Never Been Promoted Podcast

"Podcasting's New Frontier": Michael DeAloia on Innovating the Audio Space

March 14, 2024 Thomas Helfrich Season 1 Episode 27
Never Been Promoted Podcast
"Podcasting's New Frontier": Michael DeAloia on Innovating the Audio Space
Never Been Promoted
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Never Been Promoted Podcast with Thomas Helfrich

Join us for an inspiring episode of Never Been Promoted as Thomas Helfrich sits down with Michael DeAloia, the visionary CEO of Evergreen Podcasts. In a candid conversation, Michael shares his journey from a tech entrepreneur to leading a podcast network renowned for its creativity and expansive growth. This episode is a treasure trove of insights on innovation, leadership, and the art of steering a company through transformative changes.

About Michael DeAloia:

Michael DeAloia has a diverse background that spans venture capital, investment banking, and launching successful tech startups. After selling his tech company and contemplating a quieter life, Michael's path took an unexpected turn when he was presented with the opportunity to lead Evergreen Podcasts. Under his leadership, Evergreen has transformed from its humble beginnings into a significant player in the podcasting industry, achieving millions of downloads and continuously expanding its content portfolio. Michael's strategic vision is complemented by his commitment to fostering creativity, nurturing partnerships, and maintaining a keen focus on both personal and professional growth.

In this episode, Thomas and Michael delve into:

  • The Transformation of Evergreen Podcasts: Michael discusses the strategic decisions behind rebranding and repositioning Evergreen Podcasts, highlighting the importance of adaptability and visionary leadership in the podcasting industry.
  • Cultivating Partnerships: Dive into the world of partner podcasts and how Evergreen Podcasts has built a collaborative network that empowers creators while driving the network's growth and reach.
  • Leadership and Growth: Michael shares valuable lessons on balancing ambitious professional goals with personal well-being, emphasizing the significance of strong relationships and self-awareness in navigating the challenges of leadership.
  • Looking Ahead: Michael outlines his ambitious vision for Evergreen Podcasts, focusing on audience expansion, content acquisition, and innovative monetization strategies.

Key Takeaways:

  • Strategic Flexibility: "Don't take wild risks; minimize them." Michael stresses the importance of strategic thinking and risk management for entrepreneurs aiming for long-term success.
  • The Importance of Culture: Michael reflects on creating a supportive and creative company culture that values collaboration and open communication, essential for driving innovation and adapting to industry changes.
  • Future Aspirations: With a goal of reaching 150 million downloads, Michael is committed to scaling Evergreen Podcasts by leveraging partnerships, enhancing the network's content offerings, and exploring new revenue opportunities.

"Find your outside board of advisors, the people you trust implicitly. We all have ego, ID, superego. How do you manage that?... The entrepreneur has to be a diplomat whether they want to or not." - Michael DeAloia


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Welcome to the Never Been Promoted podcast with Thomas Helfrich. Get ready for a thrilling adventure as we uncover entrepreneurial journeys and life changing business insights every week. And now your host, Thomas.

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Welcome to the Never Been Promoted podcast once again. This is Thomas Helfrich, your lovely and delicious looking host today. That's right. I got a very fine haircut from a barber shop tonsorial here in Alpharetta, Georgia. So if you need a good haircut, they are not promoting it, but honestly, it's the best haircut I've ever got. If you're just listening to this, just imagining how good I look right now. Just kidding. Of course, if this is your first time visiting, that was probably awkward. And I will give you five dad points for just listening to this point. Even if you've been here before, nothing probably is shocking to what I'm saying. We're going to go on an entrepreneurial journey with the guest today. And as we navigate through this, the whole idea is just try to find one thing you can learn from the guest, one thing to help unleash your entrepreneur. And this is a whole movement of entrepreneurs helping other entrepreneurs. And so thank you for so much. Just taking a few moments to listen and or watch. And let's meet our guest, Michael DeAloia. You said earlier and I butchered it. That's actually, I love butchering last names so I can sound American as possible.

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You got close. It's dialloya. And although in Cleveland, Ohio, we've got this unique split, the coyoga splits the city in two. Right. And on the east side of Cleveland, a lot of Italians. And my name's Italian, so Dialloya. On the west side, a lot of Puerto Ricans, Nicaraguans, so they pronounce it de la Hoya. I answer to both, just to be clear. But it is de Alloya, I was.

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Thinking it's like a sauce name. And that's what came to mind when I said it.

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Absolutely. Of course that's what you think of when you hear my name. Gravy sauces.

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I mean, you're saucy. You're the CEO of Evergreen podcast, and we're going to talk about your journey through to get to this point. But do you want to just take a couple of moments to kind of set the table a bit with your background and how you got to where you are today?

