How I Created A 6 Figure Coaching Business By Accident That Then Blew Up In My Face (And So Can You!)

Brendan Cahill
19 min readMay 12, 2020

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I have a set of skills, a very particular set of skills… — Liam Nielsen Taken

If you’re reading this, it’s likely you want more in your life. Maybe you are a high school or college athlete looking to turn your love of sport into a business. Maybe you are stuck at a 9 to 5 you have fallen out of love with and you are looking for excitement. Or, maybe you are even further up the road than I looking for your next big thing after you retire. Whoever you are, wherever you are, and whatever you are you are looking for more, and you’re looking to start something.

My greatest hope is that this piece is not only a cautionary tale in what happens when you cross an idiot with modest accidental business success, but also as a rough blueprint for how you might, too, also start your own journey — albeit hopefully without the having your business blow up in your face part.

Enjoy!

Like Liam Nielsen I too possess a very particular set of skills (although not his brogue). I know how to coach kickers, punters and snappers at the high school, college and professional level. And, it was this particular skill that launched my accidental 6 figure coaching business (that then imploded).

I had been a former college football player at a small division three school with some decent success punting and kicking. Though I never won many accolades, I thoroughly loved the experience and just fell in love with kicking and punting. There’s just something so satisfying about looking at a ball and then kicking it to make it go high, far and straight.

After college I did Peace Corps in Ukraine for two years, and then came back to find myself teaching at an urban charter school that (shall remain nameless). While I was psyched about helping to “change lives”, I was growing disillusioned with the philosophy, tactics and growing disparity between the mission statement of the school versus its practices.

It wasn’t a normal day unless I had broken up a few fights, was cursed at, or the cops were called. I was burnt out and needed some way to de-stress. Enter kicking.

I had seen a few other “kicking coaches’“ out there on the internet making 6 or even 7 figures training and holding kicking ranking camps (yes it’s a weird thing I agree — imagine Tiger Kings, but just kickers. You get the picture…) and figured I could see if there were any kids in the area who might want to train. I was getting serious with my then fiance and maybe this would be a nice way to make some gas money.

My first clients had come when my old trainer agreed to put my name on his website (Thanks Lee McDonald!) as a kicking coach in New England. He was having families drive all the way from Rhode Island to Southern New Jersey (I know, yew NJ) and it might make sense for them to work with someone closer. Soon, word began to spread in my area of CT that there was a decent kicking coach. One turned to three, three to six, six to twelve and pretty soon I was training anywhere from 20 to 30 clients a week.

As things began to tank more at my high school, I poured myself more and more into the coaching. I remember there was one weekend that first summer of 2016 where I made $400.00 and thought, hmm there really might be something here! I doubled down on my business scaling, got creative and read nearly 50 business books in a span of about a year and applied everything I could — basically throwing spaghetti at the wall and seeing what sticked. Pretty soon, the results were staggering to me…

  • Year 1: $4,000 Revenue
  • Year 2: $40,000 Revenue
  • Year 3: $140,000 Revenue

Here I was thinking this was just gas money!

It was also extremely rewarding helping young football players not only improve at their position, but also develop confidence and feel great about themselves. Parents and coaches too were pleased with their players’ results on the field. Word of mouth (the best kind of advertising) continued to bring in a steady stream of 1–2 qualified long term clients a week.

But, right between year two and three I started to lose my way…

While the bank account was flush, my personal relationships were becoming bankrupt. I was justifying selfishness as selflessness saying things to my wife (and self) like: I’m doing this for us. Think of what we could do with a little extra money coming in! You just don’t get it. Why are you more supportive? Aren’t you proud of me? I had essentially begun to equate my personal self-worth with the performance of my business. When it went well, I was doing well. When it was doing poorly, I was doing poorly.

To only compound these preexisting problems, I still struggled mightily with self-confidence. I felt insecure about coaching players at continually higher and higher levels who far exceeded my own abilities when I was their age. I felt my coaching was not good enough to stand on its own and I should bring on a business partner with some professional kicking experience. It turned out, at the time, one of my good friends seemed to fit the bill. Having a good friend as a business partner — what could go wrong?

