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Colossus (Invest Like the Best / Business Breakdowns)Podcast5 Aug 2025Source: joincolossus.comHost: Patrick O'Shaughnessy

Andrew Milgram - Full-Contact Capitalism - [Invest Like the Best, EP.436]

In plain words

This is about investor Andrew Milgram's 'full-contact' approach, targeting distressed debt in the US middle market. He sees a 'K-shaped economy' where big tech thrives but the middle market struggles—EBITDA (a profit measure) dropped 20-25% since 2019, creating his opportunity. Key holdings: NYC taxi medallions (he bought over 4,000 for $600M, discovering Uber took drivers, not passengers); Employee Retention Tax Credit (ERTC) claims he buys at 85-86 cents on the dollar, expecting 12%+ annual return.

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Andrew Milgram, founder of Marblegate Asset Management, discusses distressed debt investment strategies in the middle market. His core view: middle-market EBITDA has declined 20–25% since 2019, forming a "K-shaped economy." He details his signature investment—betting over $600 million on New York Ci

~11 min full read · 7 sections
Deep Analysis

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At a Glance

Andrew Milgram, founder of Marblegate Asset Management, discusses his unique "full-contact" middle-market distressed debt investment strategy. The most significant takeaway this issue: Andrew Milgram believes that U.S. middle-market EBITDA has declined 20–25% since 2019, creating a "K-shaped economy," and it is precisely this widely overlooked economic distress that forms the core source of his investment opportunities.


K-shaped Economy: The "Hollowing Out" of the Middle Market and Investment Opportunities

Andrew Milgram argues that the U.S. economy is exhibiting a "K-shaped" divergence, with the lower branch—represented by the middle market (enterprise value between $100 million and $750 million)—experiencing a persistent and severe "hollowing out."

Milgram calls this phenomenon a "K-shaped economy": On one side, the "ticker-tape economy" represented by large-cap tech stocks is performing strongly; on the other, the middle market—which accounts for roughly one-third of the U.S. economy—is under immense pressure. Using an anonymous dataset covering over 1,200 middle-market companies, he found that EBITDA in this segment has fallen 20-25% since 2019, profit margins are in the mid-single digits (well below the ~15% median for public companies), and after-tax net income has been negative for the past two years, declining by nearly 200%.

The core mechanism is the "corporate class system." Milgram points out that middle-market companies typically serve large publicly traded corporations, which have pricing power and can pass down cost pressures layer by layer. Large companies squeeze their supply chain profits, causing middle-market firms to "get poorer and poorer." This explains why middle-market companies are more prone to distress; historically, this segment has accounted for more than two-thirds of bankruptcy and restructuring cases.

Extrapolation and signals: Milgram believes that the resolution of this distress "will end with a bang." The signals are already visible: in the 2023 data, nearly 25% of middle-market companies could not cover their interest payments (the ratio was still 20% in 2024), and corporate bankruptcies in 2024 hit a 14-year high. He expects bankruptcy volumes to remain at or above that level in 2025. He leans toward the view that this will be a "slow, sustained restructuring" similar to the late 1980s and early 1990s, rather than a one-off crisis.


出租车牌照:从“最差想法”到 6 亿美元押注的完整案例

Andrew Milgram 详细讲述了其最著名的投资案例——纽约市出租车牌照(medallions),并归纳出贯穿其投资方法论的核心原则:理解对方、尊重数据、全周期介入。

背景与数据洞察:2016 年,当 Uber 崛起时,市场普遍认为出租车牌照已死(此前峰值达 120 万美元/个)。Milgram 最初也认为这是“有史以来最差的想法”。但他及其团队花费两年进行研究,甚至亲自考取出租车驾照并驾驶。通过分析从纽约市出租车管理局(TLC)获得的“数 TB”原始乘车数据,他们发现关键事实:Uber 并未抢走乘客,而是抢走了司机。Uber 通过补贴吸引司机,使出租车大量闲置。同时,数据揭示了乘客行为模式(如东-西向短途更倾向出租车)和司机优化路径(如“NASCAR 环路”)。

交易与架构:Milgram 从一家银行的破产拍卖中,以远低于市场预期的 16万美元/个 的价格收购了 48 个出租车牌照。这一“锚定交易”迫使所有贷款机构(主要是银行和信用合作社)在年底重新评估其资产价值。随后,他顺势展开了大规模收购。由于监管压力(银行是“监管导向的参与者”),他最终从联邦政府(通过 NCUA,即信用合作社的 FDIC)手中收购了最大的资产包,总投资超过 6 亿美元,持有超过 4,000 个 牌照(总量为 13,587 个)。

运营与人性介入:Milgram 强调这是“全接触式”投资。他自建了拥有 30 人的服务团队来处理贷款,并与工会(Taxi Workers Alliance)建立建设性关系(甚至亲自加入游行队伍)。他通过数据驱动的方式指导司机(如“NASCAR 环路”),并开设了“出租车俱乐部”以改善司机生态。近期,他将整个出租车运营业务上市,并认为在自动驾驶时代,出租车牌照作为纽约市控制城市交通的“监管工具”仍具有持久价值。


谈判原则与人性因素:理解“对方”的硬约束

Andrew Milgram 将“理解对方的需求与硬约束”视为其谈判和投资成功的第一性原理,并强调每笔困境投资都是“商业问题与人性戏剧”的结合。

核心原则:Milgram 认为,“知道你想要什么很容易,真正的挑战是理解对方”。他要求团队从多个维度理解对手方:通过对话和实地考察(“很多投资经理从不去看工厂”),以及通过数据分析(数据有时揭示的与对方直觉不同)。他特别强调,银行是“监管导向的”而非“经济导向的”,其决策主要受监管约束驱动。因此,他主动与所有相关监管机构(纽约市议会、TLC 等)沟通,预先解释其计划,从而获得信任。

