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You Can Embrace Failure but Don't Expect a Hug From the Business World When You Do Three entrepreneurs discuss careers riddled with mistakes that nonetheless have turned out quite satisfactory.

By Phil La Duke Edited by Frances Dodds

Opinions expressed by Entrepreneur contributors are their own.


F. Scott Fitzgerald once said, not to me of course, that there are no second acts in life. Tom Hanks, playing Jimmy Duggan in A League Of Their Own said, "there's not crying in baseball." Joe Martin, the creator of the comic strips Willie and Ethel and Mr. Boffo, tells the tale of him as a young man receiving a check for a million dollars. He claims that he tore it up and went up to the top of a mountain to contemplate the mistakes of mankind…one man in particular. What each was trying to convey is that there are no "do overs" in life. One can't change the formula of Coke, have ruinous consequences and simply ask for a mulligan. To be sure, the corporate world is long on memory and short on forgiveness.

This got me thinking about what successful entrepreneurs would they could do over. If given the opportunity to do something differently to what seminal moment in their lives would they point; what would be the one thing they would change? I asked four questions:

  1. Throughout your career, what mistake or bad decision did you make that you wish you could do differently?
  2. What did you learn from that mistake/decision that made you more successful?
  3. Do you ever wish you had a 9-to-5 job?

My research for this piece was both positively enlightening and disappointing. I selfishly saw it as an opportunity to promote some highly successful entrepreneurs from my hometown, Detroit. The first lesson I learned is that Detroit entrepreneurs tend to be smug, condescending and completely uninterested in communicating with me or Entrepreneur. I sent my questions via email, not expecting that they would want to meet with me or have a conversation with me even via phone, but I did think the self important bags of puss would have the courtesy that God gave geese and at least send me an email answering the four questions. I received a series of curt and condescending responses letting me know what they thought of my request; I half expected them to send me coupons. Another disappointment was the owner of a internet marketing company who ironically didn't seem able to answer the questions put to him with any sort of coherency.

After broadening my search I hit pay dirt. I found three really interesting people who, more important than being interesting, were willing not only to talk to me, but were genuinely interested in helping fledging entrepreneurs to learn from there mistakes. The three: Gary Alexander, a self-self described "a serial entrepreneur" who joked that he had "made a more than (his) fair share (of mistakes)" and may struggle to choose just one (Gary has built numerous companies from nothing into multi-million dollar concerns that he sells and starts over); Devin Alexander, a celebrity chef, Media Personality, Healthy Comfort Food Chef, Weight Loss Expert, and New York Times Bestselling Author who is perhaps best know as the Chef of NBC's "The Biggest Loser"; and Dr. Paul Marciano, a leading authority on employee engagement and retention, and best selling author of two books: Carrots and Sticks Don't Work and SuperTeams: Using the Principles of RESPECT™ to Unleash Explosive Business Performance.

While I am disappointed that my hometown newsmakers snubbed me (as I write this I am mentally flipping them the proverbial bird), had they not, I would not have met three of the most dynamic and charismatic individuals in the world of entrepreneurship, so without any more yammering by me, is what they had to say:

Throughout your career, what mistake or bad decision did you make that you wish you could do differently?

Gary Alexander: "One thing I learned that every mistake or a set back can lead you to greater opportunity as long as you learn from it and stay persistent. Word of caution, don't confuse persistency with stubbornness. I have seen so many good people and companies go down, just because they refused to learn from their mistakes and kept repeating them. Mistakes offer us a wealth of knowledge and great opportunity to learn. On personal note the mistakes that stand out for me the most:

Rapid expansion /New Product – As entrepreneurs sometimes we are too quick to get excited about new ideas and are eager to jump in head first. About 15 years ago I have decided to help my former wife to grow her small medical billing service. I just sold another company that done well and was enjoying the high of success. I felt that I can take the lessons I have learned and apply to any business, I felt I was invincible. My vision was to take her two-person medical billing service and turn it into a full-service physician medical management group for doctors. We hired a few expensive experts, expanded our staff and started door knocking… the sales cycles were very long and we met with a lot of resistance being new kids on the block. Twelve months into the venture, we were bleeding a lot of cash with not much promise on the horizon. I was faced with a tough reality of cutting my losses and getting out of the game.

The only thing that kept me in was my landlord who insisted that I would have to write a $300,000 check if I cancel the office lease early. I decided to give it another few months and started going on every sales call with our team. What struck me the most is almost every client had the same request… it went kind of like this "we are not ready to turn over the management to you but we really need help to hire/train some staff." As a good gesture we were actually giving them referrals for free… the light bulb went on, "we are giving the service that they want for free?"

