Feldman's Faves: October 27, 2025

GOOD MORNING EVERYONE

Our JAYS have been really fun (and extremely stressful) to watch. The ALCS GAME 7 win was epic as was GAME 1 of the WORLD SERIES (Game 2, not so much). I know we are the big time underdogs here but let’s the hope the boys can finish the job this week. At this time next week, we will know. Meanwhile I hope you are all enjoying the ride.

Changing topics, I want to congratulate our United Way Committee who did such a great job last week. The fun and generous nature of our firm was on display, which makes me very proud.

This week at Goodmans (and all of Bay Street) is a crazy one as we embark on summer student interviews. Thanks to everyone who is contributing to this extremely important week. Let’s continue to make our firm top notch by continuing to bring in the best and the brightest students.

This week theme is interesting business stories.

1929 – INSIDE THE GREATEST CRASH IN WALL STREET HISTORY – AND HOW IT SHATTERED A NATION By: Andrew Ross Sorkin - Andrew Ross Sorkin is back with his new book 1929 – that is just flying off the shelves. Everyone knows what happened in 1929 and the devastating aftermath of the Great Depression. So the story that Sorkin tells is not surprising. I still think John Kennth Galbraith’s version remains the gold standard. That said, Sorkin has a great skill in focusing on the key players and their personalities (taking the BIG MAN approach to history) that is unique. So we get to relearn about the people that were involved in the crash and those who were left to clean up the mess. We also see (as one would expect) the parallels in the 1920s and the 2020s – let’s hope we are smarter this time around…. As one reviewer notes, “The Wall Street crash of 1929 is widely regarded as the definitive stock-market collapse of modern times. What’s perhaps less widely known is that it was preceded two decades earlier by the almost equally dramatic crash of 1907. With the 20th anniversary of the global financial meltdown of 2008 now just a few years away, it’s hard to resist drawing parallels between the events that took place a century ago and what’s happening today. Once you start looking for similarities, you see them everywhere. In the 2020s we’re experiencing a wave of right-wing populist protectionism just as intense as the one that swept the globe 100 years ago. Today nationalist sentiment is on the rise as developed countries seek to stem a tide of economic migrants. That also was true in the 1920s, when the United States reversed its long-standing open-door policies. Before the 1929 crash, emerging technologies were threatening traditional livelihoods: Back then the culprits were industrial agriculture and manufacturing. Today the threat is coming from artificial intelligence.

It’s perhaps predictable, then, that the New York Times journalist and CNBC co-anchor Andrew Ross Sorkin has produced a prequel to his 2009 blockbuster Too Big to Fail: The Inside Story of How Wall Street and Washington Fought to Save the Financial System—and Themselves, in which he chronicled the 2008 crisis. The new book is 1929: Inside the Greatest Crash in Wall Street History—and How It Shattered a Nation. It largely follows the narrative structure of the earlier one, presenting a series of dramatized accounts of meetings between various players. Sorkin helpfully provides a cast list, reinforcing this reader’s sense that this book (like his previous one) was designed to be the basis for a screenplay. (It also confirms how much of a boys’ club Wall Street has remained: Only one woman figures in 1929’s list of 105 names; just 10 women made the list of 161 for the 2008 crisis.) In 1929 you’ll find all the ingredients of a compelling one-season series for Apple TV+ or Netflix: wealth, ambition, greed, ideology, and stupidity, combining to an inevitable end desired by no one. At the heart of the story are several financial institutions, which in many cases also appear in Too Big to Fail—notably the House of Morgan (today’s JPMorgan Chase) and National City Bank (the forerunner of Citibank). Politicians and government figures include Presidents Hoover and Roosevelt, the steel and banking magnate Andrew Mellon (who served as the U.S. Treasury secretary), and Carter Glass, the U.S. senator who lent his name to the financial reforms that followed the 1929 crash. (The repeal of that legislation is considered by many to be an important contributor to the 2008 crisis.) The book is told in 42 chapters, each describing and discussing a key date in the story of the market collapse. It’s divided into two parts: the buildup to the crash and its immediate aftermath, February to December 1929; and the longer-term fallout and the early years of the Great Depression, April 1930 to June 1933. There are several intertwining storylines, which are at times difficult to keep straight, but this is more than compensated for by the lively writing and compelling historical background. In comparing Sorkin’s crash books—and considering which signals, if any, might alert today’s market watchers to looming peril—two plotlines stick out. In 1929 we meet “Sunshine” Charlie Mitchell, the National City Bank chairman and president, in the book’s prologue. It’s the evening of October 28, 1929, a day before the market collapse, and he’s in the grip of a growing panic. Two months previously he finalized an acquisition that would make his bank the world’s largest, well ahead of its nearest rival, Chase. Shareholders in the subsumed bank (the Corn Exchange Bank) could swap their shares for four-fifths of a share in National City or $360 in cash. However, share prices in National City have started to waver, and Mitchell learns that National City’s traders have been forced to buy unexpectedly large quantities of its own stock to keep the price high enough to tempt Corn Exchange investors to opt for shares over cash. Since National City doesn’t have enough cash on hand to pay for the shares, Mitchell feels obliged to use his own private fortune to cover the purchases. The bank is, in short, confronting a classic liquidity crisis, and its chairman’s driving fear is that if that news leaks, it will trigger a bank run, with depositors racing to withdraw their money before National City runs out of it. Ultimately, Mitchell cannot stabilize the stock price, the merger is called off, and although National City Bank itself survives the crash, the onetime Wall Street hero finds himself vilified as the personification of Wall Street’s greed.

