The Truth About What A Startup CEO Does All Day

I was having lunch with a friend yesterday who is attending Colombia Business School. He’s in his second year and was telling me about a class he took on how to build a startup, I loved how they set this up. The class was only two weeks long but went from 9AM to 2PM each day. The second week the class had to form teams, and go through their own lean startup exercise in 5 days. After coming up with a thesis, they were required to go out and talk to 10 relevant people every day in that industry, be it potential customers of their product, VCs, whoever, and they would come back the next day, discuss, and get their ideas ripped apart so that they could make them better.

As I understand it the focus was on two specific things. Validated learning through feedback loops, basically the same thing we do at a real startup except they weren’t actually building the product, and forcing the students to put themselves out there to make those connections, to talk to people, to learn how to ask for feedback and favors and be out there. The latter is probably the most important skill you can learn to prepare you for starting a company.

A lot of people don’t know this, but the job of a startup CEO at the early stage is primarily to ask for favors, knock down doors, get introductions, get free shit, get people to help you, get people to listen to you, get as much feedback as possible, process that feedback, and pretend that you know what the hell you’re talking about at the next meeting so that you can eventually get to the bottom of what it is your users, community members, clients, etc. want. It is a ruthless experience which destroys your pride, if you approach it that way. It wears down your emotional capital and tests your ability to wake up every day and move forward, even when you’re not sure what moving forward looks like. You need to believe in yourself more than anyone else, because if you don’t believe what you’re saying then the person across the table sure as hell won’t, and they can tell in an instant if that’s not the case.

This is what it’s really like to build an innovative startup. It is a soul crushing exercise of eating glass accompanied by moments of pure exhilaration when you’ve done something really fucking cool, and you know it. Those moments are totally worth it, you have to celebrate them and know how to capture the next one. Feeling lost is the worst emotion you can have, and when that happens you need to force yourself to go and talk with more people, get different views, get bombarded by new ideas.

My largest struggle to get my job done throughout the past 16 months has not been a lack of conviction, feeling lost, the inability to sell myself or my ideas, or convince people they should work with me, it has been the feeling at the end of the week that I am just tapped out of emotional capital. Asking for things drains everything you have, it’s really hard on your self esteem. No one wants to feel like they are constantly taking from people and not giving back. Social finance works because giving feels good, it fills up that tank in you, it builds your social capital, your emotional capital, giving feels good, helping feels good.

I spent several years just giving without taking anything. These days I take much more than I give, and that’s been really tough on me. It’s a struggle every monday to get into the mindset of draining that tank until I’m running on fumes, knowing how hard and how far to push. I’m not a naturally outgoing person. That’s my struggle every day, that’s the hardest part of my job.

An advisor of mine, Matt Wallaert, gave me some great advice a few weeks ago. He said that the way to replenish that emotional capital was to spend an hour every Friday and focus on just giving back to people who have helped me out. Set a very defined time to feel like you’ve accomplished something by helping other people, be it making introductions, or buying someone a simple gift, or even just staying in touch with them. The point is that at the end of the week you feel like you’ve given back.

And it definitely works. It feels really good to spend that hour just focusing on how I can help other people. It really can be as simple as looking through LinkedIn and endorsing people who have done a great job helping you out.

The real job of a startup CEO, my real job at Estimize, is to ask for things and learn from others all day. You have to be able to wake up every day and have the right mindset to do that, or your team will build a product no one wants to use or pay for.

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