Uncertainty, pictured left. Entrepreneurs, right.

This past summer I walked into my office and there was a subpoena from the United States Department of Justice on my desk. Another from Google’s antitrust defense team.

Seemed my little dinghy had been swept up in the federal antitrust case.

It wasn’t my first priority to deal with that day. I had more pressing shit to do.

I figured, like many times before, that I’d see my way out of this one. And maybe even try to squeeze something good out of it.

…

Building a company is like playing a video game where new and weird goons pop up at each level. I’ve made it far enough that I’m “successful” in a lot of people’s eyes. Of course, as far as I’m concerned, I’m not even halfway up the mountain. And to others, I’m a meaningless pipsqueak still unworthy of recognition on the plane of existence.

At one time (12 years ago), I was a bright-eyed startup wannabe trying to pitch USV, applying to Y-Combinator and TechStars. Rejected from all. I was adorably stupid and undeterred. I decided to bootstrap. A grand adventure awaited.

Looking back, as challenging as it can seem, I wouldn’t trade the experience for the world — everybody who’s made something resembling “progress” feels inclined to share some tips for the journey.

If you’re new to this, here’s my guess: You, like me, will read this and ignore virtually any good advice. But read it anyway. Maybe it’ll be helpful on your journey.

And in the words of Wu-Tang, I’m gonna give it to yeh raw.

These are the stages of bootstrapping a startup.

ONE LAST THING. If you want to greatly improve your odds of moving through these stages, particularly the middle to later ones, you should be doing these things:

Reading and learning: All the stuff you need to know was put in a book by someone who’s been there before you. The knowledge of the world is out there for you. Don’t be an idiot and ignore it.
Connecting with other founders: Connect with people at your stage, and people preferably a stage ahead of you. Learn from them. A maybe even one person who’s super far ahead — a mentor. Be humble. Share your failings and challenges. They’ll help if you’re sincere in asking. If you want to meet other founders, well, I’m typing this on a flight back from SaaSAcademy’s Intensive in Austin.
Working on yourself: If you want to be good at a sport, train like an athlete. The mind works in tandem with the body. Work on growing your relationships and your role in your community. Work on you, but don’t forget that it isn’t all about you.
Work on others: As you make progress, help others along the way — especially those who are sincere in asking for your perspective or help. Do it with no expectation of anything in return.

1. Idea

This is where most startups die. Cool idea, perhaps among friends, lots of talk — nothing ever gets off the ground. Probably better that way because those fuckers don’t execute.

2. Start Something

Ah, action. Developers are good at this. Start building out the prototype. Build all the hard parts and neglect to build the boring-but-necessary parts that makes it usable or presentable — let alone saleable.

Since building the “hard part” was also the fun part, they’ve lost interest and moved on to another project.

They gave up at the first sign of a real challenge — just sticking with it.

This one fizzles out.

Probably better that way because those fuckers don’t have the grit to follow through.

3. Finish Something

Holy shit, a completed project. You made it through the boulevard of broken dreams!

Hopefully, you’re ready to learn an entirely new skillset because you have to learn to sell, and if you want any preview of what’s to come, you’re going to suck at it.

At least for a while. Or maybe you’ve got a “business” co-founder who can sell. That would be sweet.

On that note …

4. Sell it to Somebody

I hope you didn’t just build some cool shit without ever actually asking anybody if they thought it was useful.

If you did, I hope you didn’t ask people who were going to tell you what you wanted to hear.

A lot of ideas die here. This is where some serious blows to the ego take place.

They hurt a lot more if you initially thought you knew anything or were capable of anything.

But you’re not, because you’re an idiot who knows almost exactly nothing relative to all the things that can be known. Just accept it. That’s the path to learning.

The humble founders, with time, find their way through. Your metaphorical hands and fingers may be really fucking bloody from scratching and clawing your way to the other side of this one.

But if you keep trying, you’ll pull it off. In the end, you may wind up selling a completely different product. Or maybe partially different. Lots to learn.

5. Have a Model that Works in Theory

Yay, you sold something. How many of those things do you have to sell to pay your own salary?

1,000 of them? How is that supposed to happen?

Ah right, now we need a model where we can sell enough of the things at enough of the price to pay yourself in a way that’s actually practical.

This is where you figure out whether you attempt “self-service” signup and payment or do 1:1 demos.

6. Achieve Model (or Some Mutant Bastardization of It)

You achieved the model if you can actually or theoretically pay yourself to work on the damned thing full-time.

This is where being young is helpful because you probably don’t have any standards of living. Living in squalor and eating garbage is what you were already doing anyway.

If you are, financially speaking, a fat pig who took some time away from your career to scratch an itch, this is going to be harder to pull off because you have to make more money faster and you’ll have to keep telling yourself you could get a job any time you wanted for the same pay.

And of course, there’s everything in between. I had gotten a taste of working as an SWE at a publicly traded company and had a wife and house at this stage, so it took longer — 4 years. Lots of side gigs and living on my wife’s teacher salary.

7. Hire Someone

You can’t do it all alone. Even if you can practically perform all of the duties, you’re handcuffed to the back of a truck now. You need to be able to take a breather.

Start by hiring someone who can do the stuff you suck at or at least do the things that distract you from talking to customers 1:1 and learning. Eg, an assistant to take care of low-level but time-consuming tasks.

Over time, one-by-one, hire people who specialize in the jobs that distract you from evangelizing, recruiting, making money, and crafting the vision. Think: development, customer support, sales — eventually marketing.

PS: Just because you hate planning and spreadsheets doesn’t mean everyone does. In fact, there are people who actually love those things and they’re exactly who you need.

8. Hire More Than 10 or More People

Can you routinely hire without fucking up?

Have you moved beyond hiring people just to fill spots, or because they were simply available, said the right things, or they came on a recommendation?

Have you learned to hire good and passionate people who fit in with each other and want to learn and be the best?

Goals, quarterly planning, weekly planning, monthly checking. Can you effectively sit at the front of the boat and tell everyone to row at the same time while keeping things moving in the right direction?

9. Remember What the Fuck it Was You Were Supposed to be Doing in the First Place

If you made it this far, congratulations. You may it out of survival mode. You spent so much time figuring out how to survive and grow that you might have forgotten about your hope and dreams and the Huge Fucking Vision you had to begin with. You might have checked your own expectations.

Hell, at some point, you may have fantasized about having a normal 9–5 and being a good and happy employee which, prior to starting this thing, you could never imagine.

Like Sinatra says, “I thought of quittin’ baby, but my heart wouldn’t buy it.”

Bring it all back. Dream big. Flex.

10. Stand for Something

Sometimes we go through the motions and figure out why we’re doing it later. It’s like childhood — it’s only when we’re adults that we start to get a grip on why it was all necessary and who we are.

So now that we’re here — make a positive impact. Treat other people, especially those on their way up, the way you would like to be treated.

And have a lot fucking fun on your ride. Because that’s why you did it all in the first place.

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The challenges never stop coming, so the good news is that you never stop learning.

I have made every mistake imaginable through every single one of these stages. I’ve seen really smart people give up. I’ve seen the allure of careers and money take out otherwise passionate people.

If you want it, you can have it. Fuck anyone who says you can’t, including all the “survivor bias” assholes. The only thing that can kill a business is you: whether you give up, or you took on a time-bomb like debt or VC money.

Go fucking get it. Let the naysayers kill their own dreams, not yours.

Stay young, stay cool, and stay hungry.

Kenny Fucking Katzgrau

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Kenny Fucking Katzgrau is the CEO of Broadstreet, Publisher of RedBankGreen.com, and like every entrepreneur, a prolific maker of mistakes.

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