The Last Cubicle
It took me less than ten minutes to realize that my first college internship wasn’t for me.
The dreary beige cubicle. The mindless database admin work. It felt like a part of me died every minute I was there.
I felt no connection to my coworkers. How could these people be so lost and hypnotized to tolerate this miserable place?
I was 21 years old and had a summer internship at the Madison Chamber of Commerce.
I hardly lasted a few weeks. Soon, I stopped showing up completely. It was that unbearable.
There are other options out there, right? This can’t be what my future has in store for me.
As college was ending, I was gearing up to enter into the “real world”. Like most of my friends, I wasn’t looking forward to graduating, getting a job, and slowly becoming bitter about life. Unlike them, I was desperately looking for a way out.
Deep down I knew there was another way. Though I had no idea what it looked like.
After graduation, I opted for a year of adventure: teaching English in South Korea. I still didn’t know what I wanted to do with my life, but I figured that spending a year living in and exploring Asia would help me figure it out. And it beat sitting in another cubicle.
As my year in South Korea was drawing to a close, the angst around ‘what to do next’ started to creep in.
The memory of my first cubicle experience stayed with me like a food allergy. Just thinking about it stirred up anxiety. I needed something different.
But what?
I decided to delay my return back to the USA and travel for a few months backpacking through Vietnam, Cambodia and Thailand. I thought I’d lean into the adventure in hopes I’d somehow ‘figure my shit out’ during this trip.
Well, the universe works in mysterious ways! That backpacking trip brought me exactly what I needed. It led me to one conversation that would change the course of my life forever. Which kick-started my career as an entrepreneur.
Fast forward and my entrepreneurial journey has concluded its first decade. Ten years of trying and failing and trying again, business conferences and business partners all over the world, hiring, firing, and more.
I would never have imagined what the journey had in store for me.
From being broke and moving back home to meeting millionaire mentors. From selling a business for nearly a million dollars on a whim to getting forced out of another business by a partner, it’s been quite a ride. And it all has led me to accept the inevitable challenges of life all while seeking more purpose.
Looking back on my last ten years since I first decided a “real job” in the “real world” wasn’t for me, a few stories and lessons stick out. While I may not have realized it at the time, these experiences were most impactful for me. By sharing them here in great detail, I hope they can be impactful, inspiring, and helpful for you, too.
The first story starts in Pai, a small town in Northern Thailand, where I met a mysterious man who changed the course of my life forever. Not all conversations change the trajectory of your life in a wild way, but this one surely did.
1. The Curious Man That Changed the Course of my Life (Pai, Thailand, October 2011)
The bamboo thatched roofs against the green rice fields were a striking backdrop as we rode up the dirt road to our hostel. Checking in and settling into our ‘tree house style’ dorm, I had no idea my life would be changed forever during my stay.
It was the fall of 2011 and I had just finished a year of teaching English in South Korea. I was at a crossroads in my life and not sure what I wanted to do next.
On a whim my travel partner Johnathan and I decided to alter our plans, as one often does on backpacking trips. On the recommendation of fellow travelers we rode through the mountains a few hours north of Chiang Mai to visit Pai. I could never have anticipated how that single decision would change the course of my life forever.
The second night of our stay our group was gathering to get ready for a night out. I noticed someone new in the hostel common area that caught my attention. He was an older man in his late 30s compared to most of us mid 20-year olds staying at the hostel. He was energetically engaging a group of other hostel guests in one corner of the room.
“What is this dude doing staying at a hostel like this?” I wondered.
But as I joined in the conversation I became captivated. REALLY captivated.
His name was Andrew and he was sharing about his life traveling around the world working from his computer. I could not believe what I was hearing!
Andrew was the first Digital Nomad that I had ever met. I didn’t know that term even existed at the time. He was running his sales business from his computer with a few VAs from Indonesia and India.
He introduced me to the concept of outsourcing, SEO and internet marketing which completely blew my mind! But what really ignited a fire inside me was the idea of building a business that gave you the freedom to travel the world indefinitely.
I had no idea that these things or this sort of lifestyle was possible. The more we spoke the more convinced I became that THAT was the life I wanted. Suddenly, a flip inside of me switched on and now my direction was crystal clear.
Andrew gave me the idea to build lead generation websites for high ticket service businesses and use SEO to generate leads. Then sell the leads.
The more Andrew and I spoke the more excited I became about the possibility of building an online business. I told Andrew I loved this idea and would try it.
“No,” he said.
I felt shocked and confused at his remark.
Like a wise Yoda, he replied with “Don’t try it, just DO it. There are other people out there doing this already. And you can too.”
Andrew’s words rang through my head the entire 3.5-hour ride back to Chiang Mai and throughout the rest of my trip.
Just do it.
Those words were burned into my brain and I became obsessed with ‘doing it’.
When I got back to the USA I got straight to work. I’d never been so inspired and motivated in my life! I committed to ‘doing it’ like Andrew told me.
Which brings us to our first lesson: Just do it.
When given an opportunity or seized by inspiration, lean in and just do it.
Take the leap. Follow the omens.
You’ll never achieve anything you dream if you don’t first take the leap.
Just do it. And I did just that. I dove in. With nothing to lose, I committed to my new dream and got to work.
It’s crazy how one conversation with a strange man in the mountains of Thailand changed everything for me. Little did I know, this “just do it” high would not last. Soon, I found myself depressed, anxious, and nearly out of money.
2. Down in my Mom’s Basement (Chicago, summer 2012)
You know the saying, “what goes up must come down”? Well, after meeting Andrew, I definitely felt every cell in my body going up. But it wasn’t long until I came crashing down. And boy did that hurt.