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For sure? I'd be happy to. Thomas, before I joined Evergreen as CEO, I had just sold a tech company. I was on the proverbial beach, right. And we just had a daughter, my wife. And so I was thinking about, I'm going to ride this out for a few years, just kind of camp out, got the kid good to go. But I got a call from a friend of mine who's like, hey, man, I just interviewed for this job, and I'm not the guy, but I told him I knew the guy, knew the guy. So you need to call. At the time, it was Joan Andrews. You need to call Joan Andrews. And I did, and I'm speeding up the story. But I eventually became the CEO of Evergreen podcast. She had started the podcast business underneath a different brand name a few years prior, was looking to get more serious about it. She is the funder founder, but she wanted an entrepreneurial expert or someone who's been deep diving the entrepreneurial waters to run the business. And it's an unusual conglomeration where you get the funder founder through her family office, really providing the dollars for us to grow. And she's hired in a completely outside executive team, and now we're also owners, the executive team. So it's not your typical venture model that you would generally see in a startup, but rather an family office structure. So it's an upside down cap table with that regard. But it works. It is the craziest philosophical mismatch I've ever been a part of. But it just flows, you know what I mean? So that's how I got involved. Prior to that, my first job out of grad school was with a venture capital group. Then I did a tour with investment banking, then started a number of tech companies. That's where I'm pretty well known, in Cleveland at least, of starting and selling off a couple. No home runs, singles, doubles. We're batting better than average on the exit stream. But like I said, it's working out. And all of my past, being in a VC fund, being in investment banking, starting a number of companies, kind of helped me weather the strategic storm on how to build a company like this. Literally when I started it was two interns myself, four shows that needed a lot of work. The website was, to be frank, awful. And that first year, Thomas, I think about this quite a bit. Our first year, we did the four shows, 18,000 downloads total. I should have been fired, quite frankly. And then last year, 350 shows, almost 31 million downloads. We're slowly becoming what I would call a middle market or a Jan Brady style podcast network.

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That's amazing. That's a huge number. You say mid, so. All right, so your background is obviously, you've ran some stuff. You've built some stuff. And I take singles and doubles all day. They go faster.

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Me, too, for sure.

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Right. I agree with you, but come back to that a bit. So how in the world are you calling some 31 million downloads and maybe give me an idea. It's not one show, but tell me you have a conglomerate of podcast. Tell me about what the business is a bit, because I want to get into what you've learned along the way and what you're learning today about that business as well. So take a few moments to talk about the Evergreen podcast business.

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Well, we tried original programming for the first two years of the business, and it is, as you know, just genuinely difficult to craft from scratch. A huge hit in the podcasting world. I mean, there was a period of time, I want to say 24 to 30 months, where the top 20 shows didn't change at all in podcasting. So to break into the top 20 was just impossible. So we thought two things about 18 months in. So we're talking about mid 2018. We decided on two things. We needed to change the original concept of the business. It was originally called Front Porch people. And Joan loves radio. So her initial thought was podcasting should be like the old radio shows back in the, where you gather the family around the podcast and they all listen to it, and they can discuss it afterwards. There's quizzes and all these post listening activities that you would do at the show. And the truth is, podcasting is a very singular endeavor. Right? You're going to listen to it in your car while you're traveling on the jet, so to speak. So that model didn't work and the brand didn't work. What's front porch people? What's that mean? So we decided we're going to be evergreen, which really denotes the style of programming that we want. And it's just really, I think, could have been, could be. At the time, our thought, what was influential as a podcasting brand in the industry. And the second thing we wanted to do was we wanted to start getting partner podcasts onto the network as a way to augment our fledgling original programming. So the growth cycle has been predominantly in the partner podcast. So roughly about 85, 90% of our growth to date has been on the partner side, where we sign a sales and marketing agreement. We become the Jerry Maguire of a podcast. Thomas, you have a podcast, and I would imagine it is a ton of work. And I don't think a lot of people outside of podcasting realize everything you have to do, right? You got to record, you got to edit, you got to then upload, you got to host, you got to distribute, you got to book guests. Then you got to sell your advertising and your sponsorships. You may be doing books and speaking tours. All that just takes a lot of time. And the thought is, we'll handle all of that for you, and you just create the best podcast that you can, and we'll go out and sell it. So, early on, the key show that really proved the model for us with Chad and cheese, which is still in our top 20 shows, once we got them on board, it's been like a magic ride. I have to be frank. I thought early on, our biggest problem being a true podcast network was getting the content on board. That's really been the simple part. It's being able to monetize an ever increasing amount of network shows has been not our bane of existence, but a concern. Now, we've monetized pretty significantly over the last three years. We grow 60% over last year, and we've grown 180% over two years ago in terms of revenue and our distributions out to our partners. And we're only really maximizing about twelve to 15% of our digital ad spots and roughly about 20% of our sponsorship inventory. And we hit seven figures. So you just double that, right? You've got a better universe of financial well being that then can be shared with our partners, and we'll get to this in a few moments. But our 2024 plan really speaks to two things. How can we go out and raise additional capital outside of the family office still supporting us, and how do we drive additional sales through our ever expanding sales network?

