Interested in starting your own entrepreneurial journey in coaching but unsure what to expect? Then read up on our interview with Jeffrey Sesol, Founder of Pull the Chute, located in Gallatin, TN, USA.

What's your business, and who are your customers?

I have been entrepreneurial for 30 + years. Over that time, I have had many of my businesses. I have also consulted many business owners on operations and growth. At some point in your life, you look in the mirror and say, "How am I gonna leave my mark on this world?" For me, that was when I turned 60. During a bit of self-reflection, I decided that my true passion was to help entrepreneurs and business executives maximize their potential. So, I decided that my mission over the next ten years is to help as many small to medium-size businesses grow to the next level of success. From there, I created Pull the Chute, focusing on business, executive, and/or leadership coaching. By coaching vs. consulting, I can help more companies, executives, and leaders at one time. A couple of important factors I have found over the years is that owners/founders must learn to get out of their way and trust their people. Equally important is to give their people an environment where they feel appreciated, supported, and have a voice. The underlying goal is to grow your people, and you will grow your company.

Tell us about yourself

I enjoy helping others. According to Meyers Briggs, my personality type is an Assertive Protagonist. I feel called to serve a greater purpose in life. Thoughtful and idealistic, I strive to impact other people and the world around me positively. I rarely shy away from an opportunity to do the right thing, even when doing so is far from easy. Meyers Briggs got this one right. This analysis is exactly who I am.

I have recently told people that I believe there are five important birthdays in your life. When you turn 16 because you can drive, when you turn 21 because you're legal, when you turn 40 because you realize, statistically, your life is half over, and you start to look at items on your bucket list to do while you can. For me, that was to go skydiving. You take a plane up to 14,000 feet and then tumble out, falling at 120 mph. It's hard to breathe; one movement spins you out of control. Everything is happening so fast you can't see where you're at or where you want to go. At 5,500 feet, you Pull the Chute suddenly, you can breathe again, you're in control, and you can see where and where you want to go. Isn't that like life? And if you own a business, isn't that how you feel about running your business? The next important birthday is when you turn 60 and realize that you are on that downward slope in life, and you look in the mirror and ask yourself, "What have I done to leave my mark in this world?" For me, that's when I decided that I wanted to follow my passion for helping others, especially small to medium-size businesses. Therefore, I started to Pull the Chute as a coaching business that would allow people, for at least one hour a week, to 'pull the chute,' take a breath, feel in control, see where they're at and where they want to go. Owning a business or being the boss can be a lonely place. It is invaluable to have a coach that owners/executives can confide in, plan together, help make decisions, and hold them accountable.

What's your biggest accomplishment as a business owner?

Previously, it was when I grew our company Freedrive, a web-based storage company we started in 1998. By 2001, we had grown to 18 million users and 28 million by 2003. Along with that success, we built a culture that allowed our employees to be the best they could be, which led to our success, as our people would always go above and beyond without being asked.

Now, I am happy to say that, using The PTC Method, I recently helped a client grow their 10-year-old company to increase their revenue by 348%, grow clients from 22 to 54, grow employees from 18 to 42, and increase retention from 50% to 93%. Then be able to walk away knowing that not only did I guide them to grow their business, but I also helped them grow their people and set them on a path of continued growth for years to come.

What's one of the hardest things that come with being a business owner?

Over the years, I would say that doubt was probably the hardest thing to deal with. Are we making the right decisions? Have we thought through everything? Of course, having lived through the rollercoaster that is entrepreneurship is why I decided to become a coach for others. I know what doubt can do to you. It beats you up inside sometimes; it can paralyze you. You know what you must do but don't do it because you have doubts. A coach can remove those doubts and provide you with an accountability partner. Being a business owner can be a very lonely place. But it doesn't have to be.

What are the top tips you'd give to anyone looking to start, run and grow a business today?

  1. Know your why. Why are you starting this business? Is it for the money? Is it your passion or because you think you can do it better? Whatever your reason, be sure you know your why because knowing your why will get you through those times when things don't go as planned or when things get tough.
  2. Identify what you do well and what you don't do well. Fill your voids with those who help you succeed and be your best. You don't have to have all the answers to learn to rely on others.
  3. Get out of your way. This is the business owner's biggest problem when it comes to growth. Owners that have their fingers in every aspect of the business become the bottleneck that will prohibit the company from scaling. Allow your people to do their jobs, let them know they are appreciated, supported, and have a voice in the business. The result will be a business that not only grows and scales but has limitless potential.

Is there anything else you'd like to share?

I started this coaching business as a way to give back. I wish I had thought of having a business coach back in the day. Today, it's essential for business owners to not look at coaching as a sign of weakness on their part but rather as a sign of strength and commitment to learn continually, adjust and grow. It's always important to want to get better and be your best, understanding that you don't have all the answers, but rather be able to ask the right questions and work with a coach to help get the solutions you can support and live with.

Where can people find you and your business?


If you like what you've read here and have your own story as a solo or small business entrepreneur that you'd like to share, then please answer these interview questions. We'd love to feature your journey on these pages.

Turn your craft into recurring revenue with Subkit. Start your subscription offering in minutes and supercharge it with growth levers. Get early access here.