Before I dive in...
This is probably the most vulnerable I have been on the internet.
It's not meant to be a negative story, I've enjoyed the last decade of my life.
I fell (and sometimes still fall) into a trap inside my own head.
And have talked to friends who feel they have done the same.
I hope my experiences shed light on the dangers of trying to "fit in".
I made my first internet money when I was 13.
I sold an iPhone 4 on eBay. Super exciting I know haha
But seeing that $120 hit my PayPal account was an eye-opening moment.
I wanted to do it again.
So I did it 100+ times.
Buying and selling iPhones was my bread and butter.
But I wanted to do more.
I found an interesting crowd.
If you're familiar with BlackHatWorld you know what I mean by "interesting".
I was learning about anything I could do (legally) to make money online.
I went from flipping iPhones to flipping domains and datasets.
Buying and selling websites, dating apps, & blogs.
All from my mom's old Toshiba laptop.
I started making "real" money.
Eventually I realized selling services was the most sustainable route to cash.
It started with $1,000 Wix websites and progressed into managing Facebook pages & posts.
Social media growth was simple back then (this was 2013 btw).
Posting more = growing faster.
Companies would pay $2,000/month for one Facebook post a day.
Freelancers on Elance (OGs remember) would charge <$200 for the same service.
So I took advantage.
I became obsessed.
My friends wanted to play FIFA & GTA (so did I tbh).
But I was playing this secret internet money game.
Using a PayPal account as my personal scoreboard.
I stopped playing basketball.
Stopped caring about my classes.
Sat on my computer all night.
Note: High school was a blast.
I had a wake up call.
I lost my grandparents during senior year.
I wanted to enjoy my last summer with my friends.
So I sold my book of business to another BHW guy and "retired".
Not that I made enough to money to retire.
I just didn't want to play the game any more.
I was going to college to get a job in finance.
College was a challenge.
I was post break-up and living 3,000 miles from my family.
While trying to establish my own identity.
Everyone who goes to college is aware of this opportunity to "recreate yourself."
I tried to be what I thought would make me popular.
Cool, confident and successful.
What I thought was cool story turned into my personality.
It was my first time talking about it with anyone my age (or in-person).
I had ZERO idea how to navigate it and word spread fast.
"I met this guy that made a bunch of money in high school."
Unfortunately it felt like the one thing people seemed to like about me.
The only thing that made me "cool".
Admittedly, I leaned in.
Let me be clear.
I am NOT implying that the people I met were shallow.
I lacked the emotional maturity to understand...
That maybe they would've been my friends even without the "success".
They were good people and real friendships.
I had no sense of self-worth beyond my work.
I didn't believe I brought anything else to the table.
I was insecure and uncomfortable.
Craving attention and approval.
So I leaned into being the "entrepreneurship guy".
I tried to start businesses with my new friends.
I tried to socialize through working with people.
I was interested in apps so I tried to build & invest.
I had sold services in high school so started doing that again.
I saw people launching courses on the internet...so we tried that too.
If someone had a business idea, I wanted to be involved.
This was a mistake.
We tried (and failed) at basically everything.
At it's core, it was good-intentioned.
But the reality is...
You take a handful of 18-19 year olds who barely know each other...
And tell them to build a business (or a few at the same time)...
During their freshman year at a 30,000+ student university.
Without real business (or life) communication skills.
Without clear goals, roles and expectations.
Without 100% focus from anybody.
It ended exactly how you think it would.
At least we learned a bunch along the way.
College was fun, but it wasn't for me.
So I left.
I connected with an entrepreneur with a large personal brand.
And a massive exit under his belt.
He offered me an opportunity to join his new company.
It felt like a chance to dive into "real" entrepreneurship.
Or at least what social media had convinced me entrepreneurship was.
It was a major growth moment.
At first I was focused on getting better at building products.
Working with Fortune 500 clients at 19 years old.
Leveling up my skill set like crazy and getting recognition for it.
Not for what I had done in the past, but for what I was doing NOW.
Then I caught a glimpse of a new drug.
Personal branding.
I was blinded by the illusion of fame & money.
It was 2017 and I was at the epicenter of the Instagram earthquake.
I was flung into the word of influencers, info products and inflated results.
And all I could think to do was to try to keep up.
More followers, more money, and more validation.
A perfect storm for the insecure.
The pattern repeated itself.
I went back to Boston I got swept off my feet by fancy offices and promises of wealth.
Tried to be an "influencer" hoping to be liked by everyone else.
Don't get me wrong, it was fun.
There were plenty of dope experiences, people, and projects.
But it created a weird dynamic.
The better my life looked, the more validation I got.
