Jeff Meyerson (@the_prion) is the host of Software Engineering Daily, a popular podcast that averages 20,000 downloads a day. It's also a successful business that generates close to $60,000/month in advertising revenue. Jeff joined the show to talk about the business of podcasting: What goes into producing an episode? How do you ask great questions? What's the best way to grow your listenership and land lucrative advertising deals? And what lessons from podcasting apply more broadly to all indie hackers?
Jeff Meyerson, welcome to the Indie Hackers podcast.
Thank you, Courtland.
You are a lot of things, Jeff. You’re a musician. You’ve released half a dozen albums. You are a software engineer. You’re the primary reason why the Indie Hackers podcast exists. You convinced me to start this thing way back in 2016 and most significantly, you’re the host of the Software Engineering Daily podcast which is one of my favorite shows and it’s also quite a remarkable business. I think you’re doing something like $60 grand in revenue per month just from advertising and your podcast, is that right?
Something like that, yeah.
Very cool. I would also describe you as a podcaster’s podcaster. Most of the podcasters I know somewhat surprisingly don’t listen to a lot of podcast. I probably spend three hours a week on a good week listening to podcasts. There’s many weeks when I listen to zero hours of podcasts.
You on the other hand are a very different creature. I’ve heard you complain more than once that you will literally run out of podcasts to listen to. You’ll exhaust everything on your playlist which is mind-blowing to me. How do you find the time to listen to that many podcasts and also how would you describe the benefits? How have you changed as a result of being such an avid podcaster listener?
Well we have norms around how many in-person conversations we need to having on a regular basis and if you throw out some of those norms and spend more of your time on the podcasts that are available, then you can consume a lot more of them.
Now there’s obviously some downsides to that but that’s pretty much been the tradeoff that I’ve been making for the last four, six, maybe eight years is I just listen to a ton of podcasts because the conversations tend to be more rewarding than the average in-person conversation for me.
Yeah, podcast is basically like being a fly on the wall of some other people talking which is super cool because you can listen to almost anyone. You can listen to basically world leaders, experts in their fields, discuss topics as if nobody else is listening but the downside is that you don’t really get to interact.
There might be times when you want to jump in and ask questions. Does that frustrate you at all or do you feel like you’re missing something by trading a lot of these in-person conversations for podcasts?
That doesn’t frustrate me. I really like just listening. What’s not good is the amount of time I spend listening to podcasts relative to in-person conversations. I think at time it has had a hobbling effect on how good I am at normal social interaction.
It’s funny you say that a podcast host because one of the things that I first noticed after you convinced me to start a podcast was the way I host the podcast affects my in-person conversations.
So, I would start asking people questions the same way I ask questions on a podcast and at first, I was a little self-conscious about it. Like I would say something and I’d be like did that just come out of my mouth? It sounds like such an interviewer question.
But people really appreciate it when you ask them interesting, sort of unusual deep questions. People don’t necessarily want to talk about the weather all the time and so for me, I would say, being a podcaster has made me a little bit better socially just because I have more to talk about and also, I’m better at asking questions.
To a point though, right? Because if you take it too far, then people are like can you stop psychoanalyzing me please? Can we just order something on the menu now? Can you stop asking me about my childhood fears?
Yeah, you’re right. There’s definitely an extreme limit that you can go beyond. One of the interesting things about podcasts is both you and I probably know a lot of people who started podcasts and the vast majority of people that I know that started podcasts have ended up quitting in the first three or four episodes. They just don’t stick with it.
You probably know even more because you seem to be somewhat of a podcast evangelist. You’re the reason why I started this podcast, for example. Why do you think it is that so many people who start podcasts end up quitting early and what are some things that they can do have more longevity?
I think this is more of a general question around persistence. What are the things in your life that you’re going to be persistent about? You want to choose some number of things that you are going to be persistent about and it’s totally fine to start things that you choose not to persist on and also to have certain things that you’re periodicity of persistence is going to be once every month or once every six months.
