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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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“A conventional debt investment and a levered private equity investment. So we're investing in the fat middle part of the capital structure. Sometimes it's an unlevered investment. Sometimes it's a super bespoke preferred security and took that same approach when we were doing one-off deal. So it was cases where someone didn't want to sell the company. They wanted to minimize dilution. They would give up some equity. They didn't want current paying debt. There was an opportunity to structure something interesting and differentiate it. The idea was leverage the relationships that I invested time and effort.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“The start, the goal was find a great deal, build relationships with initially family offices that love to fund one-off deals, and see if I could pair the two together. And the overarching theme and finding deals was how do I find something that is truly proprietary where I can justify my place in the capital structure versus another firm the way I did that was similar to how we approach investments today. develop sector expertise where board and management don't feel like they're educating you where i'm not necessarily telling them how to do their job but i may bring insights or connections or network to the table i think the second is be really solutions oriented so today at their street we're focused on businesses in the lower mid market that are somewhere between”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Portfolio companies I built up during my time with Coleman at Goldman, we're doing very industry specific vertical approach to sourcing. So build a point of view on a subsector, build a relationships within that subsector, get entrenched in the ecosystem, and then wait a few years till someone wants your help and capital and maybe overly confident i thought i could translate that into a few deals and i left and my thought was if it doesn't work out i'll go to business school my first office was the print center at staples Two blocks from my house that I would skateboard to in the morning because I had to get out of my apartment. My next office was Sublease Space and 9 West. So figured out office space. But it was really scrappy early beginnings driven by my interest and desire to get involved with these small businesses.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“But someone who had studied that industry, small but pithy insights, could actually make a difference in the business's evolution versus a billion dollar market cap company where there was a little I could add value to in terms of the CFO or the go-to-market strategy or a connection that I could make. And intrinsically, that was more interesting to me. And those deals were less efficient. Just you could get way better pricing. So I wanted to put my money on them. I left really because I wanted to experiment to see if I could get small deals done. They couldn't happen at Goldman. My plan was really there are a few families that had said that if I found deals, they would fund them. Scroll forward ended up working with an entirely different group of families to fund had enough money saved up and earned that I felt comfortable taking a risk and I was excited about a lot of relationships with potential.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“So, my path is a little different than some of the other guys that left. They had been working there 10, 15, 20 years. They were partners. They left with backing of a major asset manager. Mine was a lot scrappier, more entrepreneurial than that. Mine was a few years after the GFC. It just became really tough to do small deals. Number of committees had grown. There was more pressure to write checks that were larger that were worth the time and effort to justify the incremental bureaucracy and additional scrutiny we'd get around here three assets. And I like small deals. I thought small deals were more intellectually interesting. I like things that didn't fit, weren't cleanly defined, that fell through the crack somehow and love the fact that we could find a business at the right moment, even as someone that was young.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Consistent debt financing from a bank is really risky and particularly risky if you are sub $200 million market cap. So a small gust of wind, a small hiccup, and we saw this with SVB and FRB, et cetera, can just render your business completely insolvent. So my big thing today is really how does this business and how does this opportunity make a lot of sense on a completely on levered basis that makes sense to bring in leverage? Great. It's icing on the cake. It can be an accelerate. But can we build the business in a way where debt market can fall away? Lender may not renew the modest amount of debt that we've taken on and will survive and do great.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“We saw people doing minority deals without any real protections or some set of rights, but no clear form of enforcement of those rights and no game plan or instrument in place where if they needed to effectuate some sort of right they had underwritten and rely on, they could do it. There were debt deals that we saw that were underwritten assuming just the next guy would pay a higher price and the game of hot potato would play on, but there was no real focus on a liquidation or workout. So when the rubber met the road, there was little you could do. Today we spent a lot of time in financial services. And I spent a lot of time looking at financial services businesses. One of the things that stuck with me was having a business that is entirely reliant on dirt cheap.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Was formative to initially, but then when we saw things fall apart in terms of liquidity just entirely leaving the market through the GFC, it really hit home and focus on how you find multiple ways to de-risk, multiple ways to take your capital off the table. And then also hopefully multiple ways to win and win big if you can. That stayed with me into personal investing, into my time, my own firm. And then we were in an interesting seat because as certain funds had to dispose of assets in the face of 2008, 2009 liquidity issues and even banks dispose of assets, we got to look under the hood of a lot of these guys. And so we got to see what a lot of folks had done wrong. Really interesting position to learn from others move six.