Jarie Bolander of JSY PR & Marketing: How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur

by Charles Purdom

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 Jarie Bolander.

Jarie Bolander is an engineer by training and an entrepreneur by nature with 25 years of experience as an entrepreneur. He has formed or been part of 6 startups in various management roles. His latest company is JSY PR & Marketing, a firm that helps IoT/Smart Home/Consumer Medical Device companies tell better stories. He is an author and his latest book is The Entrepreneur Ethos, which is also now a podcast of the same name.

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?

Jarie Bolander: Funny you should ask. I never thought in a billion years I’d be doing what I’m doing today. It’s strange how life and love can change the trajectory of our careers.

I went to school in Silicon Valley. Got a degree in Electrical Engineering and went to my first startup right out of college. It was a chip company doing massively parallel neural network processors. Hardcore semiconductor physics stuff. Cutting edge back then. That company went bankrupt but I got the startup bug and went to another semiconductor company doing speech recognition microcontrollers. Image a really bad Siri in a kids toy and you’ll get the idea of what we were doing. Super cheap. Cut every corner type stuff but bigger volumes than neural network chips for government agencies whom I can neither confirm nor deny.

This was my career for the next 20 years. Find a semiconductor startup and hope it goes big. I did 6 of them and one did hit it big in of all things DNA sequencing. Semiconductor DNA sequencing to be exact.

After that company hit it big, I went through some challenging personal issues that led to divorce. It was a hard time for me and then I met Jane.

Jane was a publicist for professional athletes. She would represent the likes of Yao Ming, Carmello Anthony, Marshawn Lynch, Dontari Poe, etc. Those athletes wanted to get noticed but also do good in their communities. We fell in love, got married, and wanted to start a family.

As we were trying to get pregnant, Jane was diagnosed with leukemia. At the time, I was working at a digital health company that I was the founder of, Lab Sensor Solutions. Since Jane could not meet people while she was going through treatment, I stepped away from my startup and started to run her company, JSY PR & Marketing.

Today, I still run her company almost four years after her death. I also found love again (we’re engaged) and have been rebuilding my life in a way that both honors the past yet be optimistic for the future. It’s a challenge for sure. I always try and remember that every day is a gift and I should use each day to its fullest.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

Jarie Bolander: No real Aha Moment but rather a moment of choice. You see, I never thought I would ever run a PR & Marketing company. I’m an engineer. The last thing on my mind as a career choice was doing this type of work. But, here is the thing that Jane and I had to grapple with.

My startup was not paying me. It was growing but we were not in any position to give out a salary. I also had to be Jane’s primary caregiver, which meant going to every appointment and making sure she was taken care of. That would have been hard to do at a startup that was not paying us.

There was one other thing to consider as well — Jane did not want to shut down her “baby.” She had worked hard for the better part of a decade building her business and she did not want to see it go away. I remember the look in her eyes when she pleaded with me to take it over. I’m not joking when I say pleaded because she got on her hands and knees to beg me to do it. How could I refuse?

So, I guess that was the Aha Moment or moment of truth. The fork in the road that set me on the path I am today.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

Jarie Bolander: I like to say that I’m an engineer by training and an entrepreneur by nature. What I mean by that is that I have always been interested in being at a startup. They are hard to avoid when you grow up in the valley. It’s not like anyone in my family was an entrepreneur or anything like that. Everyone else in my family has “normal” jobs.

What I feel put me on the path to develop the aptitude for the entrepreneur life was when I was in college. That opened my eyes to the fact that startups existed and that you could try your luck at success. So I had the curiosity ever since I could remember to want to build things but it was not until college that I could explore that curiosity.

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?

Jarie Bolander: For my current business, it was my late wife Jane. She was an inspiration to watch and learn from. For the 6 or so other startups I have been at, there are too many to list except for Geoff Zawolkow, who I started my previous company before JSY PR. We have been at several startups together and appreciate his attitude towards life and building a company.

I first met Geoff at my only truly corporate gig, Cypress Semiconductor, where I was assigned to his newly acquired Bluetooth startup to make them conform to our corporate development culture. Let’s just say it was a trial by fire for both of us and it culminated in us then going to another company together and eventually forming Lab Sensor Solutions.

What do you think makes your company stand out? Can you share a story?

Jarie Bolander: JSY PR & Marketing started as a company that focused on promoting professional athletes. As time went on, Jane realized that several of her athlete clients had non-profits so she shifted to helping them run their non-profits. When she met me, she started to look at more startups.

What seems like three types of organizations that have nothing in common, namely startups, nonprofits, and professional athletes, actually have something in common — they all never had their story straight. The reason is that most, if not all, don’t focus on storytelling — rather on getting customers or raising money.

Over time, she and I realized that the organization that tells the best story will win more customers, raise more money, and garner more press. Seems simple really but what we had found was that most organizations don’t focus on the fundamentals of storytelling — rather they only scratch the surface of what they are all about.

