Level Risk Into Trust
Scott Wolfe — Advisor, former CEO @ Levelset
About this masterclass
Scott Wolfe, Levelset Founder, Acquired by Procore
Scott Wolfe is the founder and former CEO of Levelset, the leading construction payment platform in the US, acquired by Procore for approximately $500M. Scott spent over a decade in construction, building a company around a problem most people outside the industry don't even know exists: getting paid. Often, the root cause is the construction lien process and unclear lien rights. As he scaled the platform, Scott Wolfe focused on making that path to getting paid more transparent.
What This Masterclass Covers
Construction payment is broken. Money flows through layers of stakeholders, risk gets pushed down to the people who can least afford it, and the system runs on power imbalances that nobody designed on purpose but everyone accepts. Scott didn't just build software to fix a workflow. He went after the structure underneath it. In this masterclass, Scott Wolfe walks through the full arc of Levelset, from side-desk project to venture-backed platform, and shares what he learned building a mission-driven company in one of the most complex industries in the world:
- Why construction payment is a structural problem, not a software problem, and what that means for how you build product
- How Levelset started as a LegalZoom-style tool for construction lien claims, and what happened when he kept asking "why are people ending up here in the first place?"
- The three foundings of Levelset: side-desk phase, angel-funded full-time, and venture-backed scale-up
- Why the company had to be renamed twice, and how the wrong name can become "brand handcuffs" that limit your positioning
- How Levelset went from serving small contractors to managing tens of thousands of projects for enterprise clients like Ferguson
- Why New Orleans wasn't a disadvantage but a defining part of the company's identity and culture
- The deeper question that drove the entire roadmap: where are people disempowered, and why?
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Q&A
Question: Who is Scott Wolfe, and what became of Levelset?
Short answer: Scott Wolfe is the founder and former CEO of Levelset, the leading construction payment platform in the US. After spending over a decade in construction and building a company to solve the industry’s “getting paid” problem, Levelset was acquired by Procore for approximately $500M. His work focused on making lien rights and the path to payment more transparent.
Question: Why does the masterclass describe construction payment as a structural problem rather than a software problem?
Short answer: Because the core issues aren’t just inefficient workflows—they stem from how money and risk flow through many layers of stakeholders, pushing risk to those least able to bear it and creating power imbalances. These dynamics weren’t intentionally designed, but they define outcomes. As a result, fixing payment requires addressing underlying incentives, rights, and transparency (like liens and lien rights), not simply digitizing forms or steps.
Question: How did Levelset evolve from a lien tool into a scaled platform, and what are the “three foundings”?
Short answer: Levelset began as a LegalZoom-style tool for construction lien claims. By repeatedly asking “why are people ending up here in the first place?”, the company expanded to address root causes of payment friction and opacity. Its growth followed three phases—what Scott calls the “three foundings”: a side-desk project, an angel-funded full-time effort, and then a venture-backed scale-up. Over time, Levelset moved from serving small contractors to managing tens of thousands of projects for enterprise clients like Ferguson.
Question: Why did the company rename itself twice, and what are “brand handcuffs”?
Short answer: Names shape how customers perceive what you do. The wrong name can lock you into narrow positioning—what Scott calls “brand handcuffs.” Renaming was necessary to escape misalignment between the brand and the broader problem Levelset aimed to solve, enabling the company to reposition its product and market scope.
Question: What deeper question guided Levelset’s roadmap?
Short answer: The guiding question was: “Where are people disempowered, and why?” This lens kept the team focused on transparency and empowerment across the payment chain—prioritizing features and initiatives that reduce information asymmetry and clarify lien rights, rather than just adding incremental workflow tools.
Short answer: Names shape how customers perceive what you do. The wrong name can lock you into narrow positioning—what Scott calls “brand handcuffs.” Renaming was necessary to escape misalignment between the brand and the broader problem Levelset aimed to solve, enabling the company to reposition its product and market scope.
Question: What deeper question guided Levelset’s roadmap?
Short answer: The guiding question was: “Where are people disempowered, and why?” This lens kept the team focused on transparency and empowerment across the payment chain—prioritizing features and initiatives that reduce information asymmetry and clarify lien rights, rather than just adding incremental workflow tools.
