In short
Building a roll-up integration “engine” from day one in insurance brokerage acquisitions; why failed processes happen when integration isn’t real (especially around data, technology, and proof of organic growth).
Guest backgrounds
Matt James is EVP, CFO, and Chief Acquisition Officer at Oakbridge Insurance, a PE-backed insurance distribution roll-up platform he co-founded in 2020. He has 20+ years in M&A (investment banking, principal investing, and operator roles), with about half his time in insurance brokerage. He’s closed 60 deals at Oakbridge in five years (12 in the last year) and has integrated acquisitions starting at closing with most workstreams completed in 90 days.
Key claims
Buyers now diligence organic growth components (not just ability to do deals), cross-sell as trackable organic growth, and integration quality (not “lip service”). Cultural fit is binary. Data readiness and moving to a single ERP instance are critical; weak data standards and outdated tech are major red flags.
Notable examples
Two “billion-dollar revenue” sponsor roll-ups failed because they weren’t truly integrated (data warehouse aggregating 15+ ERPs/payroll systems) and couldn’t prove marketed revenue/integration proof points during 90–120 days of diligence; valuation expectations collapsed and buyers stepped away. Oakbridge uses DealRoom as single source of truth and a “new partner operations” leader to quarterback LOI through 90-day integration and seller education.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOGuest Introduction: Matt James
2:27 to 3:37
Meet Matt James, a key figure in M&A with a focus on integration and deal execution.
“And that comes from learning from the best who've done it.”
Building Integration in M&A from Day One
3:38 to 4:52
Learn how to incorporate integration as a core part of the M&A process for value creation.
“someone who's built the system from scratch and watch competitors who didn't pay that price go through failed processes as a result.”
Changing Buyer Diligence in M&A
4:53 to 6:45
Explore how buyer expectations have evolved to focus more on organic growth.
“insurance brokerage strategies, really to build and lead those M &A functions.”
Understanding Organic Growth and Cross-Selling
6:46 to 8:46
Delve into the importance of organic growth and effective cross-sell strategies.
“When you think about the sponsored investor community, the M &A muscle can definitely be built, but driving organic growth is much, much more difficult for a high growth acquirer.”
Integration Challenges and Best Practices
8:47 to 11:17
Discuss the key challenges in integration and how to approach them effectively.
“is something that buyers care very much about in today's market.”
Evaluating M&A Deals: Key Criteria
11:18 to 13:32
Learn about the critical criteria for evaluating M&A deals, including culture fit.
“and being able to show those proof points on, obviously there's the expense energy side, but that revenue component that I mentioned is really critical today.”
Validating Cultural Fit in M&A
13:33 to 14:02
Understand how to assess cultural fit during the M&A process to ensure success.
“There's a number of what I'd say typical deal pillows for us around the integration piece.”
Identifying Integration Challenges
14:02 to 15:10
Learn about the red flags that indicate potential integration issues post-acquisition.
“If we took the culture piece, how do you validate that?”
Building Relationships in Deal Processes
15:10 to 16:34
Explore the importance of relationship building in securing successful acquisitions.
“Historically, about 75 % of our deals have been proprietary.”
Investment Criteria and Transaction Volume
16:34 to 17:55
Understand the criteria and volume of transactions that define their acquisition strategy.
“What percentage of these were banked versus proprietary deals?”
Show all 27 chapters
Equity Structures in Acquisitions
17:55 to 19:44
Gain insights on how equity considerations are structured in acquisition deals.
“All of our deals also have an earn out component.”
Market Trends and Deal Failures
19:44 to 20:21
Discuss market trends and the reasons behind the breakdown of high-value deals.
“What percentage of that purchase price gets allocated on the earn-out?”
Diligence Process and Integration Challenges
20:21 to 23:02
Learn about the diligence process and the common integration pitfalls that can arise.
“The one thing I was curious about is what you've seen in the market.”
Navigating Data Management Issues in Acquisitions
23:02 to 26:01
Explore the importance of effective data management during the acquisition process.
“So there's definitely how well the company's consolidation play has been integrated and then How are they actually taking a market?”
Innovations in the Acquisition Process
26:01 to 28:00
Discover innovative strategies implemented to enhance the acquisition process.
“Day one, it was just us and a checkbook for the first year.”
Transitioning to a Deal Room for Integration
28:00 to 28:43
Learn about the shift from Excel trackers to a centralized deal room for M&A.
“What I'll say is about two years ago, we also moved away from the historical Excel tracker sheet to the deal room as our kind of source of truth on the hard data piece.”
Optimizing the Acquisition Process
29:14 to 31:28
Explore how to look at the acquisition process as a continuous journey.
“So I like it is one is like literally looking at your whole process from LOI through integration as one continuous process.”
Bridging Diligence and Integration
31:28 to 33:59
Understand the challenges of connecting due diligence with the integration phase.
“That's like the big piece that kind of gives them a lot of heads up of what's to come and get them prepared for it.”
Implementing Deal Room for Management
33:59 to 35:58
Learn how a deal room facilitates M&A processes and enhances organization.
“You mentioned source of truth and deal room.”
Building a Data Platform for M&A
35:58 to 40:04
Discover how data analytics transforms M&A practices for better decision-making.
“That's a great way to go revisit two years, three years down the road, particularly when they're through their earn-out period, and just understand how that business performed based on what you underwrote at the time.”
Key Performance Indicators for Acquisitions
40:04 to 43:24
Identify essential KPIs for assessing acquired businesses and their performance.
“And then right now we're pushing through the ability to look at individual producer level.”
Cultural Integration in Acquisitions
43:25 to 45:14
Understand the importance of aligning culture during acquisitions.
“I'm just wondering like the things that you learned in terms of surprises that come out after close or the hidden operational issues that you find out the hard way.”
Building a Pipeline Through Acquisitions
45:16 to 46:44
Discover how to create a referral engine with recent acquisitions.
“Like, how do you build pipeline that way?”
The Role of CFO in M&A
46:45 to 48:56
Explore the dual role of CFO and Chief Acquisition Officer in M&A.
“somebody in another geography that they would recommend to us.”
Financial Considerations in Acquisitions
48:57 to 51:52
Learn how to assess the financial impact of acquisitions on business valuation.
“I'd say day one, it was just, hey, do we want to spend the money on this new startup?”
The Importance of Data Management
51:53 to 54:20
Understand why data cleanup is crucial before pursuing acquisitions.
“what other levers can we pull on the revenue side around?”
Lessons Learned from M&A Experiences
54:21 to 56:00
Hear anecdotes and key takeaways from M&A experiences.
“Any other takeaways, things you've learned over the years?”
