August 23, 2021

Donor Spotlight: An Interview with Tony Gregg

Meditation and the Insight Meditation Society draw people from all walks of life—from teachers, doctors, artists, and athletes to students, small-business owners, stay-at-home parents, and retirees. So why not professional poker players? Meet Tony Gregg, a 34-year-old from Columbia, Maryland, who began playing poker when he was a teenager and has gone on to earn more than $11 million in live tournament wins.

Tony is best known for winning the World Series of Poker’s “One Drop High Roller” tournament for a $4,830,000 prize in 2013. Just months before that high-stakes victory, Tony completed his first nine-day retreat at IMS, where he has now sat a dozen nine-day retreats, as well as the full Three-Month Retreat, in 2016.

John Spalding, IMS’s Director of Partnerships and Communications, met with Tony to discuss how he became a meditator, what brought him to IMS as a yogi, and why he is an IMS donor.

When did you discover meditation, and how?

I’ve been drawn to spiritual matters and to Eastern religions ever since I was a kid, but I hadn’t dived deeply into them until later in life. In 2012, I stumbled on a YouTube talk about meditation and mindfulness that Jon Kabat-Zinn gave at Google. I was struck first by Jon Kabat-Zinn’s presence, which was very calm and focused, a much different energy than I was used to. At the time, professional poker was at the center of my life, and I saw immediately that maintaining a daily meditation practice and developing mindfulness skills could help not just my life but my poker game as well.

I ordered Jon Kabat-Zinn’s book, Wherever You Go, There You Are, and I started meditating for 10 or 15 minutes at a time. Soon I got interested in doing a meditation retreat, and I found a nine-day retreat at IMS that fit into my schedule in the spring of 2013. I signed up for it immediately. Some people were surprised that I picked such a long retreat to start with, but I felt I could do it. I think nine days is a good retreat length because it takes three or four days to settle in before you get to the heart of the work. That’s where the deep stillness and true benefits emerge.

What are some life changes you’ve experienced through your practice?

Meditation has made me more aware of my thoughts and feelings, as well as more aware of subtler things that I wouldn’t otherwise notice. In terms of poker, meditation made me more present at the table and gave me a better handle on my emotions. When facing a critical moment in a tournament, for instance, I felt more grounded and wouldn’t get as overwhelmed by the magnitude of what was at stake. Or if I lost a big hand, I became good at letting go and moving on, maybe not always, or completely, but I was much better at it than I was before I had a practice. And once meditation became a part of my life, the people I played against in tournaments knew there was something different about me, and some were intimidated by those changes. In fact, the tournaments I played in over the months following my first nine-day retreat were the most lucrative of my career. That was not a coincidence.

After your first IMS retreat, you continued to play in big poker tournaments around the world, and yet you managed to come back to IMS to do a couple of nine-day retreats every year. And you did the Three-Month Retreat in 2016. Three months is a serious commitment, a long time to be unplugged. How did you make it all work?

The longer retreats, especially the Three-Month Retreat, appealed to me from the very beginning. The first eight months of 2016 were busy for me. I’d been traveling around for big tournaments all winter and spring, and then I lived with friends in Las Vegas over the summer during the World Series of Poker. After that, I went to IMS to do a nine-day retreat in August. I really enjoyed the experience, and I really enjoyed being at IMS, and I saw that the Three-Month retreat was starting in September, a couple of weeks away. I realized that, other than a few more tournaments I thought I’d go to, I didn’t have anything that I really needed to do that fall, so I signed up for the Three-Month Retreat, winding up on the waitlist, at number five or six. I thought, “I’ll never get in,” and I sort of put it out of my mind. Then, a few days before the retreat started, I received an email saying I made it into the Three-Month. This blew my mind, and I got very cold feet. For a good 12 hours, I wasn’t sure if I was going to follow through. Then I thought, I may never get this opportunity again, and I knew I would regret it if I didn’t do it. I kind of wished I had more time to prepare myself for it, but I did it anyway.

What was the Three-Month Retreat like for you?

At times, it was a grind. I’m not sure I expected that part of it. But I definitely had some very deep insights during those three months of silence, some incredible moments of clarity and insight that I had never experienced before, or that I have experienced since. That’s definitely part of what keeps me on this path—having new experiences on the cushion that allow you to enter a mind space that you never knew was possible before.

