But, you know, it's really come up in the last 5-6 years. And unlike a lot of middle market brokers, and there are a lot of, or a good number of good-sized middle market brokers, Baldwin has, and Trevor, who's been leading the effort, has done a lot to consolidate, integrate, and bring technology into the business and develop some really interesting platform businesses within Baldwin. So, you know, on the surface, again, they, they do have a lot of similarities with some of the other middle market brokers, but we're really building a differentiated franchise. With that, Trevor, if you wanna take it away.
Great. Thank you, Adam. I believe this is the clicker. Yes. All right.
Good afternoon. I'm Trevor Baldwin, and I'm Co-founder and CEO of the Baldwin Group. I'm joined here this afternoon by Brad Hale, who's our Chief Financial Officer. Quick background on our firm. I co-founded the Baldwin Group in 2011. That year, we did $5.5 million of revenue and had approximately 35 colleagues in the business. Since then, through our outsized organic growth, as well as our M&A strategy, we've accelerated the business to the roughly $1.3 billion of revenue we are today. When you look at the business and how it's constructed, we go to market under three operating segments, and I'll get into those here quickly or shortly.
But I think importantly, you know, we took the company public in October of 2019, that year at roughly $150 million of pro forma revenue. Since then, we've acquired roughly $500 million of revenue, but accelerated the rate of our organic growth along that time period, bringing us to the $1.3 billion of revenue and generating industry-leading organic growth in each of those years. When you look at our business and how we have grown and developed over time, you can look at, you know, the first seven years before our IPO as really kind of foundation building, where we built the bones of our culture and really the roots of our status as a destination for the industry's best and brightest.
This is, you know, where we crafted our strategy around our three operating segments, both how we vertically integrate into the insurance value chain via MGA, but also our embedded insurance platforms and how we go to market at point of transaction. At the time of the IPO, we saw an immense opportunity to continue accelerating the growth of our business and had an incredible opportunity to partner with our name to acquire some of the highest quality independent firms across the U.S. We completed roughly 30 transactions since going public, adding roughly $500 million of revenue, and importantly, investing deeply through our P&L to fully integrate the organization. Today, we operate on a single technology stack. We have a common org structure across the organization. We have a common go-to-market model in each of our three businesses.
Effectively, we operate as a single business around a single culture, and while relatively simplistic, I would tell you that that's a highly differentiating fact set relative to many of our peers, particularly on the private side across the industry. Going forward, as we sit here today, we have achieved a relative amount of scale that gives us optionality going forward. We have a business that has proven it can consistently grow double digits organically through the cycle. We have a margin profile that is far from mature, leaving significant opportunity for accretion going forward.
We are quickly approaching a real inflection point in the financial profile of our business as we bring leverage down from a high point of 5.8x in April 2022 to just under 4.5x at the end of the first quarter, and an expectation of getting that at or below 4x leverage by the end of this year. While we're doing that, we'll see free cash flow from operations truly inflect in the business and wrap up the last of the large earn-out payments that we have due from prior M&A in the first quarter of 2025, after which point, the free cash flow generation of this business will be immense.
Going forward, we set out a goal at the time of our IPO to build a top 10 global broker, and we feel incredibly good about the path we're on to achieving that objective. Today, we're the 18th largest broker, with a path to continuing to accelerate that through our industry-leading organic growth and what will likely be more episodic and opportunistic M&A going forward after we bring our financial leverage profile down safely below four turns. When you look at our three operating segments today, the first of which is our Insurance Advisory Solutions business, that comprises roughly 50% of our revenue. This is business where we provide retail insurance broking and advisory solutions to mid-size and large businesses and high-net-worth individuals and families. Importantly, we've developed a proprietary way in which we go to market in this business called the Risk Mapping process. It's a five step-...
diagnostic client engagement model that affords us, on average, an 85% win rate when we get in front of a prospective client. And that compares quite favorably to the industry's average quote-to-bind ratio of roughly 10%. And so when you look at our outsized double-digit organic growth, it's driven by our ability to take share and win more than our fair share of new clients on a consistent and ongoing basis.
In our Underwriting Capacity and Technology Solutions business, this is where we're innovating via our ability to vertically integrate into the insurance value chain, building proprietary insurance products that meet the unique in-market needs of particular client segments, and leveraging our proprietary technology platform that powers this business to embed certain of these proprietary products into embedded insurance ecosystems, creating a platform effect around the distribution of those insurance solutions, both direct via software providers and indirectly through our Main Street Insurance Solutions segment, which I'll talk about here shortly. The UCTS business is an MGA platform where we build, underwrite, distribute, and adjudicate the insurance products. But importantly, we don't take any balance sheet risk. We source third-party risk capital from the global reinsurance communities to support these products and their ongoing scaling.