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Yeah, it's a great business you guys are running. And I always try to find, obviously, the lessons for the entrepreneurs listening. So if one of the entrepreneur routes you're looking at is podcasting, and maybe just take that angle, right, and you can broaden it to any entrepreneur as the advice. But what you described, there was something wasn't working, and they pivoted, and they don't even evolve. They pivoted a different model, maybe talk about how in your perspective of and you've done tech companies and other pieces, is knowing when to do that. Because I think the lesson, no matter what the business model is, is what you're thinking around knowing when it's not working, so you don't want to keep chasing stupid. There's this weird rift in the world of entrepreneurship where it's like you got to believe in yourself unconditionally and screw everyone else around you to some degree. And you got to just go for it. But there is at some point, you got to go, hey, it's not working shift, so talk about that, because that's the Will Ferrell character in the making. It's like, hey, you're being an idiot about something, but you think you're super smart, versus I truly believe in me and what I'm doing, but this doesn't really seem to be about, because I know it's hard to think through that. And sometimes I think the advice from somebody who's done it a few times might be handy. The floor is yours.

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Thank you, sir.

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You're welcome.

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Luckily, we've had a lot of good, smart people that we brought in, and we realized early on, through a number of discussions and reading the tea leaves and watching the numbers, that the original concept wasn't working. The brand that we inherited was a bit stale. It needed some refreshment. The podcast tile design was elementary. The marketing checklist was pretty non existent. It was like, well, throw out all this content into the ether, and they will come. And that's not how this market works at. So I early on, the discussions with our chief creative officer, David Moss, was like, how do we build a brand for the industry? Because I just knew I had a two or three year cycle of if we broadcast out a brand to the industry, that's fun, irreverent, like a 1960s jazz record label. We take care of our partners. We really make it fun for the acts. We're all about creating great content. We're really supportive of what people want to do for their show, and then for any other additional idea that they have. Let's kind of create that cocoon for the hosts with this overarching brand. That really speaks to just a relegatory statement in the industry. I will say, as a brand, we are very well known in the industry and well respected, but we're not well known or respected in terms of brands, which is where we're pivoting now. So I'll get back to that story in a second. But early on, I was like, the initial brand isn't working. The numbers are going sideways, if not declining. We need to do something radical. David, we brought him on for the very reason of he's built brands. He worked on the launches of BP, launches for british petroleum, for know, the Las Vegas mogul, and all of his properties. So we felt like we had the right creative team. And that brand that we built for Evergreen and now our subsequent brands, like Killer podcast or Pitfast Motorsports, sort of resonate with, these are the things that we want, identity wise and brand wise, and then how does that translate to the sales and marketing side? But it was a pretty easy decision, quite frankly. We're held back a little bit by the family office and founder, and she would tell you the same, because it was her baby, this front porch people concept, and we held onto it too long. I could have narrowed that cycle from 18 months to nine months, and we could have had Evergreen up and running faster. You learn the philosophical makeup of people and how to motivate them. And I was still learning Joan, and Joan was still learning me. Now, again, she's a founder, and typically founders don't really leave the day to day operations. In a lot of respects, she had completely removed herself from the operations of the business, but still held onto it as like, this is my, and rightfully so. This is my baby. I built it. I want to see front porch people succeed. But I have to be honest. Once we switched to Evergreen, which is a more contemporary looking, brand host, specific and centric, it just changed the trajectory of the business, and we've been riding that wave ever since. So it's been a wild ride. But to your point, to pivot, you got to know, give yourself a couple of quarters, you'll know because the numbers will bear it out. And we all have a litmus test. We know when things are going wrong, both operationally, business wise, relationship wise, morally, ethically. We all know we got these barometers, know thermometers that we have, and we can gauge. I wish we had done it sooner. We didn't. I feel like I've got a year or two I need to make up in some respects. And Joan's always saying, no, we did it at the right time, because that was the time to do it. She's very logical and full of common sense. And another thing that I think helped us with that pivot is we would have done it sooner had we had venture capital backing. And I also would tell you, we'd probably be shut down right now if we had venture capital backing. Her family office has just had a much longer perspective in terms of what this investment means. And so she can carry an investment for ten or 15 years, whereas a venture capital fund, really, you've got three to five years to start building critical mass, and you want to sell by seven or eight. And that was a time frame that just wasn't going to work for her.

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Yeah, and you made a good point there. So a lot of entrepreneurs look at bootstrap versus raising money just know that it's great to get money in, but you're going to have a job. You're going to be working for an investor as opposed to building your company. And there's nothing wrong with that. It's just know yourself of what you want or keep the angel investor that just really wants a return when you sell it at some point versus what you just described, which is it's just not going to work for your hypothesis of what was important.

