Steve Olsher

Steve Olsher | Reinventing & Dismantling The Status Quo

23 mins read

Podcast Magazine Celebrates 1 Year Of Going ‘Beyond The Microphone’

It seems difficult to believe, but February marks the one-year anniversary of the launch of Podcast Magazine. 

From conceptualization to publication of the first 140-page issue in just 100 days, Founder and Editor-In-Chief Steve Olsher was simply “following [his] instinct” to pursue what he described as a “rebirth of the podcasting medium” happening right before our collective eyes. 

A lifelong lover of radio, Steve says, “The beautiful thing about podcasting is that it gives every person the opportunity to ostensibly have their own radio station—and the cost of entry is extremely low. As a matter of fact, it’s almost zero… and you can reach almost anyone, almost anywhere, at almost any time, simply by clicking a few buttons. I knew back in 2009 that there was something scalable and sustainable to this. Ten years later, the medium really began to hit its stride, and I believed in my heart that the opportunity was before us to go all in.”

Reflecting on the past 12 months as a “fun and interesting trek,” Steve has worked diligently to ensure the magazine provides podcast fans with the chance to go beyond the microphone and deeper into the lives of the podcasters and the stories they love, while introducing readers to shows they likely haven’t heard of but should be listening to.

“Our goal is to humanize the people behind the microphone—to share who they truly are as opposed to simply talking about their podcast,” Steve said. “Of course, we love profiling podcasters who have achieved stratospheric heights, as it adds credibility for the magazine, but what we love even more is helping podcast fans discover shows that may not appear in the charts—which is becoming increasingly difficult as deeper and deeper pockets enter the mix.

“Fact is, we all have something to learn, and everyone has something to teach. One of my favorite expressions is ‘To a second grader, a fifth grader is a God.’ Podcasting is the absolute personification of this, as it allows each of us to help others simply by sharing our respective expertise.” 

Known as “America’s Reinvention Expert,” Steve is a serial entrepreneur who has launched several multi-million-dollar companies, an accomplished real estate investor, and a coach/consultant who has helped countless people across the globe discover their WHAT—more on that in a moment. 

He is also the creator and host of The New Media Summit™—a unique live (and now virtual) event that provides a singular platform for aspiring podcast guests to pitch leading podcasters and get booked on the spot—international keynote speaker, and the New York Times bestselling author of the book What Is Your WHAT? In it, Steve furthers his mission to help people “cultivate a life of purpose, conviction, and contribution by identifying and creating a plan of action for bringing the ONE thing they were born to do to fruition.” In other words, he helps people gain clarity on how they are naturally wired to excel, and then lays out a game plan for sharing and monetizing that which puts fire in their soul.

True to the nature of his work, Steve didn’t become a reinvention expert without first walking the walk. 

Born and raised in Evanston, Illinois, Steve took his love of radio (which he refers to as “the Holy Grail”) and DJing (spinning predominantly Chicago house music) to the next level while forging his path to entrepreneurship by opening his own non-alcoholic nightclub, The Funky Pickle! At just 19, he wrote a detailed business plan, secured a single investor as his partner to fund the venture, and successfully ran the business for over two years. 

Eventually, disagreements with his partner as to the club’s next best steps led to its demise. Steve was undeterred. He’d experienced the perks of entrepreneurship and quickly switched gears, spending the next nine years building a catalog and online business, Liquor by Wire, together with his mom. 

Similar to FTD, Liquor by Wire provided worldwide gift delivery of wine, champagne, spirits, and gift baskets using local retailers. With a penchant for spotting forthcoming trends, Steve led the team’s early initiatives to launch a ‘store’ on CompuServe’s Electronic Mall in 1993, going on to build one of the internet’s first fully functional eCommerce sites in 1995. 

By mid-1999, investment capital was flooding into the tech landscape, and with “the heavy lifting completed, the acquisition of the domain [for $7,500] plus the subsequent name change combined with millions in annual revenue,” and the company was in prime position to fulfill many an entrepreneur’s dream… going public. 

To do so, Steve and his mom hired an investment bank to take them to the “promised land,” and found themselves “completely blinded by the dot com light and its allure of fame and fortune.” This process included hiring “lettered saviors—a CEO, CFO, CTO, WTF, etc.”—and agreeing to sign away their management rights to them—a huge error, in retrospect. 

With a new management team in place, filed its S1 to go public in March 2000. Days later, the market crashed, and with the public markets drying up overnight, the shortcomings of the C-suite hires became evident. Two weeks later, Steve walked away from the company he’d spent nearly a decade building with nothing to show for his efforts. 

