If I knew then...

With a lifetime of experience, five successful entrepreneurs look back at their lives, careers and decisions in a letter to their 25-year-old self. There are few regrets, but many reminders — to always have and maintain integrity, emphasize trust in relationships and focus on long-term sustainable success, not only short-term wins.  

SUE WISE

Sue Wise, owner and CEO of Take Care Home Health & Take Care Advisor

Company: More than 550 employees spread through Charlotte, Manatee and Sarasota counties.

Headquarters: Sarasota

Year founded: 1995

Dear 25-year-old Sue:

You were raised on a cattle farm in a small town in Michigan by two loving, hardworking parents. Two rambunctious, energetic brothers were always at your feet, but a big sister with a big heart surrounded you.

At 23, you finished nursing school and left Kalamazoo and your family to venture to Atlanta to teach at Emory University. Barely six weeks into the new life, the phone rang. Tragically, life at that moment forever changed: Your father and brothers had perished in a plane crash, flying over the family farm. The only light was that you witnessed a small community of farmers pull together to help harvest the fields — your family’s remaining livelihood. You moved back to Michigan to cope.

You won’t yet begin to understand the underpinnings of the relationships formed in that tragic time. But I want you to realize the key was in the community and family. As you begin your lifetime relationship with your husband and consider having a family of your own (which eventually you will raise three strong, smart, beautiful daughters whom you raised to value the family bond), think about how that crosses over into your passion in life.

You will find in your heart that desire to marry the two ideals you witnessed from your mother and father: the love, labor, and dedication Bob gave to his farm (the reason why working seven days a week seems so natural) and Ruth’s sincere empathy and commitment to patients — a registered nurse working with severely challenged children, which proved ever more her patience for the change that life set for her.

Remember when obtaining your registered nurse degree didn’t feel like enough? Use your non-stop energy and intuition to pursue those passions of business and helping those in need. Is it the inability to watch your own father age and grow old that connects your deep desire to help those who are at a crisis point — to guide them and help shape their last time on this earth?

You will lean on relationships, especially when the male-dominated banking lenders have a revolving door with answers of “no.” Your father’s dedication, outside of the farm, to the community bank will connect you back home. A loan from that bank in Michigan will provide the fiscal edge to launch your dream business: private duty home health care.

Surround yourself with people whom you trust, who can be honest with you, and you can be honest with them. Just as you saw the love your father and brothers had for the land they sowed, use that same emotion, enthusiasm, and trust to build the business of your dreams.

SCOTT FISCHER

Scott Fischer, Scott Fischer Enterprises

Company: Operates Harley-Davidson dealerships. He sold his ownership stakes in Six Bends Harley-Davidson in Fort Myers and Naples Harley-Davidson in early 2018; maintains ownership of three other Harley-Davidson dealerships, in California and New Mexico, and an events facility in Fort Myers.

Headquarters: Fort Myers

Year founded: 1987

Dear 25-year-old Scott:

At 25, your entrepreneurial brain is just taking off and your vision is going to grow exponentially! Throughout your ride, do not forget these key items before twisting the throttle:

• Surround yourself with smart people. Surround yourself with experts and those who are more knowledgeable than you are. Be in a strong circle of five. Your ego will allow you to be in this circle and learn from different industries and peers. Find and develop a relationship with a mentor and/or business coach and learn as much as you can.
• Always be a student of the business. Never stop learning. Be diligent as a student for life. Often times, too many people want to be the smartest in the room and not listen. When you listen, you learn.
• Think forward, plan forward. Do not look at the past to plan the future. Look to the future and plan. Create your strategy from your plan and execute.
• Be Strategic. When you think strategically, you look for ways to alchemize, collaborate with key people and resources. Find solutions. Have a one-, three-, five- and 10-year personal and business plan. Evaluate quarterly.
• Be healthy. It is more important to have a healthy company than a smart company. Invest first in the health of your company and your employees. Develop leaders within your organization to drive your strategy and support them. Encourage. Mentor. Give Back. And, never forget – family first, business second.

Make it your passion to make people’s lives better. Work Hard. Ride Hard.

C.J. FISHMAN

C.J. Fishman, Fishman & Associates Inc.

Company: Handles commercial food service equipment, design, layout and consulting

Headquarters: Venice

Year founded: 1986

Dear 25-year-old C.J:

When I started my business with one other associate all I knew was that I was becoming an entrepreneur. What I did not know was that there is no substitute for time and experience to learn what I know now.

Some lessons learned below are for your consideration to use as you begin your business journey.