Maybe you just release a podcast whenever you feel like it, whenever you have an excuse to. So yeah, I think it’s like people try a podcast, maybe they’re not natural at it. They don’t – it takes some getting used to, they have a bad experience with the first couple and then they drop it.
I mean the same thing happens with blogging, right? People start a blog or a Twitter account and then they just don’t keep up with it and it falls by the wayside like any kind of project.
Well you have how many episodes of Software Engineering Daily now?
Eleven hundred, that’s some pretty amazing persistence. I’m only at like 115 or so with the Indie Hackers podcast. What would you say are some of the things that have allowed you to stick with it?
I really like it. I mean I just genuinely enjoy these conversations. They’re a great way for me to learn personally. It’s a business that works for me and I’m very desperately holding onto this business and you know, it’s kind of like I’m very paranoid about the business falling apart. So, I’m quite rigorous in adhering to the necessary deliverables to keep the business alive.
So tell us a little bit about the show. It’s called Software Engineering Daily. You release a new episode on Mondays through Fridays so you’re releasing these at a relentless pace. What do you talk about on the show?
The topics of conversation are mostly deeply technical software subjects. That’s kind of the moat of the podcast and it was started based on essentially a direct clone of Software Engineering Radio which is a podcast I was a volunteer for for three years.
And I got the blessing of Software Engineering Radio. I remain very good friends – the editor of Software Engineering Radio, Robert Blumen, has been a mentor of mine and the structure is just a two-person interview format, the classic podcast interview format except the subjects are things like database, Java Script frameworks, distributed systems.
And then subjects that are more sociological or cultural in nature or management, soft skills kinds of things, business-related things. Things that are less demanding of a technical background. So I would say I probably try to do one in four shows is less technically demanding for the listener but the vast majority of the shows kind of require a software engineering background
Yeah, I came across a Tweet the other day and it was pretty interesting. It said something about how the people to follow used to be the educators who teach in public but now in the age of podcasts, the people to follow are those who learn in public. And so that would be you on your show talking to this software experts, deep diving into these topics that you didn’t know very much about beforehand. And you’re learning from your guests and public but also people who are listening in are learning.
And the justification for why this is sort of a better way to learn is because we live in an age where people are so specialized that there’s no person you can sort of teach everything you need to know. So, you’re either going to constantly be fighting a bunch of teachers or you can find somebody who sort of matches up to our learning style and just follow along with them as they learn. So I wonder how you think about this. Where do you see your role in both learning on your podcasts and in teaching others?
So, the thing is I grew up not doing very well in school. I’ve always been a rabid learner and I’ve always liked learning about a wide variety of things.
And so, when I found the podcast niche – what was originally a niche – now it’s a bigger obviously medium of communications. But I really found that it suited my learning habit and you know, over time, as I’ve started podcast and talked to more people about podcasting, I’ve learned that there’s a lot of people who learn quite effectively from podcasts.
And you know, it’s kind of debatable, you know, how much are you actually retaining? What are you learning? Are you learning about the actual subject of the podcast? Are you learning about government or geo-politics or software engineering or are you really learning how to have a conversation with other people, whichever of those you’re actually learning, I do think that there is something material that people are taking away from these podcasts?
I certainly feel like I gather information whether I’m listening to a podcast or if I’m hosting the podcast and I feel it’s really valuable to me. So, it’s a learning process that certainly works much better for me than the sitting in front of a lecturer who’s the authority on something, medium of learning.
You had an episode of your podcast recently with Tyler Cowen. He is an internationally recognized economist but he’s also a generalist. He’s got his own podcast. He brings on tons of guests from a diverse set of backgrounds and fields and just talks to them about pretty much everything.
The two of you had an interesting exchange where you discussed sort of the ideal format for the podcast and Tyler comes down hard on the side of being very anti-narrative. He thinks that a lot of people just listen to podcasts because they’re soothing and because it’s just – I don’t know, it just feels good to sort of hear one event after the next in chronological order. We like stories.