Within six months we had turned the entire business structure on its head. We fired most of our management clients (a really tough thing to do when you are losing money) and evolved as a highly specialized medical staffing service, specializing in staffing medium-size medical facilities with emphasis on a business office. Three years later the company had 17 offices across the country with a healthy revenue stream and tremendous growth path. I successfully sold that company and went on making other mistakes."

Devin Alexander: "A couple of times early in my career, I didn't hire the right attorneys. The first time, I was offered a pilot on Food Network and grabbed a quick referral from someone in the business and the attorney offered. The attorney was a super hot head and seriously annoyed the network executives. We never reached an agreement…and it wasn't until later that I realized how obnoxious and overreaching my attorney was. I was super new in the business and didn't have a giant income at the time and just didn't know that something like that could happen. I also had one other experience where I had an attorney friend do a contract for a restaurant partnership. When the restaurant filed bankruptcy having not paid me (and before even rolling out my work), I was left realizing that my contract did not protect me."

Dr. Paul Marciano: "Like becoming a parent, I don't think we get a lot of advice -- or at least advice that we actually listen to -- regarding starting our own business. Both decisions are high risk and I strongly suggest not bringing both to life simultaneously. Along my 25+ year journey as an entrepreneur, I've had more "learning experiences" than I'd like to admit. Of course, what matters most is that I'm still hanging my own shingle, and I love what I do.

Among the many traits required to be successful, believing in oneself and persistence rank high. As I reflect on my career, these two factors have limited my professional growth and ability to grow my business. Failing to fully believe in myself has, at times, resulted in my listening to and being unduly influenced by others. As an entrepreneur, you should always seek advice and, in the end, always go with your gut. Believing in oneself is certainly correlated with persistence. Persistence requires truly being OK with being told "No" and coming back for more. You've gotta have the fortitude to hear – "I don't want what you're selling" – and not let it diminish you in any way. I'm not good at hearing "No" and probably move away from potential opportunities to easily. When you're told "No," figure out if you can make a smaller "ask" that gets you a "Yes." When someone says, "That's not possible," shift the conversation into, "Then let's talk about what is possible."

What did you learn from that mistake/decision that made you more successful?

Gary Alexander: "Since I don't have a formal business degree, I pretty much depend on lessons from the past. Using this particular example, I would say few things. First the obvious, take your time to learn your market and your clients. But more important, every problem presents an opportunity…entrepreneurship is nothing more than a way to solve problems: yours or others. No problems, no business.

Devin Alexander: "I've had two instances since that time that companies tried to take advantage of me. Fortunately, I had hired top attorneys who made it impossible for them to get away with anything, on contracts valued way greater than the Koo Koo Roo one, so I'm glad I learned my lesson when it wasn't critical."

Paul Marciano: "A few months ago I had the birthday -- second perhaps only to 21 -- namely, 50. As I imagine most people do, I took an inventory of my life -- where I was, how I got there, where I might be interested in going. I consider decisions with greater thought and purpose. I've gotten more clear that saying 'yes' to one thing by default means you're saying 'no' to something else. I've given up the word 'should,' e.g., 'I should re-build my website,' 'I should do more with social media', 'I should write another book,' etc. The only thing I've gotten from 'should' is a feeling of guilt. I realized that what I really should be doing was enjoying my life more. As I thought about my first 50 years, I realized that I had put considerably more effort into my work than my life. As an entrepreneur one could literally work 24/7-- and there are times to do that -- but not all the time. Don't let life pass you by and don't let work serve as the excuse for not spending more time with friends and family. You've got to create boundaries or work will eat you up."

Do you ever wish you had kept (or had) a 9-5 job?

Gary Alexander: "Are you kidding? I don't' even think I can get a 9-5 job even if I wanted one."

Devin Alexander: "NO!!"

Dr. Paul Marciano: "Do I ever regret having worked for myself instead of a 9-5? Not for a minute (OK – maybe a minute here and there). However, it is not for everyone -- especially if your life requires predictability with things like money. One tip, if you decide to work for yourself, create a social network of other entrepreneurs. It doesn't matter if they own the local dry cleaning store, antique shop, restaurant, or printing company -- it gets lonely and the best people to support you are those that understand what it takes to stand on your own every day. "

Phil La Duke


Phil La Duke is a speaker and writer. Find his books at amazon.com/author/philladuke. Twitter @philladuke

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