LaSean Smith Deloitte Digital days. Lucien Pellegrin took these shots.

No Plans

Someone recently asked me how I planned my career. My answer? No plan. Well, not zero planning, but I don’t like the word. Here’s the dictionary definition for “career”: An occupation undertaken for a significant period of a person’s life and with opportunities for progress.

Something about that word always felt like you’re giving other people permission to control your progress. No thanks.

Rather than a plan, I had (and still have) a set of guiding personal principles:

That’s pretty much it. Not surprisingly, three of these five are reminders to myself on things I should not do. I really have to remind myself not to do things. Sticking to that ruleset is how I got to the current version of me. I’m not sure when these principles became easy to articulate. But even before I knew how to write them down, I’ve used a version of these to shape my large and small decisions. Here’s a snapshot of that journey.

LaSean Smith My mom. Virginia. That t-shirt introduced me to words on a shirt.

Playground Entrepreneur

Moxy. I had a lot of it as a child. On top of that, the ten-year old version of me was convinced that most adults didn’t know what they’re talking about. And I was determined not to listen to them. Even though that level of confidence created other problems for me, it helped me “get started” on new ideas even when I didn’t know what I was doing. One of those activities was opening my mobile candy store. My business was simple — load up my backpack with candy and sell it in the playground for double what I paid.

I started with Chick-O-Sticks. These are accidental vegan candy sticks made of peanut butter, coconut and lots of sugar. One of my favorites as a child. They sold okay. Very few peanut allergies back then. Plus there wasn’t much competition for allowance money on the playground. So they bought what I had.

But here’s the thing. I sold Chick-O-Sticks because I liked Chick-O-Sticks. Eventually, the other kids asked for other types of candy. I said nope — I sell Chick-O-Sticks. One day the playground revolted on me. All at once. I went home that day with all of the Chick-O-Sticks I came with. I sat in my room confused. I thought I could brute force the sale. Wrong. My sad little face finally gave in. A few days later I came back to the playground with what the people wanted — candy cigarettes and Ring Pops. Side Note: Here I am selling vices (sugar) made to look like other vices. SMH. I still packed a few of the unsold Chick-O-Sticks just because. I almost sold out my backpack that day (something I’d never done at that point). When I got home, I sat in my bedroom staring at my backpack for almost an hour. Then it finally clicked. That was my first lesson in business.

Note To Self: You don’t have it all figured out. Listen to the people. Give them what they need (or at least what they want).

LaSean Smith My first computer. Tandy MC-10. 4K RAM + 16K RAM Upgrade Module. Ballin'!

Cool Kids = Meh

I started college when I was 15 years old at a community college in Phoenix called South Mountain Community College (SMCC). Go Cougars. I had gotten my first computer (a TRS-80 MC-10) a few years earlier and I was addicted to that thing. When you’re in college, but still a minor , you have a lot of free time — even with all of the time I spent on my computer. The structured part of my day would end around 1p. I needed something to do.

My dad played guitar and had built a home recording studio at our house (pretty rare back then). He let me use the equipment and I started making beats for local rappers and singers. As you would expect, I never made much money selling $50 beats as a local teenage producer. My candy business actually made more money. But during that time I went from the nerdy computer guy to that dude who would make you famous if you bought one of his beats. Now, I never made any of those people famous — nor did I claim to. However, content was so hard to produce back then that anyone who could help other kids navigate audio or video production was automatically propelled to the “in-crowd”. By the time I was sixteen, I was selling beats to all sorts of random grownups and saw some seriously crazy things. That’s for another story, but I quickly learned from those experiences that influential social circles are mostly fabricated constructs. Nothing changes inside of you when go from unknown to cool kid. To that end, it’s dangerous to place too much value in how many people don’t know you or how many people do. And for me, my life has always ended up more complicated and messy when I had too much attention. I decided to ignore the positive external validation. Because as soon as you accept that, you have to accept some level of the negative external validation as well. So I sold my beats and kept it moving.

Note To Self: Being cool is about being your authentic self, not what/who other people claim you are.

LaSean Smith We went to Disney World after we finished boot camp. That's Andrew. Cool dude.


By seventeen, I had switched to another local community college called Mesa Community College (MCC). Go Thunderbirds. I graduated with an associate’s degree just before my eighteenth birthday and needed to do something beyond sell beats to retail workers and street pharmacists.

I could code (COBOL, Pascal and C back then), but that wasn’t worth much in the Valley of the Sun. Yeah, they still call it the Valley of the Sun. Its was hard to get work on production software. Plus I wasn’t doing myself any favors showing up to job interviews in bright red Jordan jerseys and acid washed jorts. So at best, I was landing temp data entry jobs and at worst weeklong construction jobs that I wasn’t built for. All of those jobs sucked. I didn’t have the playbook to even think about moving to another city where software was just beginning to eat the world. I felt stuck.

I would drive my mom’s Chevy Cavalier past this strip mall that was filled with recruiting offices for the military. Every branch was there. One day I just drove into the parking lot. After some back and forth between the US Air Force and the US Navy, the naval recruiter offered me a bonus called the Navy College Fund. That’s a GI Bill Kicker that provides additional tax free money to attend college when you get out of the military. The naval recruiter put together a better package and was a much better salesman. I joined the US Navy. I was still seventeen at the time and my parents had to sign for me to make it official. My mom cried. My dad said, “let him go.”

