The most epic failures of my life led to an amazing breakthrough

We are living with less than $200 in our bank accounts and credit card debt in the thousands. And I’m spending all of our money on random half-baked get rich quick ideas…

It is Autumn 2008.

I’m living on unemployment.
I got fired from my crappy IT recruiting job in New York City.

Even getting fired from a crappy job is terrible.

People made the conscious decision that I wasn’t good enough.
They sat around in their crappy office talking about how crappy I am and decided to fire me.

How am I too crappy to work at this crappy company in this crappy job?

This was the first time in my life that I felt a total lack of control.
I had other jobs, but I left them on my own terms. Because I was ready to move on.
Not because someone deemed me not good enough.

I had been good at everything my whole life.
Not great, but good. And with minimal effort.
My formula was minimum effort for lowest acceptable outcome.

Getting fired was a harsh reality.
For a southern boy from Georgia, working in New York City was a dream.
Take the subway everyday. Wear a suit.
A real bigshot.
I was making $30,000 per year.
In a sales job that didn’t pay commission.
Yeah, that actually exists.
I found it.

I’m not worth $30,000 per year. This was hard to accept.
But, it was my reality.

Being newly unemployed, I tell my roommates that I can’t pay my $900 rent.
I move out the same day.

My car has a shattered driver’s side window.
The idiot takes my Garmin GPS that is worth $44.
I would have given it to you.

The big city is swallowing me whole.

Needing shelter, I stay in my friend’s closet for free in the Upper East Side.
Seriously. A closet.
I spend a week drunk and depressed with two other friends that got fired.

I’m 100% out of money now. And no lines of credit.

I apply to be a server at a chain restaurant. I get denied.

Why is everyone else in charge of my life?

I’m coming to the cold, hard truth that life can be really hard.
Something I had, fortunately, never experienced.

At the same time, I’m talking to my former college tennis coach, Chase Hodges, who is now a friend.
He invites me to coach with him at Drake University in Iowa.

Since I’m broke and living in a closet, not a hard decision.

I apply for a credit card and somehow get approved.
$1,000 limit.

Perfect, plenty for a flight to Georgia to get my car and drive to Iowa.
After 6 months in Iowa together, Chase takes a job in Atlanta and I follow suit.

Internally, I’m telling myself that I’m useless and can’t succeed outside of the tennis realm.
Which is what has defined my whole life.
I played tennis growing up.
I received a college scholarship for tennis.
I coached tennis after college.
I can’t escape it.

It’s a better lifestyle than an office job, but I need to prove myself outside of tennis.
I’m not off to a good start.

Once in Atlanta, a friend introduces me to this guy named John.
My friend says I absolutely have to meet him for coffee.
Without hesitation, I agree.

I’m sitting at Panera Bread in Atlanta.
Directly across from me is John.
John is slick. In a good way.
He’s well-spoken.
Charming.
Kind.

I like him immediately.

After some small talk and rapport building, he takes inventory of my life and my journey up to this point.
He spends a fair amount of time subtly alluding to how terrible my life is.
And he doesn’t stop.
He digs deep into my hardships, my failures, my lack of control.
He creates new pain that I didn’t even know existed.

Now I really know how crappy my life truly is.

After tearing me down, he asks what I’d actually like my life to look like.

“Ummm, I don’t know. A house, a wife, a good job that I don’t get fired from. Maybe kids?”

John doesn’t like this answer.

So, he asks what I would want in life without restriction.
Without limitation.

My answers are pretty basic.
“A mountain house. An ATV. Maybe a hot tub if we can afford it.”

He’s still not satisfied.

“What about an airplane? What about a mansion with tennis courts? What about a yacht? What about the sexiest woman you could ever imagine? Why are you limiting yourself?”

Well, I can’t argue any of that.
So, yes.
Yes, John. That’s what I want.
All of it.

“Well, is your current life going to get you all of those things? All of those things that you deserve?”

“Well, no John. My current life is most definitely not leading me to those things.”

John hands me a packet with some information, smiles and says, “Welcome to your new life. Welcome to MonaVie.”

Enter business failure numero uno.

It’s a tale as old as time.
And one you’ve either been on the giving or receiving end of.

I start hustling my friends, my family, my roommates, people I meet on the streets, my waitresses.
There is no shame in my game.
I need that yacht. That jet. That mansion.

Needless to say, I make people hate me.
And I start hating myself. Even more.
I spend a lot of money on product each month that I never use.

I go to a lot of awkward meetings with people that say they are successful.
But clearly are not.

Welcome to the disgusting world of network marketing (sure, send me messages why your MLM is different).

The silver lining. And there is always a silver lining.

