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How to Overcome Any Entrepreneurial Challenge as a Founder

Challenges are part of the gig when you’re an entrepreneur. Here’s how to overcome the hardest ones

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BY Bill Green - 30 Jan 2019

overcome challenges as a founder

PHOTO CREDIT: Getty Images

The moment you decide you want to become an entrepreneur, is the moment you sign yourself up for a life of troubleshooting.

When it comes to going your own way in life--whether that means building a small business, or swinging for the fences and aiming to build a global company--you must be prepared for all the hardships that come with that freedom. The idea of becoming an entrepreneur (or worse, someone's "boss") might sound like a ton of fun, but the truth is, it's a journey of never-ending obstacles.

The best entrepreneurs either know this "brutal truth" going into it, or learn it the hard way and adjust their mentality accordingly. They transition from being someone who looks to avoid difficult roads, to a leader who embraces them--and beyond that, sees "Do Not Enter" signs as opportunities for exploration and improvement.

After all, entrepreneurship is all about reinvention. Trust me, what works today, won't necessarily work tomorrow. That's what makes the game so fun (and, at times, frustrating).

Here are four keys to overcoming any challenge that presents itself on your path:

1. Know your business inside and out.

Don't be a clean-desk CEO.

What I mean by that is, if you're in it to win it, then prove it by doing your homework. Know your game better than anyone else.

I tell this story in my book, All In, but back when I was building my first business, Wilmar, I became a total geek when it came to knowing our products inside and out--and that included plumbing supplies. Some people in my position would have opted to pass these duties on to someone else, but I never wanted to get caught off guard. I wanted to know everything about the products we were selling.

Let me tell you why that was such an important decision: because it mattered to my stakeholders, my customers, and my employees. It was proof I wasn't some clean-desk guy who didn't want to get his hands dirty. My knowledge of the business provide I was invested one-hundred percent, from top to bottom--and that sort of attention to detail is the culture I've strived to build in all of my companies.

2. Adapt endlessly to keep your business alive.

I'm telling you now, there are going to be times in your entrepreneurial career when you'll be faced with a fork in the road.

I have always seen these moments as pivotal. Sometimes, you will expand in big jumps, like adapting your business from retail to commercial offerings. And other times, you will have to make a series of smaller, more strategic moves in order to keep moving forward. What's most important is that, as the founder, you continue to have a healthy vision for what it is you want in the long run.

Keep your eyes on the prize.

3. Embrace technology as much as you can.

There's no pride in doing things "the good old fashioned way." Not when it comes to operating your business.

Hug your laptop, kiss your smartphone, and thank your lucky stars you're living in the 21st century. With these devices, you can conquer worlds from your own home. If you go into business and fail because you didn't invest in the best technology you could get your hands on, then I don't know what to tell you. You went to war with a water pistol, and you got soaked.

Technology rules today's marketplace.

I remember the first time my company, Wilmar, went digital. This was 1992, and the Internet was still incubating. I remember envisioning our customers being able to go on a computer in their office and put their own orders into our system. So, I found a good deal on a Wyse WY50 terminal, and bought ten for some of my customers. Then I stopped by their offices and installed them--for free. They weren't even our ten biggest clients. They were just ones I knew had dial-up modems and would bring us more business if they could place orders this way.

It worked. Those ten customers loved it, and were even more loyal after I empowered them with this new technology.

Looking back, that early decision was one of the first steps we took to differentiating ourselves from our competitors.

4. Be both persistent and consistent.

One of the great cliches in business is to be persistent.

But I believe persistence is the result of a much simpler habit--the habit of consistency. In order to have the patience and the wherewithal to make it through tough times, you have to be accumulated to dealing with failure. And the only way to get accustomed to dealing with something difficult is to do it over and over again.

The best entrepreneurs are consistent, sometimes to a fault. They spend years refining their daily routines. They constantly optimize their lives for the results they're looking for. And in some cases their obsession with consistency is what keeps them from making an unconventional (but necessary) pivot in order to stay relevant over the long term.

The key to consistency is to show up, day in and day out. The more experience you get under your belt, the more you will begin to make decisions out of habit--and the more naturally you'll be able to deal with the everyday obstacles of entrepreneurship.

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