BerandaComputers and Technology7 Things I’ve learned after 10 years of trying to make it...

7 Things I’ve learned after 10 years of trying to make it on the internet

James Clift

I’ve been playing the technology company game for over a decade now.

In that time, I went from a 20 year old kid who had no idea what he was doing to a man with a much fuller beard who has no idea what he is doing that happened to sell millions of dollars of software.

I don’t often reflect on absurdity of it, but it is absurd.

Weirder still, I’m the least impressive of my friends in this world — I’ve had the good fortune of being surrounded by people who started off exactly like I did build massive companies with hundreds of employees.

As a kid, the only jobs I knew of that “rich” people had were doctor, maybe lawyer, and that scary kid who’s dad was probably in the mob. Becoming a millionaire was not imagined, nor even discussed. Yet, here we are.

Here are a few things I’ve learned from a decade of trying to make it on the internet.

Bet on yourself, but make sure it’s actually a bet

The low point of (one of) my first companies was being so desperate for revenue that we adapted our virtual job fair platform to become a virtual business directory for a small town. For $2000/yr.

There is no upside to that. We essentially became a horribly paid consultant for an industry we didn’t care about with a product that didn’t add any value.

Limping along for years while eating ramen and pitching a VISION isn’t success — you’ll be much worse off than if you had just worked for a startup for a few years to improve your skills and peers.

To truly bet on yourself while starting a company, everything you do should accelerate any of the following:

  • Learning new skills: sales, product management, product development, engineering, marketing, design, fundraising
  • Meeting great people — not in the “I shook Mark Cuban’s hand” sense, but in the “I have 5 equally motivated people in my corner building shit that I can text about the fact that we won’t make payroll next month.”
  • Making money on your own time
  • Travelling or experiencing the world through a different lens (though in 2020 you should just get a remote job)

Build your tribe

You don’t need mentors. You don’t need investors. You need 5 friends with similar ambitions trying to figure this shit out with you.

You want people that you can call when your world is falling apart. When you want to quit. When you hate your co-founders. When you’re questioning everything. When you’ve made the money, but don’t feel good about it.

It is a weird, un-relatable world that we’re playing in. To navigate it, you need people that understand. I’m so lucky I found my people.

I don’t have great advice on how to find your people.

Join a co-working space? Get into a startup accelerator? Join a program like On Deck? Message people on Twitter?

Just launch something

I know many people who are much more talented than I. They’ve got better ideas, more technical skills, and are just plain smarter.

What they don’t have is that forcing function that compels me to launch stuff.

The shamelessness. The not-give-a-fuckery.

To not quit when I want to quit. I’m not sure that “chip on the shoulder” is all positive, but it’s probably necessary.

It’s a learned behaviour. I don’t come by it naturally. I hate failing. I suck at getting feedback. I’m overly sensitive. And yet, here we are.

It takes 3 years for anything to work

Every successful company I’ve seen has taken at least 3 years to get some hint of product market fit.

Dig deeper into every company that takes off overnight — it’s probably a pivot from something else, the founder’s 8th attempt, or a hail mary. The one thing that truly worked for me was about 3.5 years in.

That specific thing worked in month 2, but it took 3.5 years of learning to get to that point.

Check your ambitions

My original goal when starting out (Thanks Tim Ferriss!) was to “build a business making 10k a month so I could work from anywhere.”

I got there, and enjoyed it — lived in multiple countries, didn’t work too much, drank great wine and ate incredible steak. It wasn’t enough.

Financially, it didn’t matter. The cash was enough, but a life of leisure isn’t a great goal for a 30 year old. I stopped growing, learning.

Ironically, that guiding goal held me back. What seemed ambitious at the time led to unambitious decisions, like first building a below average web design company. It also led to coasting when cashflow was (very) good.

I somehow managed to reverse engineered my version of success, but unfortunately financial success is always a moving target — especially once you have something that works.

What would have been a better focus is building an exceptional product, an amazing team, and continuing to grow as a leader.

If you can solve for those things, the score (and the cash) takes care of itself.

That said, if your goal is to build a company that makes 10k/mo that allows you to work from anywhere — go for it, goddamnit.

You will want to quit

Building something from scratch is hard, and having a job will often sound very appealing.

Here’s what you need to do today, and here’s your paycheque!

Starting a company has infinite variables. At the early stages, you’re pushing a boulder up every hill you can find. You’re trying to find that one thing that gathers enough momentum to allow you to survive another day.

If you’re lucky, you’ll get to a place where you’re no longer trying to survive — you’re trying not to die. There’s a difference.

Every day you will have an infinite to-do list, none of which is certain.Take your best guess at what the most important thing you can work on is.

Do that thing, and try to ignore everything else.

Don’t forget to manage your psychology along the way. At the end of the day no one cares if you fail, and it’s not that important. Have grounding forces in your life (sports, family, knitting) to help keep you sane. Try not to build your whole identity around your company.

(You won’t do any of this, but I’m hopeful this will help you realize you’re not the only one.)

You might surprise yourself

Most people who reach unheard of levels of success are probably not that much smarter than you, and they probably don’t work that much harder.

Granted, there are ridiculously smart driven people that operate on another level (Elon Musk, The Collisons). They’re likely going to be trillionaires.

I’ve met many people who have built $100m+ companies that are very smart and work very hard — but probably not that much harder than a Senior Engineer at Amazon. Success is a result of talent, hard work, and luck.

If you’re smart, want to work hard, and care about building a business one day — the best place to put that energy is into creating something new.

You can’t get lucky if you’re not in the game.

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