Things I Had to Learn In The Past Year as a Startup Founder (or am still learning)

It’s been about a year since I left StockTwits to build Estimize. I have never been sick more in my life, slept this little, ate this poorly, been in this bad of athletic shape, ignored my friends and family as much, and I’ve never had more fun. Building this company has taken every ounce out of me, and it has been extremely rewarding.

I talk (sometimes preach) about how in this new economic paradigm you will need to learn to live with less income, but that if you utilize the new tools at your disposal, your quality of life will improve. You will also be pushed towards seeing a greater risk/reward to starting your own businesses, both because building things has never been more lucrative and cheap, and because your ability to find employment with someone else is degrading. It’s just the reality of the fact that Instagram was sold to Facebook for one billion dollars, and had 13, yes count them 13 employees.

But, no matter what new paradigm we’re operating under, I caution all of you to think long and hard about what it means to be an entrepreneur. If you really want to go for it, quit your cushy six figure job, you are in for a smack in the face.

I was lucky get an amazing education so to speak at StockTwits before starting Estimize, but nothing prepares you for having to do it on your own, nothing. You can read all the blogs, books, have all the right friends and mentors, but there’s no way to teach some of the lessons that you just have to learn as a first time startup founder. This is why angels and venture capitalists love backing successful entrepreneurs again and again, and even ones who have failed at least once already, because they’ve already been through the fire.

Here are some of the things I’ve had to learn this year, even after being entrepreneurial my whole life, and previously starting my own asset management firm from the ground up.

Your pride is worth nothing, put it down and ask people for favors.

You never get anything from anyone if you don’t ask.

Learn to love the word No, a lot, and just accept it.

Not many people will say the word No to you, understand when someone is saying no without saying no.

Getting a no is not the end of the conversation, it is the start, now go and prove to them they should say yes, keep asking.

Spend your social capital now, it’s not worth anything sitting in your Klout score, number of Twitter followers, or the number of hits your blog gets.

When looking for investment money, it doesn’t matter where your business is at, investors want to see progress not one data point, even if you are extremely early.

Sell things before you actually have them. Sell then build. It will take you forever to get anything done if you wait until everything is perfect.

Nothing should ever be perfect, or you’ve wasted time.

There is no shame in working out of a coffee shop, stop pretending you have an office.

Having an office feels really good when you finally get one after working in a coffee shop for 6 months.

Invite everyone to your new office, it will make you feel good and give you energy.

You have to celebrate wins, after being told no all the time, you have to celebrate when you win.

You will have less sex, just accept it.

Your family and friends will think you’ve fallen off the face of the earth, make sure to send a mass email once every month or two apologizing, then joke about how you promise to take them all on vacation when you’re rich, they will understand.

Don’t sleep at the office, it kills your morale, this is a marathon not a sprint.

Don’t sleep in the locker room at the hockey rink after your 11:30 PM game, get dressed and go home.

If you want to get connected with someone, you must find a trusted contact of theirs to go through. A one line intro from a friend is 1,000,000 better than a cold email or a cold call.

Don’t ask anyone else to set a time with you, always give them several times to choose from, it forces action.

You need to spoon feed journalists stories, you can’t expect them to figure out what you’re doing.

Most journalists don’t care about your business, tell the story of how your business fits into a larger theme.

Incumbents will attempt to discredit you, your business, and your community because they feel threatened, just go run them over, this is a game for big boys.

Pivotal tracker only works as well as you use it.

The only way to recruit at an early stage is through your connections, it’s completely relationship based.

You need to find specific points on which to build momentum, momentum is everything for your product and your company.

Use LinkedIn religiously, go through the contacts of the people you know and ask them for introductions.

Learn what resonates and what doesn’t when telling people the story of your company, A/B test like you would a feature.

 

I’ve made a lot of mistakes this year, as I expected I would. But we’ve had a lot of great wins at Estimize, and the fun part is just beginning. I’m sure I’ll write this post again next year and have just as many new things on that list. This year has been the only time in my life I have ever envied someone who is 40 years old, for the fact that they have been through this several times successfully, and don’t need to learn these hard lessons over again.

I’m enjoying the journey though.

 

 

 

 

Full Disclosure: Nothing on this site should ever be considered to be advice, research or an invitation to buy or sell any securities, please see the Disclaimer page for a full disclaimer.


blog comments powered by Disqus