Secrets to A Successful Podcast

Deanna: So how do you keep a podcast on schedule? How do you relay that importance to the hosts and how important is consistency? This is something that I try so hard to get my clients on board with, and I fail at it miserably. So I'm asking you this question selfishly.

Jesse: Yeah. I make them understand the parameters of this and that you're going to make people miserable if you don't get things that there's moving parts. A good example is we have to be done taping almost everything by five o'clock if we're not going to make everyone else's life miserable, particularly one of the podcasts I do.

That's for a media company. If they don't have a transcript by six o'clock, they can't write an article for it. And somebody is going to miss a shift and then we're going to miss deadlines. So we have to have things done by a certain time. And it's known that on these days we need to deliver X content by X time.

That's what we're doing. This all has to be done. The other thing I will say, too, one of the things I did is I made a documentary on Project 2025. And it's been changing so fast in real time as we prepare the last episode.

Yesterday, we all did a creative call and we were like, “this is changing into something else. We're going to hit pause for a second." And it doesn't matter that we're late. No one wrote, we never said how many episodes this was going to be to anybody.

Let's just take a breather. And let this land a little, and I probably know how to write the changes to it. Then I got to do punch ins and get an edit approved. But some of this is just really good, healthy communication and making people understand that there's implications to your actions when you don't do this and consistency.

Podcasts are habits. And one of the main reasons why it's really hard to take off a week from podcasting is that people pick up other habits, you become their podcast for the gym, you become their podcast for their commute on this certain day.

And the real fact of the matter is, I could see it in the data, we're some people's Monday morning podcast, and they're not really listening as much on Wednesday and Friday. But we are there Monday, it's like nuts to see the bump at 6 pm EST and nothing happened between 2-6 pm for the most part, because that's when people start driving home or doing their commute. You can watch numbers just park for a while because you see that like some people, for example, my wife listens to political podcasts while she cooks us lunch in the afternoon.

That's part of her habit. If I ask her if she's listening to a podcast, she often looks at me like I'm crazy if she hasn't been cooking or commuting because that's her time to listen to podcasts.

Deanna: Yeah. You and I both work on a crazy number of shows each week. How do you find the balance when you're producing so many shows? Because you're involved in both the pre production and the post production process, along with then recording all of the episodes as well. So how do you balance that all out and make sure everyone is getting the attention each show needs?

Jesse: Things 3 has a wonderful thing where you can select how it puts a to do back into your to do box. You can do after completion by a certain amount of days or you can do just on each day. My weeks are pretty much the same every week is that I have to produce the same amount of content. And then if I'm working on special podcasts or I'm working on new launches as a consultant, I have to get that in.

So new projects and special projects and consultancy largely happen at night. It just is the nature of the beast that a lot of nights I break around 7 pm and spend some time with either my wife or tonight I'll go out to dinner with friends for probably from 7-10 pm and then from 10pm to 3am, I might be massaging edits on a video. I might be approving TikTok’s to go out. I might be doing a wide variety of things. But that's an average day for me is just knowing that, but I open Things 3 and I prioritize things. I try to write when I wake up each day, after I've checked email and text to make sure there's no emergencies.

The next thing I do is I open Things and I start putting what I'm going to get done in order and I hope I get done as much of it as possible. Sometimes I do calendar blocking. Sometimes I don't. Calendar blocking, usually for me, is one of the things I think people don't do when they're trying to be productive is they don't acknowledge where in the food chain they are.

So I, for example, have to be very responsive to you and all the other people who work for me so that you can get the next phase of things done. A good example is I have someone who edits my TikToks for me. So the way this works is I say things publicly and they listen back and then they turn long things I said in interviews, long form or in my members videos or in my public video of things, they turn them into short form TikToks. But then I have to read them, send them back, give them feedback. Then they add captions after we have all the graphics set. I have to do this so they can do their work.

So if I have 2 pm scheduled to review this Rolling Stone podcast, the Rolling Stone podcast might not be due for another week or two, I can do that at 4 pm. Whereas this is going to really help that other person who's in the middle of things if I approve it for them, so I try to just be malleable and accept that calendar blockings not really think I could do but prioritizing a to do list is.

Deanna: Yeah, for the most part I have been calendar blocking. And a lot of that is because it's a little easier for me because I'm working in bigger chunks because I'm doing the editing. So for instance, you have shared the Fast Politics and The New Abnormal calendars with me. So I know exactly when to be expecting files to come in, which is usually 10 minutes after the interviews have ended.

So then I can time block accordingly based on what's on those calendars and every once in a while something won't come in and I'll text you and I'll be like “hey, did this get moved?” and it just hasn't been moved in the calendar yet more often than not the answer to that is yes. Every once in a while Dropbox screws up and it's a good thing I ask because then you have to go and check on that.

I have found that calendar blocking that way helps me a lot because then once I'm done with all of the stuff that you and I work on, I can then slot in everything else that I have in between all of those things and that helps. But I do need to get back on the Things 3 train now that I'm doing stuff that isn't editing and doesn't have a specific time or day that it needs to get done. So that is definitely a good tip.

Jesse: Yeah, I've tried every to do app and that is the one for me that's simple, presents itself easily, and doesn't overcomplicate things.