But for his podcast he just throws all of that out the window and he’s just optimizing for the number of insights per minute. So, he will rapid fire interesting questions at his guests that also have interesting answers with no real regard for story or narrative or conversational flow.
It can be a little bit jarring but he’s just optimizing for being insightful. I wonder how you think about this with your show, Jeff? What are your goals with each episode and what do you want your listeners to come away with?
Well first of all I’m not sure how much I believe him when – some of the very strong opinions that he states, I mean, that’s something he’s owned up to. That he takes a very strong opinion and sometimes it’s not actually the measure of subtlety that he would believe if you pressed him which is in and of itself, a very useful, narrative device, a very useful rhetorical device.
You know, it varies from show to show and actually a lot of it depends on who the guest is. So, when I’m preparing for a show, I’m listening to podcast interviews with that person, I’m reading their blog posts, I’m getting a feeling for who they are and what their conversational cadence is. And I want to modulate my conversational cadence to something that’s something that’s going to fit well with theirs.
So, like Tyler, I know that he is comfortable with that format of the rapid fire, jump from topic to topic, very few filler words, that kind of things. So in his case that’s going to be – I’m going to try to adopt that style and I’m going to try to – first of all because I know he will respect that kind of style, second of all because I know it will be amenable to a good conversation.
But yeah, I mean, you know, if I’m having a conversation with somebody else, I may adopt a different style, there may be more filler words. And other times, I may just totally experiment with a style. Like if I’ve been listening to a conversation with Tyler a lot I may just adopt his style for a random guest about distributed databases and it might go really, really well so I don’t have – I actually don’t have super strong opinions about format and I like mixing up the different formats.
Yeah, I notice that when you were interviewing Tyler you adopted his style so you were sort of rapid firing questions at him and he was indulging you which was cool to hear. It was like listening to an episode of his show but with him as the guest instead of the host.
I think about this a lot with regards to the Indie Hackers as well. How much do I need to change up my questions and my style depending on who I’m talking to?
I’d kind of like sparring.
Yeah, I think that’s accurate. You have to match up what you’re doing to what your guest is doing and I think when I first started I didn’t really think about it in those terms. I just kind of asked the same questions to everybody and I would get wildly different results, sometimes good, sometimes bad and I would wonder why. But nowadays I’ll change it up.
For example, if I’ve talking to somebody whose business has had a lot of longevity, if I’m talking to a Pelvey or a Natalie Nagle or Jason Fried, I’ll try to stock to higher level philosophical questions because that’s where their mind is at. They’re reflecting on the entire 20-year history of their business.
If I ask them how their business is gone, I’m basically asking them how their life has gone. If I ask them about a mistake they made, they think about a dozen mistakes. They don’t really think about the tactical realities of one specific situation. They just reflect on the entire theme of making mistakes and what it’s like to make mistakes and how important those are in the greater scheme of things. Right? They answer very differently.
Versus when I’m talking to someone like you you’re a little bit newer to your business. You’re a lot more tactical. The short-term matters a lot more to you and also I know that if you keep learning at the rate that you have been learning, that you’re going to be in a very different place by the time you’re 40 than you are now. So, I’ll ask you a totally different set of questions. So, yeah, I’m right there with you. There’s a lot of different ways to interview different people and I’m still figuring it all out as a podcast host.
It’s totally Greenfield. Very Greenfield opportunity and it’s a lot of fun experimenting with it.
Yeah, it’s very unusual and I think a lot of fun to be so deliberate about having a conversation with somebody. It’s not something you do in your everyday life.
Let’s talk about how you started Software Engineering Daily. You mentioned earlier that you were working for another podcaster on another show. You had an apprenticeship of sorts. I don’t know very many people who have had apprenticeships so tell us how that worked out and how that led to you starting your own show.
