10 Things I Wish I Knew Before Starting a Podcast

A noticeably chubbier me and Marc Maron, or as Uncle Frank commented, “Fantastic! Looking a little chunky there”.

Back in 2016, when I told people I was starting the Cityslickers Podcast, they looked at me like I was speaking Aramaic. Podcasts weren’t what they are now, and for a rapper like me, diving into this new world was uncharted territory. I started this whole thing from the same place as my love for rap — the idea of capturing stories, leaving behind a footprint, and creating something real on some borderline obsessive shit. You know you’ve tapped into something real when it feels like you’re putting yourself on blast, but in the end, it’s a good feeling because it’s authentic. Listening to Marc Maron’s WTF podcast got me hooked on the format. I loved hearing people’s raw stories and how Maron was able to bring that out, to the point where it didn’t even feel like an interview; he was able to capture someone’s essence. In effect, it was like creating a time capsule of a human experience.

What I didn’t realize was how hard it would be to take that idea and turn it into something consistent, especially while juggling a music career. What I didn’t know back then, and what my future self would’ve told 2016 me, is that passion alone doesn’t keep the wheels turning. Without proper planning, multitasking, and patience, even the best ideas can become stressful and go unfulfilled if you don’t nurture them. You can’t just rely on having a vision — you need to grind through the muck; things get nasty, but pressure makes diamonds.

Here’s what my future self would’ve told 2016 me before hitting record.

1. Commit to Your Vision — Even When No One Understands

When I first started Cityslickers, explaining that I was launching a New York lifestyle podcast was like telling people I was trying to contact aliens. Podcasts were still in that weird space where people didn’t get it unless they were NPR fanatics or comedy nerds. My rap manager even said, “You gotta figure out if you want to be the greatest rapper or the greatest podcaster.” He was one of the few people to see how much time and effort went into the process. I’ll never forget him saying that because it made me question myself. Sometimes, I’d sit surrounded by recording equipment, wires everywhere, asking myself what the fuck I was doing.

It wasn’t just about me; I was delving into something unfamiliar to everyone. I knew that no one in my industry was doing this in 2016. Now, I don’t need to explain it — everyone has a podcast or knows someone who does. My future self would tell 2016 me to trust the vision, no matter how many people were confused by it. The same can be said for any idea you may have.

2. Love the Process, Not Just the Outcome

Podcasting in 2016 wasn’t the industry it is today, so I didn’t go into it expecting instant fame. But even then, I wasn’t fully prepared for how much work I’d put in without immediate rewards. I had friends and family who didn’t even listen to the show because knowing me made them nervous, like they didn’t want to see me fuck up in public. The people who did listen said it was a little long-winded (which it probably was). There were countless times I sat in the studio or packed up my gear and thought, “What the hell am I doing?” My rap career was already a full-time hustle, and here I was, sinking hours into a podcast that felt like no one was listening to.

If I could give my past self advice, it’d be to remember that the process itself is the reward. You’ve got to love it for what it is — not for the numbers it brings. My future self would remind 2016 me that it’s about documenting the process, even if it feels like a waste of time at the moment. Sometimes, you’re ahead of the curve without even knowing it. The world will catch up — keep going.

3. Consistency Is Harder Than You Think

I went into this project thinking I’d drop new episodes every other week like clockwork. But life happens in the era of ADHD. Guests cancel, technical issues pop up, and trying to stay consistent while keeping up with my music career and life’s happenings was intense. Two weeks turn into a month, and you’ve lost all momentum before you know it. You have to do this on days when you don’t feel like doing anything at all. It has to become a second job.

My future self would’ve told me to record a few episodes ahead of time and not try to keep up with a weekly schedule unless I had the material ready. The grind is real, and without consistency, your audience will fall off before you even have a chance to build it.

4. Plan Ahead — Interviewing Is an Art

As I previously touched on, I went into podcasting thinking I could sit down, hit record, and let the conversation flow, just like Maron. I realized very early on that riffing without structure doesn’t always make for compelling listening; it just complicates the editing process unnecessarily. I learned that lesson the hard way during my first episode when I asked a guest if they had food allergies. Seriously, why?

I thought spontaneity would improve conversations, but that only works when you’re a pro at steering a conversation. I was scrambling for topics on the fly, resulting in many awkward silences or irrelevant questions. There’s a reason why shows like WTF work — Maron might riff, but he always has a direction.

Not only did I need to research my guests, but I also had to look up as many interviews and conversations with the artist as I could find to ask questions that haven’t been asked before. I noticed, especially through being an artist myself, interviewers ask the same questions, some even knowing those answers already exist. For example, expository dumps don’t have to be asked in question form directly; they can be handled in pre-recorded introductions. Questions like, “So how did so-and-so come about?” have likely been answered a thousand times over if the person is a public figure.

My future self would tell 2016 me to embrace the prep work. You can’t just wing it every time. Michael Jordan had to get the fundamentals down before adding his own flair — that finished product that crushed my dreams every year as a Knicks fan. Go in with at least a loose game plan, some key questions, and a structure to fall back on. Once you have your process down to a science, you can get a little looser with your tracking process.

5. Let Segments Evolve Naturally

But you also have to let segments come to you, or else they just come off as forced. Forcing segments not only feels inauthentic but can also alienate your listeners. Let the previous podcasts and feedback dictate what you want to emphasize in future episodes, and let segments create themselves.

For example, we had a segment that sprung out of a conversation about New York $20 dates that could have been expanded on. It resonated naturally with our audience. On the other hand, one that we planned out was “4-Point Play,” a Knicks-exclusive segment that was too niche and probably polarized listeners. Everyone listening had an interest in New York but not necessarily in the Knicks or even basketball for that matter.