谈判铁律:在谈判中,他遵循“幼儿园原则”:尊重对方,诚实透明,为对方留有余地(“不能是零和游戏,必须给对方留点东西”),并保持合理的节奏(“时间会扼杀交易”)。他承认,自己常被视为“万恶之源”,但坚持要以“有尊严、有尊重、有同情心”的方式对待正在经历人生最困难时刻的对手方。

案例:员工保留税收抵免(ERTC):Milgram 举例说明如何利用“变体观点”获利。他通过法律和数据分析,发现 CARES 法案中的 ERTC 条款设计松散、执行缓慢(政府为此已支付超 2000 亿美元),且主要受益者是资本受限的中端市场企业。他以约 85-86 美分/美元 的价格收购这些企业的合格退税权,并享受 6-7% 的等待期利息,从而获得约 12% 的最低年化回报。这个能产生如此高回报的机会之所以存在,是因为大多数大型机构(如 Apollo)不擅长处理这种“琐碎、手工、和政治敏感”的资产。


Private Credit Market: Risk Stratification and "Lazy" Investment

Andrew Milgram sharply criticizes the current private credit market, particularly CLOs and certain BDCs, arguing that they conceal real risks by "manipulating" default rates and using "payment-in-kind (PIC)" debt.

"Laziness" and Risks in the CLO Market: Milgram believes that CLOs (collateralized loan obligations) have become a primary tool for credit creation, but many CLO managers rely excessively on "diversification and overcollateralization" as risk control measures, lacking deep thought about individual credits. He characterizes this as "outsourced thinking" and "laziness," which could ultimately lead to problems.

The "Duplicity" of Private Credit: Milgram points out that "the default rate is the most easily manipulated statistic" — if the lender does not declare a default, it does not exist. He advises investors not to ask about default rates, but rather about "waiver rates" and "amendment rates." Citing Fitch data, he notes that approximately 82% of the private credit market is rated B- or below (equivalent to CCC grade). The historical 3-year cumulative default rate for CCC-rated bonds is about 30%. He questions why most private credit managers report default rates below 1.5%. In his view, either they have invented "new ways to avoid losses," or they are misleading the market.

Warning on "Payment-in-Kind (PIC)" Debt: Milgram uses the phrase "PIC means payment won't come" to describe the potential risk of this instrument. He notes that when a company cannot pay cash interest, the lender is effectively taking on equity risk. He observes that in some BDC (business development company) portfolios, PIC debt accounts for as much as 17-18% of holdings, meaning these "lenders" have essentially become high-risk "equity holders."


提及的标的

标的 嘉宾态度 关键数据
纽约市出租车牌照 看好,已完成投资并上市 总投资超 6 亿美元;持有超 4,000 个牌照(总量 13,587 个);初始收购价约 16 万美元/个。
员工保留税收抵免 (ERTC) 看好,已大规模投资 收购价格约 85-86 美分/美元;参与方为美国政府;预期年化回报约 12%+。

Judgments Worth Remembering

1. “The K-shaped economy is the macro framework for investing.” Andrew Milgram believes that U.S. middle-market EBITDA has declined 20–25% since 2019, creating a severe divergence between the “ticker-tape economy” and the “middle-market economy,” with the latter forming the core source of his investment opportunities.

2. “Banks are regulation-driven, not economy-driven.” Andrew Milgram stresses that understanding the true constraints of counterparties (especially banks’ regulatory constraints) is the key to successful transactions. He actively communicates with regulators and leverages their pressures (e.g., banks’ year-end asset write-down pressures) to facilitate deals.

3. “Default rates are the most easily manipulated statistic.” Andrew Milgram warns that the 1.5% low default rate reported by the private credit market is misleading, and actual risks may be hidden. He advises investors to focus on “waiver rates” and “amendment rates” rather than “default rates,” and to be wary of the 17–18% “payment-in-kind (PIK)” debt in BDCs.

4. “The middle market is the ‘manufacturing division’ of distressed investing.” Andrew Milgram refers to private equity (PE) as his “manufacturing division,” because companies acquired by PE continuously generate problems. The middle market, with its information opacity and rigid capital structures, is a “rich mine” for these problems, which is why he focuses on this inefficient market.

5. “From the ‘worst idea’ to a $600 million investment, the key lies in data and human nature.” Andrew Milgram drove in person and analyzed “terabytes” of Uber’s TLC data to reveal the critical fact that “Uber steals drivers, not passengers,” proving his investment methodology is a combination of “data-driven decision-making” and “understanding human factors.”

6. “The core of negotiation is understanding the other party, not expressing yourself.” Andrew Milgram treats “respecting the other party’s hard constraints” and “creating a non-zero-sum solution” as his ironclad rules for negotiation. He even marched in protests alongside union members during his taxi medallion investment in order to understand their needs.

7. “There is no investment that is not a blend of business issues and human drama.” Andrew Milgram notes that in distressed investing, counterparties (such as taxi drivers) are going through the most difficult moments of their lives, so investors must treat them with empathy—but this does not mean abandoning business principles; rather, it means seeking solutions based on “understanding human nature.”

8. “Networking is overrated, and specific work is severely underrated.” Andrew Milgram believes the current investment industry has a tendency toward “laziness” and “outsourcing thinking,” while true excess returns come from “variant views” and a “full-contact” investment style that involves personally solving specific problems.