4 Entrepreneurial Fears And How To Crush Them

Sharing a laugh with NBA official Kenny Mauer (also a  sports entrepreneur !) at a recent Ultimate Hoops event in New York


  • Educational background is not linked to business success

  • Focus on product, everything else comes second

  • Use healthy self-delusionment as your inner fuel to push past fear  

  • Regret of not starting your business may last a lifetime

Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do, so throw off the bowlines, sail away from safe harbor, catch the trade winds in your sails. Explore, Dream, Discover.
— Mark Twain

Imagine spending weeks on a business plan for your dream sports business venture. You are enjoying sleepless nights because your idea flushes untapped adrenaline into your system. What an amazing feeling!

Now the scary part: sharing your idea with the world. Sadly, millions of brilliant business plans stay tucked away in the basement of people's minds because of one reason.


I'm here to tell you fear is just part of the process. So take a deep breathe and embrace it. Fear is the fuel entrepreneur engines run on! 

Here is a list of 4 fears a first-time entrepreneur faces and how to move past them.


1. I don't know anything about business

This was a big fear of mine. I was a Liberal Arts major in college. I didn't take one business class. Not one! But I had three characteristics which served me well: an insatiable curiosity for business, 10 years of corporate experience and the absolute belief my idea, Ultimate Hoops, would find its place in the recreational sports market. 

The most important element in your idea is to determine if there is market demand for it. Period. Everything else can be supplemented through research and deep self-awareness of who, or what tools, can cover your inexperience in unfamiliar steps of starting a business.

Understand you WILL make many mistakes. (Trust me, I made a ton of them and every one was a valuable lesson.)

Focus on your product. Everything else comes second.


2. I won't have any customers

Congratulate yourself for making it this far in the process: you're ready to open for business! This stage requires you to trust your instincts and believe in your product or service. When you flip the 'We're Open" sign on, you must instantly transform into your "happiest customer." If consumers simply see you as a faceless name behind the curtain and not a passionate participant, you're authenticity will sink. If this is a product you've always dreamed of, this shouldn't be a problem.

Channel your enthusiasm in your marketing. How I wish Instagram Stories was available when we launched Ultimate Hoops. I would have documented every part of the pre-launch stage. The development of the website, the search for gym space, our first team registration!

Consumers love getting access to "behind the scenes" of their favorite brands. Show everything, warts and all! The warts are what endears you to customers. Then ask for feedback. This will give you an indicator of how many customers are interested in your business before it goes to market.

If consumers are engaged in your content, they'll share it. If what you're offering is truly a differentiated experience, customers will find you.


3. I'll be labeled as flaky and irresponsible

I had an established career as a marketing executive in New York City. I left it all behind to start a basketball company in Minneapolis. I went from having a comfortable six-figure salary to no salary at all! Oh, the shame I felt from my friends and family when I told them of my plan. 

Did it stop me? No. I knew I had no choice. I was intoxicated with my business plan and nothing and nobody was going to stop me. Even my own insecurity.

You need a healthy dose of self-delusionment as an entrepreneur. You need to envision your business' success in all its future glory, often on a minute-by-minute basis. It's the air you need in the grind of launching a new business. It's your oxygen mask. 

Understand if your idea does not burn hot enough inside of you to block out your doubters, including your own self-doubt, you shouldn't start. You have to believe in your business with all the conviction in the world. 


4. If my business fails, I will regret it for the rest of my life

Regret is in the eye of the beholder. Don't believe me? Here is a simple truth: studies show people regret what they didn’t do or didn’t say more than they regret what they did do or did say.  

Why? Because humans are driven by fear.

So what does this mean for you? It means you have no choice but to start your business venture! Do you want your ideas, your dreams, your life to go unfulfilled? If you're feeling consumed by your idea 24/7 like I was, it feels bigger than just an obsession...it feels like a higher calling***!

Go out and get started or you will always wonder...what if? No amount of money you accumulate through your "safe" career choices will pay for the regret you will carry with you for the rest of your life.

*** My father, at 58-years-old, passed away unexpectedly in 2001. He was an avid sports fan who cherished basketball, especially the NBA and his homestate team, the Minnesota Timberwolves. Founding Ultimate Hoops was partly to honor his legacy and leave a small basketball footprint in the world for him.