It was wonderful. I’ve historically been a very bad apprentice. I’m very bad at taking direction from people. But this was a case where I started listening to Software Engineering Radio in college and there was a call for hosts on one of the shows, where they said we’re looking for new hosts. We’re a volunteer only organization. If you want to be a podcast host, send us an email. So, I sent an email and Robert Blumen gave me a shot.
I started software podcasting with Software Engineering Radio and I continued doing that through my early years as a software engineer because I started in my last year of college and I continued to do it my first couple years of being in the working world.
And eventually I just realized that there was a huge hunger for more content than we were producing and I also saw emails from sponsors that were – potential sponsors – that were coming in. This was a volunteer only organization. It wasn’t accepting sponsors at the time and so we were turning away sponsors. And so, it just kind of seemed like an obvious opportunity.
At the same time, I wasn’t really enjoying my work as a software engineer and so I just saw the opportunity and it was kind of obvious to me. It was like okay, I should start a software engineering podcast. There’s advertisers that want to advertise on it. Let’s give this a shot.
I think a lot about the operations behind your show because you’re putting out five episodes a week which quite frankly sounds exhausting just to hear about. I’m struggling with just two episodes a week and on top of that you’re funneling a lot of the revenue you make from advertising into these other projects and start-ups that you’re working on that we’ll talk about a little bit later.
Have you ever thought about doing what Software Engineering Radio did and putting out a call for hosts? Trying to bring on a new host to sort of help you out or maybe even replace you so that you’re more free to work on other things?
I tried it – here’s what makes it tough. Software Engineering Radio is a volunteer only system and also Robert is an incredibly good manager. He’s one of the best managers I’ve ever had and I’ve been managed by him for a volunteer only capacity.
When I’ve tried to bring on other people in a volunteer fashion, first of all, it breaks the format. People I think get used to hearing a host’s voice. I mean I imagine if you tried to bring on other hosts, you would see a drop in the listenership for those episodes. People want to hear you.
People don’t like change.
I don’t know if people don’t like change. I think people – it’s sort of like, you know, imagine if like Seinfeld was like, ‘hey, Jerry is no longer with the show’. You have like the end of season seven and Jerry’s like, “I’m moving to Hawaii” and everybody is like, “wow, what are we going to do without you?” Then Jerry moves on and the last scene is somebody moving into Jerry’s old apartment. That becomes the protagonist for the next season and it’s Jerry’s brother, John Seinfeld. And it would just be a disaster.
A total stranger.
And I think that’s what happens sometimes when you have guests hosts but for Software Engineering Radio, that’s always been the norm. It’s always been a volunteer show with a rotating cast of hosts. Robert’s always done an incredible job of ensuring quality and managing the different hosts. It’s a lot of work. It continues to be a lot of work for him. And delegation of tasks to different podcast hosts is something that I have not built a core competency in. So, I think it just becomes a very different show if you delegate.
Yeah, you know when I first started the Indie Hackers podcast I told myself that I was going to experiment a lot with the first 10 to 15 episodes, precisely so that I could avoid this problem of being locked in to one particular format and then I totally didn’t do that.
It was just so much work getting the episodes out, also working on the website, selling ads and coding and all this other stuff that it was all I could do to get 10 episodes out of the door let alone experiment with different formats. So, here I am today, not that experimental, but nevertheless I’m still trying to change things.
The quick chat format works.
Exactly. I’ve got the new quick chat format. It’s not that much of a departure from the regular Indie Hackers episodes but people seem to like it and maybe there will be more change to come.
I’m curious about how you’re thinking about this nowadays. Have there been any major changes to Software Engineering Daily since you started and do you think you’ll make any changes in the future despite the fact that there might be some resistance?
