How I lost $50K in Pants

I blame Derek Dooley for my decision to go into the pants business. If he hadn’t started wearing the orange pants on the sideline I doubt that I would have decided that SEC colored pants was a gold mine. I mean, sure, I already had my own UT orange pants — purchased in 2007 — but it was Dooley on the sideline that convinced me Outkick could sell thousands of pairs of pants in SEC colors. 

Of course, I didn’t know anything about pants. (In fact, on most days I don’t even wear pants). Or fashion in general, for that matter. And that should have been a warning sign when it came to my decision to go into the pants business. But if a market exists and you can reach that market, how much advance knowledge do you need?

Plus, I’ve spent the past decade defying the odds on every decision I’ve made. I’ve sold tens of thousands of sports books and most sports fans are borderline illiterate. I took a nonexistent website to millions of unique readers a month, in the process selling thousands of tshirts to Outkick fans. Hell, I even turned a law degree into a multi-million dollar career as a “sportswriter,” had the top ranked radio show in the nation, and even managed to host my own weekly television show. 

Compared to these accomplishments, how hard could it be to sell pants? I mean, everyone has to wear pants, right? How could I not sell pants?

So the first decision we had to make was: what kind of pants would we sell? Easy, popular pants. We went to Vineyard Vines and got a pair of their khaki pants. They sell their pants for $120 and they cost around $10 to make. So why not sell our pants, which would be the same quality and material as Vineyard Vines, in SEC colors for half that price?

Bang, I was going to be pants zillionaire. 

So it came to pass that before long I had a business partner — with the requisite pants expertise — and we were scrutinizing the colors on sample pants laid out on my living room table that we’d dyed in China. Yes, we were going to make our pants in China and ship them over on a barge. This all seemed perfectly normal. I was so enamored of our profit margins that I didn’t even stop and think, “Clay, why are you making pants in China?”

We had three orange colors — Tennessee orange, Auburn orange and Texas orange — and it was important to make sure that all three looked different and looked like the right color. After all, using the correct PMS color to dye the pants didn’t mean they would still look right once the pants were colored. College football fans care if their pants aren’t the right color, so we ensured that they were the right color. We did this by asking my wife to get involved since I’m pretty sure I’m partially colorblind.

The only thing worse than going into the pants business is getting your wife involved in your pants business.

It turns out there are a ton of decisions to make in the pants business. And I was already involved in the Internet, radio and TV businesses. Plus, an online lawyer’s CLE company, Outkick your CLEs, and sundry other travel and speaking engagements. I wasn’t a businessman, I was the business, man, which meant I was always running around like an insane fool.

So my wife was always asking me questions like, “How many Kentucky blue pairs of pants do you think we should order compared to North Carolina blue?”

And, of course, I had no idea.  

Next we had to decide what waist and pant lengths to order and how many of each to order. 

And this should have been a warning sign too. 

Because unlike shirts, which pretty much everyone knows their size on, pants are a sizing disaster. Because everyone who makes pants lies about what the pants waist size is because companies all mark their waists lower than they actually measure to make Americans feel less fat. For instance, I’m a 34 waist and a 32 length. But when I’m actually measured I’m closer to a 36 waist. So if you’ve ever wondered how you can be the same size for a decade and every pair of pants fits you differently, this is the reason, because every pants company sets its own sizing scale. And they’re all scaled to make you less fat.  

I decided, after a legitimate argument with my wife who wanted us to be the only pants in America that were sized honestly, that we would inflate our waist sizes by one inch. That is, our 34’s would really be 35’s and so on. Then we had to decide how big and how small our waist orders would be and how to distribute the pant size orders.

Are you fucking kidding me?

We went as low as 28 waists and as high as 48 waists, in case someone wanted to buy pants that also doubled as a tent.

A 48 pant!

Why did we do this? Because since I sit on the iron throne of inclusiveness and I’m the King of Tolerance, I didn’t want to fat shame. (Even though, truth be told, I considered the final option on our waist scale online just saying, “You’re too fat for our pants.”)

We have still not sold a single pair of 48 waist pants.  

Next we had to deal with pant lengths.

The problem is, as you can rapidly see, if you trim the pants to a specific length, you’re minimizing your audience really quickly. And you might be stuck with pants that are totally unsaleable. How many 48-34s are there in America?

So we decided the pants would arrive from China without being hemmed.

But we would offer hemming on the pants for an additional charge if people wanted the hemming. (And who the hell wouldn’t want the hemming? The only person I’ve ever known who could hem pants was my grandma and she’s been dead for a decade. If you gave me pants and told me to get them hemmed, I would have no idea what to do. I’m not even kidding about this, truly zero idea.)

