The Harder You Work, the Luckier You Get

What this book actually teaches

The Harder You Work, the Luckier You Get (2019) is the memoir of Joe Ricketts, founder of Ameritrade (later TD Ameritrade), one of the pioneering discount brokerage firms that democratized retail investing by dramatically lowering the cost of stock trading. Ricketts traces his path from a modest upbringing in Nebraska through the founding and growth of First Omaha Securities in 1971, the company's evolution into Ameritrade, and the competitive battles of the discount brokerage era that eventually consolidated into TD Ameritrade's $22 billion acquisition by Charles Schwab in 2020. The memoir combines entrepreneurial biography with his philosophy of disciplined risk-taking, hiring, and business building.

The most substantive portions of the book cover the founding period in the early 1970s and the sustained competitive battles that defined the discount brokerage industry. Ricketts entered the brokerage business immediately after the SEC's 1975 deregulation of fixed commissions — the moment when the decades-old cartel pricing for stock trades ended and a price war became possible. His core business insight was straightforward and durable: if the technology existed to execute stock trades efficiently at low cost, and regulatory deregulation permitted variable pricing, then a brokerage that charged dramatically less than the wirehouse incumbents could win price-sensitive customers who were buying and selling stocks on their own judgment anyway. Ameritrade's early growth was built on this arbitrage between the cost of executing trades and the prices incumbents were still charging.

Ricketts writes candidly about the cash crises, failed product bets, and management failures that nearly ended Ameritrade in its early years. The accounts of how he navigated capital shortfalls and made decisions without adequate information are among the more instructive parts of the book for entrepreneurs — not because the tactics are replicable, but because they illustrate that surviving as a founder often requires making acceptable bets under genuine uncertainty rather than finding optimal solutions.

The later sections address his political views, his founding of DNAinfo (the local news venture), and his family's ownership of the Chicago Cubs. These chapters are personal and candid but less directly relevant to the business-building lessons that make the earlier sections worth reading.

The weaknesses include the memoir's selective nature: accounts of Ricketts's own decisions read charitably, as one would expect from a founder's self-authored account. The competitive dynamics of the discount brokerage wars — including the role of Charles Schwab and Jack White — receive less attention than a neutral history would provide. Readers interested in a more balanced account of the discount brokerage industry's development should supplement with external sources.

For entrepreneurs interested in company-building during industry disruption — specifically the mechanics of competing on price against entrenched incumbents in a newly deregulated market — Ricketts's account of Ameritrade's early years provides instructive first-person perspective. The memoir format means it is a story, not a system.

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About Joe Ricketts

Read more from Joe Ricketts and explore the full bibliography on ClearValue Books.