I’ve always been fascinated by stories of entrepreneurs who start something, watch it struggle, and then have the guts to make a change that turns everything around. Michael DeAloia, the CEO of Evergreen Podcasts, is one of those people. I had him on my Never Been Promoted podcast, and what struck me wasn’t just the success he’s built but the tough decisions he had to make along the way. This wasn’t someone who just happened to get lucky. Michael’s success came because he knew when to let go of what wasn’t working and lean into a new direction.
In our conversation, Michael talked about how he took Evergreen from a shaky start—barely any downloads, a clunky brand—to a network with over 350 shows and millions of downloads. His journey offers a lot to learn, especially for those of us who’ve hit that point where we know something has to change, but we’re not sure what or how.
Let’s break down two key lessons from Michael’s story…
1. When to Pivot (Without the Panic Button)
We’ve all been there, grinding away at something that just isn’t clicking, hoping that if we push a little harder, it’ll magically start to work. Michael didn’t let himself get stuck in that mindset for long. Evergreen was originally called “Front Porch People,” and the whole idea was for podcasts to be this family-gathering, radio-style experience. Spoiler: It didn’t work.
Michael admitted, “The brand we inherited was a bit stale. The podcast design was elementary. We threw content out there like spaghetti against a wall, hoping something would stick.” After a rough first year with only 18,000 downloads across a handful of shows, he knew they needed to do something different. And fast.
Key Takeaways from Our Discussion:
- Don’t wait too long: Michael said it best: “I could have cut the pivot time from 18 months to nine.” It’s tempting to hold out hope that things will improve, but being able to recognize early that something’s off can save you a lot of time.
- Find the right help: Bringing in a branding expert like David Moss was a game-changer for Evergreen. “Sometimes you need a fresh set of eyes,” Michael said. It’s okay to admit you don’t have all the answers and bring in people who can help fill the gaps.
- Pivot doesn’t mean start over: Michael didn’t burn the house down. He took what was working and shifted the model. The original shows were revamped, the brand became Evergreen, and the team started signing partner podcasts, which made all the difference.
2. Building a Strong Team (And Keeping Them)
One of the best parts of talking to Michael was hearing how he navigated Evergreen’s growth from a small startup to a major player. It wasn’t just about him—he’s the first to tell you that. “We had the right creative team,” he said, but even with the right people in place, there were still challenges. In fact, they almost lost everything when a key executive burned out and left.
“We saw it coming,” Michael admitted. “He was warning us, and we didn’t take it seriously enough.” It was a wake-up call that led to restructuring the team and hiring two new people to take over. The lesson here is that burnout doesn’t just affect one person—it can ripple through an entire organization if not addressed early.
What I Learned from His Experience:
- Listen to your team: When someone on your team says they’re overloaded, listen. “We could’ve avoided a near-meltdown if we acted sooner,” Michael said. Don’t wait until someone leaves or breaks down to take action.
- Find the right roles for the right people: After that key executive left, they realized they had put too much on one person’s plate. The solution? Split the role and make it more manageable. Sometimes it’s not about the person but the role they’re in.
- Your team is your biggest asset: Michael said, “Our team saved us. We hired the right people, and they stepped up when we needed them most.” At the end of the day, it’s the people around you that will either make or break your company’s success.
3. Reflections from the Interview
Reflecting on Michael’s story, what really stood out to me was how much of success comes down to self-awareness and communication. Michael wasn’t afraid to admit when something wasn’t working, and he wasn’t afraid to ask for help when he needed it. This kind of humility isn’t always easy, especially for entrepreneurs who often feel like they have to have all the answers.
Here’s What I’m Taking Away:
- Don’t be afraid to pivot: You know when something isn’t working. Don’t let pride keep you from making the change you need to.
- Act fast on burnout: If someone on your team is showing signs of burnout, take it seriously. It’s easier to fix a workload problem than to replace a key person.
- Surround yourself with smart people: Michael leaned on experts like David Moss to take Evergreen to the next level. Don’t try to be the hero—build a team of heroes.
- Listen more than you speak: Whether it’s your team or your customers, the best entrepreneurs are the ones who know how to listen and act on what they hear.
- You don’t have to do it all yourself: This might sound obvious, but it’s easy to forget. Michael built a network of people who had strengths where he had weaknesses, and it’s a big part of why Evergreen is thriving.
Final Thoughts
Michael’s journey with Evergreen reminded me that entrepreneurship isn’t a straight line. It’s messy, unpredictable, and often full of pivots. But the one constant is that you have to be willing to adapt, whether that means changing your business model or reshuffling your team. And through it all, the most important thing is to keep communication open—with yourself and with your team.
If there’s one thing I’d want you to take away from Michael’s story, it’s that no matter how long you’ve been at it or how successful you think you are, there’s always room to pivot. There’s always room to get better. And there’s always room to learn.
For more insights from Michael DeAloia and a deep dive into his entrepreneurial journey, make sure to check out the full episode of Never Been Promoted: Original Content vs. Partner Podcasts: Finding the Right Balance with Michael DeAloia
CONNECT WITH MICHAEL DEALOIA:
Website (Company): https://evergreenpodcasts.com/
LinkedIn: https://www.linkedin.com/in/techczar/