Inside O’Rourke Media Group’s community-first approach with Jim O’Rourke (LNM Episode 46)

Jim O'Rourke, CEO and founder of O'Rourke Media Group, shares his journey in local media, from delivering newspapers as a kid to founding a rapidly growing digital-first publishing chain. O'Rourke discusses his approach to acquiring and revitalizing local newspapers, investing in local talent and growing the digital business. He outlines the strategic choices that have guided O'Rourke Media’s success, including his firm stance against paywalls and his commitment to community-focused journalism and sales.

In the face of industry pressures, O'Rourke explains why he values small and midsize markets and how he's developed O'Rourke Media Group’s sustainable model by prioritizing advertiser relationships, high-quality local reporting, and new digital revenue streams. He discusses his philosophy on embracing sponsored content as a core revenue source while carefully navigating editorial integrity—a delicate balance that he believes is essential for the future of local news.

O'Rourke also explores his renewed investment in print, noting the value print editions hold for both advertisers and local audiences. Reflecting on key lessons learned, he details his experiences working under Berkshire Hathaway, why he finds potential in digital agency services, and his vision for the future, including expanding into more communities and a possible employee ownership model.

Episode chapters:
(00:02:59) – Overview of O’Rourke Media Group
(00:04:51) – Jim’s journey from paper delivery to media leadership
(00:10:32) – Founding O'Rourke Media Group after private equity fell through
(00:17:59) – Why local news is still a great investment
(00:21:46) – Balancing sales and editorial resources, local and centralized support
(00:29:49) – The importance of maintaining brand trust and relationships
(00:37:21) – Expanding digital while avoiding paywalls
(00:42:22) – Sponsored content and adapting digital revenue streams
(00:49:12) – Relaunching print in Milton, Vermont
(00:52:59) – The challenges of printing presses
(01:00:30) – Lessons from working at Berkshire Hathaway’s World Book
(01:03:18) – Rapid-fire questions
(01:22:14) – Media and local recommendations

Listen to the episode here:

Bio:

Jim O'Rourke is the CEO and Founder of one the fastest growing local media companies in the U.S. Jim and his team are focused on building a digital media enterprise that continues to publish excellent print newspapers and niche publications. They are entrepreneurial, adaptive and have an aggressive, short-term goal to expand the company to 100 markets over the next several years.

Jim and OMG bring a contrarian business mindset to the media industry, maintain a low-cost corporate infrastructure and decentralized approach to running our business.

Jim grew up and spent the first 25 years of his life in Philadelphia before setting out on a career path that included jobs with several of the country's largest media companies–Gannett, formerly GateHouse, Digital First Media (now Media News Group) and World Book, Inc, a subsidiary of Berkshire Hathaway. Jim maintains a commitment to fitness and nutrition, is devoted to his amazing wife and children, expects to win in business and has always viewed work as a “passion not a job.”

Full transcript:

(recorded via Riverside.fm; transcript automated via Castmagic.io, mostly unedited)

JIM O'ROURKE [00:00:00]:Investors never really get it. I guess some of them do. I haven't come across many. What I see is, like, these established brands and trusted brands, established brands, tons of advertising relationships. I mean, in our small little and I we're I still think we're tiny, but, you know, we do business with 15,000 advertisers a year. And to me, like, that's impressive. I mean, that—and I've over the years, I've, in my own company as well as for other companies, I've tinkered with establishing new brands and saying, oh, yeah. You know, this will work. Brand new. Why? No debt. And we start from scratch, and we just—that's hard. That's a hard path to go down. So I just have such, I have a lot of admiration for these brands. I think our business in Vermont is the oldest operating business in Vermont. If we do the right things with our audience and with the news that we provide, we're going to be around for a long time. Like, we're not going anywhere. Right? So that's the attraction that I have with it.

TIM REGAN-PORTER [00:01:12]: Welcome to the Local News Matters podcast, where we explore pathways to stronger journalism, better businesses, and healthier communities. I'm Tim Regan-Porter, CEO of the Colorado Press Association.

This episode, I talk with Jim O’Rourke, CEO and founder of O’Rourke Media Group. We discuss his company’s rapid growth and unconventional approach to building a digital-first media enterprise that still values print publications. Jim shares his experience growing O’Rourke Media and talks about the key challenges he’s faced, including adapting to changes in local news, evolving digital strategies, and balancing local autonomy with centralized operations.

Jim’s journey began when he was just nine years old, delivering newspapers in Philadelphia, and has taken him through leadership roles at major media companies including Gannett and Digital First Media. Now, he’s focused on reinvigorating local news by leaning into entrepreneurial tactics, all while maintaining a contrarian mindset toward industry trends like paywalls and philanthropic funding.

In this episode, Jim shares valuable insights for those interested in the financial sustainability of local journalism—from his take on the future of print and digital media to the opportunities in sponsored content to lessons learned from his time with Warren Buffett’s Berkshire Hathaway-owned World Book.

If you like this episode and what we're doing more generally, please follow in your favorite podcast app, leave us a five-star review on Apple Podcasts, and tell your friends about us. This is a side project and a labor of love, and your support means a lot. You can find past episodes, full transcripts, and relevant links, and sign up for our newsletter at localnewsmatterspodcast.com, or for lazy typists like me at lnmpod.com. You also follow us on most social media channels @lnmpod.

And now I bring you Jim O’Rourke.

TIM REGAN-PORTER [00:02:56]: Well, welcome, Jim, to the podcast.

JIM O'ROURKE [00:02:58]: Thanks, Tim. Great to be here.

Overview of O’Rourke Media Group

TIM REGAN-PORTER [00:02:59]: So you run and started O'Rourke Media Group. How many papers, and in how many states are you at right now? Because I know you just sold one in Virginia.

JIM O'ROURKE [00:03:09]: Yep. Currently, we're in eight different states, 37 markets, and a total of 51 publications.

TIM REGAN-PORTER [00:03:17]: And what types of markets are these? Size city, that sort of thing?

JIM O'ROURKE [00:03:22]: Most of them are hyperlocal community markets where, you know, we're the main source of news and information in the towns, but we have, you know, diversified a little bit. We have a really cool monthly newspaper out here where I'm working in Arizona, You know, bigger metro area, but we have a niche monthly. We have a few niche publications out there in, say, Delaware and a few other states. So we've wandered off the map a little bit in terms of hyperlocal news, but generally, everything we have going on is in the content, you know, space.

TIM REGAN-PORTER [00:03:58]: And mostly in small to medium sized markets? Are you in any major metros?

JIM O'ROURKE [00:04:02]: Yep. Small to medium sized markets, but most of them seem to flank a major suburb. So we have local newspapers in and around Minneapolis as an example. We have neat businesses out in Vermont that circle Burlington or in Chittenden County. So we're kind of in that rural market, and a lot of the markets that I go to and visit, you know, when I turn the TV on in the hotel, the, you know, the main news channels are covering some other town, and not that particular town where we have a newspaper.

TIM REGAN-PORTER [00:04:34]: And where are you based out of?

JIM O'ROURKE [00:04:35]: I'm based currently out of Arizona. So our corporate headquarters, quote, unquote, headquarters is, I'm in a bedroom now in my house. So that's, when I'm not traveling to one of our office locations. This is what I call corporate headquarters here.

Jim’s journey from paper delivery to media leadership

TIM REGAN-PORTER [00:04:51]: And so when you started O’Rourke Media Group in 2018, that's a very interesting story. It's how it started as sort of a private equity play. So before we get to that, which I really wanna dig into and all of the things you've learned since starting your work, give us a little bit of your background. I believe you started when you were a kid delivering newspapers.

JIM O'ROURKE [00:05:13]: That's right. I started delivering newspapers for the Philadelphia Inquirer when I was nine years old, under my brother's name or sister's name. I forget because we weren't old enough, of course. Then I just stuck with it. We delivered newspapers and just I loved it for some reason. It was fun. I had more money than most kids on my block and in my neighborhood, because I was out hustling doing papers in the morning. The Inquire being an AM publication during high school and college was perfect because it didn't interfere with anything else going on at school or extracurricular activities.

JIM O'ROURKE [00:05:49]: And then I got into managing carriers as a branch captain for a number of years and that's, of course, when I started driving and have my own car. So, and it just grew on me. When I got out of college, I didn't really go to college to pursue a career in newspapers. I was in circulation. I mean, I hustled newspapers. But when I got out of school, I ended up, you know, getting a job in Norristown, Pennsylvania. After trying a bunch of other things and whatever, I answered this job ad and, Journal-Register Company, the original one, had just bought this newspaper in Norristown. And, of course, you know, I didn't know anything that was going back then, but when I look back now, a lot of people got let go.

