How I turned my bucket list into breakthrough marketing campaigns (and fueled 9-figure growth)

What do you want to do before you die?

It's a question that stops most people in their tracks. Maybe you've thought about snorkeling the Great Barrier Reef or hiking the Great Wall of China. Perhaps you've got a mental list tucked away somewhere, filled with dreams you'll get to someday.

But here's what I've learned: your bucket list isn't just about personal fulfillment. It can actually become the secret weapon in your marketing arsenal. 

I'm not talking about work-life balance. I'm talking about something far more powerful: living boldly and using your life experiences to fuel campaigns that drive real business results.

Let me take you back to 2010, when this whole journey started for me.

The Old Spice moment that changed everything

I'd just landed an internship with Old Spice. They were launching their Fresh Collection deodorants, including one called Matterhorn. And get this – they sent me to Zermatt, Switzerland, for two weeks to do crazy stunts for their campaign.

How did a college kid land this gig? Well, I'd been running a video production company with my brother since I was a kid. Plus, I was studying marketing, happened to be early on Twitter, and was passionate about snowboarding and brand storytelling. When all those things converged, magic happened. 

Old Spice needed someone who could tell their brand story in a way that stood out, and I realized something crucial: I could get paid to do the things I loved while helping brands achieve their marketing objectives.

That spark led me down a decade-long path of running an adventure media agency. Brands were literally paying me to go high-altitude mountaineering, trek through jungles, and race through obstacle courses. I was living the dream.

Then in 2017, I made a pivot that probably seemed insane to everyone watching.

From adventure filmmaker to B2B SaaS founder

My brother Chris and I had always worked together on entrepreneurial ventures, but we'd been following separate paths for about six years. He'd built this beta product called Trainual – basically a combined wiki and LMS. It helps businesses document who does what and how, so they can scale without the chaos.

The first time I actually tested it, I was climbing Denali in Alaska. I documented everything my adventure agency needed to run while I was completely off the grid on a glacier. When I came back and saw how smoothly everything had operated without me, I was hooked.

But here's the thing – I wasn't ready to give up on adventures. Instead, I started thinking: how can I infuse the things I want to do in life with growing this business? How can my bucket list fuel our marketing campaigns?

The bucket list that became our marketing playbook

Here are some of the items that I had yet to check off my bucket list back in 2017: 

🦈 Go on Shark Tank 

🧑‍🎤 Collaborate with a music icon 

🏀 Play basketball on an NBA court

🌎 Visit every continent

🏃 Run a marathon

✍️ Write a book

Looking at that list, I started connecting dots. Which of these dreams could benefit our business? Which ones aligned with our audience, our message, our brand story?

What followed were five campaigns that took us from 10 customers to 10,000, built a team of over 160 people, and created some of the most memorable marketing moments in B2B SaaS. 

Let me walk you through each one.

Campaign #1: "Go on Shark Tank" (without actually going on)

Shark Tank was at its peak popularity in 2018. We discovered something interesting while running our early Facebook ads – turns out, people who followed Shark Tank and the Sharks themselves were perfect prospects for Trainual. These were the entrepreneurs we wanted to reach.

Our message was simple: "Every business needs a playbook."

Not everyone can get on Shark Tank (spoiler: we didn’t). Not everyone can get a deal. But what if you could work with the same tools and strategies the Sharks give their portfolio companies?

Here's how we made it happen. First, we hired Daymond John to speak at a virtual event during COVID when speaking rates had plummeted. That was the start of a great relationship. Six months later, he invested in our Series B. From there, we recorded countless assets together and built multiple campaigns.

To distribute these campaigns and assets, we looked at Daymond's speaking calendar and started strategically sponsoring events where he'd be presenting to our target audiences. He'd shout us out on stage and bring people to our booth. This became our training ground for event sales – now we have an entire team dedicated to it.

The results? We cut our customer acquisition cost by 30–40% on key channels. The brand awareness acceleration was massive. And while we never actually pitched on the show, Daymond eventually invited us to visit the set, walk the hallway, and meet all the Sharks.

Bucket list item: checked. Business impact: transformational.

The insight

Leveraging credibility and capturing a cultural moment is a trust accelerant. When you align your personal goals with what your audience already loves, magic happens.

Campaign #2: Collaborating with Montell Jordan

I've been a musician my whole life. I bought a guitar in sixth grade, learned all the Blink-182 songs, and played in punk bands. When I wrote "collaborate with a music icon" on my bucket list, I was probably thinking Travis Barker would drum on one of my songs, or I'd co-write with Matt Nathanson.

I never imagined it would be R&B legend Montell Jordan.

But think about it – "This Is How We Do It" was the perfect message for a company that helps businesses document their standard operating procedures. This is literally how you do it: write it down, scale it up.

So, I found Montell on Cameo and booked a 10-minute call to pitch the idea. He loved it. (Funny story – Cameo cut us off right as we were exchanging contact info because they don't like off-platform deals. I had to quickly tweet at him to keep the conversation going.)

We didn't just want to make a jingle; as a musician, I couldn't do that to myself. We wanted to create a legitimate remix that people would actually want to listen to at the gym. So, we rewrote "This Is How We Do It" to be about the entrepreneurial grind instead of Friday night parties.

We shot a music video, created a whole series of commercials, and distributed them through Spotify and Def Jam's YouTube channels. Montell worked it into his live concerts. The Phoenix Suns even used it in their pregame warmups.

The campaign generated 50 million impressions, 500,000 streams, and a 60% increase in traffic that led to 800 new accounts.

The insight

Nostalgia reimagined + brand narrative = shareability

When you take something people already love and give it a fresh spin that aligns with your message, you create content people actually want to engage with.

Campaign #3: Playing basketball on an NBA court