Column: My Struggles, as an Entrepreneur.

Emotionally gruelling. Depressing. Terrified of what’s to come. That’s how I would describe running a failing company. It’s one of the worst professional experiences someone can have. They talk about entrepreneurship being like a roller coaster. Well, failing would definitely the lowest part. Stuck at the start, body lock still open, frustrated with the time it’s taking to get rolling up the ramp. Yet, failure is surprisingly common and ultimately a rewarding experience - The Anonymous

If I had the power I would actually love to ‘station’ any aspiring entrepreneur at a failing start-up and have them live through bankruptcy. Then again, once you have seen that potential disaster zone and realize how much can go wrong, you might decide never to start a company. After all, entrepreneurship often happens because people underestimate how difficult something will be and how long it will take, and then get it done anyway. It’s true, you can learn a lot from mistakes. But, wouldn’t it be great if you could stick to learning from success. So I would advise you to learn from your own success and from other people’s mistakes.

My biggest lesson? Team dynamics is probably the most important factor in a start-up. Not the idea. Not the execution plan or business plan. Not how good your team is in paper. Let me spell that out once more: How well your team works together will greatly define how well your start-up does. And that’s not just my experience. A 10-year long Harvard report on start-ups found the same, team dynamics is the key stone in building a company. Let me tell you a story, so perhaps, you can learn from my mistakes.

What you shouldn’t do

Years ago, I got into my first start-up. On paper, things seemed amazing. It was a bit like the way super-groups were formed in music: you get the best guitarist here, the coolest singer there, and a kick-ass drummer. But what if it turns out they suck at playing together? This is what happened to us. This begs the question: why do people with amazing skills fail to perform together? Usually it has to do with a mismatch of personalities and motivations.

Personality Disorderliness

The first problem we failed to discover was that we had too much of the same personalities. On the MBTI-scale, we were primarily in the thinking, visioning quadrant: abstract people. Planners. But very few doers. So we spent hours talking, everyone wrestling for their share of the time, battling to get logical supremacy. All co-founders had a desire for dominance, which made everyone the king of their own little kingdom — doing their own, autonomous thing, sometimes even without informing others. This created a lot of tension, and it became a turf war. “No, my marketing campaign is more important than your sales leaflet!” I know, it sounds silly now, but it’s much harder to spot while living in the pre-honeymoon period full of presumptions about your co-founders and without knowledge about how personalities function together.

Misaligned Motivations

This one is the most difficult to discover. Why do people do the things they do? There are a number of core motivations that always pop-up in research on what drives entrepreneurs. There’s always some overlap, but what individual co-founders value most will really shape how one prioritizes. The funny thing is, many people are blind to their motivations and inclinations, so they will see it as the logical thing to do, not even seeing what 20 other options they’re not considering which might be at the core of their logical action. The subconscious isn’t easily reflected upon.

In our case, we had someone who pretty much saw himself as the end and company as means to promote himself. This was poison for our company. Here’s why: What this guy was doing, was getting himself in the spotlights and getting praise for other people’s work while telling overblown stories. As a consequence you get prioritization problems: when he had to decide between making a new product happen or doing a photo shoot and interview with a tech blog, guess what got the priority?

Cool story bro. But what ‘should’ I do instead?

Good one. Let’s get into that. After all, there are many ways to lose money in a casino, and only a few to predictably win. The same goes for starting companies. So, how does one shift the odds in your favour?

Look For Personality Synergy

First, know thyself. I’m a big-picture thinker, abstract and mildly introverted. My weakness is over-analysis and lack of real-world testing. You should learn about yourself: do an MBTI test, think about how you like to work, ask friends and co-workers to describe your personality strengths and flaws. Be open to criticism. This will be uncomfortable, but it’s the path to growth.

