YouSaid · the spoken record

Josh Koplewicz

lines on the record: 66
first: 2025-06-12
most recent: 2025-06-12
sittings or episodes: 1
sources: podcast

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“Think the chapter is about bringing our firm dagger streets to a different level of driving impact and helping portfolio companies. I'm excited that we dialed in a really specific model for investing and a model for helping portfolio companies. And we just want to do more of it. There's been a lot of phenomenal learnings. And I think this is a great moment in time for us to put in an action in an even more material light.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Of desire to operate at the most excellent standard all the time while being professional, that at least the people around me exuded and just a drive to be consistently great that has stuck with me. And that was an approach to everything, whether it was communication externally, underwriting, or other business or software activities, it was real and it stuck with me.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Say first one, even though he doesn't work in private equity, let alone finance, probably my dad. He's a doctor. He's run and grown departments inside different hospital systems and then also independent organizations. The energy enthusiasm he has towards growing teams and the sense of satisfaction and reward he's had to driving impact around building an organization and seeing that business grow was and has always been inspiring. I see parallels to that when things go right with the companies we invest in. The other one is probably, this is a bit of a cheat, but it's probably no one person, but it's different elements and attributes of some of my colleagues at Goldman. So there was just a level.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Lots of traditional small jobs, babysitting, fixing computers, any little side hustle. My first paid job was actually being a style and marketing consultant for Levi Strauss when I was 11. A stranger heard me talking and recruited me to do this job. And for about two years, I got assignments from Levi's Strauss company to basically give them my opinion on lots of different ideas they put in front of me. Actually, the New York Times wrote a story about how it was child exploitation. I thought it was the greatest thing ever. I guess what I learned from it was even people who are experts and are possibly the best at what they do only know so much. I sit around a table with all these adults. I thought obviously had all the answers. And it was crazy to me that they didn't know everything.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“A reform. Hip hop DJ, my favorite hobby is probably going to concerts. Second favorite hobby is after being injured in almost every other sport is hiking. It's one of the last sports I can do that are doctor approved and I've become a pretty avid hiker over the last five or six years.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Going to grow and evolve at a faster rate than our business can accommodate. My view is life is long, business relationships are going to continue to evolve and exist while someone might be a member of our team and even after. Oftentimes we'll have junior and mid-level people that work with us. They're phenomenal contributors. And we find ways to continue to work with them outside the firm. We've even done deals with former employees. And so continuing that business relationship is not only the right thing to do, but it's accretive from a business perspective. Fortunately, our core senior team has continued to work together for the last many years. And I think that's going to stay consistent for the foreseeable future.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Employees up and down our team are participants in Carrie or Synthetic Carrie, every single person on our team. One of the challenges sometimes LPs comp our approach to this to larger firms, which I don't think is fair or analogous. In an ideal world, everyone who joined us would evolve and grow with the company and be here for the next 20 years. I think the reality is given we're intentionally trying to stay small and focus on small, there's just a limit to how much our management company and team is going to grow. And so there are often dynamics where certain professionals, investment, or otherwise”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“It's something we think about constantly. It's definitely not as straightforward, and there isn't the clear analog to copy from. I think the way we've tended to do it. Is finding people from the get go excited to be involved with companies and get the benefit of their growth, both directly and indirectly.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“In short, we want to keep doing what we're doing, started the business with the intent of investing in lower mid market companies. It's just as fun. And I think we can add more impact today than we can before with all the learnings, focused on continuing to do it in an even more dialed in manner. Our funds may grow a little bit. We have a pretty material co-invest component to what we do. So that co-invest allows us to keep funding capital into companies that grow over a long haul. the idea of sticking with our portfolio companies over a longer horizon is interesting and something that's top of mind to us i think this pocket of the market and being a flexible capital provider is actually more interesting today than it was several years ago and our teams even better at executing at it today than before so want to do a little more and continue refine the model”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“That our returns are going to asymptote closer to that structured minimum return level versus the base or the upside case that hasn't happened historically because the themes have played out and enough of the companies have executed, but it wouldn't be a calamitous outcome. Be it returns that are equivalent to the S&P, historical returns in that case.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“I'd say something that's not specific to the strategy at all is just general liquidity in the market, as uncorrelated as the underlying businesses are and business models are. If we hit patches of pullbacks and liquidity, we're going to hold portfolio companies longer, have an IRR impact. Hopefully there'll be a commensurate MOIC increase. But I think that's a big risk. I think most of the risks, though, candidly is idiosyncratic execution risk. There are a lot of benefits from evaluation and potential for efficiency perspective in these smaller businesses. And obviously the capital structure positioning benefit is huge, but it's the underlying small business execution risk, which I think is really more idiosyncratic and case by case. And so in that situation, if we were unfortunate, that might mean”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“LTV and detaching at 60 to 80% LTV. So really upper to middle of the capital structure type blended risk. But we want sufficient optionality across the portfolio so that we can hope to generate returns that are north of a three or four X gross. So blend those all together in a base case maybe that looks like we're an outcome of 3x or more.