Transcript
Introduction
My name is Scott Wolfe. I was the founder and CEO of a company called Levelset, which focused on the construction payment process and making sure that everybody in construction always got what they earned. Today I'm a board member, advisor, and investor in a variety of things — many times construction tech focused. A father of three, a husband, and a New Orleanian. That's me.
New Orleans as a Home Base for a Tech Company
I was born in New Orleans, and that's a big part of why I'm still here. I did some school outside of New Orleans. My wife is from Seattle — I've spent a lot of time in Seattle. I traveled a lot, spent a lot of time in San Francisco fundraising. But ultimately, I'm from here, and I started building a variety of businesses in New Orleans. That's where the Levelset seed started to grow.
It made sense for us. We had an office in Austin, which is a really good ecosystem for technology companies and is close — much closer than San Francisco. We had an office in Cairo, Egypt, where we did a lot of development work. So we had our tentacles in different places, but the heart of the company started in and grew out of New Orleans. We had a big part of our headquarters here.
It was unique. There aren't a lot of tech companies in New Orleans at all, and certainly not many construction tech companies. So we were a unique animal. That had its pros and cons. The top cities like New York and San Francisco have a lot of advantages — but they also have significant disadvantages. The competition for talent is really fierce, and the cost of living and operating is really high. In secondary cities like Nashville — and I'd maybe stretch to put New Orleans there — things are a lot more affordable. Good talent exists there, and increasingly so given how remote people can be these days. The competition for that talent is much lower. New Orleans also made us the belle of the ball when it came to all the investment capital and startup resources available locally. So it gave us a lot of advantages and made us unique. Companies that do well are often unique in many ways — and you always want to look for those things that make you unique and lean into them, rather than trying to homogenize with what you think a company is supposed to look like.
Tennessee Williams said there are only three cities in America: New York, San Francisco, and New Orleans — and everywhere else is Cleveland. Not to beat up on other cities, but there's a little truth to that. New Orleans is a very European city, very pedestrian. It has around a million people in and around it, but only about 300,000 residents in the city proper. There's always people flowing through. There's so much music. There's a genuine cuisine that belongs to this city — not a lot of places can claim that. You can go to Paris and find a New Orleans restaurant. When I went to Paris with my cousin last year, we went to a jazz club and the guy playing was a New Orleans saxophonist. New Orleans is everywhere in really interesting ways.
How I Got Into Construction — By Accident
Construction was a complete accident in my life. Sort of. My grandfather was a general contractor his whole life. My dad grew up in a general contracting business. But when I grew up, I was in the grocery business. My parents started a small grocery business and grew it over the course of my childhood into a small regional grocery and fast food and convenience store chain. I grew up stocking shelves and running a cash register and doing a variety of things you do in that kind of retail environment. I thought I was going to go into retail.
I went to college and when I graduated, I went to law school — not because I had always wanted to, but because my family had a lot of legal things that came with their growing business. They were around lawyers a lot, and I thought a legal background would be useful if I eventually went into retail.
When I graduated law school in 2005, I took the bar exam. About three or four weeks later, Hurricane Katrina hit New Orleans. That really shifted everything — including all the grocery stores and convenience stores we had, which were all flooded. All the neighborhoods were flooded. The retail business was in a very tight spot.
My dad had developed most of his store locations himself — partly because of his general contractor background. So he had a general contractor license. He took that license, pivoted quickly, and opened a restoration business. Post-Katrina, we were doing hundreds of demolition and drywall projects every month. Very high velocity. And suddenly I was in this restoration business, waiting for my bar results. I built a software product to manage the estimates, scheduling, and processes for that restoration company. I actually started trying to sell that software, but there were a thousand other things happening at once in a very chaotic environment.
When my bar results came back, I just opened a law firm — and focused it on construction, because construction was everywhere. So I suddenly had this restoration project management system I'd built, a construction law practice, and I was steeped in the world of construction payment. And that's how the story of my life became construction. It was really by accident. But interestingly, I had a lot of roots in it.
The Best Companies Come from Being Steeped in the Problem
There's an entrepreneurial through line in my life — in my parents' life, in my grandparents' life. The reason my parents got into the grocery business was opportunistic and coincidental. The reason we got into construction was opportunistic and coincidental. And the same is true of Levelset.
