Don’t ever give up. Try something new.

Aaron McHugh

Don't ever give up. Try something new. | Aaron McHugh Work Life Play Podcast
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Jockstraps. That was my level of desperation. It was 1999 and I needed to close a deal.

It was a sales deal and I was working for an Internet startup. I sent jock straps mounted to whiteboards to five executives at a sports marketing company. Strategically attached to each crotch was my company’s logo with a succinct message, “We have the support you need!”

I’m not kidding you.

I’m laughing just writing this. I remember my CEO walking by, seeing me with my homemade assembly line, and disappointedly claiming,

“Oh, that’s what it’s come to now?”

It was during the Dot-Bomb era when our company was vaporizing every penny of our $10 million dollars in venture capital investment. We were living in the age of “build it, and they will come.” Genuinely, there was a belief that if you had cool technology, a bunch of young, energetic, smart people, a game room, stock options, bring your dog to work day, and some VC cash, someone will acquire you for “eleventy billion times” your annual revenue.

The startup wasn’t working

There we were pinning up the covers of Fast Company in our cube farm as inspiration for our future pending wealth. We were collectively working hard to bring in new clients, find uses for our innovative technology (the predecessor to web conferencing), and simultaneously outpace our cash burn rate by our growth rate of revenue.

It wasn’t working, which was why I was desperate for a win.

FedEx was scheduled to deliver each “package” by 9 a.m. Pacific Time. I logged in and refreshed my screen until I saw the “delivery confirmation.” I picked up the phone, called my prospect, and said,

Hey [Person], did you get my package?

Awwwwwkwaaardddd silence….

Yeah, we all got them.

I sent one to him, his boss, and his boss’s boss all the way up the chain.

I promised him the jocks were clean and our company was ready to support them, so let’s get this deal done.

Did my last-ditch-sales approach work?

Yes and no. My jock strap stunt forced their team to not dismiss our little company.  We were competing for their business against a much larger and seemingly stable provider. The message did get across, “We want your business and are passionate about supporting you.” We moved into the contract phase and began negotiations.

A couple weeks later, a press release was issued that they were closing their doors, selling off their assets, and letting everyone go. I called my contact and he was severely depressed, “They’re taking the furniture.” It was ugly.

Even though our contract didn’t last long, it did leave me with one burning lesson: don’t ever give up. Try something new.

Try something before you give up

I’ve always believed that if nothing is working, then try something else before you simply give up. Clearly from this story, you can tell I can be prone to taking it a little too far. I think I can help you the next time you are feeling stuck and ready to throw up your hands:

  1. Choose action over Inaction
  2. Chase Creativity over Predictability
  3. Dare to be Risky over Playing it Safe
  4. Ask for Forgiveness over Permission
  5. Pick a Fight over Surrendering

Friends, when it looks like you are down for the count, don’t ever give up. You should try something else.

I wouldn’t necessarily recommend just sending jockstraps to random people, but what’s the unorthodox, paradigm-bending leap you need to take to make an extraordinary impression for your future?

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  • I love this ingenuity!

  • James Thomas Canali

    omg! yes! Love it Aaron.

  • LC

    Encouragement for a dark day, bullseye! I’ll push on and try something different. Thanks!

    • LC-you got this. I’ll try something different myself today. I write these stories so I can be reminded of the way I want to live. Does my heart good that it helps give other people a shot in the arm. Keep going.