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“The shape of underlying deals could be a little idiosyncratic. But when we think about our funds, they are, call it plus or minus 10 positions historically, maybe even closer to 12. Maybe we only have 10 or less outstanding at a given time. We have a high degree of recycling in our approach. So the way we think about it is plus or minus 10% positions at a max, one, two even though some deals may be a preferred note with warrants or a convertible preferred or totally unlevered vertical strip of the capital structure. When you blend those all together, we want something where in a downside case you have a structured return that'll be meaningful. It could generate in and of itself a low to mid teens return where our risk exposure looks and feels like attaching at 10 to 20.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Companies and another way we stand out was just flexibility and creativity around how we structure our deals. Someone who wants to minimize dilution but doesn't want the cash pay burden or restrictiveness of traditional private credit and they want to retain usually materially more upside than they would in a lower mid-market buyout deal. And then it's really about demonstrating our knowledge and potential value add.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“The good news is we're not doing tens or hundreds of deals a year. So a busy year is one we're probably doing five deals or so that would be a high volume year. I think generally it comes back down to we want to find companies where we have a reason to exist in the capital structure. We have a reason to exist because we have a lot of intelligence in the specific sub-industry the business is in and or we can be an accelerant to some vector of that company's growth. In many cases it's a repeat of some analog that we experience at a prior portfolio company. The way we compete is a fun interesting businesses and themes we like where it has that overlap. There are a lot of situations where investing in new companies that have slight adjacencies to historical wins or existing portfolio.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“We're trying to identify companies up front where that's going to match with our skill set. Usually after you're through the first one or two year mark, the scaling risk drops down dramatically, at least in our experience.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“We're investing in. Some of them are former CEOs and CROs of portfolio companies. We've had a number of them are functional experts. We have guys that have led businesses in vertical software and in the real estate space, roll-ups of very small silver tsunami type mom and pop businesses. We have some functional experts that lead or run HR and recruiting firms or have done operational either turnarounds or strategy repositionings both at a small level and some at the highest level with much larger farms than us. So the idea is in the first year of an investment, we're collaborating with management to really come up with a plan and execute on that plan to fortify what we think are the biggest risk areas or the parts of the business that we think are going to come under the most pressure.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Upfront, we're going to work with a company in a few different areas. One is HR and recruiting and team building. Another one is finance, infrastructure, and data. And then the third is around process, procedure, and redundancy in terms of M&A and M&A integration. Those are the three areas where we add the most value. And again, we're trying to invest in businesses that have a good thing going. We're not doing turnarounds. We're not doing repositionings. And if it's really dramatic a shift, that's a case where either hopefully in a really collaborative way, we're finding an exit strategy pretty quickly. So just dialing back to those few areas, the folks helping in those cases are a combination of our investment team as well as our operating partners. We have just shy of 10 operating partners. And these are guys that, for the most part, are former executives in the industry.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Those situations were collaborating with them in most cases to get off the train, so to speak, a little earlier than intended. The good news is usually there's 10, 20, 30 other layers, many of whom are larger, that want these customers. And the customer relationships are so sticky. These are businesses occurring with 90 plus percent recurrence. We can still generate a lot of value on an exit or on an early sale to a competitor, to a larger strategic, or even a sponsor-backed business, even if it's not the ultimate outcome that we at all hope for.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“It's all about execution. So the thing that happens most consistently when things go wrong is companies scaling nicely. The company goes from 30 employees to 100. And there is a new set of management issues. Layers of the org chart. An executive that's used to having control or being in the weeds in certain activities just doesn't have the time or bandwidth. And if they do, it's a totally bad ROI on their time. The growing pains of going from a small business or non-institutionally backed business or a moderately growing business to a slightly faster growing business, that's where we see hiccups. Most of the time, it's just part of the game and it's not a straight line, but hopefully it's a oscillating line that's still up to the right. And in some cases, teams can't handle it.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Good question. So just to back up, in most cases we feel we're investing in pretty obvious themes. They're not necessarily obvious front cover of the times or journal obvious, but if you're a student of some of these industries, they're relatively obvious. And if you're investing in These segments on the smaller end, and they're buying smaller businesses, you're usually able to get a little bit of a discount on valuation, not insane discount, but a little bit of a discount. And there's room to drive efficiency, either on the top line or the bottom line.