A New Playbook

Why I'm not quitting my great job to work for myself.

I love my job. I want to build a tech “startup.” I’m sure I’m not the only person on the planet that wants to build a business but can’t afford (or doesn’t want) to quit their job, but so much of the startup wisdom and writing on the web seems to idolize those who quit their jobs, put it all on the line, and dive right in.

Well, I’m not going to do it that way. Instead, I’m going to venture out and try to build my own playbook.

My Background

I’ve been very fortunate in my life. I was born in the United States to a white father and a Brazilian mother. I went to college (at great expense, but we’ll come back to that one) and got a job in the video game industry immediately. The job wasn’t my favorite thing, but I was fortunate enough to find an opportunity to work at a small education technology startup building web apps for schools.

That startup got acquired by another startup, this time a well-funded Silicon Valley startup. Score! Fifteen months later, the second startup closed its doors, and for the first time, I was looking for work out of necessity.

No income coming in. A soft job market for product managers in Central Florida. No prospects. No network to rely on. No savings.

Fortunately, a friend of mine pointed me to Underdog.io and I was matched with a few top-tier companies almost immediately. A few interviews and plane trips later, I accepted a job working as a product manager for Pivotal Labs in Washington DC. From here, my career really took off. Job titles went up, salary went up, responsibility went up, job satisfaction went up.

From a career perspective, I have absolutely no regrets and nothing to complain about. In fact, I quite love what I do and who I get to do it with. There’s a bright future for the company I work for and my place in it.

However. You knew there was a however, right?

My Driving Factors

As I’ve set repeatedly in this post, I’m aware that I’m extremely fortunate and feel blessed. I also believe emotions don’t cancel each other out. It’s possible to be overly-satisfied in one area of your life and empty in another…it doesn’t average out to be “content.” All that being said, there are a few things that exist in my life causing me to keep pursuing the creation of my own thing. In the spirit of transparency, here they are:

  • The “Startup Itch.” I essentially started my career in startups and I can’t seem to stay away. While I work for a large enterprise now, I still do startup consulting and I teach at local accelerators. The excitement that comes with making something out of nothing is a huge rush.

  • Debt. I’m blessed with a great job, but it doesn’t erase the $180k of student debt I had when I finished college. A friend of mine has a beach house in New Smyrna, Florida, that costs less per month than my student loan payment…and it’s likely he’ll pay the house off faster than I get the loan paid.

  • Continuous Education. I love learning things, I love teaching things. When I teach the things I know, I end up knowing them better. When I know things better, I’m able to teach them better. If my wife had a nickel for every time I started a sentence with, “Did you know…” we’d be able to buy that beach house.

  • My Competitive Nature. I played sports all through my college graduation. I get a thrill from competing, and while I do get some direct competition in the job I have, it’s very different when it’s something I create or do myself. In track and field, for instance, every event I competed in was a “may the best man win” event. Knowing that my preparation, training, and performance was key to the outcome provided a sense of purpose that stuck with me. My exercise habits didn’t, but the spirit of competition did :)

  • Paranoia. I carry a lot of anxiety around income. Right now, my wife and I both work for the same company. If layoffs hit, there’s a chance we’re BOTH impacted. There are zero reasons to think we’ll get let go, but the odds are never zero. It doesn’t matter how large my paycheck is or how steady my job is, I will always have this paranoia if I only have one income stream coming in.

Okay, now that you have a sense of where I came from and why I think the way I do, let’s talk a bit about what I’m doing next.

“Deal With It and Adapt To It”

My wife is an incredible person. She’s also a patient person, and I’ve definitely taken advantage of that when it comes to this topic of building a business. Since we met in 2010, I’ve been talking about building my business. I think I’ve had 5 or 6 different LLC’s filed with the states we’ve lived in, all with the purpose of building a business. Anytime I talk about a “new thing” I’m working on, my wife rolls her eyes because she’s seen this play before.

In my day job, I literally teach companies how to transform into high-performing software organizations. The customers I work with have incredible outcomes. I know the playbook, and I wrote parts of it. I teach at startup accelerators and work with founders that end up building great businesses for themselves.

It’s frustrating. It’s a playbook I know so well, but the reality is it’s a playbook that won’t work for me. There’s a big difference in approach when you have 80 hours a week to focus on a project vs 1 hour each weeknight. There’s a big difference in mindset when you switch context after 8-9 hours of a complex job with a lot of responsibility. And, if we’re being honest, it’s hard to be motivated to do Thing B if Thing A is bringing in all the money.

The outcomes I’m chasing (multiple income streams, building something of value from scratch, paying down debt) are very different than the outcomes an “all-in founder” may chase, such as replacing their previous income, raising capital, building a team, etc. By comparison, what I want to do is quite simple. My wife agreed.

Rachel: You like teaching stuff. Pick a topic and teach a class. Just get it built and do it next Thursday night.
Andrew: But what about…
Rachel: Just get it built. You have one hour a night and 16 hours on the weekend. That’s your constraint, it’s reality, deal with it and adapt to it.

Working Within Constraints

I’m building a business based on reality. Specifically, it’s based on MY reality. What does that look like?

  • I have limited time.

  • I have a limited budget.

  • I have a large network of colleagues, customers, and contacts in the tech world.

  • I need the income from my job, and I love it too much to consider quitting.

  • I have expertise in product management, customer success, people management, facilitation, lean principles.

  • My superpower is making complex topics seem simple.

  • I can’t code, but I’m dang good with Bubble and have built projects for clients in the past. Whatever I build, I’ll do it myself without code.

  • I will lose motivation if I’m not seeing (or delivering) value quickly and often.

So, what am I gonna do? I’m doing three things:

  1. Building a web application to help founders and small teams build the right thing, build the thing right, and make their customers wildly successful. Expect an update on this product in next month’s post.

  2. Teaching what I know via live video sessions. The first one is scheduled for May 21 on Customer Onboarding! Click Here to check it out.

  3. Documenting the journey in this monthly blog/newsletter. Tell your friends!

In between written updates, you can find me on Twitter and LinkedIn. My Twitter will be focused on this adventure, while my LinkedIn will be balanced more toward my professional career.

I’m not sure how this journey will twist and turn, but I’m gonna figure it out. Without quitting my job.