JIM O'ROURKE [00:06:38]: All the companies got sold. All the cars got sold off. The place was in this total disarray, and here I come in, you know, all happy to have a job as a DM making $385 a week. And that's—I haven't looked back from that point of it. I've been in it ever since. That was 1994. So that's kinda how I got started on this journey.

TIM REGAN-PORTER [00:07:02]: And then you worked your way up, became publisher. You know, what was, what sort of the major steps in your career before founding O’Rourke Media?

JIM O'ROURKE [00:07:11]: Yep. District manager, home delivery manager, circ director, and then, yeah, I was fortunate to get an opportunity to cut into the publisher ranks when I worked for GateHouse Media and that's where I got my first chance working for Kirk Davis. In the original company in New England before GateHouse, I went to work for Kirk as the VP of circulation, you know, a few metro size, few big size dailies, and a bunch of weeklies. And then, you know, within year one, the whole GateHouse thing just exploded and they bought us, they bought our competitor, and they were buying a bunch of other things at the time. So I was the benefactor of that, in that, you know, I was able to run a much bigger cert department. I was, you know, in charge of, I don't know, at the time, 156 newspapers in GateHouse New England and a massive revenue budget. And during that time, I was able to shift into becoming a publisher for one of the companies that we bought in Taunton, Massachusetts. And that's what I wanted all along.

JIM O'ROURKE [00:08:15]: I wanted to get to the publisher level, and I wanted to run my own show. And I wanted to quite honestly get my hands on sales. And on the circulation side of the house at that time, we were constantly cutting costs to offset declining revenues and advertising, and that used to piss me off. And, so as soon as I got that publisher opportunity, I was able to do with an ad sales team, you know, what I was critiquing all these years and then ever, I've been in it since then in just bigger publisher jobs, bigger president roles. And when I left GateHouse in 2012, I went to be the president and publisher for Digital First Media / Media News Group in Michigan and we had about 30 newspapers and that was a fantastic business, some major dailies and dozens of weeklies. I had a lot of fun in that job. There was a lot of change. It was when Digital First, The Journal-Register, was working through a bankruptcy.

JIM O'ROURKE [00:09:18]: So I, you know, I had to manage through all that. And being in that Detroit area, during a bankruptcy with union negotiations and lots of change, all great learning and, like always, just hunkered down, figured out how to build a great team, and we had a lot of success there in in Michigan and, you know, things change and I moved on from that role. And I went to run World Book Encyclopedias for Berkshire Hathaway and based out of Chicago. So I had a lot of fun with that. It was, to be honest with you, it was a much easier job than working in newspapers. It really wasn't an old encyclopedia company anymore. The business had totally pivoted already to digital and selling online, you know, licenses and products to schools and libraries across the country. But it was a great experience stepping outside of the newspaper business and just learning a whole different business and that, you know, I didn't know how to act at first because when you went home on Friday, the emails and calls and everything just stopped, and then it restarted Monday morning.

Founding O'Rourke Media Group after private equity fell through

JIM O'ROURKE [00:10:32]: So I was, like, looking at my phone all weekend and thinking, what's going on here? I'm not used to this. And, so it was just a slower pace. Not an easy business by any means, but it was good to step out and see something. It kind of validated how hard it is, that what we do in managing in the media business. So, from World Book, I got the itch. I—the itch always seems to be triggered by a headhunter calling and saying, hey. You know, we got this opportunity you might be interested in. And this particular one, I was getting a lot of those type calls at the time, but this one I listened to and took because it was a family owned or a private equity group that never sold a business, and the top guy wanted to build a media company as part of the portfolio.

JIM O'ROURKE [00:11:23]: The company's name was Eli Global, and I went to work for them. It was a long process and it was a competitive process. There was a couple other, you know, reputable folks in the industry that were going for this job, so they picked me and I went in and, you know, built a pipeline and started to, you know, prepare for the companies we were gonna buy, and it was good because, you know, it's always people always welcome a new buyer into the mix when it comes to newspapers and what's been going on in our industry. And but four months in, and that started to go sideways, for nothing that I was doing, but something that the company was involved with at the time. And so that ended up after four months, I ended up getting fired, and it was kind of shocking because I was doing everything they asked me to do, and I thought they were excited about it. I was actually at their corporate office buttoning down the financing for the first company we were gonna buy, and I got fired on the way home at the airport. So and so I was pretty distraught. I was down and out for about a day.

JIM O'ROURKE [00:12:33]: I had a handful of IPAs on the plane ride home. I was never out of work. I was never out of work, so, you know, it was kind of a new thing to navigate for me And then, you know, I just sat outside the next day and figured it out. I, at first, I had my whole plan. So when I went to work for Eli Global, I had to prepare, like, a whole business plan and strategy on how what we were gonna do. So I was kinda ready to go, and I figured, you know what? I'll just go find another private equity partner. And I'm in Chicago, so I did a bunch of cold calls. I had a bunch of meetings.

JIM O'ROURKE [00:13:09]: I generated a bunch of excitement. But at the end of the day, I couldn't get anybody to pull the trigger because of print media. You know? Because, you know, analysts at the smart smart analysts at these PE firms Google print media, and it's not hard to get a lay of the land for what has happened over the past 20 plus years with print. So, you know, when it comes to making shrewd investments, which these firms do, this was a showstopper. I couldn't get any commitment. And then, so then I had figured out, I never—when you work for a company, you don't learn how to buy businesses. You don't learn how to do all the capital stuff behind the scenes. And so I had so much more respect for the folks I was working for at GateHouse after I stepped into this role.

JIM O'ROURKE [00:13:55]: Like, all these things that I had to do all of a sudden weren't so automatic. I had to do them and learn it, and I learned pretty quickly because I like it. I, you know, I'm intrigued by how this all works and how to buy a company and raise money and all. So once I realized I wasn't gonna get the funding I needed, I made a connection, you know, when I was looking at these companies for Eli Global, with Emerson and Suzanne Lynn, who owned the St. Albans Messenger, which is one of the companies we were gonna buy. And we just said, can—let's figure this out. Let's figure out how to make this happen on my own. They were willing to do some things to help me out on the finance side.

JIM O'ROURKE [00:14:37]: I was able to, I learned how to get an SBA loan. I had some of my own money, and to cut to the point, we figured out how to get that deal done. Andfrom that point on, that was December. We closed on that business in December 2018, and there was commercial real estate involved and all, so that was a good part of the bank structure and terms that could be managed for the business. And then but I got halfway into that year, that first year in 2019, and I was like, this isn't enough. This, first of all, this business isn't big enough to support me and my family. And then, I was getting antsy because I was still living in Chicago, and I was going back and forth to St. Albans every week.

JIM O'ROURKE [00:15:23]: I was running the business, a nice $3 million company. So I started studying, well, how can I get, how can I buy another company? So, I did that early on and figured out how to do the second, add the second business into the mix in Wisconsin. And Kiel, Wisconsin was the first business. That's where I connected with Joe. Joe Mathes was the brother of the guy that sold me the business in Kiel, and he was part of the deal structure and had a little bit of equity in the game in terms of the Wisconsin part of my company, and he stayed on to help run the business. And, the attraction when I went into Kiel was Joe had built a digital agency there in their, you know, smaller business, and it was pretty cool what he had done pretty much on his own. And my attraction there Joe and I hit it off, and my other attraction there was, woah, we can take that agency and we can expand it, and we can support all the newspapers that we buy. So that's kinda how the digital biz part of our business got started here.

JIM O'ROURKE [00:16:29]: And then it just got crazy. Another, we bought another business in Wisconsin and—which was about an hour from Kiel, you know, an owner that was selling and retiring, and then COVID hit. And so then we had to figure all that early on, figure all that out early on. And COVID was an interesting time period for us because I think, I forget, we bought six or seven companies during the heat from the start of COVID to the end of COVID. So that that was some serious risk taking to I was all I'm still all in on what I what I do personally and financially, but at that point, it was like the whole company was riding on some of these companies we bought. And we figured it out, and we got a lot stronger during COVID. I was lucky I was able to bring some serious talent into the company. Some with the companies we bought; others recruited from outside. And then as soon as COVID calmed down, we just took off. And we've been on a pretty good run, you know, that there's been challenges.

JIM O'ROURKE [00:17:36]: The revenue isn't always what it needs to be, and cash flow gets, you know, stressed at times. But generally speaking, we're, I think, what, if I'm talking to an outside investor now, my lead pitch is, you know, we have figured it out. And that's what kinda keeps myself and our team driven and moving forward at a fast pace.

