How Poker Taught Me How to Start a Business

When I stopped bluffing and went all-in on myself

Photo courtesy of © Pavel Danilyuk via pexel.com

Before I even began university, I started playing poker.

I used my brother’s credit card and deposited $40. That was the only time I ever deposited money into my poker account.

I started playing at night as a way to cool down after finishing my work. I’d be online for hours and hours, sometimes until the morning. At first, it was just for fun, but then something massively unexpected happened:

I started winning.

At first, it was just pocket change, but I was enjoying it. The next thing I knew, I was playing professionally, traveling to tournaments in Las Vegas, and setting aside enough money that I didn’t have to take shift work to cover my tuition fees. I learned loads.

I came to understand that all successful poker players have one thing in common. This was a lesson that stayed with me — especially when I built my first company, which was acquired just two years after going to market. The lessons I learned from poker helped make my first business really successful. Here’s the download:

What is the one thing all successful poker players have?

When I started playing poker it was just to have fun, and I wasn’t winning much.

I thought that if I wanted to learn the game, I had to learn myself. I’m not talking about mastering the universe, I’m talking about something you can actually do. I sat back and observed. I slowly began cultivating some self-awareness and emotional intelligence to understand how I made decisions. I started to play a little bit better, but I wasn’t where I wanted to be.

To take my game to the next level, I learned about my opponents. I sharpened my focus to look for “tells.” I honed my attention sharply. But this had an unexpected effect: it actually narrowed my lens. Then, it hit me, I needed to broaden my perspective — to collect all the information available to me at the time. Only then could I see what was important and what wasn’t. So, I watched how people played and began to come up with my own propensity modeling with the information I had to predict what other players were going to do.

I figured out that the one thing you need to be a successful poker player is to collect as much information as possible.

And even though this realization took my poker to the next level, this was just the ante.

Photo courtesy of © Gstudio via Adobe

What is the one thing all successful businesses have?

This lesson showed me a table with a much higher limit, and with higher stakes.

Taking the time to understand myself, the other players at the table, and take into account all the information available to me applied to much more than just poker. I began to understand that this information is also what a business needs to be successful. If businesses applied similar propensity modeling techniques to their Go-To-Market strategy, they would have an added layer to ensure their success.

And they could use this information to win big.

So, I started to think about how I could apply the propensity modeling I used for poker to the marketplace. The same way I collected information in poker, I began to look at the data industry and where there were opportunities.

In poker, I learned how to:

1. Understand myself and my reactions
2. Get a read on the other players at the table
3. Take into account all the information available to me

In business, this translated to gaining insights into:

• Products, value offerings, and Go-To-Market strategies
• The competitive landscape, competitor’s market share, and pricing
• Any white space opportunities where a product could gain market share, how much prospects spend on similar solutions, competitor’s contract information for prospects, and more

But this technology and market intelligence wasn’t really available, especially not on the same platform. Customers had to use three different programs to get this information, and this built inefficiencies.

So, I put my chips on the table and went all-in.

I saw that there were significant gaps in the information available to businesses. This was so important because these insights would allow a business to out-market, out-sell, and outgrow their competition.

How Lessons From Poker Made My First Business Successful

I saw that there were significant gaps in the information available to businesses. This was so important because:

These insights would allow a business to out-market, out-sell, and outgrow their competition.

So, I set out to find a way to make these insights available to businesses. I started a SaaS company to build a referential data set all in one platform that allowed customers to find this information. We designed what we called the “Magic Triangle” of insights: visibility of a prospect’s IT spend, who they’re partnering with, and information on contract intelligence so our customers would know when to reach out to their prospects.

We had an incredible first year, and we started to get a lot of attention.

And even though all of this was new to me — building a company, developing a platform, scaling a bootstrap brand — I had confidence we would succeed because I had the information I needed to make the right decisions. I didn’t always know the hand I would be dealt, but I knew that, no matter what, I would make it to the next round thanks to all the information I had.

These insights were my ace in the hole.

The lessons I learned on the poker table applied to the boardroom — no matter what hand I was dealt. Starting a company is not luck of the draw. You need as much data as possible in order to turn that information into insights and turn your insights into action.

Looking back, it was all about having the right insights—the winning hand that will take home the pot.