Kaufman said while the technology involved in creating this podcast is far different than what he used for the audio journalism he did in college 30 years ago, many of the principles remain the same.
“The move from analog to digital was pretty big. I mentioned the reel-to-reel tape. I learned to edit audio by cutting the tape with a razor blade and then splicing it together again with Scotch tape. I used to look at my great-grandfather and think ‘Wow, he was walking around Manhattan before there were cars,’ and now I’m that guy. I edited with Scotch tape, children!”
“It’s kind of the same thing coming out of the headphones, though. To the listener, if you go back and listen to an ‘All Things Considered’ story from 1980, it would sound a lot like ‘All Things Considered’ today, or lots of narrative podcasts. It’s not like watching silent movies or something. So I had to learn some new tools, and mostly it’s just that a lot of things are way easier, but the basic idea of tell a story, don’t lose the listener — that hasn’t changed.”
Shifting from mostly working in written formats to audio documentaries may seem like a big change from the outside, but Kaufman said there’s a lot of overlap between the different areas of journalism, and it’s been useful for him to have experience in those different formats.
“I think of all my journalism experience as one thing, not as separate tracks. One of the best things I ever did as a writer was work in radio when I was young. That taught me a lot about language, how people talk versus how we write. My writing style is conversational, and radio is why. So whenever I go from one medium to another, it’s not like I’m new. I bring what I’ve learned.”
“When I was a book editor, I was a book editor who’d come from newspapers and websites. And I learned some things as a book editor that I brought back. Doing the SiriusXM talk show taught me about speaking with a certain energy level that feels a little unnatural to me as a person, but I think works on the air, at least for me.”
What’s the business model for “Can’t Win 4 Losing”? Well, Kaufman created it with his own money, but has partnered with San Francisco podcasting network VSporto for distribution, promotion and advertising. He said connections from his SiriusXM days helped there.
“Aron Glatzer, the VP of content, was in charge of putting together Bleacher Report’s SiriusXM Channel in 2014, and he offered me a show. We stayed in touch when he went to VSporto. I mean, we’re friends. He introduced me to Keith Jasper, the CEO and founder, and we talked now and then over the last couple years about me doing a podcast with them when I was able to do one. So they obviously were the first people I talked to when I started working on CW4L. They weren’t the only ones I talked to, but they were the best fit. …I make the show, they host it, distribute it, promote it and sell advertising. They’re the ones who know the business.”
Kaufman’s already put a lot into the show, though, and not just in terms of time. Some of his episodes involve in-person reporting trips, which aren’t easy for even bigger news organizations to fund these days. Kaufman said he was able to make those costs work by careful planning, though, including using the same trip to report multiple stories and saving money wherever possible while traveling.
“It’s not insignificant but it’s also not overwhelming. You’d be surprised how cheaply a person can travel when he’s alone, able to fly at any hour, can stuff everything he needs into a carryon and can sleep on couches or in shared AirBnB’s.”
“I made a couple of reporting trips for this season — [one was to New York, while] the other was to Texas and Louisiana — and on both of them I was able to report multiple stories. On the New York trip, I reported three stories and went to the SABR convention, which was a good networking opportunity for me. The Texas-Louisiana trip was also for three stories. I was hoping it would be four but one didn’t work out.”
“So yes, it costs money, and yes, I have a budget. My venture capital was my severance pay from Turner, which laid me off from Bleacher Report in February, plus my unemployment insurance, some savings and 0-percent credit cards. I tried to be as economical as possible, but I didn’t set out to do the podcast for the absolute minimum. Yes, some of the people I interviewed in person in Texas I could have interviewed on the phone. It wouldn’t have been as good. On the other hand, it would have been better if I had more and better microphones. I just tried to find the right balance where I’d get the most bang for my buck.”
“It costs money to do this. Even 0-percent credit cards come due at some point. I had to guess at my budget because I don’t know how much money I’ll make with Season 1. I might not make any. Whether there’s a Season 2 will pretty much be a financial decision because I definitely want to do it.”
While “Can’t Win 4 Losing” covers wildly different subjects, from fictional poems to real hockey teams and racehorses, Kaufman said the bigger hurdle in creating it is ensuring that similar subjects don’t overlap.
“It’s not tough to tell different stories in a given framework. The challenge, I think, will be: Now that I’ve told the story of this really bad Washington Capitals team, how do I tell stories about other really bad teams, like the winless Detroit Lions or something, without repeating myself? Or how do I avoid each story type becoming a formula: Here’s the really bad team story. Here’s the heartbreaking last-second defeat story. Here’s the one millimeter from greatness story. Repeat with different names.”
“The answer is: I don’t know. We’ll see!”
He said the largest hurdles of all are convincing subjects to talk to a one-man podcast, then condensing all the good material he does get.
“I’m finding that the biggest challenge on most of the stories I’ve done so far is access, finding the people I want to talk to, getting ahold of them in the first place, convincing them to talk to me. And beyond that the biggest challenge is actually writing the story, because I usually have so much good stuff that it’s hard to cut it down, figure out what to take out and what to leave in. It’s a constant struggle of shoving 50 pounds of mud into a five-pound sack, as Dolly Parton says.”
“Because of all that extra stuff, I’m going to do some midweek bonus episodes. I often only use a few seconds’ worth of sound from a really interesting, longer interview. So bonus episodes will have those longer interviews, plus some fun, interesting stuff that didn’t make it into the main story. There won’t be one every week, but there will be one for the first episode, about Casey at the Bat.”
Kaufman said he’s also trying to strike a balance between providing deeper background and perspective on well-known stories, like “Casey at the Bat,” and telling lesser-known stories like that of losing racehorse Zippy Chippy. But he isn’t planning to do the too-obvious stories.
“I think both of those scenarios are pretty good. For me as a listener, I’m intrigued by both types of stories. ‘Oh, I’ve heard of that … but what’s the deal with it?’ and ‘I had no idea about that.'”
“I will say I shied away from the stories that people really do know. As I told people I was working on a podcast about losing, they’d say “Well you’ve gotta do Bill Buckner.” But everyone saying that tells me the subject’s covered. I feel like we know about Bill Buckner. Let’s find another story.”
“That said, if Buckner called and wanted to talk, I’d probably do something!”
The 12 episodes of Season 1 are going to be released weekly on Mondays. Kaufman said he’s hopeful he’ll be able to do a second season, but it depends on how this one goes over.
“What will determine Season 2 is the response to Season 1. If we find an audience and are able to make enough money for me to continue doing the show, I’ll definitely do it. There are a lot more stories to tell, and I feel like I’m just figuring out how to do it. …If this sounds interesting to you, or if you’ve ever liked anything I’ve ever done in my career, then please subscribe!”
Thanks to King for his time. You can check out Can’t Win For Losing on its website (complete with show notes), or through feeds from VSporto, Stitcher or Apple Podcasts. You can also follow him on Twitter, and check out a Medium piece he wrote about the show here.