Why local news is still a great investment

TIM REGAN-PORTER [00:17:59]: That's quite remarkable growth over, what is that, six years almost? Some somewhere around there? Going back to that first purchase, so I meant you were obviously well steeped in the industry. But, you know, coming in as an owner, what were you seeing that the PE and the other investors you were seeking out not seeing? Was it just the size of the return they wanted or was there something else?

JIM O'ROURKE [00:18:25]: Well, investors never really get it. I guess some of them do. I haven't come across many. Some of them think they do, but they don't. What I see is, like, these established brands and trusted brands, established brands, tons of advertising relationships. I mean, in our small little—and I we're I still think we're tiny, but, you know, we do business with 15,000 advertisers a year. And to me, like, that's, like, that's impressive. I mean, that and I've over the years, I've, in my own company as well as for other companies, I've tinkered with establishing new brands and saying, oh, yeah, you know, this will work. Brand new, white, no debt.

JIM O'ROURKE [00:19:10]: And we start from scratch and we just—that's hard. That's a hard path to go down. So I just have such, I have a lot of admiration for these brands. Sometimes it comes across as wrong. I think that, I think our business in Vermont is the oldest operating business in Vermont. And so that sounds good, but it also sounds like, is it a grandpop company? Is that a dinosaur? No. It's been around 200 years. It's not if we do the right things with our audience and with the news that we provide and we're going to

JIM O'ROURKE [00:19:43]: be around for a long time. Like, we're not going anywhere. Right? So that's the attraction that I have with it, and investors don't give a crap about that. They, most in the PE world want a return. Like, if I buy, if I invest x, you know, how fast can that triple and quadruple? And I learned right away after a lot of pitches. Even as I've been established as a company now, it's easy for me to go out and raise money to try to do more. But I, this is not an invest and exit type of a business, and I learned that even when I was working for bigger companies because I didn't realize it at the time, but the expectations were always unrealistic. And what at one point for a segment that I was responsible for in GateHouse, we were running my region at, like, a 25 or 26 or 27% profit margin. And, like, this wasn't that long ago, maybe 10, 12 years ago, 13 years ago.

JIM O'ROURKE [00:20:43]: And it wasn't enough. It's like, so I'd be pulling publishers over the table to cut costs, you know, in a business that may have been running at a 35% margin because I was doing what the company told me to do. And now when I look back and I'm like, oh, my god, I would kill to own the Taunton Gazette right now. The business that I ran from 2008 for a few years. And, you know, the thing was a cash cow. You now, $5 million company making a million and a half bucks a year, and it was never good enough. And so that's the beauty—of course, you know, you gotta make money and, you know, you gotta be profitable to fund everything you wanna do, but the just as important part of this is the freedom to keep working to build a company that doesn't act like what I just described. And we don't act like that. We're not in this to turn this and sell it in a year. Like, I don't have an exit strategy. We're gonna be in this for a long time.

Balancing sales and editorial resources, local and centralized support

TIM REGAN-PORTER [00:21:46]: Yeah. And the markets you're in, the types of papers you're running, I think are often underestimated by people outside of the well, even inside the industry because the big metro dailies get a lot of the attention, and, certainly, they're important. But I've seen the financials of some, you know, some of these smaller midsize city papers. And a lot of times, you know, in the chain, those smaller papers might be producing the bulk of the profits, while the big city, the metro dailies have really high top line revenue numbers. The P&L often in these smaller papers, can be really, really healthy. And I think people don't understand just how because of those advertising relationships you're talking about, how central they are to the community and how they can really be very viable businesses, you know, for some time.

JIM O'ROURKE [00:22:41]: Yeah. And, you know, Tim, I would have and I might come across as a little cocky with this, but I really believe that should be the case in all of the media markets. And I don't know. It's like companies, the financials when you look at public traded companies, most of the financials aren't that exciting to follow. I don't get excited when I see a company tooting a horn about digital's at an inflection point, you know, 50% of our revenue, but profit's down 25%. And I'm a numbers guy, and I don't get how all that math works at the end of the day. It doesn't work. It's the problem.

JIM O'ROURKE [00:23:21]: And so, and I just think it's a result of a lot of, like, forced and bad decisions. And I don't think this is any more it—I don't want to make this, it’s not easy, what we're doing. But to me, like and how I look at OMG, sales runs my company. So this is a podcast about local news matters. Right? But sales has to run my company to pay for everything that we wanna do with content, with technology, with managing data at a higher level as we progress and figure out AI and everything we wanna do as a business, sales has to fuel that because that's my belief as a business. We're for profit, and I'm not out seeking donations. I'm not on the philanthropic route.

JIM O'ROURKE [00:24:08]: I'm not like, we have to fund what we wanna do, including the debt structure that I've used to build a company. But the sales company could be great, but if my products aren't doing what needs to be done in each of these communities, it doesn't work either. So I say sales runs the company, but at the end of the day, a reporter and an editor, those resources and that talent is just as important as the sales side of the house. And that's, I think, balancing those two, and, like, that's the name of the game here. And I don't think it should be, it shouldn't be much more complex than it was 30 years ago. It should be more exciting because when we produce great content, we can get it out to a lot more channels. And I'm a big student in this and following, you know, what people are doing that's working. And so if you have the sales engine and you can create the resources you need, like, we're focused right now on getting our newsletter game on.

JIM O'ROURKE [00:25:08]: We are gonna build a kick ass newsletter part of our company and our local markets, and I know it's gonna work. So, but it's not gonna work though if I don't get the news teams the resources they need to do it really well and the salespeople, the training, and the focus to monetize that audience. So it all has to come together like that for this to work. Again, not easy. The people parts of this on both sides have to be right, and that is not easy. It's easier to talk about than to do.

TIM REGAN-PORTER [00:25:39]: Absolutely. And you referenced, you know, looking at some of the public companies' reports and, you know, bad decisions. And I think some of this is armchair quarterbacking, but some of it I've seen very much firsthand. Some of those bad decisions relate to a tension, I imagine, you deal with regularly, and that's the tension between local and centralized resources. And I think some of the bad decisions that some of those public companies have made is, you know, they've decimated their local product and by getting rid of local people and focusing on shared coverage, where maybe there wasn't a lot that the audience shared. And the same with the sales team. They've tried to centralize all of that and lost their local connections. And just from afar and seeing how you bought some papers in Colorado, was it I think it was just last year.

TIM REGAN-PORTER [00:26:31]: And so I've seen a little bit of how you've interacted there, and then just following you on LinkedIn. I have a feeling from what I've seen and read that you value the local aspect very much and just talk about how you think through that. Certainly, chains and private equity are kind of the boogeymen of the industry right now. So, yeah, what do you bring to it from there's a benefit and what's there locally that you try to preserve?

JIM O'ROURKE [00:26:57]: Yeah. And we have been very intentional with this. I have been from day one, and let's just use Colorado as an example. Really, the only one that's not local in that business in Salida, the other markets within our Colorado group, and then Pagosa Springs. The only one not local is me, and I don't have a problem saying that. I don't have a problem telling employees that. It's, I don't know if I'm telling customers that or if I'm at an event in one of those markets. That's my business strategy.

JIM O'ROURKE [00:27:29]: Now when I'm there, like, do I wanna stay there? Yeah. I don't wanna leave. I wanna make that my own. I wanna be there 100% of my time and just focus on Colorado. And that would be fun. And I feel that in every single market when I go into it. The reporters, the editor, the salespeople, they're local. Sales management, most of it is local.

JIM O'ROURKE [00:27:52]: Anybody that is customer facing or in front of, like, covering the community, 95% of that work is local people in those local areas that we serve. We're smart about what we do on the back end. And this I learned along the way just because it was the best way to scale. I mean, if outsourcing makes sense and you can save money that can get pumped back into sales and news, fine. I'm all about it. The cheapest way to get it done. But what I have found is to move the work to where you have people. Our two graphic designers in Vermont design ads for our team in Minnesota.

JIM O'ROURKE [00:28:31]: We have somebody that's in charge of process and IT that works in Hudson, Wisconsin. She's very pivotal in supporting Colorado on anything that can surface on the back end process improvement related technology systems. So, like, we streamline. Our processes are consistent across the board. Any one of our markets you can plug in and we can support each other no matter where anybody is. So that's and so the work is shared. We create jobs by doing that. We protect and maintain jobs with this approach.