"Look at my success, work with me."
I was both saying this and falling for it at the same time.
I wanted to work with people who I thought were richer, more famous, & more popular than me.
While positioning myself as rich, famous and popular so people would want to work with me.
It's a cycle visible at every level of society.
At my core, I was craving acceptance.
My best friend smoked so I started smoking.
My friends were selling courses so I sold courses.
My friends inflated numbers so I inflated numbers.
My college friends drank every weekend so I drank every weekend.
I kept trying to be the person I thought everyone wanted me to be.
It was a slippery slope.
I was stuck in a multi-year cycle of seeking validation.
Trying to live up to these perceived expectations.
And the whole time I should've been looking in the mirror.
Focused on accepting myself instead of trying to be accepted.
I do need to say this.
I am beyond grateful for the people I have shared experiences ("good" and "bad") with over the years.
None of this is meant to place any blame or responsibility on them.
We are all adults and I made my own decisions.
If you are reading this, I appreciate you and the memories.
Then there was a breakthrough.
I proactively walked away from a challenging situation.
Had the hard conversations (win!)
And moved in with my best friend.
The whiteboards in the kitchen were full of ideas.
The energy and vibes were immaculate.
It was a huge step in the right direction.
Some people travel, other people build.
We tried to get involved with any business we could.
We wanted to work on interesting things.
Yes, the goal was to make money (we did).
But the real benefit?
It was our first real opportunity to explore.
Ecom products, consulting, ebooks, communities, software.
We built and grew some really cool shit from the ground up.
Learned everything from sales to funnels to paid media.
And helped other creators & entrepreneurs do the same.
But it wasn't perfect.
We hit a few big road bumps.
Instagram blocking our API access 3 days post-launch.
One of the most insane client stories you've ever heard.
Moving to San Diego 7 days before COVID hit.
It was a wild ride, but at the end of the day...
Sometimes people want different things.
Don't get me wrong...a neon green Lambo is badass.
But I couldn't commit to the lifestyle it required at the time.
What started as a shared journey turned into separate paths.
I wish things ended on better terms but once we reached that point...
It was too messy.
I started feeling a shift at 24.
I took some time off before diving back in.
Traveled, spent time with my parents & reflected A LOT.
Decided to build something quietly.
Scaled a SaaS company to $30,000 MRR.
Without my personal brand.
Proved to myself that my value was more than an "influencer".
Proved I could build a successful business again.
Then I discovered Twitter.
I started with ~400 followers.
It was blissful - no expectations.
Just other people who loved to build things.
Some of my tweets did pretty well.
I started to build a bigger following.
It felt like the perfect opportunity to dive back in.
It was a similar story.
We built solid products, services, and companies.
Generated 7-8 figures of value for us and our customers.
A much bigger ecosystem with more money & people.
Just a few years of life/business wisdom missing.
My need for validation flared up again.
I was trying to be liked, instead of trying to be me.
Started to feel like I was back in freshman year.
Unorganized, unclear, and unhappy.
It wasn't working.
So I took a break.
I dismantled most of the portfolio.
Real talk...it was painful.
Sold the majority of my equity.
Gave a few of the businesses away.
And did something I never thought I would do.
I got a job.
I will probably share another story about this.
But the short version...
I was offered a dream role at a dream company.
Learned so much and built some crazy products.
Worked side by side with an ALL-STAR team.
And in the process, solidified my core group of true friends.
The ride or dies...
Who stuck around even when I wasn't an "entrepreneur".
They mean the world to me.
And now we are here.
I am stepping back into entrepreneurship full-time.
There is a sense of calm.
A deeper level of confidence in who I am...
In what I am building...
& who I am building with.
I haven't felt this level of excitement in a long time.
Probably since I sold that first iPhone on eBay.
So what's the point?
There have been countless lessons over the years.
But a big one?
Don't change yourself to find validation.
Don't obsess about fitting in.
Don't let other's opinions dictate your decisions.
Be yourself.
Do the work to find yourself.
And your people will find you.
As cliche as it sounds, its true.
It will take time, but it's worth it.
Accept yourself.
Nobody is perfect.
Accept your mistakes.
Most people are trying their best.
Give everyone the benefit of the doubt.
Including yourself.
Improve yourself.
Every experience is an opportunity to improve.
Don't let the pain hold you back.
The positives outweigh the negatives.
Keep moving forward and learn from your past.
You've probably learned a lot already.
Keep doing your best.
Live life with good intentions.
Have more hard conversations.
Enjoy the moments along the way.
And smile more.
Appreciate you reading this and hope it helped you in some way, shape or form.
Much love,
Sam