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“A little more or a little less than half of a company, but we'll do it initially through some sort of preferred security where we're paid back. Win for us was we're creating these securities at a debt like level. The win for the seller or entrepreneur is we can be a little more flexible on valuation and they can preserve more ownership versus doing a conventional bio deal where they may only retain another 10-20% of the upside on the go forward. The kicker on that was after we do that deal We were around the table to help them execute on a handful of M&A transactions. And we had more money that we could put behind that if needed. Those are great because most of our capital was going to things that are making the business worth more. The operator super bullish on their business and they want to roll up their sleeves and accelerate it more. And we can offer our investors this really interesting risk adjusted security where if we kill it, they can make close to the returns.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Other type of example is a case where we've invested in a recurring revenue business where the entrepreneur is very averse to debt. They want every dollar of EBITDA or cash flow that they're generating to make investments in the business. And for whatever reason, they did not want to lever up their company. They also felt that they could grow substantially more. At the same time, they knew they could grow at an accelerated pace if they had assistance with M&A. So buying a couple of their peers, competitors, or smaller versions of themselves that they knew would be instantly accretive if their customers were on their books. As a creative way to stair step into that investment, we've done a number of deals where we will buy either”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Business was able to execute relatively consistently with management's plan. The big picture thesis was a really strong one. When you have people that live in multifamily buildings want to pay their rent electronically and the world was moving electronic and this is an area that lagged and like most of our investments, it's not about the theme. It's really about the execution on the theme. And they were able to execute. So that company grew probably 4x in terms of top line revenue and another closer to five or six x in terms of gross processing volume over a four-year period ended up getting bought. We took some stock. We thought there was a lot more to go. So we took a little stock in the acquirer and then the acquirer got bought. So everyone was happy.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“We were very confident they'd grown materially. Their view was that the company hadn't grown within three or four years, they would want to sell it anyway. And on our side, we had a security where either heads, we make 1.8 times our money over four years. So a mid-teens IRR and our break-even point was really we were investing in, we were around 20, 25% LTV of the company if you were to do the debt equivalent and tails we don't 20 to 25% of the company. And we could make five, six times our money if it hit numbers half of what the management we're projecting. That was a great win-win. They were able to get a deal from us that was way less dilutive than the other offers that they were getting. And we had a really interesting security where it fell in place just in line with those portfolio objectives.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Liquidity and tangible net worth as required by some of their processing bank farmers. So what we did was an interesting structured deal. There were also dilution sensitive. So their view was their company was worth X. We thought if we had to sell the company tomorrow is worth 80% of X, we basically went to them and said, hey, if the company does not grow materially, we have to have some way we can make a respectable return. We'll meet your valuation, but we get our money back first before anyone else. We get a block on any debt. You can't lever the company. And we get another 0.8 times our money. And if the company doesn't grow materially in the next four years, we can exercise our right and we'll agree. We'll put the company up for sale. And so.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Two examples. One is we invested in a variant payments and invoice and company. They did payments in the real estate and property management space, which is heavily regulated around tenant protection. So historically, about 90% of landlords did not offer an electronic option. You had to pay by check. And there was a whole antiquated way of collecting and cashing checks so landlords could stay on the right side of tenant protection and tenant infection laws. We have thesis in this. We went through our whole playbook. Stars aligned several years after building a relationship. And one company that we thought was great needed more capital. They didn't want to sell control. They were approached constantly by smaller private equity players. And they couldn't take on debt because one of the reasons they need more capital is they need to have substantially high.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Depends on the deal. There are some deals that are minority deals where we'll be senior preferred, will have all protections around debt major actions, budget approval, et cetera. And even though that minimum return is on an accrued basis, on an exit liquidation event or some other form of liquidity, we're going to end up earning just based on that minimum return something that's equivalent or materially in access to where a conventional private lender is earning. And in fact, we're going to have a more efficient and faster means to protect against adverse scenarios than a lender might who can't be on the board and can't have certain consent around the table and can't step in and help when things go awry because they're worried about lender liability and shows.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“We actually get back our basis if things don't work out. So if the business is not growing, how can we create a return? Was it through liquidating hard assets? Is it running off cash flow streams? Is it selling subscribers or customers that are easily portable to a third party? Is it a business that we know there are 20 strategics in the mid-market or large cap that already want to buy it and we can pass things over to them?”