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Thomas Wagner14 July 2023

Thomas Wagner on Sports Investing With Tom Brady

4Frameworks
13Insights

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Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster37:41

Rental Data Suggests EV Range Anxiety Exceeds Actual Driving Needs

Hertz examined how frequently customers drive more than 200 miles and found that long-distance rentals represented a small share of trips. Wagner argued that broader charging access—especially at places where cars naturally sit idle—can close much of the remaining practical gap.

  • Most rental days involve fewer than 200 miles
  • Many multi-day rentals also remain below 200 total miles
  • Charging is most useful at homes, hotels, restaurants, and offices
  • Underserved communities need charging options beyond private driveways

“Most rental days are less than two hundred miles”

Tom Wagner · 38:10

“this idea of range anxiety accounts for very small percentage of trips that people ultimately take.”

Tom Wagner · 38:18
#electric vehicles#charging#hertz#mobility

Hot Take· 2

Hot Take1:21:30

Why Wagner Was Still Waiting for the Office Distress Trade

Despite widespread concern about commercial real estate, Wagner said compelling opportunities had not yet appeared. The unresolved questions were aggregate office demand under hybrid work and which cities would remain structurally attractive, making patience preferable to prematurely calling a bottom.

  • Three-day attendance does not automatically reduce peak desk requirements
  • Providers and tenants are both still determining appropriate space
  • City-level outcomes may diverge substantially
  • Hybrid work changes utilization as well as total demand
  • Knighthead preferred observation to an early distressed purchase

“I think we're taking a wait and see and very patient approach right now.”

Tom Wagner · 1:22:01

“we haven't seen any opportunities that have really caught our eye yet”

Tom Wagner · 1:24:10
#commercial real estate#offices#hybrid work#distress
Hot Take1:33:56

Why Grid Resilience Should Rank Above More Visible Initiatives

Wagner identified electrical-grid vulnerability as an underappreciated systemic risk, spanning ordinary outages, cyber threats, and electromagnetic pulses. He advocated hardening distribution while expanding local solar, storage, geothermal systems, and microgeneration so failures do not cascade across society.

  • Modern urban areas depend heavily on uninterrupted electricity
  • Resilience is needed at both industrial and household scales
  • Distributed generation can reduce reliance on centralized infrastructure
  • Solar, storage, and geothermal can improve local energy independence
  • Grid hardening should be treated as a national priority

“making our electric grid more robust should really be at the top of our list.”

Tom Wagner · 1:35:07

“hardening the grid and distributing the power generator, you know, more solar, more renewable, all of it.”

Tom Wagner · 1:37:54
#electric grid#resilience#energy#infrastructure

Explainer· 4

Explainer41:36

The Investment Thesis Behind Brady and Wagner’s Pickleball Bet

Wagner saw pickleball as a small early-stage investment in a rapidly growing participatory sport. The league model adds city-linked teams and the tribal identity that has historically strengthened fan engagement, while Brady and Kim Clijsters add credibility and attention.

  • Participation growth created the initial signal
  • City-connected teams introduce local identity and tribalism
  • The investment was intentionally small and early stage
  • Commercial development still had a long way to go

“We liked the idea of a league with teams that are based in or connected to cities”

Tom Wagner · 42:08

“It's a it's an early early stage investment.”

Tom Wagner · 42:22
#pickleball#sports investing#leagues#fan engagement
Explainer53:28

Why Knighthead Connects Racing, Brands, and Portfolio Companies

Knighthead’s endurance-racing team is not treated as an isolated trophy asset. Wagner described connecting it with Porsche, Brady, Singer Vehicle Design, sponsors, and other portfolio holdings so that each sports investment supports a broader sector thesis and commercial ecosystem.

  • Knighthead owned the only private World Endurance Championship team that season
  • The racing entry used Porsche’s purpose-built 963 hybrid hypercar
  • Singer Vehicle Design created the car’s livery
  • Portfolio partners and sponsors were integrated into the team
  • New sports investments must fit a longer-term industry thesis

“we own a World Endurance Championship racing team.”

Tom Wagner · 53:28

“Anything that we do in sport, we try to think about how does it fit within other investments in our longer term thesis around a…”

Tom Wagner · 55:25
#motorsport#sports investing#portfolio strategy#branding
Explainer1:04:49

The Three-Part Plan Behind Knighthead’s Hertz Investment

The Hertz thesis rested on electrifying a large portion of the fleet, supplying vehicles to ride-hail drivers, and improving end-of-life vehicle disposal. Partnerships with automakers, Uber, and Carvana operationalized those ideas, while an unexpected chip shortage raised used-car values and accelerated de-risking.

  • Electrification required supply agreements with major manufacturers
  • Ride-hail vehicles created a new customer line
  • Carvana supported more efficient fleet disposal
  • The chip shortage unexpectedly increased used-car values
  • Company cash flow funded buybacks that increased continuing shareholders’ ownership

“that one was really predicated on three key tenants.”

Tom Wagner · 1:05:13

“we didn't have to put new dollars to work. We were simply reinvesting the cash flow of the company”

Tom Wagner · 1:06:47
#hertz#turnaround#electric vehicles#ride hailing#carvana
Explainer1:19:36

How Knighthead’s Annuity Business Converts Duration Into Yield

Unlike property-and-casualty insurance, Knighthead’s annuity operation is primarily a spread business. It invests incoming capital in a diversified pool and seeks to earn more than the fixed return owed to annuity holders, creating long-duration assets that complement deep-value investing.

