How Listening to One Podcast Earned Me $1,250, a Trip to Austin, and a Workshop With One Of My Idols

Jordan Carroll
The Startup
Published in
10 min readNov 5, 2019

Why you’re not actually competing against everyone, winning a contest is extremely attainable, & what I learned meeting a virtual mentor in person.

Giveaway
Photo by Don Agnello on Unsplash

I’ve entered many contests in my life — raffles, giveaways, competitions… you name it, I’ve taken my swings. I’m not sure if it’s due to the burden of a faulty memory, but I don’t remember winning anything significant. I think a few times I’ve walked away indifferently from a raffle with a gift certificate, a trinket that eventually made it’s way to goodwill, or an oversized t-shirt.

When I hear about big contests or giveaways, the information tends to go in one ear and out the other, especially if there’s work involved, because:

  1. Contests seem so farfetched, and even illegitimate at times
  2. There are always more important ways I could spend my time
  3. It’s easy to dismiss my chances because of the perceived competition

It’s easy to tell myself these stories.

Plus, I’ve had a tendency to enter contests that for the most part are low barrier to entry (thus less chance of winning). I’ll buy a couple tickets for the 50/50 raffle at an NBA game, drop a business card in the bowl for free lunch at a restaurant, or tag friends on an Instagram post offering a free trip to the Bahamas for spreading the word.

Does any lucky commenter ACTUALLY go to the Bahamas?!

So, when I initially found out about Noah’ Kagan’s Small Business Giveaway, I caught myself stuck in the same self-perpetuating loop of, “that couldn’t happen for me…”

You can imagine how surprised I was when I found out I won.

Or was I?

Who Is Noah Kagan?

Noah Kagan jumping

1. Noah is the Chief Sumo at Sumo, AppSumo, and King Sumo — a group of companies generating 8 figures of revenue by providing tools and solutions to help entrepreneurs ‘kick more ass.’

2. He was the #30 employee at Facebook and #4 at Mint, where he developed and executed the entire marketing strategy.

3. His website (OkDork) and podcast (Noah Kagan Presents) are about actionable business advice for entrepreneurs and business people.

4. He lives in Austin, TX, loves tacos (who doesn’t), mountain biking, and learning new things like woodworking or sword casting.

5. He’s always experimenting in his businesses, one of which is engaging with his audience in a variety of ways.

I listen to his podcast, subscribe to his blog, watch his Youtube videos, etc.

I’m a big Noah Kagan fan.

He’s one of those people who’s become a ‘virtual mentor.’ We all have them. We read their books, consume their content, like their social media posts, even take action on their advice from afar. They seem well out of reach, yet so accessible at the same time.

The internet is weird like that.

But at the end of the day, everyone is human. We all desire connection. That’s why, when Noah presented an opportunity to meet him in person, I knew I had to make it happen, despite my dissonance toward competitions.

The April Small Business Giveaway

Taco with a megaphone

In April, during one of Noah’s podcasts, he announced just that opportunity.

His “Small Business Month Giveaway” was simple:

  1. Grow Your Biz: Leave a comment with the #1 thing you’re doing to grow your business and show the ideas, experiments, and results.
  2. Share the Podcast: Refer at least 1 person to subscribe by sharing on social media or emailing to your friends.
  3. Leave a Review for the Podcast.

What Could You Win?

Everyone could win: Noah would send you $1 via PayPal just for completing the steps above. But, I was fixated on the grand prize for only 5 people

AppSumo Prizes
The GRAND PRIZE.

I made a mental note. I put it down in my calendar to come back to the comment during the last week of April. I wanted some time to think about what to write, let it sink in my subconscious, and help me focus.

How I Won the Contest

I knew that based on the number of comments on the blog there would be 300+ people in the initial applicant pool.

Fortunately, all the answers were public. You can see them all here, including mine if you scroll far enough. I could literally see what my competition wrote before writing mine. And, I was submitting at the end of the month, so my answer would show near the top once it closed.

I noticed that at least 50% of the answers were:

  • Only a few sentences long
  • Riddled with spelling errors
  • Lacking insight or substance

This got me thinking: How much effort would it REALLY take to win this?

The Continuum of Doers and The CraigsList Penis Effect

I read an interesting article on Ramit Sethi’s blog called “How to Win Any Competition You Enter.” It took second place to “The CraigsList Penis Effect” in captivating titles of relevant articles about contests on his site.

Both articles point to one insight I found true in this experience (and life):

You are never competing with “EVERYONE” who enters a competition. Every obstacle makes lazy or uncommitted people drop out, leaving you to compete with a tiny handful of true winners at the top.

The Continuum of Doers
Graphic from “How to Win Any Competition.”

This phenomenon is illustrated in the graphic above called, the “Continuum of Doers.” In a more, let’s say, NSFW version, we have the “CraigsList Penis Effect,” which has it’s own Urban Dictionary definition:

The Craigslist Penis Effect describes situations where everyone else is so horrible that, by being even half-decent, you can dominate everyone else and win. e.g:

a) any g-rated women-seeking-men Craigslist ad will be met with dozens and dozens of e-mails that are just penis pics, and

b) a “real” email will automatically be better received than the penises.

These moron men on Craigslist would be better served writing 5 half-decent responses, testing to see which got the best response, and then sending it out instead of a picture of their generally mediocre manhood.

Hard and easy wins
Other examples of when to use the Craigslist Penis Effect.

This effect applies to anything with perceived competition (see above graph). The reality is, most people weren’t going to do the hard work. The smaller percentage that would do the work, weren’t going to do it well. So, I’d only be competing with the smallest percentage of people who really wanted to win and also produced quality work, and met the qualifications.

