What I Learned From My First Rock Band (and How it Made Me a Better Startup CEO)


While being a CEO is cool and all, my ideal job has always been to be a Brazilian rockstar. Sadly, I’ve always had two things going against me: 1. I’m not Brazilian (though I’ve tried very hard on this) and 2. My resume included no rock star experience. That is, until the pandemic, when I formed my first rock band. We practiced weekly for a year and a half, then played our first show to 120 people and a pack full of wild dogs. 

Not pictured: pack of wild dogs.

There’s something deeply valuable in working on something you’re simply not good at until you become borderline competent; it’s like learning a language. It’s also amazing how much you learn if you open up to really being truly not good at something in a deeply public way.

Needless to say, some good outlaw country rocking occurred, but I also learned quite a bit about the similarities between leading a company and playing in a band. So without further ado, I offer you my top learnings and epiphanies from joining my first rock band – and why so many apply to being a CEO.

Song selection is like a product roadmap: listen to your customers

Jerry Garcia’s favorite Grateful Dead song was Row Jimmy Row. Seriously? That song?! Fans didn’t agree. I definitely don’t agree. Here’s an 11 minute version live. Better than melatonin and an edible. 

If you want your audience to love you, play their favorite songs, not yours.

Putting your customers first may be a business truism, but most businesses still don’t get this right at all. Your annual plan or quarterly numbers aren’t as important as listening to the people who pay you.

As my guitar teacher says, “Dude, your tone is a separate instrument. Honor that.”

Putting great technique through a bad instrument just sounds bad. No amount of business acumen can save a business that isn’t in tune with itself or has no strategic plan. And no great speech or messaging will resonate with your audience if you get your tone wrong. 

The hardest part of every song is just starting and ending it.

Getting through verses and choruses isn’t the hard part. You practice those and they’re close to the same every time. Starting a song in sync is like launching the space shuttle to me – everything has to be perfectly coordinated. And ending a song?! My drummer introduced me to the concept of the so-called “trash-can ending.”

I’ve also seen quite a few product launches that struggled to lock in. It’s the hardest part, and something you have to work on.

No one cares about the drums and bass. But the audience will leave if they aren’t solid. 

Bass and drums are just like your ops and dev teams. They’re the heartbeat of the finished product, they have to be perfectly in sync, and they lay the foundation for everything else you do. Without operations and process, you won’t have a product people want to listen to.

It’s not just about what you play and how you play it. It’s a lot about how you look when you’re playing. 

Your audience would rather watch a band that’s smiling and having fun than brilliant musicians who stare stoically at their instruments for the entire show. And no, this isn’t just an excuse to say CEOs have to be extraverts. You really do have to sell it, and selling is part of being a CEO. Also, few products are massive hits without some quality marketing juice.

Each player turns up their amp a little more after each song until no one can hear anything.

This feels just like adding urgent strategic initiatives at your company every week until it’s impossible to tell which is really the priority.

When you practice, you all stand in a circle and watch the drummer. When you play a show, you stand out front and can’t see the drummer.

It’s easy to get lost when you can’t see the drummer. There are so many distractions on stage that if you haven’t completely committed each song into your subconscious, things won’t go well. The second the show starts you discover that you can’t hear your own voice. Or your guitar. And you dropped your pick. It sounds like the bass is the only instrument plugged in. And at least one band member seems to be confused about which key the song is in.

You have to accept that everyone will enjoy the show a lot more if you keep playing through the challenges – and smile. Pick and choose the most important things, then prioritize them, because there will always be distractions. The sound will suck. There will be lights pointed right in your eyes. That dude in row three can not stop screaming about pale ales. The woman in the back seems to cringe every time I think I’m nailing the high note.

As a CEO, you have to focus through the distractions. As a rockstar, your whole life is a distraction.

If (when) a song goes off the rails, you follow the drummer.

You have to have somewhere to look when things go wrong, and the drummer just seems so confident. So why not follow him? As the CEO, you’re out in front, and if everyone behind you is zigging, you can’t zag. Fix it in rehearsal, because once you’re on stage, you’re committed.

Follow the drummer behind you, even if they’re wrong.

If you play covers, everyone knows if you screwed up the lyrics. If you play originals, you can make every mistake sound intentional.

Don’t let your company sound like anybody else. You can have influences, but if you don’t nail the basics and also can’t set yourself apart in some way, then everyone will notice every mistake.

You have to schedule the time in the show when everyone re-tunes their instruments or everything will be completely out of tune by the end.

Update your backend software, plan to address tech debt, and account for depreciation. Otherwise your business will be way out of tune. 

Setting up your gear takes 3x as long as actually playing the show.

Putting in the work and building the company means staying the course and investing in things that take three times as long as you think they will. Ever done a serious data analysis that revolutionized your understanding of your business? I bet it took 95% of the time to prep the data and only a short time to run the results. That’s just how it goes.

Retuning time. Note the expanse of empty cases off-stage.

Decision making in a band needs to have clear structure, just like in a company.

I love a good communist manifesto, just like the next first-year poli-sci major, but there has to be some decision making hierarchy or we end up singing 12 Waylon Jennings songs in a row. In startup-land, RACI has been a leading guide for decision making for decades, and it works the same way in a band. As a reminder, RACI is a responsibility assignment matrix that stands for “Responsible, Accountable, Consulted, Informed.” People’s responsibilities fall into one of those buckets.

Anyone can be the R (responsible) for bringing up a song. The bass and drums are C’s (consulted). The A (accountable) is the singer. if the singer doesn’t want to sing the song deep down, the song will never go over well. Lead guitarists think they’re A’s. They’re not, but it’s important to make them think they are. Horns are I’s.

Drummers don’t really speak English. It’s important that you understand enough of their language to survive, but that’s all.

Drummers use words like bars, tempos and things like one-eee-and-a-two-eee-and-a. They have no idea what the words are. They don’t know what key you’re in. They don’t care. At all.

Plenty of subject matter experts will overwhelm you with their expertise – in engineering, in marketing, in sales, in accounting. You have to understand what they’re saying, but you don’t have to speak it back to them. 

Even if you think you’re singing harmony, you’ll likely end up singing the melody if you’re not paying attention.

It’s easy to get sucked into doing the same thing the person next to you is doing. Pay attention and stick with your game plan.

Banjos are simply untunable and should be avoided at all times if possible. (Ditto for accordions.)

If something looks like it’s better off in a bluegrass band, it probably is. This goes for B2B SaaS just as much as it does for rock and roll.

There’s always someone better than you. That’s not why you play. You play because you love it.

There are a lot of CEOs out there who are better than me. Is it useful to think about that? Probably not. My band and I want to play together, and that works for us. My company too.

A Dream Job

I’m may never land that elusive dream gig in Rio, but I’ve learned a lot (and had fun) playing rock gigs in Denver. And when I come to my real job, I bring those rock star lessons along with me.

Avatar photo

Steve Pockross

As CEO, Steve brings more than 20 years of startup, nonprofit, and Fortune 500 experience to not only running the business of Verblio, but also setting the culture, vision, and purpose of the team. Outside the office, Steve enjoys ultimate frisbee, telemark skiing, hosting jazz concerts, and spending time with his two boys.

Questions? Check out our FAQs or contact us.