Fast forward to the summer of 2012 and I was depressed and having trouble getting out of bed. I was drinking WAY too much iced-coffee trying to motivate myself, my anxiety levels were increasing by the day, and my money was running out. I didn’t know what to do.
The ‘plan’ that I was SO excited about six months prior wasn’t working..
I figured out how to hire people to build websites on odesk (now upwork) and hired a bunch of SEO ‘experts’ from India for $2/hour. But my sites weren’t ranking and I wasn’t generating leads. I wasn’t making any money.
I felt so lost and distant from the high I was so sure about just months earlier.
What do I do now? Do I admit defeat and get a job? Had I failed too fast?
My savings were running out and I soon wouldn’t be able to afford living on my own. Anxious and desperate for a change, I reached out to the few entrepreneurs that I was aware of hoping for some miraculous epiphany.
One of those people I reached out to was my friend’s older brother Max. Max had been running his own businesses since highschool and was one of the few successful entrepreneurs I was even remotely connected to at the time. We didn’t know each other personally but he was generous enough to take a call with me.
On our call he gave me some advice. If I didn’t receive this at that time, I would not be sitting here writing this.
I explained my situation, my wants, my dreams, my plans, and how they weren’t working. How I didn’t know what to do.
Max generously listened to me and shared his perspective. And that made all the difference.
He told me that I was young (I was 24 at the time) and that since I had no other obligations/commitments, I didn’t have much to lose from keeping trying. He said that if I really was committed to my dreams then I should do whatever I had to do to keep pursuing them. In short, he encouraged me to push through. At all costs.
Which in this case meant swallowing my pride, cutting my expenses and moving back home so I could keep on pursuing my dreams. The worst case scenario would be that a year later if things weren’t working out for me I could get a job then. This didn’t excite me, but at least I had clarity.
As long as I could keep on pursuing my dreams like Max advised, I was gonna push through.
So I did.
This was my first (and certainly not last) brush with adversity in my entrepreneurial career. And the commitment to pushing through made all the difference.
I could have given up and gotten a job. I probably would have been okay.
But that wasn’t my dream. My dream was to build my own business and travel the world like Andrew. As long as I could keep pursuing my dreams, I would.
I didn’t realize it at the time, but it was with that decision to move back home that started to turn things around for myself and my career.
Sometimes you gotta swallow your pride and do the hard thing to keep on progressing. The path is going to get bumpy. Guaranteed.
When that happens you’re going to have a choice to make. Do you give up? Do you settle? Or, do you set your pride aside and do what you have to do to keep moving forward? The choice is up to you. And it can make ALL the difference.
So I moved back home and I got to work. I didn’t care about labels or what other people thought about me. I was a young entrepreneur living at my mom’s house and I had nothing to lose.
Soon, I started making some money and building more skills freelancing on odesk. Things started to look up! But I knew something was missing.
Though I was making progress, I was lonely and didn’t have anyone to talk to about my business and my dreams. None of my friends in Minneapolis were entrepreneurs. I felt isolated and exhausted from constantly explaining myself to others.
I thought about people like Andrew and Max and how inspiring they were. I began to wonder, “Are there other people out there with similar goals as me or do I have to go for this all by myself? If there are other people on this path, where are they and how can I find them?”
Within a matter of months, my quasi-prayers were answered. I had found my tribe! There were other internet entrepreneurs passionate about traveling, freedom, and wellness. They weren’t nearby, though.
I discovered a community through a podcast called Tropical MBA. Without having met anyone in person, I joined their online community and booked a one-way ticket to Thailand.
Little did I know, I was about to experience some sort of initiation.
3. Finding My Tribe (Bangkok, October 2013)
The air was thick with humidity and excitement as I touched down in Bangkok in October of 2013. I was exhausted from traveling halfway around the world but buzzing in anticipation of the upcoming event.
The event was called DCBKK (which stands for Dynamite Circle Bangkok) and it was for the community of location independent entrepreneurs that I joined a few months prior.
I was so inspired by the podcast where I heard stories of the amazing people and community in Asia that I bought a one-way ticket and committed to the event.
When I finally arrived, it didn’t take long for me to realize that something BIG was shifting for me.
I felt like I was high the entire week leading up to the start of the conference. Remember the inspiration that I felt when I initially met Andrew? It felt like that but it was increasing each day! I was bouncing from meetups to co-working to group meals. Each new person I met blew my mind even more.
My internal chatter was buzzing. “Wow, Everyone is so cool!! And inspiring!! And interested in all the same weird things as me!! This is amazing!”
I’ll never forget the feeling of ‘finding my tribe’. That feeling in a taxi on my way home reflecting on another amazing night meeting person after person who actually ‘got me’. I realized that I genuinely felt connected to each person I spoke to. We were all weird in the same ways. This was a stark contrast from previous nights out and trying to connect with people who looked at me like I was crazy when I told them about my life and dreams.
I didn’t realize I was a black sheep until I met 200 other black sheep just like me. Then, I reveled in the fact that I was a black sheep and wanted to be nothing else.
Entrepreneurship is a lonely road and impossible if you don’t have like minded people around you.
Find your community. It’ll change everything.
Your community will become your support system and inspiration. This is crucial for your long term success as an entrepreneur.
Though one potential challenge of an amazing and high achieving community is that it will humble you and make you feel small at times.
For me, being around others made me realize how little I knew about building a business. I felt like a baby compared to these other entrepreneurs who had been building their businesses for years. Until then, I had no idea what it meant to run a REAL business. I was just doing anything I could to make money. I realized I had to learn about how to build a real business. And this was daunting, because there was no road map to follow that guaranteed success.