Transcript
Automatic transcript. May contain errors.0:01Hey M &A scientists, before we get started, we just launched the M &A fundamentals certification on DealPilot, and I'm really proud of this one. I was personally involved building it out with PhD learning development professionals. It covers the full M &A lifecycle, buy side, sell side, key terminology, and the buyer-led M &A framework, over 60 templates and artifacts. So you're not just learning concepts, you can actually go execute. This isn't one of those certifications that charges you thousands of dollars to teach you stuff you can find on Wikipedia. This is how I've actually trained people, practical, comprehensive, and built from real deal experience.
0:43It's all part of the M &A Science subscription, and the next certification track is coming up in a couple months. Check it out at mascience.com. All right, let's get into it.
0:57Hello, M &A scientists. If you haven't grabbed the state of M &A report from Deal Room yet, it's a good time to check it out. We're three months into the year, and this gives you a reality check on what you should be focused on. It's based on input from deal teams across different industries, and it shows the gap between where people think they should spend time versus where the real problems are. If you're trying to set realistic goals or get everyone aligned on what matters, this gives you the data to back it up. Download it for free today at dealroom.net slash report or click the link in the show notes.
1:32That's dealroom.net slash report. Now back to the episode.
1:41I'm Kisan Patel and you're listening to M &A Science, where we talk with deal professionals and learn valuable lessons from their experience. This podcast focuses on stories, strategies, and what actually happened during M &A deals.
2:05Hello M &A scientists, welcome to the M &A Science Podcast. This show is part of our mission to rethink how M &A is done and build the operating standard for BuySide M &A. That old school seller that approach? Instead, BuySide M &A is about strategy, alignment, and execution, putting value creation at the center of every deal. So it's not just about closing the deal. It's about making it successful. And that comes from learning from the best who've done it. If you want to go deeper, we got you covered. There's tons of free resources on our website. We've got frameworks, guides, tools, all built from real operator experience.
2:39We also have the M &A Science membership, which gives you the full system, exclusive frameworks, templates, expert Q &A sessions, direct access to me, and the AI-powered intelligence hub. It's a home of Biolet M &A. Find all these resources at mascience.com. That's mascience.com. Let's jump into it. I'm your host, Kisan Patel. Today, I'm here with Matt James, EVP, CFO, and Chief Acquisition Officer at Oakbridge Insurance, one of the most active roll-up platforms in the insurance distribution space. He's closed seven deals just this year with another one on the way and has built an integration function that PE buyers are now treating as a differentiator, not an assumption.
3:22Matt sits at the intersection of finance, deal execution, and operations in a way that most M &A functions never achieve. At a time when consolidators are getting consolidated and buyers are scrutinizing integration quality harder than ever. This is a conversation with someone who's built the system from scratch and watch competitors who didn't pay that price go through failed processes as a result. Today, we're going to talk through building a clear framework for how to build integration into your roll-up process from day one, not as a back-office cleanup project, but as a value creation engine that makes your platform more attractive to the next buyer.
3:59Matt, how are you doing? Great. Thanks for having me today. I'm excited to join you. Thanks for taking a break from doing deals to have a conversation with me. Can we kick off with a bit about your background? I spent the last 20 or so years in and around M &A, either as an investment banker, principal investor, and most recently operator across a host of different industries. But about half that time has been spent in insurance brokerage. Most recently, I've been part of two different PE-backed insurance brokerage buy and build strategies. That includes my current role at Oak Ridge Insurance, which I helped co-found in 2020.
4:33Coming out of school, early career, I wasn't really seeking an M &A or finance role. I was a history major during undergrad, but landed early career with an evergreen investment vehicle and kind of just fell in love with, I'll say, like the action and complexity around M &A. These last two roles where I've been more on the operator side focused on ground floor insurance brokerage strategies, really to build and lead those M &A functions. Those have been particularly interesting. Both I joined early on. Oakbridge, I was employee number one. Prior to that, I was part of the corporate team that came in within the first deal.
5:09A lot has evolved recently, and the level of sophistication around the space, around quality has increased. And what we've seen recently is compression of multiple arbitrage, and that's eliminated a lot of that, I'll say, key historical value creation lever. How many deals have you done across your career? Oh, total more than 100. We've done 60 just at Oakbridge in the last five years and three months. We've been quite busy. 12 last year, so about one a month is our typical pace. And those vary from larger platform operations, new geographies, new specialties, all the way down to small tuck-in or roll-in deals to our existing platform.
5:49So pretty broad spectrum of size and scale, squarely in that middle market space. Let's talk about the market. It's obviously, we've referenced it. It's changed. It's evolved. Buyers used to ask, can you grow? Now they're asking, how are you growing? What did you actually do with what you bought? When does that shift happen? That sounds like an obvious question that any buyer would ask, but that level of buyer diligence and deep dive really started to ramp up, I'm going to say five or so years ago, right around the time that we formed Oak Ridge. I will say in the last 12 to 18 months, that's ramped up even more.
6:25The diligence processes, we've seen some of those that have broken down over the inability to disaggregate organic growth from inorganic. Today, I think these buyers, which includes us when we're looking at our latest add-ons, they really care about the components of our organic growth much more than they care about ability to prosecute M &A in a roll-up strategy, for example. When you think about the sponsored investor community, the M &A muscle can definitely be built, but driving organic growth is much, much more difficult for a high growth acquirer. Disaggregating that organic growth piece for us into a few kind of key dimensions really leads to a higher conviction on a transaction, particularly those where we're paying top of the market multiples, where there's an expectation that the seller has the culture and infrastructure to drive that organic.
7:16In our space, we break that down by line of business, recurring versus non-recurring revenue, especially in program, region, geography, even all the way down to the individual producer or salesperson level. And that's really critical to proving out that organic growth engine, whether we're the buyer or we're the seller when we go through our periodic recaps events. On top of that, disaggregation of those key KPIs like sales velocity, lost revenue versus lost client count, market drivers that are outside your control around organic growth, like rate increases being passed through by insurance carriers.
7:52All of that is becoming much more critical to the diligence process, particularly as these roll-up strategies grow and mature and move up market. For us, it's all about that organic growth piece. Maybe the last piece on diligence on what are you doing with what you bought is really around the cross-sell potential. We buy insurance brokers across a lot of different lines of business, a lot of different geographies, and being able to support that cross-sell initiative that's critical to proving those trackable KPIs, making sure you have a clear and simple incentive compensation structure that rewards that activity of cross-sell.
8:29and ours is both cash and equity-based. So we're a pretty broad distributed equity model in our business. And then finally, that company-wide dissemination and training on that cross-sell piece, bringing to bear specialty expertise, unique capabilities that we've built internally, and then the right to win across those multiple lines of business is something that buyers care very much about in today's market. So one was the organic versus inorganic, that there's a lot more diligence on your actual organic growth. And that this means some real clarity on some KPIs that give you those indicators of how well you're doing organically.
