How to help your entrepreneur


Or, entrepreneurs should quit whining.

Do you have an entrepreneur in your life? Maybe your boss? Your brother? Your wife? Your son? Maybe you’re a VC and you work with a number of different entrepreneurs and founding teams.

They are a different breed, huh? Stubborn, ambitious, maybe very loyal, probably a bit ruthless. You have to be, if you’re going to succeed, that is. Just like snowflakes, all people are different. Of course. And just like all people, if you want a good relationship, you need to understand the person.

There’s a bunch of articles online that I’ve been sharing on social networks lately talking about the challenges of being an entrepreneur. There were reasons why I never wanted to be a CEO. This one is case in point. It’s called Being an Entrepreneur Sucks.

Really? Sure it’s hard. No one said it would be easy.

Yes, the people who think they know better can be obnoxious.

Yes, the mental math around whether or not going to a friend’s on the weekend or go for a hike when your laptop beckons is different than it used to be.

This part was right on the money for me:

There will be your existing friends who won’t understand why their emails take two days to be answered. Out of the 200 notifications that you receive on your iPhone or Galaxy, your brain begins to only register about half of those. So yes, messages fall through the cracks. That weekly party at the neighborhood bar / pub that everyone goes to? It isn’t worth it. It equates to about 7 hours of lost time when it is all said and done. You can’t explain this enough. They will not understand.

But most importantly, there is you. Often misunderstood, tired, depressed, psychologically-altered by stress, volatile, and so damn sure of yourself that no one can convince you that Startup X won’t work. Because of this, few can relate to you anymore. And you can only relate to a few. All you care about is growing something, all the while — making sure that everything else stays in place. And yes, it is harder than most folks would think.

The advice was also correct, starting with: “Remove all negative people from your life.” Would that it were that easy! But point taken.

At the end of the day, though, this is a choice. My strategy is a choice, my work ethic is a choice, my sport is a choice, my job is a choice.

Stopping for petrol at 6am on your way to the airport sucks, though

Stopping for petrol at 6am on your way to the airport sucks, though

I once coined the phrase at CrossFit: “I’m not whining, I’m just making conversation.” I think these blog posts may be quite similar.

Yes, it’s true that our lives are hard. But we make them hard!

Yes, the grind gets to you after a while, and yes the travel is as mentally exhausting as it is physically, and yes it sucks that you would sometimes rather sleep than see your friends, and yes it’s hard always to be there AND IN A GOOD MOOD whenever your customers, or staff, or shareholders have a question for you or just want to talk when you really want to get back to your to-do list.

And then there is this post, the part which really resonated with me was the bit in the middle about having to do what you have to do, despite massive uncertainty.

Yes, it’s true that you can’t share your insecurities with … well, just about anyone. Yes it kind of sucks when all of a sudden one of the giants of the industry wakes up and decides that it’s going to apply the force of its will to competing with you.

This section here:

Being an entrepreneur is about finding your inner self confidence.

  • To be constantly told “it won’t work” but to keep plugging away anyways.
  • To be kicked a lot and still keep standing.
  • To hide your demons so that you don’t scare the bejesus out of your employees.
  • To inspire others to join your cause when by all rational accounts they should not.
  • And having the cojones to have them join you anyways. Pottery Barn rule. You hire them, you own them now. As in your responsible for these lines on their future resume. Don’t fuck them up.
  • To swallow your stresses and insecurities and keep your optimistic game face on in the office. And on your home front. Maybe even try to believe it in your own head.
  • It’s about wanting the right speaking slot at an important conference and hounding the organizer until he lets you do it.
  • It’s telling your creditors that you need 60 extra days to pay. Please. Yes, most entrepreneurs will be nodding their heads right now. Not fun, hey? But that’s what it takes.
  • Firing? Hell, get used to it. It’s a necessity. You better be good at it. Develop a thick skin for it. Not put off the difficult fires. You don’t have the spare budget to suffer fools. Hire fast, fire faster.
  • Friday night in the office while others are at the bar. Sundays in the back of a plane. Center seat. Smelly dude next to you.
  • Investor emails. They are forwarding you set another mother fucking link to an article about your competitors. And wondering why the hell are we not doing THIS like they are. Enough already!?! I told you not to worry about their move into Latin America. I promise you that won’t be a bit market for us. What? No, I’m not worried that they’re higher in the App Store charts than us. They’re paying for traffic. Paying I say! They can’t have a positive LTV on these downloads. You want me to throw around my money like that too, bro?

