The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

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why aren't all 12 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Insight
Private Credit Mega-Funds Leave $20M to $40M Borrowers Underserved
“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…”
Josh Kopowitz Jun 12, 2025 ▶ 22:30 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Disclosure
Thayer Street Targets 60% to 80% LTV With 3x to 4x Upside
“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% …”
Josh Kopowitz Jun 12, 2025 ▶ 45:49 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Insight
Scaling From 30 to 100 Employees Drives Most Operational Breakdowns
“The thing that happens most consistently when things go wrong is companies scaling nicely. The company goes from 30 employees to a hundred, and there is a new set of management issues. Layers of the org chart. An executive that's used to having control or bein…”
Josh Kopowitz Jun 12, 2025 ▶ 39:58 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Assertion Not checkable as stated
Top 20% of Private Credit Firms Dominate 80% of the Market
“80% of private credit is dominated by 20% of the players. They are investing out of 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 fifty million …”
Josh Kopowitz Jun 12, 2025 ▶ 25:06 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Disclosure
Every Thayer Street Employee Receives Carry or Synthetic Carry
“Employees up and down our team are participants in carry or synthetic carry. Every single person in our team.”
Josh Kopowitz Jun 12, 2025 ▶ 50:01 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Disclosure
Thayer Street Engineers 10% to 14% IRRs Even With Zero Growth
“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% IOR.”
Josh Kopowitz Jun 12, 2025 ▶ 31:02 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Insight
90% Recurring Revenue Enables Strategic Exits Even if Operational Scaling Fails
“The good news is usually there's 10, 20, 30 other players, many of whom are larger, that want these customers. And the customer relationships are so sticky. These are businesses recurring it with 90 plus percent recurrence. We can still generate a lot of value…”
Josh Kopowitz Jun 12, 2025 ▶ 41:01 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Disclosure
Thayer Street Caps Fund Positions at 10% Across 10 to 12 Deals
“When we think about our funds, they are, call it plus or -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 …”
Josh Kopowitz Jun 12, 2025 ▶ 45:25 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Disclosure
Thayer Street Structures a 1.5x Minimum Return Across Its Portfolio
“So across our portfolio today, we have just shy of a 1.5 X minimum return.”
Josh Kopowitz Jun 12, 2025 ▶ 30:55 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Disclosure
Thayer Street Payments Portfolio Company Grew GPV 5x in Four Years
“So that company grew probably four X in terms of top line revenue and another closer to five or six X in terms of Gross processing volume over a four-ish year period.”
Josh Kopowitz Jun 12, 2025 ▶ 36:28 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Disclosure
Thayer Street Completes 80% of Diligence Before Striking Deals
“Usually when we've struck a deal with someone or found a company that's ready to go, 80% of our diligence is done.”
Josh Kopowitz Jun 12, 2025 ▶ 27:41 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
Disclosure
Thayer Street Structures Deals Without Back Leverage or Current Amortization
“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.”
Josh Kopowitz Jun 12, 2025 ▶ 23:23 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
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