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Case where a company doesn't do as well. We're buying businesses at relatively reasonable valuations or investing in them at reasonable valuations. But if you have multiple compression or more typically the company just doesn't execute to the extent they plan on executing, there's some sort of hedge in us not having dead money on that return. So across our portfolio today, we have just shy of a 1.5x minimum return. We're trying to create this base layer where if none of the companies grow, they just stay stable, which is rare. You know, we're already engineering, call it a 10, 12, 14% IRR. Obviously, that is not what we're setting out to do. Many of our companies do three, five, seven X, but we're trying to create that downside risk mitigation. And then finally, we're going to think about how”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Every single deal is different. Big caveat the way we think about setting this up is across our fund, we're trying to create a portfolio where the majority of our capital at risk from an underwriting basis is within the credit envelope. So if it were a different portfolio and a lender looked at it, they would say, hey, 80% of these dollars are dollars I would take risk exposure in a loan. The second from a portfolio approach is We want to create some sort of minimum return. Again, not every deal has it, but some sort of minimum return. So on a blended basis across our portfolio.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“But it's a very micro at that point. And as a result, even though sometimes these companies are not totally prepared, they don't have a banker. They haven't done that prep work. We may be able to make the closing process pretty efficient because we're just focused on the confirmatory stuff.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Specific company, we're going to spend a lot of time getting to know folks. So there's a lot of dating before there's a proposal. And it's outside of a process. In some cases, it could be years of dinners, lunches, golfs. I don't golf. Other people in my team might be golfing, referring clients, comparing notes, helping them iterate on a comp plan. observing how the teams act through thick and thin, getting them to know us in our style. And so at the time when we're arriving at a transaction, it's really a conversation about structure and price. After that, it's all about confirmatory divergence. So doing the Q of E background checks, reference checks, even though we've probably already referenced the business, really getting into legal tax and regulatory delay.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Diligence process starts a lot earlier than the identification of a deal. Usually when we've struck a deal with someone or found a company that's ready to go, 80% of our diligence is done. We may not have a view on that specific company. Usually that company is one of many. And we want to have a view on that exact business model, its subsector, and the broader ecosystem well in advance. Quarterly, we're doing deep dives on themes we want to invest in. And that research turns into a multi-year research project where we're tracking those companies following them up, scoring them in our CRM, really dialing in a thesis. Once we've identified the companies we like, and in some cases it may be identifying the teams that we want to back running a consolidation play in an industry we like. There isn't a”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Businesses into a consolidating business. And that company can get the benefit of all the contemporary tools that everyone in private equity is talking about, software, AI, machine learning, but small little gains on those companies on that scale can drive really material outcomes. So that's the overall setup, provide very flexible capital that's not buyout, that's not super levered, and partner with folks to get exposure to those areas.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“You have to maintain your elevator elevator regulation only increases every year regardless of who's in office. Elements of property management, property management is 90% fragmented and owned by individual owners. So these are companies that are small, mid-size, and you have a dramatic number of these companies that are changing hands in the U.S. today. So 70 plus million baby boomers own shy of 50% of the small businesses. And a lot of them are retiring and don't have a succession plan. So we're trying to find businesses that we can back or consolidate alongside management teams that have crazy high recurring revenues that are super resilient and they can grow by buying customers from folks that are retiring or they can be the recipient. Sellers can contribute their”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“20% of the players, they were investing at a very large funds. That market continues to consolidate. And the focus of most folks in direct lending and private credit is on opportunities that are larger than 50 million dollar checks. It's 100 plus million dollar allocations. So you have this piece of the market somewhere between $5 and $50 million that is not efficiently served in terms of flexible debt. So that's one. I think the second is you have this array of fragmented high recurring businesses and examples of some of these business models that we've invested in are sleepy license maintenance software companies that provide some sort of essential solution. Vertical payments companies that are very specified for a specific industry and they have a ton of tailwinds because of regulation. Elevator mean that's super regulated business.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“There's kind of micro themes within each of the sectors that we're hitting on. Big picture right now, I think, structured equity or flexible capital is really interesting in our part of the market for a few different reasons. The setup is intriguing because on one hand, in terms of credit, you see this tail of two cities. You see small and local banks providing debt to an increasingly de minimis portion of the population of companies out there in the mid-market and small businesses happen materially starting the GFC and it's accelerated more dramatically, typified after SVB and FRB, et cetera. And then everyone talks about how direct lending is approaching $5 trillion and folks assume that that's serving the market that's less served by the banks. But the reality is 80% of private credits dominated by”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“MA and it's actually folks who are used to compete in that market and provide phenomenal solutions in that market are kind of outgrowing it.