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Thomas, you're spot on. I think when you get an investor in, you need to ask them what's your horizon time wise and what are your financial expectations? Because I think we would have been disappointing for a venture capital investment early on because we just didn't grow as fast as we needed to. We needed some time to. The first two years were keeping the baby alive. When you have a new one, it's like just keep the baby alive until they're a little more sufficient. Right. As a father speaking, the next two years, we're building the brand. That's four years we wouldn't have had that type of patience at a venture capital investment. Now we're doing acquisitions at a pretty rapid clip because the podcast industry is in a bit of a chaos moment. Smart money's leaving, the big brands are being shut down. I never thought in my podcast life that gimlet, for example, one of the big independents, especially when we started independent podcasting networks, would disappear. I mean, it doesn't exist anymore. Spotify run us a separate label for a while and was shut down last year. That's just shocking. So we're in a mode now of, well, let's start acquiring shows and networks that then become our originals. So we're building up our intellectual property on the relative cheap because there's fire sales happening in the marketplace. The money is starting to leave, people are starting to panic a little bit, and we'll just keep the calm in the middle of the storm and we'll just ride it out for another year or two, and then hopefully at the end of that you start to see more exit opportunities than you would right now.

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Yeah, how you're describing, we're definitely new to podcasting and I'm doing this myself, right, is not even my primary. It's not a source of income, it's a. It's a movement. I truly believe that entrepreneurs need to help each other and we need more of them. And some people have taken the path of podcast as a side hustle. Some use it as a marketing tool for their main business. And so it's amazing to see what you're describing because I had no knowledge of you're in that weeds of hey, in this kind of network, all these big players are, it's the same model everywhere. They're acquiring Spotify or Google Podcasts is they're, they're leaving. I think I got a notice the other day, but yet mine's on YouTube, so I'm trying to get my head around that a bit. Maybe that's where they're going to go. Put it is all through YouTube. But the idea that they're acquiring shows and this and that just makes me happier. I'm getting a long winded way to saying that if we do this well, someone wants to buy us, it's going to be great. So I never thought of that as a monetization. In your journey here, though, give me the one learning, maybe optical to any entrepreneur coming up and coming, no matter where they are in their journey, what's the one piece of advice you'd give them?

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This is going to sound a bit contrarian, I think. Don't take wild ass risk. You want to minimize risk as much as possible. And I think the entrepreneurial myth, especially in America, these people have taken these crazy risks at a particular point in time and have made it work. There's a lot of reasons why it worked. And I think the biggest reason why is they were able to minimize the external risk as much as possible, which is a hard thing to do. Second thing I would say is, and this is from my experience after grad school, I have an MBA in finance, and I remember how much I studied for finance, marketing, accounting, all the hard sciences that are engaged in your business operation. These are all things that you can hire experts for or completely outsource, whereas the culture and the spirit, the philosophy of the business is mission critical. So that's the second thing. And the third thing is the human element, which is we all have ego, we all have ID, we all have superego. How do you manage? In our case, we've got an expert group, very distinct backgrounds, all highly educated, all intellectually curious, a bit snarky. That's part of our hiring, is we want a little sarcasm and snark in the snapback in reply, and we can argue all day long, but at the end of the day, when we've made a decision, we all have to implement that decision as a team. And that's a challenge for a lot of people. I'm not saying I'm great at it, but human ego can absolutely destroy an enterprise if you're not all on the same page. And that's investors, stakeholders, internal people. The entrepreneur has to be a diplomat whether they want to or not. I think the most successful ones have the ability to get a large group of people to focus on one mean, you look at the power of Amazon. The guy was selling books online and not very well by the yet, you know, it's, if it's not the largest company in the United States, it's pretty damn close. Amazon touches everything, everything in e commerce, logistics, warehousing, retail. It's a powerhouse. So how do you manage, starting from one person in an office selling books online? It wasn't even the first, by the way. Yeah, in Cleveland, Ohio was the first, and that didn't turn out to be a good story for anybody. So how do two companies that started around the same time have completely different trajectories? You know what I mean?

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Yeah. No, you've hit some stuff. So you've hit some very big stuff, if you will, of outsource the stuff that you can, but don't give away the heart and soul of it, because that's you as a founder, it's you as the entrepreneur. And I think there's some self reflection needs that happen there, too, because I think a lot of people have a tough time understanding why things fail or succeed. And on failure, it's very easy to blame others and not take your own accountability for your own ego, your own attitude, your own add or whatever it is that drives people away. It's very easy to take the credit, though, for the success, of course. And so if you're not self reflective on why things work and why they're not, and not always finding an actual formalized way to evaluate that, you're introducing risks that don't need to be there.

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I think self reflection is so fundamentally necessary for any endeavor, be it business, political, personal journey, whatever the case may be. I just find it an attribute that is less and less evident in our society. Unfortunately, I've had some great successes. I've also had some just monumental failures and a couple of that first blush, you're like, my God, how did this go this way?