4. Building a “Real” Business (Saigon, Vietnam, 2014)
“Hello! You! Motorbike? Where you go? You want massage?” yelled an old man as he smoked a cigarette.
“No,” I shook my head and looked away. He puffed out a ball of smoke and reclined back on his motorbike as if it was a couch.
The DCBKK event had ended and I followed my new best friends to Saigon, Vietnam, which became my home for the next four years.
I engrossed myself in the expat online business community. I spent much of my time at cafés, restaurants, and bars meeting close friends, business partners, mentors, employees and more.
I had found my tribe, my community. This propelled me to take my life and career to new heights. For me, this meant creating a REAL business instead of freelancing and saying “yes” to any paying gig I could land.
A few years and a handful of attempts at different business models later, I finally found something that hit: selling physical products on Amazon.com. From the spring to the winter of 2015, my sales doubled every single month. Then, I achieved my first 6-figure sales month in December to close out the year.
I would have never known about this business model if I wasn’t hanging with so many other entrepreneurs who wanted the same things as me.
When I first started making money freelancing I still dreamed of building a ‘real business’. A business that I could work ON and not IN. That I could really scale.
Now I had found it, but I struggled to deal with the challenges that still lay before me.
I was burning the candle at both ends: staying up late at night to coordinate shipments with my freight forwarder in California while working during the days communicating with my factories in China.
Sales were growing, but I was nearing burnout. My income was finally stable, yet my physical health was not.
I needed help, and I needed help FAST. I spent several hours on different websites trying to hire but it was exhausting and turned out to be a waste of time.
One day I was co-working at a cafe in the heart of Saigon (Ho Chi Minh City) and I was inspired by a fellow expat entrepreneur.
This person was a marketing consultant who built funnels for clients. If you aren’t familiar, a marketing funnel is a system that filters eyeballs/attention into prospects into leads into sales… like a funnel.
Long story short, I was so inspired by this funnel idea that I built one to help improve the hiring process. It ended up being the perfect thing for what I needed at the time. And it worked like a charm.
It turned my hiring process (or lack thereof) from a mess into an efficient and effective system. I soon found great people to fill any role and gained my social life back.
Shortly after, I was able to build out my team, which allowed the business to keep scaling. Revenue continued to grow, this time without overwork and overwhelm.
This was a great lesson for me around growth and learning. The most important thing isn’t necessarily the hiring funnel details, it’s about learning whatever you need to in order to become who you want to be.
In this case, I realized that I couldn’t do everything by myself. I learned how to delegate tasks and find the right people for each position.
For a business owner, hiring is the ONE SKILL you need that allows you to accomplish all of the other skills. Because when you can confidently and effectively find people for whatever roles/skills you need, the business can run smoothly and efficiently. This makes hiring the ultimate business superpower.
But for other people, learning how to communicate may be the skill that opens up all other opportunities. The key thing to remember is that you can always learn new skills to propel you to where you’re trying to go.
Many people often use not knowing something as an excuse or a barrier to their destination.
“I can’t do X because I don’t know how to do Y” isn’t a very empowering thought.
“I can do X once I learn Y. So I’m going to do everything I can to learn Y” is a mindset I aim to maintain at all times.
There is no skill that is unlearnable, but there are a lot of people who are unwilling to learn. They tell themselves “I can’t” over and over again until it is believed at a deep level.
I learned how to hire because I knew it was what I needed to do in order to get where I wanted to go. It was that simple. I had met someone who made it seem simple, and then I took action right away.
I knew I had a lot more to learn about business besides hiring. There was so much I didn’t know, but there was no textbook or online course that was teaching it. I was in uncharted terrority. So where could I look for education and guidance?
A coach? A therapist? A spiritual teacher?
No, a business mentor. Or more accurately business mentors (plural).
5. Millionaire Mentors in the Woods (Trakai, Lithuania, July 2016)
“Show up at the Vilnius Railway Station in Lithuania on Thursday July 14. And you’ll get dropped back off the following Tuesday.”
That’s all the participants were told. There was no schedule or itinerary.
It was summer 2016, and I had just traveled halfway across the world to attend a camp for entrepreneurs. I had no idea what to expect. I just hoped I wasn’t joining a pyramid scheme cult.
I had heard some vague yet eclectic stories from past participants about this event. I heard people talk about receiving valuable business lessons mixed with punisher group workouts. People spoke of freezing lake swims, huge evening bonfires and sauna dance parties. I was intrigued. Was this some sort of libertarian burning man meets business conference?
With an open mind, I rode the bus a few hours from Vilnius to a small vintage resort in Trakai in the woods. Finally, I arrived at Blacksmith Entrepreneurship and Liberty Camp.
It was at this event that exposed me to a whole other level of entrepreneurship and opened my eyes to new realms of what was possible. It shifted my mindset from “learn how to build a REAL business” to “how can I create more impact in the world?”
The mentors there were by far the most successful entrepreneurs I had met at the time. These people had built multiple eight-figure businesses, global communities, and even created the largest blueberry farm in South America!
They generously shared their time and wisdom with the participants of the camp through content sessions on team management, investing, networking, marketing and more. And they were available for 1-1 chats to answer any questions, share stories and offer advice.
This is when I realized first-hand the immense value of mentorship. I learned that you don’t have to figure things out on your own…
That there are people who have already done what you want to do that can shine a light on the path for you. You don’t have to reinvent the wheel to achieve your goals. You can greatly fast track your success by finding people who have already achieved what you are striving for who can show you the right way to do things.
Leaving my first Blacksmith camp I was a changed man. I left with a newfound understanding of what it meant to be an entrepreneur, how to be a leader and manage my teams, and I left with a deeper commitment to ‘making it count’ and living up to my potential.
