(Read time 6 min 43 sec)

One name appears repeatedly if you’ve been paying attention to tech and startups over the last decade.

He was the reason why I wanted to get into tech in the first place.

He is a prolific writer, interviewer, advisor, entrepreneur, and investor.

That person is Tim Ferriss.

If you don’t know who he is, his podcast The Tim Ferriss Show is approaching ONE BILLION downloads, his book The Four Hour Workweek has sold more than TWO MILLION copies, and he was an early investor and advisor to companies like Uber, Facebook, Twitter, Shopify, and Duolingo.

But what could a guy who only had one job for one year after college (which he admittedly hated) teach us about job hunting?

The answer is… everything.

His approach to how he makes career decisions is one I have adopted and has completely changed my life and the lives of the people I have coached.

And his rule set for angel investing can help you choose companies where you’ll have an outsized chance to succeed.

So buckle up, and let’s learn from the master himself.

The Anti-Career Plan

In his recent interview with legendary investor Bill Gurley, Tim was asked when did he became intentional with where he was taking his career.

His pivotal moment came after the smashingly successful Four Hour Workweek.

Instead of writing another work hacking book, Tim decided to make a complete left turn to write a book about health and fitness, The Four Hour Body.

Instead of writing the 3-Hour Workweek and pigeonholing himself into that niche, he chose to do something completely different because, in his words, “I could always go back.”

This is an important reminder whenever you decide to do something new.

When you’re considering a move to a new city, pursuing a different industry, or pivoting into a different job function, remember you can always go back.

When I quit my job in Seattle and moved to New York City with a girl I had known for less than a year, people thought that was risky.

I knew that if everything failed, I could return to doing what I did before.

So to me, there was no risk.

Remember, you can always fall back on something you have done and places you have been.

So why not go after the thing you want?

Go after opportunities that will open new doors, not the same doors you have already walked through.

Choosing Your Next Employer Like Tim Ferriss

The list of companies Tim advised or invested in are some of the most successful companies of the last few decades.

So was he just lucky?

No.

He had a set of principles that he followed.

Those principles are…

The product must be something that addresses a personal problem.

This was the key to me successfully landing a job at Uber. Seattle public transportation sucked and so did the taxis. Uber changed the way I got around the city. So when it came time to talk about why I wanted to work for the company, it was a compelling story that resonated with the team.

He must understand what it is doing, how it works, and the problem it solves.

I see this all the time. People applying for roles at companies who do things they don’t really understand. If you don’t understand it but it’s an area you want to work in, do your research. Don’t just blindly apply and hope you’ll be able to speak the language.

He must be able to be a power user of the product

If you’re a power user of the product, you’ll be able to identify ways to improve the product and customer experience which will help to scale the company. If you don’t use the product and you’re just going off the feedback of the true customers, it’s going to be harder for you to understand where you can impact the business.

He must feel very good about recommending it to his audience

I once was interviewing for a company that would make buying lottery tickets easier. The role was lucrative, but something didn’t sit right. I didn’t want to go home for Christmas and say I was making it easier for people to dump their money into a game they were less likely to win than being struck by lightning twice (You have a 292 billion to 1 chance of winning the Powerball vs a 9 million to 1 chance of being struck by lightning twice). Stick with things you’re proud to tell people you’re working on.

The people in the company must be people he wants to spend a lot of time with

The “would I grab a beer with this person” test has been slammed in the last few years, but I find it’s important. You will spend more time with these people than the duration of the average marriage. So try and find people you enjoy being around and working on hard problems with.

Use these principles to target companies where you’ll be set up for success not only in the application and interview process but having an outsized impact once you land the role.

Creating Your Own Luck

Tim consciously put himself in a position to create his own luck.

One decision that made a significant impact was to put himself where the action was.

Tim moved initially to the Bay Area, then into the heart of San Francisco.

Undoubtedly, the pandemic accelerated the acceptance of remote work.

But anyone can be remote.

You need to be in the city with an office to be more competitive than the other applicants.

Even better, be in the city where the founders are.

It’s incredibly hard to apply for in-person roles in cities where you don’t live and far more competitive to apply for remote roles that anyone can access.

So if you want to create your own luck, stack the deck by being where the action is.

Be someplace where you can attend an in-person meetup, a conference, or buy someone coffee or a drink to learn more about them, their role, and their company.

I tried to land a job in New York City for half a year before I finally moved.

It took me less than 90 days in a new city with no network to land a job doing what I wanted to do once I arrived.

The Ultimate Anti-Fragile Career Mentality

After he sold his supplement company, instead of jumping into a job or starting another company, Tim decided to angel invest.

The mentality he had as he entered angel investing is one you can adopt to develop an anti-fragile career.

This is the way to win in your career.

Don’t look at your next role in terms of title, name of company, or industry.

Instead, look at it through a different lens.

Assess your career and ask yourself, “If everything went wrong at my next company and in two years I was looking for a job again, what are the skills, experiences, network, and teachers I could exit with and know I’m far better off?”

That’s the hack.

Optimize for

• Skills

• Experience

• Network

• Teachers

Everything else will fall into place.

July is almost over, WTF?! But these 72 companies aren’t taking the summer off. They just raised over $1.9 billion and are hiring people like YOU!

Click here to learn more about those 72 companies and the positions they’re hiring for.

There you have it, lessons from Tim Ferriss that you can copy for increased career success.

Adopt his mentality to create an anti-career plan and instead focus on opportunities that will open more doors.

Pick your next company using his five investing principles to choose a place you’ll have a better chance of getting in and having a significant impact once inside.

And identify the skills, experiences, network, and teachers who would make the role worth it if everything else failed.

Adopting this mentality and these principles have made navigating my career far easier and I’m excited to hear how they impact yours.

But until then… let’s become career champions together 🏆

Kyle

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