Stuckey: How I Started Betting and Eventually Made the Leap from Finance

Stuckey: How I Started Betting and Eventually Made the Leap from Finance article feature image

I would like to start off by clearing up a widespread misconception. I’ve heard some people say I came out of the womb betting on sports, but I actually didn’t place my first wager (college basketball) until I turned seven … months old. I still remember crying when everyone got excited about my first words being “mama” — but thankfully they finally realized I was saying “Monmouth.”

In all seriousness, while I didn’t make a bet on my first day or even within the first few years of my degenerate existence, I do know I will spend my last ones betting on sports. And if for some reason I ever become too incapacitated to do so, please pull the plug — and then go bet on a college basketball home dog and pour out a jug of Hendricks in my honor.

I Hate Christian Laettner

I liked to root against my dad’s favorite teams growing up. I’m sure some of you can relate, as I’ve met Packers fans who come from Bears families and Yankees fans who grew up in Boston. I’ve even met a few noble UNC fans who rebelled against their Duke family ties. Smart people, they.

Speaking of Duke (formally known as Dook, according to me) — my pops loved two teams that I absolutely despised growing up: Dook and the Philadelphia Eagles. He didn’t care as much about the Phillies and Flyers, both of whom I still root for today. However, he did love Coach K (not Rich Kotite) and the Birds.

One day, after arguing over how bad No. 1 Dook would lose to a random Southern Conference team — I said I’d bet him $20 that Dook would lose. (My first bet!) Well, I think they actually won by 40 something, but since I was in elementary school, my dad obviously didn’t make me pay. I started to do the same thing for the Eagles, who had some pretty good squads in the early-to-mid ’90s.

While it didn’t happen too often, I got $20 every time either team lost. If only gambling was that easy: Get paid for wins and push on losses.

For example, the 1992 Eagles finished 12-6 (including playoffs, under the aforementioned Kotite) and the 1991-92 Blue Devils went 34-2 en route to a national championship. Despite an 8-46 record, I profited $160. What a time to be alive!

I’m told that I cried as a 6-year-old when Christian Laettner hit his famous shot against Kentucky in the East Regional Final. And when my dad got home from the game (he sat under the basket at the Spectrum) — I didn’t talk to him for days.


I still hate Laettner and Dook, but now that I think about it, they were indirectly responsible for my first bet and shaping the direction of the rest of my life. I also don’t think it’s a coincidence I now date a die-hard Kentucky basketball fan.

Learning to Swim

As I reached middle school, I started to actually learn about spreads. So instead of betting my pops that Dook would lose to Elon, I’d ask for whatever spread I saw in the paper. For the first time in my life, I rooted for actual covers and had to pay up for my losses — usually with chores. Mowing the lawn in eighth grade after a moose was awful.

My dad also started bringing me home an extra copy of an NFL pool from a local bar to fill out. It had all of the games that week with corresponding spreads, and you had to circle which side you liked for every game. I played football my entire life and loved the NFL, so this excited me a great deal.

While most kids my age hung out at the pool, I spent my free time trying to master NFL pools.

Drowning in Pleasers

After partaking in the bar pools every week during the NFL season for a few years, I thought I had mastered sports betting. I was now a freshman in high school and ready to open an online account, drop out of school, win millions and then retire on an island with my winnings.

I won’t keep you waiting on the edge of your seats, but it didn’t work out quite like I had planned. Like many novice bettors, I got wrapped up in parlays, teasers and even pleasers.

Pleasers are reverse teasers with insane payouts. I particularly fancied three-team 6-point pleasers that paid out 17-1. For those not familiar, I’ll explain how they work.

Say I liked the following three NFL games:

  • Ravens -1.5
  • Patriots -0.5
  • Giants -4.5

Well, in order to cover the 3-team pleaser, I would have to cover the following:

  • Ravens -7.5
  • Patriots -6.5
  • Giants -10.5

I lost my shirt. And shoes. And then my socks. I know someone out there already stopped reading to go bet a pleaser. Don’t do pleasers. Please.

Find My People

One night in high school, while searching for an updated score of a college basketball game, I stumbled across an online community of bettors. I kept going back every day as just a browser and lurker. I started to actually learn about handicapping and line value.

Eventually, I started to post my college basketball bets with write-ups and built up a decent following over time. (Shout out to all of the people on Twitter who have followed me since my Covers days.)

I had countless phone calls and email exchanges with other bettors, who I considered much sharper than I was at the time. I just tried to pick as many brains as possible and tried to learn as much as I could about the craft. Bonus: I made a few lifelong friends from all walks of life from all parts of the country bonded by betting.

Worst Bookie Ever

Off to college at George Washington University in D.C. — where I think I spent more time studying lines than finance. I’m not saying I didn’t study (I graduated magna cum laude), but I just spent an exorbitant amount of time handicapping. I started to bet almost every sport, which didn’t work out well at first. I only ever had winning seasons in NFL and college basketball (my first two loves) throughout my four years at GW.

During the first semester of my junior year, I also started to take bets. But I think I officially will go down as the worst bookie to ever live. I was just too lenient and gullible to ever succeed. I would erase debts or just take partial payments way too often. On a few occasions, I even refunded bets if they got moosed on a bad beat.

After just one football season, I gave up that gig for good. I had quickly learned what side of the window I was meant for.

First Career, Second Love

After graduation, I took a summer off to destroy my liver in Dewey Beach before starting my first real job in corporate America. I loved finance — I really did — but would spend most of my free time handicapping, monitoring lines and/or streaming games.

After a few years, I worked my way up into a senior analyst role working with our international clients. That meant I could pretty much craft my schedule around sporting events.

Still, I managed grad school and became a Chartered Financial Analyst (hardest test of my life). I actually remember streaming tennis, checking lines and placing bets in between the morning and afternoon exams of Level 2 — while everyone else scrambled to cram more studying into the hour-long break. There was just no escaping my first love.

Leap of Faith

I decided to leave my finance career to join The Action Network late in 2017. Most thought I was crazy. I had spent close to a decade after college building a career, seven years in undergrad/grad and countless hours over three years to pass the CFA exam. However, those were sunk costs. Letting them hold me back from my passion in life goes against everything I had learned in those aforementioned ventures.

Plus, I could and have applied a lot of the knowledge I gained to my handicapping — from analysis to statistics to behavioral finance principles. With legalized betting on the horizon, the timing just felt right. I still remember feeling zero regrets (which would have been normal) the day after officially making the decision.

While I did ultimately chase my passion in life, which you will hear many state you should do — don’t jump without a cord. Talk to as many as people as you can in whatever industry you potentially may want to transition into and prepare for the worst.

What’s Next

I primarily joined The Action Network to help build an intelligent betting community, which I’m fully dedicated on executing. Easier said than done with all of the toxicity, but we’ll get there.

I enjoy transferring knowledge — almost as much as I like absorbing it. Longer term, I will eventually get my Ph.D. and hopefully become a professor when I retire — if I actually live that long.

I can also devote even more time toward handicapping — a craft that one can never truly master, which I think is its most alluring characteristic. And most importantly, I hope to have many more beers with many more new faces of degenerate nation. Cheers.

Photo via Matt Stamey-USA TODAY Sports