So what’s the lesson here? The immeasurable value of getting good mentors.
If you don’t currently have them, find them. Identify some people you admire and reach out.
Your relationship with a mentor doesn’t have to be a formal one. It’s more about finding people who are further along than yourself that you can build a relationship with and learn from.
Mentors can be people you don’t know personally, too! Read and study books of people you want to learn from.
This is so valuable in fast tracking your success and growth. It can’t be understated.
For me, the value of these mentors that I met had a huge impact on my business and life. I was inspired now to build something even bigger! And to lean into my own growth to reach my potential as an entrepreneur.
I kept building. Getting the right people and processes in place to scale my business.
Until all my plans got thrown out the window with an unexpected phone call.
6. Selling My Business To Jerry (Shenzhen, China, March 2017)
“Hey man I have something I want to run by you..” he said.
“Ok go for it”, I responded.
I was on the phone with my business partner, Travis, walking down Mac Dinh Chi street in Saigon, Vietnam. I thought it was just going to be a typical catch up call, until he dropped a bomb that would change my life forever.
“Would you be interested in selling our business? I have a buyer who may be interested..”
“A buyer?” I asked cautiously yet hopefully.
“Yes,” he responded, “Jerry.”
I had heard of this ‘Jerry’ person before. The eccentric Chinese Mogul who was buying up all the businesses he could find. He had already bought the business of a few of my friends, including my business partner Travis.
And now he wants to buy MY business?
This was so unexpected..
I started doing napkin math in my head on what the value of our business roughly would be worth if we sold it.
Then it hit me.
My body tensed up as if struck by electricity. I could feel a ball of nervous energy building in my stomach.
Was I interested? Of course I was! Was this anything I was expecting? Hell no. As excited as I felt about the possibility, I was equally worried about messing it up.
I told Travis that YES I was interested. Which kicked off a whirlwind of events I would never have expected.
Three days later I was on a plane to China to meet Jerry. Jerry was rolling up FBA businesses (businesses that leverage the Amazon platform to sell to customers) before it was cool. And he was interested in adding our business to his already huge FBA portfolio.
I met Jerry the morning after arriving in Shenzhen. Leading up to the meeting, I could barely focus on anything. How does one prepare for the biggest business meeting of his entire life?
Jerry invited me to his office where we shared pu’er tea, chatted strategy and generally got to know each other.
He was not shy in expressing his interest in buying our business. But he did have some critical questions after our first meeting that I needed to answer if we were going to be able to proceed.
I tried to remain calm as he bombarded me with questions. “What are your last 12 months revenue and profit numbers? Profit per SKU? What are your SOPs for reorders and launching products? Would the business be able to sustain without you as the head/leader?”
Fortunately, I had built an amazing team that I could consult for all of Jerry’s questions. This would have taken me at least a week to find all the answers if I had to do it by myself, and I probably would have been so anxious in Jerry’s presence that he would have been concerned.
I frantically messaged Weena, my finance manager at the time, about the information Jerry needed. She was able to organize and deliver it for me in advance of the next day’s meeting to continue our acquisition discussion.
If I was not able to give Jerry the information he wanted it would have delayed the sale at best and killed it at worst.
On the last day that I was in China Jerry and I met again at his office in the urban sprawls outside of Shenzhen. Jerry poured us both some tea and prepared to give me his offer.
The tension in the room was palpable as we made small talk. We both knew what was coming next, but I was a rookie when it came to conversations like this while Jerry was far more experienced.
While sipping our tea, Jerry turned to face me. I could feel my insides tense up in preparation.
“I’ve decided on an offer,” he said.
All outside noise vanished as I was mesmerized with anticipation.
“$900,000”.
Immediately it felt like a balloon popped snapping me back to reality.
$900,000! This was less than the $1 million price we previously were discussing..
A bit shocked and taken aback, I felt panic rise though my chest.
What should I do? $900,000 is still a LOT of money. Does it matter that it’s not what I knew the business was worth?
At that moment I made the bold decision to tell Jerry at that price we did not accept his offer. I told him that we wanted the higher price or we’d be happy to keep the business. Jerry listened, said OK, then I left his office.
During the car ride back to my hotel the anxiety started to creep in. Did I just blow the biggest negotiation of my life?!
I wanted to jump out of the car and RUN back to Jerry and tell him that I accepted his offer! The nerves grew inside of me until I felt like I was going to explode.
In an attempt to calm myself down, I took a few deep breaths. I’d started meditation a few years prior and while my practice was still in its infancy, I put the techniques I did know to use.
A few deep breaths later and the anxiety subsided enough to think rationally about what to do now. I felt confident about my decision before delivering it to Jerry. Now the ball was in his court.
With each breath, my anxiety lowered and my head became more clear. Whether Jerry countered with a higher offer or not – I was OK. I had a great business and whether we sold it or not, I still had a great business.
I called my mentors and again received great advice.
They said that Jerry still wanted the deal and that he’d come back with a counter offer. I sincerely hoped that they were right! I could feel my stomach knotting again thinking of the possibility of losing the deal completely.
I left China the next day without a deal.
The following week was one of the wildest of my life! My emotions were riding up and down like a rollercoaster. At times feeling confident and secure that I made the right choice and didn’t sell the business for less than it’s worth.
And at other times, I felt anxiety gripping ahold of me with thoughts about how I blew the biggest deal of my career.
The next week I heard again from Jerry. He said he wanted to schedule another call. Could he be reconsidering his offer?
I didn’t want to let myself think too much about it. But time slowed to a crawl as my follow up call with Jerry approached.