A compact disc.

A compact disc that came in the information packet John gave me when I signed up.
“The Strangest Secret” by Earl Nightingale.

MonaVie is my introduction to the world of self growth.

A shift in mindset that takes me from believing that others control my destiny to realizing that I control my destiny.
And my choices.

It’s a revelation to me.

Obviously MonaVie isn’t the right vehicle, but at least this world of “entrepreneurship” exists.
And I now know it exists.

I’ve never heard of self-help, entrepreneurship or anything closely related.
I was stuck in tennis land with blinders on from the age of 12 to 24.
Nothing else mattered.

But, now I need out of tennis.
I need to get rich. Jets, yachts, mansions.

I start devouring books.
This is completely brand new stuff to me.

Some of the books talked about getting rich through sales.
The highest paying job in the world.
So, I look for sales jobs.
I find one.

I go to San Diego for six weeks of “Survivor” style training.
If you’re still standing at the end, you have a job.
They will send you to one of their offices somewhere in the country.

I’m crushing sales books.
Learning all the tips and tricks from the greats.
And I make it through the gauntlet to the very end.

I get sent to Dallas, Texas.
I wanted to stay at the San Diego office.
No such luck.

Dallas is terrible. Or maybe it’s the job I hate.
I don’t know.
I’m working in an office with only two other people, that’s it.
And the guy I’m working for is a dick.

I last three months. Everyday is awful.

I stay three months to get a travel stipend that we were guaranteed on day 90.
If I hadn’t quit, I would have been fired shortly after.

When I don’t give a rip about what I’m working on, I don’t try.
Or, maybe it’s that I just don’t care. Which ultimately leads to not trying.
Even if it’s my job and my responsibility.

I need to gain more control over my life.
I want to work on something that I actually care about.

I spend a lot of time talking to my friend, Christie.

She’s my sounding board and voice of reason amongst the internal chaos and instability.

She suggests a conversation with her father.
He is in charge of west coast expansion for Chick-fil-a, mainly in California.

I end up on a one year assignment in Orange County California learning to operate the business at a restaurant.

I apprentice under the existing owner/operator of the business.
I start in the kitchen learning to bread filets, clean the kitchen equipment and prepare orders.

I learned a lot, but I still felt suffocated. It didn’t feel right.
I decided to quit.
With no other prospects. No other jobs.
Maybe it was just self-sabotage.
I had a clear path to making six figures and it was too easy.

I start hustling tennis lessons and am making about $400/week.
At the same time, Jacklyn and I are living in Costa Mesa with a strung out single mom in a disgusting apartment.

What did I just do?

Why would I quit a path to six figures to go back to struggling with tennis?
I had never made $50K/year, much less six figures.

In the meantime, I’m researching online about businesses to start.
I find the golden ticket.
Fit Body Bootcamps. I’m going to get rich.
I buy the course and start to take action.
It tells me I need to create cardboard lead generation boxes.

The closest place that can do same-day orders is in Compton.
I place the order for 100 boxes to be made with custom labels.
I drive up and back uneventfully retrieving my 100 flat boxes.
I still have to fold them all together for a finished product before I can start placing them in Subways and Jamba Juices.
To collect all my leads.
And of course, get rich.

While Jacklyn is at work, I spend hours putting together these boxes in our tiny bedroom at this disgusting apartment.
The room is so small that the 100 boxes cover the entire room.
We don't have a bed and use five layers of blankets to make the floor less hard.
You can’t see the floor/bed at all.

I know I’m onto something. This is it.
The business of my dreams and now I have a step by step process to execute on.
Nevermind that I have no interest in fitness or training or hosting boot camps.
I have boxes, and I’m putting them together.

By the time Jacklyn comes home to our disgusting apartment, I have about half the boxes put together.

As she walks in, I’m beaming with joy.

I think this is the greatest thing that’s ever happened to us.
I have a step by step plan that is going to get us rich.
And these boxes are our vehicle.

She starts laughing uncontrollably.
She thinks it’s the funniest thing she’s ever seen.
And it’s even funnier to her that I’m so proud of it.
I get mad and vow to prove her wrong.

I place boxes in Subways and Jamba Juices around Orange County.
I check back every couple of days. Across 50 boxes I get seven leads.
Three are real leads.
The other four tell me some not so nice things.
Said in a few different ways.

Three leads in two weeks across 50 boxes.
Meanwhile, the other 50 boxes are still in our bedroom taking up all of our space.

I come home to Jacklyn walking out boxes to the dumpster.
She tosses all of them.
I don’t blame her.
What am I doing?
Buy a course on starting a bootcamp business.
Buy 100 boxes with custom labels.

