Readers (originally listeners, hear this as a podcast here, this article is the transcript of that episode, so excuse typos and the like as it is, you know, a transcript), I want to admit to you something I first told a crowded hall full of people at Podcast Movement’s Evolutions conference in LA a few weeks ago. I was there speaking with a few friends as part of the Indie Panel and we stuck out, not just because at a conference where most of the speakers were professionals for the big networks, we were not. And not because in an industry dominated by white men, I was the only white guy on the panel. No, we really stuck out for our vulnerability mostly because I was one of the few speakers there to admit that I, Jay Shifman, founder of Choose Your Struggle, have failed miserably.
Now, real quick, I do want to acknowledge that while my general self-loathing, anxiety, and OCD want me to think I am in total an absolute and complete failure, I am not. I am a loving husband, son, brother, uncle, grandson, nephew, cousin, friend, board member, a member of the greater Philadelphia community, pet roommate to my girl Nell, and company founder. I speak my mind and use my voice for positive change and in that way I am a successful advocate. I also work tirelessly, and this is something I am so damn proud of, to amplify the voices of those y’all need to be listening to besides me. Because while there are aspects of my story that aren’t heard enough, generally, as a white male of relative means, y’all hear from people like me plenty. All of this to say, however, that I am not in total a complete failure. I appreciate my wife reminding me of this whenever the little voice in my head has convinced me otherwise and I start spouting out toxic sewage from my downturned mouth, usually while curled in a ball in our bed. So, Lauren, you are right. I am not a complete failure.
However, recently, I have failed, and I’ve done so massively. Let me explain. I started Choose Your Struggle, the company and my brand, back in 2015. I came out of telling my story on stage for the first time like I was launched out of a cannon. And I sincerely felt that way. When you’ve been walking around for half a decade with the weight of stigma on your shoulders and suddenly it’s gone, I honestly felt like I could fly. And the community responded. I was asked to speak often. People reached out to chat and asked me to advise their family members and, in a few instances, themselves. I was wanted. I was loved. All for simply being me.
This continued and it was a few years later that I decided to take this work full time, in 2019. I didn’t have much of a business plan but I set about trying to create a successful business all the same. I knew public speaking would be my bread and butter. I thought I’d continue to do some coaching, so I got a certificate to coach. I thought I’d go back to my old love of writing, which I’d previously failed at, so I started applying for writing gigs. And for a while even though I wasn’t making money, I could see the promised land of profits from this work.
To be clear, profit was never my motivation. I wanted it, I knew eventually I needed it, but it wasn’t what got me out of bed each day. Helping people was. Ending stigma was. Telling my story was. This is what mattered to me. So I spoke all over. For free. Every week was somewhere new. I treated it like a comedian, going to endless crappy open mics, just getting my feet under me, doing what I loved. And by the end of 2019, I was actually being paid occasionally. I’d made it out of the ‘always free’ category of speakers to the gray area between free and paid. I could see the light. I was almost there. I even landed a recurring role, speaking to new recruits of police about what it was like being a drug user. Yeah, I know. I let my desire for a paycheck overwhelm my common sense on that one. Which I regret. After the 2nd gig I said never again.
Then we all learned a new phrase, Coronavirus. Remember that? Our country’s “leadership” recently decided it was gone. So there’s that. But back in 2020, we shut down. We did the right thing for a while. It was too late, we know that now and we knew that back then too, but at least we tried. And my dream of not only breaking even but making a profit died when we did. In the 48 hours after the NBA paused their season, the moment we all recognize now as when we knew this whole covid thing was for real for real, I lost five paid gigs. And now, two years later, I’ve yet to make up more than two of them.
Luckily for me, I’d started a podcast a few months before. The Choose Your Struggle podcast was born out of suggestions from my good friend and fellow podcast host Spark Tabor (Check his show Cookies For Breakfast out here!) and a prior coaching client, and my own recognition in January of 2020 that this covid thing was probably going to be a big deal. So when the country shut down, I doubled down my efforts and treated the show like a full time job. And it paid off. It quickly grew to the point that at the end of its second season, it was in the top 5,000 English language podcasts in the world. Which still sounds unreal to me. Like, I DID that. I made that HAPPEN. I forced some people to pay attention to their own incorrect “knowledge” on mental health, substance misuse & recovery, and drug use & policy, and how they contributed to stigma. I DID THAT SHIT.
In that time I started working on some other projects, growing the business to include other outlets aimed at the same twin pilers of ending stigma and promoting fact-based education. These included Rock Bottom Storytellers and a Day in the Life, which are the virtual storytelling events that broadcast on LinkedIn, Facebook, Youtube, Twitch, and Twitter. A book I’m co-authoring with the fabulous journalist M.L. Lanzillotta. And, my baby, a new podcast called Choose Your Struggle presents Made It, Season 1, Stay Savage which will drop April 29th.