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Think the mantra of our group generally was don't lose money. So every deal was first underwritten like a debt deal. Our group was doing both public and private investing. I've spent all my time on private investments, both debt, equity, and a lot of things that were in between, JVs, minority deals, et cetera. And our capital was using the firm's balance sheet. So firm would allocate some amount of dollars, it would get levered eight to 15 times, and then we'd put it into companies. And so. Always the first set of questions around committee were where's the risk exposure? How do you lock in some basic return? And then how do you create some really interesting risk adjusted return? So deals that might only yield 10% or deals that are the potential to yield 30% were all weighed with consideration for the risk. Even when things were heady in”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Pre GFC, that was a really exciting way to learn, debatable how great that was from a risk management perspective for a regulated bank, but exciting way to learn our group did great. We were super profitable for the firm, I think, in and out of the downturn.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“I think my second or third week in the job, someone handed me a stack of papers and said, we're buying four aircraft from American Airlines, figure out how to get the deal done and close it. Now, the deal was signed. They'd agreed on the price, but there were logistics to be dealt with with coordinating, transfer of title with the FAA while the planes are on the ground, in between flight. Coordinating with tax counsel over 30 years older than me and spoke some foreign language, yet still in English, and all the little considerations and the guidance was figure it out. And so it was just spent a week pulling all nighters reading everything, asking a million questions. And on the other side of it, you feel a little more confident about the next deal.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Know if there was one aha moment when I joined, I was an analyst at Group was doing a little bit of everything. So anything that was too small for client raise third party funds got shuttled to our group where folks were trying to make money in interesting ways because there were smaller deals in part and because our group was an amalgam of some ancillary groups from other departments, when I joined, a lot of people were really young. You could get involved in a lot of different field types. So it was trial by fire. I was not someone that had been in Warden doing Excel classes previous to work. I had only used the Mac. I could barely use Excel. I was great at back of the envelope math, but that was about it. So it was really trial by fire and trying to play catch up. But in our group, because it was such a lean team and because the folks were young, you were thrown into the deep end and told to figure things out.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Creative lower mid market and mid market on balance sheet investing on behalf of the firm managed to get a summer internship in that seat that was called the special situations group and then was able to turn that into a full-time position and it was off to the races from there”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Of my time was involved in the music business, which is definitely not analogous to the types of things I invest in today. But in the classroom, there are a few experiences I had with independent studies or classes with adjunct professors who were entrepreneurs or real estate developers or had experience doing lower mid-market private equity. It wasn't called that at the time. The process of learning about that evolution of a company or evolution of a development project really intrigued me. I didn't totally understand how to connect working on those things into a linear career path, but it was something definitely of interest. And I was fortunate enough to have someone that was leading recruiting at Goldman Sachs, former Brown alum, be in a group that was doing”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Probably informally, I became interested in it, I'd say, in middle school and high school. No one in my family was in finance. I grew up in New York City, surrounded by lots of people in finance or real estate. A lot of those things didn't make sense to me at the time. But I was one of those kids that was always interested in following the stock market. And then also interested in how neighborhoods were changing and developers were shaping them and growing up in New York City in the 90s. and part of the 80s got to seek development of neighborhoods evolving and people around me were involved in that and benefiting from that and then when i got into college i went to brown generally a pretty liberal arts education i was a history major and honestly a lot of my time at school was spent working on a commercial radio station as a dj so”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source
“Guest on today's sponsored insight is Josh Kopowitz, managing partner of Thayer Street Partners, a boutique private equity firm he founded in 2012 that provides flexible growth capital to lower middle market companies in financial and business services. Our conversation traces Josh's journey from his early fascination with business and real estate to building Thayer Street into an institutional platform. We discussed the lessons he learned at Goldman Sachs and his transition from scrappy dealmaker to fund manager. We cover Thayer Street's thematic sourcing deal structuring and portfolio construction, the evolving landscape for non-bank growth capital, challenges of scaling a boutique firm, and Josh's vision for Thayer Street's future.”
2025-06-12 · Capital Allocators · Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451) · IDENTIFIED FROM THE TRANSCRIPT · source