Some are laughably familiar. Some not. And, lucky me, I’m not even making a new company but taking an existing company to the next level. But still.

Yes, other people can’t actually understand us. But do we care? It’s like Ellie the CrossFitter who wakes up at 5:30am to train. Do most people understand this? Heck no. Does this lack of understanding bother me at all? Nope.

What does bother me? When people whose body fat is three times mine try to tell me how I should be eating.

In my role as Ellie the CrossFit athlete, I have a coach who does my programming, a number of other coaches who help me with technique (could use more of these, actually!), and two people, soon to be three, who help keep my body healthy. And then there is the mental training.

In my role now as Skyrove CEO I have a business coach, a guy who is pretty much my own personal telecoms mentor, and a whole array of people with expertise who I go to for advice. If I have a sales question, I ask an enterprise sales guy. If I want to know how a mobile carrier thinks, I ask people who work there. If I want to know what does and doesn’t work in terms of business and operational models, or what software vendors to look at, and which are a waste of time, I ask trusted counterparts from overseas.

The problem of course, is that you don’t know what you don’t know. I learned areas of the business in a particular order. In retrospect I should have taken a slightly different order but its water under the bridge now. I have an excellent staff who I [mostly] trust and who [mostly] trust me.

What am I trying to say? It’s the nature of the beast that your entrepreneur is going to feel stressed, tired, emotionally drained, misunderstood, and quite probably cranky with you because you are getting in the way of him or her getting sh*t done.

If you want a smooth relationship, understand where your entrepreneur is coming from. Think for a minute about what might be exciting them and scaring them. But also, read their emotions as best you can.

When I am with some friends who aren’t from telecoms or enterprise software I just want to talk about other things. If you don’t understand what an API is or what OTT means, the likelihood that I can tell you what I did at work in the last week and have you understand it is pretty low. But that’s fine. I don’t need to understand the details of the shaping pools or interference scans that my technical team put together. Any more than if your job is mechanical engineering or product management for FMCG or Spanish literature, I’m not going to be able to understand what you do at work all day, either.

We don’t need to understand the details to appreciate the humanity of struggles with customers, co-workers, family members or friends who ‘don’t get it,’ etc., etc.

Well, you do sometimes get to go cool places.

Well, you do sometimes get to go cool places.

Bottom line? If you can grok the details, offer specific feedback.

If you cannot understand the details but you can follow the line of thinking, critique the path.

If you cannot do either, or the entrepreneur isn’t a close friend or family member and doesn’t really feel like talking about the details, then provide emotional support. I’ve said it many times before but the difference between success and failure on a max lift, or anything that strains your capabilities, is faith in yourself. Now presuming that you’re on a good path and not a dumb one, what you need is trust, and faith, and people telling you that you’re going to succeed and they are there to help you.

And we’re not stupid. Just like athletes, we can tell the difference between real support, fake support (people who don’t really care), and what may as well be sabotage, intentional or not. I see this ALL THE TIME in my gym, and if you think it doesn’t happen in the business world too, you’re kidding yourself.

We read body language, and tone, and for me at least, I’m like an elephant. I appreciate constructive criticism. Not critical criticism with no solutions. The righteous indignation that comes with an unfair attack can be fun in its own way, but I devote far too much emotional energy to becoming angry at partners or service providers or stakeholders or customers who are unfairly attacking one of us.

That’s life. But what goes around comes around. You should never talk smack about your co-workers around the water cooler. Never diss your suppliers unless they’ve really earned it. Never ever say anything to any one of them that you haven’t first said to their face. Because gossip and backstabbing normally comes out. The truth always does, hey.

If your entrepreneur is on a dumb path OR is making an obvious tactical error on a good path, it is your duty to tell them. But you can’t walk the path for them or with them, nor are you really probably qualified to know if it’s the right path. That’s the problem. If you think it’s wrong, say so, but understand that your entrepreneur is going to do whatever they want regardless of what you say.

That’s how we roll.

When we’re not busy shaking trees or rocking boats or succeeding at one thing while we fail at another.

It always comes down to this: either help, detach yourself from the situation, or stay the hell out of the way.

If you love your entrepreneur, help is appreciated. Despite what we may say, we do appreciate help.

But make sure you’re helping, not just stressing us out. As coach says: “Relax. Tense muscles are slow muscles.”

Haste makes waste, and stress makes haste.


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