My nerves were on fire, palms sweaty as I stared at my computer screen waiting for the call. The call was short. He got straight to the point.
“Hi Nate, my new offer for the business is $950,000.” he said.
I felt the tension break within me like water bursting through a dam.
Energy rushed through my veins.
And then, relief.
The tension from the previous week washed away. I could almost cry.
“Do we have a deal?”
It still was shy of the $1M price I was hoping for, but realizing what the deal meant for me in its current form I eagerly accepted the offer. I hung up the phone feeling exhilarated. The mental burden was gone, and I was filled with joy and gratitude.
After a few weeks of Due Diligence, the deal closed! My first big sale was complete. What a ride!
This taught me a valuable lesson about building with the end in mind. Whether it’s your business or other goals you want to be prepared for whatever may happen. Even if it’s unexpected.
In order to be sold, your business needs to be structured a certain way. Its finances need to be neat and clear in order to prove the valuation. It must have strong documentation in place to allow a new buyer to take over its operations, and it also must not depend on you to run.
I was not thinking the exit would be so soon but since I built my business the right way, when the opportunity came I was able to take advantage of it.
The other lesson here is to trust yourself and your decisions. Don’t second guess yourself and change your mind a hundred times. Follow what you feel is best and know that things will work out in the end.
After having my first big exit, my perspective would change in a big way. At this point, I had developed a strong passion for entrepreneurship and everything about it. I soon diversified and became involved in a number of new businesses, some as the operator and some as an investor.
My goals broadened, too. I was no longer only focused on finances and I became more interested in personal growth and development.
I expanded my usual diet of strictly business books into more personal and spiritual growth. Still loving the business books, too! But more of a balance.
It’s good that I began investing more in my personal growth because the road ahead was about to get a bit choppy. And I needed all of the tools available to me to help me overcome what was ahead.
7. Radical Responsibility (Miami, September 2019)
After selling the business, I had more money and time than ever before. Which led me to think long and hard about ‘what’s next?’. I was at another crossroads, just like I was after I graduated from college and left for South Korea. But this time I had real skills, experience and capital behind me.
I had the freedom that I desperately craved when I was 22. I was able to travel pretty much wherever I wanted and whenever I wanted to. But at this stage of my life, I didn’t feel all that accomplished. In fact, I felt hungry for bigger and better things. I felt a great sense of possibility. If I could build a business and sell it in such a short amount of time, what else could I accomplish in the business world? And who could I bring with me along the way?
I wanted to put my money and experience to work. So I got started investing and partnering in a few new ventures.
Fast forward a year or so and most of them were going well! With one glaring exception..
In the fall of 2019, one of my business ventures was a total mess. I was the operator and I had a partner/investor.
Due to circumstances out of my (or any) control the business got crushed. I had invested a lot of my own money, and my business partner did too.
As the operator, I was the one managing the day-to-day of the business. Which meant that I was closer to the situation unfolding than my partner. He knew what was going on but he was not in the weeds like I was.
He knew I was trying to find ANY option to salvage the business and both of our investments. We held out hope for the longest time until eventually, after I had exhausted all of our options I had a tough call to make.
I was sitting at the cafe in the lobby of the Conrad Hotel in Miami when it came time to call my business partner and share the unfortunate update. I had to tell him that we had to cut our losses, accept defeat and write the investments off as a loss.
As I prepared for the call, many thoughts raced through my head.
“It’s not my fault. I’ll just explain that it wasn’t my fault. I’m sorry what happened but it’s not my fault. We just have to move on even though we both are out a lot of money.”
Around the same time I was listening to the book Radical Ownership by Jocko Willink and another thought entered my mind.
“Even though it’s not my fault this business is still my responsibility. I need to do whatever I can to make this right for my investor who trusted in me.”
I knew which voice I needed to listen to.
He invested in/with me. The business got F’d. It was up to me to make it right. It was time I put on my big-boy business pants, take radical responsibility, and call my business partner.
My stomach twisted as I broke the news. I felt extremely vulnerable and had no idea how he was going to take it.
I told him that I’d pay him back every cent out of my own pocket if that is what he wanted. This was not a marginal sum by the way. We’re talking six figures.
This would have been a big hit to my personal finances, but I knew that Radical Ownership was the right approach. It wasn’t just about the money anymore. This was my career and reputation.
The more my career progressed the more I realized that it was a marathon and not a sprint. And that the best opportunities and outcomes came from trusted collaborations.
It’s about money, too. But I knew that long-term I’d have more and better opportunities by maintaining my reputation as someone who takes Radical Ownership versus someone who bails on his investors when things get rocky.
To my relief, my business partner did not accept my offer to pay him back out of pocket. He understood the situation and that we did all we could do and that the investment (and all investments) have risk.
I can’t know for sure, but I think that the reason my partner was so understanding was because I took responsibility. (In addition to my partner being an incredibly high integrity, fair and stand-up individual).
I think that if I tried to make excuses instead, it wouldn’t have gone over as well.
But because I took responsibility, even though it wasn’t my fault, I saved my relationship with my partner who remains a close friend and partner on other ventures today.
So next time something bad happens that ‘isn’t your fault’, what if you still took responsibility?
I invite you to experiment and see how it affects your mindset and your outcomes.
The more I progress in business and life the more I learn that some things are in your control and other things aren’t. Regardless, it’s up to you to deal with them.
By investing in your own personal growth, you can build a stronger set of tools to make you capable of handling whatever is in front of you. The good, the bad and the ugly. Even when it’s not your fault.
I continued down the path of personal and spiritual growth to complement and support my career growth. Little did I know, I was on the verge of a large business conflict in which I would need every tool in my toolbox to navigate.