We launched this segment in April 2019 with the acquisition of what was at the time, Millennial Specialty Insurance. When we bought that business, they had a single product, renters Insurance. They generated roughly $60 million of Gross Written Premium, and they had 70% concentration with their largest shelter distribution partner. Today, this business has over $915 million of Gross Written Premium across 12 products that we've built and launched over that time period. And renters insurance represents less than 25% of our overall Gross Written Premium. While continuing to scale at similar overall organic growth rates to the balance of the UCTS business, the renters product continues to perform exceptionally well, but we have tremendous opportunity to continue building, launching 3-5 new products each and every year, creating an ongoing flywheel effect for our organic growth profile.
Last, we have our Main Street Insurance Solutions business, comprising roughly 20% of our overall revenues. This is where we're innovating the way in which personal insurance is ultimately distributed and consumed. Namely, we are the leader in embedded insurance solutions at point of transaction. We have a belief that personal insurance, in general, is a secondary transaction. Why do you buy homeowners insurance? Because you can't close on your mortgage or your new home until you have it. And so we have carved out a niche for ourself as the leading purveyor of embedded insurance solutions at point of new home sale. In fact, we're the contractual exclusive provider for eight of the top 10 new home builders in the U.S.
We've seen our attachment rate on their new homes sold across our builder channel partners grow from mid-40s% in 2022 to 58% in the first quarter of 2024, showcasing how we continue to get even more effective at embedding our solutions at point of transaction over time, via ongoing technology development, as well as process enhancement and where we fit into that new home sales cycle. Additionally, we're building out a similar business focused on the mortgage origination and real estate brokerage channels, where we're having early but growing success around building the leading solution for embedded insurance solution at point of mortgage origination and home sale.
Importantly, when you take those three operating segments together and each of their unique ways in which they're going to market, it creates for us an organic growth flywheel that has incredible durability and sustainability that will persist through market and economic cycles. What you see on this slide here in the dark blue bars is our organic growth rate across the Baldwin Group in each of these time periods, compared in the light blue bars to the industry peer average organic growth rate during that same time period. I would point you to the dotted box at the bottom right-hand side of our organic growth charts. What that shows is what is the impact of insurance rate and economic expansion or contraction on our overall organic growth rate during that time period.
What you can see here is only 10%-20% of our organic growth is driven by those third-party forces of rate and exposure. The vast preponderance of our organic growth is driven by the fact that we go out and sell and generate meaningfully more new business than our peers on average. Over these same time periods, our peer organic growth would have seen 50%-75% of that growth being generated from rate and exposure, making them far more susceptible to the market cycles. This is highlighted by the fact that during 2023, we generated sales velocity of 17%. That compares to the industry average sales velocity of 11% and the 75th percentile of 15%. In the fourth quarter of 2023, we generated 21% sales velocity.
and put up record new business for the history of our company in the first quarter of 2024. Our organic growth profile is something we're incredibly proud of because of what it says about how we're showing up for our stakeholders. When you have consistently outsized organic growth, it means that your clients are continuing to honor you with their renewals at an outsized rate, meaning they're seeing real value in the work and advice that you're delivering to them. It means that you're out taking market share every day at a rate that meaningfully exceeds what your competitors are doing, meaning new clients seeing value in what we're offering, the advice and solutions that we're bringing to bear relative to what's on offer from our competitors.
Importantly, it means that our colleagues are showing up in an incredibly powerful way, each and every day, to ultimately power these results. So, how are we able to generate that consistently outsized organic growth? Well, in our IAS business, as I mentioned earlier, we've developed a proprietary go-to-market model, the Risk Mapping process. What does that enable us to do? It enables us to bring new-to-industry professionals into our business and make them far more productive than the industry average sales professional because we have a common way in which we train, develop, and manage the sales process. Doesn't sound like rocket science, but relative to our industry, is actually quite unique. So you can see here, by the third to fourth year that a new hire is with us, they're generating nearly 2x the industry average sales per individual.