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You saw it coming, too. That's the thing. On the failures, you got to know sometimes you're like, I've pretty much felt this coming. And for some reason, absolutely. Now, have you ever let it happen? And this can be on personal or business, but sometimes you see these trains coming at you and you're just like, I'm just going to stand on this train. I don't give a shit. I see it coming a mile away. If someone rescues me, fine. Otherwise, let it hit me. I don't care. I've done this. Definitely on working for somebody. I'm referring to more there. But have you done that where you've seen the train come and you're like, this is the way I'm getting out.

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In my early days for sure. Because we feel like we've just painted ourselves into the corner or we're stuck on the track. And someone was like, I was trying to explain this in life one time to a friend of mine, and I was using the analogy of playing poker. I got a bad hand and this bad hand got me to this point. The guy's like, dude, if you're going to use that analogy, you can lay down your cards, you can change cards, you can switch the game from 357 to Texas holder. And that just blew my mind. Like, wait a minute, I can change it. There are some inevitabilities in business. It's not working. So we're going to have to shut it down. But to be honest with the people that you're working with, the investors that you have and your stakeholders, and just be. It's communication. I harp on this all the time internally, to the point where people, I see them rolling their eyes sometimes, like, all right. It's all about communication. When we have issues internally and they have sprung up. For example, last December of 22, we lost a key executive who was handling a lot for us, and he just got burnt out now. He was warning us, hey, I'm getting burnout. I need help. You need to help me. And initially we're like, we'll get you some consulting. We'll get you into therapy. You can start talking with people. We'll start taking a few things away. But the portfolio was so big that it was crash and burn. We saw it coming and we did little to help. Come January, we had to hire two people to take it over. And so January, February of 22 was a freaking full on, full fledged fire internally, to the point where you're starting to see it externally. And one of my things, like you've heard the NFL talk about, always protect the badge, right? We always want to protect Evergreen from external rumors, innuendo, right. We want to control the narrative externally. This was getting out. Like, Evergreen is in full f**king meltdown. I apologize for cursing. You can edit, you don't cuss.

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Actually, we don't air it. So that's the rule. I was going to just have to drop my own f Bobbit. Thank God you did it, because I would have.

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We're in free fall now. The two people we brought on saved the day, got us onto our sea legs. But I was getting calls from very key partners like, hey, be honest. Are you guys going into bankruptcy? What the hell's happening? And it was all in communication, and that really struck us. Like, we're putting out a weekly email to everybody that we touch. We're going to be honest what we're doing strategy wise and invite people into our strategic planning process. So it could have been the absolute end of evergreen because we were teetering for a few months. It was miserable coming into work and trying to work through this. But once we got the two new people on, and God bless them, because they took on that train and somehow stopped that train and reversed it back on the tracks, it was amazing saving grace from these two individuals. So we had the wrong person. We had the right person in the wrong seat. We didn't correct it. Eventually brought on two additional people to take on that role, split it the way it should have been split, and it's paved the way for great growth for us. Going from January, February to November, December, we're like night and day in the industry. But had we not confronted that failure and started to change the way we did business internally, it really could have been that fatal blow. But again, we learn, I think the military, they call them after action reviews, we just call them internal narratives where we want to sit down, executive team, management team, staff, like, what the hell happened? What did we learn from it? What are the corrective measures moving forward? Because if you're being tactical like a Navy SEAL team and something happens in the field, you only have yourself to get you to extract that team out. You got to be quick and nimble. And I think luckily, we've got a very nimble team who immediately saw what the issues were, put in a 30, 60, 90 day plan, and we just executed. And luckily we got ourselves out of the big muddy, as we called it internally.

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In the reflection, I always try to bring it back to what the entrepreneur can take from that because I think that's what's important here in particular is you mentioned once again, though, a self reflecting moment, and also listening to your team, you said somebody, hey, listen, I'm overwhelmed. I'm overworked. And specifically, I see this in companies that are very profitable. They're not taking care of the people that are getting there or like getting the support. And if greed comes in, we're like, well, I managed to have to hire somebody else. Yeah, but that means you'll keep me. If you value that human, that team member, the self reflective nature of what really matters to you as a company is going to come out right. I don't care. We'll replace them, let them burn out. We'll keep burning through people. Or do we split roles? Do we keep people in place? But you talked through it, you thought about it, you did some after action with it. And that self reflective nature in that culture, I think, helps you evolve correctly. It helps you to actually control the narrative a little bit on the risk that you had mentioned before. And I think if you're a business owner or you're a founder, just know that you might be solo right now, but do some self reflection of the partners you have, the vendors you're using, and really evaluate what's going to work, what doesn't work, what adds value and what doesn't. Just maybe at a. Maybe grassroots, smaller level, at a bigger company, get HR involved, I guess.

