I’ve been doing startups for 22 years, but it took me the first five or six to appreciate how difficult it is to build, grow and sustain a business. Like most people, I saw challenges as something bad and sought to avoid them, but some were unavoidable — the 1999 internet bubble, for example, or the 9/11 attacks and subsequent freeze on media spending.
Only after we overcome struggles does it become clear that success can come as a direct result. In fact, dealing with obstacles of varying degrees and urgency is a requirement to succeed in both life and business. Once you get through enough, you realize that even the worst-case scenario can have a positive solution. It may have taken me a few years to understand, but now, I see obstacles as opportunities, and without them, I wouldn’t be where I am today
Embrace the challenges
Attempting to do anything hard comes with challenges, so embrace them. If we look at obstacles as opportunities to turn problems into progress, we increase our chances of success. Confronting obstacles forces you to assess the situation with new eyes and innovate creative solutions. You end up wiser with new skills and experiences. Challenges force us to access our full potential.
In 2016, a partnership with Facebook was making us $3 million a month. They encouraged us to experiment, but one of our biggest ideas needed more data than they were willing to share, so we shelved it. A few months later, when Facebook changed its policies and all that income came to a screeching halt, my mind went back to that abandoned idea. It took several years to build the relationships with app developers ourselves, but now, the product we launched has made us $50 million this year, all because Facebook forced us to try to take the project into our own hands.
Change your perspective
Instead of avoiding them, view obstacles as opportunities to improve. Panic and fear in the face of struggle can feel normal. Fail once, and you can easily fall into the trap of believing you’ll always fail. There were times I wasn’t taking pay, and some of my employees weren’t either. It would have been so easy to lose my mind in the fear of worst-case scenarios. So, I changed my perspective from helplessness in the face of a challenge to learned industriousness through overcoming them.
When you can separate the thoughts that cause fear from those creating solutions, you have greater control over handling problems. I’ve freaked out on people who needed to pay late, but this does nothing to get anyone to pay sooner. As long as my only solution was to complain about how helpless I was, I lived in a monthly cycle of fear that someone might not pay. Once I took an industrious perspective, I saw this challenge as an opportunity to take greater control of my business.
Take action, take control
In 2018, one of our largest advertisers, already late with their payment, called to ask for another month. At the time, we were barely profitable. Our monthly ad bills were due up front, but we collected money from our partners at the end of the month, and cash-flow problems were stunting our growth. I knew the money would come in eventually, but I panicked, imagining myself without enough to make the upcoming payroll — it was a wake-up call.
I knew only a long-term solution to our cash-flow problems would stop this same situation from continuously coming up, so I took action. I wrote to our partners with the idea that our business would grow faster if they pre-paid their invoices, leading to more traffic for them — a win-win. Impending doom forced me to ask something crazy, but surprisingly, they said yes. Ever since, we’ve averaged 250% annual growth, all because one partner didn’t pay on time.
Be humble and transparent
When you nurture transparent and honest relationships, you end up with more people willing to help you when you need it. It can be hard to admit when times are tough, but if you try to make the situation not seem as bad as it is, people are much less likely to step up and help. A lot of uncomfortable conversations come with challenges, so dig into that feeling when you sense it and overcome that emotional stress by talking it out as soon as possible. The more you do it, the more confident you become.
Share everything — not just once a problem occurs but always. This way, you have people who know your thought process and understand enough about you not to lose faith in you or the business when something goes wrong. At one point, we were millions of dollars in debt, so I laid out a plan, explaining to everyone who I could pay and when so they knew I was taking ownership of the problem rather than hiding from it. It was less than ideal, but being honest about the struggle and humble enough to ask for help got us through those hard times and, eventually, out of debt.
The first challenge you overcome is the most important because it’s the one you’re least prepared to handle, but each time you take one on, you come out more capable of handling anything. Give yourself the mental fortitude it takes to struggle through it because, number one, it’s possible, and number two, after you do it once, it becomes easier. Once you’ve overcome enough, you learn that turning obstacles into greater opportunities always leads to success.
