DCP Entertainment’s Chris Colbert on How Podcasting Can Move Past Lip Service

Jeff Umbro: This is Podcast Perspectives, a show about the latest news in the podcast industry and the people behind it. Each week, we will bring you discussions about the latest news in the audio world and conversations with leaders in the industry. I'm your host, Jeff Umbro, founder and CEO of the Podglomerate, where we help produce, distribute, and monetize some of the largest podcasts in the world.

Joining me today on the show is Chris Colbert, founder and CEO of DCP Entertainment. Before founding an agency, Chris worked at SiriusXM in various roles within their podcast unit. After a very long stint at SiriusXM, Chris took his talents to Cadence13, the now Audacy-owned company in order to help them develop their audio documentaries.

In 2017, Chris went on to found DCP Entertainment. DCP defines itself as a media platform for underrepresented voices, including people of color, women, the LGBTQ+ community, and other overlooked communities. Fast forward to today and DCP works with some of the biggest brands in the world, including State Farm, Dell, Acast, and creates some of the largest shows in the industry, including the Toure Show, Democracy-ish, and the award winning series Say Their Name.

Chris also hosts a podcast called Entrepreneur Struggle, which he creates in partnership with LinkedIn. I was recently a guest on Entrepreneur Struggle. I highly recommend that you all check it out.

Today, we will chat with Chris about why he left his senior position at SiriusXM, the very concrete ways in which DCP elevates underrepresented voices in the podcast industry, and the ways that DCP is innovating in the podcast space. Thank you for joining us on the show and let's get to the interview.

Welcome to the show, Chris. Thank you so much for joining us.

Chris Colbert: Oh, thank you for having me. I'm really excited to, uh, to join you all.

Jeff Umbro: So I hate this question, but I ask everybody all the time anyway: how did you get to where you are today, cliff notes or as in depth as you want. What is your career trajectory to put you from point A to point B?

Chris Colbert: Yeah, I'll do my best to make it as quick as possible because I feel like there's so many tidbits that I want to say. I started my career - well, my professional paid career - at SiriusXM Radio, at the time it was Sirius before the merger happened, back in like 2006 as an intern. [I worked] my way all the way up, started getting paid in 2007 as a production coordinator, and worked my way all the way up to Director of Urban Talk and Comedy, which is a politically correct way of saying I ran Black and Latino talk and comedy programming.

And so a lot of the content I was doing was for those kinds of communities. But the people that I wanted to employ and give opportunities to were also from those backgrounds. And I thought that was a very important thing to do.

But a lot of what I was seeing there and at other companies is that even if you do give people those kinds of shows, they don't get the same level of talent booking, and marketing, and press as, say, a white, cis, heterosexual male hosted program.

And so, that journey within that company, but also just looking at the greater media landscape, made me realize that I want to give more of an opportunity for people of color, women, LGBTQ+, and that was the basis for creating DCP Entertainment. And to be completely honest, it was going to be a video documentary company at first. I wanted to do, like, this documentary on homelessness.

Before I could really jump all the way into that I got hired away from Sirius to a company called Cadence13, which is now part of Audacy, stayed with them for a year. That really got me my foray into podcasting and realized that this medium [had] a lot of the creativity and freedom that I remember from the early days of Sirius.

[It was also] podcasting being this industry that is still fairly young compared to all the other media formats. And so, if I want to create this equity, this is a great space to do it – before we get to a point of #OscarsSoWhite. And so that's when I made that pivot for DCP to say, alright, we're a media company, but we're going to be very podcast forward as we start things.

Jeff Umbro: Yeah, I have a thousand questions based on that thread alone, but to start, your mission at DCP is to lift underrepresented voices. How are you actually putting that into practice? What are some of the things that you do everyday that other networks or institutions in the podcast space can also do?

Chris Colbert: Yeah, I think, first and foremost, it's giving those opportunities to the host, but also the people behind the scenes. Having your content team reflect the audiences that you're speaking to, which sometimes means you have to hire freelancers, and it's not just all in-house staff.

Because maybe you think of a project or maybe you partner with somebody and they're trying to cater to a certain demographic and you might not have that kind of person on your team. I think it's really important to have those perspectives, those cultural touchpoints, to be able to speak responsibly to those kinds of audiences. And so that means sometimes bringing on some really talented freelancers and, who knows, they may end up being your next best full time employee too.