You see a lot of startups and incubators where people are searching for ideas, thinking about problems, trying to come up with a company to fit a problem they've identified from the outside. I've always liked it better when you're steeped in the problem. When you're in it. I can't find a way to just think of a problem and chase it. I can only get truly behind something I've experienced in some real way.
And I think that matters — because building a company is really, really hard. Building a company that fails is hard. Building a company that succeeds is hard. You have to go through a lot of trial, a lot of toil, a lot of struggle, a lot of down moments. I don't have the ability to go through all of that for something I don't know deeply or don't care about deeply.
With construction, I got into it in a very organic way. I was swimming in the problem of payment. I was in court arguing for people to get paid. I was frustrated with the challenges they had — challenges that I had, that my parents had. Those things created a true passion and a true insight into how to fix it and why it mattered.
When I hear founder stories, I like those stories much better than the ones that go: I wanted to be a startup founder, so I thought about this thing and that thing and that thing and I chose option B. Sometimes those things work out, I suppose — but they seem less important. Less fun.
Levelset: Three Foundings
Levelset really had three different founding moments. In some ways everything went really fast — we went from ten people to about 400 people and then exited, all in maybe five or six years. But if you take it all the way back, the corporation was actually founded in 2007 or 2008.
At that time, I was working with my family on property restoration post-Katrina, running a software development company on the side, and had my construction law firm. And this little Levelset thing got started on the side of my desk — and just sat there, growing little by little. My sister helped with it. My wife helped with it. My mom helped with it at times. That lasted for four or five years. It grew from zero to about $200,000 in revenue during that time. It was always doing so well and was so intriguing to me.
In 2012 — which is really the second founding — I decided to throw all my eggs in that basket. I wound down or quit everything else and raised a $500,000 angel seed round. That's when we hired our first employee. From 2012 to 2015, we rode that $500,000 in seed capital — sometimes cash flow positive, sometimes burning a little of that money — and grew to around $2 million in revenue.
That led to the third and final founding: we decided to raise a venture round. We started with just a $1.2 million venture round led by Brick & Mortar Ventures out of San Francisco. From there we started really flying. In 2016 and into 2017, we raised a $5 million round. The year after that, a $10 million round. Then, in 2019, just before Covid, we raised a $30 million Series C. And within 16 to 18 months of that, we were acquired. Those were the three periods, the three foundings of the company.
The Mission: Empower People to Always Get What They Earned
Levelset's mission was to empower people to always get what they earned. And what's interesting is that that mission was really a flame that drove our product decisions in a very material way.
The original product was inspired a lot by LegalZoom and TurboTax, which were big at the time — growing up through the mid-2000s. The problem I saw was that people in construction who deserved to be paid and had earned their money were having a tremendous amount of trouble actually getting that money. The mechanism that gave them the right to be paid — called the lien right — is an entire structure of rules, laws, and rights that every contractor, subcontractor, architect, engineer, and supplier has. Think of it like how somebody who works at McDonald's has the right to be paid. If McDonald's doesn't pay them, there are all sorts of remedies. Construction workers have similar rights, but the process to claim them is incredibly complicated.
So the very core of the Levelset product was: somebody wasn't paid, and we gave them a very simple, LegalZoom-esque way to make their claim. And then we just kept digging on the deeper question: why are these people so disempowered in the first place? Why are they getting to the point where they even need to make a claim? It was because of required notices, or lien waivers, or the pay application process, or they needed legal help, or they just didn't understand their rights. And so every answer to that question kept pulling us deeper into the product — how do we keep empowering people to do something that should be so simple, which is to get paid for the work they did or the materials they provided?
It eventually turned into a very sophisticated product. One example I like to give: a company as large as Ferguson Plumbing or Graybar Electric — these are major material suppliers. Ferguson may be sending materials to 20,000 or 30,000 projects every single month across the United States. Some are commercial, some residential, some government — big, small, every type. What our product did at an elegant level was enable a company like Ferguson to understand every tick and tie they needed to hit for every one of those projects month in and month out, and then execute on it — whether that meant sending a required notice, tracking a deadline, or managing the hundreds of lien waiver requests they received every day.
