Tom SosnoffCo-founder & CEO

When we sold thinkorswim, we had disrupted retail brokerage technology and trading commissions, but financial television remained completely broken. Watching traditional networks like CNBC or Bloomberg drove me crazy because they featured the same repetitive analysts offering generic advice. We rented a defunct hip-hop recording studio in downtown Chicago without knowing anything about broadcasting. Within two years, we turned it into the largest digital financial media network in the world. Our mission has always been to eliminate financial illiteracy by delivering transparent, entertaining, and mathematically grounded market commentary.

My father was a passionate civil rights attorney and a professor at Yale Law School who was as close to a committed socialist as you could get, while my mother taught art for decades. When I graduated from college in 1980 during a period of twenty percent interest rates and zero jobs, the only interview I managed to secure was at Drexel Burnham Lambert on Wall Street. When I accepted the position, my parents were simply relieved I had employment. While working in New York, traders told me they needed someone to move to Chicago to trade on the floor. I flew out, walked onto the exchange, and was instantly hooked.

I had never been west of the Hudson River. When I stepped onto the trading floor of the Chicago Board Options Exchange at the Board of Trade, people were screaming, tickets were flying through the air, and the noise was deafening. It immediately matched my personality. It felt like the wild west meeting raw capitalism. On my first day in the city, I went to Comiskey Park, caught a foul ball that ricocheted off the concrete, and spent the following afternoon swimming at the beach. That energy confirmed Chicago was the place where I belonged.

Passive investing relies on blind hope that asset prices will drift upward over decades. Active trading is strategic and probabilistic. Learning how to buy and sell assets teaches you how to manage risk, evaluate odds, and understand statistical variance in ways passive investing never can. Options bring mathematical efficiency to asset pricing because they allow you to quantify and trade volatility rather than merely guessing price direction. Active participation turns investing into a disciplined skill rather than a passive waiting game.

We run our businesses through a divide-and-conquer approach. Scott handles the day-to-day operations and internal management, while I focus on visionary product strategy, promotion, and media. We give each other space, never argue in front of employees, and share the exact same appetite for risk. Whenever we face a major fork in the road where we must choose between playing it safe or doubling down on growth, we both instinctively vote to embrace the risk.

Scott and I maintain a strict rule of no high fives. When we close a massive funding round, execute a multi-hundred-million-dollar deal, or launch a breakthrough platform, we never stop to congratulate ourselves. Celebrating creates complacency. The moment a transaction is executed, we immediately turn our focus to building the next initiative. That lack of ego keeps us grounded and focused on continuous execution.

In early 2009, during the depths of the financial crash, we received three acquisition bids within days because investment bankers cannot keep secrets. TD Ameritrade wanted to acquire thinkorswim, but because their stock price was depressed, we preferred equity rather than cash. Simultaneously, the Ricketts family wanted to purchase the Chicago Cubs but needed immediate liquidity. We structured a three-way transaction where we received TD Ameritrade equity, the Ricketts family received the cash payout from the transaction to purchase the Cubs, and TD Ameritrade took ownership of thinkorswim. The entire deal was executed in roughly two days.

During the height of the SPAC market frenzy, we received five separate acquisition offers for tastytrade. The SPAC valuations were artificially inflated, and another suitor offered an unfavorable mix of private equity and restricted cash. IG Group in London had a publicly traded stock that we believed was severely undervalued due to market misunderstandings around their contract-for-difference business. Just as we did with TD Ameritrade, we accepted an offer that provided global market access and undervalued public equity rather than chasing paper paper-wealth promises.

When we completed our transactions for thinkorswim and tastytrade, Scott and I wrote checks totaling 50 million USD out of our personal proceeds to distribute directly to our staff. We were never legally or contractually obligated to do so. Our employees built those platforms alongside us, worked grueling hours, and believed in our vision. If a company generates life-changing wealth at an exit, the people who showed up every day to build the product deserve to participate directly in that reward.

When founders say they do not care what happens to their company after an exit, that is complete nonsense. Your business represents your personal legacy. I stayed at tastytrade for five years because I wanted the firm to be an enduring winner for IG Group, just as thinkorswim became a multi-billion-dollar cornerstone for TD Ameritrade and Charles Schwab. If someone pays you hundreds of millions of dollars for an asset, you owe it to your buyers, your employees, and your reputation to ensure that enterprise continues to thrive.

Retirement sounds like misery to me. I have no conventional hobbies; building companies and trading markets is what gives me purpose. With thinkorswim, we revolutionized financial software. With tastytrade, we revolutionized financial media. With Lossdog, we are building an ecosystem centered on mathematical optimization for careers and investment portfolios. Most people have no idea what their actual market value is in the workforce. We are using quantitative modeling to help individuals understand their true market compensation, negotiate effectively, and manage their money intelligently.

There is no corporate executive on the planet worth fifty million USD a year when the frontline workers at that same company earn fifty thousand or seventy thousand dollars. It is indefensible that chief executives collect massive compensation packages while their employees rely on public assistance for basic healthcare or food. Almost every corporate chief executive is replaceable. When executive compensation expands to five hundred times the median worker salary, the foundational social contract of business collapses.

You cannot fix the wealth gap through political legislation alone; you have to fix it through data transparency and mathematical education. We take career progression and investment portfolios and evaluate them through derivatives-pricing frameworks similar to the Black-Scholes model. By quantifying human capital, skill sets, and career trajectories, we show individuals exactly what their time and output are worth in the open marketplace. When people understand their objective value, they stop accepting severe wage discounts and gain real bargaining power.

I despise how billionaires act as though they are unaccountable for the human fallout of their decisions. How does the wealthiest individual in the world celebrate cutting hundreds of thousands of public servants or stripping food assistance from vulnerable children? I do not care if you accumulate trillions of dollars before you die; if your actions inflict widespread pain on everyday workers, you are not admirable. True leadership is measured by how you treat the people who have no power over you.

The concentration of wealth at the top has created corporate mega-caps like Nvidia and Apple that are larger than the gross domestic products of entire nations combined. Macroeconomic news, geopolitical conflicts, and political elections no longer move the markets because these corporate giants dominate all global capital flows. Capitalism has grown so massive that political democracy has become secondary to capital preservation. While the system remains resilient, the staggering top-heaviness of wealth poses a profound long-term risk.

I trade digital assets purely because they offer high volatility, which provides excellent trading opportunities. I am long Bitcoin, Ethereum, and Solana, and we are developing our own stablecoin infrastructure. However, I hold digital assets as a trader managing risk rather than as an ideological believer. You should allocate a small percentage of your portfolio, perhaps one to two percent, into volatile assets, systematically accumulating on steep pullbacks and trimming positions into strong rallies.

Do not listen to the pessimists who tell you the game is rigged and unplayable. Young people today have access to better technology, more liquid markets, and greater entrepreneurial capital than any generation in human history. To build wealth, you must cultivate an appetite for calculated risk, develop original ideas, and learn the mechanics of active trading. Avoid risking too much capital on any single position, trade small and frequently, and focus on mastering probabilities.