Next we had to decide how many total pairs of pants to order. 

And if we dyed our pants in batches of 500 they were cheaper. So I decided we should order 3500 pairs of Chinese pants of varying colors. We eventually decided on ten pairs of pants in virtually every SEC team color.

So I cut a $50,000 check for 3500 pairs of Chinese pants.

Our price point was around $15 after shipping was factored in and we’d sell the pants for $60. All we needed to sell was a thousand pants and I’d get my money back. Sell out all 3500 pairs and we’d make several hundred thousand dollars.

This was going to be so easy.

What was our marketing strategy? Me Tweeting about pants.

That was it.

My wife and business partner both said we needed a more aggressive marketing strategy, but I was convinced that all I would have to do was Tweet about pants and we’d sell thousands of pants. Again, I’d sold everything through Twitter, why not pants?

At this point I should actually point out that no one I told about my pants idea thought it was a bad idea. In fact, several people wanted to invest in my pants business because they were convinced that SEC colored pants would all sell out in a heartbeat too. If I’d been an astute businessman I could have sold shares in my pant business and gotten out with a profit before we ever sold a single pair. But I was convinced I was on to a goldmine. And, if we ended up losing money, I didn’t want to lose any money for anyone else. But, mostly, it was that I wanted all the money for myself. 

So after a shipping delay necessitated by a typhoon in the Pacific Ocean, the pants arrive.

And they are pretty fucking fantastic looking pants.

Still are.

But the problem with 3500 pairs of pants is they take up a lot of fucking space. So we rent space in a warehouse where the pants will be drop shipped when the orders arrive. We build a website for the pants and Outkick Gear and sometime in the summer of 2013, we officially go live with the pants. I remember Tweeting out the link to the pants from Tennessee Titans practice.

We sell eight pairs of pants the first day.

That’s not ideal, I’d been hoping for hundreds, but I convince myself it will all work out.

It does not all work out.

Presently, over the past three years and change, we have sold 1200 pairs of pants.

After the first year, I fired my wife from the pants business because she kept asking me too many questions about pants. 

After the second year, we dropped the price on the pants to $20 a pair and my wife and I went to see Hannibal Buress’s comedy set in downtown Nashville.

I swear to god, one of the punch lines of his comedy routine about his growing profile as a comedian and how to make better financial decisions is, “I mean, it’s not like I decided to go into the pants business.”

My wife elbows me and stares at me as the audience roars in laughter around us.

I do not make eye contact. 

After the third year, I bought a house from a guy who has multiple clothing retail stores all over Nashville. As part of the deal to buy his house he agreed to help us sell pants by putting them in his store. (I’m not kidding about this. I’m the only person to ever buy a seven figure house and include pants as part of the deal.) Over the past year the pants have not sold in his stores either. Which, to be honest, made me feel better. If a professional clothing retailer can’t sell our pants, maybe no one can. 

Except me. 

I managed to sell over a thousand pairs of pants. 

Which is potentially the greatest achievement of my adult life. 

But this means we still have 2200 pairs of pants left.

We now pay $1k a month to store the pants in the warehouse.

I told my wife that we were going to move them into the house last summer to save money and she lost her mind. “Do you know how much space 2000 pairs of pants take up?!”

She then went to the warehouse and took a series of photos of our pants in boxes and then sent them back to me one by one via text message. 

Turns out, 2000 pants take up several thousand square feet of space.

So the pants are still in the warehouse and whenever I have a decision to make money she says, “You mean, like the pants?”

This past April my accountant was doing our Outkick tax returns and he called me. “I’m sorry,” he said, “but this math can’t be right. You’ve lost $50,000 in pants?”

“No,” I said, “that math is right.”

Our pants are $20 and they are the best deal on the Internet right now if you’re an SEC football fan, but I am so ready to get out of the pants business that I’m prepared to give them away to a worthy charity.

Ideally, I’d like to give them away to the troops.

Why?

Because then I can truly say I support the troops more than anyone else. If I’ve learned anything in life, it’s that you can turn any failure into a success if you support the troops in the process. So if you’re at Ft. Campbell and want to give my pants to the troops, contact me.

In the meantime, I’ll be here nursing my pants losses.

Fortunately, it’s college football season and I’ll be able to win back all the money I lost in pants gambling on football this season.

After all, if the pants business taught me anything at all, it’s this: the only way to get out of a hole? Keep digging.   

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