Today we’d like to introduce you to Jason Cupp.
Hi Jason, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
My journey started young and has always been about others.
As a young boy, I would organize kickball tournaments in my neighborhood, those that surrounded my childhood home. I loved bonding with people who I met through my paper route, school, family, and neighbors to collaborate in our cul-de-sac for some fun and hanging out. Kids being kids, but some of those relationships are still alive today – some 40 years later.
I’ve always had a very strong connection to my family.
Growing up, my mom owned the local hair salon, so she knew everyone in town. Everyone lined up on proms and weddings and other celebrations to have my mom and her co-workers make them prettier for a day. It was so awesome growing up seeing my mom be focused on others. It’s hard to write about her, as she passed away a little over 2 years ago. She was my best friend and throughout my entire life, she taught me to be selfless and focus on others. I’m proud to be living her legacy out in my life today.
My dad taught me a lot about business, entrepreneurship, and working really hard. Prior to retirement, he was the hardest working man I’ve ever met.
Every single morning, he would be up at 5 am to make sure our family was taken care of, had food on the table, and had a roof over our head. I’m honored to have a very strong relationship with him today – and talking to him every single day is a joy.
My brother has given me so much appreciation for everything in culinary and hospitality. For years, I never even spent one minute in the kitchen cooking anything – and now he might say I’m a better cook in some dishes than he is. Since a large part of his life was spent in the hospitality business, he always encouraged me to think of others when dining and creating memorable experiences through it for others.
In my professional career, I have loved being focused on entrepreneurship, and have learned extensively from the school of hard knocks. At the age of 13, I started mowing lawns. That didn’t stop until the market crashed in 2009 when my business failed and I lost everything. I look back on it and am grateful for that life and business misstep. I likely wouldn’t be writing these words or having the perspective that I have now if I hadn’t gone through that significant adversity.
Just a year before the economy got the best of us, our company won “Top 10 Company in Kansas City” by a local magazine. Not just the top 10 company in landscaping and design/build, but Top 10 company of all industries. I was humbled. Little did I know that just 15 months later, I’d walk out of my office for the last time and lose it all. Many think that failure is just that – failure. But, I knew I needed to find opportunity in that failure, and have that focus on being transparent about the adversity, losing it all, and then starting to rebuild.
Today, I’m doing what I always dreamed of – helping other small business owners across North America overcome those adversities and create opportunities for their maximum level of success. The “heart” payday of helping others is something I can never explain or repeat. Every day of my life, I’m grateful for every single person – client or family or friend or team member – who trusts me. Trust is the most important gift anyone can give another person. I’m truly overwhelmed in a good way with this bounty of trust.
Alright, so let’s dig a little deeper into the story – has it been an easy path overall, and if not, what were the challenges you’ve had to overcome?
Oops, got ahead of myself in the last question!
It has been a super tough road!
At a young age, my dad started a business, which ultimately failed. It really rocked our family, but I was watching from youthful eyes, and I do think that watching that and then it happening to me (after 23.5 years in business!) gave me tools I never knew I had – and I knew what I needed to overcome.
Also, when a person fails in business, sometimes friendships fail also. It taught me a LOT about how sometimes, people like other people for what they have, or what they can provide for them, rather than the relational value they have in the friendship. I lost friends when I closed my business, and that was painful. It made me focus more intently on relationships and friendships that didn’t have that trigger – and were positive in nature.
Even though these challenges, and many others, I always knew I had to do it better. I had to learn from my mistakes. I had to overcome the fear of failure. I had to put that in the rearview mirror. I had to work better. Smarter. Harder. More innovatively. I needed to make a difference in others. Continue to focus on what my mom told me all those years. When my focus pivoted to others, things blew up.
Great, so let’s talk business. Can you tell our readers more about what you do and what you think sets you apart from others?
When I failed, I had nothing, so my dad started the company I now work for. That itself has bonded us tremendously, and I’m proud of what he has allowed me to do. Now that he is retired, it’s a joy to share nuggets of what is going on in the company with him on a regular basis.
Our firm is all about small business consulting. We could have focused on larger companies or corporations, but since our history was in small business, it just made sense to invest heavily in an often-overlooked segment of business consulting. We work with 100’s of small business owners across North America – and help them overcome their own obstacles, adversities – all the while leveraging them for their maximum opportunity.
Our pillars are in several areas:
- Financial Metrics and Models to achieve maximum profitability, cash flow, and reduction of debt. This proprietary system was developed by me as I ran my design/build firm. It’s now replicated by 100’s of companies in many sectors, but mostly service industry businesses.
- HR Consulting and Compliance. Our secondary brand, Kincaide HR Solutions, helps those same small business owners be aware of often overlooked Human Resources concerns, such as handbooks, employee reviews, hiring top talent, people crises, and overall compliance to HR law and regulation.
- Kolbe Wisdom and Team Building. I’ve been a Kolbe Certified Consultant since January 2006, and have helped thousands of team members all across North America and parts of Europe to leverage their natural instincts to be the best leader and team member they can be. We also use Kolbe Wisdom, via Kolbe TeamSuccess and Kolbe RightFit, to help grow teams and make the best hires for maximum productivity and work/life balance.
- Crisis Management. Since I myself went through a lot of adversity, I love to help clients who have similar adversity navigate the course to resolution. I found that many small business owners didn’t know where to turn or felt embarrassed when something tough happened – with an employee, a vendor, a client, their bank, a lawsuit, a tax problem – and needed a trusted source to talk through it and create a plan.
- Events. Prior to COVID, we regularly hosted clients in Kansas City from across the United States for Financial Roundtables. We would teach our Financial Metrics and Models to like-minded small business owners while encouraging developing deep relationships during that time. We also have led educational events in KC and nationwide for small business owners, on a variety of topics listed above.
How do you think about happiness?
People.
Experiences.
Conversations.
Relationships.
That is the esoteric stuff. I love the feeling of a great friend, a trusted family member, a client who believes, and a person who can see the opportunity – and go after it.
Other stuff that I love: great photography and art, amazing meals and cocktails, a fantastic bottle of wine, a fast car, fun and beautiful vacations – and most importantly – raising lots of money to give back to philanthropic causes I believe in. The photo below is a group of local Kansas City friends after we raised over 100K for many charities across the US and won a fundraising award. This connection is what it is all about in life and business.
My favorite quote from the HOLSTEE MANIFESTO sums it all up for me:
“Life is about the people you meet and what you create with them. So, go out and start creating”
Contact Info:
- Email: jason@jasoncupp.com
- Website: jasoncupp.com
- Instagram: @jasoncupp
- Facebook: jasoncupp
- Twitter: @jasoncupp
Image Credits
Headshot photographed by Rob Smith Photography