8. Getting Dumped (Chiang Mai, November 2020)
A few years later my career shifted more to investing and advising and less operating.
I was trying to balance my time between the different businesses as well as understand my new role. Some businesses were growing better than others. Some businesses took up more of my time and energy. But I was figuring it out. Overall I was enjoying my new role and new partnerships. Things were going well! Or so I thought..
One day I got blindsided by a message from one of my business partners. This rocked my business world at the time, though ultimately it led to a great deal of personal and professional growth.
I was sitting at my kitchen table in my apartment in Chiang Mai when the words flashed across FB messenger. Instantly I felt my stomach drop, twisting into a knot and taking the air out of my chest.
My business partner just dropped an unexpected bombshell on me. I adjusted my focus and reread the text for a second time. My heart beat surging. Was this really happening?
I read through the text a third time and my mind went blank. I was stunned. I felt like I had just been emotionally tasered.
My partner was forcing me out of the business. And there was nothing I could do about it.
In his message, he told me that he had already set up a new LLC and was going to move the business to the new entity that I was not a shareholder in if I didn’t agree to his (lowball) buyout terms. My only option was to accept.
It’s wild how fast things can change. Just the day before we were catching up on a call, same as we did every week or so over the previous two years. I felt good about our call. Like I usually did.
The following day we were messaging and had a disagreement which soon got emotional. This had NEVER happened before, so I was caught completely by surprise when he told me that our partnership was over.
I felt cheated.
I felt hurt.
I felt betrayed.
I probably could have gotten a lawyer, but the amount of money in question isn’t worth the hassle and expense. So I was left bathing in my emotional discomfort.
I tried to brush it off, but for the next few days I’d catch myself thinking about what transpired more than I cared to. Okay, it was basically driving me nuts. Normally my mind is pretty calm, but this shit was fucking with me.
Later that week, I popped in an Anthony De Mello audiobook on one of my afternoon bike rides. He explained a new frame that totally changed how I felt about the situation.
In the book, De Mello asks the reader to imagine that you have a magic eraser that could erase any experience from your history. Totally and completely.
This magical eraser would also erase everything that happened as a result of that experience, wiping the experience and its effects on your life forever.
So De Mello asks, if you had such an eraser, would you use it?
This got me thinking about my frustrating experience with my former business partner as well as everything that happened as a result of it.
Yes, it was frustrating, but it also led to a lot of growth and positive change in my life that I hadn’t realized until then.
Being out of this business had opened up time for me to engage more closely with another business. This other business was bigger, more exciting and more aligned with my unique strengths.
This break up also led me to take an objective look at my time and allocate my attention to better opportunities.
This business had been generating the least amount of income and also was taking up the most of my energy. It was the furthest away from the revenue targets and not generally related to the other things I was focusing on.
So, not being involved in this business allowed me to double down on things that were working better.
Once I was able to see things objectively, I realized that I had been so lost in my own frustration that I was unable to see the positive things that had happened as a result of this “so-called” business catastrophe.
This experience also became a catalyst for better communication with my other business partners, as I made it a point to check in more often on my relationships and ask deeper questions so I knew where they were really at.
So, back to De Mello’s question, I wondered if I’d use that magic eraser to erase our disagreement to ‘go back to the way things were’.
Then it hit me. I realized that I would NOT use that eraser to change what happened. The growth had outweighed the struggle.
And if I wouldn’t change it, even if I could, that means that I would still choose it.
Realizing that I would actually choose this experience completely shifted my feelings about what had happened.
It still felt frustrating at times, but after recognizing the growth that has happened as a result, I knew that I was living in the best possible reality.
Once I dropped the victim energy, I knew that this didn’t happen to me, it happened for me. This shift in perspective gave meaning to the experience, which helped me get over the frustration and back to my peaceful mind.
The biggest lesson from this experience is that no matter what you’re going to encounter rough patches.
While you can’t control when life throws you a curveball, you can control how you react to it. That’s the power of mindfulness and personal development.
It gives you the tools to manage whatever situations you find yourself in.
It’s impossible to know at the time if something is good or bad for you because you never know what will happen in the future. The dots only connect looking back. So don’t dwell on life’s misfortunes. Do what you need to do, and then move on to bigger and better things.
Having more space from this business also gave me more time to reflect on my strengths and where I was focusing my energy. I wasn’t wasting my time on projects I didn’t care about, but I had lost some passion. Something felt off, but I wasn’t sure what it was.
Soon I would figure out what was out of alignment. And the timing was what some people may call “divine”.
9. The Truth About Finding Your Purpose (Koh Phangan, Thailand, Spring 2021)
My business breakup led me to take a more critical look at my life and career.
What’s going well? What isn’t? Is this the best path for me?
By clearing some things off of my plate it opened up room for more reflection and analysis. This led me to the next level of business and personal insight that catapulted my understanding of myself, career, purpose, and mission.
The longer you’re in the entrepreneurship game the more your priorities and perspectives change. After achieving your basic financial needs, you graduate to new needs like fulfillment, impact, and achieving your potential. Often the shift doesn’t happen gradually, but quite suddenly. Like it did for me.
During a time of intentional reflection I woke up to a truth that is now so obvious I can’t believe I didn’t see it sooner.
I was down on the Thai island of Koh Phangan for a week of reflection and fun. As a part of my usual routine for quarterly reflection, I was filling my mind with growth oriented content and perspectives so I could evaluate myself and my life.
I happened to pop on Seth Godin’s book The Practice. Quickly I became obsessed. I listened to the book five times during that week in an attempt to memorize and internalize its amazing and powerful lessons.
