A musician and poker player turned into a writer

What if we say some people are worth writing about and yet write something worth reading? If you think about it, the most compelling writers are curious; they move through the world, intending to bring out incredible stories. In doing so, they inspire hundreds and become a story worth telling.


A musician turned writer — Lyle McKeany values experiences; but what makes his writing beautiful is it’s honest, vulnerable, and thought-provoking. He is an active member in various writing communities and works with a few startups as a freelancer and ghostwriter. With an avid enthusiasm in the startup world, he proactively acquaints himself with tech developments, which led to his latest progress: exploring NFTs and collaborating with NFT artists. Another exciting thing about Lyle is he is a former professional poker player and took part in the World Series of Poker in 2006 and 2017. 

Also, Lyle was the bassist at Pressure 4-5 — a well-known American music band that toured and performed widely. In this journey, we'll unearth Lyle's transition from a musician to writer and how his enriching life and adventures add to his writing.


When Lyle was 12, he was obsessed with baseball and wanted to be a professional baseball player. But as he grew older, he began to play the bass guitar while his brother took to drums. The duo would jam together, and music fueled his creativity — despite learning to play the songs they liked, they also wrote new songs.

"When I went to college, I transferred down to UC Santa Barbara and joined a band where we practiced and wrote a lot of new material. The only time we ever played a cover song was during our first show as we had extra time. I loved creating with others, coming up with ideas, and discussing them with the band later. Later, I didn't do anything creative for a while and indulged in career-oriented things to pay bills."

However, he found distinct methods to be creative — like golf and playing poker professionally as it demanded strategic and creative thinking. He recollects using the same parts of his brain while writing, which is a significant part of his life. Even in the band, he wrote a tour diary to send out updates from their road tours; he also maintained a message board to interact with their fans. That's how he stayed close to writing in its various forms.

Life As A Musician

Lyle was still in college when Pressure 4-5 came to life, and he'd skip his classes for band practices and shows. Eventually, when they signed up a management team, he dropped out of school to focus on the band.

"I joked that I could always go back to UC Santa Barbara because it won't fall into the ocean. Soon, we signed a record deal, went on tours, but our first single hit the radio a few days before 9/11, which dampened our promotions. Despite touring and selling albums, it felt like the writing was on the wall, and the label wasn't keen on us any longer. Although they spent a lot on us and presented a two-album deal, we knew they wouldn't honor it."

While that's one end of the spectrum, the band members, too, kept quitting because of lifestyle issues unrelated to music. In due course, Lyle left Pressure 4-5 to join another band based out of Santa Barbara. His brother was already a part of it, and since the band had issues with their bassist, they took Lyle in. Although they got a management team, the band didn't strike any luck.

"In hindsight, I apprehend the music industry's transformation — Napster was getting big, record deals were falling apart, and I wondered why we made no headway despite making good music. Now, I realize it didn't make sense from a business standpoint — nevertheless, we tried for some more years and took a break because the industry burned me out."

Lyle hasn't gone back to music ever since! He still has instruments and often dabbles in music, but that's about it.

Check out Pressure 4-5's music on Spotify

Life Before Professional Writing

For every creator out there, a before and an after is pretty usual. While Lyle always wrote, he still led an offbeat life before writing professionally. Shortly after joining the second band, he began working at a golf course to make money and became an assistant golf pro, where he taught golf lessons. As Lyle got deeper into golf, he realized it wasn’t a lucrative profession — despite loving it, he figured moving on to a better career opportunity would be more practical.

Around that time, Lyle played poker as a side hustle. Eventually, he quit golf to play poker for about two years.

"It was such a weird way of making a living because you're playing others for their money, you know? I played in the World Series of Poker at Las Vegas a few times — it was pretty great but led to a burnout. It also seemed strange because watching people lose a lot of money didn't feel right. Now, I play recreationally online, sometimes."

When Lyle turned 30, he decided it was about time to take up a real job. His wife then worked at an insurance agency, and they moved to Sonoma County. Her office was hiring an insurance underwriter and asked Lyle to take it up; Lyle worked there for five years, and when that agency moved out of their area, he took up a sales job. As a sales manager, he handled a small team and also ran numbers. His company was growing 2% a year, and when he found out Uber was growing 20% month on month, he thought it was incredible. That's what drew him to the startup world, wanting to be involved in early-stage startups.

"I joined a cohort-based school called Tradecraft to study growth marketing, which helped jumpstart my career in the tech world. I worked at an early-stage startup, which another startup bought, and later, I joined another acquired startup. I've been in tech ever since."

Lyle shifted to the tech world as he was excited to build something from nothing. He relished the advantage of working at early-stage startups, which allowed him to influence their creation and put them out in the world. Besides, he was the first marketing hire at one of the startups.

