This Guy is Ready to Escape His 9-to-5 (with help from the Upswing Lab)

Most of you are familiar with Doug, Ryan, Fried, and the other strategy wizards here at Upswing poker. They’ve built hugely successful poker careers, each in their own unique way, and some of them fairly recently. (Fried, for example, only began playing professionally in 2012—a year after Black Friday.)

Their levels of success, though inspiring, can nevertheless feel out of reach for many of us. But today we have a nice reminder that studying and grinding does in fact produce results.

We caught up with Upswing Lab member Ryan Hiller, who joined Upswing in January of this year and immediately dedicated himself to playing tournaments. Ryan has since cashed for over $35,000, with an average buy-in of under $40 as a part-time poker player. And he shows no signs of slowing down.

Ryan had some helpful and interesting things to say. Let’s dive into the interview.

What is the most impactful thing you’ve learned from Upswing?

Definitely the ‘four categories’ of hand strength concept. It’s so unbelievably important to think about what you might do with all of your hands in some given situation in contrast to what you’re doing with your specific holding at the time.

Looking back, what was the costliest mistake you were making before digging into Upswing’s material?

Over-bluffing. Which is a little bit strange, as I think most players tend to under-bluff when they first start out.

What are some of your poker goals for the next few months/years?

My main poker goal for the next few months is to transition from a 9-to-5 job in insurance sales to playing poker full time.

In the short term, I’d also like to start streaming on either twitch or YouTube. It’s a tough space to break into, but it would be nice to put some added pressure on myself to succeed. And I could do that with even just a few people watching. Thinking long-term, over the coming years my dream is to make it to the end boss games online and live, and maybe eventually play a little bit of the one house/two house games (as Doug calls them) in Macau.

Do you have a favorite poker pro, and if so, what in particular about their game and/or personality do you like most?

My favorite pro is of course Doug! (If he counts—I think he is retired or something…?) But outside of the Upswing crew I really like Jason Koon. That dude is an absolute machine on the felt. He eats, sleeps, and breathes poker. He also seems to be a super down-to-earth guy, which is impressive because it must be hard to stay humble after booking the kinds of wins he’s had recently.

Any advice for your fellow Upswing grinders?

One thing that has been bothering me recently is I see more and more poker grinders berating recreational players either at the tables or on social media. That just doesn’t make much sense to me. Recreational players are the only reason poker can still be played for profit. Most of these people are just trying to have fun playing the game we all love—don’t berate them for that!

We’ll keep in touch with Ryan and post updates here on the Upswing blog. Thanks for reading!