Podcaster Profiles: Greg Wasserman -- True Friend Of Indie Podcasters

 There are some people who are born for their job. That doesn't mean they didn't work hard to get and keep that job. It simply means that their personality and behavior appears to fit the job like a key into a lock. 

That's the case with Greg Wasserman, who is the Chief Relationship Officer for RSS.Com. If you're not familiar, RSS.Com is a podcast hosting platform offering tools for creators to host, distribute, monetize, and grow their podcasts, providing features like unlimited storage, automatic distribution to major platforms, customizable players, analytics, and even audio-to-video conversion for platforms like YouTube. The service aims to be an easy-to-use, all-in-one solution for both new and experienced podcasters, simplifying the technical aspects of podcast management. 

Greg is ideally suited for that important job. When you meet him, his smile can light a baseball stadium for a night game. He locks in on you, making eye contact, making what you say important to him, and, maybe most critical, he is a terrific listener. 

In today's Podcaster Profiles, we delve into the podcasting and personal life of Greg Wasserman and discover what does a Chief Relationship Officer do and how do you become one.

We started, of course, at the beginning and asked him about growing up.

"When I was growing up, I wanted to be an athlete, specifically, a soccer player," says Greg. "I played all kinds of sports when I was younger and always thought that's what I would end up doing. 


The idea of playing soccer for the U.S. World Cup was incredible to me. However, over time, I realized that a combination of injuries and not putting in the necessary work ethic had derailed those dreams. I had a lot of natural talent, but injuries kept getting the best of me, so I never got to pursue it further. So while being a professional soccer player was the dream, it just wasn’t going to happen."


With Greg's soccer dreams put on hold, we wondered how he got into podcasting.

Greg explains: "My path into podcasting wasn’t linear. It was built on relationships. I started in media sales, spending 15 years in the industry at places like Yahoo! and CBS Radio. When CBS acquired Eventful, the company I was with, I suddenly found myself part of a huge sales organization. A lot of my existing clients were already spoken for, so I naturally gravitated toward podcasting, an area CBS was just beginning to figure out. I had the chance to learn directly from people like Thomas Mancusi, who was running the podcast department, and that opened my eyes to how powerful the medium could be."

Greg continues: "Fast forward a few years, and I was working for a mobile apps company, Maple Media, that acquired three podcast apps, Player FM, Breaker, and Podkicker. On my first day, my founder told me, 'Go figure this out.' I didn’t know where to start, so I picked up the phone and began calling hosting companies. I realized that rather than us trying to manually scrape Apple Podcasts, it made way more sense to get in contact directly with the hosts. That decision, again rooted in building relationships, led to partnerships where podcasters could instantly distribute their shows to our millions of listeners. It deepened my understanding of how creators grow and market their shows."

Greg's employment saga continues: " From there, my job became a mix of Jerry Maguire, where I was calling podcasters, whether they were in networks or doing solo shows, and asking how I could help them grow their audience using the platforms we had. This process got me deep into the weeds of how shows market themselves, how important packaging, titling, and descriptions are, especially if you want your show to stand out in an app and get clicks. I built out the strategy where we had an ad unit allowing podcasters to promote their show natively to our millions of users. It became a million-dollar business, and in my opinion, it is still one of the best ways to promote your podcast and grow it. And allowed me to understand that audience growth is a mixture of paid and organic."

After Greg left Maple Media, he ended up joining a bootstrapped startup, Castmagic, where the focus shifted from just podcasting to the broader idea of turning any conversation into content by repurposing recordings for all sorts of uses, not just downloads. The founders started Castmagic to serve the needs of their own podcast. There, Greg got to help creators understand how to build an audience wherever they are, not just focus on downloads with their podcast. 

Greg notes: "It’s been an instrumental part of what I can teach and consult on."

"Now, at RSS.com as Head of Relationships, I get to bring it full circle, educating podcasters, creating partnerships across the ecosystem, and championing one of the largest hosting companies in the world. Along the way, I’ve guested on over 100 podcasts, and I’ll be hosting one soon to round out the journey."