When I tinkered with the format I reverted pretty quickly mostly because first of all, the one-on-one interview format I believe still has so much depth. I never really get tired of it. I experiment within that format. You know, the one adjustment I’ve been making recently is I got the equipment to have a home studio set up now and I’ve started to do some in-person recordings like at my kind of apartment/office thing. That has a totally different dynamic. I think you’ve done what a couple in-person shows?
Yeah, I’ve recorded like four or five in-person episodes.
So you know that’s almost – it’s almost so different that it’s like a different format. So that’s the only –I would say that’s the only significant departure that I’ve made for a longer period of time and I don’t know, you know, maybe it’s just like innovator’s dilemma. Maybe I should be experimenting more rapidly or something or doing like panel formats and …
I hope you experiment in part because you’re a smart person and if you have more time, you’re gong to come up with some really cool stuff and then I can watch it and maybe steal some of it.
But also, because I think audiences are probably more forgiving than we give them credit for and of course, they might revolt at first to any unwelcome changes but in the long run, if it’s actually good, I think people will warm up to it.
Let’s talk about this interview format that you’re so in love with and I’m also in love with. Specifically, I want to talk about how you prepare for an interview on the Software Engineering Daily podcast. When I first got started, you gave me a few pieces of advice and your number one piece of advice—the one you were most adamant about – was to prepare. You kept telling me over and over Courtland, if you’re going to invite somebody on your show put in the work to prepare questions specific to that guest. Do you remember that?
But you agree that that was pretty important – the most important thing.
It’s extremely important advice and it’s painful when I’m listening to a podcast that somebody else is on, especially if it’s a guest that I’m gong to prepare some questions for and I hear them being interviewed by someone who basically has not idea who they are and didn’t really put any effort at all into this interview. So, yeah, I’m right there with you.
It is the simplest advice. I guess it’s not easy for people to follow because I prepare one to two pages of questions. The general rule I started to develop is a page of questions per 30-minutes of interview.
How much is a page? Is it like 15, 20 questions?
Let’s see, it’s so – so it’s like whatever the standard Google docs format is, I do control shift 8 and make bullets and you know I cover an entire page with bullets and maybe some headings to break up the different areas of the podcast.
And I try to have a narrative progression in mind which is sometimes not great because they you stick too tightly to the narrative progression that you imagine. You know, this story arc that you imagine and if you adhere to it, sometimes it’s problematic.
Sometimes the guest is so good that they don’t want to follow a story arc and you shouldn’t be following the story arc. But, you know, you’re just sticking to the tracks that you’ve laid out for yourself and then it’s counterproductive and you know, this is why it’s kind of like sparring. It’s like you know, you’re – everybody has a plan until they get punched in the face and the the difference with podcasting is you can continue with that plan even if you do get punched in the face and then it’s just 60 minutes of pain and the guest trying to go in one direction and you trying to go in the opposite direction and it’s not pretty sometimes.
Yeah, my favorite is when you asked a guest sort of the first question out of their story arc and they just tell you the entire story in that five minutes and you’re like well there’s the interview. Now what do we talk about?
Yes, exactly. So yeah, preparation, that’s the most important thing and that’s pretty much it, you know. The preparation part of it has as much depth to it as the interview itself. How are you going to prepare? You have a fixed amount of time. Are you going to listen to all their podcast interviews? How many podcast interviews have they done? Are you going to dig up the old YouTube videos that they’d done? Are you going to find their old blog posts, are you going to read through those? Are you going to quote them? What do you want to do?
How much time do you want to spend talking? How much time do you want to give them? Do you want to ask short questions? Do you want to ask long questions? Do you want to do the say a statement and wait for their response kind of thing or do you think they’re going to be the kind of person that’s just going to wait for you to ask them something with a question mark at the end of it? There’s so many different avenues to be explored. So, yeah, preparation is kind of – you can begin to look forward to it if you get in the right frame of mind.
You said in the past that as a podcaster you don’t need to have the right answer but you do need to have good questions. What goes into crafting a good question?
Empathy. What kind of question does this person want to answer and can you ask a question that is brief and concise but also not a question that they’ve been asked before?