Mature risk advisors, our nomenclature for an insurance sales professional, at over four years, is generating three times the industry average production. It's not just distinct to how we're able to onboard and make productive, quickly, new-to-industry professionals. You can see on the right-hand side here, we are also able to have a meaningful impact on the productivity of the sales force of newly acquired businesses. On average, the firms we've acquired since 2019, their sales force was generating $150,000 of new revenue per sales professional. That, over the 2022-2023 time period, those same businesses, those individuals, were generating $260,000 of new business, nearly doubling the productivity from mature advisors.
As we bring them into our platform, we train them on our go-to-market model and provide seamless, unfettered access, access to our unique incline industry sector capabilities and solutions. In our UCTS business, our MGA platform, as I mentioned earlier, we have rapidly scaled this business over the past five years through a combination of accelerating growth in our core product lines, as well as the ongoing development and launch of new products. You can see we've grown the business from $77 million of premium concentrated in a single product line to $915 million of gross written premium as of the end of the first quarter of 2024, all while delivering industry-leading organic growth and industry-leading loss ratio results.
In fact, in aggregate, since inception, our programs have generated loss ratios of less than 50%, and they have also generated loss ratios of less than 50% each and every year that we've been operating. So not only an inception-to-date fantastic performance, but a calendar year-to-date exceptional performance. That's incredibly important in an MGA business, where the most important stakeholder is your capital provider, because without risk capital to support your products on an ongoing basis, you cannot continue to grow and scale your platform. Then lastly is our Main Street insurance business, where we're innovating the way in which personal insurance is distributed and consumed. We are the industry-leading purveyor of embedded homeowners insurance solutions at point of new home sale.
The Westwood business, which we acquired in April of 2022, was roughly $80 million of revenue and $32 million of EBITDA when we acquired it. Last year alone, that business generated $129 million of revenue at a low- to mid-40s% EBITDA margin, an incredibly profitable, high-growth business that has a leading market position in the new home builder marketplace. Similarly, we're investing deeply in building out similar capabilities in the mortgage and real estate brokerage channel. This year, from a standing start in 2022, we'll generate roughly $18 million of commission revenue in our mortgage and real estate brokerage de novo startup business. We'll lose roughly $14 million on that startup.
However, we expect that business, on a run rate basis, to hit free cash flow breakeven and positive run rate at some point in the fourth quarter of this year or first quarter of next year. The momentum in that business is fantastic as we see 60%-70% year-over-year organic growth on a monthly basis. Lastly, an important part of our value creation algorithm over time is our ability to attract the highest quality platforms in our industry, acquire them in, and make them even better... You can see the organic growth profile of the businesses we've acquired over the past several years. In the 12 months leading up to our acquisition, on average, growing at 12%. Strong results, regardless. But in the first 12 months following our transaction, growing on average, 26%. That is for a number of reasons.
One, our M&A strategy is highly differentiated. We tend to do larger transactions at a lower quantity, acquiring generally larger businesses of much higher quality. We tend to historically have paid at the higher end of market because we are buying the very best, highest quality businesses, but then we quickly de-lever our purchase price via growth. And you can see how that's articulated in the 2020 cohort, where our average multiple reduced from 13x to 10x over that three-year ownership period after paying out our earn-outs. Based on current trends, we expect our 2021 cohort to de-lever from a similar upfront purchase price of mid-13s down to somewhere between 9x and 10x, so down into the high single digits after paying our earn-outs.
Those are the two cohorts with the most and significant of ongoing investments during their early years to build out our national platform as we were scaling from a regional business to a national business. And we expect our 2022 cohort to de-lever from a similar 12x-13x upfront purchase price to below 6x by the end of our third year in the settlement of the earn-outs, showcasing the margin accretion and leverage, operating leverage inherent in our business as we've built out our national platform. Brad, do you want to talk a little bit about the numbers?
Yeah. So, if you look at this slide, I think it's, you know, one graph does not... which one doesn't belong, right? One of these does not look like the others. Obviously, we have scaled the revenue of the business substantially, since our IPO date in 2019, effectively 10x-ing the business. In addition, Adjusted EBITDA on a total dollar basis has grown similarly. What has not grown similarly is our margin, and that's a direct result of what Trevor just articulated in his presentation, which was deeply reinvesting back in the business, across that time frame. So let me give some examples. One, in the UCTS platform, that Trevor mentioned, where we've scaled from one product to 12. When we went public, we had about 20 people in the UCTS segment supporting just the renter's product.