Things seemed to be going OK the first few months of our business partnership: We began to expand kicking coaching operations into various geographic regions of the country. Our brand recognition was growing quite a bit among not only players but now college and notable high school programs knew of us and sought out our opinion on various kickers. Revenue too, also continue to climb. My business partner was no doubt a great coach, an expert at his technical craft and was able to build strong relationships with players.

But, all was not well.

Already under personal strain by how much time I was investing into the business, I began to feel uneasy about our partnership. While we got along as friends, we had never discussed in detail how things like compensation, decision making, and dispute settling would work on the off chance a dispute between friends might arise. I had continued to bring in the bulk of the company’s revenue for the while my partner’s operations were bringing in less, yet we were both paying ourselves 50% of income. In a way I was financing my business partner’s compensation. This was particularly frustrating for me because, remember, I was sacrificing time from my family using the justification that money brought it would make it all worth it. Not so.

To even further damage my credibility, I had told my day job that I was not going to be returning to devote my full time to my “passion” (my gosh I was to vomit just typing that). I told everyone. I was almost smug about it. Look at these fools! Shackled to their day jobs! Not confident enough to take the risks necessary for true financial and personal freedom! Blah. Blah. Blah. Oh boy, was God setting me up for a MASSIVE HUMBLING.

Things finally came to a head at the start of Summer 2019 when I told my business partner, while I respected him as a friend, this business partnership was not working and I wanted out. I’m not exactly proud of how I did it. I sent it electronically instead of speaking in person. Looking back, I should have had an in person conversation, but sitting my own shoes back then, I had never dissolved a business partnership before and figured it would be a good idea to document everything. Plus, I didn’t trust myself to lay out logically my justification for dissolution over the phone or in person. I mean, how many ways can you essentially say you’re a good guy but a bad business partner?

Justifiably so, my business partner was upset. What I thought might take only a few weeks of discussion turned into almost six months of long, excruciatingly tedious back and forth emailing, lawyers and legal jargon which I don’t care to dive into. I have a mentor, Jay Stolfi who owns a successful manufacturing plant and he had a good take on it, “Lawyers basically get everyone to do what they knew they should have done in the first place, but for $10,000’s.” Eventually, after 6 months of back and forth haggling, I sold my 50% of the company and was done with it.

My old business partner is a great guy, and even better coach whose running a successful business of his own these days and likely with many less headaches coming from me. Things ended about as amicably as one could reasonably expect. When you close out a business, there’s no clear “business dissolved date” as you still need to untangle various legalities that may take 3, 6, or even 12 months to play out like taxes, registrations, and transferring ownership of various assets.

So, within a span of about 6 months I went from being an inch away from leaving my day job to coach full time, to losing it all in a spectacular fire ball that was a humbling the equivalent of a 2x4 smashing my face repeatedly.

So let’s recap:

  • Spring 2016 started side hustle kicking coaching for gas money.
  • Spring 2017 revenue topped $4,000.00 and I tell myself I think I might have something!
  • Spring 2018 revenue topped $40,000, I spend less time with wife, personal strain increases as revenue increases, and I make an unqualified insecure decision to bring on my good friend as a business partner.
  • Spring 2019 revenue topped $140,000, my wife hates me, my good friend business partner hates me, no embroiled in long drawn out legal battle, my business is now in tatters.

So, where did we go wrong? (And, maybe if I’m done being sad, Where did we go right?)

I created a job, not a business

Most 9 to 5’ers who are trying jump from their day job into a full time business simply recreate the drudgery of their day job in their business. I was spending significantly more time on this business than I was in my own 9 to 5 job. As a coaching business, not only did I have to make calls, generate leads and facilitate sales, but I also had to render services in person at a set physical location and time. Since you can’t train high school kids during the day, my training hours became 3pm to 7pm during the weekdays and Saturday and Sundays, spending sometime days 7am to 7pm. This time, of course, was the only time my wife and I would have set aside for ourselves to actually, you know, be a couple.

