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How a High Stakes Poker Player Became a Financial Advisor

Kyle Ray | September 5, 2024

TL;DR

The poker industry was booming when I started college. I climbed the ranks with dedication, hard work, and an understanding of game theory. As my profits grew and the action slowed, I started investing to secure my future. This led me to discover a passion for helping others with their financial planning. It provides me with a greater sense of purpose than poker ever did. I established Ridgeback Wealth Management to assist people in making sound financial choices. I opted for a flat fee and hourly model to ensure investors benefit from new technology and powerful economies of scale instead of those benefits going to investment advisors, mutual fund families, or brokerages.

From Professional Poker to Financial Advisor

Poker started as just a hobby, a late-night hangout with friends in high school. The World Series of Poker on ESPN began showing player hole cards in 2003, which aired all summer long before my senior year of high school. Everyone wanted to try the game. I would grab a new strategy book from the bookstore weekly to learn how to beat my buddies out of their summer wages.

When I started college, I had accumulated a good amount of money from those games and wanted to test my skills at higher stakes online. It took me a year or two to find my groove in Limit Hold'em, but eventually, I began to make substantial profits, enough to drop out around 2009 and focus full-time on poker. Playing online was much different from playing live games with friends. One can play many more hands quickly, and I promptly accumulated millions of hands of experience.

The Mathematics of Poker (TMOP) was a groundbreaking book released in 2006 that profoundly influenced my approach to the game. Most poker books at the time were recipes for how to play individual hands based on specific game conditions and how to calculate basic odds. TMOP employed quantitative analysis and game theory, using simple toy games and the concept of Nash equilibrium to address crucial questions about 'optimal' player strategies.

For those unfamiliar with poker or game theory, think of this approach as attempting to map out your entire game plan in advance, assigning every possible hand a value between 0 and 1, with 0 being your worst possible hand. Your actions (betting, checking, or raising a bet) all give away information to your opponent(s), hinting where your current holding lies in that range. Therefore, you want to find balance in your actions to hide information and extract as much value as possible.

Digesting and applying this approach got me a good way, but the real breakthroughs were in collaborating strategy with other poker friends or hiring coaches who adapted this approach. I even later decided to coach poker myself, both one-on-one and in recorded videos for a well-known training site, which, on its own, was a valuable way to improve.

Later, I discovered that there were computer competitions where bots would utilize machine learning to develop advanced strategies. From then on, my approach would start by analyzing how computers play. In the early 2010s,  we players and developers crafted strategies in secret to capitalize on profitable opportunities. Many poker training sites today offer versions of these computerized strategies for learning and analyzing hands.

After changes in US laws and regulations post-2011, I moved to Playa del Carmen, Mexico, where I legally accessed poker sites outside the USA. However, high-stakes games became less available after 2014, and I could only find them once or twice weekly. With fewer hands being played, the emotional impact of wins and losses grew more significant. Maintaining a consistent income from the game without hand volume became challenging. The opportunity cost of keeping large sums in a poker bankroll instead of investing for the long term was becoming significant.

After realizing the importance of managing my finances and making wise investments, I became interested in my own financial planning as a new challenge and a way to secure my future beyond poker. With ample free time after the decline of high-stakes action, I enrolled in online school to complete my undergraduate studies and pursue a Master's in Financial Planning, which took me further away from the poker tables. The skills I honed in poker, such as risk management, strategic probabilistic thinking, decision-making with uncertainty, and data analysis, remain invaluable today.

Despite getting a master's degree, I felt conflicted about the financial services industry. When I met with financial advisors about my situation, they all wanted to charge a percentage of my total assets. At a staggering cost of $30-40K a year, my research showed they were unlikely to achieve better investment results than I could with ow-cost index funds. Additionally, I did not expect them to have a better temperament for dealing with market volatility than I do as an experienced poker player.

I later realized that quality financial advice goes beyond deciding which portfolio to own. It can encompass tax planning, cash flow planning, family and education planning, and more. There can even be an element of life planning whereby uncovering your values and ambitions can lead to better financial decision-making.

After considering my life plans, I was inspired to shift my focus towards a career as a financial advisor. Initially, my financial planning was basic and mainly focused on my needs. However, I hadn't fully considered the additional financial responsibilities of having a family, such as saving for my daughter's education and funding family vacations, among other goals. The appeal of early retirement diminished as I yearned for the engagement and fulfillment that purposeful work provides. Personal finance offers me a perfect blend of interest and challenge. Additionally, there has never been a better time to be a solo financial advisor, thanks to the development of software and advisor support networks. This is a career that keeps me mentally active and allows me to impact others' financial well-being positively.

Daniel Pink's book Drive explains human motivation's three aspects: autonomy, mastery, and purpose. Poker provided me with the satisfaction of mastery and autonomy in work life, but it lacked an overall purpose. Financial planning and helping people manage their money effectively touches everything and everyone. Though I occasionally play poker during the summer at the World Series of Poker, poker is once again just a hobby.

Since 2018, I have been working in financial planning, gaining experience and continuing to learn. With the launch of Ridgeback Wealth Management, I am eager to assist individuals and families in living their best lives by effectively helping them plan and manage their money.