But also when it comes to the people that you see on the camera, behind the microphone, with that, we really try to be intentional about not pigeonholing people in the conversation. So representation, I think, is big. Having an incredible talent like Danielle Moody, who happens to be Black and a woman and a lesbian, speaking about politics and it's not just, "Hey, I'm just a Black woman talking about lesbian things." No, she's just a great political commentator and happens to come from those identities. And that then colors her perspective on the world, colors her commentary.

And I think like, that's really important for audiences to be able to see, and to be able to hear. And so I think that's where we try to take that responsible approach to catering to these kinds of communities. And that's Democracy-ish if anybody's interested in listening.

Jeff Umbro: On that note, do you find, because I see this at Podglomerate sometimes where we make a bunch of literary shows and then we get approached by a bunch of literary podcasters, for example. Do you find that you are being approached by people who want to work within DCP or is it more of an outbound facing situation where you're actively going out and seeking that kind of talent to work with?

Chris Colbert: I think it's evolved over the years. I really went all in with the company back in 2018 and so over these last five years, the first three, I'd say, we were really going out and searching for people. Now I think we've made enough of a name for ourselves. We have some incredible projects, and great partners. And so word has gotten around about people who want to work for the company, but also people who want to partner with us.

So now we do have more people who reach out to us and say, "I love what you're doing. I'd like to be a part of that." Or, "Hey, we have this new project coming up and we really want to speak to these communities, or we want to touch on social justice issues, but we don't know how to do it responsibly".

We do a project called Say Their Name, one that I host, write, and executive produce along with my Chief Operating Officer, Adell Coleman, where we go around the country interviewing families impacted by police violence. And so we have to work in trauma and deal in social justice and do so in a responsible way. And so sometimes we get hired or get inquiries based around those things.

But yeah, I think a lot of people come to us just based on some of the work that we've done, the people that we've worked with, and that opens up those opportunities for us to work with others.

Jeff Umbro: And how do you measure success? Are you quantifying this at all?

Chris Colbert: Yeah. And I think there's multiple levels of success.

Obviously there's the financial side. We are a for-profit company. So I think we've done a good job diversifying our income recently to really take hold of that. While, say, like, the ad marketplace might be down, we lean in more to the work-for-hire stuff, which we had some great opportunities with, but also looking at, like, social media and all these other ways to monetize. So we have seen success there.

But I also think we've seen success from impact. Again, I'll reference back to Say Their Name: the impact of hearing these families tell us, "Wow, this is the first time I've truly been able to tell my story in a full and complete way." And even them saying, “Some of the family members that you interviewed, these are stories I've never even heard." That is impact.

Also taking it beyond that: this past season that we did, that was more focused on women impacted by police violence, our work was actually taken to the United Nations –

Jeff Umbro: Oh, wow.

Chris Colbert: – As part of a study that's hopefully gonna help to bring some kind of accountability and some kind of actions around police violence, particularly around women. So that is a really impactful piece that I never saw coming. Krista Noelle, who is one of the people featured in our series, is the one who spearheaded that. She's gone to Geneva and compiled our work to put into her study that she took to them.

So impact is a really big piece of what we do. We are mission driven as well and so I think that is also success.

Jeff Umbro: I want to come back to that aspect a little bit, in terms of how you operate as a business in that regard, looking out for the equity [among] the stakeholders on every side, including at DCP.

But before we dive into that, what are the services that DCP offers? What do you do every day?

Chris Colbert: Sure. So we're essentially like a one stop shop for media, but especially in the podcasting space.

So we are now a media agency, but I think we're most known as a production company where we can come in and consult when it comes to ideating on a new show, how are you going to reach certain audiences, setting goals, things like that. But also on the pre-production side of bringing in staff for research, putting together trailers, things like that.

We can record - we actually have a space here in Times Square, which I'm currently in, where we can record content in New York. But we have relationships with studios around the country. So we have ways to record your content, even if it's remote like this, using something like a Riverside, things like that.

And then we also do the post-production, editing, and then into distribution, marketing and sales.

So part of the thing that we've always done has been very forward-facing when it came to video. So I think that's something that helps us stand out in the marketplace as well. Especially as we see the trend these last couple of years of more video podcasts. We do high quality audio/video content, clips that can go out for social media. So we can help with graphics and stuff like that for social, but we can also create long form video content for say Spotify, or again, YouTube.

