data is complicated.
Timmy Bauer: Yeah.
Dave Willson: Most people don't get it, right? Most people don't play with financial data. So, we wanted it to be simple enough for any user to come in and interact with regardless of their training.
00:13:48
Dave Willson: CPA trained or I'm fresh out of high school and I don't know anything about
Jon Willson: That's really That's really the key. We, you know,
Dave Willson: anything.
Timmy Bauer: Yeah.
Jon Willson: we don't want somebody necessarily needing a financial degree or an accounting degree or um or to feel that they need certain level of sophistication to use level up. So, we're taking a very complicated complex thing that has taken us taken us a long time to learn because we've been in the trenches providing the services to hundreds of businesses. You know, over the last 10 years prior to founding Level Up, we Dave and I have serviced over 500 businesses. So, we've looked under the cover, under the hood, so to speak, of every kind of business you can imagine from all kinds of different industries. Seen how they're put together financially, see what kind of struggles they have, whether they're a service business, a SAS, a product based business, medical, whatever. Um, and identifying, you know, what what works well and what doesn't work well from a financial accounting standpoint.
00:14:46
Jon Willson: So, what we're hoping to bring to the market is something that just a it's a simple plug and play. It's kind of like the like Dave was saying the the iPhone. Click the app, connect your accounting to level up, and then you get all of this financial intelligence that would take a normal human being just an infinite amount of time to try and aggregate it and understand it. And it's just presented there with absolute with with absolute clarity.
Timmy Bauer: I love
Jon Willson: So, you can make good decisions.
Timmy Bauer: it.
Jon Willson: You know, how can you make a decisions growing a business if you don't know financially how you're doing? It's really difficult. And a lot of entrepreneurs end up just looking at one metric which is their bank account which is not the sole metric you should use trying to scale a
Timmy Bauer: Yeah. Yeah. That's awesome. Um, when we were talking before I hit record,
Jon Willson: That's
Timmy Bauer: I was just trying to get your timeline right of the different businesses that you've created and when and like, you know, okay, four boot four businesses that you've bootstrapped and sold, several businesses that you've left or didn't do very well.
00:15:45
Timmy Bauer: Um what earlier you were saying
Jon Willson: You can call them You can call them failures.
Dave Willson: They're failures.
Jon Willson: We're Yeah,
Dave Willson: Yeah, they sucked.
Timmy Bauer: yeah
Jon Willson: we're we're good with that.
Dave Willson: They're horrible. They were terrible.
Timmy Bauer: earlier you said something to me that made me go why why didn't why did you do this like why did you decide to do something that you said about the I guess the difficulty or something related to building level up and normally at halfway through the interview I pivot towards talking about why like your personal why the why of your business etc. My first question to you is why didn't you just retire? Like why have you not why have you decided uh I know what we'll do with with all the money that we made from our sale. Let's start another really difficult
Jon Willson: Well,
Timmy Bauer: business.
Jon Willson: I look Dave Dave and I we really enjoy working together. Number one, we do enjoy tackling complicated problems. um this was a problem for us running that service based business and there was like we we look at the the opportunity as a as a really big one because it hasn't been solved correctly.
00:16:47
Jon Willson: Um how many small businesses exist in the United States?
Timmy Bauer: I don't know why.
Jon Willson: So over 30 million you start you start to look globally and that number is is even
Timmy Bauer: Okay.
Jon Willson: bigger. More than half of the world's GDP is contributed by small business. uh most of the will is employed by small business and yet small business is often underserved in the financial services space or the financial intelligence space or where we get data. So much focus is put on the public markets. Think about how much data exists around the public market companies and yet inside of the private space it's
Dave Willson: Thank you. I'm in
Jon Willson: very disjointed.
Dave Willson: space.
Jon Willson: Uh it's opaque. You don't really know what's going on. You can't do proper benchmarking. Can't really get good data to compare how you're doing. Um and data really is power. So we thought a lot about that um as we were exiting proven CFO especially as AI was coming onto the scene.