JIM O'ROURKE [00:29:04]: I don't have any intention to outsource ad design. My ad designers are talented. They're in the markets that we serve. They might do cross market, but I like that. I think that's smart behind the scenes. Our director of digital fulfillment lives in St. Louis. She's not in any of our markets, and she is fantastic.

JIM O'ROURKE [00:29:25]: We, it's, so we've kinda and it's something, quite honestly, that came out of COVID. You know, we learned the value of office and hybrid like a lot of companies did, and we've maintained that. If you have the right people that are driven and are and can work independently without a whole lot of supervision, it works brilliantly, and that's kinda what I think is one of the things that's working for us.

The importance of maintaining brand trust and relationships

TIM REGAN-PORTER [00:29:49]: Yeah. And one of the things I read where you were talking about what you look for when you buy these publications, you want that brand to have been well managed and maintain those assets, those local connections, those business relationships, that reader relationship. You talk a little bit about that?

JIM O'ROURKE [00:30:07]: Yeah. I mean, that just makes, if there—you can make an argument that, you know, why would you buy newspapers? You know, why would you take this headache on? Why not just, and I was, I've worked through this on my own in my head as to, like, why would I just keep buying these newspapers? Most newspapers I've bought haven't been thriving. You know, that doesn't mean they weren't well run and they weren't still generating cash flow and profit and had respectable brand. I'm just saying, like most people selling their newspaper business, they're selling it because nobody in their family wants it or they're at the end of their run. They wanna retire and do something else. But very seldom, if I bought a company and have it just take off on its own. So, you know, that part of when you, when I look at these companies and, like, the brand still being relevant and the content still being strong, some resources still being there in sales, and cash flow is important. I mean, you know, when you use debt to buy companies, the cash flow has to fund, you know, all the resources plus that debt structure.

JIM O'ROURKE [00:31:20]: So that's why I kinda try to hedge my bet on this being a great company. Like, when you're doing all of your performance and assumptions before you buy, you have to say, alright. Well, this has to pay x for the loan. And then we're, we know at this point what it's gonna take to build digital and what it's gonna take a lot of time. I would say in 90% of our deals that we've have done in six years, we end up having to pay people a lot more money in all the key roles. You know? So we've made a concerted effort to pay reporters more money to keep them from leaving so fast. We've had to invest in our sales structure where sometimes a company, you can get away with paying under market. But if you wanna sell digital and you wanna sell omnichannel and you wanna really grow revenue, we're serious about growing revenue.

JIM O'ROURKE [00:32:09]: So we put our money where our mouth is to get the best sales talent we can get in the markets we're serving. So all this stuff comes together. Now I've taken on some distressed businesses as well, you know, of, like, one of the business deals we bought during COVID was they were shut down at the time because they just financially couldn't make it anymore. So that was a case where you go in and you bet on the management team you have in place and your own company's ability to turn it around and do what the previous owner couldn't do, including building positive cash flow. So I'm not afraid of those situations. It just has to be right. The financial part of it has to be right, and it's gotta be, not airtight, but the path forward has to be pretty direct as to what we think OMG can do if we got our hands on these assets.

TIM REGAN-PORTER [00:32:59]: Yeah. And, you know, there are a lot, hundreds, thousands, of small print publications around the country, and a huge percentage of them are, you know, the situation you're describing. The family's owned it, and the kids don't wanna take over, and they're gonna need to turn it over. And I think there, you know, there's some warning there that you wanna preserve the core value of your asset. Right? Before everything declines too much, you need to make sure you keep your journalism strong, keep those sales relationships, and think about that evolution. You know, for these small, family-owned publications in particular, I've talked with a lot of them, and some of them are very wary of selling, particularly to an out of state chain. What do you say to them to alleviate fears that this is not gonna be one of those horror stories they hear about?

JIM O'ROURKE [00:33:52]: We have a little bit of a track record with this now and, you know, everybody that I've bought a company from was a really good operator, had really good connections and roots in the communities and in the industry. So you can do your homework now on who you're selling to, and I know if you call one of the owners, the sellers that I bought from, they know how it has gone. They and because I do exactly what we say we're gonna do when we go into a market. So I get disturbed and a little agitated. Like, say, in the Salida business acquisition, I didn't even view ArkValley dot online as a competitor, candidly through due diligence. I didn't view them as a competitor. And so, but so they did a nasty story early on, and I felt it was kind of interesting to me because—and I called the guy. I forget the gentleman's name, and I called him.

JIM O'ROURKE [00:34:49]: I'm like, before you did this story, the—first of all, what did you accomplish? And, yeah, your website says you're the truth or something that you report other truth matters, and you just printed a bunch of stuff that's not true about my company. And then, so I was all worked up about that at first because I was pissed. And I was basically a hedge fund from Chicago or Arizona. I forget at the time. And they said a bunch of BS, about, like, this—they basically locked me in with hedge funds, and I took offense to that because that's just not, that's just not how we do business. And if that reporting entity that the truth matters did their due diligence, they would have known that about me. I mean, who did you talk to? Oh, we talked to one reporter. Where? They, of course, they wouldn't tell me.

JIM O'ROURKE [00:35:37]: And because, I mean, maybe we had a disgruntled reporter that left at some point over the last six years. Who knows? But now I don't see that entity coming back and saying, wow. What because I can tell you, and I'm, again, I'm not egotistic about this, but my team in Colorado is killing it. We have a new editor that's doing a fantastic job. We got two awesome reporters in Salida. We got a great editor and reporter team, and at the Chaffee County Times. The Herald Democrat in Leadville is, I mean, these newspapers are doing a fantastic job week in and week out covering these communities in Colorado. And then in Pagosa Springs, it's like, holy crap.

JIM O'ROURKE [00:36:19]: Find me a better weekly newspaper in Colorado or I don't know every newspaper in the state or the country, but I don't know if we could do a better job in Pagosa. I mean, that newspaper is outstanding. And Shari and Randy and the team there just, they were already in place. I just bought it and say, woah. I'm gonna stay out of your way. I'm gonna work with you on building up the business, on building up digital, and getting more efficient. And so to me, like, if I did a bad story about a pure company, I'd be big enough to go in there and do a positive story two years in on saying, you know, we were wrong about this. And then whatever.

JIM O'ROURKE [00:37:00]: So that was a hot button with me, but, in terms it's a long winded answer to your question, but we're, we don't always do the right thing. I mean, you make judgment mistakes at times. You make people mistakes at times. But generally speaking, I think I'm pretty happy with how we transition businesses into our company.

Expanding digital while avoiding paywalls

TIM REGAN-PORTER [00:37:21]: Talk a little bit about the digital side of it and helping—I imagine most of these papers you've bought, and then I'm sure there were exceptions, but most of them probably did not have the strongest digital side of their business. Right? So what's been your approach to building that?

JIM O'ROURKE [00:37:38]: That's a great question. With the exception of our business that I alluded to earlier in Kiel, just about every market we bought into was at zero digitally. They may have been tinkering with audience growth online and paywalls, dysfunctional paywall strategies just for the reason that we're not putting our stuff out there for free. So as we sit here today from a macro perspective, we're right around 30% of our total company revenue is digital. And that's been pretty stagnant for a year and a half for a lot of reasons. In some businesses, digital is more relevant than others. But, generally, we've, we go in and, like, I'm anti paywall. So if there's a paywall up, we go in, we drop it.

JIM O'ROURKE [00:38:27]: In some cases, in the case of Pagosa Springs, they still have a paywall up because they believe strongly in, you know, keeping their news behind that paywall, and it helps print and all that. So that works for now, but at the end of the day, our strategy is no paywall, and we're betting on monetization through advertising of the audience. And we've seen that. I mean, the problem with being free online is you can, we can negatively affect print readership and print subscriptions. But I've been okay with that because print subscriptions in a weekly newspaper do not pay, they don't pay the bills. It's five, 10% of the revenue, and in a lot of cases, it doesn't even cover the cost of a reporter. So why am I gonna keep my audience down and not get in a position to take advantage of first party data and newsletter strategies and building up multiple channels? So pretty much regardless of the circumstance, we're gonna drop the paywall. We're going to focus on providing great news and get better at it more timely. Don't let the print production cycle run the show when it comes to what we publish and push out.

JIM O'ROURKE [00:39:42]: That's still something we're fighting, believe it or not. Like, we're still print too print centric in some markets, and the more progressive publishers and editors get it, and they're knocking those walls down. In other cases, we still got some work to do where the lion's share of the work for our Friday publication is happening on deadline on Wednesday. I don't get that. I don't like it. So we're in the process of changing it. The other big factor is hiring, recruiting, hiring, training, the internal support. The digital agency within our company is a really big factor to our strategy.

