How to Raise $1500 by Selling Ad Space on a T-Shirt

East Stroudsburg Winters
Baby, it’s cold outside

It’s basically in our human nature to want things we can’t have.

Some things aren’t as easy to get as others, but I’m here to convince you how simply being authentic and honest can be more than half the battle.

I mean I never thought I could raise $1500 in a couple of days… Until I did.

The cold Pennsylvania winters were as tolerable as they sound, and unfortunately for me, I was bed ridden for over a week battling a sickness.  It gave me a lot of time to think, and so naturally, I decided I wanted to solve a problem.

My idea was called “Pace Buddy” and would allow people in various cities to connect with others who shared similar running capabilities and go for runs together.  This was at a time before MapMyRun, Nike Fit and other now popular apps. Heck, the iPhone didn’t even exist yet. I knew exactly how I would grow it, what incentives I’d offer to keep engagement up, etc   The only problem was I had no idea how to actually code.

Pacebuddy Splash Page

Going into my final semester at East Stroudsburg University, I approached my professors about possibly funding me to go to a conference hosted by Carsonified called Future of Web Apps (FOWA), specifically for web developers.  When they completely shut me down, I thought of a plan B. I was doing some freelance work at local web design company owned by two former alumni. Both of them very talented as one currently runs a successful photography business in Buck County, PA and the other is Jessica Alba’s right hand man in all things web at Honest Co. Another alumni was in the office at the same time and is now an entrepreneur and founder of QuietPunch.

Steffen Hoffman Jessica Alba
My buddy with his friend and boss, Jessica

While I was sharing the story of how I got rejected, I share with them my had a random idea to sell ad space on a t-shirt for $20 bucks a pop. They immediately turned to me and said, “Go for it.”

That night, I dove deep into my white body Macbook and pushed the limits of my WordPress skills to getting a site up and running.

I figured lots of small companies were just as eager as me to be seen at the conference, but couldn’t afford to be a big sponsor at the venue. The angle in my mind was generating enough buzz through social media (Facebook had just come out on my campus a year before) to leverage the awareness and sell the companies on that. If all went according to plan, I would have enough money for the trip, and these companies would get cheap advertising at the conference.


Looking back, I discovered a few simple steps made it possible, and I want to share them with you.

#1 – It’s not how many resources you have, but how resourceful you are

Tip: So go out there and reverse engineer who your potential market is and how to reach them. Warm introductions and support are the heavy hitters. Blasting 150 random people only to have your email to go unread is no bueno.

Two weeks before the conference, I sent an email to Nick La, who designs and maintains Web Designer Wall, an instructional blog on modern design technology.  I basically told him how awesome he and his work is and pitched my walking billboard idea.  What I needed was a supporter with a lot more resources than I had.

Not only did Nick reply with great advice for the execution of my operation, but he also agreed to reserve a couple spots and pass along my story to all his web developing friends. (Email convo at end of post)

February 14, 2.55am: Nick emails his contact list sharing my campaign.
February 15, 3.00am: The t-shirt is sold out.

Imagine me waking up the morning of the 15th.  It was like Christmas.


#2 – Seeing is Believing

Tip: Make sure you have something visual to share. You may be amazing with your words but having something visual on the internet solidifies that this is real. Unfortunately it’s the same reason people feel good about waisting spending money on billboards instead of Facebook ads.If they an visit it online, or hold a flyer, it must be real/ trustworthy.

As per Nick’s advice, I made my campaign as visible as possible.  I added more spaces to the back of the shirt, doubling the income.   I created a website and sponsor page on my blog including links to each company’s website, posted a picture of myself in the shirt showing “your logo here” on the front and networked on a bunch of social media platforms hosted by FOWA for extra exposure prior to the conference. Create

I became a recognizable cause that people could trust and wanted to support.  My story was even being featured on 10+ blogs by other web developers.  The shirt was everywhere.


#3 – Make it Legit

Tip: When you can address their objections and fears before they even know they have them, you’ve already won. The trick is to do your homework and learn what those might be. This is a page right out of Ramit’s negation book.

I wrote up a FOWA contract to serve as a safe guard for my sponsors.  It defined my plans to wear the shirt both days of the conference and guaranteed a full refund if I wasn’t able to raise enough money to go. The most important thing was actually MAKING IT HAPPEN. Gary Vaynerchuk has a quote he leans heavily on that says “Ideas are shit.” It’s something that I constantly, to this day, keep fresh in my mind as a way to test myself. Any who, I digress. I gathered my receipts from the conference passes, airline tickets and hotel room as tangible proof as well.

At the conference, people approached me, recognizing my t-shirt and commending the idea.  A groups of web designers from London even offered me a job in Europe after shooting the shit for a couple of hours.

My little t-shirt operation had generated enough buzz to get the attention of people from all over the world.  How cool is that??

#4 – Follow-Up and Share!

Tip: Sponsors love follow up, especially in visuals and any metrics you can provide. Put together a quick PDF or Powerpoint and deliver a quick media kit follow up. This will help the relationship continue after the even should you have any opportunities down the road you feel might be mutually beneficial.

Once I was back home, freezing in PA, I followed up with photos and stories, thanking my sponsors for their support.  They were able to see the where their donation and the impact it had not only on me, but on tons of other attendees as well.

Gary Vaynerchuk 2007
Gary Vaynerchuk 2007

My plan was simple, but unique, and I made sure to keep it totally honest and upfront, which was enough to spark people’s interest. They saw my determination, trusted my motives, and the best part was, they were getting something out of it.  I utilized a couple good resources and wasn’t afraid to ask for some help.

By the end of it all, I raised $1500 to pay for the flight, the conference, even a sick waterfront hotel in South Beach.

So whatever your thing may be, it may not be as far out of reach as you think.


If it’s worth it, and you have a plan, anything is possible.


FOWA 2008
Me and @fowa peeps @joleen




Email to Nick La on February 8th, 2008:

Hello Nick,

I frequently visit your site and am a huge fan of your work. I’ve recently dove into the world of web design and development and your website has helped me out a lot.

The reason I’m writing is because I am interested in advertising your site at the Future of Web Apps conference at the end of this month. I am selling adspace on a t-shirt I plan to wear both days at the conference for $20 a space. I’ve created a blog with all the information you would need if you are interested.

Yes, I’m a poor college senior and this would mean a lot to me if I could go.

Either way I would really appreciate it if you could get back to me or had any ideas of anyone that would be interested.


-David Bracetty


Sure, I can support you with couple spots. I can even help you further (ie. post your link on my blog post) if you can post pics of how the tshirt going look like or how the logos going to be printed (ie.




Hi Nick,

Thanks for the quick response. I’ve been working the blog all day. I’ve posted ‘The Shirt’ and ‘The Ad Space’ page where you can see more details of what the arrangment of the adspace is and what are the dimensions of the ads. I will update it as requests for ads come in.

I really appreciate any help you can give me.



Ok, David. I really want to help you out. I like your idea (although it has been done many time before), but I think it will work. Here are my suggestions:

Post a photo of yourself (ideally wearing a white tshirt and point your fingers at the logo spots “Your logo here“) (you can build more trust by real photo)
On your sponsors page, make the sponsor smaller and post a link to their actual site instead.

Then I will forward your site to all my ad sponsors, designer friends (trust me, they all can afford $20, but you gotta convince them that the money is worth spend)
I will initiate by sponsoring couple spots for you



You know what happened after that.