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Jeff Sesol of Pull the Chute: Five Things Business Leaders Can Do To Create A Fantastic Work Culture

Oct 27, 2021

Authority Magazine
In-depth Interviews with Authorities in Pop Culture, Business, Tech, Wellness, & Social Impact

As a part of my series about how leaders can create a “fantastic work culture”, I had the pleasure of interviewing Jeffrey Sesol

Jeffrey (“Jeff”) Sesol has spent the majority of his career as an entrepreneur. He has started and sold several companies and now acts as a business coach for others. Whether running his own companies or helping other business owners, he is constantly introducing/supporting the strategy that will take the company to the next level. In the beginning, the focus was on technology, but over the last 10 years, he has taken companies to the next level by leveraging their people. His career spans several decades of the technology revolution, where his experience has led him from Fortune 500 Corporations (Harris Bank/Bank of Montreal) to Internet start-ups and successes such as As the founder and inventor of web-based storage, Jeff led a team that grew to 28 million users around the world in only 18 months. Jeff is always exploring and integrating new ways to help companies grow to the next level. He has spent the last 10 years focused on business coaching, executive coaching and leadership coaching for several companies. Coaching them to build a culture that is foundationally and operationally sound, preparing business for growth. You can learn more about Jeff at

Thank you so much for doing this with us! Can you tell us a story about what brought you to this specific career path?

I started my career at Harris Bank back in 1980. Yes, if you do the math that was 41 years ago, where did that time go? It was a decade of incredible growth in technology. Wang and IBM were just being introduced and at the bank, I had a boss that realized he had a gift when it came to PCs. I taught myself to program and took that skill into the bank, where my boss automated the Trust Fee Dept. We had our own computer room separate from the Banks IT department and we really were able to get a lot of things done without the red tape. In 1989 Bank of Montreal bought out Harris Bank. It took a couple of years for them to realize that we were doing our own thing, but once they found out, the handcuffs went on and by 1993, now an Operations Officer, I had enough and left the corporate world forever.

In 1994 I started my first company, FuturesNet. It was a network for the Futures and Options Industry. It was built with a 4-disk install set (some of you may remember those days) and a bank of modems. We had the Chicago Mercantile Exchange, New York Mercantile Exchange, the London Financial Futures, Smith Barney, and a handful of boutique firms all using the platform. In 1995, they decided to move things to this new platform called the Internet and by 1996, when everyone else was doing brochure sites, they were leveraging a database-driven platform to support their clients. In 1998, I decided to take a leap of faith. I noticed that most of the users were focusing on one particular service more than any of the other services. It was the ability to upload a file from a PC to the FuturesNet servers and get to it from any other PC with a web browser. So we stripped that piece of the platform out and called it FreeDrive, 20 MB of storage on the Internet. Yes, history shows that I was one of the founding fathers of what we know today as web-based storage. By 2001, they were offering 50 MB of storage and we had 18 million people worldwide using the platform. In that same year, we sold the majority of the company to Motorola, EDS, and EMC. (the darlings of the internet) I spent the next 2 years traveling the country looking for the latest/greatest technologies for FreeDrive and talking in front of 5 to 5,000 people about FreeDrive.

In 2003, my time with FreeDrive had come to an end, but for me , that was only the beginning. I found a niche helping companies streamline/automate their operations. When one company grew from $2 million a year to $24 million, they never had to add anyone to the operations area because I had automated the operations infrastructure. While doing this, I began providing business coaching, executive coaching, and team building, leveraging the lessons learned from the culture I built at FreeDrive. It was important to encourage employees to voice opinions, thoughts, and ideas. It's one of the factors that allowed FreeDrive to grow as it did.

Over the last 18 years, I have enjoyed helping many companies get to the next level but it wasn't until recently that I took time to reflect on my career and what brought me the most satisfaction. What was I truly passionate about? It always came back to helping businesses and people grow. Whether it was in my own businesses or others, the answer was the same.

As I have said to some people, ‘I've been around the block more than once’, and although every situation is different, those trips around the block have taught me a lot. So, I decided that I wanted to take those experiences and "pay it forward". Help others grow their businesses and themselves personally. The focus of the growth is on the people. 79% of employees leave their job because they feel unappreciated. My goal is to help as many companies as I can while developing a culture that is honest, caring, respectful, and supportive. Help develop companies where the employees care enough about the business to say, "This is my company too!". A company where the employees wake up every morning excited about coming to work.

During the pandemic, I wrote a series of blogs around the concept of Grow your People, Grow your Company. One of those blogs, ‘Pull the Chute’, about my own experience of skydiving and how, after jumping out of a perfectly good plane, I was falling at 120 mph, it was hard to breathe , one small movement sent me spinning out of control it was hard to see where I was going. Then at 5,500 feet, I was able to pull the chute, and everything came to an immediate stop; I could breathe again; I was in control, I could see where I was at and where I wanted to go. Isn't that a lot about life, both business and personal? You feel like you are falling at 120 mph and one wrong move can send you spinning out of control; it’s hard to breathe. That particular blog saw a substantial number of readers and I received some amazing responses. Taking my own advice, I decided to 'Pull the Chute', and take a look around. I realized what I was really passionate about, helping others to be the best they can be, especially small to medium size businesses. The funny thing is that I had been doing it for years but never formalized it. So, I decided to take my life to the next level by launching the 'Pull the Chute' brand as a way to pay forward all the things I've learned over the years. I feel that this is the best way to get others to pull the chute in their business/life, take a moment to look around, see where they are and where they want to go.
This is why I started Pull the Chute – Grow your people, Grow your Company.

