How Success Forced Me to Stop Doing the Job I Loved

“I’m a product guy.” That’s pretty much how I used to start any “about me” dialogue as a way of setting the stage for what type of CEO I was.

I liked making it clear that I was a CEO who knows product, knows design, knows how to code and still spends a considerable amount of time doing all of those things.

I’ve always been a product guy.

When I was 9, I started a t-shirt business with a friend. Business plan: make one-off shirts with detailed hand-drawn designs. My first (and only) shirt was a Ferrari F40 painted on a white T.

We sold that shirt for $20. In today’s dollars that’s around thirty seven bucks. Not bad.

When I was in my early 20s, I became obsessed with building and tweaking Media Center PCs (or HTPCs -- “Home Theatre Personal Computers”). I built a crazy rig from scratch, followed by another even better one. It then dawned on me that everyone would want one of these. I poured endless hours into logo design, marketing materials, and (some) inventory deals. I distributed flyers to all the wealthy people I knew (these things were expensive to build) and waited for the sales to come in.

I sold one! But installing and servicing it was a nightmare. Time to move on.

After acquiring a computer science degree and settling into the workforce, I started writing software; some of it freelance work. One project involved “automating an email flow” so that prospects would be emailed three times in a certain sequence until they responded. Oh man, were we ever on to something.

The transition to entrepreneur begins.

I got paid to write software, which was cool, but (with permission) I decided to try and market this software as a product. I spent more time writing code that would enable this software -- initially designed for one user -- to be capable of supporting multiple users/companies. I cared just as much about UX/UI as I did about functionality, but most of this software was written in classic ASP with an Microsoft Access database (if you can call it a database). So it wasn’t exactly set it up to scale. It was an MVP (“Minimum Viable Product”).

By the time my MVP was ready for customers, I started making cold calls to businesses that would absolutely need this kind of email automation. Well, actually I made one cold call. I can still remember how flustered I was even though the lady was nice and willing to hear me out! Time to move on…

Related: 6 Stories of Super Successes Who Overcame Failure

This happened with a handful of other software projects that, in retrospect, would have all been viable businesses. Some were entrepreneurial attempts, others were products I built for my family’s business to use internally.

First, there was a resumé site that would allow users to create their professional profile (this was pre-LinkedIn): total fail.

Then, a sophisticated employee/vendor training system that rewarded users with a certificate and prize: internal success.

Next, a shipping-information system that was actually used by some of the biggest brands in the world: another internal hit!

Finally, a movie site dedicated to finding movies based on the cast members you liked: my favorite personal project -- it started going viral so I took it down.

Growing up, I was always a fan of the designing, building, and marketing, but wanted little to do with selling or supporting.

Fast forward a decade.

Today, I am a co-founder and CEO of an amazing, fast growing, SaaS company where my responsibilities have predominantly been product vision and execution. Although in the early days I was doing everything including selling, supporting and operations, my co-founder and COO handles those areas of the business much better than I ever could. And with a team now of over 65 incredible employees, I have the freedom to focus on what I love -- product.

But a CEO who still codes is total taboo. I’m sure it happens more than we know -- the CEO of New Relic is the only well-regarded CEO I’ve heard speak openly about coding -- but it’s definitely not something you go around bragging about. I’m a CEO -- I should be doing “CEO things”!

Related: Lead From the Top: 5 Core Responsibilities of a CEO

I haven’t written a line of code in four months.

It’s been four months since I’ve contributed directly to our product. Before that, my longest stretch was probably four days!

So, what changed?

1. I finally realized that product evolution never ends and is only one facet of the business. Other departments need me too.
2. I brought on a VP of Engineering that I felt I could trust with running the product to my satisfaction. He started just over four months ago.
3. For the product to evolve and meet the vision, the vision itself needed my full attention.

I ventured out.

I started spending a lot of time thinking, speaking, presenting, and formulating a thesis around Uberflip’s business and surrounding landscape.

I started going to every sales meeting to be fully informed about the sales process. I was always interested in it, I just didn’t want to do it myself.

I started checking in with my management team more frequently to learn about, and contribute to, the day-to-day evolution of each department.

I started writing more articles instead of lines of code.

I created a framework for content marketing that not only helped to express my thoughts, but also enabled us as a team to more easily make tough decisions regarding what our product should and shouldn’t do.

I’m doing a lot more “CEO things” and loving it.

Related: 4 Things That All CEOs Hate

That doesn’t mean I’m done coding.

I still believe in keeping that part of the brain operating effectively.

However, I feel like I’m finally using my skills as an asset for working on the business instead of in it.

I was nervous that by not being involved in the day-to-day of product that I wouldn’t get to scratch my creative itch. But in reality, I’m able to create even more across the whole company -- with better clarity on what needs to be done -- and still feel like I’m making my mark.

As one of our advisors helped to describe it, instead of getting my hands dirty, I’m now “painting with influence.”