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6 things I’ve learned running my own business for 6 years

Knuckleball Comedy was officially born on August 30th, 2016 which means a few months ago we celebrated our 6 year anniversary. If you had told me 10 years ago I’d be running this business I would have been speechless. I wouldn’t have laughed or thought it was silly, it was just so far away from what I thought I might be doing that I wouldn’t know what to do or say.

But here I am, 6 years into the Knuckleball Comedy journey and ready for more. I started by teaching one improv comedy after school class for a group of 12 kids at the elementary school I attended. From there all of a sudden we were in 15 schools, 20 summer camps, we performed at birthday parties and I needed to hire instructors to teach classes. It was all exciting and it all happened so fast.

(One of Knuckleball Comedy's first school programs at a local elementary school in Chicago in 2017)

6 years later and everything about the business looks different. We still run improv comedy programs in schools - teaching kids how to better their communication skills and confidence while thinking quickly and creatively. And we still run summer camps and perform for kids' birthday parties. We work with 100s of kids every week and are still growing every year. But I am much more hands off for most of that.

Now I spend most of my day growing the corporate side of the business. We specialize in running incredibly fun and interactive team building, professional development and leadership workshops for all types of businesses. All of our workshops include customized improv comedy activities aimed at building a workplace culture of support, creativity, and amazing active listening. Of course most importantly, our goal is for everyone to laugh and have a great time.

In fact, as I type this I am on a plane from Chicago to Boston to run a super fun team building workshop for some folks at Fidelity Investments. If you had asked me 10 years ago if I thought I’d be traveling around the country facilitating fun team building events for giant companies I would have said, “What!?” I literally wouldn’t have even understood what you were saying.

But here I am. And the truth is I can’t wait to wake up tomorrow, put on my fancy clothes and go to the fancy hotel, have the microphone hooked up to my lapel and stand in front of 75 business people to make them laugh and watch them interact with each other in such a fun way they never thought possible.

I have learned so many things over the last 6 plus years. Here are 6 that stand out to me right now.

1. Try to celebrate the wins

I wake up everyday with the exact same question, “how can I gain more clients and grow my business?” Some clients come in through my website and book after our first conversation, others I spend months even years connecting and reconnecting with until they are finally ready to book an event.

When I do book an event, you’d think I’d spend time celebrating this victory. After all, it was extremely hard to achieve. Instead I am excited for exactly 5 seconds before asking myself the same question, “how can I gain more clients and grow my business?”

But as I type this I am trying more and more to be really happy after I complete a sale. And not just that, but sometimes I look back to 6 years ago and I try to be happy with what I’ve created so far. I use the word “try” because it’s hard to not always be thinking about the next one. But it helps me enjoy my work when I let myself be happy when something good happens.

So do your best to celebrate the wins, I promise it helps.

2. Don’t start a business unless you are obsessed

Starting a business is not for everyone and there is no shame in that. There are many different jobs out there that could fulfill you and so many that you should be very proud to have. If you enjoy neverending uncertainty, being kicked while you’re down and having people constantly saying “no” to you, then starting a business might be for you.

But in order to withstand the bad things in order to potentially receive the good things - growth, success etc. you have to be obsessed. If you have an idea but you’re not obsessed with it, just find a regular job.

3. Just do it

I spend hours every week reading about how to improve my SEO, sales outreach, marketing strategies, blogs, Linkedin posts and more. It’s important to read and always continue learning, but at some point, you have to just do it.

You have to start reaching out to prospects even if your sales strategy isn’t perfect. You have to actually submit and publish your blogs and Linkedin posts even though they aren’t perfect. You can continue to learn how to improve, but ultimately, you have to go out and do it. Don’t wait another day, just do it and continue to learn as you go.

4. Don’t undervalue what you do

The first professional development workshop I ran was in 2017 and I charged a hilariously little amount for it. I tried to charge something a bit more (still incredibly low) but they said they “couldn’t” afford it. I had never done one before and I was desperate so of course I went down in price.

After I learned and grew as a business person I realized that a little negotiation was ok, but I had to hold firm on my price range. After all, as I sit here now in 2022, I’ve facilitated 100s of team building and professional development workshops.

I am a professional and it has taken me over 6 years to develop the amazing programs that I run for businesses.

Right now, my prices aren’t expensive and they aren’t cheap, they are exactly what they should be for the amazing value we provide. Whatever you are selling, that’s exactly how you should feel, not expensive, not cheap, but right at the value you are providing.

Figure out how much the value you are providing is worth and don’t charge less than that. If people want your amazing product or service, they need to pay you what it’s worth.

5. One thing at a time

Whether you are a business owner or not, you likely have a million things on your plate. It can be overwhelming because you don’t know where to begin.

Sometimes when I am overwhelmed with the million things I have to do, instead of doing those things, I just do nothing. I panic, curl up into a ball, grab a snack, walk around my office and do everything I can to not do any work.

Of course this doesn’t help anybody. So when I feel overwhelmed, which is basically every single day, I try my best to take a breath, stay calm, and tell myself, “one thing at a time.” That’s all anyone can do. If it helps, sometimes I take care of the easy stuff first. Just to get the ball rolling with knocking stuff off of my to-do list.

One. Thing. At. A. Time.

6. Ask the internet

I honestly don’t know how people figured anything out before the internet was a never ending mountain of infinite information about every single thing on earth. But I don’t have to know how previous generations figured things out, what I know now is that everything is on the internet.

Like every other entrepreneur, when I started my business I had no idea how to do anything. I didn’t know anything about building a website, marketing, sales, newsletters and everything else that goes into a business. So every step along the way I watched youtube videos and read blogs or even just looked at what my competitors were doing. And I still do that today.

If I am struggling with something or want to improve something, I read blogs and watch videos. Then I do my best to try and implement. That doesn’t mean it’s all going to work - of course it’s not that easy. But you learn something, you implement, it doesn’t work, then you rinse and repeat until you find what does work.

But you’re not the first person to need help with that thing you are struggling with. Someone else had the same problem and they put it on the internet.


Looking forward to writing this same article in August of 2023 with the new things I’ve learned and with all of the growth my business will hopefully have achieved.

Until then, if you are interested in bringing your team closer together while enhancing their active listening, communication and creative thinking skills - all while laughing together, then check out some more information about our team building and professional development programs HERE.

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