How to Become a Successful Entrepreneur after a Poker Career?

Former poker player Tom Page is now the owner of a successful startup company developing a job matching application. The app is the first of its kind on the market and also is the most widespread, while being constantly developed. But how did this progressive career start?

Tom Page

Page had been enrolled in a poker career in the best possible period: in 2004, he deposited $25 and turned it into $6,500 in a single month and made enough money in his career so that it should not be a concern for him anymore. As it happens, however, Page had never intended to remain a poker player forever, which he explains with a unique reason: “I see it as being worthless to society. You are not creating any value, and that isn’t important to everyone, but it’s important to me.”

In April 2012, British-born Page moved to Silicon Valley and was working on introducing a product, Playtagit, which he ended in November that year. Taking also a number of healthy issues into consideration – lost a lot of his hearing in his left ear and a moderate visual impediment later, both eventually cured by medication – he was at a loss at the time as to what to do next.

In the end, he did make a decision: based on the overlap of the required skills, Page was determined to enter the Venture Capital industry. Among the recipients of his application e-mails was Sequoia Capital owner billionaire Michael Moritz. His message read as follows:

“Hi Mr Moritz,

My name is Tom Page, I’m 26, I’m originally from Wolverhampton, England, but I graduated Oberlin College in 2008 with a degree in Economics and Philosophy.

I played online professional poker for 6 years, and was ranked within the top 500 players in the world.
For numerous reasons, I decided I didn’t want to play poker professionally forever and entered the world of technology last year.

I founded formed a team, made a bunch of mistakes, learned a lot and was moderately successful, but am in the process of selling the software and moving on.

I want to get involved in Venture Capital, and am willing to do whatever it takes you to get started.
When given the opportunity I believe I’ll excel for these reasons.

To those that played poker against me, they know that I am able to make good strategic judgments, and that I am reasonably clever, but most importantly I also work very hard. These traits were at the roots of my poker successes.

I’m a genuinely social, outgoing individual which causes me to meet and get to know a lot of people personally, which results in building a very strong rolodex.

I myself, invested in other poker players. I personally found and attracted the best deals that were available by specializing in specific forms of poker. A world that is not far away from operating within Venture Capital.

I brought more to the table in terms of value than other players. That itself, gave me a real life grasp of the formula that one needs to go through in order to be a successful tech VC.

I strived long and hard at learning the craft of poker. I would like to use these skills to try and become a very good venture capitalist.

Would you be willing to meet with me and talk more?



Somewhat surprisingly, Page did land the interview. After spending the next week preparing for the meeting and resisting his friends, who were trying to talk him out of it, he arrived at the first job interview in his life, at the age of 26. Shaking hands and Moritz not saying anything, Page started talking about himself and his suggested ways of contribution to Sequoia – while keeping eye contact for 25 minutes straight, a valuable attribute of a live poker player.

They went on to ask each other questions on Moritz’ initiative, the latter’s queries including “What weaknesses do you have?” “Where do you see yourself in 5 years?” “What companies do you want to invest in?” And then the interview was over.

Page did not get the job.

How he thinks about it, however, is well worth taking note of: “I look back on my interview with several thoughts. A part of me is disappointed at the rejection, but it’s a part of life. Another part of me is annoyed at myself for not being good enough so that it would have been a no brainer for Sequoia. Always blame yourself is my motto.”

Eventually, from the money he had made on poker, Page started his own business,, a job matching application for employers and applicants: both browse the others’ offerings and where the two parties say yes, the app sets up a chat conversation. The software is today the most popular of its kind, and also the first, so the startup is looking towards a bright future.

As his story appeared on TwoPlusTwo, the community endorsed Page and he was happy to join the discussion himself under his ‘sigurrostyp’ screen name and to reply to users’ comments and questions.
While some readers complained that the story does not make sense, Page argues that his intention was to give hints at how to get the attention of the employer, even a well sought-after one. He also responds to voices saying he should have used the meeting for networking by saying that you need to be wanted by the company for them to make sense to recommend you to another one in the same industry.

When asked about a piece of advice he would have given himself to have a better chance at the interview, Page replies as follows:

“I wish I knew more about technology back then in terms of analyzing what companies have a higher % chance of becoming a unicorn. Sequoia looks for competitive advantages on their opponents, and if you know something about a specific technology and why it is going to make one company become a multi billion dollar operation in a few years then they'll want you.”

While his letter is probably not written well enough to be an example to follow, one can definitely learn from Page’s determination, initiative and creativity. His story is a great example of how to become an independent, successful entrepreneur who contributes to society and makes a living with it; it is a reinforcing thought for poker players and others alike to be able to do this, so let us keep his advice and stay pathologically optimistic!