What Every Entrepreneur Needs


Elon Musk describes life as an entrepreneur as being “like eating glass and staring into the abyss of death.” It can be painful, lonely and depressing. Discouragement is a frequent visitor to the often worn out entrepreneur. Though many entrepreneurs may be extremely gifted, they still need help. The self made entrepreneur is a myth. Dig deep enough and you will find people that encouraged the person at many points along their journey. I hope to convince you to find a way to encourage an entrepreneur today.

4 things you might not know about entrepreneurs

1. Entrepreneurs are often lonely.

The entrepreneur sees the world differently and is always thinking of new ways to solve problems. The entrepreneur is often very different from his or her peers. This naturally tends to lead them down a lonely path especially when the problems that the entrepreneur is attempting to solve aren’t seen or recognized by those around them.

2. Entrepreneurs are often worn out.

In the quest to solve the worlds problems in unique ways, the entrepreneur is often blazing their own trail, one that often has not been gone down before. This can be an extraordinarily exhausting. Couple that with wearing most of the hats of the new business and you often end up with a worn out entrepreneur.

3. Entrepreneurs are not invincible.

Many people see the entrepreneurs unique gift set and often subconsciously conclude that they are a person that needs no help.  This simply is not true. No matter what perception they give off, entrepreneurs are just unique individuals beset with roughly the same needs as everyone else.

4. Entrepreneurs are often much closer to success than they realize.

It’s easy for those starting a business to get burned out because of the long hours, the hardships and the setbacks. If this goes on for long enough, the temptation to quit is often overwhelming. I gave up on countless ventures when I was younger, many of which I believe could have been a success had I been encouraged to stick it out. That’s hard to do without encouragement.

4 simple ways to encourage an entrepreneur

1. Give them an opportunity to fail

Look very closely into an entrepreneur’s past and you will find people, often times family and friends that gave them opportunities to fail. They communicated their support whether a project was a success or a failure. They loaned them money knowing good and well they may never see it again. They purchased their first poorly made products they were selling. Both Steve Jobs and Jeff Bezos had families that gave them opportunities to fail. I think one of the greatest tragedies of our culture is our great fear of failure, which has led many people to never take risks. Many gifts are wasted in this world because the person never had a healthy atmosphere where they could fail.

2. Listen to them

Much of an entrepreneur’s life is spent inside their own head. It’s where they wrestle with ideas, face challenges and try to solve the world’s problems. There’s also much debate and second guessing of decisions that goes on in that head. Many times they just need to talk about everything that is going on and just need someone to listen to them. Take an entrepreneur out to coffee and just ask them how things are going. Ask them about any troubles they are running into or bright spots they are encountering.

3. Challenge them

You must first establish a relationship with the entrepreneur. Maybe it’s by becoming a regular at their business or restaurant. You will communicate that you are a supporter and you will begin to earn their trust. Entrepreneurs often have a myriad of drive-by critics. That’s not what they need. What they need is a challenge from a friend, or someone they know who supports them. Every entrepreneur has blind spots that need to be addressed. Work hard to earn the ability to challenge and sharpen them.

4. Keep encouraging them

Don’t focus too much on where the entrepreneur is currently at, but instead focus on where they someday could be. Far too many people, myself included, have taken it upon their own shoulders to swiftly judge and condemn a new business as a complete failure because of a few weaknesses in the beginning. Consistent support is like sweet honey to the entrepreneur, especially during the early stages. So once you find an entrepreneur, keep encouraging them.

I saw Allen Iverson’s retirement speech the other day and a few things struck me while he was talking. There were thousands of people that he has brushed shoulders with over his life and career, but in the end, in the final moments of reflection as he looked back over his life, a small handful of people stuck out above everyone else. It was those that had simply given him an opportunity to play in high school, college and finally in the NBA. It was the few that had encouraged him, especially his mother. Lastly, he mentioned a coach that cared enough about his development to really challenge him, even when he wanted nothing of it.

How to take action

1. Find an entrepreneur. Find someone in your community that is beginning a new venture. Keep your eyes open for new businesses, coffee shops, pubs and stores. Support an artist. Take people seriously when they tell you what they want to be or what they want to do when they grow up.

2. Give them business. Go and buy their food, coffee and wares. It might not always be very good at first, but that’s to be expected. Growth doesn’t happen overnight. Giving them business will help them hone their craft.

3. Give them more business. I have some friends out in Hawaii starting a bakery right now. (Tin Shack Bakery, Big Island) If I was out there right now I would be eating and having coffee there everyday. Tell everyone you know about the business, service or product. If they sell a product, buy it and give it away as gifts to friends and family members. Businesses need the most amount of help in the beginning, much like children.

4. Blow their socks off and ask if there is anything you can do to help. There are usually a thousand items on every entrepreneurs to-do list, and offering to take one of them off their shoulders might very well bring them to tears.

If you make it a habit to encourage the entrepreneurs around you, don’t be surprised if you find yourself being mentioned in a retirement speech, an acceptance speech or even a biography. They need your support.

Did you have someone that really encouraged you when you were younger? A teacher, a coach, a parent, friend or sibling? I’d love to hear some of you stories!


  1. I had a second grade school teacher who for some reason took me under her wing. I was a very poor kid, from a poor family. It must have really shown. She poured extra love into me. I noticed that she seemed to like me more than anyone and showed it. Perhaps she didn’t but it seemed that way to me. I was a very timid child and I will never forget her in my time of fear and insecurities. She took time to make me feel loved.

  2. What a well written and truthful article. My experience has been that folks tend to follow me in “ventures”…because of the “if he can do it and I surely can” logic. I guess I make it look easy when it is anything but….As you point out it can be lonely at times as entrepreneurs are thinkers….always thinking ahead …to the next problem…opportunity….headache. Folks just don’t understand the commitment it takes to be in business today.

  3. Wow! The loneliness part got me. I work from home and make a lot of money, but I get lonely.

    Also, the “listen to them” comment. So true- so many ideas run through my head, debating with myself. It’s incredible. Reading what you wrote about it made me feel known and encouraged. Thank you so much.

    Ps: I’m going to look in to appliances on Craigslist. Thanks so much Ryan!


Please enter your comment!
Please enter your name here