Inside the Mind of an Entrepreneur: 13 Tips for Emerging Business Owners
By Randy Kaufman and Erin Ardleigh
with research assistance from Dustin Lowman
No one experiences higher highs or lower lows than entrepreneurs.
Google “entrepreneurial mindset” and you’ll find that the five key characteristics of successful entrepreneurs are: a positive attitude, creativity, persuasive communication, intrinsic motivation, and tenacity. (Shockingly to many, risk- taking doesn’t appear in this list.)
This article contains tips from two women business owners, Erin Ardleigh (founder and president of Dynama Insurance) and me (founder and managing partner of Aker Advisors), on how to cultivate this mindset and run successful businesses. We two redheads met in our single days and bonded during a rather unforgettable five-hour drink over our love for Paris, travel, wine, shopping, and all things orange. Now both married (to men we introduced to each other), we continue to shower one another with friendship, guidance, and support.
Tips of the Trade
1. Take action. If you have an entrepreneurial itch, scratch it! Ask yourself, “What’s the worst thing that could happen?” If the answer is “failure,” congratulations, failure is a core experience of successful entrepreneurship. The best entrepreneurs don’t shy away from failure — they recognize it as an opportunity for growth. True failure does happen of course, but only when you give up.
2. Things rarely go as planned — learn your lessons and move on. If a marketing campaign doesn’t produce the traffic you were hoping for, great: You just got one step closer to marketing successfully. Humans, especially of the entrepreneurial variety, o\en seek absolute control. But we learn much more from the unintended consequences of our actions. These small mishaps, when turned into learning experiences, pave the way to long-term success.
3. Be tenacious. “Tenacity” literally means “being able to grip something firmly.” In an entrepreneurial context, that means maintaining a firm grip on your objectives and your attitude. A personal note from Randy: By now, I’ve trained many colleagues and my husband well enough to know the rules (and repeat them to others): “‘You can do it Randy’s way now or Randy’s way later, but you will eventually do it Randy’s way. ‘No’ for Randy–just another word for a challenge.”
4. Travel. Randy spent months backpacking in the Far East; Erin traveled extensively in Africa alone, meeting people living on $2 a day, without modern conveniences, who still cared for their families and ran businesses with a smile. Both were alone at times, in strange lands, taking significant risks as young women. Both say that these trips, and all of their risks, were life- changing. Travel broadens your perspective. It shows you universal human truths and the different ways people pursue them. There is no better way than traveling in foreign lands to learn that venturing outside of your comfort zone bolsters your tenacity and confidence.
On our worst days as entrepreneurs — facing cash flow issues, losing a key employee, getting ghosted by a large prospect, losing a core client, or facing a global credit crisis — we think of people we met on our respective journeys, living on $2/day, without clean water or medicine. We put our troubles in perspective. We deal with the situation at hand, calmly on the outside, no matter how frantic we feel.
5. In a man’s world, embrace your femininity. Women leaders have a slew of skills that their male counterparts lack. Research has linked female leadership to greater social responsibility, safer workplace cultures, and enhanced customer experiences (Harvard Business Review). Be not afraid to use these skills. The pressure is great to think, behave and even look like men at times. Ignore it, and thrive.
6. Network like your life depends on it…because your life does depend on it. Your professional connections become mentors, sponsors, referral sources, and even, as in our case, the dearest of friends and spouses!
7. Learn that “sales” is not a dirty word. Entrepreneurs are all in sales! (Really, all people are in sales one way or another.) Get thee to coaches for selling, branding, speaking, and leading. And, consider reading one of Randy’s favorite books: Daniel Pink, To Sell is Human (more instructive literature below).
8. Maintain a growth mindset. Humans worry. It’s natural. It’s usually a huge waste of time. We all make up stories of the future every day, all the time. Train yourself to make up best-case scenarios. Click here to learn more about the anatomy of a growth mindset.
9. Invest in yourself. Spend money to get help — as soon as possible. In your business’s early days, you might be tempted to save as much money as you can. But when you don’t invest in yourself, you end up taking on way too much responsibility and risking burnout. Investing in support frees up capacity for you to focus on what you do best.
10. Delegate your weaknesses. As an extension of #9, determine what you’re best and worst at, and pay people to handle the latter.
11. Ask for help. Share your struggles and challenges with the people close to you. People derive enormous satisfaction from helping out the people they admire. You’ll be in their shoes one day!
12. Abandon perfectionism. As Erin said on a recent episode of Randy’s podcast, “You get paid for your work being done — not for your work being perfect.” Of course, you should always aspire to the highest-possible level of quality, but perfect easily turns into the enemy of good.
13. Read. Read a lot. Read as much as you can stand. Consider pairing this short blog with some of Randy’s favorite books on the lives and minds of entrepreneurs:
Shoe Dog: A Memoir by the Creator of Nike | Phil Knight
The Everything Store: Jeff Bezos and the Age of Amazon | Brad Stone
Steve Jobs | Walter Isaacson
The Ride of a Lifetime | Robert Iger
The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers | Ben Horowitz
Walt Disney: The Triumph of the American Imagination | Neal Gabler
Entrepreneurship is not for the faint of heart. It is a long road and a lonely journey. The burdens that would otherwise get spread out across a vast organization fall squarely on the entrepreneur’s shoulders. For the entrepreneurs among you, we hope these tips help you along your journey.
Please, as always, don’t hesitate to reach out with your comments, questions and thoughts.
ABOUT THE AUTHORS
Randy Kaufman, formerly a corporate tax attorney and investment banker, is now a wealth advisor who prides herself on focusing on what matters most: clients’ peace of mind, family dynamics, and getting enough, not more. Randy is a passionate student of impact investing, strategic philanthropy, and behavioral psychology (while not a psychologist, she occasionally plays one in the boardroom). She is dedicated to helping the underprivileged, and is a proud member of global venture fund Acumen's advisory board. A thinker, learner, and pursuer of overarching truths, she is always eager to discuss big ideas about money, and its off-and-on associate, happiness.
Erin Ardleigh is the founder and president of Dynama Insurance. She has worked in the insurance industry since 2002 and founded Dynama Insurance in 2014. Her vision is to make the insurance planning process more transparent and more accessible for her clients. Erin is passionate about helping other business people, especially women. A lifelong passion for travel has led Erin across all seven continents. She finds that traveling and running a successful business have much in common – planning well, listening, continual learning and last minute problem solving when the unexpected happens!