Jevon MacDonald

co-founder of Startupnorth.ca

The things an entrepreneur will never tell you

We always glorify the struggle of the entrepreneur. Late nights, poor diet and little contact with friends. It’s cliche because it is real but we gloss over just how big of a toll it really takes.

Last week I was having a drink with a recently exited entrepreneur. His last exit was a biggie at $700m+. It seemed to be amazingly well executed from the outside but as we dug in to his story over a few hours I was amazed at how much I could relate to all the ups and downs and how tenuous his hold on success was the entire time.

Here are my top things that a young (first to fifth time) entrepreneur never tells you when they are in the thick of it, and they are the things you will never understand until you are there. Not everyone deals with each of these things, but the more I talk about it openly the more strongly I feel that it is the norm, not the exception.

The focus is debilitating

“He/She is focused!”, “Man, they are hustling!” — you see an someone in action, executing rapidly and firing on all cylinders. You feel like you go to sleep and when you wake up the entrepreneur has already taken it to the next level. How do they do it?

When you start operating and you can feel the business working you get overtaken by a myopic focus that drives you from one thing to the next. You can see everything in the path in front of you: Obstacles, opportunities and a sense of momentum. To maintain such intense focus though you have to take your focus off other things, and everyone has to choose. Health, friends, family, hobbies. Nobody de-prioritizes any of these things but the problem is you don’t realize which decisions you have made until they are well behind you.

Entrepreneurs can end up wracked with guilt and wishing they had done things differently.

The focus is what gives you the highest highs, but drags you in to the lowest lows. Every win seems gigantic and every loss feels equally consequential and that is because of that myopic focus– you only see a few things in front of you and it takes a lot of maturity to be able to focus on the longer term.

The lows are real

No matter how many highs you get, most entrepreneurs feel some incredibly low times. Almost universally we put on a very positive public face and you would rarely know, but the more time you spend with fellow entrepreneurs after they have left their latest startup, they are more open about talking about those dark days.

For some of us it makes it feel impossible to get out of bed, sometimes you just can’t bear another meeting. Some founders get angry and lash out, others just hit the bottle way harder than they want you to know.

These dark periods can last an afternoon or they can last a week. They are only multiplied by the unshakeable focus I talked about above. The focus narrows even more and an obsession with certain metrics or ways out of the trough can develop.

A manic nature develops and you start to seek the next high. You come out of the low with a focus on something that you know will give you the high you need and you drive towards it harder than most normal people would.

You feel alone and you are alone

I think a big reason founders move to San Francisco or the Bay Area is because you can at least find hundreds of thousands of like minded people. You feel just a little less alone while you are single handedly taking on the world.

You learn quickly that you can’t take your problems home because one day you are up and one day you are down, or you might be both on the same day. It doesn’t feel fair to put that on your partner, and if you did they would eventually get tired of it after years of constant ups and downs.

You toughen up and you bottle it up. You are afraid to really talk about things because you can’t afford to open the bottle– it might knock off your focus and set your company back. That’s a no-no.

The best investors in the world know that entrepreneurs have this loneliness and they take time to give you a safe space to vent. Almost nobody else can give you this safe space and it takes a lot of work on both sides to develop a level of trust that allows it.

Failure isn’t an option

Failure is OK. We all know that. It’s a powerful learning tool and it is a required piece of the long term success of an entrepreneur.

Holy shit it is scary though.

You are paying salaries, the people you are paying have families and they rely on you. Your investors backed you for a lot of reasons, but you feel like you have to deliver for them.

Your customers are relying on you.

You WANT to succeed this time, you don’t want to have to go through another cycle looking for a success.

It feels overwhelming and it weighs on you. We try to relax and blow off steam, but the feeling that it’s all on you doesn’t go away.

Nobody tells you it is going to be easy, but I think a few of us are surprised by just how much of a toll building a startup can take. Maybe it is hard because it was just never meant to be easy? Who knows.

Keep at it.

The companies I should have paid more

Building a startup is hard and managing ops is really hard. Devops are hard and expensive.
Luckily these days there are some amazing companies making it way easier to build the startup of your dreams. Frankly, I don’t think they are getting paid nearly enough while some are getting paid way too much.

What apps are a key part of your day-to-day and which could you live without?

GitHub – Paid: $50/month. Should be: $500/month
GitHub is the lifeblood of our dev team. Everything lives in it and it has allowed us to avoid hiring devops for years. You can hack it, glue it and spew it all over the place. All the while it is secure and reliable, almost never letting us down. It has a ton of “good enough” features like Issues and the Wiki and they are “great” because they integrate right in to the most important parts of GitHub.