9:07And then when you mentioned this cross-sell, which this is the big shift in the last five years, like you have to have real synergies. You just can't consolidate a bunch of companies, have a high gross revenue that's going up in the right direction. And that's it. And you call it a day. Yeah, it's not just expense synergies anymore. The buyers are focused on driving that organic because when you think about those levers on what builds value across that whole period for a sponsor, you used to get a lot of multiple arbitrage with these deals. You might buy something at six or eight times, you get out for 12 or 14 times.
9:40The market is really closed on that. There's a much smaller spread on the multiple arbitrage side. So you're building the majority of the value through that organic growth engine over the whole period. And rightly, that's why sponsors are paying so much attention to this when they go through the diligence process. So like these cross-sale revenue synergies, you would attribute that as organic growth at the end of the day? Yeah. For us, once we bring the acquired business in, their producers work across our broader sales organization and bring their specialties to bear. We're based in the Southeast U.S., so we have a lot of folks that focus on agribusiness, tourism, hospitality, habitational, all the things that are demographically similar to where we sit.
10:23and bringing those across geographies, bringing those subject matter experts in to drive cross-sell across all of our lines of business as well as product specialty is really critical. And yeah, we absolutely view that as organic growth. The other big thing is a lot of scrutiny around how well the business is integrated. Obviously, reference or cost synergies, but then I think there's like more to it if, hey, are you just doing some quick cost synergies or is this really integrated and operating as a full unit? That's absolutely right. We have the benefit of being a relatively new platform. So we were able to set the business up for integration day one.
10:58When you look at some of the more mature roll-up strategies that started 10 plus years ago, the play then was multiple arbitrage. Aggregate as much revenue as possible, flip it to the next buyer based on that arm. And today, you're just not seeing that in the market. Being able to prove that integration out. And everyone talks about integration, but what does that really mean for your business? and being able to show those proof points on, obviously there's the expense energy side, but that revenue component that I mentioned is really critical today. And not just getting that push from macro impact in the market, really proving out that there are other levers that you've built around that organic growth engine.
11:37We're going to take that apart in terms of building the system, but I want to first understand your lens on how do you evaluate deals? Before you mentioned that you'll underwrite on four key criterias, which is strategic, financial, operational, and data readiness. Can you walk me through that framework? And then maybe where even the integration thinking fits in. I would add cultural to that criteria. Cultural fit is binary for us. If we can't get past that, we don't move on to the other kind of key criteria from an evaluation standpoint. Because in a people business like ours, that cultural fit is number one.
12:11Once we get past that, integration shows up for us early and often from the pre-LOI process where our integration leader and then our key functional area owners are part of the conversation. They each kind of evaluate particularly the operational and strategic and data readiness piece of those criteria and how that's going to impact their integration. And we integrate 100 % of our acquisitions starting from day of closing and we wrap up virtually all the work streams within the first 90 days. So it's a pretty aggressive timeline. We think that integration makes us better as a whole. And we have a lot of levers internally that focus on building that integration engine so that our folks can get out of that frictional time period right after closing and get back to growing their business and tapping into the broader resource suite that we've built.
13:02So today, as a business, we're closing in on$200 million of revenue. But we have a pretty small and nimble integration team, which means for those criteria, we've got to consider not just getting the transaction closed, but also the impact of the business and our people after the fact. We've passed on deals in the past where we knew that it would be a significant uphill battle around the integration piece. And that was really around our first year at Oak Ridge. You're trying to get your first deal done as a new buyer in the market. But you think about the cost, both direct and indirect, of that difficult and frictional integration processes.
13:39There's a number of what I'd say typical deal pillows for us around the integration piece. Obviously, there's the people aspect. You're dealing with difficult people. But the big two for us are lack of up-to-date technology and then weak data standards. That data readiness is so critical in our business. As an example, we run a pretty robust data model, a single instance of our ERP. any kind of lack of commitment by the seller to move to our data standards for us is a clear red flag on those potential integration issues to come back to us table stakes and if they have an issue with that they're going to have an issue with a lot of the other integration levers that we're going to have to pull during that integration phase there's a lot that goes into this first culture fit then you mentioned that understand the operations and their data readiness and obviously we didn't touch as much on the you know there's a strategic fit of doing the deal and then the financial fit, I guess, as well.
14:30If we took the culture piece, how do you validate that? Is it just purely, I'm at the management team, it feels good? Or is there something more objective to validate the culture fit? Our process is one that I'll say frustrates the investment bankers when we're in one of those processes, because we want multiple meetings with the principals, hopefully the opportunity to meet other folks in the organization that are critical to the go forward business. We almost always do in-person meetings to make sure that we're sitting across the table from someone pre-deal. That kind of comfort naturally evolves the more you get into it, but it does create a longer timeline on the actual transaction.
15:10Historically, about 75 % of our deals have been proprietary. In other words, we've sourced them internally without a third-party intermediary involved. And that's to our benefit, that relationship building aspect where you're not part of a banker auction process. And I used to be a banker, so I understand the value of that process. That sort of homegrown relationship building you can do offline creates a longer deal process, but really leads to a better outcome. And you have very high conviction around the cultural fit, even before you get to the point of signing an LOI. The other thing is 12 deals last year sounds like high volume overall.
15:46There are other buyers in our market that are between 50 and 100 transactions a year. So we think of ourselves a pretty selective buyer. For example, we signed NDAs for 100 potential transactions last year. We only bid on 28 of those and closed 12. So that top of the funnel, making sure that all of those criteria are a good fit for us, starting with culture, is really how we end up with best fit partners for our model. Yeah, that's like a pretty good funnel there because you went from 100 NDA signed, 28 and then ones that you're actually pursued. Pursued means like actually put LOIs or? Yeah, 28 LOIs went out and 12 of those were signed and closed.
16:27So we have a very good track record. Once we get to the point of signing an LOI, we've closed 100 % of those historically. So we are very committed once we get to the LOI signing phase. What percentage of these were banked versus proprietary deals? Last year may have been a few more bank deals in the mix, but overall over the last five years, 75 % are proprietary. And those are stores by myself, our CEO, and then really our partners. Once they come on board, we have a very good track record of generating new partnerships from recent partnerships. I think that speaks to how we treat those partners as they come in, as they work through the integration process, back to that culture and relationship building early on.
17:07That gets them on board sooner. And the other kind of aspect that I should mention is We're not looking for acquisitions where the principals are ready to walk away. Our weighted average shareholder age is high 40s. We are very much focused on folks that want to continue with the business, think about it as a buy-in model, not a sell-out model. And that gets great alignment for that next phase as they come in and access our resources for growth. Yeah. So you got them, even the management team, pretty vested in. What does that look like in terms of those deal structures? Is it rolling over equity?