• Business is a journey and does not always guarantee the final destination you may desire.
• Long-term relationships are the hardest to build and they hurt the most to lose.
• Give the same level of commitment to your customers as you would expect someone to give you.
• Find your niche and strive to be the very best at it. You cannot be everything to everybody. If you try to, you will fail.
• Communicate first in person or second by phone; only confirm by email. Email is impersonal and easily misunderstood.
• There are no business problems, only challenges that can be resolved. You and your company should never be measured when things go easy but when there is a challenge and how you handle it.
• Never make a business decision at night. Night is the time of passion and of heart. Make the decision during the day. Day is the time of the brain and your gut instinct.
• Never worry about something you can’t control.
• Don’t ever expect anything more than you are willing to give.
• Give back more to your community than you take. Sweat equity has as much, if not more, value than a dollar donation.
• Strive for perfection, never settle for mediocrity.
• Satisfied customers will always be your best sales people.
• At the end of it all, what matters most is your family, your friends and your business relationships. If your business relationships have also become some of your friends then that is an added bonus.

So in conclusion young entrepreneur: Life is short, so work hard, play harder, have fun and make a difference in your industry and in your community.

LAUREN WEINER

Lauren Weiner, CEO and co-founder, WWC, Tampa

Company: WWC is a management-consulting firm that has 90 employees and $14.5 million in revenue in 2017.

Headquarters: Tampa

Year founded: 2004

Dear 25-year-old Lauren:

Relationships matter. These two words will take you farther than anything else in the next 20 years. Smarts and hard work and dumb luck will matter, but not nearly as much as these two words. That means:

• Talk to everyone. Some of your best connections will come from a seatmate on a plane. Your biggest sponsors throughout your career often came from chance encounters. Capitalize on them and cultivate those relationships.
• Keep track of all of your connections. Don’t just keep a stack of business cards, start a spreadsheet — early in your career — of everyone you meet, information about them, and when you last talked to them. If you don’t, you’ll lose so many valuable connections and kick yourself. Regularly reach out to them, even just with an email, to keep those relationships fresh. You won’t believe where friends from your early 20s end up.
• Treat everyone the same. Waiters and janitors are no less important than the CEO. Refuse to work with anyone who doesn’t follow this. They’re showing their true colors.
• Find your tribe. Find the people who get you, who cheer you on unconditionally, and who will support you every step of the way. You need a business tribe, a family tribe, and a friend tribe — or you’ll never survive the roller coaster of life.
• Help anyone and everyone you can. Don’t worry about what they can do for you. Being a good person matters more than quid pro quo. Help people, help companies, help causes. It makes your life richer, and helps you grow as a person and as a professional. (Also, see “karma is powerful.”)
• Karma is powerful. When you’re a good person, good things come to you. And some of the people giving you hassles now will be brought down hard by karma. Karma works.

Oh, and work harder than everyone else. That may not fit into the “relationships matter” advice, but it is critical nonetheless. Success is earned with blood, sweat and tears. Earn it.

DONNA HUNEYCUTT

Donna Huneycutt, COO and co-founder, WWC

Headquarters: Tampa

Year founded: 2004

Dear 25-year-old Donna:

Donna, at this time in your life you have a lot of tools but are just starting to gain experience navigating the world. You don’t know how your life will pan out and you worry about getting it right with every decision. Relax and lean into the uncertainty. It’s OK not to have resolution. Embrace the fact that the big picture will reveal itself over time.

• Trust your education and your track record. It will get you to where you need to be in long term.
• Prepare to fail on your journey. Failure now and then is OK.
• Never turn down an opportunity to travel, given it’s safe.
• Learn from everyone. The world is a fascinating place with endless subcultures, activities and industries. Avoid being “native” to any one way of doing things.

On the flip side, other people think and feel differently. Never assume they think and feel like you do. Some people value clarity and truth. Others value harmony and calm. Identify their business languages, love languages and friendship languages.

• Find many mentors, people who inspire you and who you want to be like. Think cognitively about what it is about them you want to mimic.

Related: develop a personal Board of Advisors, 1) a friend who will always be in your corner, 2) someone who can provide constructive feedback, 3) someone who has a lot of technical knowledge, 4) someone who is a good problem solver, 5) someone who is older and has traveled the path, and 6) someone who is younger and share what the latest thinking is.

• Trust your gut about physical safety. Period.

• One day you will sit in a restaurant in Paris brooding about your job. Your dinner companion will share his history as a survivor of a concentration camp and say “I feel lucky, look at this restaurant, taste this food!” Enjoy the good.