But what we've done more recently, as well, as we've pivoted it into being a media agency, is also be a place where you can come if you're just looking for marketing and sales. We have a new show that I can't announce just yet. Our new partnership, we're just going to do sales and marketing for them. They are doing all the production. We still want to make sure that it's high quality and they've already done a previous season. So we know the quality is there. But then we come in for the sales and marketing to help them strategize on the ways to get this to the audiences that they're trying to reach and use our existing or new sales relationships to be able to bring in monetization, hopefully day one.

Jeff Umbro: Are you marketing like, products and brands, other podcasts, whoever comes to you?

Chris Colbert: Whoever comes to us. We still want to operate underneath that underrepresented communities umbrella. So, some of the inquiries and conversations we've had so far [are] definitely more in like the nonprofit space or leading up to some kind of campaign that a company is doing for those kinds of communities. So that's definitely our sweet spot.

But anybody who wants to come to us for those kinds of services, we love to have those conversations.

Jeff Umbro: You were the Director of Urban Talk and Comedy at Sirius XM, and you've already covered this a little bit, but I'm always curious when people have big jobs at big institutions, and then move on to create their own thing... It's interesting, like you in theory had a position of power where you could actually kind of hand out shows to people and help them create podcasts and platforms in order to reach an audience that, in theory, has a lot of the institutional reach from SiriusXM.

And instead you went off, you created your own thing. It's turned into something great, but I'm sure initially it was probably a lot smaller. And you mentioned before that you did that because no matter what the intentions are, some of these bigger institutions aren't really putting the resources behind these shows that they might another.

Would you still agree with that statement today? Now that a lot of these organizations have put, in theory, a lot of resources into underrepresented voices on some of these networks.

Chris Colbert: Yeah, I still think it is an issue.

I think you can just look at some of the recent layoffs that have happened in the industry, whether it be TV, radio, or podcasting, but we'll stick to podcasting... When you look at some of the award-winning shows that have been laid off, they tend to be ones that are creators of color. But it's just so interesting to see that when there's cuts that happen, we tend to be the first ones cut. When you look at the internal staff that have been cut, a lot of times it tended to be those producers and editors of color.

Back to even when I was at Sirius and figuring out this new trajectory for my career, [I] was seeing that it was a self-fulfilling prophecy at these companies, where you say that these audiences don't exist for your programming and then you don't either create it or you don't market what you already have. And then you come back to your meeting [and they say]: "See I told you that these audiences weren't here for podcasting or for satellite radio." But it's like, "No, you didn't actually give them an opportunity to succeed." And so that's why you're getting these kinds of outcomes that you actually created yourself.

So, yeah, I think we still have an issue with it. I think the podcasting landscape has gotten a lot better. I think the media landscape has gotten better, but I also think that a lot of this has been - and I'm not going to use the right term - but almost like lip service, based off of what happened in 2020, 2021 with George Floyd. All these companies want to say, “We're doing all this for Black people. We're doing these things for the LGBTQ community." And so we do these things for press releases, but there's tons of articles out there that show that the investment that a lot of these companies said that they were going to do has not been fulfilled. And no one's fully checking them on that.

And so I think there's still a lot of work that needs to be done. And that's where I want my company to help fill gaps, but at the same time to be an example for major companies to see, "Oh, DCP is having success with these audiences. We can take a chance on those audiences too."

Jeff Umbro: Lip service is a good way to put it - you have a lot of people who are making a lot of promises that they don't necessarily fulfill. So I'm glad that DCP and you exist. I'm sorry that that's a necessary piece.

But DCP is a company that kind of lives, in some ways, in a similar layer of the ecosystem to Podglomerate. You guys are a mid-sized company that, in a lot of ways, punches above your weight class. You're making these very cool shows for these very cool creators and these very cool companies.

Now, as we know, and our listeners are probably aware, in the last year or two, there's been a lot of talk around what is being referenced as a "rollup." The idea [is that] a bunch of these smaller, mid-sized companies [are] combining forces in order to make a greater entity that may be more attractive for business operations today or for future sales.

It's interesting to see what's happening in the industry and I always like to ask people who are operating in that sphere how they view it. So how do you view that? Do you think that this is ultimately going to help the industry as a whole to get some of these mid-tier players a little bit more power, or is this something that's ultimately going to set us back a little bit?