Secondly, find people who fill in for your flaws and amplify your strengths, and do the same for them. Let’s say you’re an introverted tech guy who’s a great inventor, but sucks at deal-making and sales. Find an extraverted, enthusiastic person who’s great at the commercial part! This week, I worked in wonderful sync with two people with distinct personalities. The first one, is a super-organized mastermind who ‘closes’ all the open loops that I miss. His methodical, detailed approach complements my big-picture hopping. He likes working with me because I can conceptualize new things ridiculously fast (and moderately good, as I like to believe) as he can’t really do that part. The other is on the opposite end of the chaotic scale: a super-creative, smart kid that is like a fire-hose of ideas. We click because I can structure his waterfall of ideas and help choose what fits in whatever context we’re exploring.

Align Motivations

Again, the first step is to understand your own motivations. Inc magazine’s “What drives entrepreneurs?”* is a great place to start. Be honest with yourself, if you want a comfortable lifestyle and to be able to go surfing on Wednesdays if you feel like it, that’s fine. Just don’t become a part of a team where everyone else believes you should work until the early hours, every day of the week.

How do you know motivations beforehand? First, it helps to discuss them openly, but not before everyone has spent time soul-searching and has written their motivation down. Be aware of the all too common socially acceptable answers: many will say they want to work hard and grow the company. But how do you define working hard? What’s the most important? You can judge the motivations of the people you’ve worked with before, but what do you do when you’re co-founding with people you have never worked with before?

The dynamic flexible start-up

Fortunately the process of discovering how you fit in a team is not the task of a hermit. In fact self discovery through doing something together can be one of the most rewarding parts of doing a start up. So how does one create an environment in a company that serves the purpose of creating the best team for a great start-up experience.

Make Dynamic Agreements

What if it turns out that the person who said ‘I don’t mind risk and am in it for the intellectual challenge’, finds out that reducing risk and getting recognition are their key motivators? Is the team able to agree and pivot motivations. Does the Dutch national football team just pick 11 of the best players and go off to the World Cup. Do the special forces go to war before considering elaborate training and simulations? So much can happen during a start-up, and you’ll only know how well you perform together once you’ve been at it for a while. With so much dynamism going on, is it smart to make static agreements on everything from roles, to equity, to who’s on the team?

Here’s a better way to do it: First, acknowledge the dynamics and set a milestone around 2-3 months into the start-up journey, where you’ll review the value of everyone’s contribution, see how well personalities fit together and whether everyone is in the right position. Maybe some people will have to leave, and you will need to find a replacement. Or you’ll decide you need a different kind of co-founder to join in. This can be confronting, but do realize that when someone isn’t performing in a start-up team, especially if they are a highly skilled person, they are frustrated too. Do you really think it’s a good idea to put them in the same position for the next few years? It will probably be hell for them and you. This kind of dynamic agreement can be liberating for everyone by giving the start-up room to adapt.

Start Softly

An even better way to approach this, is to do a ‘soft start’, where you work on a project together for a few months. Heck, it could even be a well-paid project for a client. I know of a group who decided to embark on an entrepreneurial journey, but one of the crucial people on the team was severely in debt. This means his lifestyle, paying off debts while making a living and worrying about debts, wasn’t compatible with a start-up. They decided to work for 6 months to clear away his debts.

Doing this project was the perfect test to see if the team could work together on a common goal. And it truly transformed them. The now out-of-debt person is incredibly grateful. The others bonded with him and each other over this mission. When I see them working together now, it feels like a family. Not everything was a fairy-tale, mind you. One person left after a few months, mostly because he realized he was kind of obsolete: there was too much overlap with the skills of some other team members. But it’s much better to find out at that point, where everything is adaptable, then after they’d started an entrepreneurial company together.

Team dynamics are going to be crucial in your start-up. More than the idea, business plan or the actual skills of your team. So make sure you assemble people that have complementary personalities and similar motivations. And make sure you train first and play a couple of friendly matches, adjust the team, then fly off to the World Cup.

Some say he has private conversations with Steve Jobs in his dreams. And a CAT scan showed his brain has evolved into the segments of a business model canvas. All we really know is this column was written by ‘The Anonymous’.