Cash Smarter

October 12, 2016  by: Aaron Crowe

What I’m Doing With a $250 Windfall

What I’m Doing With a $250 Windfall


I won $250 in a contest recently, and while it’s not exactly a windfall that will change my life like a lottery win could, it was enough to get me daydreaming about the possibilities with it.

It was a simple contest, which is my prerequisite for entering any contest: Take a photo of myself wearing the hat of a, a sponsor at FinCon, a conference for financial bloggers that I attended in late September. Then put it up on Twitter, with #ClarkCash and #FinCon16 in the tweet after following @ClarkHoward on Twitter.

The free hat was in a swag bag given to attendees, with a business card attached to the hat giving instructions on how to win $250:

“The 4 most creative entries will each win $250 in cash for a total of $1,000! Winners will be announced at Clark Howard’s #FinCon16 keynote speech Thursday at 4:30 p.m.”

I noticed the hat in the swag bag after an afternoon walking around a tent full of sponsors that I wanted to meet, with the hope that I could either write for some of them or have them advertise on my personal finance blogs. I went to my hotel room to rest for a bit when I read about the contest on the free hat, and decided to give it a try.

I pulled some cash out of my wallet and took two photos and tweeted them out:


And this:


I don’t know which tweet won for me, since the site never tweeted who the winners were. But I figured I had a chance for a few simple reasons.

Time and few entries

While in my hotel room resting, I noticed that the contest winners would be announced in about one hour. That gave entrants only one more hour to submit a photo and tweet about it. I figured that with the hat in everyone’s bag for most of the day, if people hadn’t entered by now, then few would.

About 1,200 people attended the conference. I looked on Twitter and noticed that only 12 people had tweeted for the contest. With four of those dozen people getting $250 each, the odds of winning were 1 in 3. I added my two photos and then went to the keynote speech.

I rarely enter contests, mainly because I think the odds of winning are so low. I also don’t like giving out my email address, phone number or other identifying information so they can spam me later. But with this contest, the odds were so much in favor of winning — about 33 percent — that I had to enter.

With 1,200 people at FinCon, there were a lot of possible contestants for the many contests at the convention. Companies were giving away cash, iPads and other prizes simply for entering your name in a drawing. I only entered two other contests, for a free Apple watch and something that I now can’t remember — but I didn’t win either of those.

Time to collect my windfall

Collecting the small windfall wasn’t as easy as advertised. Though winners weren’t required to be present at the speech to win, I went to the last 20 minutes of the speech so I could hear the winners announced after Howard’s speech.

As a few hundred people were filing out of the ballroom, a Clark staffer quickly announced the winners and asked them to come up to the front to meet her. I walked against the exiting crowd and found that the Clark organizers didn’t have the $1,000 in cash to pay the winners, but would be in touch within a few days with the money. I gave her my business card, never expecting to hear from them again, but hoping for the best for my windfall.

The money didn’t arrive by the weekend, so I left for home after getting a message from Clark that the money would arrive within a week.

I won’t go into the entire story here, but after some back and forth on Twitter, I sent them an invoice for $250 on PayPal and the windfall arrived almost two weeks after the contest. Here’s the email notice that I got paid:


PayPal, of course, isn’t free, and it charged me $7.55, or a 3 percent fee. Fine. I’ve still got a small windfall in my pocket.

What to do with this windfall?

The fun now comes in answering that question. For about 30 minutes after winning the contest, I contemplated what I’d do with the $250 windfall. I imagine this is what happens to lottery winners, though in a much larger amount and probably for weeks and with input from financial advisors.

The $250 I won wasn’t going to last that long or buy as much, so it was a simple conundrum. Here are some options I considered?

  • Pay for repairing the washing machine at home, which I just learned was busted.
  • Take my wife out for a date.
  • Put it in the bank.
  • Put in in my retirement account.
  • Fund our emergency fund.
  • Put it back into my business.
  • Go spend it quickly on whatever I could find in San Diego, where the conference was held.
  • Bet it on the ponies.

It wasn’t really a difficult choice. Since it was a relatively small amount of money as far as a cash windfall goes, I wanted to use it where it would have the most immediate impact. Taking my wife out seemed like the smartest choice, followed by having our washer work again.

The other options were either a guaranteed waste of money by blowing it on a bet or going on a spending spree, or were such long-term goals that a $250 windfall wouldn’t accomplish a lot.

Not that an extra $250 invested in my business or retirement account or similar prudent move wouldn’t be a good thing, but it wouldn’t have much of an impact. I’m already doing those things regularly, so I’d rather do something fun with the windfall, as small as it is.

Good news for my wife

My choice was made simple when I returned home and had to pay the washer repairman. Luckily it was an easy fix and only cost $89. After PayPal fees, that left me with $153.45 to spend on a date with my wife.

And the news only gets better. Thanks to a free room each year at any Hilton property as part of our credit card rewards program, we had already booked a room at a hotel in San Francisco for an upcoming Saturday night when our daughter is out of town on a school trip.

With a free hotel stay for the night, dinner out in San Francisco is our only major expense that night and will be paid for by the kind people at Maybe I’ll tweet a thank-you photo to them that night from our dinner table.

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2 thoughts on “What I’m Doing With a $250 Windfall

  1. Tyler says:

    Awesome that you won Aaron, I had thought about entering but decided against it in the end. I hope you and your wife enjoy your night off. I recently discovered that I have been saving last year’s raise in a savings account and have a few hundred dollars in that account. I haven’t decided what I’m going to do with it yet, but I’m adding this year’s raise to it too now.

    1. Aaron Crowe says:

      Hiding a raise is a smart idea. Congrats and enjoy it!

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