Here’s where we get to the failure. Because of the whole covid thing, I was ok with my business not making a lick of money in 2020 and 2021. I even hired people during 2021 to help position me so that when things started opening back up, I’d be in a good spot to speak again. Well, I didn’t factor in something important. With so many opportunities disappearing to the virus, the remaining ones could be way more selective. So sure, there’s some spots for me to speak but, like at that recent podcast conference, the only people getting paid were the big names and the people at my level were getting free tickets and a chance to promote our shit. Which, well, ask a bank if you can pay your mortgage on exposure. Maybe yours can. I dunno.
So those people hired, all three of them, one after another, failed to find any paying gigs. It wasn’t for lack of trying, I can tell you that. None of them were exceptional hustlers; none are going to be teaching seminars on sales, but two of the three busted their asses for me. At least in spurts. So I have to tip my hat to that. But the business model I built for 2023 and beyond took a major hit with their failure. Really our failure. Because I was their boss. So the buck stops with me, as the saying goes.
But I made an even worse bet, which, in hindsight, means I can’t really be mad at them for their inability to drum up any business for me. Does that failure suck? Yes. But what I did was worse.
See, the Choose Your Struggle podcast has opened some doors for me. I don’t really do the whole sponsorship thing with that show. I mean I have some affiliates (see the show notes for Road Runner CBD and bookshop links) but I like my show the way I like it so I don’t want to futz around with sponsors who will want changes or control of some kind. BUT, with Made It, I budgeted in some pretty substantial sponsorship money. If that’s confusing, I get it, so let me explain.
By the time this drops, I will have spent over nine months working on this story. Closer to ten. And traditionally, serial podcasts do really well. Plus, this is going to tell a truly exceptional story. And I had exposure from my main show. If you were creating a recipe for financial success in independent podcasting, this is it! This is literally all the things they teach you at conferences like the one I just attended. But I forgot about a key factor: brand safety. And this, my friends, is the key failure.
See, I pitched over twenty-five sponsors for Made It. It should have been more, but I those twenty-five gave me enough of a glimpse that I could see the writing on the wall. A good case study, if you will. Now, a little less than half never responded, which is actually a pretty good rate. Kind of disappointing? Yes but just the reality of the situation. Anyway, of those just over half that did get back to me, only two said no because of money. Which is BAD. Because if the responses were all no’s over budget, you can fix that. Lower your rates, pitch bigger companies etc. But when over ten people come back with nos over the dreaded content, or brand safety, and you’ve done a good, or at least good enough job, of pitching different directions, you can’t fix that. Given the choice between sponsors and telling the story the way I want to, I mean, y’all know me. It’s the story. Every time. So that was that. No sponsors were coming to throw relatively low dollars at me for making this show.
So this is where we find ourselves. Season 3 of the Choose Your Struggle podcast is here. Made It will drop in a few weeks. And after that? I don’t know. Due to these financial failures, I had to let my team go. Well, the one member of my team I was paying regularly. Yep, my producer and assistant Ryan is no longer with Choose Your Struggle. I let him know I had to cut his hours and he did what I would have done at his age a decade ago and told me peace out. To be clear, I don’t blame him. He can find more steady employment somewhere else for sure. So, Ryan, if you’re reading this, no hard feelings.
And now, the question remains: where do I go from here? Well, Season 3 will go on as scheduled. It won’t be as smooth without a producer. But that’s ok. All your love and support means I wouldn’t even think of stopping it, at least without a good reason. And after Stay Savage, I know Made It, Season 2 will happen… sometime. But beyond that, it’s clear to me that it’s time for Choose Your Struggle as my full time thing to end. Which is sad for me, but I certainly gave it my all, and no one will ever be able to say I should have worked harder, so I can’t be sad about that.
And there’s a few irons in the fire right now that may mean I look back on this in a couple months and laugh. A speed bump more than a giant pothole that broke the damn fender off my car or… I lost the analogy but you get the point. And there’s always the chance that Made It Season 1 drops and it goes buck wild, serial 2.0 style, and of course all my wildest dreams come true and I ride off into the twin sunsets of Tatooine on a unicorn. But I’m not holding my breath.
More likely scenario? This summer finds me taking work for someone else on a part time on contract basis that allows me to continue my work but still pay my mortgage and keep my pup nell in dog food and pretty bandanas while I figure out a new path forward. But I don’t know. We’ll see. Actually, I’d love to hear from you here. Do you have ideas? Are you a business that always thought about producing a podcast but don’t know where to start? Are you someone who wants to sponsor this work, or at least learn more about how to support? Do you need someone to write, or speak, about drug use, substance misuse, or drug policy? Reach out. Email me at Info@Jayshifman.com. Or leave me a message through Podinbox at Podinbox.com/cys.
In the meantime, get excited for Season 3! The first official episode will drop a week from today, Friday the 15th. And Made It, Season 1: Stay Savage, which will drop on April 29th.
But as always, be vulnerable, show your empathy, spread love, and choose your struggle.