As you’re preparing for the interview can you keep the totality of every question that they have been asked in prior interviews, in prior You Tube videos, can you keep the totality of all the information that they have explored in blog posts in your head at the same time and can you constantly re-sift and re-format that information that they’ve said in the past and use that to synthesize your questions. I think that’s what’s really important.
Man, I can identify so much with that short-term working memory thing where you’re just trying to keep a lot of information in your head as you have a conversation with somebody. It’s almost like coding. When you’re writing code, you’re not only writing code but you’re remembering what files you have open, you’re remembering what functions you ‘re working on, you’re remembering what’s in your terminal, you’re remembering what’s on your clipboard that you’re about to paste.
When you’re interviewing someone on a podcast, you’re remembering the other conversations they’ve had. You’re remembering the conversations you’ve had up to this point and the questions you’ve asked and the answers they’ve given. You’re trying to remember the next question that you’re going to ask and what you can do to tie the different themes together and man, is it exhausting to do that at the same time you’re trying to have a conversation and listen to somebody. I am basically worthless for the rest of the day after recording a podcast episode.
Yeah, I can definitely relate to that.
On thing you mentioned is that when you’re preparing for an episode you’ll listen to other podcasts that the guest has been on in an effort to make sure that you can ask the guest unique questions that they’ve never been asked before.
I find myself pulled in the same direction almost to such a degree where I don’t want to listen to other podcasts because then I end up defining my own shows, my own set of questions based on those other shows because I’m so obsessed with not being repetitive. Do you feel the same thing? Do you feel like if you listen to another episode that one of your guests has been on that you have to make yours completely distinct?
Yes. Yes, I think it’s really important to have content that’s extremely distinct from the other interviews that are out there, especially because if this is a person that’s been interviewed a number of times before, this is probably one of these popular people who has spoken a lot, has been interviewed a lot and the thing about these kinds of people is there are going to be people in your audience who are going to be going through a phase of like listening to all the DHH podcasts that are out there.
So, if you want to be on that like playlist and you want to be a good track on that playlist, you’re going to have to be something different. You can’t just ask DHH like so why doesn’t Rail scale or why don’t people think Rail scales? He’s been asked that like 50 times. And he may give it a different answer this time. That may be good but probably not.
And one of the additional advantages that I think helps with asking unique questions to guests is you kind of throw them off their game a little bit, especially if they’re somebody who’s super popular, if they’re doing the podcast circuit, if they’ve been in 10 different episodes this year, by this point they probably have somewhat rehearsed answers to some of the questions that they’ve been asked over and over again. Or they just end up recited the questions from memory which is very boring for them. It’s boring for you. It’s boring for audiences.
But if you ask somebody a question, especially right out of the gate that they’ve never heard before, it kind of forces them to wake up and to be on their toes, to be a little bit more engaged and thoughtful which is what you want out of a guest.
I’ve also heard of a few tips and tricks. I’m always looking for ways to make questions more interesting. One of them I got from a friend who pointed out that if you combine any two random concepts, you’re very likely to get something that no one’s every heard before. That’s just how the math behind combinations work.
So, for example, if I were to ask you hey, Jeff, I know you’re a fan of Warren Buffet and Charlie Munger. Charlie Munger recently gave some advice that the fundamental algorithm of business and then life is to find what works and keep doing it. To just repeat what works. How do you think about that in the context of you growing your podcast, Jeff?
In one sense that’s a question you’ve gotten a lot of times. How do you grow your podcasts? But in another sense, since I’ve combined with this other thing, it’s unique and it’s going to force you to give a more thoughtful, original answer. So, I’m curious about how you think about this. Do you have any tricks? Do you have any techniques for coming up with interesting questions, especially when you’re talking to guests who’ve already answered all these questions a thousand times?
I think that’s a great one I think if you do it too much it can be contrived. If you take it too far, but generally speaking I think it’s wonderful.