The biggest lesson he learned from this experience? “Never allow someone else to take control of bringing your vision to fruition. And that there’s no such thing as failure. Failure is just one of those terms of ignorance weak-minded people like to throw out at those who dare to soar in an attempt to bring them down.

“I choose to view failure as ‘success with an unintended ending.’” 

Forced to find a new WHAT to keep food on the table and the lights on for his family, Steve began his foray into real estate development. With zero knowledge of the landscape, he dove straight in, beginning by rehabilitating small apartment buildings and converting the units into condominiums. These initial efforts evolved into the redevelopment of retail, office, and mixed-use properties, and Steve eventually amassed a portfolio that exceeded $50M in transactional value. 

And then… the real estate crash and economic collapse of 2008 rocked his (and nearly everyone’s) world. Pushed to the brink of bankruptcy for a second time in less than nine years, he was forced to, yet again, find a new WHAT

His next act? Helping people reinvent their lives, discover their WHAT, and guide them to avoid many of the same trials, tribulations, and “brain damage” he had to endure over the course of his career… and life. This led to uncovering his love for, and previously untapped skills in the fields of, writing, speaking and coaching. 

“I realized that, if I can help others reinvent their lives and discover their WHAT, and they then go out and make this world a better place, it ultimately makes my world better, too… as well as my wife’s, our kids’, our family’s, and so on. There is a powerful ripple effect that I can help put into motion with a single action. 

Steve Olsher
Steve doing an interview about his New York Times bestselling book, What Is Your WHAT?

“If people are struggling with their WHAT, it’s nearly impossible for them to recognize that they are the solution to someone else’s problem. Everyone has something to teach, and each of us can serve humanity in our own singular, unique, powerful way. And, when people are able to understand how to leverage and monetize their WHAT, they become unstoppable forces who are able to create a life they truly love.” 

Now, one of Steve’s primary missions is to give people the tools they need to reinvent their life: first, by helping them identify how they’re naturally wired to excel, and then, by showing them how to get paid extraordinarily well for what comes as naturally to them as breathing. 

I am one of the few coaches who has actually built businesses outside of the coaching world. All the experiences I’ve had as an entrepreneur and, now, in building a personal brand, have allowed me to create, and follow, the profit path we’re currently focused on.” 

Reinvention Radio Cover ArtThis path launched Steve directly into the world of podcasting in 2009. Having bought radio time on a small AM station in Chicago for his new show, Reinvention Radio—“where ‘normal’ comes to die; ‘mediocrity’ meets its final demise; and ‘the status quo’ is unabashedly dismantled”—he quickly realized that the only people who would hear him would be those tuned in to that exact station at that exact moment in time. He began to understand the inherent value of podcasting. 

“With a podcast, almost anyone, nearly anywhere on the planet can listen to your show at any time they choose on their preferred device,” Steve said. “And that’s certainly the goal of most podcasters—to reach as many people as possible with their mission and message.” That same year, Reinvention Radio became available solely as a podcast. 

While Steve admittedly succumbed to “podfade” after approximately 30 episodes, the podcasting fire continued to burn within. In 2015, he fully committed to releasing episodes on a weekly basis alongside his new cohosts Mary Goulet and Richard Otey. Within three weeks, Reinvention Radio hit #1 on Apple as a “New & Noteworthy Show” in Society & Culture. 

In 2018, the trio achieved similar accolades with their second show, Beyond 8 Figures. Given the show’s focus on sitting down with entrepreneurs who had either sold their business for more than $10,000,000 or were currently running a business that was grossing more than $10,000,000 annually, the show was originally conceived as a mechanism for building a Rolodex of high net worth contacts. In 2020, Steve made the choice to sell the show. While terms of the transaction have not been disclosed, the total compensation value has been reported to be north of $100,000. 

Referring to both shows, Steve said:

“We realized quite quickly that, for us, it wasn’t about downloads or numbers. We weren’t after Top 10 shows, and we weren’t looking at our podcast as a business, per se. Instead, we sought to leverage the ‘business of podcasting.’ Our shows provided us with a vehicle to connect with people I wanted to connect with—to gain the credibility and authority that would enable us to teach others about the medium of podcasting. We were also able to leverage them as lead-generation mechanisms, attracting ideal prospects who are perfect candidates for our products, programs, and services. Having that clear understanding of what constitutes a win for us was vital.”

So, how did all of this lead to Podcast Magazine, you might wonder? 

According to Steve, the fundamental question every entrepreneur must be able to answer at each stage of his or her business’s life cycle is: 

“What conversation do I MOST want to be part of?” 

“The goal is to be able to answer this question in one or two words and, ultimately, for your (or your company’s) name to be part of those conversations even when you’re NOT in the room,” Steve said. 