Can you share the most interesting story that happened to you since you began leading your company?

I would think that the latest company I worked with would probably be the most interesting.
The company at the time was a 12+ year old company that had been stuck at $1.6 million for a couple of years and couldn’t get to the next level. They had 14 people working for them and 18 accounts.
The first thing I did when I came in was to interview all the people; I wanted to get a sense of how they thought things were going in the company. This also gave me a chance to gauge who was vested in the company and who was just going through the motions. I found out they loved the culture and the leadership, but in the same breath didn’t feel confident that the leadership was growing the company in the correct manner. I spent time with the leadership, coaching them how to work through the issues, putting together a strategy and a plan that utilized small incremental compound growth. I believe if you make too many changes too fast you will cause whiplash within the company and that can be counterproductive. In turn, I was able to coach the people within the company on leadership skills, how to approach clients, how to understand the client better and educate them to be the best they can be. We also worked on client retention. They were at 50% client retention. How can you grow a company if you are losing one client every time you sign two? I convinced the CFO to let the Account Directors start onsite visits, spend time and talk to the clients. Get a sense of how they felt things were going and build a relationship. There were a lot of other factors that were involved as well, but the result was they grew their revenue by 348%. They went from 18 to 54 clients, the number of people that worked for the company grew by 300%,but for me, the best stat is that they increased client retention from 50% to 93%(even through the pandemic).

Are you working on any exciting projects now? How do you think that will help people?
We live in this new era where if you want to make a change, you need to talk about it. There are a lot of business owners, C-level people who have created amazing cultures, are invested in their people, and go the extra mile to help them become successful. Of course, we have the opposite side; there are business owners that belittle, ridicule and basically throw their people under the bus. We need to change those people. The top-down mentality must go. It’s all about respect and leadership. Being a good leader doesn’t just happen; it takes a good leader to create a good leader. So, I am launching the ‘Pull the Chute – Podcast” I will be interviewing business owners and C-Level individuals about their culture, what has worked and what didn’t work. How they became better leaders. I am very excited about this and it should launch over the next few weeks.

Ok, lets jump to the main part of our interview. According to this study cited in Forbes, more than half of the US workforce is unhappy. Why do you think that number is so high?

I think several reasons - compounded the issues and created the results. Let’s start with the fact that most people are not doing what they really want to do. Let’s face it, how many people go to college and then must settle for a job outside of their degree? According to a recent CBS News article, 45% of the 2020 graduates are still looking for work in their field, 41% have taken jobs that don’t require a degree at all. When you’re not doing what you want, it’s hard to be happy. Add that to the fact that only one in 10 people actually possess or have had any type of training when it comes to managing people. It’s a recipe for disaster. Most of those that settle for a job end up staying longer than they should, dealing with difficult cultures because, at some point, they must make a choice between just dealing with the situation or providing for their family. They can’t just quit, and they find it hard to find the time to look for a new job. I think we could drastically change the number of unhappy people by providing a supportive, appreciative, and caring culture. Bosses and/or the business owners don’t know how to use 2 simple words, “Good Job” or “Thank you”. Those simple words can change everything. Several years ago, I was trying to help a woman grow her company; she wanted me to be the acting COO. We agreed she would be the face of the company and bring in sales and I would run the back end of the business. One of the first things I did was interview her people. This was a small company; she had about 15 people at the time. I asked a series of questions to get a sense of the culture. The result was that 87% of the people told me that they felt unappreciated, the owner would never tell them good job or thank you. When I confronted her with this information, her response was, why do I have to tell them? They should know it. I was blown away by that response. Human beings need to not only feel appreciated, but they also need to hear that they are appreciated. People will go to the nth degree if they know they are appreciated.

Based on your experience or research, how do you think an unhappy workforce will impact a) company productivity b) company profitability c) and employee health and wellbeing?
I can tell with 100% certainty that if people are unhappy, they are doing the minimal work it takes to get through the day. They do enough to keep their jobs. They offer nothing in return. This, in turn, does nothing to increase company profitability; as a matter of fact, it takes from the profitability. Finally, when it comes to health and wellbeing? When people feel as though they are appreciated, they feel needed. When they feel needed, they don’t want to disappoint. All that leads to taking a positive outlook in both physical and mental health. There is a strong correlation between being unhappy at work and sick days taken. I can attest to this personally; when I first started my career at Harris Bank in Chicago, I had a boss that would yell, insult and belittle me. That first year, I was allowed 10 sick days; you can bet I took them all, affecting my performance reviews. After that year, I was moved to a different area and had an amazing boss who was appreciative and supportive. I didn’t take a sick day for the next 10 years.