One of the truths that resonated with me was that we are all artists and that our greatest opportunity in life is to create value with our art/craft. The way we create value with our craft is by solving problems for other people. The bigger problems we solve for other people, the more value we create in this world. And the more value we create for others, the more value we receive for ourselves.
Godin shares that the way we can create the most value for others is by doubling down on our strengths and our superpowers. Then, commit to leveraging them and continuing to hone them so we can have the biggest impact.
This wasn’t the first time that I encountered these Truths. But they hit me this time in a way like never before, radically changing my own self perception and understanding of my mission in this world.
Seth Godin encourages us to think about our greatest superpowers and where/who they can be directed to solve the biggest problems. This really got me thinking..
What ARE my greatest strengths?
WHO can my strengths solve the biggest problems for?
Upon reflection I realized that I was not building my career around leveraging my greatest strengths in service of the people I can solve the biggest problems for. I was busy focusing my efforts on solving business problems that, simply put, weren’t the biggest problems.
I realized that my greatest strengths in business were building amazing teams by getting the right people in the right places. On top of that, I knew I was exceptional at keeping the A-Team on track by instilling a high performance culture, identifying and focusing on the high-level vision and setting priorities accordingly.
After gaining more clarity on my strengths, the next question was who do my greatest strengths solve the biggest problems for?
Well, if my greatest strengths were solving “people problems” as well as solving problems with people, then I could solve the biggest problems for businesses that rely on people. Duh!
This realization hit me like a ton of bricks and catalyzed a shift that totally transformed my career.
It became clear to me that I had been putting my strengths to use, but not in the most effective way.
Basically, after exiting my ecom business I continued in the ecom space and working with and supporting other ecom businesses. While ecom businesses do need good people, their biggest problems are typically sales and marketing. These are areas I’m good at, but not my real zone of genius.
Looking back on the last few years prior, I realized that when I spoke about solving ‘people problems’ in front of ecom businesses vs service businesses the reactions were dramatically different. The ecom business audience would get lukewarm interest at best. But the service businesses would be jumping at the opportunity to work with me and expressed frenzied interest in my help!
I now recognized the clues and omens that were pointing me in the direction that I needed to go.
With this new realization I was able to commit even more to focusing on my strengths and solving the biggest problems for other entrepreneurs.
So what did that mean for me?
Shifting my focus to advising and partnering with other service-based businesses. To leverage my superpowers of remote team building to unlock growth for the businesses and happiness for the founders.
This was a big leap for me! It was scary to shift my focus after years of pursuing a different direction. Andrew’s words rang through my head again pushing me to ‘just do it’ and make the leap.
It wasn’t long before I found some new exciting partnerships with businesses that I knew I could really help. A few months later and the new advisory and partnerships were working out great! The businesses were all growing. The founders were working less and making more. And I enjoyed my advisory role immensely.
I had niched down to work more with service businesses. But the real key point was getting clarity around ‘my lane’ and committing to staying in it.
Life is a long journey. And we have the best journey when we double down on our strengths solving the biggest problems in service of people we care about. Capital ‘T’ Truth.
When you orient your life around this you can’t go wrong. Set your north star to ‘leverage my strengths to solve problems for people I care about’ and you’re on a course for success.
I also realized here that receiving clarity and alignment is not a one-time event. You don’t all the sudden get clarity and then you are done forever.
No, the way you get clarity and maintain alignment is by continuing to reflect and look at your situation! Assess what’s working and what isn’t. Reflect on what you want to change and what you want to double down on.
It turns out that this sort of reflective work is the most important work you can do! Because it sets your trajectory for the future.
So what’s the best way to maintain your alignment and clarity?
By committing to a practice of reflection and re-calibration. Which is what I did.
10. Strategic Sabbaticals (New Orleans, Fall 2021)
For entrepreneurs, work and life can be a tricky balance. Because we are often so passionate about and excited by our work, we never take any real breaks.
This was me for years.
Yes, I still had a good ‘work-life balance’ meaning I wasn’t working 100 hours a week and had time for activities I enjoyed. But the reality was that I NEVER took any days totally off.
One of the mentors that has most impacted my entrepreneurial journey is Dan Sullivan. He’s the author of countless books as well as founder of the Strategic Coach coaching program.
He advocates for a concept he calls ‘Free Days’. The basic idea is that entrepreneurs, like professional athletes, need days totally OFF. To rest and recharge. So that we can perform at our highest when we are ‘on’.
For so many years I lived and ran my businesses on my own schedule. This didn’t include a respect for weekends. If it was Saturday and I felt inspired I’d hit the cafe for a few hours. Have a project I’m working hard on? Sunday can be a great day for catching up on things and getting a jump on the week.
Often I’d only work a little bit. Check emails for an hour. Respond to some messages on Slack.
But what I didn’t realize was how even this slight work was slowly burning out my reserves. Your work brain needs time to rest just like your body! Which is why it’s categorically different taking a day 100% off verses working for a short amount of time.
Over the years I began experimenting with this idea. First, committing to taking Sundays as Free Days while I was living in Bali. I followed a strict Sunday schedule of yoga, ecstatic dance, biking and evening sauna. Leaving no room for any work.
At first this was really challenging! I was anxious about not checking in on email and Slack the whole day. But with practice I was able to relax and enjoy my day without any thoughts of work.
I continued to push this Free Day practice from one day up to a full week! Until I leaned into taking a full week off at the end of each quarter. The weeks off at the end of the quarter became an important ritual for my work and happiness.
So what did I do during my quarterly weeks off?
No emails. No Slack. No calls. A full week dedicated to reflection, planning and play.