But at the small end, you might have a subcontractor who only starts two or three projects in a month. They don't have a department focused on this. They're in the field all the time. Our product was also able to lean all the way down to them and help them manage this complex process at a scale that fits their business. Serving both ends of that spectrum was something we were really proud of.
Naming the Company: From Express Lien to Levelset
We had a terrible name when we started. Actually, we renamed the company twice — and did it poorly at least once.
The original name was Express Lien. That name had some real logic to it. When you name a company, sometimes you want to say what you do. If you name your company Zillow, you need to explain what it is — it takes a lot of marketing effort. Express Lien said what we did: we help people file liens very quickly. For the three or four years we were Express Lien, it worked well enough.
But there was a very practical problem: we couldn't trademark it. You can't trademark something that just describes what it does — it has to be more distinctive.
So we had the bright idea of calling it Zlien. That was a terrible idea. We went with Zlien for three or four years. Lots of problems. It was hard to say, hard to spell, and it had the word "lien" in it — and as it turned out, nobody likes liens. Liens were part of what we were doing as a company, but everybody hates them. In some of our sales calls, people would literally say: "Oh, Z-lien, like the thing everybody hates?" We called this internally our brand handcuffs — because that's what it was. It was handcuffs. We were trying to help people not file liens, not have liens filed against them, and our company name had the word right in it.
We always knew we had to change it. Eventually we came to the renaming project. We loved the word "level" — because one of the core problems with construction payment is how unlevel everything is. Different stakeholders have very different incentives and very different amounts of leverage. There's a big power imbalance. And that power imbalance results in risk being transferred, and people using leverage against one another in ways that compound throughout the industry.
So we came up with Levelset — which was a direct promise to the industry: we want to level the power imbalances in construction and empower people to get what they earned. When we made that change, it made a difference on so many levels: in fundraising, in explaining the product to the market, in being more accessible to a wider set of stakeholders, and in helping the team understand what they were actually doing every day. It rang a lot of bells. Even today I use the phrase "level set" when talking to other founders to explain what I built. It was that good of a name.
The Broader Construction Tech Landscape: Beyond General Contractors
One thing that has always somewhat frustrated me about the construction technology space is this: general contractors have kind of owned the construction technology story for the past 15 to 20 years. I don't think that's because they inevitably should own it, or that they're the only big market. It just happened that way — Procore took off, Autodesk followed, because the business model around general contractors made good economic sense. So we ended up with a construction tech space that is predominantly a general contractor tools category, with the idea that those tools would pull subcontractors in to use them too. I don't think we've seen that play out very well.
There is a massive market under the surface — all types of stakeholders: architects and engineers, attorneys, subcontractors and all the trades, suppliers, equipment providers. And here's the thing: most of those other stakeholders aren't even what you'd typically call "commercial construction." So if you get specific about what has happened in construction technology over the past 10 to 20 years, it's been very commercial construction heavy, built around general contractor business models.
I think that's going to diversify. The general contractor / commercial construction train has had its day and its run. There's a lot of opportunity across all the other stakeholders and all the other types of construction. And if that opportunity is well executed on, it has the potential to create better outcomes — because it will start to tie in more people and create true network effects. Not network effects that are asserted by general contractors pushing subcontractors into a platform, but genuine network effects where the benefit of one person being on the platform creates a pull for others to join. That compounds.
I think as construction technology matures into those areas, it has the real promise of solving some of the massive problems that have so far been chased only by policy or contract. The more you can get stakeholders to genuinely collaborate — and have real incentives to collaborate — the better all of this gets.
The Core Problem: Power Imbalance and the Fear Dynamic
When somebody does work on a job, they should be paid for it. When somebody provides materials to a job, they should be paid for it. That's simple. Everyone will agree to that.
What happens when you add layers to it is that fear gets injected into the environment. A simple example: you have an owner who hires a general contractor, who hires a subcontractor, who gets supplies from a supplier. The owner is afraid the general contractor won't pay the subcontractor. The sub is afraid the general contractor won't pay them, or that they won't be able to pay the supplier. You have four stakeholders who all agree everyone should get paid, but each of them is a little scared it won't go the way it should — and for legitimate reasons: someone might be irresponsible, circumstances change, projects run into problems.
