Being an Entrepreneur Means Being a Risk Taker, Dreamer and Having a Fire in Your Belly

When Willie Degel set his mind on success, he stopped at nothing to make it happen.
Being an Entrepreneur Means Being a Risk Taker, Dreamer and Having a Fire in Your Belly
Image credit: Willie Degel

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Editorial Director
6 min read

In this ongoing series, we are sharing advice, tips and insights from who are out there doing battle day in and day out. (Answers have been edited and condensed for clarity.)

Who are you and what’s your business?
I’m Willie Degel, founder and CEO of the New York-based Uncle Jack’s Steakhouse chain, which I started 20 years ago with a single location.
What does the word “entrepreneur” mean to you?

An entrepreneur is a visionary, a , a dreamer, a motivator, and a problem solver. He has a fire burning inside his belly, a vision and a dream that he will do anything and everything in his power to bring to life. He will set himself up to succeed, put the pieces in place to make it happen, take his entire team with him, and learn from his failures so that he can keep going and keep getting better. 

How has your business grown since you started?
Today I operate three fine-dining Uncle Jack’s Steakhouse restaurants in , a fast-casual Jack’s Shack Organic Eatery on Long Island, and a farm-to-table concept called Uncle Jack’s Meat House that opened last year in suburban Atlanta with a second location scheduled to open in Queens shortly. I also hosted The Food Network’s  Stakeout reality show from 2012 to 2014, helping restaurateurs identify and solve their service problems.

Related: Entrepreneurship Is All About the Fight

What was your toughest challenge and how did you overcome it?
Raising the capital for my first Uncle Jack’s Steakhouse, which opened in 1990. I was only 29 years old. I’d been running a modest bar and restaurant for two years, but I wanted to open an upscale chophouse. I designed an 1890s Prohibition-style Victorian saloon with a hand-carved mahogany bar and walls, copper-pressed ceilings, and a fine-dining menu, but I needed the money to make it happen.  I did it by enlisting friends and family as angel investors. They believed in me and my dream. They knew I would succeed because of my passion and drive.

What’s the problem you just solved or are attacking now?
Last year’s increase in New York City from $5 to $7.50 an hour for tipped employees would have added $350,000 to the at my three Uncle Jack’s Steakhouse restaurants. Clearly, I couldn’t pass costs on that scale along to my customers. This forced me to cut a busboy position, which amounted to 20% of my front-house staff. Even then it offset only 30% of the cost so I had to reduce portion sizes and absorb the rest, including higher workers compensation insurance and FICA taxes caused by the minimum wage increase. And it’s not over. Increases for other types of restaurant employees are going to be phased in by 2019, so I will have to take even more drastic measures simply to survive.

Related: Being an Entrepreneur Means Finding Profit in Your Passion

What have you learned through attacking this problem?
You can’t fight City Hall -- even though they seem to have no clue what it takes to run a small business -- so you have to figure out how to work smarter. You have to be willing to change things you once thought untouchable, like the bus boys I considered a pivotal part of Uncle Jack’s customer service experience. You have to challenge conventional wisdom, like the idea that every table should get a basket of free bread. (I tried to charge for bread like they do in Europe, but customers complained so I went back to free.) And you have to do it without undermining your value. For me, that means refusing to compromise on food quality and continuing to buy the best beef on the market. There are lines you simply cannot cross.

What’s the most important trait in a new hire and why?
Passion and energy. These are things you can’t teach. You’re either born with them or you’re not. People with these traits multi-task well, and that’s critical in my business, especially these days when staffs are getting leaner to control costs. Take a manager. He or she has to know how to bartend, wait tables, wash dishes, greet people, schmooze them so that they’ll hug you and thank you even if they’ve had to wait 20 minutes to get a table! A manager needs to solve dozens of problems a day, deal with drama among the staff, and still keep their game face and love what they’re doing. You can have a resume a mile long, but if you’re not the Energizer Bunny, I’m not going to hire you. 

Related: How to Inspire Innovation Within Your Business

What trait do you depend on most when making decisions and why is that useful for you? 
I go from the gut. (My friends would point out that mine is ample enough to handle pretty much anything.) Of course, I look at trends -- what’s selling, what’s not, why is one store doing better than the others -- but I don’t dwell on data or poll my team for their opinions. I can size up the situation instinctively and make up my mind almost instantly. It serves me well because I’m usually right and because it sends a signal to my employees that I’m a strong leader. They depend on me and my vision, and the fact that I’m decisive helps give them confidence that they are backing the right horse.

How has your leadership style evolved?
I used to be able to make every decision and solve every problem myself. Now, with five restaurants and a sixth about to open, I have to delegate. I have to empower others to be my working partners. That’s hard for someone with my personality. I’m a perfectionist, I know what I want, and I have no patience for anyone who doesn’t see things the same way or run as tight a ship as I do. But I hire good people and I’m learning to trust them. I think I’m calmer than I used to be, but I’m not sure that my employees would agree. You’d have to ask them yourself.


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