Chris Colbert: I think it's positive. I think anytime that you can combine your efforts to try to bring in monetization to keep things sustainable for your companies, I think it's really important.

One of the things I love the most about the podcast industry is the collaboration. You know, radio, TV, even print, [there's] very much an adversarial kind of relationship with other companies where it's us versus you. Here it's an on demand platform, so I think everybody understands that this is still a young industry where there's still a lot of audiences that haven't been exposed to podcasting, so we can create this larger pie for everybody to eat from.

So I think ultimately it's a positive thing when you combine those resources, combine those shows together. So go to an advertiser and say, "Alright, my show doesn't get a million downloads, but when you combine all of our shows together, maybe we get there." And hopefully it's a targeted audience where now you can charge maybe a premium rate to be able to hit that.

That premium rate is also something where as a company, we've been trying to help to shift the norms in podcasting. We're not the only ones doing it - trying to get away from the CPM model. I think it very much devalues these audiences that we have, especially these niche audiences. And I don't say niche in terms of like, ethnicity niche...

Jeff Umbro: No of course. It's like, specification.

Chris Colbert: Exactly. And so I think there's really valuable audiences, and as we continue to improve the data that we can get, and to learn about our audiences - whether that be through surveys or what these podcast hosting sites give us - that's going to, I think, truly give us the ability to go to advertisers and say, “You're targeting this exact audience and that's why you need to pay this premium price.”

Not this CPM model, which, the CPM model is better than, say, YouTube and some other mediums, but I still think there's so much more value to our audiences. Especially when you look at how much influencers on social media get paid. They get paid, you know, $10,000 per post, some of them. And yet, as podcasters, we're trying to scrape together $25 for a thousand people to listen to a podcast.

So yeah, combining those resources is great, but I still think there's a larger thing that we need to tackle here in the industry, which is valuing those niche audiences.

Jeff Umbro: Okay... so much to dive into there.

Chris Colbert: Sorry, I go on on so many tangents!

Jeff Umbro: No, I love it. Is it working? Are you able to find advertisers who are willing to pay, like, a flat rate as opposed to a CPM?

Chris Colbert: It's a newer thing we've been doing, but we are seeing some success there. And part of it is because our company, DCP, is audio, it's video... We've actually pivoted our business model to being also social media, content creation, and just marketing services as a whole.

And so what we're doing is essentially 360 sales. So yes, you can buy just the podcast app, but what we're really trying to encourage is that to really get saturation for your brand, you need to be hitting your audiences in many different places at the same time. So we're going to sell you on the podcast for your mid roll or pre roll position. We're going to sell you in the clips that we put on social media. If it makes sense, we're going to do product placement or a logo on our video content that goes on YouTube. We can also then tie in brand ambassadorship with our host, so they're going to put out X amount of posts that are specific about your brand to say, "I love this thing," or, "Hey, I'm rocking these headphones."

So I think we've seen some success there, again, especially as we look at companies who might be afraid to put in money in podcasting, but they already have a big budget in social media. We can now combine those budgets that they can say, all right, we only have $10,000 to spend from our podcast budget, but we have $100,000 to spend from our social media budget. So let's pull those together and be able to advertise on say Toure's show and also then have some of those viral clips that go out of there also have branding for that brand.

Jeff Umbro: I love that. That is so smart. It's kind of like an evolution on product placement. And people are always talking about like, 360 degree packages where you can hit all of these different touch points, but it is so hard to execute... not only selling it, but then actually like, doing it and doing it well, it's tough. So kudos to you.

Given that, when you're looking at bringing on a new show to the network, or creating a new show, are you looking for somebody who has an existing audience on all of these platforms, or are you looking to build those audiences for the right voices?

Chris Colbert: I think it depends on the season that we're in as a company. So right now, yes, we are looking for people who already have an existing audience, whether it be through their current podcast, or whether it be because they're a social media influencer or somebody on TV or something like that.

But in the past we have taken people who were [we just say], "Hey, this is an incredible idea. There's nobody else doing this in the landscape. We want to champion this show."

But I think there has to be a balance between the two. We want these shows that already have an audience or these people who already have an audience. That way we now, as a network, have a place to cross promote our new show with, say, maybe something you'd never heard of.