After the retreat, I had a hard time integrating back into the world. In the final weeks, the teachers kept warning us that we needed to take everything really slow and easy as we returned to our everyday lives. I don’t think it’s that I didn’t believe them when they said this. I think I just didn’t take it as seriously as I should have. Going back into the world was a lot harder than I thought it was going to be. But overall, I had an incredible experience, and I would do another Three-Month Retreat if the opportunity arises again.

Do you still play poker?

I still play, but not nearly as much as I used to. A couple of things changed. For one, the pandemic hit and I was basically stuck at home for 18 months without an outlet to play poker. But there was also a shift in the game that really began around four or five years ago with the prevalence of “solvers,” which are computer programs people use to study how to play any possible hand combination, what percentage of the time, in a game-theory-optimal way. The more people studied with solvers the harder they were to beat, and there were players at the highest levels who were using these solvers all day long when they weren’t playing in tournaments. That kind of studying never appealed to me, and it gave my opponents a confidence I didn’t have. It changed the game for me, and I lost some of my passion for poker.

Although I’m still relatively young, I’m definitely no longer part of the younger generation in the world of poker. I’d been playing poker my entire adult life, even longer than that, since poker became the main focus of my life when I was a sophomore in high school. I recognized that this next generation is hungrier than I am, and with the edge they have using these solvers, I felt like poker was passing me by. In poker, you have to put up money to play, and if you don’t have an edge on your competition, you’re going to lose money. So I took a step back from the game. I was used to being one of the best players playing in the highest stakes tournaments in the world, and the thought of playing in lower stakes tournaments didn’t get my blood pumping. I decided I would rather move on to something else, while still playing in certain tournaments every now and then, even if not at the highest level.

So what are you doing these days in lieu of poker?

For the past year and a half, throughout the pandemic, I’ve gotten into investing. Not day trading, but swing trading—that’s the strategy I follow. I’ve found that my strengths as a poker player serve me well as an investor, and I think that having a daily meditation practice, which has made an enormous difference in all areas of my life, has helped me to be a wiser investor, as well. Other than that, I have a new puppy, named Zen Master Roshi, who keeps me busy. His energy is all over the map. He’s either going 100 miles per hour or he’s taking a nap.

What has it been like for you not to be able to do residential retreats during the pandemic? Have you found online programs helpful?

Last year was tough for me, and I definitely missed the benefits of doing a retreat at IMS, big time. I did do an online retreat, which was fine, but there’s no substitute for the kind of reset you can get through a retreat on-campus. You show up at IMS, and you hand over your phone. As someone who’s either on my computer or my phone all the time, that’s huge for me. I can easily get stuck scrolling through Twitter aimlessly, or fall into a black hole watching YouTube videos or reading mindless news articles that do nothing constructive for me.

With IMS closed during the pandemic, I really grew to appreciate how much I get out of being on a retreat, and out of practicing with other people on retreat. I get inspired by their dedication. There’s just no replacement for residential retreats.

I’m excited about IMS reopening. I’ve never sat at the Forest Refuge before, and that’s what I’d like to do next. I visited the Forest Refuge after a retreat at IMS once, and I was really impressed with the peaceful grounds, the meditation hall, everything. Ajahn Succitto is on the calendar to lead a month-long retreat at the Forest Refuge next November-December, and I hope to win the lottery for it. I’ve done a retreat with Ajahn Succito at IMS’s Retreat Center before, and the way he presents himself and his style of teaching really resonates with me.

What inspired you to become an IMS donor?

I have a great respect for what IMS does and for the value these programs add to the lives of everyone who gets to experience them. I have benefited so much from the retreats I’ve done—I consider them priceless—and I’ve wanted to show IMS my appreciation. I’ve also wanted to do my part to help make these experiences possible for those who otherwise wouldn’t be able to have them.

Funny, I’ve seen IMS change a lot since even my first retreat. I was there the year IMS was building the Bodhi House dorm, and I was on one of the last retreats where people still shared a room. So I had a roommate on my first retreat, and I actually found it to be helpful. Having a roommate kept us both in line with the schedule, since neither of us wanted to be judged by the other for sleeping in or skipping a meditation period! [Laughs] But it’s been great to see all the ways in which IMS has grown since then, and to have contributed in some way to its success.