There are a number of patterns that you can follow like for example, if you’re asking – if you find yourself interviewing somebody about distributed databases, there are questions you can ask every guest who you’re interviewing about a distributed database. For example, what happens during a read to this database? What happens during a write to this database? And if it’s a distributed database, a lot is going on.
If you’re writing to a distributed database, there’s all these different things and like what happens if there’s lock contention or is this a master list? These details are pretty interesting.
So, for your podcast, there’s probably like what is your marketing strategy? What is your sales funnel look like? What were the bottlenecks that you developed in your hiring process? Something like that. Those kinds of questions are almost boilerplate things. They fill in a lot of time. You can have these lists of templated questions that fit into most of your podcasts.
I think you can take that to the extreme and be like Harry Stebbins and have the lightening round and you know, re-use your questions from interview to interview in a very blatant and totally – you know, he owns that. And you can do that. It works with some people.
So, yeah, I don’t know. But as far as being unique I think it’s really important and I think you know, you should never stop being paranoid about it because that is honestly your vector bring able to outwork people. If it’s hard to be unique, then that means you should keep trying to do it.
So you worked at Amazon prior to starting your podcasting business. Amazon is sort of famous for their flywheel model of growth which I believe, but I’m not 100% sure, it sort of has infiltrated every level of Amazon, every team sort of thinks about this flywheel. Is that right?
I would say so.
So can you explain to us your perspective on how the flywheel works, whether or not it’s a good model and how if at all, you’ve applied it to your business?
Yeah, the idea of the flywheel is that you have a process of how your business works almost like a perpetual motion machine. And there are inputs into the business that create outputs and those outputs have exhaust effects that serve as inputs back into the business in such a way that the overall engine grows over time.
So, in the case of Software Engineering Daily, I guess a simple way of describing it would be the listenership grows over time, the volume of content grows over time, the number of people who are listening to the podcast that might think about advertising on the podcast is implicitly growing over time because there’s just more people that are listening which leads to more ad dollars and ad dollars can feed back into the business and serve as a resource perhaps invest in things like marketing or invest in better microphones. That’s a very simple way of looking at it. I just think the flywheel is useful because if you can’t imagine the flywheel of your business then it’s almost like does your business grow over time? Does it?
Does it work?
Does it work? I mean it can work. It can be just a business that makes the same amount of money every single year and never really grows. That’s fine. But it’s probably better to have a flywheel.
Let’s talk about the advertising portion of your flywheel which clearly what’s powering your business at least in terms of revenue. How do you grow your advertising revenue and what are some lessons you’ve learned while doing that?
It’s not easy right now because people still don’t buy podcast ads. I mean some people do, most people don’t. So, we have a lot of ways of engaging with advertisers. We will say on the podcast hey, we’re looking for advertisers for this season. We’ll get some inbound. I certainly do a lot of outbound, reaching out to companies and saying like hey, Microsoft you should probably Software Engineering Daily and 99% of the time they’re like no, why on earth would I want to sponsor a podcast? We’ve got billboards to buy! You know, we’ve got swag to buy. We’ve got bouncy balls with colored lights inside. We have a budget allocated to the bouncy balls but podcast ads, no, not a chance.
So, it’s not easy. And it’s a struggle right now and I mean that’s why it’s a good time to start a podcast, especially a podcast business because it’s just not easy right now. So, one, you can fight for it but two, the market is growing. I’m seriously not being coy here but it’s not easy to find advertisers.
Nevertheless you’ve still managed to grow your advertising revenue to something like $700,000 a year. How did you get to that point? How do you, as a fledging podcaster, as a fledging content creator, convince advertisers to give you your first dollar?
Email people. Just email advertisers. Email companies that would make sense to sponsor your podcast and email them time and time again. There’s no easy way of doing this. Go to conferences. Go talk to people. Don’t take no for an answer if it makes sense not to take no for an answer. Be a hard negotiator.