“When we determined that ‘podcasting’ is the conversation we most want to be part of, we had to figure out how to make that happen. Even though we had been releasing podcast episodes on a consistent basis since 2015, based on the merits of the podcast itself, we knew we weren’t going to be in that conversation as our numbers were nowhere near Rogan’s or the deep-pocketed companies entering the industry on a daily basis. 

We had to figure out what we could do to sit at the hub of the podcasting industry. In other words, if you think about how a bicycle wheel operates, all of the spokes connect to a center hub. That’s ideally what you want to achieve—having the myriad facets of the industry all connect to you and aspire to be involved with your organization. 

Steve Olsher & Kelly Poelker
Steve with his President & COO, Kelly Poelker, at the Podcast Magazine Launch Party

“And for us, that answer is Podcast Magazine. When we examined the total available market, we determined the biggest opportunity would be in catering to podcast fans. When I was first struck with the idea in October 2019, there were roughly 75 million people over the age of 12 in the United States who listened to podcasts on a monthly basis. Compared to the 800,000 podcasts available via Apple, of which less than 25% had more than 10 episodes and were actively producing new content, there was no question in my mind as to what we should do. 

“So, we focused our efforts on serving podcast fans and creating a beautiful, well-produced publication. We had strong confidence that if we could create the equivalent of Rolling Stone, Sports Illustrated, or Wired in the world of podcasts, we’d accomplish our objective of positioning ourselves at the epicenter of the podcasting conversation.” 

With nearly 40,000 subscribers signing on in less than 12 months, the magazine has hit many of its first-year milestones. Never one to rest on his laurels, though, Steve has his company’s sights set on a much bigger prize: bringing Ear Control—an end-to-end, vertically-integrated media and technology enterprise focused on capitalizing on the emergence of audio as a primary platform for the consumption of information, education, and entertainment—to fruition.

“Ear Control is the parent company of Podcast Magazine, and there are four distinct pillars. Pillar 1 is the media arm. This includes Podcast Magazine, our email list, web traffic, and social following. Pillar 2 is our network of podcasts, including The Hot 50 Countdown, our forthcoming show Beyond The Microphone, and additional shows slated for release in 2021.

“Pillar 3 includes our online event, The Virtual New Media Summit™, and our brand-new, in-person event, PodXpo™, which will ostensibly be the ‘Comic-Con’ of podcasting. And Pillar 4 is our technology arm. We’re in the process of developing an app to help with discovery as well as a podcast valuation tool and marketplace for the buying and selling of shows.

“It’s all very circular, and the synergies are evident. The magazine feeds the shows; the shows feed the technology; the technology feeds the event, etc. Each is very complementary to the other.”

Entrepreneurship has provided Steve with myriad benefits, but he is quick to point to the greatest by far: enjoying more time with his family. This father of three has been able to work from home almost every day of his children’s lives, and he hopes he is passing down the value of time freedom to his sons. 

Steve & Lena Olsher
Steve with his family (from left) son Isaiah, wife Lena, and sons Xavier and Bobby

Married to his wife Lena since 1997, Steve credits the success of their marriage to several factors: 

“First, we make each other laugh every day. My wife says we are each other’s clowns. Second, there is a LOT of mutual respect. We allow each other to be who we are, not who we wish the other person was or, in our minds, should be. 

“We’ve come to embrace the fact that we look at things differently, through our own eyes and perspectives based on the data we’ve individually received over the course of our lives. What I believe to be true doesn’t make me right, and it doesn’t make her wrong, or vice versa. And we recognize that we each have expertise in certain areas that we can teach to the other. Lena teaches me every day, and I’m a willing student. Helping each other grow is definitely key.” 

So, what’s next for this motorcycle-turned-jeep-loving Brazilian Jiu-Jitsu brown belt… and Podcast Magazine

“I’ve still got a lot more to give to this world,” Steve said. “I’m taking it day by day, doing whatever I can to maximize the time I’ve been blessed to receive. And, today, I’m more aware than ever that life, and our time on this planet, is fleeting. 

“COVID has reinforced that for me, as well as Lena’s role as a funeral director and embalmer for over a decade. The families she serves are not always saying goodbye to someone who has lived well into his or her senior years. It reminds you how precious life truly is, and that every day is a gift.” 

To help serve those having to contend with one of life’s most difficult times, Steve and Lena are nearly finished with their construction of Bravo Family Mortuarythe first new full-service funeral home to be built in San Diego in nearly 60 years… and their first foray into working collaboratively. 

“It’s not lost on us that my work is focused on helping people create an exceptional life while they’re alive; Lena’s is to ensure exceptional end-of-life celebrations,” Steve said. “We’re both fortunate that we’ve been able to create careers that allow us to do what we love. If that’s not the definition of success, I don’t know what is.” 



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