My interview with FreshBooks

I was recently interviewed by the team at FreshBooks (where my company is a happy customer by the way). Big thanks for helping me to share the Cooleaf story!

Here is the link to the original article:

Customer Stories: Meet John Duisberg, Co-Founder of Cooleaf

If you take care of your employees, your employees will take care of your customers and your customers take care of your business.

Sounds simple, right? Yet so many companies don’t seem to get it right.

Enter Cooleaf.

Cooleaf helps businesses achieve better business results through a data-driven approach to company culture.

As many startups do, Cooleaf has evolved and pivoted over time. Launching in 2011, the business was initially a health and wellness solution. Then, it shifted to focus on employee engagement. Today, it offers an Agile Business Execution platform that helps businesses achieve their goals and improve business performance with sophisticated analytics.

John Duisberg is one of 3 Cooleaf founders. Many lessons have been learned throughout his entrepreneurial journey and he shares some of those insights with us.

Meet John and learn more about the evolution of Cooleaf.


Cooleaf is focused on helping forward-thinking companies create a culture of engagement so they can attract and retain the best people for their business.

These days,companies need to connect their people to their brand in a more meaningful way. If their own people aren’t passionate about the mission and core values of the company, then how can your customers become passionate about it?

So, Cooleaf exists to help companies strengthen their brand’s value proposition in order to better connect with their employees. This way, they can strive to be a top workplace environment.


If you ask ten people what culture is, you’ll likely get ten responses. I personally believe that culture is something that has to be organic—it can’t be manufactured; however, you can be intentional and thoughtful in how you go about building culture.

We work with the leadership teams of our clients to find out what the mission and objectives of the company are. We dig deep to uncover their core values—what they want their people to live and breathe day-to-day. Then we ask ourselves: How can we help our client build a community that brings those core values to life?


We’re a small company now, so everyone works in the same room. It feels like a family. There are about 5 full-time employees at the moment and we’re all in it together, which is really fun.

The challenges come as you grow. We want to focus on preserving that entrepreneurial feel as we grow. We want every person to feel like they are an owner of the company and are invested in its long-term success.


I worked for a healthcare technology company. I was very successful and I enjoyed what I did.

I worked with one of my now co-founders. At the time, we would have those coffee shop conversations and daydream about starting a business one day. But nothing ever came of those chats. Then, he left to work at another organization. At his new job, he met our third co-founder where those coffee shop conversations continued.

It started going beyond the coffee shop conversation when my former colleague introduced me to his new colleague. That’s when we actually started to take next steps like investing our own money and starting to design stuff.

We were all still working full-time jobs. Slowly but surely, we continued to put in more resources and build up our business. There were some things I wanted to have in place before I felt comfortable enough to go off on my own.

Firstly, I wanted to have a live product, not just a concept. Secondly, I wanted to make sure we had some seed funding in place so we wouldn’t just be burning our own cash. Lastly, I wanted to have a 12-month runway to save up so I could support myself through the bumpy road of entrepreneurship.

Once I had those three things in place I felt confident to take the leap and go all-in on our company.


Well as a first step, reach out to family and friends and ask: Is this something you’d be interested in?

When I reached out to potential seed funders, I didn’t just want them to contribute financially, but also to be on board as acting advisors. Because when they’re helping you become successful, they are more likely to buy-in to the achievements of your company.

Bring your seed funders in as strategic partners of your business beyond the financial means—that’s attractive to a lot of people.


  1. It’s going to take 4x longer than you expect and cost 5x more. So prepare yourself. Things will come up and problems will arise. You have to be prepared mentally and financially to be flexible and roll with the punches.
  2. Get some traction in the market before starting to pitch your product. Before going out and pitching, figure out how to build a minimum viable product (MVP) really early on. Figure out if customers will actually pay for the thing you’re offering. That’s the ultimate test.
  3. It’s all worth it in the end. Even though it’s very hard and there are soul-searching days when you get rejected… Remember: When you finally get that win and see a customer enjoying your product—it’s totally worth it.



For us, it’s been a very good experience.

Being an entrepreneur can be very lonely. At times, you feel like you’re working on an island. So having co-founders can be very helpful in that respect.


Plus, different people bring different skills, a different network and different perspective to the table. Defining and understanding the roles of each person is really helpful. You’ll have to make decisions and move quickly in terms of the business and strategy. Being able to define your roles as co-founders is really helpful.

Keep this in mind: If you are going to work with co-founders, you’re going to be spending A LOT of time with these people, so there has to be professional respect there and you have to work to maintain it.

So, although there can be pros and cons to starting a business with one or two other people, I would absolutely recommend it. There’s a net positive that comes from that.


