Some Sh*tty Career Advice From A Professional Gambler

Asymmetric betting, skill acquisition and daring to be different

Sorry for shipping a day late.

I’ve been at London Tech Week and Mailchimp’s marketing conference. I’ve barely had a minute to myself.

There has been a lot of chatter at both events on purpose, community and AI.

I wonder how much of this is a fad?

Anyway, on to today’s newsletter…

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Hey Friends,

Quite a few people have asked me for career advice lately. 

Personally, I don’t think I’m qualified to be giving any sort of advice. 

Let me give you a highlight reel of my CV:

• Parent’s Chinese takeaway (2006-2010)

• BSc Psychology (2010-2014)

• Professional poker player (2010-2015)

• Lloyds Bank Analyst (May 2015 - Nov 2015)

• Professional poker player (2015-2021)

• Freelance E-sports photographer (2018-2019)

• Poker and Mindset coach (2017-2020)

• Starting PhinPhin Coffee (2021-2022)

• Investor (2019-)

• Online writer (2020-)

• Freelance copywriter now turning into marketing & advertising agency owner (2021-)

I’ve never had a career counsellor or plan. I’ve just followed my curiosity and made it up as I went along.

The way I see it, most people are thinking about the whole career/job situation in the wrong way. They care more about maintaining their job and salary than expanding their careers.

To explain what I mean, let me tell you a quick story: 

When I was on the cusp of starting my coffee business, my ex-girlfriend – in the last argument before we broke up – asked me, “What the fuck are you going to do if you fail at the coffee business? What job will you get if it doesn’t work out?” 

1) I didn’t know.

2) I’m unemployable — in the sense that I’ve tasted too much freedom — so getting employed was off the table for me. (I will caveat that I’ve changed my mind on this. I’m happy to take a job so long as I’m given autonomy).

To further increase the risk, I was adamant about not returning to poker either. I thought the industry was dying — poker bots were becoming more and more prevalent. I felt that if I stayed for a few more years and exploited what was left it’d be too late for me to learn new skills by the time I got out.

Honestly, I don’t blame my ex for wanting to end things. My strategy was a little extreme: leave everything behind, have no income, and try and do something new.

Yet, there was something she didn’t understand but was super obvious to me: Starting a business has a job risk – I lose a stable and secure income (even though I was a poker player, but humour me for a second and let’s pretend it’s ‘stable’ and ‘secure’) – but it has little career risk.

I saw starting a business as a huge asymmetric bet. If — and that’s a huge if — I was successful, then the upside was unlimited. And if I had failed, I would’ve lost a bit of money but acquired a vast range of skills: Finance, marketing, sales, communication, negotiation, project management, problem-solving, relationship building and leadership. 

The mistake people make is not understanding that taking more risks, especially when benefits are asymmetric, creates more optionality. 

I know I spoke a lot about the pros of starting a business, but I understand it’s not for everyone — Nor should it be. I also understand that people have expenses to pay or a family to look after or simply can’t afford to quit their jobs.

But the point I want to really emphasise is that it’s far more important to keep learning new skills. This will help derisk any threat of job loss.

The more skills you learn in a competent manner and are able to stack, the rarer you are and the more valuable you will be.

An example of this is my Twitter buddy Andrew Lynch. He write’s Net Income. It’s a newsletter on the financial analysis of great businesses. Sounds boring, right? However, he’s stacked his writing skills on top of his financial knowledge, and what you get is great storytelling and edutainment.

Last year a writer friend told me, “Oh, I would love to play the guitar, but it’s such a waste of time and won’t make me any money.” This is the wrong way to look at things. Not every skill will make you money, but it can compound into something useful. What my friend failed to see was that learning the guitar could inject more rhythm into her writing.

Skill acquisition is never a pointless endeavour. You just don’t know when, where or how the skill will pay off in the future.

That’s the brilliant thing about asymmetric opportunities and skill acquisition. They have a meaningful upside in the event of success. And a meaningful development in the downside case. 

It can also involve taking a bet in a risky space that other people are too scared to pursue. 

A friend of mine is leaving his project manager role here in the UK to work in a legalised marijuana startup in Canada as employee number 1. This looks and sounds dumb and risky.

But I think it’s one of the greatest asymmetric opportunities I’ve seen in a long time. Frankly, I’m a little envious. My friend gets to learn new skills, develop specialised knowledge and experience the beginning stages of a business. His potential for career growth is huge. When he returns to the UK and if the government decides to legalise marijuana, my friend is in an incredible position to take advantage of the opportunity.

“There are no dumb ideas. Only early ones.” — Marc Andreessen

Even if he doesn’t start a business and decides to return to the corporate world, he has a unique experience on his CV that will help him stand out from the crowd.

Many ambitious people, even though they understand how smart risk can open doors, still would rather take the conventional path and hoard optionality. I see it all the time, especially here in London. They accumulate options for the future instead of exercising them and figuring out what they really want to do and doing that instead. 

It sounds something like this: 

“I don’t know what to do with my life, so I’ll pick an engineering degree. That will allow me flexible career options.” 

“I don’t know what to do with my degree, so I’ll do a postgraduate degree. That will allow me the option into a higher paying prestigious job.” 

“I don’t know what I’m going to do with this post-grad, so I’m going to get into management consultancy to ‘figure out’ what I truly want.” 

Why does this happen? Because people don’t want to look silly. As John Maynard Keynes once said, “Worldly wisdom teaches that it is better for reputation to fail conventionally than to succeed unconventionally.” 

But here’s the thing. If you and every ambitious person are doing the same thing, and by that I mean going to an Ivy League school, attaining a prestigious degree, a few extracurriculars, and a job at a big corporate firm, you can’t accumulate optionality through conformity, only through differentiation.

Taking conventional paths may cap your downside, but it also caps your upside too. 

You have to take a risk and be willing to look dumb for a long period of time. Take high upside bets others won’t take, and keep trying when your last bet doesn’t pay off. 

I’m sure some people I meet will think this newsletter is a dumb idea. To them, it looks like a waste of time. But they fail to comprehend the asymmetric bet I’m placing. If I win, I will have a successful media asset in my hands. If I fail, I will have built incredible connections and sharpened my writing and storytelling skills. Heads, I win. Tails, I win.

Admittedly, this insight has only become obvious to me in the last few years, and even then, it took multiple people to point it out to me. But my poker background has given me an ‘ace in the hole’ advantage against the field. I didn’t know it at the time of starting, but poker has given me incredible insights into human behaviour, which in turn has helped me with advertising and marketing. I think this is what Steve Jobs meant when he told Stanford’s 2005 graduating class to “stay foolish.” 

One of the last things my ex said to me was, “You like to be different.” 

She’s right. I do.

As Kevin Kelly once said, “Don’t aim to be the best. Be the only.”

— Jason Vu Nguyen