There are distinct echoes of that crisis in one of the main Too Big Too Fail storylines—that of Lehman Brothers, which, in the absence of a retail deposit base, largely financed its stock and bond trading activities through the wholesale money markets. As word of Lehman’s huge exposure to subprime real-estate spread, triggering repeated sharp drops in its share price, its chief executive, Dick Fuld, realized the firm could no longer secure short-term financing. So he began to desperately search for a deep-pocketed buyer. His failure to find one led to Lehman’s collapse. And as Sorkin explains, Fuld, like Mitchell before him, became the target of a great deal of the ensuing public outrage about Wall Street’s perceived excesses and malpractices. Are there figures like Mitchell and Fuld lurking about today’s Wall Street? Can Sorkin’s recounting of their stories offer any insights into how to avoid future calamities amid this fraught period in global history? Although both 1929 and Too Big Too Fail offer entertaining accounts of how the two crises played out, neither book provides much in the way of economic analysis, let alone suggests what measures we might take to guard against another massive market crash. To be fair, Sorkin didn’t set out with those objectives, and he probably believes that they are unrealizable. Indeed, as he concludes in his epilogue to 1929,“ultimately, the story of 1929 is not about rates or regulation….It is about something far more enduring: human nature.” His prescription: humility. We can always hope that today’s finance chief executives grasp that and have absorbed the lessons of history by now. But unfortunately, it’s all too likely that Sorkin will soon be bringing out a third title in the series: 2029: When Will They Ever Learn?” I really enjoyed this book. It was an easy quick read and Sorkin allows us to get to know the players at that time, which is different from other books written about that era and the events we all know so well. I hope the world has learned its lessons but I guess we will see. I think the movie will be good at least. Here’s a good review from the WSJ - https://www.wsj.com/arts-culture/books/1929-review-year-of-the-crash-5143003b

ALL-IN WITH CHAMATH, JASON, SACKS & FRIEDBERG - How Orlando Bravo Built One of the Most Successful Firms in Private Equity – It’s rare these day to do a major tech deal without Thoma Bravo in the mix. I think its fair to say that when you think about tech PE that Thoma Bravo is THE NAME in the space. The story of how this business grew and grew (managing over $200B in assets) with the most effective acquisition team in the space reflects their mentality of buy the best and operate the best. This mantra is really that of Orlando Bravo who tells his story and explains the TB way (not to be confused with Tom Brady….). There is also a shout out to one of the deals we are working on right now (pretty cool). Here’s an excerpt from the PODCAST itself, “Introducing Orlando Bravo (1:53) Orlando’s history, Puerto Rico origins, how he got into private equity (7:10) How he runs Thoma Bravo: small team, outward facing, mentorship, patience in fundraising (9:01) Role of PE in the American economy, public perception, underwriting AI risks (15:23) Deal pricing philosophy, acquiring Boeing’s avionics business (19:24) Thoma Bravo’s operating playbook after acquiring a company (26:16) Thoughts on taking Thoma Bravo public”: https://podcasts.apple.com/ca/podcast/all-in-with-chamath-jason-sacks-friedberg/id1502871393?i=1000731960526

Thank you for your ongoing engagement and participation.

And remember to stay safe, stay healthy and to docket daily.

Jon