00:17:44
Jon Willson: Um still very early days with AI but we we had this concept that we could take a disparit chart of accounts which is how companies code their books. So, if you're not familiar with what a chart of accounts is, it's it's basically, you know, think of a personal budget, income, expenses, and within income and expenses, you can do different categories of of, you know, this is my gas for my car, this is my rent, etc. Well, businesses operate the same way in accounting. It's just a lot, it becomes a lot more complicated. And then on the other side, you know, uh when you're an individual, you track your net worth while in businesses, you track your balance sheets. So, um, in the world of accounting for private business, every single business has a different chart of accounts, which is pretty natural, right? If you're growing a business, the way that you're doing your business uh is going to be very different to somebody in the same space. Even if they're a competitor of yours, you on the on the exterior, you could look very similar, but underneath the hood, you're always going to look different.
00:18:47
Jon Willson: So Dave and I looked at that and thought, we actually think we can solve that. And we think we can use AI uh to solve that problem, which would which wouldn't be possible without these LLMs. And that's what we're tackling. And we're excited about it. Like uh in the beginning I would say what do you think Dave? The first year plus it was pretty scary because we were pouring a lot of money into it and it was just taking a lot of time to actually figure out things like the data layers you know how we going to how we going to handle the data effectively. Um can the can the LLM uh that we train actually do what we needed to do consistently well? And we eventually got to that point where we knew that we had solved it,
Dave Willson: Another
Jon Willson: but then we still had so much building to do to actually make it a product that would be simple and delightful and easy to use for the
Dave Willson: reason I would say why,
00:19:40
Jon Willson: user.
Dave Willson: you know, why do we keep going is is cuz after 17 years of successfully running a business, my dad's business shut down uh in South Africa. It's it's the reason why we're here in the United States. It's also the driving factor around the why of the businesses. Why did we do accounting service related business? The popcorn business that we had was the most fun. But while we were running that, we were still running an accounting firm. Um, accounting is not fun, but accounting is necessary. It's it's almost critical to ensuring that somebody is making good financial decisions. Uh, there's there's a statistic. It's not quite right, but I'm going to give you the generalized statistic. It's 80% of small businesses fail within the first 5 years and of the remaining 20% another 80% of those 20 will fail over the next 5 years from that. So the the am the the amount of small businesses that fail is very high and the
Timmy Bauer: Shoot.
Dave Willson: the fallout from that event right if you think about a failed business and the resulting emotional turmoil that like you describe in your own business when you're hit with co not your fault but you're just crushed right you're you're crushed and things change um relationships change the dynamic within families change uh it's it's not healthy that We have so many businesses failing
00:21:06
Timmy Bauer: Did you see fallout in your own dad's
Dave Willson: and oh yeah it's it's why we're we're immigrated to
Timmy Bauer: situation?
Dave Willson: the United States is because we needed to start all over again. The economy in South Africa is terrible. Crime rates are high and we as a family made a decision to come and come to the land of opportunity to see if we could make something happen. And we we've been able to make something happen but the driving force behind that comes from a failure. uh we are driven because we don't want failure. We don't want other people to fail. We don't want other people to be recipients of hard horrible things. Uh when you look through the SBA's uh reasonings that they they publish a bunch of information SBA, the Small Business Administration, one of the things that they put out is why small businesses fail. And like the second most common thing is businesses fail because they don't have good financial decision-m processes. And so that's why we we did accounting because there's other things there there's other things
00:22:03
Timmy Bauer: Yeah.
Dave Willson: that our talents could be put towards but we want we want to help the world. Uh maybe that's a little bit of naive altruism like we can leave the world a better place than what we found it because small business failures shouldn't have that that number is insane. Okay. Like imagine in school we had 80% of students failing. We'd be like it's not the students there's something else wrong. But in small business, we're like, well, it's it's definitely the small business owners. They don't know what they're doing.
Timmy Bauer: Mhm.
Dave Willson: And that's partly true, but it's because the system itself is not providing to them what they need. So that's what we're we're so driven about trying to provide. We want to make a
Jon Willson: Yeah.