We are living with less than $200 in our bank accounts and credit card debt in the thousands.
And I’m spending all of our money on random half-baked get rich quick ideas.
Months earlier, I maxed out my only credit card buying Jacklyn’s engagement ring.
Even though she didn’t care about the ring, it was important to me.
It was enormous stress, but I’d do it again.

Simultaneously, I’m part of a new MLM called Isagenix.

I continue to bombard my family, my friends and everyone I meet with this “exciting opportunity.”
Everyone hates me for it.
I don't blame them.

It’s August 2011.

Jacklyn and I sell each of our cars and most of our belongings.
Next month we get married and head to New Zealand for four months.
I’ll try to make enough money through a tennis job while there to pay for our travel.
An extended honeymoon of sorts before we face “real life” together.

We have a little cash now from selling cars and belongings.
Although an old, beat down Ford Focus doesn’t go for much these days.
Jacklyn’s Chrysler Sebring owes some money, so we net maybe a grand on the cars.

Jacklyn is on the outs with her family.
They don’t want her to marry me anymore. I’m not sure why.
They aren’t coming to the wedding.
It’s hard for her.
On the positive side, after the wedding, our life of adventure and travel begins.

Isagenix did end up paying for our $2500 wedding.
It was my total profit for the venture.
For that, I’m grateful.
And the products are actually good, I think.
Or maybe they just told me they were good.
Like they told me I would be rich.

The $2500 profit wasn’t worth bombarding my entire rolodex over.
My former high school classmates. My college friends.
My family. Again.
Ugh.
Painful and shameful.
If I had to guess, I would bet my mom still has Isagenix products at her house today.
Sorry, mom.

Five months pass.

It’s January 2012.
We just arrived in Naples, Florida.
New Zealand, while a great experience, left us broke four months into our marriage.
Planning isn’t a strength of mine.
And not enough planning went into this. Cost exceeded tennis income.
Not a favorable equation. A huge travel fail.

A family friend, and career employee for Delta, provided us two buddy passes to return from New Zealand.
We weren’t able to afford tickets back otherwise.

Now we’re back in the US.
And we’re car-less, jobless, homeless and moneyless at 26 years old.

My childhood friend, Jeff, is living in Naples and lets us crash at his place.
We didn’t really have a plan beyond that.
It was shelter and had running water.
And we were living with a friend that cared for us.
Check.

Jacklyn gets a job at a wine bar in a shopping center about a mile away.
She walks everyday to get there. No car.

I try to find a tennis job to no avail.

Ashamed that Jacklyn is the only one bringing in cash, I apply to be a server.
I tell them I have experience. I don’t.
They can tell.

At 26 years old with a college degree and a few years of work experience, I’m unemployable to the service industry.

I’m now constantly on online forums trying to figure out how to make quick cash.
Someone posts about how they are successfully flipping video games.
I can do that.
I contact a video game seller from craigslist and arrange a meeting.
I meet a 13 year old in the Barnes & Noble parking lot.
I lowball him.
He stands his ground, so I give in and buy the games.
I am never able to sell them.

Life at this time is incredibly difficult.
Jacklyn is working herself to the bone and I’m starting to face a bleak reality.
I can’t get a job, and I’m getting hustled by 13 year olds.

Jacklyn is probably wondering what the hell she got herself into.

This isn’t the ideal circumstance for a brand new marriage.
It’s not just a brand new marriage.
It’s still a brand new relationship.
Jacklyn and I got engaged two months after dating.
We married a swift seven months after that.
We truly don’t know each other very well. At all.

And now we’re homeless, car-less, jobless and moneyless.
Other than the cash she is pulling from the wine bar.

After about two months of struggle, I start talking to a guy that worked at the crappy NYC company that fired me in 2008.
He was now a manager at a payroll company in the San Francisco area.
And he said he had a job available.

I’d never spent much time in SF, but that’s okay, I’m in.
I don’t really have a choice. I have to support us.
But, how are we going to make this happen?
We have very little money and we don’t have a car, nor can we afford one.

Fortunately, another childhood friend, Nic Lloyd, lived in San Francisco and had a truck he never used.
He offered us to use it for free.
A lifesaver.
And something I didn’t express enough gratitude for.
Something I took for granted.

The third day on the job, I was expected to drive to a Bank of the West in San Jose to deliver some donuts to the bank staff.

A popular bribe in exchange for business leads in that industry.

The only place to park was in a tiny parking garage.
On my way out, I take a tight corner, but think I make it out okay.
I drive back to our apartment 30 minutes away in San Mateo uneventfully.