17:39Is it in earnouts? What does that look like? It's both. We have, I'd say, relatively strong conviction around a minimum of 20 % of the upfront value being an equity consideration. Overall, over the past five years, the average is actually 25%. So 75 cash, 25 % equity upfront. All of our deals also have an earn out component. Three years, again, based on organic growth of the top line after the fact only. So revenue-based earnouts, but again, those are cash and equity. What we like to do, work with the principals, particularly over the earnout period, bringing more folks into that equity ownership pool to make sure that those folks that are the drivers of the value post-closing get to participate in that upside because we think about the business not just as an income and compensation piece, but also this wealth creation opportunity for folks that probably didn't have that at their family-owned, entrepreneur-owned business.
18:34That distributed equity model that drives that growth, we're over 50 % employee-owned in our cap table, and that includes about 250 of our 600 employees. Pretty widely distributed, not just former agency principals. It includes a really broad swath of folks, all the way from back office accounting to service, middle office, and front office production. We think that is really critical to building a long-term business and continuing to perpetuate that weighted average shareholder age downstream. I like that. So you, about 25 % of a deal, rollover equity, and you're actually expanding the equity pool to a larger pool of employees that would otherwise have it.
19:13Yeah, that's right. We've done deals where we brought every single employee that came over in as an equity shareholder. We've done that on a few. Often these businesses, historically, it's hard to move equity in a tax-efficient manner if you're not the owner of the business. So the time of the transaction is a great time to do that. Sharing in that event with the employees and in the earn-out pieces, we see almost 100 % participation in others than just the principles of that seller participating in these earn-outs over that three-year period post-closing. What does the structure look like in earn-out?
19:45What percentage of that purchase price gets allocated on the earn-out? When you look at upfront versus earn-out, now our earn-outs are uncapped. But on average, that's probably 80 % upfront, 20 % of the value in the earn-out. So it's heavy on the upfront, but because of the uncapped nature of the earn-out, we've had a couple deals that were smaller roll-in deals where the earn-out payment was actually larger than the upfront simply because of how much they grew over that three-year period post-closing. They tripled or quadrupled their business, which leads to a very attractive earn-out payment.
20:16So we love paying those. Awesome. Now, there's a lot more to go into, but I want to keep moving here. Sure. The one thing I was curious about is what you've seen in the market. I know we talked a little bit before about just some of the deals and I love hearing about deals. In particular, you've seen situations where like we talked about the trend over the five years where their process actually blew up. Can we talk through some of those deal stories? Yeah, for sure. Both of these were big billion dollar revenue plus organizations, which had been built over the last 10, 12, 15 years. Those processes, when they got into diligence, the key factors that impacted them were lack of what I'll call true integration.
20:52They give lip service through the fact that they're integrated. But when you really peel back the onion, like they're not really that integrated. They're using a data warehouse to pull in data from 15 different ERPs, a bunch of different payroll companies, and just aggregating that up into the corporate lens, which in today's world is not true integration. The other thing that is just kind of this inability to really illustrate the proof points, particularly on what you market the business as to these potential buyers. This is really in the sponsor community, but sponsors are going to do a lot of diligence, 90, 120 days of diligence on a, what is that, a$5 billion transaction.
21:30So when you get that deep into diligence and those proof points don't hold up that you've pushed out to the market, it's something that you're good at. That's what really leads to that broken process and obviously then leads to a bad financial outcome for the shareholders. What we find, and we do this too when we're going through diligence on our side on a much smaller scale, we're going down the diligence list. Each time we uncover something that makes us second-guess the valuation, that makes us look harder at those remaining diligence items that are still open. In some of these cases with these really big platforms, the valuation expectation was so high, that issue list became so long that just buyers stepped away entirely.
22:09And then those businesses ended up being sold to a strategic. Lastly, on that overselling of the upfront when you enter into these processes, the seller has to be really honest about what their organic growth is, how they're driving it. The other thing that we saw with some of these bigger platforms that didn't really get there was they oversold the specialty nature of their business when it's not really there. Don't get me wrong. These are great businesses that obviously got the huge scale, but they were positioned too aggressively, which created this real disconnect between the expectation upfront on valuation and what you would find when you got the diligence and the reality that the buyers found once they got in the hood and the length of time on the deal that will kill a deal more than anything and getting into that deep diligence process and not finding what you expected on those kind of key drivers for a high quality business makes a lot of those processes break down.
23:02So there's definitely how well the company's consolidation play has been integrated and then How are they actually taking a market? Are they like overhyping what the business actually is? What are some of the specific things and diligence that you would find that would get you to really be turned off by the business? Back to our criteria, and I think this is true for the larger sponsors as they've gotten more sophisticated on the market, is really that data piece. What are you doing with your data? This industry has a ton of great data that can be used to push cross-sell, can push your carrier partners on better commission rates, helps you further define your specialties and gain kind of revenue lift from those, take those out to market.
23:41When you peel that back and say, okay, they're not doing any of these kind of basic functions because they don't have control over the data, that's usually the underlying issue. And that leads to a whole host of issues downstream where you're in a diligence process. You can't produce updated monthly results in a timely fashion after month being closed. You can't roll forward any of the data cube or any of the one-time exhibits that you built to take the book to market and put in the data room. So all those factors contribute. You'd be shocked if some of these businesses that are consolidating gap financial reporting on a host of individual spreadsheets at the acquisition level for each of their acquisitions they've done over the past several years.
24:21So when these platforms started, and this was a new game 10 years ago, that was fine. It was revenue aggregation, it was multiple arbitrage. Today, the market has really shifted. It's hard for a platform of that size to catch up. You think about a large, unintegrated platform to get to that full integration standard. To me, that's a big uphill battle. And think about what they sold those early partners on. They sold them on the fact that they would get to continue to run their business. They wouldn't have to integrate. They could maintain their legacy brand, their legacy systems, all of their legacy people, their legacy accounting standards or non-standards in some case.
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24:57Then you suddenly come in and say, okay, sorry, by the way, we're going to fully integrate you in the next 12 months because we have to clean the business up you're just creating this disconnect with that culture that you build on the front end data the big things data you referenced a deal that had like hundreds of excel sheets for their monthly financial reporting i actually heard about a situation where that was one of the things the buyer asked for updated financials and i don't remember the exact it took them like seven ten days to turn around and they walked away they were like this is obviously not integrated yeah there's the easy red flag You can't roll for sort of the basic analyses that you should be using to run the business anyway.
25:35That's a huge red flag for folks is particularly at scale. We're talking about a billion-dollar revenue business. That is a massive organization, and there should be very tight accounting, reporting, management data, KPIs around that business that you're using day-to-day to operate. Those are tough deals to see in the market, knowing that there are high-quality people there. the underlying business was strong, but the lack of integration did not make it feel like a real platform operation. Let's talk about building the machine, the Matt James way to M &A. Let's see. Day one, it was just us and a checkbook for the first year.