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Thomas, you're hitting on something which is self reflection, but you also need input from others. And I've been pretty fortunate that I've got a band of brothers of entrepreneurs and investors who I've done work for or with or aspire to. And listen, man, I'll pick up the phone. I have no compunction of asking for help. Alms for leper, like, hey, this is going south, and do you have some perspective that might help me? And more often than not, they do have some revelation or truth that can really be helpful. So find your outside board of advisors, the people that you trust. In my early days, when I was networking the hell out of my professional life, I must have 11,000, 12,000 people in my Rolodex. But I really kind of boiled it down to, like, 20 or 30 people that I trust implicitly, who I've done work with repeatedly and have had great success with. And those are the people I want to be around with.

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Yeah, absolutely. You got to surround yourself with people, and you're not going to have this right from day one. I think that's a big piece, and you're going to have the wrong people, because as a business starts, the people you start with. I make fun of this in one of my videos. It's not a family. It's more of a sports team. You'll need different players, and unfortunately, sometimes those players are the founders that need to be pulled off the team. And if you're the founder, you mentioned it. Like, you had somebody who said, I need to bring someone else in to do this, and there's a number of reasons why that would happen, but you got to surround yourself with the right people at the right moments and then really be objective as a team of what's going to help us win and serve best. Because if you don't, you're not going to win. You're going to just repeat the same mistakes. Looking just kind of conscious, kind of how we time stuff. I think if I ask you now, kind of like where you are, your time zero, once again, you have a whole future ahead of you, of what you're working on, what's maybe the one thing you're working towards, just individually, as a leader of an enterprise that's growing, what are you doing to prepare for that?

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Well, that's a great question. Personally, I'm going through a bit of a really wonderful revelation, too, where I had to strengthen my marriage for all this. Being an entrepreneur is challenging.

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And I've got a wife who was a partner in a law firm and wasn't really enjoying that life. And so we worked hard over the last couple of years to find her a new endeavor. And she just recently joined a firm as in house counsel, as part of the executive team and in house counsel. She's loving it. She's traveling a little bit more. I have to be more of a dad. I got to have a little bit more flexibility. So really, believe it or not, my marriage has dramatically improved over the last 18 to 24 months. And there's only two things in my life right now, family and the business. Like, I put everything else to the side to be successful in these two things. So personally, it's just a lot of, I got to strengthen the relationships that mean the most to me, and that's my wife and daughter personally. And on the business side, I got to keep building my relationship with Joan Andrews, our founder, with our executive and management team. I got to be more open and aware, and again, I think of it more as communication back and forth and getting the right information at the right time. So that's been very helpful. As for the business, listen, we're going from 30 million to. My goal is 150,000,000 in downloads over the next three years. So we know that I have brought in an interim CRO. You talk about building a team, so we're bringing in a CRO as that one year relief pitcher to get us into the championship, or that starting pitcher who might be able to get us into the World Series. Just top notch guy. And he's agreed to give us a year. And that is real meaningful for us to get more sophisticated on our revenue generation side. So those are the. There's never one thing with me, Thomas, so I apologize for giving a more long winded answer on that. But if you're going to live this entrepreneurial lifestyle, you've got to have balance, I think, personally, which to me is my personal relationships, my spiritual relationships, and my physical relationship with myself. And then to have the business structured in a way where it's a lot of wash, rinse and repeat. Right. So everything has an order to it. Because you can't run a business through chaos. You got to run a business through order to minimize the risks and be successful.

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I love that. So you're focusing on the relationships, and I write this in my book. While you're doing this, you're going to let go of some people and you're going to have to intentionally put some really actually very close to people for you. It could be a friend, it could be a spouse, it could be a child, even. I don't know. If you want to get successful, develop the relationships that are going to help you in that moment and in the near future sometimes, and that's a hard piece. And sometimes you have to come back to it as well. No question about it from that. And the business, like even ourselves, we're growing. For my company, instantly relevant this year is about sops and repeatability in the sales process and the stuff that I would never do, don't want to do. But I think I found a good partner to help me drive through it because our first meeting, the guy was like, hey, do you have a documented workflow? I'm like, no, I do not. And I'm like, because I can't hire salespeople and I can't ever exit being in a business unless I can document and drive a better process. Otherwise, I'm 48 at this point. I'm kind of like, do I really want to be doing the exact same thing ten years ago from now? I will be if I don't document stuff and I don't scale it. So taking that idea that, all right, this is an investment, is going to help make the company more sellable, make the processes more efficient, and actually the customer experience be better, too, because I can give more attention to where it matters. And I think what you guys are doing there and how you're thinking about it is ideal, for sure. Let's transition to this there. So a little speed round for you. Now, there's some questions here. There are wrong answers. I'm not going to tell you which ones they are until after you answer.

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Do I get points for this?

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Oh, yeah. There's always dad points. And if you know where to spend them, your dad. You know where to spend dad points. My kids haven't figured it out. They have billions of points. They're like, where do I spend them? I'm like, we'll discover. All right, question number one, and I ask this a lot, is kind of, what's the must read entrepreneurial business book again?