So what do they do? They start taking protection. And when the parties have different amounts of leverage, the party with the most leverage starts demanding more and more protections, which become more and more onerous for everyone else. That's the risk problem in the space in a nutshell.
There's this constant battle in construction between contract and policy. The parties contract with one another, make agreements about who has which rights and when people get paid. And then the government comes in and sets policies about what you can and can't do. This happens in the States, it happens in England, it happens everywhere. Construction policy is very specific and constantly chasing the contracts. A classic example is the "pay when paid" clause — every construction contract pretty much everywhere has a provision that says: I will pay you when I get paid. Straightforward enough. But what happens if the general contractor doesn't get paid? Does the subcontractor simply not get paid either, even though they did the work and owe money to their materials supplier? Courts in the US have generally said no — "pay when paid" is just a timing mechanism, not a way to permanently shift risk. So contractors moved to "pay if paid" clauses, making the shift more explicit. And over 10 or 20 years, most courts have come back and said: you can't do that either. You can't shift to the subcontractor the risk of the owner not paying the general contractor.
That's one example. Lien laws, retainage laws, prompt payment laws — it all works the same way. It's this constant tug of war between what the powerful parties want to contract for and what society, through policy, says is fair. Because even though construction involves independent contractors rather than employees, the underlying principle is the same as the person working at McDonald's: if McDonald's has a bad month, that's McDonald's' problem. The workers still get paid.
What I'm Still Looking For: Disempowerment and Rich Barton's Playbook
One of the things that frustrated me most about selling Levelset — or stopping Levelset — is that the mission isn't done. The construction industry is still an environment with stakeholders who have perverse incentives. The payment process is still complicated, slow, and administratively burdensome. The payment data actually suggests things have gotten worse since we started — not better. Part of that is because the industry has gotten more fragmented. There are more layers, more specialization, more stakeholders on a job site today than there were in 1950 or 1960. Every layer you add makes the payment process more complicated. More onerous.
Technologists look at this as a technology problem. But in reality, it's a risk problem and a risk structure problem. And I'm somewhat pessimistic that technology alone can solve a non-technology problem — which is fundamentally the explosion of trades and stakeholders and all the complexity that adds.
What I do look for — and what I think about a lot when I think about starting something new — is disempowerment. Where are people disempowered? What is disempowering them? What's not available to them?
I became a big fan of a guy out of Seattle named Rich Barton, who built Expedia, Glassdoor, and Zillow, and is today the CEO of Zillow. He has this concept he calls "power to the people." I basically ripped that off. He looks at where knowledge and information is uncommon or unavailable, and asks: how do you make it available? When he started Expedia, he was looking at the travel agent space and asking: why do travel agents have all this information about airfare and hotel availability that regular people can't access? With Glassdoor: what information is missing about what it's actually like to work at a company? With Zillow and the Zestimate: property records, home values — things that existed in fragments. He plays that same tape over and over again.
At Levelset, we were playing the same tape. What are these contractors and suppliers and people in the industry not able to see, that's causing them so much pain around payment? It was all these rights that they had, all these legal intricacies that were incredibly complicated, different in every state and for every project type, requiring either expensive legal counsel or being ignored entirely. How do you take all that and bring it to people in a way they can actually use — without them having to hire an attorney every time?
The opportunity to empower people who are disempowered — that is what I go back to. I see it in construction overall. I see it in property restoration. I see it in residential, commercial, civil — all across the industry. When you get away from the skill of swinging the hammer, there are people who need to run their business, and they are navigating incredibly sophisticated contracts and leverage scenarios. A construction contract is ridiculously more complex than the one you sign when you make a restaurant reservation. And not everyone goes into a construction project with the same understanding of their rights, their contracts, or their situation. That gap is enormous. It's where the opportunity is.
Go to Market: Help First
One thing that I think is important about the construction technology space is that these businesses and these people have a really high appetite for help. They need it. They're always looking for resources. They're always using different types of professionals and services.
When I think about Levelset's go to market, honestly, I'm not sure I ever really formally sat down and defined a go to market strategy. It was very organic. I had been blogging since I was 15, so content was just running through my blood. But the other reason it was natural was simpler: you could just tell that the way to help this audience was to deliver them genuinely useful information.