26:09Over time, we've built a couple of things into our deal process. To us, it had been a huge advantage really around the people side. Insurance brokers, 90 % of your assets are the people and those customer relationships they bring to the table. The one thing we added, and this is interesting, it came from a conversation we had with one of our operations folks at an acquisition we did during our first year. He came to us after the process. This was a proprietary process. They didn't have a banker involved. And he came and said, you guys could do that a lot better. There was a lot of friction on the closing.
26:43It was a relatively large deal for us. And we took that as him raising his hand to improve the process. So today, he sits in his seat as our VP of new partner operations, and he really quarterbacks everything from that free deal LOI diligence process to 90 days post-closing integration work streams. Unfortunately for him, one of his primary job is managing me out of the process as quickly as possible so that our functional area leads and our internal experts can really start taking ownership of integration even before closing. He follows along, sits alongside me for pre-closing diligence work stream, is on all the calls, has weekly calls on checking in on questions.
27:24And really, it's that seller education piece, which is particularly important around our proprietary deals since they do not have an intermediary walking them through the process. Because remember, these folks are going through a once-in-a-lifetime sell of their business, and they're also trying to run the business simultaneously. So he's really that quarterback and almost a seller advocate as we get up to the closing table. He can then translate that, all of those, the data, the work streams, all of that sort of tribal knowledge that you build as you work through the diligence process through the broader integration group when it's time for them to step in.
27:57So that for us has been huge. What I'll say is about two years ago, we also moved away from the historical Excel tracker sheet to the deal room as our kind of source of truth on the hard data piece. And we think of our VP of new partner ops as our source of truth on all of the qualitative factors and people factors, those nuances come along with wiring a people heavy business like an insurance broker. The combination of those two with our new partner operations team and managing that process has been absolutely huge and just getting new deals onboarded faster and not just onboarded faster, but making them feel good about the decision they made to partner with us versus one of the other 50 plus acquirers out there.
28:42Matt James:join Kisan Patel and Gwen Pope at Master Your Mergers People Synergy Summit on April 21st their closing fireside chat explores why integration models break down after close and what buyer-led execution actually looks like when it's working if you're running acquisitions or responsible for post-close results this is the session to catch register for free at peoplesynergysummit.com. Again, that's peoplesynergysummit.com. We got a lot here to unpack now. So I like it is one is like literally looking at your whole process from LOI through integration as one continuous process. There's gonna be a lot of like buyer led themes over here.
29:26And I like how you brought what you call it the partner operations. New partner operations. New partner operations. Like you literally have a role and a piece of that role is not only optimizing this whole throughput process end to end, but you mentioned the seller education piece. And I'm curious too, because when you mentioned, hey, if it's proprietary deals, it's important because they don't know the process. But I'm like, even if it's like comparing a bank process through proprietary, I feel like a lot of times the bank process just, here, let's optimize for getting the best price or need to close.
29:57But when you mentioned all this activity hinges around how well you can integrate, you got a 90-day timeline that you're targeting to integrate. Is there a piece of that seller education that actually lends more towards the integration or sort of preparing them for integration? Is that part of it or is it more that comes later? No, it's definitely part of it for us. We often, even to the point of even a first meeting we're having with a prospect, we share our integration guide. It's a 50 plus page document that details each component of our integration process, has all the key people that lead those different processes internally for us.
30:30It really just shows the seller what they're up for once they get over the wall through the transaction process. Because we think that transparency and consistent communication about what's going to happen is really the key to making that process smoother. If there's not an unexpected that's coming their way, even if there's things like technology conversion, a lot of people don't love that part of the process. But they know it's coming and have clear visibility and line of sight on what that's going to look like. So we think that level of transparency, in some cases, it probably makes us look a little bit more heavy handed on the integration side.
31:08But again, going back to when you see some of those larger failed processes, like that disconnect between expectation and reality for the seller and what life will be like post-closing. We don't want any kind of daylight between those two concepts. We want to be very transparent with folks as they come over the wall and know what to expect as a part of the Oak Ridge family. That's like the big piece that kind of gives them a lot of heads up of what's to come and get them prepared for it. Anything else? You have the role. They really are basically supporting the whole process. The big thing I always hear about is this fallout between diligence and integration.
31:43Where do you see your ability to bridge that gap? Yeah, I was a primary culprit of that before we had this new partner operations role. But year one, I was focused, heads down, let's get these transactions closed. We need to grow. I would close it, throw it over the wall to our different functional area leads, HR, accounting, marketing, and basically figure it out. That leads to a very inefficient process. Tons of questions come back. Even though we're buying the same type of business every time we do a deal, there are nuances that make these deals look very different. That inefficiency, chaos, all the rework of translating those key diligence information to our broader team, like just way too much of that critical knowledge, that tribal knowledge set only with me and disseminated out to a larger group was really critical for us.
32:32So that evolution of our process, it was a big factor on getting me out of the sole owner of that. But now we're at the size and scale where we have plenty of folks around the deals day to day where everybody has a good sense of what's going on. so we don't have that breakdown post-closing. So it's all about building that continuity, basically, of that whole process. So it's not, things are just completely handed off and disconnected. Yeah, and we have a relatively consistent process, that integration guide combined with our source of truth in deal room. And we use that as a project management tool as well for our different functional area leads.
33:07They understand the process. And none of our folks came from an NA background. Most of them came from one of our partner acquisitions. So they sat in a HR seat or an accounting seat, but they've come in, they've been through a process, they understand it fundamentally, and they are constantly thinking about how to make that better for the next partner that comes over the walls. Somebody that's kind of been burned from the process coming in, put them in that role so that they can help everybody else have a better experience. Yeah, we did that last year. We did a pretty sizable platform deal down in Florida.
33:39They had a great leader on. She wore a lot of hats for them. CFO, COO type role. She's now our new talent partner on the M &A side on our HR team and does a phenomenal job. Just being able to connect with those employees because she's been through the process and understands when she had to translate what was happening down to her employees. They had about 40 employees that came over, relatively large group. And having been through that and then understanding the value proposition of joining our team, she's an amazing connector of bringing those concepts together, particularly when you get down to the non-principles that are really just being drugged along in the deal process.
34:16I like this approach. You mentioned source of truth and deal room. I never heard of deal room. Tell me about it. And what does it do? No, as you know, great, great product. Again, we were managing everything via the old folder Excel sheet. You get an Excel tracker. We have internal one. You'd have one from your third party accounting diligence. You'd have one from your third party legal. We consolidated all that, made it live real time in deal room. We use Deal Room for the entire M &A process, all the way from our prospect pipeline, all the way through post-closing project management checklist.