JIM O'ROURKE [00:40:18]: Content is in the center of everything we're doing, but on the revenue side, the agency, you have to be cutting edge. You have to be on the right side of understanding digital because, ultimately, that's what that's what our customers want. And if you and even in our rural markets where you think digital isn't as much a factor, that's BS. Digital is a factor and a necessity in every single market we do business in, and I would say every market in America and investing in the agency to like, our agency is internal. Everything we do, we fulfill internal. We, our team is internal. We, our agents, one of our agency's biggest jobs, if not biggest job, is to work with each of the markets on what they need to do to build new revenue. And, ultimately, done right, we have proven that when you do this right, it does produce cash flow, and it does go into the pot that you need to have a viable business.

JIM O'ROURKE [00:41:19]: So they're working hand in hand. The core newspaper operations have fueled the birth and growth of an agency. Now the agency drives the revenue growth that you need to continue to have what I think—I think the strategy ultimately needs to be, how does this business look when you're digital only with content, and then you got a digital agency, and then you do other things that publishers, quite honestly, have always been great at, whether it's printing and design or just figuring out different lanes of how to generate more revenue around your business assets. And that's where I think print falls still. Like, print, I think, is still gonna be a viable medium when done right, when the product is great and the price is right. You don't gouge people with the price. I think print will be a relevant part of our business for the next five, 10 years, and I think we'll have arrived when revenue is 50/50. When half the company's revenue is print and half is digital, I think we'll be sitting at a business that starts to settle and becomes easier to manage for growth.

Relaunching print in Milton, Vermont

TIM REGAN-PORTER [00:49:12]: So we've talked a lot about digital, but your publication in Milton, Vermont just relaunched their print publication, that they had stopped during COVID. So talk to me about going back into print.

JIM O'ROURKE [00:49:23]: I was so proud of that first edition. It looks beautiful. The design is perfect. Loaded with ads. And this is just hey. It was a, they were a victim of COVID. We had three weekly newspapers in Chittenden County there in Vermont, and, you know, we lost a bank and a few big advertisers. The group of weeklies was already stressed financially.

JIM O'ROURKE [00:49:48]: They weren't doing well before COVID, and it's almost like the COVID and the—we're stopping our advertising was the knockout blow. And at that point, it was a lot of just do and think later, and that's what I did. You know, I just said, we're, I'm not gonna keep printing these newspapers because we don't have the backing to lose money here. And who the hell knew at that point how long COVID was gonna last? I mean, when I, when we stopped printing those, like, things were shut down. Like, you couldn't leave your house at that time. And so, so, anyway, we learned very quickly when things normalized and when we got the right. We worked through a lot of turnover in Vermont during COVID as well. It's like people woke up one day and said, oh, I'm gonna go do something new with my life.

JIM O'ROURKE [00:50:31]: And so we worked with turnover with key news positions, key sales positions, and a lot of other things in that business. So when things normalize, we got the right people in place, we just felt—and I give Bridget a lot of credit and the whole team there in Vermont a lot of credit for saying people really want print back in this market. And, our first pub there that we brought back was in Essex, which was the town over from Milton. Essex came back last August of 2023, and, you know, the team did a fantastic job. The paper's awesome. They're really doing a good job balancing monthly print with everyday digital and newsletters. We can get better with newsletters, which we're working on, but I'm really liking this model. I don't think monthly print works on its own, but the reporters in these cases like, if you look at that Milton website today and compare it to the print product, I mean, Milton is the newspaper of record in Milton every day of the week.

JIM O'ROURKE [00:51:38]: Things are posting to that website every day, and the same is the case in Essex, and then we're coming over the top with a monthly newspaper that's done really thoughtfully. And, you know, it's more enterprise news driven, more like, you know, not everything's as timely as you would be. But to be quite honest with you, not everything's timely in a weekly newspaper either. So I think we're really finding our stride with this. And, look, if the monthly helps fuel the growth of a digital media company that could stand on its own in Milton, Vermont, five years from now, this could end up being the smartest thing we do. What we do know is digital alone did not work. Like, we didn't close shop completely in these towns during COVID. We went digital only, and we maintained a reporter, and we maintained sales focus, And we proved pretty quickly that milton.com alone, Milton Independent, it doesn't, it's not a viable business yet.

JIM O'ROURKE [00:52:37]: So that's why I'm so engaged into, like, how this monthly thing could work because from an advertiser perspective, it's gold. I mean, you're getting in, we're in every mailbox in town. 100% of the households in these two towns get this newspaper once a month. That's a great cost effective offer for an advertiser.

The challenges of printing presses

TIM REGAN-PORTER [00:52:59]: Yeah. And as you said earlier, I think print has a lot longer shelf life than some people give it, partly because consumers want it and partly because it's a key differentiator, and advertisers appreciate it as well. My biggest concern with print are the printing presses. And you know how challenging that is. You've got some. And then, you know, in Colorado, we lost two big presses in the past year or so. So how are you managing the press side of the business?

JIM O'ROURKE [00:53:29]: I have to be candid. When I don't, I didn't love being in the printing business. Most of the companies I bought were already outsourced. After I got my arms around Vermont, I couldn't wait to get outsourced. So it's just, I need to spend my time on building revenue, on building the team, getting the right people. You always have to have an inroads of talent coming into the company, and then you gotta keep people happy. Like, I wanna put all my time in that, continuing to grow. You know, I want us to be in a hundres markets, you know, as fast as we can, but as intelligently as we can over the next few years from where we're at today.

JIM O'ROURKE [00:54:13]: When you're in the printing business, it can pull you into a lot of things that don't align to what I just outlined. And so I have to be honest, when I went into Colorado, I didn't know anything about it other than the previous owner was frustrated with it, and he kinda just kept it going because he knew he was selling. And, but I got in there, and I met the people. I saw how strong their relationships were with our commercial print customers. I mean, I don't know the exact years, but Salida has been printing some of our commercial print customers for decades, and I don't I don't take that lightly. That's a big responsibility. That's on, to me, that's almost a bigger responsibility is making sure people get paid every other week. So, you know, so there's kind of a vested interest in figuring this out.

JIM O'ROURKE [00:55:07]: And so I hunkered down, and I changed gears quickly from wanting to outsource printing in Salida to investing in it. And I kinda silently, I didn't tell anybody this, and I probably shouldn't be saying this here, but I started treating that printing operation like it was the digital agency, and it just needed some investment. It needed some people. It needed some resource. We can't get mail-insert people into the mailroom. Well, you know, we're not, you haven't been paying them enough, so we've had to reset the wages at a much higher rate, a much higher rate. All of this stuff, I didn't plan for. I was just gonna come in there and get out of printing and build digital because digital is at ground zero in this business.

JIM O'ROURKE [00:55:47]: But I have flipped the script big time on this one, and we were able to, we've been able to bring in some really good talent. The pressman, the lead pressman, and he's the best press guy I've ever worked with in an internal setup. The downside of it is that he's older, and he wants to retire at some point soon. And so that's the risk. That's the threat. You know? It's so hard to find somebody to come in and run a community Goss press, and then all the other factors. You know, moving into Salida now is a nightmare. You know, you're gonna spend $500,000 on a basic house where, with not a whole lot of land and not a lot of room, and so it's hard to solve this problem.

JIM O'ROURKE [00:56:32]: We're lucky because we got our, we got Morris, our top pressman. We got one down guy in the press room that's been doing this for 38 years, and, you know, so we got a good thing going on. Our commercial print customers love the service we provide, so I'm in it. I'm actually, I'd like to expand. We've recently taken on some new printing customers. We're printing Aurora Sentinel now. Dave moved his business to us last month, and that's going exceptionally well. He's pretty happy with what we're doing, and we're happy to do it.

JIM O'ROURKE [00:57:08]: So we're just playing, we also print in Pagosa as well. I've spent a lot of time with the team in Salida on building out things. They're doing all the work now. Like, don't like, I'm not in there running the press. I just try to help them with whatever I can for resources. But, in Pagosa Springs, I have spent since September of last year, I've probably spent 20 minutes on the press, the pressman, and printing in Pagosa Springs. Guy, Robert, from printing there. He's independent. He's efficient.

JIM O'ROURKE [00:57:44]: Him and Sherry work together, my publisher, on keeping things going. They, in that case, we just print ourselves, and we have one smaller commercial print customer. And, look, I could come in and be bullish and say, I don't wanna be in the printing business, but I know two things here. When you have the right people, it works, and it's profitable. Pagosa is a very, very, very profitable business, and so whatever we're doing internally, that's not something to disrupt. We're gonna keep it going. And from what I understand, with the right maintenance, these presses can run another 10, 20 years. And so, that's where we're at with printing that and we still print out of my business in Delaware as well.