It’s an exciting time for us. We have built out a very strong technology platform and we have validated it by bringing on customers over the past year. Some of them are very large customers like Turner Broadcasting for example.

The next stage is to grow and scale. We’re focussed on starting to build out a strategy around customer acquisition and how to make that a repeatable process. Investing in sales and marketing effort as well as developing from a channel partner standpoint.

As we head into the remainder of this year, I’m very excited about where we are and where we will go. We plan to be cashflow positive by the end of the year!



Advice to a Career Focused College Student

I was asked recently by a senior in college, what is the best piece of advice I could share as he finishes his final year?

My response was to use the ‘feedback tactic’ to his advantage while he still can. 

I shared that he was in a unique spot where he could reach out to just about any senior leader in any company and simply ask for their feedback, as a college student who is interested in learning from them and interested in making a career decision. 

Most leaders like to help and also like to share their lessons learned of their career to someone they believe is truly interested. It’s amazing who you can connect with through a humble outreach and an ask for a coffee or short phone call. (plus, to be honest, people like to talk about themselves)

I told him this is a great way to build his network of business leaders, potentially get introduced to someone to land a job, and genuinely learn from very smart and successful people.  I suggested to make a list of the most interesting companies he could think of and start going through Linkedin to look up their CEO’s or other company leaders in his area of interest and then simply reach out to them for feedback.

He later emailed me and said this was the most practical piece of advice anyone has given him as a college senior, so I hope it can help others as well. 

Last Letter to my Dad

I recently lost my father. It was a complete shock to me. He was 69 years young.

I’ve been sharing with those that I know to tell the people they care about, that they love them every chance they get. Here is my last letter to my Dad that I plan to read at his memorial service this weekend.


I know you always enjoyed my writing, which is why I wanted to send you this last letter even though you have now moved on from this life. I mentioned to you in the past that you were an excellent writer and I admired and respected you for that. I wish you had started a blog about your own journey and lessons learned in life that I could now look back on.

Where should I start? I never thought you passing would happen like this without me being able to talk to you or say goodbye. You were so young at age 69 to go. I’m so sorry we did not talk more over the last couple years. I mistakenly thought we could always talk later and I am now wrong. I’m telling all my friends to make sure to tell the people that they care about, that they love them every chance they get. Family is all that we have and we can never get them back.

When I was little, you and Mom got divorced. I really don’t remember that too much. I just remember you having to leave at the end of each weekend. We were really close as I was growing up. I looked up to you so much and just enjoyed being around you. Looking back now I realize the sacrifices you made to visit me as often as you did. You were a good father and I love you very much for always believing in me and supporting me.

I remember when you would come in town we would always have to work on something like cleaning the house or mowing the lawn before we could go out and do ‘something special’ that you called it, which usually meant going out to eat. I now appreciate the fact that you wanted to instill in David and I a strong work ethic, which is something that I did pick up, and either good or bad, I believe that I work more and harder than most people I know.

My childhood love that we both shared together was baseball. As I got a little older, every time you came in town, we would go to the ball field and practice all day long. I loved it so much. I even loved the smell of the ball field and just being there made me feel happy.

Playing catch together was special. I remember you having your childhood baseball glove, which was an old Ted Williams model. You probably had it re-stitched and repaired over a dozen times but it was your glove and you always used it.

I remember one time it started to rain while you were hitting me ground balls at 3rd base. Neither of us wanted to stop because of the rain so we just kept going. We didn’t need to say anything. Each of us new that it was more important to keep going and not let the rain stop us. We had a special connection. We had a chemistry of love and respect for each other. Little moments like that, I’ve never spoken of before. They never seemed too important but now I know they were the most important.

You were so good about making my games too. I know it was hard with you living across the state but I really admire thinking back how much effort you made to see me play. You were always thinking about me and every time you came in town, I remember you always having a brown grocery bag full of articles and baseball tips for me. Anything that you thought could help me you would do. From purchasing a pitching machine, to catcher’s gear, you were there to support me and looking back now, those memories are very special. I remember you saying to me once that you enjoyed watching me play so much because it was like you were getting to relive your childhood dreams of playing baseball through me. Dad, I’m so grateful for these memories I have with you around the baseball field and I will never forget them. Thank you.

The older I got the more we became friends and less of a father/son relationship. We would joke around a lot and I remember you always laughing so hard that you would cry. You would always get this funny look on your face and I knew you could barely breathe from laughing so hard. The funny thing is now, when I laugh really hard, I cry too and make the same face!

To this day, David and I joke about the many funny sayings you always had. We joke about them but we both know that they make up who were and looking back now we appreciate them even more because they were yours.

There were many things you supported me on. The first time I ever drove a car was in your white Geo Prism. I remember that day so clearly. It was a Sunday and we found some back dirt roads down in Mims, FL where you let me drive. Wow, I remember the awesome feeling I had learning how to drive a stick shift, which is why I wanted a stick shift for my first car.