34:50Those dependencies you can build in around that project management piece has been huge for us. Because again, we have a small team. We're often integrating anywhere between three and five deals at a time. But we're doing 10 or 12 deals a year. That keeps us organized. Again, keeps me out of having to revisit deal terms and things like that. So that source of truth has been huge. And not just as a database for all of the diligence work we've done, all of the contracts, all of that, but really that project management piece for us has helped us take our process to the next level and not have this drawn out, disconnected process between, okay, we're waiting on our database admin team to scrub the data before our IT team can go in.
35:31All that now is very seamless because of having these dependencies in the system and having our new partner operations lead really manage that as quarterbacking that process. You're getting rid of the series of trackers that you had and you get rid of that. You have it all in one system, which acts as your single source of truth, and you can track your dependencies, keep things better organized. And essentially, you run it end to end. I guess part of the thing is you're also managing the integration here as well. Yeah, absolutely. The integration process for us to get all of the kind of functional area items, they're done by 90 days in, but still making sure we maintain that database and source on what we bought to understand how that's evolved after the fact.
36:13That's a great way to go revisit two years, three years down the road, particularly when they're through their earn-out period, and just understand how that business performed based on what you underwrote at the time. And early on, you could just think back on the thesis around underwriting these individual deals. But with 60 deals that we've closed, you lose track now of what the thesis was at the time, three or four years after the fact. Yeah. So you got this basically archive that you can reference this data back at any point in time. When it comes to scalability, obviously, tech and software is a piece of it.
36:44Is there anything else beyond the tech that really helps when you're running these concurrent deals at different stages? The tech piece was huge for us is getting out of email and emailing spreadsheets around. That was our weak point with our team overall. The other piece is a little more qualitative, but that view on being really transparent with the seller on the whole process. And we have the advantage on all of our proprietary deals because we are walking them through the process a little bit as their advisor at the same time being the buyer. That transparency, clarity on timing, on what the key gating items are, all of that project management for the deal process and constant communication.
37:25One thing we did about 18 months ago for all deals that are in flight, which means post LOI, our VP of new partner operations has weekly calls. It might be a five-minute call some weeks. It might be a 30-minute call, depending on where we are in the process. but that constant and consistent touch point where the seller sees the same people, same faces every week, and has the opportunity to ask questions in that forum. We feel like that transparency and visibility straight into our team has really built just a lot of goodwill with new partners as they come in. That's a key part, really over-communicating, building those relationships, making sure it's a good experience for incoming team members.
38:05The other piece of the tech you mentioned, we looked at integration, is like how well the data is put together. And one of the things you invested a significant amount is building a data lake so you can have real-time dashboards. Can we talk through that? Because I feel like that's another big piece. We talked through your process flow and tech on the execution side, but then what are the things that ultimately land that allows us to be a valuable asset when things are said and done? A couple of things there. One is part of the integration process. We move everyone to single instance of our ERP, even if they're on a different instance of the same system.
38:39We move everybody over. Our database admin team scrubs the data before it comes into our environment. What does that tech stack look like? What GRP system do you guys use? So we use it specific to insurance brokerage called Applied Epic. There's really two big competitors there. Every industry. Applied Epic. Call it a customer record system. It tracks revenue and commission. That tech, it's built off of an older platform. So we have to then pull that out. We've got Databricks on the back end for our warehouse build. And then we pull that through Power BI from Microsoft shop. So we pull that through Power BI.
39:11And what that's done for us, and this project kicked off about two years ago when our new sponsor, Audax, came in. One, they were very supportive of wanting to get through this initiative on the build of this data platform. And we already had the fundamentals where since day one, we were already integrating and moving everyone to our native ERP so that the data was pretty clean. This was just taking that data to the next level, bringing in other dimensions around payroll, around market data, around data from our carrier partners on pricing and things like that. Overall, that has transformed the business from being more reactive to much more proactive.
39:51That's what you really want to get out of this data analytics build platform. Whether it's the revenue side of the house, expense side of the house, that data and dashboards allows our key leaders in the organization to self-service, whether let's say they're a regional leader, they can self-service their own P &Ls, understand their employee metrics, understand their productivity, their organic growth, down it all the way to the individual branch level. And then right now we're pushing through the ability to look at individual producer level. There's a lot of granular data there where it's just so much easier to go find the low-hanging fruit.
40:27And then when there's an issue, there's a headwind in the business, we can immediately go and look at the analytics package and understand where to go look to uncover those issues as we're running the business. So it's been huge for us. The spend always sounds high, particularly when you're sponsor-backed. But I think the risk today of not doing that is future evaluation degradation versus that cash spend today. How do you enable that? I feel like you're doing a lot of system changes. You've got different leaders across organizations spread out regionally, getting them thinking about the same way of utilizing this data.
41:01I feel like I've been in businesses where you struggle with it. You invest and you get the system there, but then the people and how they use it, it's a whole other thing. That's true. I mean, one, we have a great group of folks that are culturally aligned. So back to that cultural piece, if you have that cultural alignment day one, that makes the buy-in easier. We also have the distinct benefit of being majority employee on, meaning which includes ownership for all of our key leaders, whether they be at the region, at the corporate level, in our functional areas in the field. And that alignment through our distributed equity model allows our leaders to, we often ask them to put on their shareholder hat and approach those business decisions, particularly with their tough business decisions, through both the lens of the shareholder and the P &L owner.
41:44And that creates great buy-in and sometimes a little bit of competition among different regions too to drive those metrics. So that distributed equity model is really fundamental to our DNA. It resonates with everything we do and helps create that buy-in with that shareholder mindset versus a push down from the corporate level trying to hit these targets with no context. We don't take that approach of top-down management style. What would you say are the most valuable KPIs for an acquired business? For us, it's the revenue per employee right now. That speaks to efficiency. It also speaks to their ability to scale.
42:20If you look at historical revenue per employee over the last five years, have they been able to scale with a smaller employee base? Are they implementing technology? How are they managing those costs in the business? So to us, that is the headline KPI that we're always looking at. We don't have all the data integrated. And then from there, it's a very granular breakdown of revenue, expense, people, metrics, kind of everything across the board. But that revenue per employee for us is critical. Big emphasis on data. Make sure you get the data integrated. That's the key part. It sounds like the rest isn't that bad.
42:52You follow through. Obviously, there's a people aspect, which you structure the deal for a lot of the retention. You're giving them equity. So you got alignment with the people. You got the data in place so that everybody's on the same page the way we look at the numbers and build our goals around it. Yeah, I feel like if you lead with culture and get the culture aligned, you'll get buy-in around the data piece. From there, everything else is just execution. Culture first, and then making sure that the data can come over in a way that's useful to the broader businesses is our kind of two key focus areas when we're thinking about the integration lens.