As I get out, I notice the entire side was completely scraped and damaged with dents.
It was bad.
How did I not notice this?
It was a big truck, but how could I not feel this happen on that tight turn?

Regardless, I’m screwed.
We just moved into this apartment using nearly every dollar to our name to afford rent and a deposit.
How can I possibly explain this to Nic?
How can I possibly afford to get this fixed?

The answer is, I don’t. To either.

I don’t tell Nic, and I drive it as is.
For now.
In two weeks, I’ll get my first paycheck.
Then I’ll get it fixed without telling him.

I got home about 3pm that day.
It was my third day on the job and I already hated it with a passion.
I was a donut delivery guy dressed in a cheap suit with ugly dress shoes.
Bribing banks for payroll leads with donuts.
Shoot me.

I walk inside the apartment and tell Jacklyn what happened with the truck.
I’m devastated.
It was one of those compounding failures.
Stacking one on top of the next.
I hate this new job that we moved across the country for.
I wrecked my friend’s truck.
I don’t have a paycheck yet and the truck issue doesn’t help.

We have a one bedroom apartment, but never use the bedroom.

We found a sofa bed on craiglist for $40 and put that in the living room.
It stays in bed mode since we sleep on it every night.
This is an upgrade though.
In Costa Mesa, the floor was our bed.

I walk in and don’t say a word to Jacklyn. In my full suit, I crawl into the sofa bed and wonder if life will ever get easier.
Up to this point, it’s the most depressed I have ever been in my entire life.

“Why the hell is Jacklyn with me? I’m a complete failure. Everything I touch turns to crap.”

I stayed in bed from 3pm until 8am the next day.
Just laying in misery.

Eventually, I get it together enough to make a plan.

I find a body shop in San Jose that will fix the truck for $700.
Yelp reviews are excellent. I’m in.
They fix it and it looks as good as new.

I’m ecstatic, but still paranoid that Nic will notice.
He never does.
And by reading this, it will be the first time that he finds out.
Sorry, Nic.

Up to this point, I felt like life was happening to me, definitely not for me.
A lack of control.
Something Tony Robbins talks a lot about.
But, what if it was actually happening for me?
What if these experiences were necessary for the grand plan?

I don’t know if this is the case, but it’s a great reframe to stop playing the victim.
Which I was getting really good at.

I’m a donut delivery guy in a suit for about three months.
I did sell some payroll services.
I got some decent commission checks.
Yes, this sales job paid commission.
Another upgrade.

But, I just can’t stand it anymore.
I stop going to the office as much.
Some days I stay home and just tell my boss I’m delivering donuts.
Even though I’m not.
If I sound like a bad employee, it’s because I am.

I found a job at a startup in San Francisco proper.
We left our lease early in San Mateo and moved to a sketchy area in SF.
Lower Nob Hill on the border of the Tenderloin.
Crackheads, prostitutes, crime.

The startup I was working at was based in the Tenderloin for tax credits.
Perfect, I can walk to work.

I stay and get promoted at that job from an entry level sales person to working in advertising operations.
I’m trafficking ad campaigns that the pharma sales team closes.
It was fun to learn something new at first, but it eventually became mindless work.
AI will destroy that job soon.

Lack of control.

Looking to move near my mom, the company allows me to work remote from Georgia.
Our expenses drop nearly in half. My salary stays the same.
Financially, we can finally breathe.
Jacklyn is bringing home cash daily from a restaurant.
My income is stable.

We are living on an island off the coast of Georgia.
Low external stress.
Life is good, right?

Wrong. I was miserable.
Even though we finally got to a place where we weren’t super stressed financially, I was so dissatisfied in myself.
I knew I was destined for greater things, but why wasn’t I making it happen?

At this point, VacaPro was the eighth business I started and ultimately failed at.

I was constantly reading business books, listening to podcasts, doing Hal Elrod's Miracle Morning routine.

Am I just too stupid to figure out this business thing?
Am I just not capable?
How many books do I need to read?
How many podcasts do I need to listen to?
Until I’m “ready.”

Even though we finally got to equilibrium externally, I was dying internally.
Why can’t I just be happy and satisfied with my current circumstance?
What’s wrong with me?
Do I have to sabotage everything when, for the first time ever, life is good?

This is when I had my line in the sand moment.
In a coffee shop.
Crying audibly because I was so dissatisfied with myself.
It was the moment of no return.
The moment where I truly DECIDED to make this entrepreneurship thing work.

And, by God, it worked.

Rob Nunnery is the Creator & Host of FailOn.com and The Fail On Podcast, a platform that believes embracing failure and sharing your honest struggle is the only way to achieve your dreams.

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