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Skydiving, Doughnuts, Videos, and Websites: How 5 Creative Job Hunters Grabbed Attention to Land Awesome Jobs
6 Stories of Job Hunters Who Went Above & Beyond to Land An Amazing Job

Happy Saturday Everyone! 👋
(Read time 10 min 4 sec)
Welcome back!
It has been a crazy week.
Many of you are joining this newsletter for the first time after my LinkedIn post about the skydiving job hunter, Chris Serrano, went viral.
I’m excited to have you here, and I promise I’ll do everything I can to land you a career-accelerating job faster and with less stress.
Also, for my Dad’s birthday earlier this month (Happy Birthday Dad) I bought tickets for us to see the Mariners play the Red Sox at Fenway Park (Go M’s!).
He’s a massive baseball fan but has never made it to Fenway.
So, if any of you are Bostonians who are also going to the Mariners/Red Sox game on Monday, email me and let me know so we can meet up before the game!
Ok, enough about me and more about you knocking your job hunt out of the park like a juiced-up Mark McGuire.

Photo by SPX/Ron Vessly Photography via Getty Images
Read on, my badass brothers and sisters, for:
👔 1 job hunting tip: How 5 Creative Job Hunters Grabbed Attention to Land Awesome Jobs
📈 17 companies who raised money this month and are hiring people like you!
👔 1 Job Hunting Tip
Skydiving, Doughnuts, and Websites: How 5 Creative Job Hunters Grabbed Attention to Land Awesome Jobs
Applying for a job has never been easier.
That feels like a good thing.
But in reality, it’s not.
The onset of remote work and the ease of application has flooded popular job postings with hundreds of resumes in minutes.
If you’re a job hunter trying to get noticed purely by how many keywords from the job description you can pack into your resume…
Good luck!
The hiring manager will scan your resume for less than 30 seconds, and if you’re lucky, they’ll see something they like enough to click the button that moves you to the next round.
But odds are, the resume isn’t going to stand out from the crowd, so they’ll click the other button.
The dreaded auto rejection.
When I was trying to break out of my cubicle data entry job, I would spend agonizing hours updating my resume and answering all the application questions, only to be sent a rejection seemingly immediately after submission.
It almost made me lose hope entirely.
I thought that was the only way to get a job.
But I was thinking like 99% of job applicants.
As marketing GOAT Seth Godin says…

What does he mean?
How could you get a job without emailing a resume?
Come on now.
Do you think that by doing everything that everyone else is doing, they will somehow be able to see your uniqueness, and you’ll get the job?
Nah, you have to do more than that.
You have to get creative.
Read on to discover how these job hunters stood out from the crowd and landed their next career-accelerating opportunities without sending an application.
1. Charlie Hoehn

Photo by https://www.charliehoehn.com/
The Story:
Charlie graduated college in 2008 and entered the job market in one of the hardest-hit economic times in US history, The Great Recession.
The internship I had done at an ad agency that looked promising all of a sudden laid off a bunch of their staff.
After his job at an ad agency fell through, he hit the applications hard.
This was before the “easy apply” button, so he spent weeks working on and submitting hundreds of applications and resumes.
His success rate?
Less than a 0.2% response rate.
He received responses from only two companies of the over 100 applications he submitted.
Hopelessly lying on his bathroom floor, Charlie realized that the advice he had been given about the importance of updating his resume didn’t work.
I have to do something different.
This isn’t going to work.
The Stand Out Moment:
Instead of submitting more applications, Charlie took a different approach.
To start, he pretended he had dream clients and dream gigs and would assign himself work.
One of the blogs Charlie followed was Ramit Sethi’s “I Will Teach You to be Rich.”
Charlie noticed Ramit was a great speaker but didn’t have a demo reel anywhere on his website.
So Charlie assigned himself some work and reached out via email.
Charlie highlighted how much he enjoyed Ramit’s blog, how it had helped his finances, and how great of a speaker he thought Ramit was.
He told Ramit that he noticed there weren’t many videos of him on the site, likely because video production is a heavy process that takes a long time.
Then Charlie offered his solution.
He would do Ramit’s video editing for free.
All Ramit had to do was send Charlie his unedited videos, and he would make them all pretty and send them back to him free of charge.
He told him that he would love to start by providing the videos for free and then, after he had proved himself, under a paid agreement.
Charlie sent a video he had already created of clips of Ramit speaking to show what he was capable of.
Guess what happened?
Ramit responded via email, then they got on the phone, and it turned into a paid gig.
Charlie repeated the exact same process with Tucker Max and then finally and most famously with Tim Ferriss.
The Career Since:
Charlie became the first employee of Tim Ferriss, allowing him to travel the world and meet top entrepreneurs, authors, artists, philosophers, politicians, and thought leaders.
Since then, he has started multiple companies, written two books, became the Head of Multimedia for Scribe Media, and is now a keynote speaker sought by top organizations worldwide.
2. Lukas Yla

