One to Zero
Going from employee to entrepreneur to employee again
Act I
Almost exactly four years ago, I was catching up with a friend who casually mentioned that I should look into a career in wealth management. At the time, we were nine months into government-enforced WFH and I felt stuck — both physically and psychologically — in the classic good-but-not-great job. I figured a potential move from institutional to personal finance was worth a look, so I made some calls.
Like many corporate drones employees, I’ve had my fair share of job-quitting dreams, but there were always obvious red flags and significant setbacks (i.e., excuses). But becoming a financial advisor wouldn’t be so much a career switch as a career shift: I had the degrees, the markets knowledge, the deep interest, and the soft skills. I just had to find a company willing to take a risk on someone with no clients, no connections, and no real experience.
After exploring opportunities at brokerage firms, insurance companies, and banks, it became quite clear that I belonged at an independent RIA. And thanks to Michael Kitces et al, I took this idea to the next level: why don’t I just start my own RIA? I’d always wanted to be a founder; now was as good a time as any. Thus began my entrepreneurial journey.
Act II
I’ll skip over the boring, mechanical parts of building a practice from scratch, but it took about 18 months before I was ready to launch. The first several weeks were slow-going, but I eventually brought on a couple clients. Then another, and another, and another… Next thing I knew, I had roughly 15 people/couples actually paying me to manage their money. WTF?!
Business wasn’t booming per se, but it did become cash-flow-positive quite quickly, meaning I was making money and having fun doing it — the holy grail of work. Best of all, my job was making an honest-to-goodness difference in peoples’ lives; for the first time in a 15-year career, I making an impact. And it was exhilarating.
But, truth be told, it wasn’t all rainbows and unicorns. Running a business, even (especially?) a one-man show, is difficult. Fissures of discontent began cracking the surface of fulfillment, and I started to question if the plan — for both my business and my life — was still viable. Then, during a short vacation, I asked myself a variant of Tim Ferriss’ question: “What would this look like if it were easy?”
Act III
For me, “easy” meant leveraging the resources of an established firm: experienced advisors, sophisticated software, trading and analytical tools, etc. The “pros” were obvious, but what about the “cons”? Looking back, there were five main reasons I decided to take a job again:
By the time I joined my new firm, I had been working from home for well over four years, and completely on my own for two. While the work-life balance was nice, over time it became a net-negative. I missed having a buffer between work and home life. I missed having a team. And — I can’t believe I’m saying this — I missed the office small-talk.
At first, I was gaining skills and knowledge at an ultra-rapid pace, but it didn’t take long for the learning curve to flattened out; every marginal hour of research was producing fewer results. And mastermind groups and online resources were only getting me so far. I learn best via the Socratic method and needed someone to sit down and teach me the more esoteric and complex financial planning topics.
As much as I enjoy being “the boss,” I’m not exactly world-class at self-accountability. On some level, work is just a series of carrots and sticks, and I learned that I’m much more productive when there’s a big stick. In other words, I thrive when there’s someone else to hold me accountable.
“What has two thumbs and is responsible for compiling investment reports, responding to regulators, closing the books, scheduling meetings, dealing with software issues, reviewing portfolios, editing podcasts…? This guy.” I was literally doing everything. As a jack-of-all-trades type, I was good at it, but past a certain point it wasn’t the best use of my time (and skillset).
We weren’t quite sleeping on a bare mattress and eating ramen every meal, but quitting my job definitely put a damper on discretionary spending. This would have been fine as a single 20-something, but with a growing family, I didn’t have the patience or grit to outlast the lean times until reaching “scale.”
Epilogue
Do I have any regrets about starting a business and shutting it down in less than three years? The short answer is a resounding hell no, for one simple reason: I’ll never have to ask, “what if?” In 40 years I’ll look back and be glad I gave it a shot, even if it didn’t quite work out as planned. And that, Dear Readers, is the regret minimization framework in action.
🤙🏼 Pura vida,
Sent with 💛 from Pittsburgh
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Disclaimer: Nothing in this newsletter should ever be considered investment advice.