Meet Terry Kennedy, Founder of Appreciation Financial

Terry Kennedy

Terry Kennedy is the founder, president, and active CEO of Appreciation Financial, a full-service financial services company working in the public employee retirement niche.  Kennedy is a visionary who has overcome odds, trusted his path, and has disrupted an entire industry. Kennedy has an internal drive for success through providing opportunities and helping others.

Please tell us a little bit about your company – what is Appreciation Financial all about?

Appreciation Financial focuses on providing solutions for all areas of your life, including insurance and retirement planning. When we started this company and named it Appreciation, I knew we would need to live up to the meaning. We specialize in conservative investment strategies that add appreciation value to our client’s funds – but we also incorporated giving and showing appreciation into everything that we do. We believe in giving back to the communities that we operate in-it’s such a passion of mine! Our clients are public servants. They are educating our future leaders, pushing through government red tape to get the best outcomes possible for their communities, and even saving lives. I have a service-driven life mission to help the helpers. It feels great to help these amazing individuals.

Tell us a little bit about your background and how you started your company?

An agent met with me to go over my OWN financial goals and retirement savings. I realized that what he was doing was SO important & that not enough people plan for the future. Instead of the meeting being about me, it became me picking his brain about what he does, how he did it and how I could do it too.

What was the biggest problem you encountered with your business and how did you overcome it?

Last year, with a world-wide pandemic that caused so much uncertainty, Appreciation Financial was able to completely pivot and our agents were able to help their clients virtually from the comfort of their homes, instead of face to face as they were doing before. It was not fast – or easy. First, our leadership had to buy in and get past the uncertainty of change. Next, we had to train, motivate, and reassure our agents that this change COULD BE GOOD! We got them to realize they no longer needed to spend time and money driving to workplaces and could actually help more people without geographic limitations. We trained on asking for referrals, online reputation, and time management. We created professional Zoom backgrounds and coached agents on how to make homemade green screens so the backgrounds would look great. 

Our clients appreciated that they were still able to get their questions answered and their financial needs met, despite everything going on. Most of our target market was home and being paid without work to do so focusing on their retirement became a top priority. We also hosted a bi-weekly recruiting event via Zoom to introduce others who may have lost their job and were looking for a new career to the AF Opportunity. Appreciation Financial was able to not only remain open and in business but was also able to reach our all-time, record-breaking highs. 

What were the top mistakes you made starting your business and what did you learn from it?

If I could do it all again I wouldn’t have wasted one night of good sleep on naysayers. When I began my then-wife told me to “get a job” – even my parents disapproved of the entrepreneur lifestyle. I worried. I stressed. I never wanted to disappoint my family. I let their opinions weigh on me, however, fast forward 12 years and I’ve developed a company that has generated a dozen million-dollar earners. I’m not only taking care of my family but I’m providing opportunities for others to give their families an amazing life. I learned to trust myself and my vision – something that doesn’t come easy early on. 

How do you separate yourself from your competitors?

Simple – I believe in giving back where we do business, and I am passionate about my space. My company serves a niche – 403 b planning for public employees – it’s a niche so many insurance and retirement planning companies overlook it, however, we know it inside and out – we speak the public employee language and truly care about them. They feel it when they work with us and trust their retirement to our skilled specialists. 

What is one thing that you do daily to grow as an entrepreneur?

I read. I also love bouncing ideas off of others. My favorite thing is to ask other people I respect to “poke holes” in any new ideas. I figure if I can address any and all risks before I roll something new out to my company then I have a much better chance of it working. Some people hold new ideas close to the vest – not me – I’m always looking for feedback.

What are three books or courses you recommend for new entrepreneurs?

As they say, the difference between you now and in five years are the books you read and the people you meet. I lead a book club at our corporate office where I encourage my staff to read personal development books. We meet weekly to discuss the chapters, set goals, and hold each other accountable.

We’re currently reading “The 21 Irrefutable Laws of Leadership” by John C. Maxwell. Last year I published a book along with our President of Sales, Don Spini. The book is called “This Changes Everything” and it is about a game-changing way to make more money and can be applied to almost any industry. The book became an Amazon Best Seller.

What is the one thing you wish you knew before starting your business?

Success happens after a long pattern of hard work and laying a foundation – you must have patience. 

What has been your most effective marketing strategy to grow your business?

It took me years to trust my system. Meaning – stop trying to recreate marketing and sales techniques. Our business is simple – we help the helpers – I tried every way possible to get to public employees – I know what works and what does not, but every so often I’d have someone come alone and promise they had a better way of doing what I’ve been doing for 18 years. It ALWAYS fails. I know now to trust my system, teach my system, and stop letting people attempt to get me to deviate from it. 

If you only had $1000 dollars to start a new business, knowing everything you know now, how would you spend it?

I tell anyone to pay for an online class and study for an insurance license then sign up with my company. We’ll coach you up to be a million-dollar earner too. 

What’s your best piece of advice for aspiring and new entrepreneurs?

Being an entrepreneur can be lonely. It takes bravery to face the social and relationship challenges that comes along with it. They do not teach this in textbooks. I’m not even sure if it is possible to create a curriculum that can prepare people for true entrepreneurship. The key is finding mentors and reading the memoirs of highly successful people. That’s where the real-life side of entrepreneurship is taught.

What is your favorite quote?

Always look for the win-win. I use it in every decision that I make. Too often people think being successful equates to finding ways to benefit yourself. No one wins alone. I believe that the definition of success is when you achieve goals together with the people you are in business with. In fact, I use this everywhere in life – not just in business. 

Random Bonus: With the game on the line and 5 seconds on the clock, who takes the last shot? Michael Jordan, Kobe Bryant, or Lebron James? 

Jordan – always go with the legend. Experience plus the pure physical intuition and confidence of so many similar shots under his belt poises him for the win. 

How can we get in touch with you?

I recently launched a new lifestyle website for people to follow along with me. You can check it out at

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