Celebrate The Barriers

Back to my initial thoughts about the competition. Seeing these barriers to entry got me excited. Knowing Noah, he would only be selecting those who went well beyond the call to answer his question. I posed myself the question:

What if I was willing to do what 99.9% of people wouldn’t?

I started on my submission, a comment about how I planned to grow my business, with experiments and results. This turned into a 2,000 word, highly detailed “comment” complete with references to Noah’s videos, podcasts, advice and suggestions that I’ve applied, and reasons why I should win.

When I finally hit submit, I sighed in relief. I felt amazing because I knew I had a shot. I’d never felt so good about a ‘competition’ and my chances. About a month later I found out from Noah himself, I was one of 5 who won.

Making The Most Of The Experience

Jordan and Noah after a ride
At the Sumo Charity Ride.

Leading up to the workshop and my trip to Austin, I didn’t know exactly how to take advantage of the opportunity to the fullest. But what I knew for sure — I didn’t want this situation to be about ‘taking.’ While I technically won a competition, it was also a great opportunity to provide gratitude and value to a virtual mentor in my life who had already provided so much to me.

As I thought more about how to show that, I leaned into a couple strategies that paid off immensely. You can use these principles to provide value in many situations, not just winning competitions:

  1. Starting Group Communication

Since there was 5 months in between the time we won the competition and our meet-up in Austin, I wanted to give us every opportunity to connect before hand to build camaraderie. I sent out a group email, introduced myself and got the conversation started. This not only centralized communication for Noah, but we followed each other on social media, started a text group, and created accountability for what we wanted to get out of the experience.

Takeaway: Organization and communication is hard, and few people like doing it. If you can be proactive in taking the lead, you can make life easier for everyone else.

2. Getting a Gift For Noah

I wanted to bring Noah items he couldn’t get anywhere else, including a hand woven shirt from an ayahuasca ceremony in Peru and some candy from Medellin I’d acquired during my time living there. And, with a group of five of us, we could also put our funds together to get something bigger. During one of Noah’s podcasts, he mentioned wanting to try sword making. I found a place in Austin he could do that, and we all chipped in. I wasn’t surprised that the others were bringing creative gifts too.

Takeaway: Make notes of specific and meaningful gifts you could get for people by listening to them when they mention a need or desire. It gives you the opportunity to give thoughtfully, especially if they don’t expect it. Even my dad is now careful talking about his bucket list around me after I bought him a surfing lesson for his birthday this year.

3. Going Early For His Charity Bike Ride

Ironically, the weekend before our workshop, Noah was hosting a Sumo Charity Ride — a fundraiser to purchase laptops for underprivileged children in the Austin area. Not only would this give me a chance to meet Noah before the workshop, but it was also an opportunity to support his cause, meet some amazing people, and do something awesome for charity. Plus, TACOS.

Takeaway: Take opportunities to support mutual causes you believe in and put yourself in a position to connect deeply. During the group session, Noah would be busy with 5 of us. During his fundraiser I was able to get valuable 1–1 time.

The Workshop

Jordan and other winners at Sumo
Workshop day at AppSumo HQ!

The day finally came. We all arrived in Austin, on a HOT day (are there any cold days in Austin?) incredibly excited for the workshop, to meet each other, and talk about our businesses. The group was unique — all of us in different stages of life, business, and background:

  1. Kyle Borcik: Owner of Borcik jewelry company with his wife, Arielle.
  2. Brent Daugherty: An adventurer and co-founder of Awakn Coffee in CA.
  3. Philia Kelnhofer: A mother of three and founder of Sweet Phi food blog.
  4. Josh Terry: A violin instructor and music teacher in the Austin area.
  5. Jordan Carroll (me): A digital nomad and Remote Job Coach.

8 Business Lessons From The Workshop

With the wide variety of experience in the room, we took turns sharing our business problems, successes, and goals. Noah led the discussion, often challenging our assumptions, orchestrating advice, and providing different lessons he’s learned from scaling multiple businesses to 7 or 8 figures:

  1. Keep it simple, keep it fun. We tend to overcomplicate things, and business should be fun, and while not easy, it should be simple.
  2. Do more of what’s working, kill and remove what’s not. Be ruthless with the things that don’t generate outcomes you need, and fuel the things that do.
  3. Build momentum, it’s the most powerful thing in business. Just get going, or take that small next step, you’ll find a groove in action, not planning.
  4. Restrictions breed creativity. Use Parkinson’s law to your advantage, set limits and force yourself to figure out how to get it done in the allotted time.
  5. Build your confidence with small wins each day. You don’t have to hit the home runs — singles, over time, bring in runs too.
  6. Re-visit what worked well in the past that you don’t do anymore. A reminder of what brought success in the first place can often bring more.
  7. Don’t spend any money until you make it. There’s so many ways to validate an idea, test and trial, and sell first, spend later.
  8. Ask yourself: How could this be easy? A simple question that forces you to strip down an issue and potential solutions to their bare bones.

Gratitude… and Tacos 🌮

Jordan and Noah chillin together
Noah rocking the hand woven Ayahuesca shirt from Peru.

I’m forever grateful, not only meeting Noah, but the other contestant winners, the amazing people at the charity bike ride, and for the experience itself.

Winning this contest was a catalyst for me to leave my job, pursue entrepreneurship full time, and also have the confidence to win another contest only a month after this one (Another article to come on the Selina Nomad’s Roadtrip in the near future).

So, next time you’re tempted to think you can’t win a contest, the competition is too thick, or it’s not worth it to put in your all (for anything)

You might end up eating tacos with one of your idols.

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Jordan Carroll
The Startup

I help high performers land legitimate remote jobs to gain freedom and flexibility in their career and personal life.