So I think right now, we have a decent amount of those kinds of programs where, you know, I host two podcasts on our network, but most people don't know who I am. I'm not some big influencer. And so...

Jeff Umbro: You are in the podcast space.

Chris Colbert: Oh, thank you. And so we have people like Shantae Howe, Lacey Henderson, in the past, where they actually have done incredible things, but you just might not know their name. And so we need to balance that with a Toure or a Danielle Moody. We can cross promote there.

So yeah, it's a balance. But at this current moment, we're definitely looking for those existing audiences, so we can leverage right out of the gate with sales and marketing. And things like that.

Jeff Umbro:  It's so funny, because I mean, there's so few examples of like, a Normal Gossip, where a show seemingly comes out of nowhere and is able to just get this massive audience and become part of the zeitgeist. So I know a lot of networks are trying to start with somebody who already has an existing platform, but it's a lot easier said than done.

And also like I was talking about, [there's] the cross promotion opportunity, but hopefully those shows, those people who already have a following, they can also make money that then allows you to spend to be able to have more marketing for those say lower tier shows.

One of my favorite conversations is asking networks what their relationship is to the creators on the network. I know that that can get really sticky in a million different ways as to who owns what, and the RSS feed, and the IP, and the brand, and the audio, and everybody has a different answer to that question.

So how do you think about that? I'm sure it's different for each of the different creators that you work with, but is this a situation where you like to own the content on the network? Is it a partnership with your creators? How do you think about it?

Chris Colbert: So we always try to leave [ownership] with the person who created the show. We only own IP if it's our own original idea, like a Say Their Name or an Entrepreneur Struggle. But we have shows like Toure's show where Toure already had an existing podcast and came to us. And so we're not going to take that IP. So we're essentially licensing that content to help him to hopefully get more audience and hopefully make more money. There's also things where we get hired by other companies to work on their projects. And so, again, we never try to dip into that IP space.

To take that question a little step further, with our relationship with our hosts, our partners, we have a really great relationship, especially with our initial hosts, where we work hand in hand with them to grow the network. They're very much invested in what we do as a company, and they're constantly bringing us new talent, they're bringing us ideas. Danielle's coming behind the scenes to work on stuff. Toure is constantly throwing ideas out to me of new podcasts that we can do, whether it be ones he's hosting or somebody else. So it's really great to have hosts that are invested in our overall company success.

And I didn't think about this when I was there, but at Sirius, one of the things I think was a missed opportunity, [is] they just treat the host as a host, and forget that these are people who have great strategies, great ideas. And so it's just like, "oh yeah, just come in and speak on the microphone." No, you can have these strategy sessions that can help grow the overall brand.

And so why not tap into that? And that's what we've definitely done with the hosts and partners that we've worked with.

Jeff Umbro: It's kind of the Holy Grail, is to have buy-in from everybody within the network. And that just shows that you're running a great ship because if you weren't, people would not be helping you out there.

Chris Colbert: Especially early on too, some of these people weren't even making money, and they were sticking with us. Every day I was like, dreading them leaving, but they're like, "No, I'm invested. We're going to make this work." So we owe a lot to the hosts that have been with us, especially for the last three, four or five years.

Jeff Umbro: Yeah. I have a very similar experience with Podglomerate and my gratitude is endless for the folks that were early, and still to this day, everybody who works with us. But it's something special about the OGs.

Chris Colbert: Oh yeah.

Jeff Umbro: But I wanted to ask you about your video strategy, and you touched on this a little bit, but I've actually been on your YouTube all week, just taking notes on how you're actually executing on everything, because it's really smart. And I don't actually know if it's any different than what a typical YouTube studio would be doing, it's just so new to podcasting.

But how do you think about video in what you're doing?

Chris Colbert: So we have a subcompany underneath DCP called Podstream Studios based here in Times Square. Part of what we think about with that is we're spending all this money trying to rent other spaces. It just became more cost effective to do our own thing.

But also all these studios you'd rent - it was a kind of cookie cutter kind of situation. So you could look at a video and know exactly where they recorded. Here you can choose different backdrops, different tables, different knickknacks, bookshelves, all those kinds of things. So for us it allows us to create our own content, but also we can rent out to other podcasters to do the same thing. And I think that helps the greater ecosystem as well, when it comes to video.