Greg shares what he loves about this job. "At the center of all this, for me, is the belief that Life is about Time and Relationships. Every opportunity I’ve had in podcasting has come from investing in people, building trust, and creating win-win partnerships. That’s also why I love this space so much, as the podcasting community thrives on helping and supporting one another. It’s not just about downloads or ads, it’s about relationships, and that’s what keeps me inspired to do this work every day."

At Ear Worthy, we have so much respect for Greg's job because he essentially helps indie podcasters through RSS every day.

Greg tells us: "One of the biggest mistakes I see indie podcasters make is unintentionally training their listeners to skip ads. Phrases like “We’ll be right back after this message” are basically a signal for the audience to hit that 30-second skip button. Over time, that behavior erodes the value of ads and hurts your chances of keeping sponsors."

Greg continues: "Another issue is misunderstanding how programmatic ad insertion works. Many podcasters don’t realize that ad slots aren’t always filled. So if you hype a commercial break and nothing gets served, the listener’s experience suffers. And if an ad does get served but listeners are conditioned to skip it, advertisers don’t see conversions. That’s when sponsors decide not to come back, which creates a frustrating cycle of constantly chasing new deals."

Greg resets the landscape for indie podcasts.
"The truth is, landing a sponsor isn’t the finish line; it’s really the starting line. Your real job is to create a listening experience that keeps your audience engaged while also helping the brand see results. Most advertisers aren’t just looking for awareness; they want listeners to take an action. That only happens if the podcaster integrates ads in a way that feels authentic and natural to their show."

We asked Greg about the pitfalls of the podcasting industry as it is structured today.

Greg responds: "One of the biggest pitfalls in podcasting today is the overreliance on ads and sponsorships as the only path to monetization. The industry narrative is grow your downloads, get sponsors, and that’s when you’ve “made it.” But that’s just not realistic for most indie podcasters, and in many ways, it holds creators back."

Greg offers advice: "Part of the issue is education. Many podcasters don’t even know what CPM means, let alone how to make those numbers work. Having come from media sales, I know firsthand how much effort goes into chasing sponsors, delivering campaigns, and reporting results. Yet the ecosystem continues to push ads as the default solution. The reality is, there are dozens of other revenue streams like live events, memberships, courses, books, merch, and consulting that often align more naturally with what podcasters are already doing. Ads are just one piece of the puzzle, and ironically, they get outsized attention because they make podcasting easier to compare to other media channels that command big ad budgets, even though those other channels don’t offer the same breadth of monetization opportunities."

The real opportunity is helping podcasters think about monetization through the lens of relationships," notes Greg. "Your podcast creates trust and connection with your audience, and that trust can open doors to revenue streams that feel more authentic than dropping in a random ad read. When podcasters align monetization with the value they already provide to listeners, it becomes sustainable."

"I’ve seen this across the industry from working with advertisers on the media side to partnering with indie creators on platforms," says Greg. "The shows that thrive aren’t the ones chasing just CPMs; instead, they’re the ones getting creative, diversifying income, and focusing on their community. That’s also why I think the industry’s $2B number is misleading, as that only reflects ad dollars. If you look at the broader economic impact of podcasting, it’s far larger." 

Greg then offers wise counsel to indie podcasters.
"This is where my background in ad sales really shapes my perspective. I’ve seen countless advertisers churn through shows because they weren’t getting ROI. The podcasters who succeed are the ones who think about ads as a relationship with their listeners (by respecting their time and trust) and with their sponsors (by driving results). When you treat both sides like relationships to nurture instead of transactions to complete, you set yourself up for repeat business and long-term success."

We then asked Greg about his employer, RSS.Com.How can RSS.com help indie podcasts in ways the large podcast networks cannot or will not? (Note: Ear Worthy will be publishing an article on RSS.Com)

Greg's enthusiasm when talking about RSS.Com is evident. It's obvious that RSS.Com is more than a job and a paycheck. He evangelicizes indie podcasting for those in need.

