Day 74: Ask To Apprentice An Entrepreneur

For day 74 of #100DaysOfDiscomfort I asked if I could apprentice an entrepreneur.

For the past 311 days, I’ve been documenting my journey of #365DaysOfCode on my github. Here’s today’s log entry.

My job hunt for a developer position started on day 300.

Everyone Says It Wont Happen

When I articulate my dream job, I get scoffs. What is my dream job? A developer position where I can learn about tech from the senior devs and entrepreneurship from the CEO.

People say this isn’t possible. Nobody’s going to take on a newbie developer and teach them entrepreneurship. If they do, the little newbie entrepreneur will leave and start their own business. Thus, waisting the companies precious time!

Some people recommended I withhold any mention of becoming an entrepreneur. Otherwise, the company will be afraid to hire me.

Outliers Shouldn’t Take Advice From The Average

In my experience, normal people give poor advice to outliers.

My goals make me an outlier. I want to be a tech entrepreneur one day. Others don’t. Therefore, I shouldn’t take the normal safe path that most take.

Mentorship is invaluable. Consequently, I will do what I have to do in order to learn what I need to learn.

If I get the perfect tailored job, the experience will be an investment in myself. Or I can take the safe path of getting a regular developer job. This would pay well. But it’s a lesser investment in myself.

You miss 100% of the shots you don’t take. I figured, why not reach out to a CEO I admire and ask for what I want? Additionally, I’ll make it invaluable to them by offering to do it for low/no pay as an apprentice.

Currently, I’m residing in my parents basement with no rent, so why not take advantage of my unique situation?

Reaching Out

I reached out to the CEO of a startup in Chicago that I’m really interested in on LinkedIn.

Hi Cory, we met at Shaily’s event a few weeks ago. I was the one who taught myself software development and we spoke briefly. I listened to some podcast interviews with you and I was really interested in what you’re doing with Shedwool, AI, and mentoring entrepreneurs. I find your particular brand of entrepreneurship inspiring: Entrepreneurs who want to help and give, while making something great. I’m curious if there’s anyway I might fit in with Shedwool. I’m looking to learn and grow as a developer.  Additionally, I’d love to learn about entrepreneurship. Is there anyway I could help Shedwool while learning from you and your team, maybe an apprenticeship?


I had no idea what to expect. But Cory wrote back only hours later:

Absolutely! I’d love that

-Cory the entrepreneur

I’ll be meeting tomorrow with Cory to see what we can figure out.

Asking Vs. Answering

Most of the time, when we look for opportunities, we look for others who are asking. Then we answer them. Instead, I’m asking for exactly what I want and waiting for others to answer.

In the former situation, we’re hunting opportunities. In the latter, we’re creating them.

Asking gives me a sense of confidence. If I go out and answer job openings, I feel at the the mercy of the company. On the other hand, when I ask for what I want, I feel powerful. I feel in control. My anxiety is gone.

Of course, I’m still factoring in the other person’s wants. Then, I can frame what I want in a way that helps both of us.

About Dashiell: My name is Dashiell Bark-Huss, sometimes people call me Dash. I’m a self taught software developer with an interest in lucid dreaming, self quantification, health, stoicism, and pranks.

Leave a Reply

Your email address will not be published. Required fields are marked *