Because for us, when we think about video, especially early on, it was a great lead generator. So we started out not putting out full episodes. We put out these short clips that were for Instagram, TikTok... And we found that, especially on TikTok, it was helping bring people back to the podcast. So we'd have something in our link in bio, or if it's on Twitter actually have the link there in the caption, to send people to the pod link.

So now they can choose Spotify or Apple. We try not to point to one specific platform because Apple is very much used here in the U.S., but outside this country it's not. And also there's tons of Android users who don't use it. So we always try to promote as many platforms as possible when it comes to our video content.

But back to the strategy itself: [we use] these one-minute or less video clips that hopefully entice you to want to hear more of the conversation. That said, more recently, we're now dipping into the full video episodes, especially for someone like Toure, where we've seen his clips go viral, especially using YouTube Shorts, and again on TikTok, where we get millions of downloads on some of these things, or millions of impressions. Now that we see that there's a video audience for this show, let's instead of trying to convert a video audience over to the audio space, let's also give them a place to go directly for more video content.

So I think we're starting to see some success there and I'm still kind of seeing how YouTube and Spotify really play into the greater podcasting ecosystem, but it's worth a try. And we're going to start there and see if that has success, then we can branch out in other spaces.

But I think when it comes to full video episodes, it really has to be something that makes sense for it. Toure interviews lots of successful, especially musicians, so that works really well on YouTube with their algorithm, because a lot of people are listening to music on YouTube. So when you search, say, a Kendrick Lamar, you can then see his episode with Kendrick Lamar pop up as well after you listen to a song. So I think that's why we're intentional with that show particularly, but, say, a show like Democracy-ish, I don't know if it necessarily leans in the same way.

So we'll see as it goes along, but I think everything is just: you test and you look at analytics and then you see if you want to continue doing that.

Jeff Umbro: It's so interesting, we're kind of in the process of trying to figure that out ourselves, and YouTube is an entirely different beast. Like you have to really think about everything from the metadata, to the thumbnail, to how did you actually record, are you just putting an audiogram up... Even this interview that people will be listening to one day, it's the two of us on Riverside, which ultimately looks like a fancy Zoom - they could go and listen to this on Spotify without video, or on Apple podcasts, or wherever, but for whatever reason, some people prefer YouTube. I'm of the school where you should be where everyone is and be available wherever they might want to be.

But you said something earlier about how initially you were looking to convert your video viewers to podcast listeners, and you were doing that through links in bio, and TikTok, and Instagram reels, but how are you tracking that? How intentional were you? Was this a byproduct of you coming up with social content?

Chris Colbert: Yeah, it was intentional. And yeah, it was definitely in conjunction with that. We had hired a social media manager [who] was helping with that.

At the time, we were also working with Nadya Okamoto, who is a very big influencer herself. At the time, I think she had like three or four million followers on TikTok. And so she was a great test study. She's from the Gen Z generation, which again, I think is more into the video side of the podcasting space. And we saw like, huge conversions with her bringing people over from TikTok. Also, depending on the subject matter: when you talk about sex, or family, or things that are really personal, you really get those conversions.

And we also found that certain conversations made sense on different platforms. Our political conversations did best on Twitter. Our more celebrity-driven content did better on Instagram. Our more personal stuff did better on TikTok. Not just for the views there, but also [converting] back to the audio space. I think all those things were helpful.

And just back to one quick thing on YouTube, a resource for people: you were mentioning metadata, that's so super important. I didn't know how to do all those things. So we invested in vidIQ, which has been really helpful in terms of helping us suggest keywords and making sure that you have all the metadata that you need. It gives you a checklist of: you didn't put in your thumbnail, you didn't put in enough keywords... And then even when you do put in those things, it'll then show you: here's the other videos that would relate to your content so you can see, does that really align? And so it's a really inexpensive platform that really helped us level up our YouTube game.

Jeff Umbro: That's great. I'm going to check that out after this interview.

We just recorded an interview on your show Entrepreneur Struggle, which you host. I know that I was the final episode of season 2, so hopefully you'll be back soon. But how did that show come about? Because it's part of the LinkedIn Podcast Network, part of their accelerator program, right?

Chris Colbert: Exactly, the LinkedIn Podcast Academy.

So I started it as a social media thing back in 2019 going into 2020, where I was talking directly about my struggles and it would just be like, here's my struggles and here is how I overcame certain aspects [of them]. And so every week was a different topic I'd touch on.