Over time, we developed a core value that I'd describe as "help first." It's broader than content marketing — much broader. Our sales team was actually instrumental in crystallizing this, because what they noticed in their own process was that they were successful not when they were calling to sell something, but when they were calling to help. You can apply that principle on the product side, the sales side, the marketing side. And it changes things fundamentally.
When companies and founders come to me for advice, I notice how much most of them want to sell their product. Their website is full of product content. Their blog is full of product announcements. Their press releases are about features. I get it — you need revenue. But there's a great book by Adam Grant called Give and Take, and it's about givers and takers. Marketing, product, and sales teams don't think of themselves as takers — but if you really dig in, they often aren't giving. And giving first, or helping first, just works. Taylor Swift said karma is real — and there's something to that. If you're selfish about it, you can take that energy all the way to the bank.
At Levelset, we were so committed to this that we had rules not to write about Levelset, not to post self-promotional content. My salespeople thought I was extreme about that, and maybe I was a little. But if you're going to be extreme one way or the other, I think that way is better.
On Advising vs. Operating
When I advise companies and try to help with content or go to market, one thing I've learned is that advising is very different from being a CEO. When you're a CEO, the company is a reflection of you in many ways. All the advice in the world I can give to another CEO isn't going to fundamentally change what their strengths are or what the complexion of their company will be.
The real advice is: figure out who you are. What about your approach, your skills, your passions, is going to create something special? What are you going to be able to produce that nobody else can? Everybody has things in them that they sometimes fight because they think it has to be done a different way. But a founder's most honest advantages are usually the ones they're not even thinking of as advantages.
I think it's actually a little bit of torture to advise people. When you are an operator — and I love operating — you sometimes look at a situation and think: I know exactly what to do with this. And that can be painful when it isn't yours to execute on. But what gives me peace is this: building a company isn't something you can just pick up in December or January or next year. It's seven to ten years of work. It's like writing a long book or building a large construction project. You have to be willing to go through that. And just because I've done it before doesn't mean it'll work — it'll work only if I go make it work over a long period of time.
And that goes back to why it's so important to do things you're genuinely passionate about. Because you're going to be sacrificing a lot. If I get back into something, I want to get back in because I can't not be in it. That's the standard I'd hold myself to.
What I Miss — And The Fingerprint
There's a lot about building a company that can be torture. But there's also a lot that's really beautiful. There are a lot of high points, a lot of achievements. And when I sit and think about what I miss, the thing that stands out most is the team — who you're working with and the things you're able to do together. The chemistry you form. I miss it a lot. But I also know that it's not something you can ever fully recreate.
I used to always say that a construction project is like a fingerprint. The 50, 100, maybe 1,000 stakeholders who come together on that project will never work together in exactly that way again. A company is the same thing. Levelset was an absolute fingerprint. The team was very special. I can't take that and just go do it again — it'll be something different, something new, something that has to be put together all over again. And it'll be its own fingerprint.
And that's also a comment on culture. The Levelset culture was super valuable and super unique. If you could put culture on a balance sheet and call it an asset, it would have been by far our biggest asset. It produced things — products, go to market opportunities, customer outcomes, fundraising opportunities, and ultimately an exit opportunity — in ways I wouldn't have expected. Culture really did do that.
But I can't transfer it. If I build another company, the culture will be different. I'd be conscious of it, I'd work on it, I'd want that asset. But culture is a squirmy asset. It's very hard to get your hands around. What you miss is what it's like to work with people who have a shared understanding, who are learning about the problem together, who help each other build a product, a company, a customer base. Those things become very special. And you just know how hard and tender and squirmy it is to build something like that again.
Final Advice: Run Your Race
The advice I most find myself coming back to when founders come to me with worries is simple: run your race. There will always be other companies on the same path as you, big market players doing something nearby, things you read that shake your confidence. And the advice isn't not to worry — the advice is to know those things, not be ignorant of them, but also not let them become distractions from your own path.
You have to have a North Star. Don't compromise it, don't stop believing in it — unless something truly drastic is happening. Just keep running your race, keep moving forward. That's what keeps you building value. That's what keeps opportunity flowing.
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