We now have 800 people in the UCTS segment, as we have built the infrastructure, from an underwriting perspective, from an actuarial perspective, from a technology perspective, to have our proprietary tech support the number of products we've built. It is fueling substantial growth in that business, and as those products mature, the margin does start to show up. But the early margin of those newly launched products is not what the mature margin of the existing products are. In addition, as Trevor mentioned, in the Main Street segment, we've got a very successful platform operating at a mid-40s% margin in Westwood, where we've got established long-term relationships. The Westwood business is 50 years old. But we're trying to replicate that in the mortgage real estate space.
We see real first mover advantage there, and so we're spending the capital to come up with what would be a similar tech-enabled platform that would provide a frictionless experience for the client who is buying an existing home or refinancing their existing home. That business is a significant drag on margin now, but again, we see the first mover advantage that we've established in the builder network, and we're trying to replicate that in the mortgage real estate space. Then finally, in the IAS business, where we acquired nearly $400 million-$500 million of revenue over a three-year period, that has taken a fair amount of infrastructure build alongside of it.
Sales leadership, regional leadership, having that business go to market as a single brand, establishing the right amount of cross-sell opportunities through revenue sharing arrangements and somebody administrating that. So that has been an additional drag on margin with respect to the business. And then finally, in the corporate segment, you know, we went public as a very small company. At the time, we had material weaknesses in internal controls. We have since, two years ago, remediated all of those, but we've built an IT function and an accounting and finance function that has matured substantially from where we were five years ago. The good news is we don't have to rebuild that. We don't have to rebuild the scale and infrastructure in the MJ that we've built.
We don't have to rebuild the corporate infrastructure we've built. We don't have to rebuild the sales leadership and infrastructure in IS that we've built. We don't have to reinvest in Main Street the way we did to get it from start-up status to now, where, as Trevor mentioned, it's near breakeven here at the end of this year. So the margin expansion opportunity is substantial. We started to see it in Q1 this year. We had 280 basis points of margin expansion. We have communicated and guided to 250-300 basis points of margin expansion in 2024. And that sort of takes us to our next slide. The punchline of this slide is each of these three graphs are leading to one thing, which is free cash flow generation.
So, you know, if you look at the brokers, our peers, what are they known for? And why people would love to invest in this business is because of free cash flow generation, and it gives you a ton of optionality, with respect to either inorganic investment, organic investment, paying a dividend, getting your debt very low from a leverage perspective.... And we've got, luckily, all three of these going in our direction. So at the top, you've got, expanding both EBITDA dollars and margin, and we expect that trend to continue. We have communicated that we do expect to continue to expand margin in each of the next five years going forward, as we have steadied the business, from a hiring perspective and continue to see the organic growth outperformance that we've done historically.
In addition, our earn-outs, if you look in the bottom left, are effectively over when we get to Q1 2025. We're gonna throw a massive end of earn-out party, if any of you would like to attend. But that, as far as a use of capital, will be a significant change from where we have had to devote cash flow over the last several years. And then finally, we had a recent refinancing of our debt. If you see, we've scaled from $22 million in 2021 to $105 million last year. That's a pretty expansive use of cash in terms of cash interest, but that is steadying. We just put a new capital stack in place, fixing a portion of our debt. We've got seven year tenor on that.
and so depending on where rates go on the remaining variable or floating portion of that debt, we could see this decline, but at worst, it stays flat and becomes less of a percentage of our overall EBITDA as it has been in the past. Again, each of these creating a real inflection point for us in terms of free cash flow going into the back half of 2025 and into 2026.
So to wrap up, as we look across our business and where we sit today, you know, we're at a real inflection point in our story. We came public in October of 2019 as a subscale insurance broker with some real ideas around opportunities in the market to accelerate growth and differentiate ourselves. We have today now built scale across our three core businesses. We have proof of market concept, and we've proven over the past five years that we have real durability in the underlying organic growth profile of each of our three businesses, and even more durability when you bring them together in a cohesive and combined manner. Our business is at a real inflection point from a financial profile perspective, as Brad articulated.
You have leverage coming down, you have free cash flow going up, going up, and we're quickly approaching the end of the large earn-out payments we have due from the M&A that we did in the early years post-IPO. Our opportunity here is immense. We have a real algorithm for how we continue to drive this outsized organic growth while delivering on meaningful margin accretion going forward. We have a massive growth opportunity, we have a margin that's far from mature, and we have growing free cash flow that will create a lot of financial flexibility and optionality for us on an ongoing basis. So with that, I think we're gonna take questions in here, 'cause we're the last last to present today, so we don't have to clear the room.