Dave Willson: difference.
Jon Willson: The other statistic to add to that is even the businesses that are successful when it comes to exits only one in six businesses that list actually sell. So not only
Timmy Bauer: We lost you,
Dave Willson: Oh,
00:23:00
Timmy Bauer: John.
Dave Willson: John, we lost you in there for a second. Am I still here?
Timmy Bauer: You're still there,
Dave Willson: Okay, you're you're back,
Timmy Bauer: Dave.
Jon Willson: I'm back.
Dave Willson: John.
Jon Willson: Uh I was just saying um sorry that I would cut out like that but I was just saying that um even the businesses that are
Timmy Bauer: All good.
Jon Willson: successful really struggle for exit liquidity and struggle to understand how to get
Timmy Bauer: Mhm.
Jon Willson: themselves uh sold so they can capitalize. So a business owner after doing all that work for all those years can actually find some type of payout at the end. Right? So we have we have a big vision for levelup but where we're going to start is we're going to start with the financial reporting piece giving visibility to the business owner and then those uh I would call them advisers you know accounting firms are advisers uh franchiseors would be an adviser but any of the advisers give them visibility into the businesses that they responsible for so they can also help them make better decisions be a little bit more accountable to them and what is currently occurring.
00:23:58
Timmy Bauer: That's awesome, guys. This has been a great uh conversation. I've really enjoyed talking to you all. I can tell you have a lot of wisdom um and a lot more wisdom to share than I've been able to dig into in this half hour. But um where could listeners go to follow you more?
Jon Willson: at the moment. Uh, check us
Dave Willson: We've been we've been hiding in a cave building software like nobody's following me right
Jon Willson: out.
Dave Willson: now.
Timmy Bauer: That's not true. I think you have um like 3,000 followers on
Jon Willson: We
Dave Willson: I do. Yeah.
Timmy Bauer: LinkedIn.
Dave Willson: And and I tell them nothing. I I I need to be telling them more.
Timmy Bauer: Let's I have found that people in financial services, they don't tend, okay, maybe this is a generalization that would get me in trouble,
Dave Willson: I
Timmy Bauer: but they don't tend to be good marketers. Um, I worked as a marketer for a little while for a financial services company and one of the reasons I found that to be true, I think part of it is just like I don't know the way the brain is wired for financial services is just it's different in a lot of ways from marketing, but um earlier you were talking about everything has to be 100% accurate every time.
00:25:05
Dave Willson: has to
Timmy Bauer: Um, yeah. And that that that is like a must in financial services.
Dave Willson: be
Timmy Bauer: And anything less than that is unacceptable. In marketing, it's like it's successful if it gets attention and it tells the truth. But yeah, that's pretty much that's pretty much what you have to aim at.
Jon Willson: The the second component for those in financial services, I think why a lot of people that are traditionally trained or came up through financial services,
Dave Willson: Okay.
Jon Willson: which is how Dave and I did it, if you look at our backgrounds, is you're also trained to be a fiduciary. And a fiduciary gets a lot of secrets and then has to keep those secrets.
Timmy Bauer: Yeah, that's
Jon Willson: So, so it's a weird line to try and walk between,
Timmy Bauer: true.
Dave Willson: Fine.
Jon Willson: you know, being a fiduciary and then also trying to learn how to market in the space when there's a lot of things that you've got to make decisions on what can I share, what can I not share,
Timmy Bauer: Yeah.
Jon Willson: right? What what's what's appropriate, what's not. Uh, but yeah, just check us out on LinkedIn. We will become more public in the coming months once once we publicly launch Level Up, once it's generally available. Um, if you are a business owner and want better financial reporting, reach out. you know,
Timmy Bauer: Awesome.
Jon Willson: levelup.ai. Um, it's just John levelup.ai or Dave at levelup.ai. And, um, yeah, thanks for having us on, Timmy. Appreciate it.
Timmy Bauer: Thank you so much for being on
Dave Willson: Hey, thanks to me.
Jon Willson: Thank you.