Essentially, I was trading time for dollars. It was a totally not scalable business model since every product and service required an extremely high amount of time for me to deliver. I was unaware of

I did business with a friend

I love Michael Scott in the The Office, but his tragic flaw is that he desperately wants to be liked and be friends with his employees and company administration. In the book Predictably Irrational Dan Airely one of my favorite chapters discusses the difference between social norms and business norms. If a friend asks you to help them move the sofa next weekend, you’d likely do it no questions asked, and certainly for no money. But, if that same friend asks you to move the sofa and then says “I’ll pay you $25/hr”, the context of the request changes. When the context of a request changes, the nature of a relationship also changes. Next time your friend asks you for help, what are you going to expect? Money.

Just because you are friends in a social setting doesn’t mean you are automatically going to hit it off as business partners. While everyone lauds Steve Jobs, most forget he could be a bastard at times and was booted out of Apple in the 90’s because of it. Joe Biden and Obama aren’t playing golf anymore either. And even Warren Buffet and his long time advisor Charles Munger get in various spats from time to time. While conflict isn’t always bad (shoot my wife and I have had more constructive arguments than I care to remember…!) it can be without a roadmap for how to handle them.

We had never decided on what to do in case there was a disagreement. After all, the newly wed couple never thinks about divorce right after the wedding. Gary Keller, author of The One Thing, jokingly calls Article Of Agreement that you’re supposed to file with states when you start a company “Articles Of Disagreement” since you are only going to use them when something goes wrong. While I am morally against prenups prior to marriage, I am now, no longer, against it in business.

At some point, something is definitely going to go wrong and when it does, you need a plan for how to navigate it. When our issues of ownership, control and revenue sharing arose, we were stuck in legal no man’s land because ownership was a split even 50/50. Any lawyer that looked at this situation laughed at how comically juvenile this was.

I now will never sign a piece of paper without really reading all the fine print. I also will never be a part of another 50/50 partnership. There simply needs to be one chief in the village. Someone has to call the shots and be an executive. I also will not accept disproportionate compensation.

I needed the business for self-worth

I blurred the line between self-worth and business worth. When the business was doing well, I was personally doing well. I loved to justify selfishly spending hours and hours away from my family by saying “it’s for us” when really I just cared about myself. It was a pure ego trip.

I remember my wife telling me one day: Look, I don’t care how much money you make. I care about you being happy and you being present — here. That’s it you IDIOT! (the idiot was thrown in by me for dramatic effect).

I didn’t realize it at the time, but I was just trying to feel like I had confidence and self-worth and thought the business was how I was going to give it to myself. But the reality is confidence isn’t something anyone, anything, or any success can give you. It is a belief in your own intrinsic value as a Son or Daughter of God that says no one is any bigger, better or more important than you and the greatest gift you can give another is simply being who you are.

BOY! That realization would have saved me a few years of head aches. But, God is an ironic Being.

I did things for the money

Just because you can, does it mean you should?

I found out I was pretty good at sales — way better than I expected to be. I was selling training packages, camps and services left and right. Why? Because of course MORE money is better! Bigger events! Bigger advertising! Bigger bank account! False.

Revenue is not income. It turns out there are taxes! And, you definitely need to pay them. It also turns out, that money without a mission is quickly lost — I was spending money on necessary equipment, media, advertising, and costs that did not need to made. I also wasn’t keeping track of how many taxes I exactly owed (my business partner, however was quite good at this). My strategy for handling expenses and taxes was simply to keep selling MORE.

I created an unscalable monster

And, while I feel clients were genuinely getting better and improving, my quality of instruction was suffering. I was selling time-for-dollars (TFD).

It turns out you need to render any service you sell! So while you can be excited at generating $13,000 in a month of revenue, you also just booked 80 hours of training at a physical location, at a set time and during off hours.

Positive cash flow with a negative personal balance isn’t victory — it’s STUPIDITY.

I tried to create demand instead of answering the calls for help.

It is not uncommon in the private coaching industry for student-athletes trying to play in college to have a series of ranking or combine camps where everyone gathers together from the same sport to compete in some contrived make-believe competitions, and then camp organizers rank players’ abilities by awarding them stars — 5 for the best and 1 for the worst (yet no one manages to get below a 3.5 star at these events curiously enough, but that is a tale for another day…).