JIM O'ROURKE [00:58:31]: We have a niche advertising business in Seaford, Delaware, and we print 45-50,000 papers a week. And that team as well, just great press, great team, great pressmen, all the operational firepower in house, profitable business unit. It's almost like, you know, you have good control over what ends up being a very important part of your business. Last time I checked, print revenue is still 70% of what we do. So behind the scenes, we treat it like that.

TIM REGAN-PORTER [00:59:02]: Yeah. Yeah. So that that's a good endorsement for any foundations or investors who are getting approached about printing presses. That again, that's my biggest concern for print. It's not the demand. It's the supply side. And it's challenging. You had to deal with everything from tariffs that jacked up the price of paper and ink to outdated equipment to finding the people. That's a big problem. The they're aging out. And I you know, my understanding too is the biggest issue, what's impacted newsprint is, more than anything else, is Amazon, that a lot of the manufacturers went to producing cardboard boxes because that's where the demand is. So that's why newsprint has gone up so much.

JIM O'ROURKE [00:59:43]: I still don't understand after many conversations what the tariff issue is. I didn't notice it until a charge for plates went up 80 or 90%, and I still don't understand what's going on. I think there's some kind of a meeting this month in Washington about this. I don't think the sales guy's BSing me that sells plates, but our plates went up, like, 80 or 90%. And, apparently, it has something to do with them being manufactured in China, and they're either gonna fix it and resolve it and eliminate it, or it's gonna continue. I'm like, you know, you can't even make this up, but it's what you deal with in the printing business. And, overall, there's always things like this coming at you and what we do, and you just gotta, you gotta build to absorb it and adapt. Right? That's the only way I know how to deal with these things.

Lessons from working at Berkshire Hathaway’s World Book

TIM REGAN-PORTER [01:00:30]: And then the last question before we get to the rapid fire, talk to me a little bit about working at World Book. You know, that was of course, you know, Warren Buffett's never been shy about going against conventional wisdom and investing in businesses, sectors that people had written off. But, you know, the encyclopedia business was certainly one of those. And, it seems like there are a lot of parallels with our industry. But, you know, you said it wasn't really just a it wasn't a print encyclopedia business by the time you got there. So was there anything about the evolution there? And you even alluded to the pace was different. What do you take from that experience coming back into the industry?

JIM O'ROURKE [01:01:09]: I learned a lot about running a business at World Book because one of the things I admired about Berkshire Hathaway and the—I worked, I was, we were owned by a subsidiary under, so my boss ran a portfolio under Warren Buffett. So I worked for a CEO who worked for Warren Buffett, and I really admired the autonomy. Like, we had our own business office. We had our own bank accounts. We had our own like, you were really on your own. And even though it was a smaller company at the time, I dealt with a lot of things in that business that I didn't have to deal with in the corporations before that I worked for. And so I gained a lot of insight. I gained a lot of learning about people and how to manage things more autonomously.

JIM O'ROURKE [01:01:54]: You know, once my boss trusted me there, I talked to him once every three, six months, or I think he even went nine months at one time. And I like that because I never needed my boss to kick my ass to do my job. I actually, it's actually the reason why I left most jobs because so and so was acting. I didn't like how the person above me was acting. So once I built that trust, I learned that, woah. Like, this is why Berkshire is such a great company because how Warren Buffett treats each of his businesses rolls down. Like, that's how my boss acted. And if you're doing your job and you're hitting your numbers and you're growing, just leave the hell alone.

JIM O'ROURKE [01:02:33]: So I felt like I own my own business, and that was a really great feeling for me because, again, like, I don't like being micromanaged. I don't ever wanna be in a world where my boss is breathing down my neck again because I never needed that to to do a good job, and a lot of people don't. So from a business perspective, it was really the same. It's just a matter of identifying who your customer was and who your audience was for the products. Most of our stuff was being, you know, done online, so it was a matter of knowing our audience, what's engaging kids, what's engaging librarians, and so there's a lot of similarities. And I could've ended up staying there for a really long time, but, you know, life just spun me back into this.

Rapid-fire questions

TIM REGAN-PORTER [01:03:18]: Alright. So rapid-fire questions. And the questions are quick, but your answers don't have to be. So compared to a year ago, are you more or less optimistic about the future of local news?

JIM O'ROURKE [01:03:28]: I would always answer this no matter what time period you put in there as way more optimistic this year than last year. But I've been saying that now, Tim, for 20 years. So I just love it. I love the adrenaline rush of figuring it out. You always want more money in the business bank accounts to ease the pressure a little bit. So, you know, but I never thought, there's not been a more invigorating time to be in this right now. You gotta feel that, or I don't think you can stay motivated and in the game to figure it out if you don't feel that way.

TIM REGAN-PORTER [01:04:11]: Does AI fill you with more hope or dread when it comes to journalism?

JIM O'ROURKE [01:04:16]: I think hope. I think AI is gonna unlock a lot, and I think it's gonna change fast. I think AI is gonna get so sophisticated, and it's gonna just do so much more. But I've kind of been in a back seat on this one, you know, watching and learning and trying to figure out where to steer the company as it relates to AI. You know, I don't, it's not too embedded. It's not hardly embedded in our newsrooms right now. I'm sure certain editors are tinkering with it and, you know, using it where it makes sense, but we're finding that still requires editing and checks for your accuracy as well. Like, I spend time on in AI, and I research things, and some stuff comes out perfect and other stuff comes out like, what? Are you kidding me? Like, what if we just ran that? So I think it's gonna come down to figuring out how to leverage AI as a tool, and I think those that do that will be just fine.

JIM O'ROURKE [01:05:14]: We're, we have great success with AI on the business side. We're using it to write copy on websites. You know, we're using it for certain things to market ourselves to, our controller was working on letters to help collect money last month, and he sent me three perfect letters to send to different layer levels of people late, and I'm like, wow. This is perfect, man. How'd you get this done so fast? And, AI, ChatGPT. So from that regard, like, it's just gonna change a lot with how we do. But, ultimately, I think it's just gonna be another great tool. I don't know how to run from it.

JIM O'ROURKE [01:05:51]: I don't believe, I think I heard somewhere at one of the conferences that, you know, this is more of a reason to put your content behind a paywall. So ChatGPT and these other, Gemini can't grab it and do good luck with that. I'm not a technology expert when it comes to that stuff, but I don't see how that's gonna stop the AI movement from, you know, protecting our content.

TIM REGAN-PORTER [01:06:14]: Do you have a favorite piece of advice that you've been given or you like to give?

JIM O'ROURKE [01:06:19]: Would you accept more than one answer here?

TIM REGAN-PORTER [01:06:21]: Sure.

JIM O'ROURKE [01:06:22]: Some of this, some advice that sticks in me a lot is, it's just when it comes to business results and pressure. And I try to roll this down as much as I can. It's not life and death. So to me, I've always been able to balance pressure no matter if I was working for a maniac boss or just my own drive to have better numbers than maybe we had in a particular period. I just don't think I don't think there's any greater pressure than, I worked through it with my mom. You know, she died young, and, you know, when you're in a hospital room and a doctor comes in and gives you six months to live, that's like no pressure I ever deal with will outdo that. So that's what always keeps it in perspective for me, and pressure breaks people. It stresses people out, and when you drive hard for results, you're always gonna have to balance how you administer pressure because, unfortunately, everybody just doesn't do what they're supposed to do without being pressured.

JIM O'ROURKE [01:07:22]: But, man, if we can just keep that perspective, that I haven't come across many business issues that weren't fixable, and that's what I try to encourage, and, the life and death thing is pretty sage advice. I learned early on that impatience is a good thing. I learned it from a test that a company did with me, you know, decades and decades ago. I thought it was a negative, and I was like, oh, crap. I'm impatient, but I learned, over the years, lots of maturity and a lot of experience since then that, you know, you'd really, you go a long way to get impatient people into your company because impatient people are never satisfied. They always want more. They always want to keep going, and I've learned to really harness that. I'm as impatient as you get, and I try to have people around me that are impatient as well.

JIM O'ROURKE [01:08:18]: The seller, the gentleman, Merle, who sold the business to me in Salida said something very nonchalantly to me over dinner one night when before we had bought the company, and he said, you know, those who serve the best profit the most. And that that stuck with me, because, man, that and then I as you study that more and you read books about people and that a lot of successful business people, that's core to their belief, and that's core to the way they behave as a company. So that was pretty impactful.