For example, we worked with a company called Sutro. Sutro is a water testing robot that you place in your pool or spa. Think of a Roomba for your pool.

The initial story they had was one of a gadget to help you test your pool water but that story fell flat. The reason being that customers did not want gadgets, they wanted solutions to not only solve their problem of testing their water but then what to do about it. We then helped them change the story to a Smart Water Ecosystem that supported customers with more than just a gadget. That made a huge difference.

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?

Jarie Bolander: There are several traits, values, and beliefs that I feel are important for successful business leaders and entrepreneurs. When I wrote my book, The Entrepreneur Ethos, I interviewed over 50 entrepreneurs to answer that exact question. These instrumental traits have also been confirmed by the 90+ interviews I have done for The Entrepreneur Ethos podcast.

What I believe and have confirmed by interviewing over 100 entrepreneurs is the following:

  • Be comfortable with being uncomfortable.
  • Blue-collar work ethic trumps talent every single time.
  • Be ready for the luck to find you.

All three of these came into play when I took over JSY PR & Marketing when Jane got sick. To say that I was uncomfortable with taking over my sick wife’s baby was the understatement of the century. I was freaked out beyond freaked out. I soon realized that if we wanted to survive that I had to put my pride aside and do the hard work of learning PR and Marketing.

This was not read a book type of learning but looking up 50 press contacts to pitch and then pitching them. Setting up an event where you have to call vendors and outreach for the client. Honestly, I felt it was beneath me. I was an entrepreneur who had over 10 patents. I create stuff. I build complex systems to solve problems — not call 10 vendors to get the best price on a venue.

That was humbling but it also led to meeting tons of people who recommend us to others.



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?

Jarie Bolander: Boy, that’s a good one. Early on in my career, I had a boss that told me you have to be always in charge and make sure your people are doing what you say. He was a real hardass but during social situations or with his family, he was a different person.

I tried his approach. This being a different person at work than at home. It was miserable. You’re one person and if you try and be different at work than you are at home, you’ll be conflicted. What happened to me is that I got more tough at home since that seemed to work at work. It was a disaster and ultimately led to a divorce.

I learned from that to be myself and only myself and not be Dr. Jekel and Mr. Hyde.

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?

Jarie Bolander: Set clear objectives, don’t micromanage, and seek the truth. The single biggest source of frustration that I have seen with leaders and employees is the leadership bubble.

The leadership bubble is the fantasy land that leaders and bosses live in. They create this bubble by what they say and do. Specifically, if a leader reacts poorly to the truth or can’t handle setbacks, their people won’t tell them the bad news until it’s too late. They will live in a bubble of their own creation that will lead to periodic and catastrophic bursts.

As a leader, what you say and do, no matter how trivial, gets amplified 100 fold. It’s also what others will keep as the standard to be held to. Boss gets mad at the bad news, don’t tell them about problems. Boss talks down to subordinates. Other bosses will do the same. Leaders are watched carefully and people notice things. It’s not what you say but what you tolerate.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Jarie Bolander: Tell the truth. Don’t cover up problems. As we say in the PR game, the coverup is worst than the event. Own the good and the bad. Help others be successful as well. Have an abundance mindset. There is plenty to go around.

Can you help articulate why doing that is essential today?

Jarie Bolander: You can’t hide from problems anymore. You used to go back when there was no internet. Now, whatever you do will be amplified in the next 15-minute news cycle. In fact, stupid stuff you did 5, 10, 15, even 20 years ago will come up if someone wants to take you down. The best and only way to handle that is, to tell the truth, don’t cover things up, and take the higher ground. That last one is so important that it gets overlooked by even smart people.

The higher ground means taking the argument or situation to the next level to diffuse it. That’s why it’s important, to tell the truth. For example, an oil company has a spill. Instead of minimizing it, own it and fix it out in the open. You see some of this now with the mayor of San Francisco, London Breed when it comes to the city’s COVID-19 response as well as cleaning up the corruption that she inherited. Sunlight is the best disinfectant.

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?

Jarie Bolander: The biggest mistake I see is not doing the blue-collar work to build a business. The unfun stuff. 90% of business is unfun and not that creative. Having the discipline and blue-collar work ethic to chop the wood in front of you is so important. To avoid that, you must do the stuff you dislike until you can pay someone to do it. Even then, it pays off big to do the unfun stuff as well.

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”?

Jarie Bolander: Entrepreneurs are the creatives of the business world. Our job is to create products, services, and new ways of doing things that challenge the status quo. This is inherently risky. Success is highly unlikely and therefore, the highs and lows will be more extreme than someone who has a regular job who accepts the status quo.

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.

Jarie Bolander: The highest of the high is when the company you work for or founded gets bought or goes IPO. That happened to me once and it was an amazing validation of the idea. For my current company, it’s landing a new client.

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.

Jarie Bolander: The lowest of the low for me, other than when your partner dies, is when you have to lay people off because you lost a client or are running out of money. That’s an awful feeling because now, you have impacted someone else’s life. I have had to do this several times with other businesses including the one I run now. It’s a horrible feeling.