It also makes greater sense from a business model to create as unbalanced a coach to camper ratio as possible. Remember, with any in-person service you are trading time-for-dollars (TFD). So, bring 100 campers paying $500 each to a single field, for a single 6 hour event run by only 5 coaches, and you are immediately able to generate exponentially more money than by doing individual or small group sessions.

But, just because I could did it mean I should…?

I secretly hated these types of camps. But, went on to promote my own weak version of them. While some went OK, they just ended up creating even more headaches for me. There were at least 5 other ranking camp operations in the country all serving the same old wine but in new bottles. The market didn’t want me doing another one.

Jay Abraham, business author, likes to say

“We don’t get to decide what the market wants. We have the privilege of serving the market and seeing what it responds best to.”

I created exceptions for clients.

In the drive to boost revenue I made exceptions to train clients who were not the type of clients I wanted to train, nor did they possess the attitude that I wanted my business to represent.

They were not humble. They were egotistical. They put down other clients I trained of lesser ability. They also were dramatic and created problems.

The clients who were good fits lost respect for me as I allowed cancerous personalities into training sessions. And, the problematic clients lost respect for me too as I made weak attempts to reel in their personalities.

I lost clients. I lost money. And, I lost sleep (not to mention hair!).

A great mentor I had once said:

“When you do for one you do for all. If you don’t like what a player is doing, you better deal with it quickly, and deal with it the same way for everyone.”

I didn’t though. Remember, my business was my self-worth. I was here to change lives! But, it was ultimately a losing battle. This is when I learned you haven’t been in business until you’ve had to fire a client, even if they’re paying you.

From these problematic clients’ perspectives, I wouldn’t blame them for wanting to work with a different coach. Who would have respect for a coach whose obvious sense of self respect was so tied into his business, who was inconsistent client to client and seemed more concerned with growing a brand than protecting his culture?

Now, I just refer clients who aren’t best fits to all my competitors. You’re welcome.

I got lazy (or burnt out)

My only unique selling proposition was geographic.

Until me, there had not been any serious “kicking coaches” in the New England Area making an honest attempt at full time training.

If your only competitive advantage is geographic, you don’t have a competitive advantage. People who are your customers because you are “the only…” [insert profession here] in an area aren’t yours indefinitely. Just because you have sold something once to a client, it does not mean you have won their loyalty for life.

As other kicking coaches began to see a viable market in this area of the country, I began to bleed clients who probably weren’t best fits to these new coaches.

I had never really sat down and thought about why did people even buy from me in the first place — I had no “Unique Selling Proposition” (USP). I was simply barreling ahead at 1,000mph.

Things I DID Learn…

I suppose it wasn’t all awful…

I discovered I can sell.

If you need one skill to get any business off the ground it is the ability to sell. While yes, I could have been more sincere during periods of my first business, I knew how to help people feel listened to, ask great questions and help build trust between myself and them.

Sales isn’t about convincing people to buy what they don’t want. It is about helping them get more of what they already want. Really, true sales is about giving, not getting. The more I focused on giving value to my clients, the more I generally generated in revenue. If you have no cash, you got no business being in business.

I discovered I can network.

It was the Summer of 2018 and I found myself on a football field with two of my heroes growing up — NFL Super Bowl Kickers and Legends, John Carney and Stephen Gostkowski. It felt like a dream. How?

Networking.

Networking is simply another word for sales. You are helping others get what they want and bring value to them. While I might not have the coaching expertise to “coach” a guy like John Carney, I did have a clientele in New England that would be valuable in helping him build his own Summer kicking camp operation.

Me, pumped to hang out with NFL guys, of course offered up my client list to him! He gained access to my HS client network and I gained access to his NFL network. Quid Pro Quo.

How did I even connect with John in the first place?

A now good friend, Zac Triner, who is the current NFL Bucs Long Snapper randomly reached out to me on social media after having been cut my the NY Jets looking for a way to help coach and continue to train. We grew our friendship to the point where he knew John was looking for help with camp and connected me.

Long story short, everyone you know knows about 250 people in their network. When you do a genuine job at bringing value to a person, odds are that they may tell at least a few of their 250 member networks of you who too might be interested in connecting.

