I sold my blogging business, including the brand I spent 10 years building, The Modest Man.
Why?
Well, I’ll tell you the whole story. It’s a tale about searching for passion, trying desperately to escape the rat race, hustling, achieving freedom, about finding and then falling out of love.
Let’s go back to 2007…
To begin, we need to go way back to the quaint year of 2007:
- I just turned 22.
- George W. Bush is the President of the United States. Barrack Obama just declared his candidacy.
- Apple launches the first ever iPhone, and the last Harry Potter book is finally published.
- Low rise jeans, Ugg boots and Ed Hardy t-shirts are all the rage.
People are feeling good. The stock market is soaring, but The Great Recession is right around the corner.
I got a degree, but what now?
I’m about to graduate from the University of Maryland with a degree in psychology, and I have no idea what I want to do with my life.
It’s not the best job market heading into 2008, and I find myself getting rejected after interviews that I thought went pretty well.
I finally end up at a small communications firm in Washington, DC.
The entry-level life
On my $38k salary, I can’t afford to actually live in the city, so I move back in with my parents and battle rush hour traffic to get downtown every morning.
I don’t like my job, and I’m not good at it, but I like my co-workers, and it feels exciting to be in the city and making money, even if it wasn’t much.
I do this for 3 years, which was probably about 2.5 years too long.
I’m insecure at work. I don’t present well, and I’m out of my element interacting with clients.
I look very young. I’m short, I have a dumb haircut, and I don’t know how to dress like an adult.
Then, in 2009, two small but pivotal things happened at the same time:
First, after my boss tells me not to show up to a client meeting wearing my backpack ever again, I swallow my pride and ask a well-dressed, nicely-groomed colleague how he manages to look so sharp all the time.
He casually mentions that he gets all his clothes tailored, and a tiny lightbulb turns on.
Second, I read a book called The 4-Hour Work Week by Tim Ferris and discovered the concepts of passive income and location independence.
A small seed is planted.
Meanwhile, I experience heartbreak for the first time…
…when my long-term girlfriend I met in college finds someone new.
I don’t yet understand that time, and other women, will heal this wound.
So, professionally, romantically, financially…I’m not doing great.
And I can’t help but think that this 9-to-5 sit-at-a-desk for 40 years thing isn’t for me.
Outside of work, I’m getting more into music.
You see, I grew up playing classical piano and was actually pretty good.
I started playing drums in high school and spent much of my free time making hip-hop beats on my old desktop computer.
I wasn’t doing this for money. I just wanted to – needed to – create.
I’m itching to go deeper into music, so in 2010 (at 25 years old) I quit my job and start running a home recording studio above my parents’ garage.
I was having fun. I loved not having to battle rush hour and go to staff meetings and pretend to be working whenever someone walked by.
I even played drums in a couple of bands, which was awesome. I was spending lots of time doing deep, creative work, which is so fulfilling.
But I didn’t make any money, and my savings were drying up.
Back to the 9-to-5 life
So, when a friend told me about a cushy job opening up at a huge IT company he worked for, I bailed on my music industry dreams.
Once again, I took a job I didn’t want, that wasn’t a good fit. But this time I was making $60k a year, and I felt rich.
I got my own apartment. I bought a nice couch. I started dating again.
And, field by the likes of Tim Ferris and Pat Flynn, I started getting into online marketing.
2 interests converged
I was tinkering with WordPress, learning about SEO and affiliate marketing. I was enamored with the idea of making money online.
At the same time, I was feeling some pressure to fit into this new ultra-corporate environment that I was working in, so I slowly started to work on my personal style.
I started getting my clothes tailored and upgraded my shoes. I was reading menswear blogs and forums like Effortless Gent, Primer Magazine, and r/malefashionadvice.
I found a lot of solid advice, but…
I noticed that none of the menswear bloggers I followed were built like me (i.e., short and slim), and I wondered if this might be a good niche for my own blog.
I bought the horrible domain name, shortmanstyle.com, and quickly rebranded it to themodestman.com.
I thought “man of modest height” was a gentler, more subtle way of saying “short guy”.
On this blog, I started documenting my journey to upgrade my appearance. My early content was awkward and cringy, but I started to get some traffic.
I even started to make a little money.
Not much, mind you. 2013 was my first full year blogging, and made a whopping $1,844.
But even with these meager earnings, I was itching to get away. So I quit my job and went on a Tim Ferris style sabbatical, spending three months living on my own in Ecuador.
It was a great experience; I highly recommend an “early retirement” sabbatical.
But…when I got back home, I was unemployed (or as I like to call it, self-employed), and I needed cash.
A period of hustle
Themodestman.com was on course to make a cool $8k that year, in 2014, so I hit Craigslist HARD and got as digital marketing gigs as I could. After all, at this point, I knew enough about SEO to be dangerous.
In fact, these self-taught skills got me recruited for a digital media position at a large nonprofit in DC.
I took that job and actually loved it.
I got my own office. My co-workers were awesome. And I was making more money than ever before, a little over $90k a year.
Big life stuff
I bought a condo. I met my future wife.
I went even harder on my side hustle, working evenings, weekends and lunch breaks on The Modest Man.
I cold emailed other content creators and started making friends in the industry.
One of these friends was Aaron Marino, a.k.a. Alpha M, who convinced me to start this YouTube channel.
I started making videos with my phone, in my living room, poorly.
I was starting to believe that, maybe, this side hustle could make enough money to go full time. Maybe it had the potential to turn into a real business.
I liked my job, a lot, but I was still desperate to escape the corporate 9-to-5 rat race. The office life wasn’t for me. I had to get out.