Greg observes: "When it comes to how RSS.com can help indie podcasters in ways that the big podcast networks can’t, or won’t, I think there’s actually a misconception at the heart of that question. It’s not so much a divide between indies and networks, because RSS.com actually has a network plan, where one account can host as many podcasts as they want, with tons of bells and whistles, such as a collaborator function, IAB-certified analytics, audio-to-video conversion technology, robust reporting, and more, with one low monthly price. Both indie podcasters and podcast networks can host their shows with RSS.com. While we don’t yet offer every single feature some large networks might require, we’re building toward that, and the core tools are already there for both groups."

Greg says: "Where RSS.com really stands out, though, is in giving creators, whether they’re indies or part of a network, easy, accessible ways to monetize. For example, with just 10 downloads a month, anyone can start using our programmatic ad solution and begin making money from their podcast. Plus, we offer a 70/30 revenue share split, so the majority of the revenue goes back to the creator. That’s better than a lot of other hosting companies that are still doing a 50/50 split."

Greg brings it all home with the company's mission.
"Our philosophy is about putting people over profit. We’re focused on providing more profit, more opportunities, and more solutions for indie creators, and also giving the same advantages to larger shows and networks. It’s about making podcasting accessible and rewarding for everyone. That’s how I see RSS.com really helping indie podcasters in a way that’s hard to find elsewhere."

We then shifted to Greg's non-work life to calm him from his impassioned discussions of supporting indei podcasters via RSS.Com. 

We asked: What do you do for leisure when you're not at work? Sports? Travel?

Greg tells us: "Outside of work, I really try to soak up everything Los Angeles has to offer. Living in Hollywood means I’m surrounded by live entertainment, like comedy clubs, legendary concert venues like the Hollywood Bowl and the Greek Theatre, and plenty of smaller spots where you can catch incredible live music. There’s nothing quite like the energy of a live crowd, and that experience really feeds me."

Greg continues: "Travel is another big passion. Living in LA, I love that within a six-hour flight or drive, I can be in so many different places, from wine country in Paso or Sonoma, to national parks and mountains, or hopping down to Latin and South America. Those trips often become a mix of adventure and reconnecting with friends."

Greg then pledges his sports allegiance. " Born and raised in Chicago, sports also play a big role in my life. I went to the University of Southern California (USC), and I’m still a season ticket holder for football, so during the season you’ll definitely find me at the Coliseum cheering on the Trojans. Fight On!"

 

 We ended with Greg where we started. With relationships. Clearly, you can see that for Greg Wasserman, relationship building isn't only a job, it's a lifelong passion. 

 Greg even emphasizes that point. "But above all, it comes back to relationships," Greg inisists. "Whether it’s grabbing a drink with friends in LA, catching up with people I’ve met while traveling, or just spending time with the people who matter most, I prioritize shared experiences. I believe life is about time and relationships, and that guides how I spend my time outside of work. Maybe it’s also the millennial in me."

We finished by asking Greg if he would ever start his own podcast. 

Greg thinks about it and answers: "When it comes to starting my own podcast, I’ve given it some real thought. With my background in podcasting and media, I often teach and coach people that podcasting is the best business development and content marketing engine out there. I honestly believe that businesses should have a podcast, not because of the download numbers or the quest for ad dollars, but because it’s a powerful way to build relationships with your guests and expand your network through the audience you reach and the connections you make.

"That’s why I’m actually contemplating starting my own podcast. Since I work at RSS.Com, I think it’s important for me to truly understand what podcasters go through, using the platform myself and really drinking my own Kool-Aid, so to speak. So yes, be on the lookout. I plan to launch a podcast, hopefully by the end of 2025, or at the latest by 2026."

Greg could not end the interview without one more pitch for indie podcasters to consider RSS.Com. I concur with Greg. For indie podcasters, keep control of our show, which is your business. Use RSS.Com.

"If there’s anyone out there who’s been on the fence about starting their own podcast, I’d invite you to come join the RSS.com podcast hosting family and be a part of my podcasting journey. You’ll get the support, training, and resources you need to start, grow and monetize a show. New podcasters can get three full months free using this discount code: FRIENDS"