Today’s Newsletter is Sponsored by Daloopa

You don’t have to be an investment analyst to know that data entry sucks. If you are an investment analyst, however, meet Daloopa.

Daloopa increases the velocity of a team’s idea generation at scale. Analysts spend less time locating and manually inputting meaningful disclosures into Excel and more time synthesizing in the minutes after the print.

  • Make the most informed investment decision knowing that Daloopa captures every reported number, including from footnotes, MD&A’s, and investor presentations
  • Auditable numbers in Daloopa’s data sheets mean that you are able to easily verify numbers and ensure accuracy
  • Update models quickly in a single click in minutes after the results are out
  • Easily build and maintain custom Excel dashboards to spot industry trends and outliers



Register for Webinar: ‘Inflection Investing’ with Harris Kupperman

Markets are in constant flux, shaped by numerous factors from macroeconomic shifts to company-specific events. Learning to identify these pivotal moments can unlock significant investment opportunities for you.

Join me for an insightful discussion with a fellow history major… the one and only Harris Kupperman, Founder of Praetorian Capital. Renowned for his unique ‘Inflection Investing” approach, that entails finding out-of-favor companies where fundamentals are starting to inflect, Harris will delve into:

  • Macro Inflections: Thematic tailwinds and cycle changes
  • Event-Driven Inflections: Company transformations and special situations
  • Case study on energy and uranium stocks
  • Synthesizing history in the investment process
  • The right and wrong applications of historical precedent


Crypto’s Bucket Shop Problem

A 19th century bucket shop in NYC

Before going any further, I must mention one of the most important updates of my life…! On May 27th, I got married to my beautiful wife: Maris Catherwood! We have been together since high-school, and on 5/27 we officially tied the knot. She simply looks too beautiful to not share these pictures:

Okay, now back to financial history!

A Wild Week for Crypto

This was a wild week for crypto and market regulators. I think these article thumbnails from Bloomberg, side by side, say it all:

As with every major development in the world of crypto – and following the FTX fiasco starting last Fall – the recent news sparked debate over whether crypto was just another investing fad that is finally unraveling, or whether there is still an important role for crypto in financial markets and society.

As it’s been a little while since we discussed cryptocurrencies, I want to revisit some of my previous articles on the topic. In particular, I’d implore everyone to read the first article in this week’s newsletter, which I wrote last summer for Bitcoin magazine. In the piece, I argued that major crypto players will face the same problem that late 19th / early 20th century stock exchanges faced in the United States.

“Ardent Bitcoin supporters would likely agree that there are rampant levels of manipulation and fraud in the broader cryptocurrencies and digital assets landscape. Bitcoin, however, should be insulated from these nefarious activities, right?

Unfortunately, Bitcoin is undeniably impacted by the bad practices elsewhere in the crypto and digital asset ecosystem because bad actors frequently use BTC at some point in their schemes (i.e., as collateral, reserves, etc.). For example, when the algorithmic stablecoin TerraUSD unraveled in May 2022, bitcoin suffered because the Luna Foundation Guard set up by Terra’s founder dumped $3.5 billion worth of bitcoin on the market in attempts to prop up TerraUSD’s price. Although Bitcoin was not involved in the issues that led to TerraUSD’s unraveling, it was still negatively affected by this speculative episode. This is the burden bitcoin bears by being the largest cryptocurrency.

During the bucket shop era, stock exchanges learned that despite their best efforts, theoretically fictitious trades in seedy bucket shops had real consequences. Similarly, Bitcoin is still subject to the manipulative and fraudulent activity perpetrated by bad actors in other areas of the digital asset landscape.

Like stock exchanges in the early 20th century, Bitcoin supporters should cautiously welcome some government regulation in crypto and digital assets because it should help prevent bitcoin’s price being affected by bad practices elsewhere in the ecosystem.

The precedent for this is found in average IPO returns before and after regulations imposed by the 1933 Securities Act were established. When there was little consequence to floating shady companies and frauds on the stock exchange, bad actors did not hesitate, and the average investor suffered. Yet, after the Securities Act, the general quality of companies going public increased dramatically because of the disclosure requirements and personal liability of parties involved.

Bitcoin is currently in the “democratization without regulation” phase of development, which history has shown to be perilous for retail investors. To ensure the average investor can feel confident about not being exploited, the basic levels of government regulation that exist for other asset classes  are needed to protect investors and facilitate broader adoption.

Regulation might be a taboo word for many Bitcoin proponents but accepting some regulation may fuel the growth of Bitcoin over time.”

It seems like we may finally be moving out of the ‘democratization without regulation’ stage of crypto markets development. Regulators sure seem ready to regulate after this week!

Regulating Crypto – Democratization & ‘The Bucket Shop Problem’

Why This is Relevant:

This article draws parallels between the evolution of equity markets and the current state of the crypto market, emphasizing the need for regulation to protect investors and facilitate broader adoption.


 “The article explores the history of equity markets, focusing on the role of technology in democratizing access and the subsequent rise of speculative behavior and manipulation. It highlights the impact of the 1929 crash and the introduction of securities regulations in the 1930s, which improved market conditions and investor protection. The article suggests that Bitcoin and the broader crypto market are in a similar phase of “democratization without regulation,” and argues that some level of government regulation could prevent manipulation and facilitate broader adoption.”

Visualizing History:


When Volcanoes Erupt: FTX, Railways & Bank Runs

Why This is Relevant:

Historical perspective on the downfall of FTX, drawing parallels with the financial panics of the 19th and early 20th centuries. It highlights the risks associated with speculative investments and the potential need for regulatory intervention, providing valuable insights for investors navigating the volatile crypto market.


“This discusses the collapse of the crypto exchange FTX and draws parallels with historical financial crises. It highlights how speculative investments and poor risk management led to the downfall of major financial institutions in the past, particularly during the Panic of 1857 and the Panic of 1907. The article suggests that the crypto market, like the railway industry in the 19th century, is experiencing volatility and risk due to a lack of regulation. It also discusses the potential need for regulatory changes in the crypto market, similar to the establishment of the Federal Reserve following the Panic of 1907.”

Lessons for Crypto from The Gilded Age

Why This is Relevant:

Crypto is often seen as the wild west of finance, but it’s not the first time we’ve been here. The Gilded Age of the 19th century was a similar era of rampant speculation, insider trading, and fraud. Understanding this historical context can help us navigate the current crypto landscape and anticipate potential regulatory changes.


In the Gilded Age, insider trading was the norm, pump-and-dump schemes were common, and outright fraud was not unheard of. Sound familiar? The parallels between the 19th-century equity markets and today’s crypto markets are striking. Just as the equity markets eventually transitioned from a “wild west” to a regulated environment, crypto seems to be on a similar trajectory. The recent insider trading charges against an OpenSea employee could be a turning point, much like the landmark Supreme Court case in 1909 that paved the way for greater regulation in financial markets.

Missed last week’s article? Catch up here!