Turning 30, moving out west
Then I turned 30, and man, this messed with my head a little bit.
I felt behind in life, so I worked harder than ever.
My little business grew to $3k/month. I was loving the hustle.
In 2016, my then girlfriend said she wanted to move back to her home state of Arizona, and I agreed to join her.
For the third time in my adult life, I quit my job.
I rented out my condo, packed my things and drove across the country to move in with the lady who I was increasingly sure I would marry.
We landed in Tucson, and just like that, our living expenses were cut in half.
Going Full-Time
This meant we could both focus full-time on our passions (hers being illustration and mine being The Modest Man)
The next couple years were great. We settled into a house and really made it our own.
Life was good
I started training Brazilian jiu jitsu, which was the first sport I really fell in love with.
And my blogging/YouTube business grew quickly, surpassing $100k annual revenue for the first time. That’s right: six figures baby 😆
I proposed to my girlfriend, she said yes, we got married.
Life was good!
Then, for some reason, in 2019, we threw a wrench in it.
Changing things up
Despite our comfy life, we’d both started itching for some sort of change.
I’d begun going to New York City somewhat regularly for a mix of work and play, and I’d always dreamed about actually living there.
Meanwhile, my wife became interested in this super-specialized art school in Rome (yeah, Rome, Italy).
We had a crazy thought: what if she went to Rome, and I went to New York, and we sort of went back and forth while she was in school, then maybe settle down in New York for a while.
An exciting plan, right? What could go wrong??
Bad timing…
Well, we made this move near the end of 2019. Covid hit Italy hard right at the beginning of 2020.
A few months later, it hit New York City.
My wife had to drop everything and come back to the US.
The two of us holed up in a 300 sq ft studio for a few months before ditching New York and migrating south to Richmond, VA — an awesome city btw.
It wasn’t an easy period, but we had good friends and were making the best of it.
But there was one silver lining: business was booming. Traffic to my blog had doubled from 2019 to 2021.
I also bought another blog about watches, theslenderwrist.com, from a fellow YouTuber, and that site took off really quickly.
My websites, plus this YouTube channel, had turned into a pretty lucrative little business.
I was making 3-4x more money than I ever did at a “real” job.
I got what I wanted, but…
In many ways, I had finally gotten exactly what I wanted: I’d escaped the rat race, had total control over my time, could live and work anywhere, and was on a path toward financial independence.
But despite all of this, I was becoming less and happy with my work life.
Things had changed.
My work was no longer a creative pursuit. It was a business. I sent much of my time hiring, managing and training people, building out operating procedures, responding to emails, bookkeeping, and doing all of the other admin work that goes along with running a company.
I wasn’t on that satisfying step part of the learning curve anymore. My work was incremental.
The most creative part of my “job” was making YouTube videos, but financially, YouTube was a small part of the business. It was hard to spend a lot of time making a video I could really be proud of when other parts of business needed my attention.
Plus, I had to meet deadlines from video sponsors. Honestly, this meant that I had phone it in sometimes, which feels terrible.
Falling out of love with work
I was falling out of love with the business. It was a cash cow, but I wasn’t enjoying the day-to-day.
So, I started thinking about an exit plan… maybe I could sell the business?
Becoming a dad
Then, in October 2021, everything changed when my daughter was born.
When you become a dad, sleep and discretionary time become scarce. Stress abounds.
Don’t get me wrong: having a kid is amazing. All the cliches you hear are true. They’re so freakin cute and everyone else’s baby is ugly except for yours.
But it’s tough, and it changes every aspect of your life, including where we wanted to live.
My wife and I decided to move back to Tucson, Arizona, in part to be closer to our little girl’s grandma, who was ready to help out as much as we needed.
We packed our things – again – and moved across the country, again.
A low point
Not gonna lie, it was a tough move. Our stuff was in storage for months while we looked for a house. We stayed with family, and I worked on a card table in my mother-in-law’s bedroom (thanks, Paula!).
It was sort of a low point for me, in terms of passion for my work and creative energy. I wasn’t in a great mood, and wasn’t my best self.
I just knew that it was time to turn the page.
I craved a simpler work life, more time for creativity, less time on management and administration.
And, frankly, I wanted to take some chips off the table.
Deciding to sell
I knew that I could sell my websites because I’d received offers in the past.
But I didn’t want to sell this YouTube channel. It’s too personal, and I wanted to keep making videos.
So, after many months of debate, I listed the business for sale: The Modest Man and The Slender Wrist (everything I was doing except for this YouTube channel).
I got a bunch of offers. I chose one, lawyered up, went through the due diligence ringer, signed a bunch of paperwork, and closed a couple months later.
It was a bit of an emotional rollercoaster, but it actually went pretty smoothly. I’d liken it to getting a mortgage and a proctology exam simultaneously.
Closed the deal
When the deal closed, I felt an enormous sense of relief. Not only was it the biggest financial transaction of my life, but it instantly shifted this mass of responsibility from my shoulders to someone else’s.
I knew it was the right decision.
In the weeks that followed, I did a lot of jiu-jitsu and played some Tears of the Kingdom. I spent a lot of time working on our new house and hanging out with family, and even did some traveling.
After hustling in the SEO/blogging business for 10+ years, it was a nice break.
What now?
My plan now is to focus on YouTube channel, as well as my personal social media accounts. Yeah, I’m one of those “personal brand” people now 🙄
I might even start an email newsletter one of these days. Well, technically, I have an email list (sign up below if you’d like). I’m just really bad at sending regular emails.
Or just keep an eye out for new articles here on this site and/or new videos from me on YouTube.
Either way, thanks for reading!