Based on your experience can you tell us what you did to bounce back?

Jarie Bolander: I realized that I had done the best I could to avoid the situation of letting people go. It was really out of my control in one sense and not to be dwelled upon. That does not mean I did not dwell on it to learn but rather I took the time to mourn the loss of not only the people I had to let go of but also of the opportunities that were lost as well.

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.

Jarie Bolander: The five things I think you need to ride the emotional highs and lows of being an entrepreneur are the same five things I wrote about in The Entrepreneur Ethos to build a more ethical, inclusive, and resilient entrepreneur community. Those five things are:

Failure is an option but never the end result. I see failure as learning. When I had to shut down one of my companies, it felt really bad but that shut down led to a key piece of learning — sometimes your timing is off.

Integrity is my middle name. You can never go wrong if you have a high level of integrity. This came about during a partially tough negotiation where I felt I could not do what a client wanted me to do. I told them as much but they still wanted to hire me. I ended up passing on it because I knew it would waste their money and my time.

Seeking the truth will guide my decisions. Contrary to popular belief, there is objective truth, and seeking this objective truth is the best way to make decisions. This is particularly true when building a new business. When we were determining if people with EpiPen’s wanted to track them, we got an overwhelming yes response but when we asked them to buy something to track their EpiPen’s, we got crickets. That truth led us to stop wasting our time on something no one wanted.

The journey is my reward. By far the most important thing to remember when being an entrepreneur. The emotional highs and lows of being an entrepreneur are usually attributed to the external trappings of success like fame, fortune, and/or prestige. If you’re in it for the journey, then those fleeting external things don’t matter. I learned this one the hard way when one of the companies I worked for got bought. It was a joyous time but also I was wrapped up in how much I would get. That soured the whole experience and taught me that if I only want the external rewards, then I’ll never get enough.

Being an entrepreneur is an honor I must earn daily. Success can lead to getting a big head and an even bigger ego. Your past successes, while important and valuable, should never be used as a way to get lazy. What I mean by getting lazy is not earning the honor to do what we do. It’s a tremendous amount of responsibility. You can’t ride on your past successes and expect that you’ll continue to be successful. That happened to me after the exit. I thought whatever I did after would turn to gold. Turns out, success is a lot more luck than skill, and earning the honor daily gets you ready to take advantage of the luck. 

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?

Jarie Bolander: To me, resilience is being able to zig and zag around obstacles that are in your way without getting discouraged. The traits of resilient people include discipline, focus, confidence, and grit. All of those traits deal with the ability to handle the inevitable setbacks that will occur in all entrepreneurial endeavors.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

Jarie Bolander: I played a lot of sports as a kid through high school. You can’t be part of a sports team and not learn how to roll with the setbacks and struggles of losing a game. I also started working young — ten years old to be exact. That’s when I got my first job delivering papers. That paper route taught me a lot about dealing with having to get up early on a Sunday morning to deliver a paper that was 10 times as heavy as during the week. Mix that with rain and wind and it tests your resiliency to roll with what life gives you.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Jarie Bolander: Generally, I have a “what do we need to do” attitude during difficult situations. This is sometimes positive but mostly it’s about finding and executing a plan of action. When I’m in that mode, the attitude feels more negative because I’m trying to solve a problem. As a trained engineer, our job is to solve problems. No problems. No job so that tends to put me in a more negative attitude or rather outwardly negative attitude. Inside, I’m positive I can solve the problem.

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.

Jarie Bolander: I don’t believe that a positive attitude is always the way to go. I think it’s more of a realistic attitude about the situation that you’re in that produces the best results. The world or situations you find yourself in might not warrant an “everything will be fine” attitude. This is of the utmost importance during a PR crisis when pragmatic and somber trumps positive every single time.

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?

Jarie Bolander: I’m a big fan of “The Obstacle is the Way” since I have had to deal with many obstacles in my life. Before I adopted that mantra, I would get upset when faced with setbacks and challenges. It would frustrate me to no end that things would not go my way.

My attitude changed when Jane died and I had to learn what good came from it. I know it sounds weird and counterintuitive to think that good could come out of something so horrible but it did. That tragedy led me to stop drinking and focus on the personal challenges that prevented me from constructively dealing with issues. I like to say that experience led to Post Traumatic Growth since I have found love again and have been working on aligning the business to what I want to do for the rest of my career. That growth also includes tackling the challenges in my personal life that prevent me from being fully present with the new family I want to build.

How can our readers further follow you online?

Jarie Bolander: You can find me at:

  • The Entrepreneur Ethos Podcast: (https://theentrepreneurethos.com/) 
  • Twitter: @TheDailyMBA
  • LinkedIn: @jariebolander
  • My companies website JSY PR & Marketing: https://jsypr.com/

This was very inspiring. Thank you so much for the time you spent with
this. We wish you continued success and good health!

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