  • Annuities generate economics from the spread between asset yields and obligations
  • Capital preservation is essential because promised returns are fixed
  • Controlled insurance assets behave like permanent capital
  • Long-duration capital expands the available investment set
  • Higher rates improved asset yields slightly more than annuity rates

“It's a it's a spread business.”

Tom Wagner · 1:20:00

“we have to manage to make a higher return on our diversefied pool of assets than what we are required to pay out to the…”

Tom Wagner · 1:20:12
#annuities#insurance#spread investing#permanent capital

Story· 4

Story02:03

How a CPA Engineered His Way Onto a Distressed Trading Desk

Wagner began in public accounting, where hedge-fund audits and derivative-control work exposed him to asset management and trading. After being told his background was wrong for trading, he deliberately pursued distinctive experience, Columbia Business School, an internship, and desk research until he secured the transition.

  • Accounting taught him the language of business
  • A trading-floor assignment revealed the career he wanted
  • Recruiting advice gave him a concrete transition path
  • He combined business school with 30–40 hours of weekly desk research

“I am wasting my life as an accountant. I gotta I gotta see a different”

Tom Wagner · 02:50

“I went back to business school to prosecute my path of moving from public accounting into the capital markets.”

Tom Wagner · 06:20
#career change#accounting#trading#business school
Story14:27

The “Buyers Only” Message When Markets Reopened After 9/11

Wagner witnessed the September 11 attacks from Goldman’s offices at 85 Broad Street and returned to a profoundly disrupted market. When trading resumed, Fidelity’s message that it would be a buyer only reflected an unusual moment of solidarity and restraint amid shared loss.

  • The desk had a direct view of the attack and its aftermath
  • Markets reopened under extreme emotional and operational stress
  • Major investors avoided discretionary selling on the first day
  • The episode remained one of Wagner’s defining market memories

“buyers only today”

Tom Wagner · 15:11

“for the first day, nobody was really unless they had to, no one was selling.”

Tom Wagner · 15:23
#9/11#market history#trading#crisis
Story15:42

Inside Wagner’s Most Intense and Profitable Trading Day

When WorldCom collapsed after an accounting revelation, Wagner traded until midnight, returned around 4 a.m., and continued into the following evening. Bonds lost dozens of points instantly, concentrating the attention of an entire trading floor on his market and creating the busiest, most profitable day of his trading career.

  • The news arrived just after the normal market close
  • Some WorldCom bonds dropped 50–70 points immediately
  • Wagner operated through roughly 36 hours of intense activity
  • Deep research later revealed valuable assets beneath the fraud

“it was the most profitable day of trading I'd ever had”

Tom Wagner · 16:13

“the bonds in that company fell fifty sixty seventy points”

Tom Wagner · 17:15
#worldcom#distressed debt#crisis trading#accounting fraud
Story24:24

Knighthead Launched Months Before the Financial System Nearly Broke

Wagner launched Knighthead in June 2008 with $413 million after earlier commitments had already fallen sharply. Because the new fund, Wagner’s family assets, and his wife’s employment were all concentrated around Goldman Sachs, a potential Goldman failure briefly threatened nearly everything at once.

  • Knighthead launched directly into the global financial crisis
  • Earlier commitments exceeded one billion dollars but contracted after Bear Stearns
  • The new fund initially had only one prime broker
  • Hidden concentration made the personal downside larger than anticipated
  • The firm performed well relatively in 2008 and exceptionally in 2009

“We had I think we launched with four hundred and thirteen million a capital”

Tom Wagner · 28:30

“if Goldman went the way of Leman, that I would probably you know, be wiped out.”

Tom Wagner · 29:03
#entrepreneurship#financial crisis#hedge funds#concentration risk

Takeaway· 2

Takeaway10:51

Why Elite Colleagues Accelerated Wagner’s Investing Education

Wagner credits much of his development to a Goldman distressed-debt team whose members combined experience, ability, motivation, and unusually intense work habits. Customer dinners also gave him sustained access to emerging leaders across hedge funds, mutual funds, insurance, and private equity.

  • The desk produced numerous future partners and asset-management founders
  • Working beside stronger and more experienced professionals accelerated expertise
  • Client relationships doubled as market education
  • The environment normalized sustained preparation beyond trading hours

“I was surrounded by people that were more experienced than I, that were in my mind, smarter than I”

Tom Wagner · 11:39

“that was credible education for me.”

Tom Wagner · 13:59
#mentorship#goldman sachs#expertise#networking
Takeaway1:25:48

The Hidden Hybrid-Work Cost for Early-Career Employees

Wagner argued that experienced workers may function well with fewer office days, but junior employees lose valuable exposure to seasoned colleagues. Hybrid work therefore requires explicit plans for training and mentorship rather than assuming that task completion alone measures organizational success.

  • Informal observation accelerates early-career development
  • Three office days remove a substantial share of direct contact
  • The learning penalty may be less than proportional but is not zero
  • Workplace decisions also affect city-center businesses and communities
  • Organizations must redesign development if work patterns change

“It's a massive loss.”

Tom Wagner · 1:27:28

“there's going to be some diminution in your ability to ramp up.”

Tom Wagner · 1:27:39
#remote work#mentorship#career development#hybrid work