3 Huge Opportunities I’ve Said “No” To And Am Glad I Did


I’ve turned away multiple opportunities over the years and here are three that I’d like to share:

#1 Turning down a promotion, new job title, and higher salary

Before I was wearing t-shirts for a living, I had a handful of real jobs. My first “career” after college was working for a professional sports organization. I started out as a design intern, then a part-time designer, then a full-time designer, and finally had the chance to be the “Product and Design Manager” after 3 1/2 years. Oooh, check out that fancy title, it has the word “Manager” in it! But here’s the thing… I hated that job.

I didn’t hate the company, I didn’t hate the work, I didn’t hate the people (quite the opposite), but I loathed being forced into the 9-5 system. I despised the loops/hoops of management and really felt like no matter how hard I worked I was never going to get much further up the corporate ladder. Heck, I hate normal ladders, so the idea of a corporate ladder sucks twice as much!

When the meeting happened, the new title was offered, a bump in salary was offered, I decided to think it over. At the same time, I had a design company on the side (#2 opportunity) and thought this looked like the right time to put my effort towards something I owned, and stop being unhappy with my work life. Saying “No” to a raise and new job title was a difficult decision to make, but an extra $500-1,000 a month and a new job title wouldn’t change my life enough to endure being stuck in the 9-5 world.

#2 Saying “No” to a $100,000 investment

It had been about 6 months since I moved full-time to the design company I helped start with a friend. We had plenty of work, were meeting lots of great people through referrals, and even seeing some people interested in bigger partnerships.

One of those partnerships was the chance to take $100,000 from a potential investor.

While we weren’t struggling financially, anytime someone offers you money when you’re a young startup, you get excited. After a slew of emails and phone calls we realized that taking this money meant we’d lose some of our decision making power. We’d have someone we’d have to make happy. Someone who had some level of control over us. And we’d lose the feeling that we created/grew this company on our own.

It certainly wasn’t easy to turn away $100,000, but I don’t regret it for a second. Staying happy and controlling our own destiny as a company meant much more to me.

#3 Opting out of being a guest on the show Shark Tank

Probably one of the biggest decisions I made during the life of IWearYourShirt happened in 2010. The show Shark Tank was hot off its first season and casting people for season two.

I remember the date (September 7, 2010) and I remember reading the invitation email with a cheshire cat-like grin. I’d made it. This was the moment that IWearYourShirt was going to be in the spotlight. I’d make millions of dollars and everything would be perfect going forward!

Not so much.

After trading 5-10 emails and a couple phone calls with two separate people in casting, I was ready to pack my bags, fly to LA, and pitch myself to Mark Cuban and the Shark Tank crew.

Then the contract came: A 45-page document, laced with legal jargon, big words, roman numerals, and tons of things I couldn’t begin to understand (let it be known I know how to count to at least 10 in roman numerals). Lucky for me, I had a very business savvy Mom and a Grandfather who had quite a bit of experience when it comes to the law.

Almost as quickly as I was ready to sign the document, they brought up red flags throughout the contract. Different things talking about ownership of my company being taken by the TV network, terms of the deals I could potentially strike with the Sharks, and that I would become a pawn for the show, but couldn’t say anything about it anywhere. Then I also came to the realization, why did I need Shark Tank?

Back in September of 2010, two years of IWearYourShirt had already been sold, and the first quarter of 2011 was already sold out. How much money would I ask for and what would I do with it? IWearYourShirt was cashflow positive. I had tons of press on my own, businesses knocking down my door. If anything, I had more to lose being on the show than to gain.

My huge grin made it’s way into a somewhat pathetic frown. I responded to one of the casting folks thanking them for the time, but that I was going to have to pass on the opportunity.

You’d think the story ends there huh? Oh no. When you tell a TV network “No” and they’ve sought you out, they come back harder. I had, not one, not two, but three producers from the show call me. One of them was an Executive Producer (apparently) and was nice, but extremely pushy. “You need this” and “This is a once in a lifetime chance” and “You’re missing out on HUGE potential for you and your company” were familiar phrases being thrown my way. I have to admit, it was pretty cool that they were pushing so hard to get me on the show, but I soon realized, I was doomed to fail if I went on.

I had no clue what to ask for, didn’t know a thing about investment money (except my limited experience in #2 above), and sure as hell didn’t want to be made a fool of on national TV. So, after about 9 more times saying “No” they finally got the picture and gave up.

I watched season two of Shark Tank and saw people get ripped to shreds and their businesses get ripped to shreds. Can you imagine a guy who gets paid to wear t-shirts for a living standing in front of the Sharks trying to prove his business model and asking for investment money? Hah, yeah, that wouldn’t have been fun.

Don’t be afraid to say no, it may just be the best thing you ever do.