TIM REGAN-PORTER [01:08:56]: Is there a piece of common advice or conventional wisdom that drives you crazy in its simplicity or oversimplification?

JIM O'ROURKE [01:09:02]: I don't wanna take shots at companies and people betting on these things as an industry, but paywalls and digital subscriptions are not the solution for the local news media industry. It's clearly working for New York Times, and there's big time niche brands that can have, clearly have figured it out, but I just don't. I think it's really simple path forward to not do that. And I don't think begging the government for assistance is a viable path forward. I just again, I hope it works. I hope all the movement to get government to knock Google around and kick back money to all these local markets. I can't visualize how that's gonna happen. I, like, I can't visualize calling Google and saying, where's my share? Or, hey.

JIM O'ROURKE [01:09:51]: You didn't wire the money to me this morning for all that news you stole from me. And I could be nonchalant and uneducated about it, but my gut instinct is telling me that I wouldn't wanna bet my company's future, especially with what's going on now in government and politics. I just would not, I wouldn't wanna be hinged to that right now. I think the path forward is for us to figure out as, you know, as business people. And, again, you know, I hope others that are betting on those two tactics. I hope it works. I sincerely do.

TIM REGAN-PORTER [01:10:27]: Do you have a favorite failure of yours?

JIM O'ROURKE [01:10:30]: Yeah. I—favorite and failure is a tough one to answer, but our expansion into Virginia was a failure, and it was probably my biggest mistake since maybe in 10 years. And so, and selling it was the right thing to do. You know, a couple of our key people got hired, and they're really going to enhance the ARLnow, which is a really neat business, by the way. You know, Scott's really done a good job figuring things out. Any digital entity that's been around 15 or I forget how many years they've been doing it in a very competitive market. I just, I watched him for two years, and so it wasn't hard. Like, I called him out of the blue on the weekend and said, dude, you should buy the Gazette Leader

JIM O'ROURKE [01:11:22]: This would help your business, and it's not working. I, we could have made it work there, but the market's too competitive. We had a hard time getting the right people in place on the sales side, and our model doesn't again, like, if I go to Virginia and live there for three years, I could build a fantastic media company, but that's just not my model and a few of my key lieutenants getting getting stretched into Virginia didn't work either. So in this case, selling that was the best outcome, but that doesn't hide from the fact that financially, this was one of the dumbest things I ever did in 10 years.

TIM REGAN-PORTER [01:12:02]: You know how stressful this business can be, and imagine as you've acquired more papers, it hasn't gotten easier. What's one thing you do to restore yourself and maintain your sanity?

JIM O'ROURKE [01:12:14]: Yeah. Again, that's tough one. That's a tough one thing to answer. Training, you know, four times a week weight, really into weight training and hiking complex mountains. And I like Robert on Shark—I'm a big fan of Shark Tank and, you know, I was, I follow him on something, one of his blogs or podcasts or newsletters, and it showed him running one morning. I think he runs every morning or something, five or six miles, maybe more. And to me, running is painful. I hate running.

JIM O'ROURKE [01:12:44]: It's like watching paint dry. It goes so slow. And he was saying it too. He's huffing and puffing, and I thought he was gonna stop. And they, he did an interview after, and, like, I thought he was gonna say you loved it. And he's like, I hate running, and I do it because it's my hard. Like, this is hard to me. And that really stuck with me, and I thought I'd kick back to hike.

JIM O'ROURKE [01:13:05]: I love it. Out here in Arizona, we got some ridiculously complex mountains to hike. And when I'm hiking the mountain, I'm thinking there's no way building a sales company is this hard. There's no way building a sales company is this hard. And hiking sucks. It's painful going up the mountain and, you know, and I'm always about time and measurement, so I'm trying to do it as fast as I can. And, but it gets me away from the grind. It really rejuvenates my mind. I listened to a great podcast last night. As an example, I walked five miles just around my dark neighborhood, and I listened to, like, clips of, the Rockefeller story. It was 55 minutes. I walked four and a half miles, and in that 55 minutes, I felt like I learned a ton. I disengaged from the day to day.

JIM O'ROURKE [01:14:01]: I listened to holy crap. Like, that's what Rockefeller did. And so things I heard, focused, not tied to my email, not looking at my phone. That was pretty cool, and that works. And I can't lie. Like, having a few cocktails, IPAs, happy hours out here have really grown on my wife and I where just three o'clock, all of our East Coast business is kinda slowing down, Midwest kinda slows down, and so three o'clock is, like, some ways the end of a workday here. So, you know, you get on the golf cart and go get a couple beers and grab some bites, and that is rejuvenating as well.

TIM REGAN-PORTER [01:14:42]: As a leader, how do you think about making sure your team is taking care of themselves?

JIM O'ROURKE [01:14:49]: There's a real competitive spirit in the company with a big group of us. I'll clip my mountain results from Sunday and send it to, you know, Emerson, who's out in Colorado now, the old the guy that bought the Vermont business from. Hey. What do you think of this? And that leads to a text exchange back and forth. I know Caleb, our COO, always has been into, like, a magnificent, you know, body and transformation and training and things like that, and it's just fun. It's fun sharing things and not just having it be all about business. I think there's a lot of there's a lot of trusted friendships and things that are constantly on the bill, you know, when you're running a company and working closely together. I try my hardest not to—I know I pressure hard, too hard sometimes for results, but I also try to make sure people know at the end of the day that when times are tough, we're gonna hunker down and figure it out and work together on it.

JIM O'ROURKE [01:15:50]: And I tried very intentionally not to behave—the hedge fund and the private equity world I was in where I was one of the ones always firing people when results weren't what they were supposed to be. And I was always looking over my back, you know, on any given month. One you're one bad quarter away from getting fired, I thought, for many, many, many years. And I try to really make sure people don't feel that. That doesn't mean you don't have to drive change and make tough cuts because you, unfortunately, you do. But generally speaking like, we've had a really good retention rate as a company, and that's a really good, that's a really big win behind the scenes when you do what we do.

TIM REGAN-PORTER [01:16:33]: Do you have any favorite time saving hacks?

JIM O'ROURKE [01:16:37]: My, a time saving hack that I wish I could instill in most I do it myself, but trying to clear your inbox at the end of every day, trying to sort your emails into folders, you've just got to be kidding me in this state. So I have 28,000 emails in my business email right now, and, when I pull my personal Gmail in, that's—let me see. This is a funny—88,000 emails, and I don't give a crap about sorting my emails. When I get something, I deal with it, or I have a way to code it and go back to it. Everything else is just gonna go, and every couple years, I'll go and delete everything and not miss a beat. So I work with people that sort everything. Like, oh, it's from Jim. It's going in this folder.So it is no. It's not me. I don't want any part of it. I don't wanna figure it out. So I view that as a time saving hack, and it's a strong recommendation I have with people around me.

TIM REGAN-PORTER [01:17:41]: I would second that. Merlin Mann was a productivity guru of sorts 10 years ago, maybe longer, was very popular, but he gave us, he gave a talk to actually Google about Inbox Zero, and that was one of his first tips. It's like, don't be precious about this thing. The search works really well. Like, just archive it. Move on.

JIM O'ROURKE [01:18:03]: Yeah. And if you're engaged, like, you remember where things are. It's like having the messy desk. You knew where something was. And now, though, the problem is you get so many stupid emails in a day. They're so trying to sort that, I'm sure there's a way to have all the nonsense go into a folder, create a label, do all that. We have people to do that brilliantly, but I don't, it's not me. And to me, it's a big waste of time. I want a reward for growing cash flow, revenue, audience, print subscriptions. You don't get any award for having a clean mailbox at five o'clock every day, email box at five o'clock every day. You should actually get penalized for it in my opinion.

TIM REGAN-PORTER [01:18:44]: Five years out, what does success look like for OMG?

JIM O'ROURKE [01:18:48]: Five years, I'll go a little bit off the ranch here with a comment. I'd love to be—five years, with the right with the right capital investment from an outsider—I haven't figured this out yet—it could be PE and I could…. You know, there is some good PE out there, by the way, that are, they know how to get money, and it's the only thing holding us back right now. Getting more people in that can sell advertising and capital to open this up. So I'm always on the hunt for the right patient behind the scenes investor that doesn't wanna try to tell us or tell me what to do. Just you're gonna get a great return, sit back, and enjoy it because, and then help us when we need money, help us when we need whatever other things some an outsider could do. I don't claim to have all the answers, so there might be some business advice here that I'd always be receptive to.