My future self would tell 2016 me to be patient and let the podcast evolve organically. The best parts of the show often emerged from genuine conversations and recurring themes that resonated with the audience. Pay attention to what works and let that guide the development of your podcast’s unique personality.

6. Guests Will Flake — Always Have a Backup

Back when I was deep in the New York rap scene, I built up a crazy network of contacts. I thought that would make getting podcast guests a breeze. But I was wrong. The Greenpoint studio was too far out for most people, and securing guests felt like pulling teeth. I remember scrambling at the last minute when a guest canceled, leaving me and my co-hosts with no one to record.

I quickly learned the importance of having a backup plan. If I could go back, I’d tell myself to pre-record episodes or even just segments to avoid scrambling for content each week. These backups could fill in when a guest couldn’t make it. Additionally, doing more guerrilla-style recording on the go would have been beneficial. Now, with AI, recording on the fly while ensuring professional quality is fully possible.

7. Don’t Burn Your Best Guests Early

Peter Rosenberg was one of my most prominent early guests, and I fumbled the opportunity by spending too much time talking about the Knicks. While it was fun at the moment, the episode didn’t age well. Sports conversations date quickly, and I didn’t make the most of having someone like Rosenberg on.

Ideally, you want to establish good chemistry and know what you’re doing before roping in big guests, especially those who may be available to you. You should have a solid structure down. Starting with guests you know on a more personal level makes more sense — it serves as practice in a way. Then, slowly start bringing in names who may be less of a personal connection and might be on a tighter schedule.

Establish who you are first, instead of relying on big names to attract listeners. Otherwise, people might not be checking for you, but only for your guests. I see this a lot on many clickbait-driven podcasts today.

My future self would tell past me to plan more timeless conversations with big-name guests — something that can stay relevant long after it’s been recorded. Don’t squander big opportunities by being unprepared or focusing on fleeting topics.

8. Bad Audio Will Ruin Everything

It doesn’t matter how great the conversation is — if your audio sounds like it was recorded inside a blender, no one’s sticking around. I learned this lesson the hard way during an unreleased episode with Nick Catchdubs of Fool’s Gold Records. We recorded in an empty conference room, and the acoustics made it so the audio quality sounded like we were in a toilet bowl. I never released the episode because of it. I felt upset, like I wasted my guest’s and my own time.

After that, I realized I had to prepare for these things — for example, ensuring that multiple sources were recording, which could even be an iPhone microphone, and then syncing everything up in post.

If I could return, I’d tell myself to invest in decent equipment and always check the setup before hitting record. A good podcast lives or dies by its sound quality. Always double-check your gear, run sound checks, and don’t cut corners on audio quality.

9. Editing Is a Beast — Prepare Accordingly

The easiest part of the podcast is talking. Beyond tracking, editing it down to something entertaining was brutal. I was used to mixing and tracking for my rap group, but podcasting was a different type of monster — multiple inputs, multiple voices, and hours of conversation that needed to be boiled down to something usable.

Firstly, you have to make sure the mics aren’t peaking, which is a way less stressful process in our era of 32-bit float WAV files, but back then, you had to meticulously check your recording setup — which I won’t get into here, but you can learn all about on YouTube University for free. You want it to feel natural and flowing while removing the awkward pauses and tangents, making it all sound cohesive for the audience.

Staying on track is imperative; it’s why you see many celebrities with podcasts (The Roommates with Josh Hart & Jalen Brunson, Hotboxin’ with Mike Tyson) have a co-host who keeps things flowing. When you keep rhythm in mind, veering off-course becomes the icing on the cake that gives your production personality. But just sprinkle it in — don’t keep driving down the wrong road. It just makes the editing process a living hell.

Editing is a true test of patience, and my future self would’ve told past me to pace myself and accept that this would take much more time than expected. Having that spine tying everything together is crucial for both creating an engaging conversation and streamlining post-production.

I also must mention that, during this time, AI was very barebones — even software like Izotope was still in its rudimentary phase. In this modern era, I would fully implement AI for all it’s worth, to cheaply and quickly get a podcast to a professional production level.

10. Embrace Feedback and Adapt

Early on, I was so focused on my vision that I didn’t pay enough attention to listener feedback. The most common takeaway I would get was that the episodes were too long, among other things. Considering all the feedback, here’s what I would change: If I were to start a podcast now, they would be in the form of a 30-minute “popcorn” podcast (an original term, by the way).

Also, don’t drink during recording in attempts to loosen up; you’re not N.O.R.E., he’s not DJ EFN, and this ain’t Drink Champs. Be yourself, don’t force anything but the prewritten questions to maintain a clear narrative.

My future self would tell 2016 me that feedback is a gift. Your audience offers a window into what’s working and what’s not. By embracing their input, you can adapt and improve your podcast. It’s not about compromising your vision but refining it. Listening to your listeners can lead to growth you might not achieve on your own.

Final Thoughts

Looking back, there are plenty of things I’d do differently. I would’ve planned more, recorded more episodes in advance, embraced feedback, and given myself more grace when things didn’t go perfectly. But the fact is, I wouldn’t trade the experience for anything. Podcasting taught me the value of capturing those real, unfiltered conversations and gave me a new creative outlet.

If you’re considering starting a podcast, I’d say go for it — know that it’s a grind, but one that’s worth it. Today, I can see the value of those moments in ways 2016 me couldn’t. Feel free to share your thoughts or experiences below; let’s keep the conversation going.