How poker helps you win at product management

A lot of product managers start their careers as engineers or MBAs. I started my career as a poker player. I wasn’t poker player then a product manager. Poker directly inspired me to launch my first product: an online poker community. And while Roadmunk, my current company, has nothing to do with poker, I would never have levelled up if it weren’t for the game.

My poker story started the same way as many others: a bunch of dudes playing for $5 in my friend Dustin’s basement. But as I honed my game and started to win big online tournaments, I also honed a lot of the skills I now use daily as an entrepreneur and product manager.

Some of the similarities between poker and product are obvious. (And Shopify’s Brandon Chu has already written an awesome post on the same topic.) Both require endurance, risk calculation and chill under pressure. But I wanted to share some of the other, less-obvious facets of poker that have shape my career in product.

#1 Nurturing luck through collaboration and feedback

Poker players aren’t always straight-faced loners. In fact, poker is insanely collaborative.

I met Steve B., one of my poker mates, through a mutual friend in biology class at the University of Waterloo. Steve gave me the lowdown on how to win — and consistently exploit opponents. Hand analysis, habit-building and pattern recognition were all quickly part of my repertoire. Steve was about my age, but he had a few extra years of poker under his belt. It was largely thanks to him that I won my first tournament in 2004 after only 6 months of play — and took home a tidy 30K score.

My poker friendships taught me a counterintuitive lesson: luck isn’t pure luck. It can be nurtured — you can actually grow your luck. Both product management and poker require a mix of luck and skill. There’s certainly an element of “getting lucky” — but you can cultivate good luck through constant collaboration. What I loved most was how feedback was often conflicting. I had to learn when to follow advice — and when to forget it.

In the business world, we call that mentor whiplash. When you take bad poker advice, the stakes aren’t usually disastrous — losing a single hand or tournament may sting, but there’s always the next one. In business, on the other hand, it can take weeks (or months) to course-correct after making a bad decision.

Since my poker years, I’ve learned to nurture luck by surrounding myself with smart people and reading tons of books. (I tend to devote about 25% of my energy to books,25% to mentorship and 50% to actually doing it.) By the time I became a product manager, any ego had been replaced with a humble understanding of my own ignorance. Poker had set me up for a product management career filled with healthy collaboration — which increases your chances of success.

#2 Optimizing for states of flow

I had my all-time best poker day during a tournament in Aruba in 2006. Even though I didn’t win, my focus was powerful. I could basically feel everything that was going on at the table. All my reads were perfect. And I recognized that if you can attain that level of concentration, you won’t always win, but you will get closer to your goal.

Poker is a discovery of different states of mental solitude. Initially, there are hurdles — you swing a lot between winning and losing. But along the way, your focus gets deeper as you hone your skills and build confidence. You learn to ignore everything that’s going on outside the table. Given the nature of the game, this does not guarantee success — but it definitely increases your chances of winning.

Building a product requires countless states of flow. (Be sure to check out Mihaly Csikszentmihalyi’s work on flow.) Email, conversations, snacks, last night’s fourth beer — you need to be able to shut that out, clear your desktop, and concentrate. (Personally, I like to avoid email for the first two hours in the morning and tackle at least one “boulder” task per day.) With flow comes deeper insights that enable us to move faster and make better decisions. Regardless of whether you happen to be winning or losing on any particular day, you need to be able to quiet the noise and zoom in on your goal.

#3 The data is a story, not an answer

In online poker, especially, your ability to read your opponent is correlated to your ability to read data. Poker players use something called a HUD (i.e. “heads-up display”) that aggregates players’ stats and hand history. High-value stats includes an opponent’s VPIP (how often they voluntarily put chips in the pot) and their AF (aggression factor).

The challenge is that the numbers are not always straightforward. If an opponent knows your stats (which they do, because they’re always using a HUD, as well), their behaviour will change. Their actions might also be affected by table stakes, game type and their mood on any given day. So while the numbers tell one story, the reality can vary wildly. You need to be able to read the numbers within the context of the moment. Just how in business, you must understand (and predict) how a market or competitor will respond to certain activities.

While the numbers tell one story, the reality can vary wildly. You need to be able to read the numbers within the context of the moment.

In both poker and product, no amount of data can replace instincts. In the early days, PMs often don’t have a lot of data — they just have instinct. They must extrapolate from users’ anecdotes and opinions to create an early vision for the product. And even when you have tons of data, it can’t be your only reference point. When we started Roadmunk, my instincts told me to emphasize design. There was no quantitative evidence saying we should be a design-led organization. I just knew, intuitively, that design was going to be very compelling. I may not have trusted that feeling if it weren’t for poker.

#4 Emotional Intelligence

The final piece of the puzzle seems to be the never-ending virtue of emotional intelligence. The idea of a “poker face” kind of misses the point. Being a great player doesn’t mean masking your emotions, but learning to harness them. Remaining stoic at the table requires a deep well of confidence, humility and determination. For most, early on, it’s just about winning that one game. Then it’s about continuous flow and ultimately growing to be the best.

To be present to that fire, understand how big it is, and be objective towards it — that’s where the 0.01% live and breathe.

In business and poker, leaders lose years due to internal stress because they have to remain outwardly calm. To bridge the gap between internal and external realities, you must have emotional intelligence. The fire will always be burning. Sales will always be yelling for the “next thing,” engineering will always be under pressure, and product managers will always have to be the go-between. To be present to that fire, understand how big it is, and be objective towards it — that’s where the 0.01% live and breathe.

For product managers, getting to that level is incredibly challenging because you need to fail and learn from mistakes made with REAL businesses in REAL markets that cost a lot money. Much like poker, it’s not for the faint of heart.