The Hells of Being a Founder

Being a founder is horrible. There, I said it. We are supposed to be visionaries and rebels, while being pragmatic and concrete, while being good leaders. Those features don’t fit one body, who isn’t about to explode. I have founded two companies and both times I have been in agony and pain. Why?

The path from ambitious idea to product and eventually market is more art than science. And, we don’t doubt that artists are mad. Often chasing product market fit feels like when you are trying to explain a dream. It felt so clear, so vivid, so tangible.

The frustration of being asked how it works, how to monetize, where it leads, who it’s for — can make you actually go mad. But still, we all require it of founders. We the co-founders, we the employees, we the investors. Even stranger; we, the founders, willingly put ourselves in this situation. Some of us repeatedly.

When you are finally able to explain your dream, you find yourself being too early for the market or in the rat race of getting biggest first. Either are painful in their respective ways. Like a genius kid going to college, you will either be ignored or laughed at or will have to grow up fast.

This said, being a founder can be the trip of a lifetime, so how do we grow up quickly and ease the inevitable blows?

1. Don’t fool yourself

Set your ambition. Do you want to build a huge scalable startup or run a lifestyle business? Both are fine. Life is a single player game.

Run a dashboard, not a leaderboard. Don’t care if everyone is hyping one thing. Do your thing.

You and your team should set a vision that gives you energy. A vision is essentially your purpose. And a purpose is the explanation to why you do it.

Purpose: why it is worth it, even when it is hard and horrible.

A vision doesn’t appear overnight and is always a work in progress. The vision could be anything from changing banking to building the best place to work. But people who stop subscribing to it should leave. Communicate it and be honest what you want to achieve.

The best way to be unhappy is having one ambition but living another.

2. Do one thing well

Startups don’t die of lack of funding. They drown. Drown in tasks and doing the wrong things. Most founders are in panic, but they don’t have enough focus and a sense of urgency. Decide what your goals and hypotheses are and work only in that direction until proven wrong. Focus. Do the things you do well, and accept that others won’t be done.

Don’t care about the office, the design, the logo, the name, or the competition. Care about the people whose problem you are solving and only them.

Ask people why they think you will fail. Potential investors. Your employees. Peers. Your siblings. Anyone. Write down the answers. Don’t get angry. Use these fears, uncertainties, and doubts as fuel. These are things you have to (im)prove. If people don’t think the product can be monetized, show it. Run experiments. They are right until they believe in you.

3. The team is the product

Being a founder is not only potentially lonely, but you need to morph and transform from a craftsperson to a leader. One hour you are coding, designing, writing. The next people in the team expect you to have zoomed out, care about them, and have a plan and process for everything. Don’t try to be an inventor genius and jack-of-all-trades. Rely on others. Trust others do their part.

Build a team and co-founders who split the burden. Make sure people are negative in a constructive way. If someone can’t see the dream you are trying to convey, ask them for input. Some people are best under pressure. Some are best when they are allowed to dream. The common denominator is that we all need to be heard to perform.

The vision is bigger than the ego.

If someone doesn’t believe in the plan, ask them three things that they need to see to believe. Unfortunately, it’s easier and sometimes cooler to be a skeptic than a believer, but the two need each other.

Run regular meetings giving everyone space and opportunity to tell you how they are feeling. Personally and about work. Talk about what could kill the company. Don’t brush it off, bring light to the dark corners.

Don’t hide from the dark, that is how you make it scary.

Being open will make the skeptics feel you are reasonable and enable their superpower in the right way. You as a founder and CEO should do this one-on-one, but also make sure that you are allowing people to talk openly about it with each other.

4. Investors are not bosses

Your investors are clueless too. They didn’t know what they were doing, and they sure don’t know what you are trying to do. Their questions are not because they don’t believe in you, but because they want to help you. And I know that makes them sound like your parents when you were a teen.

There are only three ways to handle problems: solve them, accept them, or avoid them.

Be transparent and make your investors your part-time colleagues. Expect them to help out and make sure they can. Just keep informing them. If your investors don’t want to help, then let go.

Realize that you never, ever will be satisfied. You will be your worst critic. Learn to feel pride.

5. The four ways to fail

What most of us consider failing is not dangerous. Not getting traction, losing investors’ money, or needing to kill your darlings, is part of the journey. Remember your knees when you learned how to bike. When did we lose that and expected learning to look like a straight line without bumps and crashes?

You, as a person, can only fail in four ways:

• Economic Fail: ending up in personal debt and personal bankruptcy.
• Health Fail: Mentally, physically, or relationally being broke.
• Bitterness Fail: Lying to yourself. Trying too little and becoming bitter. Becoming a zombie startup.
• Becoming an asshole. You know what I mean.

The company can fail to get traction, but that is another matter. Don’t mix these up. Remember that you are one person, and the company another entity. You are not a failure if the company tanks. Building a startup is hard enough — you don’t need to make it a life or death experience.

But yes — you should grit and fight. There will be crying. There will be sleepness nights. But, try being a nice, healthy person with 8 hours of unmedicated sleep. Actually, scratch “unmedicated.” And 8.

6. Dare greatly

Creating something new is hard. Don’t criticize those who try, even if it makes you sound cool. Your candle doesn’t shine brighter because you try to fart out others. And chances are they have heard the smart thing you just thought about several times before, and you are not adding value.

Print, frame, and put on the wall:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

— Theodore Roosevelt

I recently talked about the horrors of being a founder. If you want to see me talk about it on stage, then enjoy: