I am finally in a position where I am truly happy with my professional life. That doesn’t mean that everything is perfect or that I’m even remotely satisfied — far from it. Shit is more complicated and difficult now than ever, but I love it. I love what we are building, I’m incredibly fortunate to work with super smart people, and I walk into work every day fired up and ready for world domination. This makes me truly happy. I had no grand plan to be building MVPs at the NYC Dev Shop. It certainly wasn’t a direct path, but it’s been a fun ride so far. So here is my unabridged 4 Part answer to how it all came to be:

Career Path 4.0 Learn. Improve. Adapt. image

Ignoring my mother’s advice, I quit my cushy job and entered the world of entrepreneurship. By some strange fate that makes me laugh now, I did what I would encourage every aspiring entrepreneur to do. I took a position as a Financial Advisor at a company to remain nameless who put me through an intense sales training program. After 6 months I was fired for the first time in my life. And it was awesome!

First Failure: Become a Financial Advisor

I joined the-company-which-shall-not-be-named as a new advisor. For the first 6 weeks, they taught me to sell. Cold calling, door knocking, corny video recorded sales pitches, the full package. I went into full sponge mode and learned like it was my job.

Armed with this new sales knowledge, I set forth to improve people’s financial lives. I shattered my numbers for assets under management, but I wasn’t selling the product that this company wanted me to push. I was selling what I considered to be best for my clients. The company didn’t like that. We battled over it. They fired me. I had never been fired before from anything in my life, but I felt righteous.

I stood my ground and did what I thought was right for my clients even though it cost me my job.

Tough one to explain to my mom who now sees her unemployed son and starts to think that her homeless fears are coming true.

Second Failure: Start my own Wealth Management Firm

Not all at surprising, all of my clients really appreciated that I sacrificed my own employment for their financial well-being. So when I decided to start my own Wealth Management Firm — Petersen Wealth Management — almost all of my clients came with me (I keep this website up because it makes me giggle).

My thought process at the time: I can just start my own company and I won’t have anyone tell me to do things that are not right for my clients.

In the most idealistic world, this makes total sense. In the real world, this was quite a stupid move…

  • I had no idea how to start or run a business.
  • I learned how to not be a bad financial advisor. I never learned how to be a good one.
  • I had no mentor, advisor or anyone that I could really turn to for advice.
  • I was trying to convince people to trust me to manage their life savings meanwhile I was a 20-something dude spending all of his money trying to start this business.
  • Most Importantly: my heart wasn’t in it

Less than a year into starting my own company, I already didn’t like going to work. I don’t have an MBA, but I’m pretty sure that’s not how it’s supposed to work.

Third Failure: Do a startup

Somewhere along the lines of my masterful networking at PWM, I stumbled upon the NJ Tech Meetup and I saw Shelby.tv (fresh out of TechStars) demo the earliest version of their product. I immediately thought that I could “do a startup” too. Dumb. There is no such thing as “do a startup” or “try a startup.” And this is the though process of someone who wants to “do startup”…

I want to be a founder. I have plenty of ideas. So instead of trying to grow the wealth management business, I’ll read tech blogs, watch TechCrunch Disrupt videos, read everyone’s funding announcements and wonder how long before I raised my first round.

I was hooked.

The best part about this was that I was learning everything I could about the world of tech startups. The worst part about this is what follows…

I started pitching this terrible idea I had for a startup. Finally I found a developer foolish enough to entertain my crazy. We applied to TechStars after about one week of work, and this is the result (I am terribly embarrassed by this, but sometimes you just have to laugh at yourself).

— from May 22, 2011

Clearly, we didn’t get accepted.

Getting rejected by TechStars was an incredibly humbling and educational experience for me. I knew I had a lot of work to do. I knew this wasn’t going to be easy. And I knew that I wanted this more than ever.

On the bright side, I met Alec. We went on to build NY Tech Day and help build DigitalOcean, went through TechStars Boulder, and we founded and continue to build NYC Dev Shop.

I have no f’ing clue what Career Path 5.0 is going to look like or when it is going to come, but I’m super excited and fortunate to be where I’m at today. My incredibly indirect path has given me tremendous experience, and I am so thankful for all the good and bad that comes with it. I continue to use everything I have learned along the way to help shape the future of the Dev Shop and everything we build.