"Being a part of an early startup felt like a risk-adjusted founder's experience — it's just that you gain a similar experience like a founder would by building something from scratch."

But another interesting thing is during his insurance underwriter stint at the insurance agency, he founded a startup with friends. Although it didn't see success, it was a learning curve as he understood the value of acquisitions. He also met driven people, understood the tech industry on a broader level, and experimented with diverse ideas.

Journey Towards Writing

A little before the pandemic, Lyle was working with different startups, doing performance marketing. While the startup was profitable and they kept working on new ideas — things slowed down when the pandemic hit. He wanted to move on to other things; luckily, his wife was earning well enough to give him the flexibility to explore different things.

"I started writing because I sought a creative outlet, but the more I wrote, the more I realized writing could be my job. So, I was writing part-time and spent my remaining time exploring crypto and NFTs. During the pandemic, I wondered what I could do with my time that might not pay off tomorrow but reap something in 5-10 years later. Writing has been great that way — I connect with people I otherwise wouldn't and get better at the craft every day while finding ways to tell stories better and move people with my words."

Lyle wrote tech pieces on Medium and played around with WordPress but stuck to Substack for convenience. He prefers it since it acts as a blog and a newsletter without a fuss like MailChimp. On Substack, Lyle writes personal essays, which are candid and vulnerable, and admits a few memoirs influence him. But he also didn't realize that his storytelling was in memoir-style for the longest time. 

A snippet where Lyle discusses his inspiration to start a memoir-style newsletter.

Growing As A Writer

Lyle made conscious efforts to improve his craft at every step, whether seeking early feedback from his loved ones or joining an On Deck Writer's Fellowship. While the feedback fuelled him to write better, the fellowship introduced him to writers who subscribed to his newsletter and shared their opinions. When Kushaan Shah, writer of Marketing Mind Meld, recommended Lyle and some famous writers in his interview with Substack, it instantly earned him 200 subscribers. 

"I was curious how my writing affected people and tracked my analytics, comments and how people engaged with my content. Now, I receive comments on every post on Substack or through email. People reach out with positive comments saying it reminds them of something, and share their stories too. Even a tiny thing like tapping on the heart button is fantastic; although it takes two seconds, I know it's like a micro communication between my readers and me. And that's huge!"

Stepping Into Cryptoverse

The startup connections that he earned after Tradecraft led him to discover NFT. 

"I am friends with one of the founders, Scott John Howard, who now runs a company that helps with NFT launches; he codes, and while checking out his Twitter profile, I found some cool art. When he added me to a Twitter chat group with people working in the NFT space, I got super curious, asked questions, and got more involved. Originally, I thought I'd find a way to collaborate with an artist using my words. As I hung out in the group more, I learned different things. Recently, I've also bought some art to see what it's all about."

Lyle has some ideas associated with writing, which are a work in progress. Recently, Mirror — a writing platform for writers keen on exploring NFT, accepted him, and he states it took months as it follows a voting system. With a desire to talk to NFT artists, understand their experiences, and do interview pieces on them, we're sure he'll brew some fabulous stories.

A snippet from where Lyle shares his experience with NFTs.

Life Experiments

Lyle's journey exemplifies that he isn't married to just one idea or venture; his life is also an illustration of his creativity and purpose to test and try diverse things. For instance, he has done several podcasts in the previous year, including some small ones.

"When people reach out to me, I'm on board because you never know how things grow. I'm up for anything reasonable — even guest blog posts. I'm also working on something for this newsletter called The New Fatherhood that has a pretty targeted audience for my writing style."

He's also considering his podcast to unfold the adventures of memoir writers and their experiences. With podcasts, he also intends to explore paid promotions, subscriptions, and sponsorships.

Writing As A Habit

Lyle says he cannot force creativity, but he can force himself to write every day. He emphasizes the importance of doing something every day to remain creative; otherwise, it becomes a habit not to create. 

A snippet where Lyle discusses his writing process.

The Way Forward

Writing a book is perhaps every writer's biggest dream, and Lyle intends to write one and earn a publishing deal. While that's his big goal, he is all set to grow his newsletter and audience for the next five years, especially on Substack.

"I grew my email subscribers from absolute zero to 600, and if you picture them in a theater, it appears like I'm performing in front of 600 people every week. I can pick trending topics and change the titles of the newsletter to reflect them, but I don't want to do that. It may be a sacrifice, but I don't want overnight audience growth. I can do whatever I want every week, and I enjoy that freedom."

Indeed, we'll read more inspiring and marvelous stories from Lyle — some will touch our lives, make us slow down, pause, and think about what truly matters.

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