And literally the last episode I recorded, I was at a WeWork, when we in New York, got the notice that, “Oh yeah, you need to go home. Like the pandemic is really bad. You need to go home.” I was literally in the middle of recording. I was getting that alert going off my phone, like get out of the building.

Jeff Umbro: Wow.

Chris Colbert: I was like, well, I'm going to finish this recording, but then I stopped.

At the time I realized, if I'm going to move forward with this, I'd like to do this where I'm talking to others about their challenges. And I can still talk about the things that I've faced, but I really want to learn because what I found, going to bars and just talking to people - especially during the pandemic talking remotely to folks - a lot of us entrepreneurs have the same challenges, and a lot of us, I think, are afraid to talk about them openly. Because we don't want to scare away any potential business or even scare our own staff. Like, "Oh, they don't have it all together. So why am I working here? Is everything going to be okay?"

But a lot of us do have those challenges. And the more we talk about it, the more we feel less alone, the more we can learn from each other. And the more we just feel like, “Okay, everything's heading in the right direction.” And so I wanted to bring those bar conversations that I was having, these virtual conversations, to a more of a public sphere, and not just talking to people in my industry, but talking to people in every different industry.

Cause I also think as we learn about the challenges that people overcame and some of the things that they do to make their company unique, it allows us to apply them to our business. And I think that's where real creativity comes in these spaces. Like I can learn something from somebody in the financial sector, or somebody in the IT sector, that makes me think differently about how to approach my business or even approach my personal routines as I think about my companies.

So that was the basis for creating it. [In] 2022, I did about 20 episodes. I was doing one every couple of weeks. And then at the end of that year, I was like, “Man, I have so many things happening with my companies. I don't have time to focus on this anymore.” 

I ended season one. I thought at the end of that season, I may or may not bring it back. We'll see what happens and lo and behold, I think it was two months later, I get an email from LinkedIn saying, "Hey, we're starting this accelerator program. We'd love for Entrepreneur Struggle to be a part of it."

That was the journey of Entrepreneurial Struggle. Now, as you said, we just ended season two, because again, I'm now in a season where things are really picking up with Podstream and with DCP. So, we'll see what happens from here. It might go back to a journaling kind of thing for me. It might go back to interviewing folks. But for now, we're just going to take a little break and just see where things take us.

Jeff Umbro: Yeah, honestly, I discovered the show a few months back and I've been loving it. As an entrepreneur, I've really taken a lot of the lessons to heart.

I was actually on the show a few weeks ago. Everybody should check it out. And it was great. It was like a therapy session with Chris. I listened back and I was embarrassed by half the stuff that I said... but exactly to your point, there's probably so many other people who are going through the exact same things that I did, and this is going to be something that's so valuable to them, so I'm really happy that I did it.

Chris Colbert: And I'm glad you said the therapy session thing too, because - I don't think I've really said this many places - when I was a kid, I wanted to be a psychologist. And then when I went to school my minor was sociology. So I'm just interested in people, what makes people who they are and all that. And so this is almost like my outlet for being the psychologist I wanted to be as a kid. So I'm glad that you felt it that way.

Jeff Umbro: Oh a hundred percent. And you asked all the right questions and for me, it was like, I wanted to be an astronaut, and now I just watch Star Wars all the time.

But this is the reason that I got into this industry is so that I could talk to people and learn things and make something that is hopefully valuable for some people out there. And so here we are. I think it's important to keep doing that. You host two shows now. You have two companies, you're doing such cool stuff, and I know that this conversation between you and I will continue for years to come, and thank you so much for joining us on the show today.

Chris Colbert: You're welcome.

Jeff Umbro: Have questions, tips, or podcast recommendations? You can follow me on all of the socials @JeffUmbro. Podcast Perspectives is a production of the Podglomerate. If you're looking for help producing, distributing, or monetizing your podcast, you can find us at podglomerate.com. Shoot us an email at listen@thepodglomerate.com or follow us on all social platforms @podglomerate.

Thank you to Chris Boniello, Henry Lavoie, and Jordan Aaron for producing this show and also to our marketing team, Joni Deusch, Madison Richards, Morgan Swift, Matt Keeley, Annabella Pena, and a special thank you to Dan Christo. Thank you all for listening, and I will catch you next week.