There are infinite combinations of a business’s assets, skills, knowledge and relationships that can lend itself to all sorts of hidden valuable possibilities.

I discovered my backbone.

A mentor of mine, Dr. Bob Rotella who is one of the world’s most famous golf sports psychologists once told me,

“I don’t care what you do: Half the world is going to love you and half the world is going to hate you. But at least they’ll all be talking about you!”

It’s impossible to experience success without having detractors and the quickest way to make everyone mad at you is trying to keep everyone happy.

I am a pleaser by nature. But, after a few beatinngs by clients, I am now OK with forsaking short term profit in favor of long term peace of mind. It isn’t even really short term profit anyway once you begin to calculate the amount of money and time you may lose by keeping a cancerous client within your business.

I’m OK with firing clients now.

I discovered I didn’t need permission.

The term “expert” is a relative in relation to those you are trying to help. To a middle/high school/college athlete compared to me, a former D3 punter/kicker, I was an expert. Compared to an NFL Super Bowl Kicker, I was not.

You don’t need to know everything. You just need to be a few pages ahead of whoever you are trying to help.

A lot of 9 to 5’ers looking to start side-hustles or businesses get hung up here, and it’s not totally their fault. Education has programmed us to be compliant instead of confident for 16–20+ years of government mandated study. Think about all the things you need someone else to grant you permission to do in school:

  • Answer a question.
  • Ask a question.
  • When to sit.
  • When to stand.
  • What side of the hallway to walk on.
  • When to get a drink of water.
  • When to go to the bathroom.
  • How to format a paper.
  • How to write a paper.
  • How to speak to adults.
  • How to write.
  • How and when you can use technology.
  • How and when you can look at your phone.

It turns out confident, inquisitive and self-reliant students are often the most threatening to the power structure of schools and are subsequently the most punished.

Don’t you ever find it ironic that Ivy League schools continually book key-note graduation speakers who FLUNKED OUT OF THEIR SCHOOL to speak and inspire the platoon of graduates who just finished?

If you can make it through almost two decades of school with any entrepreneurial fire left in your belly, it is a modern-day miracle.

How do you start? Well, that is the subject of an entirely different article, but when people ask me I just say: I created a Twitter account, bought a bag of balls and made a phone call.

It’s really THAT EASY to start a business.

I discovered what really matters.

Making a business should make you a better person for your wife, family, friends and community. If it is making your a worse person, it doesn’t really matter how big your bank account it, what famous person you might know or how many of your social media posts go viral.

What’s even cooler about a business is that YOU get to make the rules.

Don’t like doing in-person services? You can make a shippable product. Don’t like advertising online? You can use just a really good referral program. Don’t like social media? Outsource it to a virtual assistant (VA).

Derek Sivers, an entrepreneur and author of the book Anything You Want once said,

“A business is your own little utopia and a great way to make the world a better place”. You make the rules, not your clients, nor a “silent jury who you are trying to impress”.

In summary here’s what matter:

Is my wife happy?

Am I happy? (Automatically when my wife is!)

Are our bills paid? (Takes less than you think!)

In closing…

Success, money or accolades will only make you more or less of what you ALREADY ARE.

Whether you are a millionaire, or a pauper, you are still the same person that you will see in the mirror every morning and night. No one can make you OK with who or what you see in that mirror except you.

A business, then by extension, is also just an amplifier of who you already are.

At the end of the first Harry Potter Book, The Sorcerer’s Stone as Harry Potter is looking at the Mirror of Erised (which only reveals what you truly desire in its reflection)

Let me explain. The happiest man on earth would be able to use the Mirror of Erised like a normal mirror, that is, he would look into it and see himself exactly as he is.

While I’m not quite there yet (I don’t know if anyone truly is all the way there) I am a lot closer to seeing simply myself in that mirror and being cool with it — that is despite the balding.

Brendan

I write about becoming my own brand and how to monetize it on the way to financial independence. If you enjoyed this, I’m most active on Twitter and would enjoy following you back — follow me here.

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Brendan Cahill
Brendan Cahill

Written by Brendan Cahill

Exploring emerging trends in teaching, education, tech, business and beyond.

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