Lessons

How My Life as a Musician Helped Me Close the Biggest Deal of My Career

Early mornings and late nights on the road taught me resiliency and the importance of working with the right people.
How My Life as a Musician Helped Me Close the Biggest Deal of My Career
Image credit: Vasyl Dolmatov | Getty Images
Guest Writer
Senior Director of Sales
8 min read
Opinions expressed by Entrepreneur contributors are their own.

I'm fresh off closing the biggest deal of my career -- and the biggest in my firm’s history, in fact. My decade of sales experience at cutting-edge companies certainly didn’t hurt. But if I’m being honest, it's what I learned as a musician that secured the final handshake on this one.

It’s been a wild and winding road, but my rock ’n’ roll-or-bust story contains plenty of lessons for entrepreneurs in nearly any field.

A crossroads.

My band’s debut album on Downtown/Atlantic Records was set to be released Sept. 11, 2006. We were scheduled to play a gig in Nashville the same night. My bandmates and I arrived that morning via the van in which some of us also were living. We did our soundcheck, met our opener (Ra Ra Riot) and then headed over to the nearest Tower Records, eager to see our labor of love on sale in all its compact-disc glory.

The album wasn’t there. And within three months, neither was the Tower Records. Or any Tower Records, for that matter.

Somewhere between finishing the last song of our set and getting on the road to Memphis, label representatives confirmed our album would sit in a warehouse indefinitely as they worked to formulate a Plan B for distribution. I awoke that night to yelling and a cabin full of smoke. I’d been sleeping while a bandmate took his driving shift. We'd broken down on the side of the highway, and the van had burst into flames. The state trooper who shuttled our ragged, dejected cadre to the mechanic’s shop asked us, “What the hell are you guys doing out here anyway?”

And at that point, I had no answer for him.

Lessons learned.

That was the first time I personally witnessed the consequences of industry-wide upheaval, but it wasn’t the last. After my front-row seat for the implosion of the old-school music industry’s business model, I moved into the tech world. Disruption in many shapes is the order of the day.  

During my nearly five years at Groupon, I rode the tremendous highs and lows of a group expected to be the fastest, ever, to drive $1 billion in sales. It stumbled in its first quarter as a public company and never again quite regained its footing.  

These days, at Kiip, I’m a part of an equally ambitious tech company. I find myself looking back on my tour days in our van or the hours spent in the recording studio. It’s taken me a bit of life experience to realize just how many lessons from those days are equally applicable to our ever-evolving and highly combustible industry.

Here are a few of the most important takeaways -- the ones I carry with me every day. They’re also the ones that helped me close my monumental deal. Because at their core, these lessons are about who we are as people and how we treat those around us.

Related: 32 Founders Share the Biggest Lessons They Are Learning Right Now

You are more than your job title.

Most musicians have very high adaptability quotients. Every successful musician I know is multifaceted, boasting various interests as well as skill sets. Our band's lead guitarist also was a sound engineer. He managed to save our bacon at least once when we showed up for a gig at an ill-prepared venue. The drummer is still a drummer through and through, regularly playing studio sessions. He's also a successful serial entrepreneur and a cancer survivor. Our lead singer/rhythm guitarist is playing drums in his new band, Campdogzz, and currently on tour with headliner Cursive. And me? I’m a bass player by trade, but I also dabble in design, production, prose and songwriting -- all skills that life in a band allowed me to flex regularly.

The best tech companies are composed of people who wear many hats as well. At Kiip, I’m a senior director of sales. But that doesn’t define all I do. I'm entirely invested in our customers’ success, so I collaborate across a number of teams to help tell our story internally as well as in our market.

Some days I find myself adapting to the needs of the business in other ways -- mounting new TVs in our conference rooms, fixing our plumbing or doing whatever it takes to keep our business running smoothly. My colleagues do the same, no matter their titles. That kind of versatility is essential for companies that want to stay ahead in their markets.

Related: Stop Calling Yourself the 'CEO' and Start Telling People What You Do

You can’t put a price on preparation.

Our band hammered away at songs in our practice space for more than a year before we played our first show. That level of preparation paid off: Less than 18 months after our first gig, we'd established ourselves as a viable indie-rock band in the Chicago scene. We rarely made mistakes on stage. And when problems arose, we knew our music and one another well enough to improvise, work around the issue and still put on one hell of a show. Even when the kick-drum pedal snapped, mid-set, in Milwaukee or when bad wiring at a club in Williamsburg, Va., electrocuted our singer/guitar player during a vocal break.

Preparation sets apart the strongest companies in the tech space, too. In a fast-moving industry, it can be tempting to race products and services to market. Everyone's after that ever-important first-mover advantage. But you're doomed from the start if you take a customer’s money before you have a solid team in place to deliver on your product’s promise. At best, you’ll be working with a serious disadvantage and no confidence to improvise.

Related: After Completely Freezing During a Pitch Competition, These Co-Founders Stayed Up All Night Preparing for a Second Chance

Your best collaborators are high on competency and low on ego.

I've had the opportunity to work with stellar collaborators, including renowned mixing engineer and producer Mark Needham. By 2006, when we were mixing a record together in Los Angeles, he'd already amassed a seriously daunting resume that included The Killers, Fleetwood Mac and Green Day -- to name just a few. I was secretly terrified his highly trained ear would uncover the dusty corners and imperfections of my playing. But that's not how it happened. Needham didn’t care that I was a 19-year-old kid still figuring out the industry. He knew I’d put in the work and hours to earn the right to his time. He was gracious, kind and thoughtful. A true professional, he devoted himself to getting the sound right on our album. He told me which performances and takes he thought were best and challenged me to do more to serve the song. More than 10 years later, I'm still proud of the result.

No matter the industry, the best collaborators let their accomplishments speak for themselves. Their drive is pure: They want to get it right, so they approach every project without the desire to prove anything. In the tech industry, there’s no riding a past success into a future one. People work with people they like and who they know can get them the outcomes they seek. The best results often come when collaborators and contributors check their individual egos at the door. They roll up their collective sleeves and get to work. If it doesn’t serve the a strategic priority or key business-line objective, there’s no room for it in the space.

Related: Collaboration Works Best With Diverse Collaborators

Destruction with purpose.

I often get asked about my life as a “failed musician.” Failure implies a lack of success, and that's simply not my experience as a musician. I met and worked with many of my heroes, and I got to share that with bandmates -- some of the people closest to me on the planet. Market forces gave rise to a platform-vacuum, and music-industry execs had to make tough decisions. I did not fail. I got further than most, and I had a blast doing it. The lessons I learned during those exciting and daunting years guide my client and colleague interactions to this day, every day.

Back in September 2006, it felt as if the music industry was collapsing like a black hole and I was watching from the event horizon. I had no idea that such destruction and disappointment was a necessary step to reinvent the industry for a digital world. These days, I'm less prone to despair if it seems that a piece of the tech world is starting to crumble.

I now know that disruption isn’t an end. It’s destruction with purpose, and it marks the beginning of a rebirth. When things get tough, lean in and worry not. What’s gone is never truly lost.

Related: 9 Habits That Will Make Your Life (and You) More Interesting

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