I remember the day you bought my first truck. You negotiated with those guys for hours. We walked out on them as if we were going to leave at least twice I think. I remember admiring how you stood your ground and finally got the deal you wanted. You taught me that it’s ok to be assertive and ask for what you want. The worst they can do is say no. You also were always careful not to just give anything to me, and we worked out a deal where I paid back the loan for the truck. When I wanted to buy a house, you suggested that we do it together as an investment. We signed a contract together for our partnership. You always showed respect for me as a person and I always tried to give you respect back which I believe is why we got along as well as we did.

There were many hard times that you experienced in your life but I admire how you always trusted in God and would practice your faith by forgiving others. You were always really good about listening even when we were in a disagreement. You taught me to always show empathy for the other person and make sure they felt heard before you try to tell your side of the story.

I do regret to say that over the last couple years, we had difficult times in our relationship. There was never anything we could not overcome though and you were good about reaching out to me to talk. The last email you sent me was on December 27th at 10:35am, saying we need to talk more and asking to set up a phone call. I responded back one hour later saying, how about tonight at 7pm? I never heard back from you but I didn’t think much of it at the time. I just figured we’d catch up soon. However, I learned not too long later that it was the last time you were going to contact me.

There are things that you taught me that I want to make sure others know about. You taught me about living for something greater than myself and I believe these individual pieces of wisdom help to define the character of the man you were.

Being a person of integrity – you always said to me that as a CEO or major league baseball player, the most important thing that you hope people admire me for is being a person of integrity, above anything else. I remember one morning we were sitting in church together and you slipped me a note with this message. You also would remind me often when we would talk. What I always loved about this was that you just knew that I was going to achieve something great and be a person of influence. You truly believed in me. So the question in your mind was once I became a person of influence, you wanted to make sure that I was going to be a person of strong character and to treat others with respect and always be a person of strong integrity and do what is right even if it’s not popular. Dad, I remember this so clearly and I promise to you, that I will always strive to be that person of great integrity that you would have wanted.

Appreciation for wisdom – every year on my birthday you would always ask, so John, how are you more wise now that you are a year older. Ha, I always knew that this question was coming and to be honest I never really new what to say. I guess this was one way you would get to us having a more meaningful conversation together. The day I graduated from college at the University of North Florida on April 30th 2005, you gave me a book called, Power. You wrote in the cover a note to me as follows.

“Happy Graduation Day, Son! May your life be filled with Power. Remember, John, power used for altruistic purposes makes power grow. But, power used for selfish reasons, makes power destroy you! Love Dad.”

– ‘Deep talks’ – you always enjoyed getting into a deep conversation with me to talk about feelings you or I had about something of meaning, even if it was a difficult subject. You weren’t interested in a superficial discussion. I remember you wanting to talk about something that was real, which usually meant some type of deep feelings we had about a particular topic. I now appreciate that you were a deep thinker and wanted to listen and learn from others at this more thoughtful level. Maybe it was because you were a psychologist by profession or maybe it was because you respected the ability to share honest feelings because of the trust you have with someone in order to do that. I admire this this about you Dad and I too enjoy having deeper discussions.

Trusting your intuition – I remember you telling me to always listen to your own intuition and that it can be very powerful. There were several times when I did not understand that about you but I do know that you believed in it and you felt that it was an important for guiding you in some life situations. I don’t know exactly what it was, but you certainly felt some type of feeling to move towards a direction, which you believed to be your intuition. I remember you also sharing with me once that you felt like you missed your calling for a profession in the stock market because of how you were able to use your intuition about picking stocks. I don’t know what all to make of that but I do know you did very well as an investor. Dad, I promise to try to always keep an open mind and listen to my intuition as it’s telling me something or giving me a direction.

Promoting peace and justice – this was a philosophy that I believe you inherited from Peter, your Dad and my Grandfather. You were never as outspoken as he was but you absolutely believed in the fundamental principals of world peace, loving your neighbor, and equal justice for all people. I respect these attributes of who you were and promise to carry on these beliefs in my life to help other people.

Dad, I miss you so much and I’m so sorry I did not have the chance to say goodbye to you. If I had the chance, I would have told you that I love you and that I will carry on the ideas that you would have wanted and to be a person that you are proud of and will treat others with respect like you would have wanted. You have taught me many things in my life, from having a strong work ethic, to the value of a dollar and being frugal, to always being a person of strong integrity. I’m grateful for the memories that I have because of how you loved me and showed me how much you cared for me as your son and friend.