Photo by Lukas Yla
The Story:
Lukas Yla grew up in Lithuania but had his eyes set on landing a marketing role in San Francisco in 2016.
At the time, tech was ripping in the Bay Area, and everyone wanted a piece of the action, so competition was high.
Knowing that he was entering the US job market as an outsider, he knew he had to do something so his resume didn’t end up in the (virtual) trash can.
The Stand Out Moment:
Any person can’t just walk up to an office building unannounced… but a delivery person can.
So Lukas printed himself a fake Postmates t-shirt and delivered doughnuts to 10 of the top advertising agencies and 30 top tech companies.
On the inside of the box, he attached a copy of his resume with a note saying…
Hi,
This delivery is not a mistake. I pretended to be a Postmates delivery guy to ensure my resume was delivered to you personally.
As you have noticed, I approach things in a different way and most importantly - I like to get them done.
My name is Lukas; I am a marketing guy with 5 years of experience. I admire your company and would love to work for you.
If I spiked your curiosity and you are wondering how to reach me, please entr bit.ly/check-resume in your browser window.
For the time being, please enjoy these magnificent & famous donuts from Mr. Holmes Bakehouse.
The doughnut delivery strategy worked to land him 10 interviews.
The Career Since:
While it’s unclear whether the doughnut strategy landed him a job, in less than a year, he became CEO of a Lithuanian ride-sharing company and is currently the Director of Carsharing Operations at Bolt.he became CEO of a Lithuanian ride-sharing company in less than a year
An awesome outcome for a hungry candidate.
3. Caleb Ralston

Photo by Acquisition.com
The Story:
When Caleb was 15, a mentor handed him a book that would change his life.
That book was Crush It! by Gary Vaynerchuk.
He saw the writing on the wall that content creation was the future and that there would be LOTS of money to be made if you knew how to do it well.
Fast forward about 8 years, and it was clear Caleb had taken Gary’s advice.
He was living in Bellingham, WA running his own freelance videography business.
A friend sent him a screenshot of an Instagram post from Gary Vee announcing he was looking for videographers.
The Stand Out Moment:
Caleb decided to go for the position.
He emailed David Rock (DRock), Gary’s Executive Creative Director, and decided he would get his attention any way he could.
I decided I was going to harass him in a smart way.
By being very intentional with it and always providing more value each time you follow up.
He grabbed his phone and filmed himself eating chicken nuggets while editing a video, letting him know he saw the post about the job and how excited he would be about working together.
He didn’t get a response, so he followed up 24 hours later with another video.
He didn’t hear back, so he followed up with another video.
His persistence and value delivery paid off!
Eventually, David replied, letting Caleb know he had been sick, and they scheduled a call.
That call turned into a job at PureWow, a company under the VaynerMedia umbrella, and in two weeks, he was living in New York City.
The Career Since:
8 months after joining the company, David tapped Caleb to join Gary’s private videography team.
He traveled the world with Gary filming his every move and eventually was handed the keys to his TikTok account, where he grew the followers from 300k to 1.5M in 12 months.
Caleb worked for the company for over 3 years and has since left to become the Director of Brand for Alex Hormozi’s Acquisition.com, and is responsible for growing one of the fastest social presences on the internet.
4. Nina Mufleh

Photo by Shaz Khan via somamagazine.com
The Story:
In 2014 Nina Mufleh moved from the Middle East to San Francisco.
She dreamed of working at a tech company, but after a year of job hunting, she hadn’t landed any interviews.
My approach stems a little out of desperation after a year of trying unsuccessfully to land interviews with Airbnb and other tech companies.
She finally resorted to doing something that she thought would be sure to grab the attention of Airbnb.
The Stand Out Moment:
Seeing that Airbnb didn’t have a presence in the Middle East, Nina did extensive market research and created an online resume highlighting how the company could build a presence there.

She even went as far as to design the webpage to resemble the Airbnb design and formatting.
Once she finished the site, she tweeted it out to the Airbnb founders.

The tactic worked!
She was reached out to by the Airbnb founders, the Chief Marketing Officer, the Head of Business Development, several other team members, and recruiters and landed that coveted interview.
The Career Since:
She went through the interview process with Airbnb and unfortunately, she wasn’t extended an offer.
But, fear not!
Though Airbnb didn’t place an offer, others quickly came knocking on her door.
LinkedIn, Uber, Dropbox, and several venture capitalists reached out to speak with her or offer her a chance to interview.
Nina ultimately decided to take an interview with the freelance work darling Upwork and was offered a role as a Growth Manager.
5. Chris Serrano

The Story:
Chris Serrano was laid off the first week of May 2023.
Chris is a creative director with multiple awards for his work and has been featured in almost every major media outlet, so it’s almost no shock what he did next.
The Stand Out Moment:
Pulling on his creative strings and his love for skydiving (he has over 200 jumps), Chris filmed a video.
But not just any video.
He brought a cardboard sign in the airplane that read “OPEN4WORK” on one side and “GREAT IDEAS“ on the other.
After recording the video, he posted a layoff announcement on LinkedIn, and the people went wild!

