Being a founder, entrepreneur, or a business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur“ we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Jim Estill.
Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?
In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?
Jim Estill: I think I was born to be an entrepreneur but part of it was likely that from a young age I was praised and rewarded for the entrepreneurial things I did. For example, I shoveled driveways for money (I grew up in small-town Canada where there is lots of snow). In high school, I started a house painting business and hired my brothers and friends to paint houses. We likely painted over 100 houses in a few years.
Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?
What do you think makes your company stand out? Can you share a story?
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
Jim Estill: Taking my company public. I was advised this was the best way to fund growth. So we went public. That shortened our time horizon (although we fought hard to try to make it not happen).
Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?
What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?
Can you help articulate why doing that is essential today?
Jim Estill: Trust, credibility, and Authority attract people to work with you and encourages companies and consumers to do business with you. Consumers increasingly are looking to buy from companies they respect and trust.
What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?
Jim Estill: The biggest problem I see is overthinking and overstudying. The solution is just to do it. Try it and see what will work.
Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?
Jim Estill: Entrepreneurs by definition take risks. Not all risks work out, but some pay off hugely. Entrepreneurship is a series of wins and a series of losses. The key is to “Fail often, Fail fast, Fail Cheap”. Move on from the lows quickly and make sure they are not fatal. Failure often comes from not trying at all, rather than trying and losing some.
Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.
Jim Estill: I recall feeling elated and almost surreal doing a speech for the University of Guelph graduating class on the day I received my honorary Doctor of Laws. It was the business success that got me there and now over 1,000 people in an auditorium were listening to my “words of wisdom”.
Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.
Jim Estill: I was cheated by a business partner who I considered to be my closest friend. Discovering that was a real kick in the gut. I was in mourning from losing a close friend and at the same time, in rage at what he had done.
Based on your experience can you tell us what you did to bounce back?
Jim Estill: I think my failure philosophy helped me to bounce back. Repeat often “having a failure does not make you a failure”. “Failure is education, and I am a constant learner”.
Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.
1- I think the most important thing is to not take yourself too seriously. None of us are as good as people think when we win and none of us are as bad as people think when we lose. I recall being an early investor in Blackberry and joining the board before they went public. I served on the board for 13 years. In the early years, everyone thought I was a genius for picking Blackberry. What they did not see were the other 150 technology investments I made in that same timeframe. I left the board in 2010 and shortly after I left, everyone was talking about how bad Blackberry was. They were both — great and not great. Just like we all are.
2- I believe strongly in health and self-care. I recall once buying a company that was failing, to integrate it into ours. The company we bought had 127 employees and we had to let 100 of them go. That was a terrible day. Very difficult to feel like you are playing God and playing with peoples’ lives. I got home late but found the energy to go for a good one-hour run. It really helped reduce my stress. Find the positive things you can do for yourself in times of high stress.
3- I have a mantra or sayings I repeat often — “Successful People do Tough Things”. I recall getting up at 3:30 in the morning to drive to the airport to catch a flight. It was cold. I was tired. I simply repeated my mantra — “Successful People do Tough Things”. It drove me since I wanted to be successful. It was only later in life that I began to value sleep.
4- Another mantra I have is “What the Heck go for it anyways”. I am a bit shy naturally so reaching out to someone at a high level was intimidating. I recall doing quite a bit of business with Apple (well a lot of business for me) and we were having issues. I reached out directly to Steve Jobs. He responded and over the years I met with him, traded calls and emails. It was one of the best things I could do for my business — all spurred by “What the Heck go for it anyways”.
5- Entrepreneurs need a strong set of stress tools. Things we can do when we have stress. For me, this includes working out hard, walks in nature, meditation and I speak to my brother.
We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?
Jim Estill: I define resilience as the ability to bounce back. Resilient people learn from failures and do not dwell on them. Resilient people do not define themselves solely by their work. This gives them the ability to be more objective when business trials and tribulations happen.
Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?
In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?
Jim Estill: I would like to say I do keep a naturally positive attitude but realistically I have to work at it. I have had to train myself to compartmentalize difficult things, so they do not impact my whole life. I have spent a lot of time on the difference between worry (often catastrophizing and thinking the worst) which does not help, versus problem-solving. If a challenge can benefit from problem-solving — then do it. If not, it is likely to worry and should be dropped from the mind.
Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.
Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?
Jim Estill: “The greatest pleasure in life is doing those things people say you cannot do”. This ties to my business success. Many people said I could not do it. This drove me to persist and to succeed.
This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!