Alex Simon

“Everyone has a plan until they get punched in the mouth.” – Mike Tyson


Alex Simon is the CEO and Founder of Digital 86.

The firm was founded by Simon, a longtime public relations executive.

Simon is also known as The Digital Fixer™. Often referred to by the media as “a master shaper of online reputations”, he has made a career out of promoting and protecting high profile artists, entertainers and executives.

Simon got his career started in 1999 as a publicist for professional fighters. It was during that time that he mastered crisis management by dealing with athletes who often found themselves in trouble with the law.

“Today’s online world is like the Wild West. Anyone can roll into your town and trigger chaos – warranted or not. Angry customers, jealous competitors, vengeful exes, an old DUI from your college days, and on and on. People come to me when they need swift and decisive action to make sure they are portrayed fairly and positively online”, says Simon.

Where did the idea for Digital 86 come from?

I started by doing public relations work for professional fighters in 1999 and most of my work was crisis management. As the company evolved, we started doing more online work, which led to me starting Digital 86.

What does your typical day look like and how do you make it productive?

I get up around 7 and train for my triathlon races (swim, bike and run). Once at the office, I first check on any crisis that happened overnight, followed by a team meeting. The day goes on from there, ending around 9pm.

How do you bring ideas to life?

I’m very much attentive to trends, and jump on something if I feel it’s worth exploring as business idea. Shoot first, aim second.

What’s one trend that excites you?

AI (artificial intelligence) is going to be huge!

What is one habit of yours that makes you more productive as an entrepreneur?

Exercising. It calms the mind and gives me the energy I need.

What advice would you give your younger self?

Be prepared for “peaks and valleys”. Entrepreneurial life is just that. Whatever stage you’re in, it’ll eventually change.

Tell us something that’s true that almost nobody agrees with you on.

It is possible to manipulate Google search results.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Use a to-do list. It keeps you on track and you don’t need to remember much.

What is one strategy that has helped you grow your business?

Going for things without much preparation. We learn as we go and adjust accordingly.

What is one failure you had as an entrepreneur, and how did you overcome it?

Not saving enough for a “rainy day”. 2008 took a toll on my fast-growing business. I’ve rebuilt my firm, but it took several years. As they say: “I did not see that coming!”.

What is one business idea that you’re willing to give away to our readers?

Buying and selling vintage VW buses. I collect them and their prices are skyrocketing in value.

What is the best $100 you recently spent? What and why?

It was actually $8.00 on my self-made website for Digital 86. It has given me millions in ROI.

What is one piece of software or a web service that helps you be productive? How do you use it?

NordVPN. It allows me to do my business in private, without fear.

What is the one book that you recommend our community should read and why?

48 Laws Of Power by Robert Greene. It’s all you need to know to be a person who knows how to world really works.

What is your favorite quote?

“Everyone has a plan until they get punched in the mouth” – Mike Tyson

Key learnings:

  • Pursue ideas even if they aren’t fully fleshed-out.
  • Entrepreneurs have good times and bad times. Prepare accordingly.
  • Your reputation is worth gold. Protect it at all costs.