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I'm going to play a little contrarian, but the creative act by Rick Rubin. So for those who don't know Rick Rubin, he's probably like the mastermind producer in the music world he's worked with right there, right. Beastie Boys. The groups that he's worked with is just amazing. Of course, death jam records and recording. I just look at Rick Rubin as, like, the sage in all things creative, and we're in a creative business, but also how he treats people and how he loves people. I was watching a video of him talking about the Abbot brothers, and I love the Abbot brothers, the great, an american folk band. They're just brilliant. And he was just like, they're just so damn nice. I want to be around nice people. I'm the same way. I don't want to be with negative eye merchants. I don't want to be with jerks. They really are downers on our culture. So we vet people as best as we can, and it's just a good working group. That book just tells you how to aspire to creating a rich life around being creative, and I think that philosophically fits with what we want to do.

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Yeah, that's great. And I'll definitely check that out. Anybody like to follow? On social media, we tend to focus on LinkedIn, but open it up to you of, like, outside of podcasts, maybe content creators or anybody else you really like to keep an eye on.

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Well, I certainly keep my eye on other podcast companies. Glassbox. I was huge fan of glass. Still am. Pineapple street. It's those smaller, mid market podcast companies I just love. And you know what else I really dig? This is going to be a little different. So thank you for giving me the Runway. To answer this question, there are two basic subscriptions that I've joined over the last couple of years, one being lunch club. So I'm a big fan of meeting other people who are like minded, and lunch club is a great way to do that. And then for the industry, pod match, which is how I think you and met, has just given me a whole new venue and perspective on the entrepreneurial podcaster like you, Thomas. Those two things, man, have just fed my love of just people and just connecting with good, solid people. Because, listen, there's a lot of static out in the world right now. There's no doubt about it politically, geopolitically, the wars and the conflict, and it just wears on people, right? But at the core, man, I have met so many just fundamentally good people. And that I think is going to be humanity's saving grace, is getting connected with these really smart, cool people. And both podmatch and lunch club have allowed me to do that mean globally, which has just been.

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Lunch club. I bet I have an account there. I remember I used to do it when I first started the company and hadn't thought about it probably in three years. I'm like, oh, man, that was actually good because you could be very targeted. So I'll have to put it on my add checklist of something else to go do when I get time. It's going to be great, Thomas.

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It's hard, man. Right? Because you only have x amount of time during the week. I do it like on Friday mornings, 930 10:00 it's on the calendar. You try not to move it unless there's something wrong.

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I will tell you, I had a really good last few days of January 2024 during this recording, but my calendar is set. Good. And then I opened up this podcast and we had so much interest on the sponsored level coming in. I had to go to. We started this November of 2023. We've already filmed a year's content and it's 20, man. And I haven't even started my solo episodes, so I have to go eight filmings a week right now to keep up with the demand. We monetized the podcast from day one. We have very few downloads at this point, but the socials on the other side are doing really well because I own a marketing company that I do an omnichannel, and I think entrepreneurs listening sometimes. If you're thinking of podcasting or something else, it's representative and metaphoric that you think you're going to make money like a Joe Rogan. You won't. You'll make money by meeting people that will introduce you to your core business, or they will come on and sponsor, or they're going to come on and be part of another subject or another thing that you're working towards, or if you're like me, I'm just doing more altruistic. And if it works and it breaks even, great, because I truly believe in something bigger for entrepreneurship. The point being is be open to how you monetize something and what the intent is and the value to somebody else not being your value of getting monetized behind it. So just keep an open mind of what your purposes are with it. And my final question, if we say goodbye here soon, not forever, just for this time period, and this is a big one, and if you've answered this is the one you can get wrong. In a w two capacity full employment, have you ever been promoted?

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In my earlier career, many times. And actually recruited out of many companies. I was a bit of a firebrand when I was younger, and then I hit one of those failures and then I haven't a w two really, since that point in time when I hit the wall. And I think, too, I just had youthful hubris and ego, which needed to be reflected and smoothed over a little bit. But I hope I don't fail early on when I came out of NBA school, absolutely. A lot, but not anymore. And I don't want to feel the pressure of the w two because people who have w two s feel that pressure of there's a clock ticking on all of us when we're a w two. Right. And so I'd rather control my own destiny.

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Yeah, you answered it wrong because you got it promoted. That's okay. You can't join the club, but you can look in from the windows and see how much fun we're having.

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Ironically, it's going to go into the vault, never to be seen, ever.

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We'll have you to come out with the podcast. It won't get quite the attention because the idea is that I've never been promoted, but I definitely did some job jumping. At some point you do hit a wall where you become unhirable. Entrepreneurs know this. Once you put the word founder on your LinkedIn or someplace else, you're unhirable. No one is hiring you, ever. You're going to have to change the narrative on your resume if you're going to ever want to go back to the w two world. Because people look at that and go, that's their interest. We're not hiring a person who's. They don't hire entrepreneurs. The companies do not because they don't really do entrepreneurship. They do a lot of control. We're not going to get. That's a different episode to come.