I began doing this so I could reassess, realign and ensure that I was on my highest path. Heck, sometimes people need to do this to ensure that they’re on their own path and not someone else’s!
This became an opportunity for me to ponder important questions such as:
What’s going right? What’s not going as planned?
What do I want to do more of? Less of?
How can I have an even bigger impact?
I also found it beneficial to fill my brain with positive and inspiring content during this weeklong retreat. Doing this helps to remind me about what’s important..
Some of my favorites are: The 15 Commitments of Conscious Leadership, The Way of the Superior Man, The Practice and The Bhagavad Gita. But it changes each time I do this.
In addition to the content and reflecting, I filled my days with as much flow and play as possible.
For me, it included a lot of one of my favorite forms of play – exercise. As well as exploring altered states of consciousness for fun and insights.
What sort of results happen during the quarterly weeks off?
A deeper clarity and connection to my mission/purpose. Inspiration on how to have a bigger impact. A complete refilling of my tank to ready myself to get back to work.
It’s an opportunity to rest up like Dan Sullivan advocates so I can perform at my highest when I’m ready to get back in the game.
Life is a marathon, not a sprint. Which is why it’s so important to both give yourself breaks and give yourself time to recalibrate. Taking time off each quarter to reflect and plan gives you both.
This is not a new concept at all, but it becomes more and more necessary as our society becomes more and more chaotic and addicted to stimulation.
It’s been one of the most impactful practices I’ve done and I urge you to try it! I know it may sound scary. What would happen to your business if you disappeared for a full week? What may happen to you when you get off the hamster wheel of busyness and routine?
Even if you can’t pull it off now it becomes a goal to strive for. Start with a day or even a weekend. Give yourself the gift of slowing down without obligations and distractions.
When you give yourself the proper space, you will open yourself up to greater levels of inspiration.
Because the journey of life never stops. But if YOU never stop, then you might miss out on your next level of excitement.
Conclusion: It’s ALL The Journey
It’s a cloudy Monday towards the end of 2021. I’m sitting at my desk in Austin, Texas working to put the final edits on this piece, which feels like a behemoth.
I have nothing on my schedule today except for a 2:30 PM yoga class. One of my smaller businesses went up for sale today on Empire Flippers, but I’m not extremely excited nor nervous. My main task of the day is to write a conclusion to this piece, and to be honest, I have no idea how to do that. This is the longest piece I’ve ever written, and despite having a call with my editor this morning, I’m still not sure how to end it.
In the last ten years, I’ve achieved some success, but I have some friends that still make me feel like I’m barely accomplished.
I still go through ups and downs, just like everyone else. While my portfolio is doing well, I still often compare myself to my friends who have more cash flow coming in than me.
Looking back on the past 10 years, it’s been one helluva journey. But it’s far from finished. I am not certain there is an end at all.
One thing I do know for certain is that no matter what, life is going to keep happening. The good and bad, the ups and the downs. So what’s the point?
The point is to enjoy the journey! I mean, what else is there? Every wave crashes. Every vacation ends. It’s ALL the journey.
I know it might sound cliché, but maybe that’s because it’s actually true.
There is no ‘getting there’. There is just where you are and how you feel every single day.
So you might as well enjoy it! For me, the ultimate success is enjoying life as much as you can while creating value for others you care about.
If you’ve read this far, then I thank you. But before I finish, I’d like to reiterate these ten incredibly valuable lessons that I’ve highlighted in this piece. My ultimate hope is that you, the reader, are able to take these great lessons and put them into practice in your life and business.
10 Lessons From 10 Years Of Entrepreneurship In A Nutshell (TLDR)
When you are called to pursue something, ‘just do it’ like Andrew advised. Take that leap. Jump. You’ll build your wings on the way down.
Know that things aren’t always going to be easy. You’re going to encounter hard times. In those instances, remember what Max said to me and push through. Stay committed to your course to reach the success you are striving for. Even if it’s not pretty or glamorous.
Remember that you don’t have to do it alone! Find your tribe like I did in Bangkok. They’ll be there to support you through the hard times and help you celebrate your wins.
Know that wherever you are headed, there are people out there who can and want to help you get there. Seek out these mentors that have done what you are aiming to do and learn from them. It’ll greatly fast track your success.
Build with the end in mind and work backwards from your goals! Be open to miracles. Prepare for success. That way when you encounter an unexpected opportunity you’ll be able to take advantage like I was able to do when Jerry wanted to buy my business.
In times of uncertainty and adversity, take radical responsibility for what happens to you. Don’t blame or play victim. No matter what. Choose to look at things as happening FOR you not TO you. This shift is so powerful.
Still, some things will happen that are out of your control and that will blindside you. But your mindset and how you react to what happens is in your control. So invest in strengthening your inner game so you can flourish no matter what.
Be intentional about your life and work. Do the things you enjoy. Double down on your strengths and solve problems for others and you’ll be on the right track.
Last but not least, enjoy it. Life and business is meant to be enjoyed! So lean into your free days. Start with one and build up to a full week. Shake things up and see what happens. Take space from your routines and allow transformation.
I didn’t say it was easy. But we are all on this journey and time is going to pass anyway so it might as well pass while we are improving ourselves and our lives.
I sincerely hope that this reflection on my first 10 years as an entrepreneur helps lead you to more success and fulfillment in your career.
If you enjoyed this please reach out and let me know! I love connecting with like-minded entrepreneurs who share my values.
As for me, I don‘t know what the next 10 years will bring. But I know if I keep building on the principles and lessons I’ve learned in my first 10 years then I’ll be on the right track.
To a lifetime of happiness,fulfillment, and continuous growth,
Nate Ginsburg