3 Business Lessons That the Worst Year of My Life Taught Me

Going 'all in' on cryptocurrency as a business was a huge mistake, this contributor now acknowledges.
3 Business Lessons That the Worst Year of My Life Taught Me
Image credit: AleksandarGeorgiev | Getty Images
Guest Writer
Co-founder of Tailored Ink
6 min read
Opinions expressed by Entrepreneur contributors are their own.

For three years, from 2015 through the start of 2018, life was really good. In fact, that long stretch was probably the happiest time of my life.

Related: How I Transformed My Business Failures Into Strengths

Yes, I had been fired from my last full-time job, but I found a great girlfriend. Yes, I felt support enough to start my own agency with a fantastic business partner. And, yes, that business, Tailored Ink, grew by leaps and bounds. I started making six figures working with brands I'd never dreamed we’d land. I was invited to join the Young Entrepreneur Council.

Honestly, life was almost perfect. Until it wasn't.

Peaks and troughs...

That third year, 2018, started as good as the previous two years had been. We entered the emerging crypto/blockchain niche and were one of the only above-board creative agencies in the space. And, in no time at all, we attracted a lot of quality projects and became advisors to several blockchain startups. Our pipeline was bursting.

Just before that time, during Q4'17, I liquidated my retirement accounts and invested all my savings into cryptocurrencies. By January 2018, my portfolio had ballooned 500 percent -- in just three months.

But, then ... everything went south. Not only did I lose half a million dollars, but I also watched the crypto markets crash, in an endless bear market that lasted the entire year. This, of course, affected nearly all of the projects we were working on at the time.

At least I learned some things. Here are those three lessons from the worst year of my professional life:

1. Pride makes you greedy, and greed leads to mistakes.

Most men are risk-takers. This makes us, on average, terrible traders and investors. Unsurprisingly, women are far better investors because they’re more risk-averse.

For example, because I had correctly predicted the crypto boom in Q4 2018, I felt like a genius. It was the easiest money I’d ever made. So, I got greedy.

When the crypto market finally crashed, I figured that even that was just a minor hiccup. Surely bigger gains would come in the months ahead. I barely paid attention to the markets, hodling (crypto slang for holding currency) for the long term. By the time I realized what was happening, it was already too late.

In retrospect, I can’t believe that I nearly blew up my account. Stories of the Market Wizards (i.e., top traders) doing the same thing in their early trading days, however, made me feel slightly better, and also led to a revelation: Being successful in one field doesn’t mean you’ll be successful in others.

Aside from one's work ethic, most money manager success stories boil down to the same set of skills: being able to see opportunities and take them, and being able to cut your losses when you’re wrong.

Related: Why Embracing Failure Is Good for Business

Because I hadn’t been wrong for a long time, I couldn’t recognize that I was totally wrong -- until it was too late. My pride got the best of me.

2. Burnout is real, and the best medicine is time off.

After losing all that money, I felt depressed. Duh. Not only was I completely floored, but I also couldn’t stop thinking about what I’d done. Half a million dollars, gone forever!

And the damage didn't end there, because the crypto markets kept shedding value month after month. Our security token offering (STO) projects were some of the best. But because of broader market conditions, investors got scared off. It became difficult to market and raise money.

Around this time, I was working 60 to 80 hour weeks, trying to do anything I could to help my clients. At one point, my business partner and I worked 30 hours straight without sleeping, pausing just for bathroom breaks and food.

This was when I found out that my girlfriend of four years had been compulsively lying to me about all sorts of things since our first date. I broke up with her, but was heartbroken and in shock.

Needless to say, the burnout I experienced was real. By the end of the year, I was ready to take a break. And I did, going on a month-long vacation, which I hadn’t done since college. That time off allowed me to take a step back and reflect on everything that had happened.

In retrospect, I knew I was burning out months in advance but did nothing  because I was trying to earn back all the money I’d lost. What I didn’t take into account was that I’m only human.

3. Work-life balance is essential for happiness and productivity.

It’s crazy how quickly success can make you forget just how little you actually know, especially when you’re young. I turned 30 not too long ago, and I feel that every single year of my 20s was an incredible learning experience, especially last year, when the knowledge I acquired was so vital.

In a word: Even though I lost half a million dollars, I know I can make it back. And this time, I’ll be much more careful about my investments.

And even though Tailored Ink entered a volatile market at literally the worst time possible, there was no way we could have known. The real mistake was pivoting our entire business toward crypto and blockchain projects in the first place. That was a risk we didn’t have to take.

Going forward, we’ve learned that growing a business isn’t all about grabbing at shiny objects and scaling as fast as possible. It’s not just about working 80-hour weeks and making as much money as humanly possible while ignoring friends, family and other loved ones.

We’ve already pivoted back to what we used to do, and we’ve got plenty of leads in the pipeline again. We even hired a great COO to help us rebuild. In 2019 and beyond, we’re going to try to figure out a better work-life balance.

When life gives you lemons…

Maybe you’re in your 50s and have taken more than your fair share of licks already. Or maybe you’re 21 and fresh out of college, an unblemished entrepreneur in the making.

Related: How 10 Billionaires Faced Failure (Infographic)

Whoever you are or however successful you might be, remember that it’s not humanly possible to always win. Getting knocked down is a normal, expected part of life -- especially for an entrepreneur.

It’s how you deal with failure and get back up that counts.

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