JIM O'ROURKE [01:19:40]: But I think five years from now, I'd like to be a $100 million company. And, candidly, like, what really intrigues me behind the scenes, and I've started to do some work on this, is to switch this over to an ESOP owned company. And I think that to me will be, that's the goal because I think it could be really impactful. I think how we run the culture within our company, it really drives a sense of engagement that if we keep having success and we're able to grow the business, I would like nothing more than for people making that happen to be rewarded in ways that they won't be on the regular course, their own financially. And so that can work. It's gotta be the right finance partner. It's gotta be the right timing. It's, they're all, the stars have to align to make that worth it.

JIM O'ROURKE [01:20:33]: But from my understanding of it and my studying of it and working with I've had I have some folks I'm working with on this right now. I have a pretty good feel for it could be a good path forward, largely because I wanna keep the company going. I don't wanna build it up and sell it, you know? So I think the ESOP has all the checkbox type things that could make this really, really interesting moving forward. The opportunity is gonna be there to continue to grow and add markets so that there's no doubt about that.

TIM REGAN-PORTER [01:21:07]: And if you haven't looked into it, our governor in Colorado is a big fan of ESOP, so they've got some pretty strong incentives here.

JIM O'ROURKE [01:21:14]: There's huge incentives in Colorado to encourage ESOPs, and the firm that I was working with in New York on this so far mentioned that to me, the last time we met. They're like because, you know, we bought a few businesses out there, and they're like, woah. They knew. They were all over that, and it's really good incentives for a business to expand in that space, and I love Colorado. I think there's a lot of expansion opportunity for what we do in Colorado. Some, in some markets, it could be starting new or going into a market that's not being served the right way now. I'll keep that quiet, but I have a real specific town in place where I know what we do could work with the right investment. And I think there's a lot of family owners that are gonna look to exit over the next 3, 5, 10 years. And I think it's a great state. I like it because it's close to me here. So I love Arizona, Colorado, New Mexico these days, and so, hopefully, we'll get a chance to figure that out.

Media and local recommendations

TIM REGAN-PORTER [01:22:14]: And the final two questions are recommendations. So in terms of local activities and places, what would you recommend there?

JIM O'ROURKE [01:22:24]: I—and I see this all the time on the mountains around here, tourists and people coming into town. Hiking is definitely one. I've had spurts of golf with my son this past holiday season. If you're into golf, I mean, this is the golf, one of the golf meccas in the country, I think. You really have a lot of fun with that out here. Just like most bigger cities, there's just a fantastic lineup of restaurants and places to go eat. The whole outdoor thing out here is just this time of the year, especially, it's just awesome, with the weather, and it's sunny every day out here. So, yeah, any activities I push have to include the outdoors, especially moving from Philly, Vermont, Minnesota, or Michigan, Chicago. We're in heaven out here. It's 89 degrees now, and it just feels spectacular outside.

TIM REGAN-PORTER [01:23:22]: And then final question, three to five pieces of media, and these can be entertainment or news related, books, podcasts, movies, whatever.

JIM O'ROURKE [01:23:31]: I think TikTok's brilliant. I don't worry about China tracking me when I'm on TikTok. I think it's entertainment, but I also find that following the right news feeds on TikTok, as long as long as you have a filter for fake stuff. But, I mean, if you like David Muir updates from World News Tonight, you get it in 30 second clips on TikTok at 10 o'clock at night, and it's the most relevant stuff going on. I love it. If I'm home and not traveling, Good Morning America is a fixture in my routine, 7:00 a.m., probably just to 7:15, 7:20, enough for a cup of coffee and just to think clearly in the morning outdoors. I love to agree to disagree with George Stephanopoulos and the spin put on certain things.

JIM O'ROURKE [01:24:25]: But, generally, like, you know, Good Morning America is a good news source to keep in tune to everything going on in the world. So I really have a lot of respect for the reporting they do and they make it intriguing. I mean, I literally can't wait to watch that every single day. I love New York Times on my app, on my phone, just reading in between whatever I'm doing. That's a big part of things. And from a learning perspective, the LinkedIn platform is powerful. It's probably where I do most of my learning today. Just yesterday, like, whatever that, the Rockefeller podcast I mentioned, I think it's called Founders podcast or something.

JIM O'ROURKE [01:25:11]: Some guy, you know, transcribes books, and I love that because I don't have time to read books. I love Bill Gates and all those guys when they recommend all these books to read. I don't have time to read three or 400 page books every day and every week. And so when somebody gives me a 55 minute description of a huge book where I can learn some stuff, I love that. And I don't find, I wouldn't have found that if somebody posted it on LinkedIn, and the Rockefeller thing caught my attention. Like, here's the 30 things Rockefeller said in this book. Then I came across this Founders thing. I'm like, oh, shit.

JIM O'ROURKE [01:25:46]: Like and then there's dozens and dozens and dozens of podcasts on here. I can't wait to listen to the one about Sam Zell tonight when I walk. So, again, the root of the positive there is LinkedIn, and the way people share information on there in a learning kind of a way. I love it. So that probably would, that's probably it. There's a lot of other stuff, but, this your podcast, E&P, Borrell, I stay in tune to all that stuff. I love following what peer companies are doing. So when people go and tell their story, that's a great way of learning for me.

JIM O'ROURKE [01:26:24]: I don't agree with it all. I don't even agree with all the entities I just listed. You know, some things I just like, what? Are you kidding me? Like, what? You really but most of the time, it's intriguing and it's a learning experience. And again, it's something that you can do when you're walking or driving or, you know, maximizing time is probably what it's all about these days with everything going on.

TIM REGAN-PORTER [01:26:47]: Well, thank you for your time, Jim. This has been great.

JIM O'ROURKE [01:26:49]: Yeah. Thank you, Tim. Thanks for having me.

TIM REGAN-PORTER [01:26:54]: Thank you for listening to the Local News Matters podcast. Never miss an episode by subscribing in your favorite podcast player and sign up for our newsletter at lnmpod.com.

And thanks to our production partners at Pirate Audio. Pirate Audio believes every community deserves great things to listen to, and they're on a mission to help local newsrooms reach their communities via audio. If you're interested in starting a podcast or need production support for an existing one, let me know, and I'll be happy to connect you.

If you have guest recommendations, others doing interesting and innovative work in local news, let me know through the contact form at the website, lnmpod.com.

Past guests on the Local News Matters podcast include: Teri Finneman, Nick Mathews and Pat Ferrucci (Reviving Local News), Nic Dawes (THE CITY), Allison Taylor Levine (Local News Initiative Delaware), Crystal Good (Black by God), Lisa Snowden (Baltimore Beat), Karen Rundlet (INN), Jim Brady (Knight Foundation), Candice Fortman (Exit interview, Outlier Media), Jean Friedman-Rudovsky (Resolve Philly), Jay Rosen (NYU), Sue Cross (Exit interview, INN), Mary Margaret White (Mississippi Today), Amy Kovac-Ashley (Tiny News Collective), Michael Shapiro (TAPinto), Kenny Katzgrau (redbankgreen and Broadstreet), John Garrett (Community Impact), Shannon Kinney (Dream Local Digital), Larry Ryckman (The Colorado Sun), Frank Mungeam (Local Media Association), Kelly Ann Scott (Alabama Media Group), Sara Lomax and S. Mitra Kalita (URL Media), Elizabeth Hansen Shapiro (National Trust for Local News), Mike Rispoli and Richard Young (via When the People Decide), Sarabeth Berman (American Journalism Project), Rabbi Hillel Goldberg and Shana Goldberg (Intermountain Jewish News), Lyndsay C. Green (via The Journalism Salute), Rashad Mahmood and Mark Glaser (New Mexico Local News Fund), Christian Vanek and Barbara Hardt (The Mountain-Ear), Dan Grech (BizHack), Zack Richner (Easy Tax Credits), Tracie Powell (Pivot Fund), Dan Oshinsky (Inbox Collective), Linda Shapley (via What Works), Yehong Zhu and Jake Seaton (Zette, Column), Charity Huff (January Spring), Joaquin Alvarado and Dave Perry (Aurora Sentinel), Steve Waldman (Rebuild Local News), Maritza Félix (Conecta Arizona), Michael Bolden (American Press Institute), Jeff Roberts and Corey Hutchins (CFOIC, Colorado College), Eve Pearlman and Erica Anderson (Spaceship Media), Jennifer Brandel (Hearken, Democracy SOS), Corey Hutchins with Bay Edwards, Todd Chamberlain and Raleigh Burleigh (Sopris Sun).