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“And checks that size, your guys just can afford to spend time on. At the same time, you see a continued pullback in what the smaller banks are doing. What's left is often really expensive or really rigid growth capital for these lower mid-market businesses. And it's not for everyone. Oftentimes while our capital is a little more structured and a little more tailored, we don't invest with back leverage. We don't require current coupons or current amortization. We're focused on the long-term cap gains event alongside management. So what we see as an opportunity to offer them best of both worlds. A little more upside preservation for them, but total alignment in that if they're winning, we're winning. And that makes us supportive of the right CapEx investments, people investments.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Mandate is flexible capital and structured equity. What's interesting is it feels more and more like we're filling a void. I don't know if it's a full black hole, but it's definitely a growing void. So you have this massive growth and at the same time consolidation of non-bank private credit. Trillions of dollars being managed by a small number of firms and in many ways the growth of those firms is phenomenal, but it's leaving companies behind that need 20, 30, 40 million dollars of debt. And it may not just be senior debt. It's mez, it's second lien. It's something that's a little more”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“So north of 90 annual gross retention, north of 100% year-over-year net retention, where these are businesses in financial services, real estate services and business services that are going to keep operating like clockwork. And they have through the recent tariff spikes, COVID, last several downturns, the key way to make money is can they either consolidate in a fragmented industry or can they grow organically in a way where usually they are selling some sort of product or services again in a fragmented industry, but they're selling that service to consolidators. So they're growing as a result of their clients' growth. Most of the securities that we're investing in are some form of preferred equity, so structured equity, senior preferred, convertible preferred, participating preferred. Casonia can take the form of other stuff too.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Relationship driven partner deals where we are investing either on a totally unlevered basis or in the upper half to upper two-thirds of the capital structure in a manner where we feel we're relatively downside protected and collateralized by some underlying recurring revenue stream that could be subscriptions, royalties, leases or other financial assets or a hard asset. We're primarily providing capital to these companies for growth. So it's mainly primary capital, sometimes a bit of secondary. We're really not doing any buyouts. We've never been an auction. We are investing in businesses where we hope have really low correlation with the capital markets. So these are businesses that they're in place revenue is super consistent.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think two sides of coin. So, what are we doing from a structure and approach perspective? And then what are the themes we're investing behind? So from a structure and approach perspective, we are doing”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Our first committed fond had a final close in 2019. So it was a good five, six years of really doing a deal by deal. Now, on the back part, we had a process. We had a team of five people. We had a lot of repeat family offices, high net worth, and even institutional investors. But it took a while. And frankly, we did it slowly because SPVs worked really well as a business for us. in order for us to level up our impact, retain really good talent, and also make it a little easier on our LPs. It made more sense to convert into funds. Having said that, still today, we have a pretty active co-invest component to everything we do.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“And thoughtful about research. So part of it is having the right idea. The other one is getting out there and listening and meeting companies and figure out ways to be collaborative and solution oriented. And not everyone on our team knows everything. But I think the combo today is what ends up being our secret sauce.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Think there's two components. So right now our senior team comes from similar backgrounds to myself. So they come from other institutions. Some folks have been at Coleman, but other institutional firms where they're investing in the same business, financial, and real estate services, combination of debt and equity. But they did it at a larger scale. So they're a part of rollups or creative financings. They have real institutional pedigree to understand what good looks like, but they've joined our team for that same reason. They find it more fun and rewarding to work in this part of the market. So having that debt equity lens is an important part of the team. Not everyone has it, but we have a mix of perspectives. And I think that's something that we're going to continue to focus on maintaining. And the other one is just being tenacious and dogged.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“And really intentional around the companies that we met where there was connectivity and where I believed we could truly add value beyond just writing a generic check.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Say when we were doing it then, it was again pick a theme within those focus sectors. Usually that theme is going to be the result of being on the right side of ongoing increasing regulation, consolidation in an industry, or adoption of technology, and just map the market and be dogged about meeting everyone and be comfortable getting lots of doors slammed in your face. finding warm connections for introductions. Cold emails never work for meeting people at conferences, meetups, referrals from larger funds where they thought they saw an interesting deal, but it was too small for them to invest in. So they referred it to us. But when we were starting, a lot of it was attempt to meet with and build relationships with hundreds of people and get rejected by most of them. So it was just getting really organized.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Because of some of the goodwill I had built up, management teams and sometimes existing owners were willing to give me a little bit of time to put together the capital because I was pretty upfront with them. Very quickly, there were a few families that more materially aligned with our business and began to fund all of our transactions, even though they were still case by case, slowly and kind of organically built a team.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source