43:25Give me some stuff, I don't know. I'm just wondering like the things that you learned in terms of surprises that come out after close or the hidden operational issues that you find out the hard way. Teach me that stuff. There's such a wide spectrum of things that you would be like, I would have sworn we should have covered that during the diligence process. It's headwinds that are macro in nature. For example, right now in our business, great news as a consumer of insurance, but there were no big hurricanes, no big cat events last year. So pricing is soft. That means we feel the pressure on revenue there.
44:00So that puts more emphasis on that new business engine, that organic growth piece for 2026. That's part of the normal cycle. But understanding where that is across the different pockets of the business. The thing that always surprises me the most when we have a new partner coming over is just the level of buy-in that we get from the non-equity holders. You think about all the friction that's created for that employee that sits at the desk level. Their day is getting more complicated. They have to learn a new system as they come over into our environment. They have higher data standards. But being able to really show them the path on why that's going to lead to a better outcome for them long term and then really educate them on what it means to be part of our business.
44:45We get such great feedback and buy-in from a lot of our folks after the fact on that. That's always surprising to me because they're not receiving any economics from the deal. That near-term friction is pretty high for them. But six months down the road, we have a lot of folks come back and say, my opportunities from a career pathing standpoint, the level of professional development that we get as a part of a larger organization, the ability to work across multiple geographies and offices, all that leads to really strong culture building for us. Big and best big on culture. You mentioned earlier, a lot of your deals come from acquired businesses.
45:20Tell me more about that. Like, how do you build pipeline that way? Yeah, so. Good, healthy or proprietary deals, baby. That's what we want. So yeah, you get one of these banker processes and you're one of 20 bidders, it feels like. And they are certainly driving price. That is the main goal. I don't like doing all the work with uncertainty that you're going to get a deal out of it. I hate that part. Back to that sort of employee experience and experience that we try to build for the sellers on our proprietary deals. That makes them feel really good early on about their choice as a partner. Look, there's 50 private equity backfires in our space.
45:56and then another handful of publicly traded and kind of private buyers. So let's say 60 buyers total. Anybody can sell their business to anybody in the market anytime and get that market clearing price and value for the business. We want that experience to be high quality for them. They're incentivized and thinking about coming over day one as a part of the organization and really buying into what we're building. A couple of things maybe that helps us build that referral engine with recent acquisitions. One, and this has been more recent in the last two years, but bringing that VP of new partner operations in has been a huge upgrade on the process, which makes those sellers more confident on our capabilities, just supporting their transaction process and seeing what it's like and that transparency I talked about.
46:43So that gives them confidence that they have a friendly competitor, somebody in another geography that they would recommend to us. That's something that's been huge. Again, high degree of transparency and that communication and education piece on what's going to happen, being honest about the things that will change. That's built really strong connectivity with those sellers. And then finally, and this is back to my last comment, is treating those new partners and their employees with respect as those folks are our greatest asset in the business. We don't feel we can ever be too high touch with employee onboarding, on-site visits.
47:16We often take the entire C-suite for on-site visits, being super responsive as we lead up to closing. It puts a big burden on the executive team and our new talent onboarding folks. But we think that leads faster adoption, stronger buy-in. Those sellers really pick the right partner. It also helps that we have economic incentives for those folks that bring new deals to the table. What does that look like? Is it like a percentage, a kicker? Yeah, a percentage of acquired revenue up to 2%. So it can be meaningful. Not bad. Yeah, it can be meaningful for the larger deals. the challenge in our space is almost any deal over 5 million of revenue has a banker behind it those are hard to find fair enough i know what to do in my spare time now i'm going for you in marketing they would call this matt a flywheel you really nail the customer experience and they go out and they do like word of mouth and then it comes back it's been interesting to watch the first couple years we were out pounding the pavement on telling the story we were a new acquire.
48:15There's all this competition out there that at a 10 ,000 foot level looks very similar to what we're trying to build. As we've gotten more mature, as people have gotten to know us better. The other thing that helps is we're very geographically concentrated. So we're only in eight states in the Southeast. So building that brand value, building that knowledge base for potential new partners, we've seen a lot more inbound interest than we have ever have in the last 12 months. So that's been really helpful in filling that top into the pipeline too. All right. So a little more personal here, but you're the CFO and the chief acquisition officers.
48:48And I know most platforms would separate those roles. Is it because you guys just adopted AI and they make you do all those things? What's the reason for rationale behind that? I'd say day one, it was just, hey, do we want to spend the money on this new startup? We were all wearing a lot of hats. You've been in the startup world. You understand what that looks like. As the business has evolved, it's certainly gotten more challenging. But the interesting thing is M &A and that CFO seat, if you're a strategic CFO, I'm certainly not an accounting person by trade. It's pretty closely connected. I think that CFO seat has really become increasingly strategic as a position over the last several years.
49:25When you think about how that integrates with M &A, it really puts, one, a spotlight on the financial and economic piece of the evaluation criteria as you're underwriting. Also helps have that more broad and earnest view when you're speaking to the potential sellers. I'm often at the first meeting along with our CEO for many of these acquisition targets, which having my CFO title first, people might think that's a little bit odd. But when you think of it in the sense of that corporate development function, it makes a lot more sense. Maybe the other advantage that I have for running M &A is the benefit of being a part of Oak Ridge since our founding.
50:00I'm employee number one. That unique perspective really helps me speak more intelligently about the challenges of building the business to where we are today. all the issues we've solved for on the operations side. And then also just highlighting folks where we're not as fully developed, what we still need to work on is sellers do their reverse diligence on us. So today it's still doable. It feels like there's a lot of advantages to sitting in both seats. But as we scale, we've had to build a lot of folks underneath me on the accounting side, for sure. We have a 20-person accounting department that handles all of the reporting and all that stuff.
50:34It's interesting, though. Can you just give me purely the CFO cap and help me think through the way you would think financially? I feel like, and we talked about this before, of doing acquisitions. There's obviously the deal structure we already touched on. But then what does that impact make on business valuation, share price? And how do you even think through that as a privately held company? The advantage of wearing both hats is, as a corporate development officer, you're very focused on deal count, acquired revenue, growing the overall business. The perspective you bring from the CFO seat is a little bit more measured on what the impact of that capital outlay looks like relative to the other options.
51:17It's always about capital allocation. Where do you spend that money? Is it on acquisition? Is it on development of new technology, new training programs internally? Do we go organically hire a bunch of new producers and see how they fare? So that perspective on not just purely the M &A lens, thinking about what that does to the overall business and what levers we have to drive shareholder value. Like I said earlier, there's just not a lot of multiple arbitrage anymore. So when we go into a modeling exercise around M &A, we're not really building in that much multiple arbitrage. It's all about organic, about how the selling business, how they can tap into our existing platform and our resources for that cross-sell that we talked about.