In less than 3 days his creative post had over 40k reactions, 1400 comments, and almost 1k reposts.
But what about his job prospects?
Well, the CEO of pre-seed startup Linkup posted a response video where he offered Chris a job and then jumped out of a plane himself.

The Career Since:
It’s tbd as to whether or not Chris accepted the Linkup offer or if that was purely a social media response, but it’s safe to say he got the attention of many people looking for Creative Directors.
I’m actually speaking with Chris next week to learn more about his awesome stunt, so if you have any questions you’d like me to ask, please respond to this email with them.
BONUS 6. Ryan Graves

Photo by CNBC
The Story:
It’s impossible to write a story about getting a hiring manager's attention in creative ways and NOT mention Ryan Graves.
In 2009 Ryan was working as an IT Program Leader at GE Healthcare.
While the work wasn’t terrible, it wasn’t where he saw himself in 20 years.
The corporate career-20 years in the same company-was not really my thing.
I can’t be the GE guy.
He had his sights set on tech just as what would become some of the decade-defining companies were just getting their footing.
He had his eye on one company in particular.
So, Graves applied for a job… and was rejected.
Most people would take that as a sign that he wasn’t meant to be a part of the company.
But not Ryan.
The Stand Out Moment:
Instead of giving up, Ryan spent hours each week cold-calling bars, restaurants, and other businesses in Chicago, encouraging them to sign up for the application, onboarding them, and answering their questions.
After signing up 30 businesses to the platform, he emailed the list of new customers to the company’s founders, executives, and investors.
Judging by each of the stories above, I bet you can guess what happened next…
His tactics to get noticed paid off!
He landed a role with Foursquare and worked as a Business Development intern for 3 months.
But wait…
There’s more…
The Career Since:
After landing the role at Foursquare, Graves became a master networker in the tech community.
One fateful day while keeping his ear to the ground on Twitter, he saw a founder asking if anyone knew of an entrepreneurial product manager/business development killer for a location-based service.
Graves responded, “Here’s a tip. Email me.”

The MVT - Most Valuable Tweet
That founder was none other than Uber co-founder Travis Kalanick.
And the “pre-launch” company he was referring to was…
You guessed it.
Uber!
That single Tweet led Ryan Graves to become Uber’s first CEO, later its Senior Vice President of Operations, and net him over 1 Billion dollars.
That’s right.
One Tweet = One Billy $$$
Talk about a wild outcome!
Follow Ryan: LinkedIn, Twitter, Website, Soundcloud
So for all you hungry job hunters out there looking for ways to get the attention of hiring managers, hopefully, those 6 examples sparked the creative juices in your mind.
If you look at them all, some common themes emerge:
They were deeply interested in the companies and/or individuals they wanted to work with/for.
They used a unique set of skills or experiences to create value for people inside the company.
They showcased interest, excitement, engagement, creativity, and ability.
Their belief in themselves and what they had to offer propelled them to truly go above and beyond.
And, most of them didn’t spend a dollar doing it.
What can you do to catch the attention of the hiring managers you want to get in front of?
What unique set of skills can you showcase to solve a problem for them without being asked?
I want to see some of you added to this list when I re-write this post next year.
Go get it!
I want to hear from you!
What are you struggling with?
What’s an area that you’re excited about and you want me to dig into?
What company or leader do you want to learn more about?
Email your question to [email protected], and you’ll likely find a complete breakdown in a future edition of the newsletter.
📈17 Hiring Tech Companies
Click here to access the data for 17 companies that raised money this month and are hiring people like YOU!

There you have it, 1 job-hunting tip, 17 startups that recently raised money and are actively hiring, and one wild week in the books.
Let’s become career champions together 🏆
Kyle
P.S. Whenever you’re ready, there are 3 ways I can help you:
#1: Free Job Hunt Strategy Call: Request a free job hunt strategy call with me to get closer to landing your next career-accelerating role. On our call, I’ll walk through your vision and how to make it a reality, cover the obstacles standing in your way, and help determine the best next step for you to take based on your short-term and long-term goals. Schedule a free call today!
#2: Want to get serious about accelerating your career in tech? Discover the small selective group program for ambitious professionals looking to land their next career-accelerating tech role in less than 90 days.
#3: Follow me on LinkedIn for more job hunt systems, productivity tools, and networking templates.
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