I want this company to live a long and healthy life. May they never be acquired and may they reign for all time.

HipChat – Paid: $2/person/month. Should be: $150/month all-in
We have a love/hate relationship with HipChat. We wrote our own robot which connects GitHub in to Hipchat and that is useful for managing a big chunk of our dev process. Hipchat also does a great job of maintaining conversation history, so we can find almost anything we need to in those “what was that thing?” moments.

Hipchat does however have a horrible Adobe AIR desktop client and one of the worst mobile clients I have ever seen for chat. HipChat on the iPhone has no sense of message status. It tells you “you have a new message!” but then you have to, literally, hunt every chat room and look for a new message. It is also extremely slow to load. We call this “Hipchat anxiety” when we are out of the office. If they can fix these issues then it would be a huge positive for HipChat users. The reason I should have paid HipChat more is because it is clearly useful but they also clearly need the money in order to improve the product.
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Google Apps – Paid: $50/user/year. Should be: $150/user/year
I cannot overstate how awesome it is to have Email, Calendar and Docs out of the box for every new employee. Rock solid service and the apps are always improving. It saves having to buy a MS Office license for every new hire and it has collaboration/sharing baked in. Google apps I love you and I will never hurt you.

Skype – Paid: nothing. Should be: $30/user/year
Skype has been free for Skype-to-Skype for so long that I think Governments would be ousted if they tried to charge for the basic service, but wow we used a lot of Skype calls in the early days. Skype video chat is still the best, even if Google Hangouts are getting better, and it’s very reliable.

Trello – Paid: I don’t think we do. Should be: Something more than $0

Trello polarizes. Some love it, some hate it. We clearly love it because we use it to prioritize anything and everything. We should be paying something.

Things we paid too much for:

Some apps are just too expensive for startups and really aren’t worth even doing the free trial.

My cellphone. Paid: $60 to $600/month. Should be: $60/month.

A cellphone bill strikes fear in to a startup’s heart. You make a few trips out of the country and you are greeted with a gigantic roaming bill when you get back. You aren’t the bankers and the lawyers that the phone company is targetting with these crazy roaming rates but you still have to run your business and you need to be able to communicate while you are on the road. I wish I could have just paid a consistent amount that would have let me plan for cellphone expenses.

Box.com. Paid $15/user/month (and tricked in to a 1-year contract). Should be: $10/user/month with no contract.
Box does this thing where when you sign up for a paid plan they have you click a box that says “I agree to the terms of service”. When you go and look at that terms of service it commits you to a 1-year contract. It really is absurd. Other contract-based SaaS providers are much more transparent about contracts. Dropbox was a cheap alternative that we used even though we were paying for Box.

Webex/Gotomeeting. Paid: didn’t. Should be: cheap.
Even if you are a co-browsing startup you need screensharing occasionally believe it or not. We avoided using it mostly but when we did need it there were much better and cheaper options than Webex or Goto.

Less boardrooms, more dinner tables.

People have become really good at pitching. The art has turned in to a bit of a science and if you do ever find yourself in front of a room of people it is par for the course for you to “nail it”. The pitch, it seems, is dead media.

It’s time to stop obsessing with your pitch and start building relationships.

If you are going to raise financing for your new product then you need to learn what it means to build relationships.

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We started Founders and Funders on the basis that you would never want to accept investment from someone you couldn’t eat a meal with. What better way to find out than to eat a meal with them? It works incredibly well.

You need to find ways to end up at more dinner tables and in less boardrooms.

Also: Eat with your mouth closed ya filthy animal.

Funny story. When I was raising an angel round for my latest company I met a fairly prominent investor for lunch. I ordered a $15 sandwich combo. He got two doubles of Grey Goose, the Rib Eye, and a glass of wine. Then dessert! The shithead then stuck me with the bill! I kid you not. He then got in his car and drove off, I contemplated calling in the DUI. The hell if I was going to let him invest in my company. It was worth the $120 it took to figure it out.

I tell every entrepreneur that story, and I name names!

Then there was the time I met with Steve Anderson at a crowded bar. You should consider an invitation to meet an investor at a bar or restaurant a golden ticket. Steve came in, he was starving. I was a bit nervous so I didn’t eat much but we shared some appetizers. He was cool as shit and I knew I wanted him in my round before that meeting was over. Having a coffee and being forced to sit in a corner of a busy bar helps you get almost every “is this guy/girl legit? can I talk to him/her without needing to watch myself?” sort of stuff out of the way.

I met another investor at a Yogurt shop (he gave a fake name and told them my name was Mike). Another one in a Tiki bar and another in a co-working space.

Get out of the boardroom. Loosen up. Your pitch sucks but your product is cool, and you are even cooler.