Can you share 5 things that managers and executives should be doing to improve their company work culture? Can you give a personal story or example for each?

5) Make it fun – When I ran my company Freedrive, we provided the developers a room with video games, a pool table and a fridge with beers. We never hassled the team; everyone knew they had a job to do.

4) Let them have a voice – We had an open-door policy along with an open voice policy. No concern, comment, or idea was bad, and we wanted to hear what everyone had to say. Does that mean we implemented every idea? Of course not, but when we didn’t, we were able to show them why. Either it wasn’t the time or wasn’t going to work. They knew they were taken seriously.

3) Be willing to stand side-by-side with them. – I was the CTO of the company, I spent many hours helping our developers work through issues. Together we would stand at the marker board drawing out the best solutions. They always knew that I would be there to help if they needed it. The same can be said for the rest of the staff. They knew we had their back.

2) Show them that you appreciate them – Once a quarter, we would take the entire staff out as a way to say thank you for all their hard work. We would acknowledge specific people for specific achievements etc. The Result: p eople were willing to do whatever it took for us as a business to be successful. I once asked how many people had worked a 40-hour workday for us. 12 people raised their hands. One of the people said, you mean a 40-hour work week, not day right? I said no, a 40-hour workday, that meant they came in on a Monday and didn’t go home until Wednesday. I never asked them to do this; they did it on their own. Yes, it was the programmers, and we know they are a different breed, but it also shows that when you show people they are appreciated, they will go the extra mile to succeed.

1) Remember it’s not about you – The worst thing an owner or leader can do is make the success be all about their achievements when in reality, they could have never been successful without the team of people around them. When something goes wrong, be willing to defend them; when something goes right, make it about them.

It's very nice to suggest ideas, but it seems like we have to “change the culture regarding work culture”. What can we do as a society to make a broader change in the US workforce’s work culture?

The “Me” generation, better known as the Baby Boomers, created the self-involved era that has resulted in the work environment we know live in. Writer, Tom Wolfe, dubbed the 1970’s the “Me Decade”, the rise of a time when "self-realization" and "self-fulfillment" became cultural aspirations to which young people ascribed higher importance than social responsibility.
We have to begin with the realization that it’s not about me. I’ve been married for 40+ years; when we decided to stop keeping score and did things for each other, we didn’t expect things in return. Instead, we do things for each other because we want to. It changed our entire relationship. As a business culture, we need to start doing things because we care and not having the ‘what’s in it for me’ attitude. Let people have a voice, tell them when they do a good job, show them they are appreciated. This will, in turn, provide huge returns in the business overall.

How would you describe your leadership or management style? Can you give us a few examples?

My leadership style is Democratic/participative style. I walk the talk to earn respect. I expect everyone to be adults, do their job, meet deadlines. I don’t micromanage. But instead, coach people to be the best they can be. For example, when I help someone respond to an email, I have them write the first response. If it needs adjustments, I make the adjustments outlining why I am making those changes but encourage them to put it in their own voice. When we need to make a change to a process, I will involve all those being affected and ask for their input. From there, we can make the best decision based on everyone’s input. Note: you can’t always include everyone’s input; that’s why it is important to explain how/why you came to that conclusion.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

If I must pick only one, it would be my boss of 13 years at Harris Bank where I started my career. Wendy Baily taught me several things that I use even today. Here are a few of them:
1) Respect those in higher authority, but don’t be intimidated. They put their pants on the same way you do, one leg at a time.
2) It’s ok if you don’t have the answer. Don’t be afraid to say to them, can I get back to you on that. But more important, don’t make up the answer. They will either know or find out and your reputation will be ruined in their minds.
3) Make sure your people are on the right seat on the bus. She saw abilities in me that I didn’t see and, in the end, gave me the opportunity to thrive in a role that didn’t even exist in her department. The result: I became a bank officer.
Finally, be careful what you say to or about people. You never know when you may have to work with them.

How have you used your success to bring goodness to the world?

My personality is an Assertive Protagonist. I do my best to help others to be their best. I work hard to always see the good in others. The glass is always half-full, never half-empty. I look to understand a situation before reacting. I love to coach others and provide them with as much positive energy as I can.

Can you please give us your favorite “Life Lesson Quote"? Can you share how that was relevant to you in your life?

“Always do the right thing, even if it doesn’t seem fair at the time.”

Like many people, there have been times in my life where I could have easily become angry, vengeful, vindictive, or even downright mean. But I have always taken the high road, something my dad taught me very early in my adulthood. It has served me well the majority of the time and it has come back to be a positive result.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

This is an easy one – #PulltheChute. Take a moment, whether in business or in your life, to Pull the Chute; see where you are and decide where you want to go. Then develop a strategy, create a plan and get yourself moving. But don’t forget to periodically pull the chute to see that you are still on the right path. The worst thing you can do is get to the top of the mountain, only to realize you are on the wrong mountain.

Thank you for these fantastic insights. We wish you continued success!

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