52:00what other levers can we pull on the revenue side around? Maybe we have better carrier contracts than they do due to our scale. Maybe we can better serve some of their employee benefits customers with some of the resources we've already built out. So that perspective is less focused on the pure M &A volume lens and more about how M &A fits into the overall growth strategy of the business. Thinking big picture, baby. Okay, so this is where we got to summarize some of our lessons that we talked through. Let's say hypothetically, Oak Ridge had a big exit. You cashed out, but you're still motivated to do something else.
52:35And I bring you in and said, hey, Matt, here's this rollout that I found that's already at a good pace doing, let's say, six plus deals a year, but they're truly operating like a revenue aggregator. I'm putting you there in charge. Same role, CFO, Chief Acquisition Officer. What would be the first thing that you would change? Number one, clean up your data. Clean up your data, get your techs back in order. Would you pause, though, doing deals to go back and do that? I would. And we've seen some of those larger acquirers do that. A couple of years ago, there was one that really shut down their whole M &A function for, I'm going to say, 12 to 18 months and solely focused on integration, including that transition of the data, the system, the people, the brands of all the legacy businesses they acquired.
53:21So yeah, I would hit the pause button on that and get the house in order. Those parameters you gave, it's not so big that at that stage that you can't clean it up in a quarterly fashion. The bigger you get, though, the more difficult that becomes, particularly if you don't have geographic concentration, you've got a lot of small offices out in the field. That cleanup process has to happen, particularly before you go out to market for either a recap or a sell process. That lack of ability to provide proof points is such a big differentiator as part of that diligence. I would put that behind, probably second behind organic growth as driver of overall value.
53:56Can you validate these proof points on your investment thesis? The sooner you get done with that hard work of integrating, I think the better position you'll be to sell the story to the next buyer. I would do it day one, come in, get the data cleaned up, get the tech stack in order, get everybody rowing in the same direction from that perspective. Our business is so data heavy. It's clear if you're not working down that path today. I would agree. And I'd say pretty much every business nowadays is very data heavy. Any other takeaways, things you've learned over the years? Like I said early on, I didn't come into M &A intentionally, but got a taste of it in my first role.
54:34And just really love the dynamic nature of it. Anyone that is thinking about a career at M &A, whether it's on the corporate development side, on the integration side, it's super dynamic and something that really engages you day to day. I'm planning on staying in the space for quite a while. Hey, James, this has been good. I got to ask you before we wrap up here, what's the craziest thing you've seen in M &A? Oh, craziest thing. There's nothing that beats this. We were doing a diligence engagement when I was a buy-side banker on a deal. We were advising a big strategic. They were looking at a second acquisition, going through diligence, tying out the tax returns of the seller and all this work.
55:11The seller was deducting their mortgage at their house under the argument that they parked their work vehicle there. So it was really a parking expense. So there was this line item of parking expense that was several thousand dollars a month that was his mortgage payment. So we opted out of that deal. Let's put it that way. Wow. Very aggressive tax position. Wow. And the fact that killed the deal. It killed the deal indirectly. That makes you question the quality of the people you're partnering with. Well, and it goes back to that thing where it's like you get one red file, so you're putting way more scrutiny on everything else.
55:45Yeah. How you operate. Yeah. Without that, that deal would have probably died anyway. but that definitely put it over the edge. That was an interesting call to make. Hey, this has been a great conversation, Matt. I appreciate you taking the time, school of me, helping me become a better M &A scientist. I appreciate it. I love the conversation and appreciate being asked to join today. So thanks so much for having me. Those of you still tuned in, my fellow M &A scientists, I'd love to hear from you. I'd love to hear feedback, what you thought about this podcast. If you got ideas for topics that we haven't covered yet, if you got some feedback and criticism for me, I'll welcome, take it.
56:19I'm always trying to improve and get better. Feel free to reach out to me on LinkedIn. I got my filter thing down, so I get a bunch of spam. So make a comment and say, hey, I listen to the podcast, so I know you're an actual listener and not just somebody that's going to pitch me another service that we don't need. Until next time, here's to the deal.
56:48Thank you for taking the time to explore the world of M &A with our podcast. We love hearing feedback. Tag us on a LinkedIn post, add a review on Apple Podcasts. We'd love to hear from you. If you need help standing up an M &A function or optimizing one that you already have, we're here to help. And if we can't help you, we probably know someone that can. You can reach out to me by email, Kisan, K-I-S-O-N, at mascience.com. or you can text me directly at 312-857-3711. If you just want to keep learning at your own pace, visit mascience.com for a lot more content and resources. That's where you can also subscribe to our newsletter.
57:32Again, that's mascience.com. Here's to the deal.
58:01Thank you.
From the publisher
Matt James, EVP, CFO & Chief Acquisition Officer at Oakbridge Insurance
Roll-up platforms that skipped real integration are getting exposed when they go to market. Buyers want proof of organic growth, clean data, and a platform that actually functions as one. A lot of processes are breaking down because those proof points aren't there.
Matt James co-founded Oakbridge Insurance in 2020 and has since closed 60+ acquisitions, integrating 100% from day of close. This conversation covers how he built that system, what went wrong with billion-dollar competitors, and what he would fix first if he walked into a revenue-aggregating roll-up right now.
What You'll Learn
- Why multiple arbitrage is gone, and what buyers are scrutinizing instead
- How Oakbridge evaluates cultural fit before any financial criteria
- What a failed billion-dollar roll-up sale process looks like from the inside
- Building integration continuity from LOI through 90 days post-close
- How distributed equity drives buy-in across an acquired organization
If you're evaluating targets and want to know if they're integration-ready pre-LOI, the Intelligence Hub can help you score cultural fit, data readiness, and technology maturity. Join the professional membership at mascience.com/membership.
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This episode is sponsored by DealRoom
DealRoom's State of M&A Report gives you data to back up your M&A priorities.
The State of M&A Report reveals the gap between what teams think matters and where the real bottlenecks are.
Download it now to get expert insights: https://hubs.ly/Q03ZxRvD0
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Episode Chapters
[00:03:00] Introduction & Matt's Background
[00:05:00] How Buyer Diligence Has Shifted
[00:06:00] Organic vs. Inorganic Growth and Why It Matters
[00:11:00] The Four-Criteria Deal Evaluation Framework
[00:14:00] Validating Cultural Fit Before LOI
[00:17:00] Deal Structure: Equity, Earnouts, and Alignment
[00:20:00] What Billion-Dollar Platforms Got Wrong
[00:26:00]Building the Integration System at Oakbridge
[00:31:00] Bridging Diligence and Integration
[00:38:00] Data Infrastructure: Databricks, Power BI, and Why It's Worth It
[00:45:00] Building Proprietary Deal Flow
[00:52:00] First Moves When Integration Is Broken