I promise you that I will be that person of strong integrity, I will always work hard, I’ll seek to have more deep talks with those that I care about, I will pursue peace in my community and in the world, and most of all I will love and respect my children in ways that I know you would be proud.

I love you Dad. I’ll never forget everything you’ve taught me and I promise, you will live forever in my heart and my own family will know and respect the good and loving person you were to me and our family.

I love you,

Your son, John

Scar Tissue

“When you run a company long enough, you will get some scar tissue. After a while, you will go through so much that you don’t have any skin left. But that’s alright, scar tissue is tougher than skin.” ~ Perry Moss, President of Rubicon Global. 

Last week our hosting vendor went down causing our website to crash for about 15 minutes. Of course, during this time we were supporting one of our largest customers where they were preparing to use our platform to live-stream their employee engagement event around the world. Immediately my cell phone started blowing up about the issue while I’m trying to coordinate with our team to investigate the root cause of the problem. Meanwhile, I’m standing outside of a prospect meeting where I’m about to give a presentation. Talk about feeling a burning on the back of your neck from stress!

Later that day, I was meeting with Perry and openly sharing about what happened.  He then shared with me a story that was way more intense than mine and then he looked at me and said, ‘It’s just scar tissue. If you keep going and pushing hard you will get through whatever challenge you’re dealing with and you will look back and see that it made you stronger’.

I know with my company, the bar keeps getting raised and problems we were dealing with in the past seem trivial to what we’re working through now. However, I expect that six months from now, I’ll look back and feel the same way.

This was a reminder for me as an entrepreneur that there are going to be some really hard days but if I keep moving forward, continue learning, and constantly get better, I know that I will overcome the challenge. 

Why I Vote Republican

With the election so close and politics on everyone’s mind, I wanted to share my personal story about how I started voting Republican. I absolutely respect differences of opinion and I encourage everyone to think about why they vote the way they do.

My story starts in a college economics class. The professor wrote on the board his annual salary and tax rate. He then wrote the additional salary he would make if he taught classes over the summer and the new tax rate he would then be in based on the additional income he earned.

The result was that due to earning more income and being bumped up into a higher tax rate, he would actually lose money if he worked more over the summer. Now this made no sense to me! If he worked more, then he would make less? But it was true and therefore he did not teach classes over the summer, i.e. worked less so he could remain at the lower tax rate.

This really struck me. Why would we as a country have a system in place that punishes someone if they work harder/more? It should be the opposite I thought, where people should be encouraged to work harder.

As an entrepreneur, I work countless hours, take huge risks, and make lots of personal sacrifices. If it works out that I am successful (which the odds are strongly against any entrepreneur), how much should be taken away from me in taxes?  I think this is a fair debate but I sure don’t want to be punished for working hard and being successful.

I can sum up the difference between Republicans and Democrats in a very simple way. Democrats typically favor policies of distributing wealth. Republicans traditionally favor policies of generating wealth. Both side have good intentions along with flaws but I’d rather be on the side of generating wealth because if you don’t have any wealth in the first place, then you don’t have anything to distribute.

Pitching Cooleaf at 36|86

I had the opportunity to pitch my company, Cooleaf at this year’s 36|86 conference in Nashville. The conference is designed to highlight the best startup companies in the southeast and to connect investors and entrepreneurs. There was a $50,000 prize for the winning startup pitch along with lots of press. I have to say, the conference organizers did a really nice job and I’d recommend it to other entrepreneurs.

To be honest, I try not to do too many pitch competitions because they really don’t move the needle for your business.  It’s good to do every so often though to keep your edge. Believe me, when you have to be on stage in front of a couple hundred people and deliver a pitch describing your company, it forces you to be on point. I think it’s also good to feel that nervousness in your gut which is a reminder to me that I’m living!

The Casual Hypocrisy I See from my Democrat Friends

I’ve found that most people are very entrenched about their political views so there is no reason to get into a circuitous argument. I’m writing this piece to hopefully generate some thought and reflection.

I have friends who say they support the values of Democrats. However, based on their actions, I see them supporting these values when applied to other people and not themselves.

Take the subject of taxes as an example. I have friends who support all these ideas of the government providing free this or that but when it’s time for them to pay their taxes, they look for any way possible to weasel out of paying their share. It all sounds great until they have to pay.

Another example is on healthcare. I know people that support Obamacare but never had to experience what it’s like to deal with it for themselves because they have other coverage. I personally lost my health insurance because it did not comply with Obamacare requirements and now I pay more than double what I used to pay for health insurance.

It amazes me to hear people speak so passionately about their views only to have a double standard when it applies to themselves. I don’t have an issue with someone just because they have a different opinion than me. I respect the fact that they care enough to have a strong stance if they believe it is best for our country. The issue I have is with people who talk a lot but then don’t back it up with their own actions.