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But that's a good episode because you're right. Companies have hired entrepreneurs, and it's just a stream of carnage from doing so. And it's unfortunate. Large company cultures, middle market company culture, they're hard to change.

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They are. 100% are. And I've been the disruptor. That's usually how I've gotten hired. And even leadership doesn't want to. They think they want something. You go and you're like, we don't need to do this. This. Your sales guy from 20 years is a relic. Your model is wrong for this kind of. You're out. We're not doing that.

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That's what you are when you go into. You're a target.

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Oh, yeah, no doubt about it. But there's probably a role for something out there with that. I just don't have any interest right now of doing it. I'm like you. I actually also realized, and I think a lot of people realize this, if you're in a w two job, start your side hustle, because that is something that no one can take away. You can lose your job in a second for any reason, quite honestly, especially in the US. But if you have your own sources of income and you control what your market is, and you control kind of what your offering is, no one's taking that away. Assuming it's not legal. But as long as you have a legal business, you control your money potentially way more and way better than anything you'd ever work for. That would be secure.

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Thomas, you're speaking the truth on that. We actually actively encourage individuals in the company to have a side hustle.

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Yeah, well, we do, too.

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You got to have it. For some of them, it's just like, oh, I'm a musician. I'm going to have a band, and we're going to get paid. Do it. Just get it done. I want to write a book. Get. Write it. Whatever the case may be, you have to have that side hustle. And it's so important to being better on the job. You just have a different perspective.

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You're more energized. And I know from day one, in our company culture, I set up our company to everyone's on a four day.

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Work week.

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You got to get your stuff done for the customer. And that means if you have to kind of pick up hours, pick them up where you need to to go do it. But I want you to have a full day relative to market to go do whatever you want, as long as it's not competitive, as long as you're not doing anything, like, kind of unethical of selling our customer list or starting an actual competition to us, but do a side hustle that's non competitive and go do it. Or I want you to go scuba diving or go run or whatever you want to do there. But that was a conscious decision of not only that, but also entrepreneurs listening here. If you can make it as much outcome based in less about nine to five as possible, there's hours you might need to be attentive because of how their customers are and they need you. But for ours, I don't track hours. We just say, hey, you got to do this much work and this is what this role is worth. And if you could do it in 2 hours, you get paid the same. If you could do it, it takes you 40. It's the same value back to our customers and us. And so that's how we set things up. And I think what I was describing, they're just long winded, is if you really want to keep your teams happy and you want to be able to be self reflective, find the things that you like and you'd wanted working so you don't recreate another mid market, horrible culture. Start from day one with it.

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I love that outlook, man. That's good. I like how you started that. Four day week work, week two. That's aspirational for us. We've been thinking about, we haven't gotten there yet, but maybe now we have the motivation.

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This is how you do it. You just do it. Because this is what I know.

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Right on.

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If anybody died, you'd cover their work somehow. But not dying, they're just going to be gone one day a week. And so I let the team sort that out. I got Fridays, I want Wednesdays. There can't be an absence of people on a one day. Everyone's taking pride. It's like, no, but the point being is you get it sorted. You just do it and then people figure it out. It's not even hard. You just do it and that's it. Here, wait, hold on. Drop the mic. There it was. I dropped the mic. I don't know if you guys could hear that. I'll probably get edited out. Michael, I'm saying goodbye to you now because we're at that point where I have to say thank you for coming on. You've been great.

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It's been a pleasure, brother. Absolute pleasure.

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No, this has been very. And the insight in this perspective, and I'm looking forward to actually catching up with you after off camera here. Talk about. I had no idea. That's kind of what you guys did. From a podcast perspective, I didn't even know that market really existed. I thought just everyone kind of threw it out there on Spotify. Spray and pray, baby. So we're going to follow up later, and if you want to hear that interview, you can't because it'll be offline and you'll have to buy it from me. No, you won't. Just come ask, and I'll talk about what we did. Thank you so much. And listen, if you've made it to this part in the podcast, you get ten dad points. If you don't know what those are, it's okay. Just remember you have them. And if this was your first time, I do really hope you come back. And if you've got your own story, just reach out and let's see if we can get you on the show to tell it. If you've been here before, you rock, you get extra ten dead points. And like I said, if you can figure out where to spend them, you're doing great. But thank you so much for listening to the Never Been Promoted podcast. And until we meet again, go out there and unleash your entrepreneur.

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Thanks for listening to Never Been Promoted with Thomas Helfrich. Make sure to check the show notes for our guest contact information and any relevant links. Connect with Thomas personally at

Introduction to Entrepreneurial Journeys
Michael DeAloia's Unique Background
Evergreen Podcasts: Origin and Growth
Entrepreneurial Insights and Pivoting Strategies
Funding Strategies and Navigating Business Growth
Personal and Professional Development
Challenges, Solutions, and Internal Communication
Advice for Entrepreneurs: Networks and Support
Looking Ahead: Goals and Strategic Planning