I landed in Orlando for boot camp and went from local producer to an unknown sailor. They cut off my Kid-n-Play high top fade and called me “Smitty”. I was trained as an avionics technician and repaired navigation systems on airplanes at NASNI on Coronado Island in California. My next four years in the military deserve their own story, so I’ll save that for another time. During that time I finished my undergrad degree (go Salukis) and met real music industry people.

LaSean Smith Old school recording studios. I love these spaces. Believe this room used a Neve console. That's Toni.

Blah, blah, blah

This is already getting long enough so I won’t go through the whole list, but a lot of really funny things happen in some of the next wave of stops. I worked at a company called MicroAge doing phone support for Apple when people needed tech support on their Macs. Helping 90s Mac users fix their computers over the phone was some of the best problem solving training I ever had. Did a stint as an IT support tech where the CFO gave me great advice and free Phoenix Suns tickets (Barkley and Kevin Johnson era). Got my first Master’s degree. Go Devils. Became a professional recording engineer and met some amazing artists. Learned how to build software for the web (outside of the classroom). Started and failed on a couple of my own software businesses. Finally found my way to software startups and worked as a developer. Became CTO of a venture backed business where we burned through every last dollar when the first dotcom bust hit. Did a stint in consulting.

Fled to business school and got an MBA (go Hoyas) while taking the train at night to continue working as a recording engineer. Had an amazing internship in LA during business school and passed on an offer to work in film and television to move to Philly full time and make records. And yeah, you don’t need an MBA for that. Came back to tech to work at Motorola on a Spotify-like streaming music service they were attempting to build. We were way too early. Was given the “opportunity” to move to Horsham, PA to work on set top boxes for the company. Pass. Came back to the west coast to work at Microsoft doing strategy work. Convinced Microsoft to pay for me to complete the professional screenwriting program at UCLA. Don’t get to claim the Bruins, but was a great opportunity to evolve how I think about stories. Of all of the corporate benefits I’ve ever received, that one was the best. Left Microsoft to start a mobile app company and got lucky on timing. Got my first personal exit.

Went back to consulting and started to dabble in real estate development. Neither were fun. Turns out I enjoy construction science more than I do actual real estate development. Started a free two-hour workshop on understanding real estate investing — because hey, there’s no reason for all that information I compiled to go to waste. I figured angel investing would be a better fit for me and made a decent number of early stage investments. That flamed out as well. Turns out I’m not mature enough to leave founders alone and angel investing isn’t for me. I left consulting and came back to Microsoft to work on future stuff. Wrote a book and started developing media projects again. Dusted off my website (which has been online in some fashion since the late 90s) and here I am telling this story.

Note To Self: All your random stops will come together and make sense one day if you stick to your personal guiding principles.

LaSean Smith Me at 39 years old. That's a while ago. The journey continues.

The Punchline

There are multiple chapters in many of the individual sentences above. I may sit down and sort them out at some point. There are some really funny ones, sad ones and some super fascinating people I’ve met along the way. Some of the best moments are the multiple times I’ve done stupid things that somehow worked out. Best I can tell is that 1) I’m blessed and 2) courage trumps intellect. I fancy myself as a pretty smart person and I’m telling you — I will bet on courageous people over smart people everyday of the week.

I’ve been fortunate to travel a lot of places and live in eleven cities. With that amount of change, you either become a loner or learn to quickly build new relationships. I chose the latter. The best part of this journey has been meeting interesting people and finding amazing moments. But here’s the thing. There’s no blueprint.

Turns out that most adults don’t know what they’re talking about (including me). Ten-year old LaSean was brilliant. Ha! But seriously, when you hear someone else’s journey it is an inspiration at best and almost never a playbook. There are too many variables to copy someone else’s path an expect predictable results. As my dad used to say, “post hoc, ergo propter hoc.”

The best professional advice I can give is to go out and explore the world. Use that stimuli as an input to figure out who you really are. Turn that into your personal guiding principles. Once you have those, spend time doing the things you love (or at least enjoy) with people that allow you to be your full authentic self. Make adjustments as you continue to evolve and never break the rules for money. And if all that leads to a great career along the way — well, count that as a bonus. Stay happy.

Places I've Lived

Chicago — Biggest number of my relatives are here.
Durham — Lived here for a startup job. Worked in Chapel Hill.
Flagstaff — My dad went to grad school here.
Memphis — Went to avionics training for the Navy.
Norfolk — My dad was stationed here for a while.
Orlando — Went to bootcamp here in the Navy.
Philadelphia — Lived here for a year after grad school.
Phoenix — My triple boomerang spot. Came back twice.
San Diego — Lived on Coronado Island (NASNI) when I was in the Navy.
Seattle — Move here for Microsoft. I’ve been here a while.
Washington DC — Went to grad school here.

Get money. Keep money.

Join 2,000+ subscribers to my free weekly newsletter — Infinite Runway. Every Sunday morning, you'll get one actionable tip to help start and automate your business.