You’re selling something that you have a surplus of and so you need to sell that aggressively and it’s – you need to believe in it also. Like I wouldn’t sell this thing as aggressively as I do if I didn’t believe in that. I truly believe podcast ads are a much better investment than so many of the ways these companies spend money on marketing.
I don’t know, I go to these conferences, I go to a lot of software conferences, and I start to go crazy because I just look at how these companies are spending money on marketing and I’m like I am so happy I’m in this business because they’re going to realize eventually that it’s just – that what they’re doing is madness.
Yeah, I remember selling ads for the Indie Hackers podcast and you actually helped me out a lot in the beginning because you gave me a list of leads really of people that you thought would be amenable to purchasing ads and so I just started emailing them.
But before that I was basically doing what you were just talking about and hustling a lot. I was telling everybody that I knew that I had a podcast, that I had an email list and that they could sponsor it if they wanted to. And it turns out that because I was running Indie Hackers most of the people that I knew were running these tiny, fledging Indy Hacker businesses.
Not the best customer base.
Yeah, I loved them. I mean they were great. They’re great people but they’re also not the best customers because they don’t have the largest marketing budgets so they’re going to spend $500 on an ad, they really want that ad to perform and they’re really going to check I with you at all times of day and night every day to figure out how well their ad is doing.
Whereas, when I was selling to big companies, they would just say hey, Courtland, this sounds great. Here’s a check for $2,000. Come back next month, we’ll do another one probably. And they wouldn’t check in at all. They almost wouldn’t’ even care. So, that was particularly great.
I always figured the best ad deal that I could get would be like some sort of year-long sponsorship commitment where I wouldn’t have to sell ads at all. How do you think about it with your podcast? What’s the best ad deal structure?
Definitely bigger company, long-term. Here’s the difficulty. Most of the biggest contracts that we get are brand advertising deals and brand advertising deals are not measurable. They are the billboard equivalent of a podcast ad.
It’s very hard to get those deals. There’s just no short cut. You have to have an internal advocate within the company. We’ve certainly gotten like plenty of direct response deals also where they’re actually measuring go to Microsoft.com/SEDaily and get a free azure windbreaker or something. You know? If you give us your email address, you’ll get a free windbreaker. That kind of thing. Those kinds of deals are great for actually getting retention if these people actually want to advocate to their manager with a data-driven argument.
But most of the time these are not data-driven arguments that are being had within these companies. It’s literally like do we like this guy? Do we want to advertise on this podcast? Does he make us feel good? That’s – man, advertising is a weird, weird business and – I wish I could give you more quantifiable answers but it’s really more of a touchy-feely like figuring it out kind of business.
I recently interviewed Sam Parr who runs a media company called The Hustle. And they make something like eight figures a year just from selling ads on their newsletter which they then taken and use to expand to other others.
So, for example, they just launched a podcast. So, I asked him why he started with a newsletters, why not start with a podcast and he said because podcasting is “a bad business”. I wonder if you don’t agree with him, Jeff, after listening to you describe how difficult it can be to sell to advertisers. Is podcasting a bad business?
I mean I like it. It depends on what do you want out of your business. Do you want to spend a ton of time every week preparing for podcasts interviews and having podcast interviews? Do you want to figure out the strange contortions of running a podcast business at scale? Do you want your podcast business at scale or do you want it to be lead gen for something else? What’s your vision for how this fits into your portfolio?
I liked your interview with him, but I’m not sure I agree that like you can uniformly – it’s sort of saying the book business is a bad business. I mean it’s like pretty good business for Dan Brown, you know.
Well this goes back to the question of why so many people quit working their podcasts so early. And I think what you just said pretty much summed it up which is there lots of different reasons to have a podcast and they’re all very personal.
And it’s very easy to quit something if you don’t get what you want out of it but it’s very hard to get what you want out of something if you don’t know what you want. So I think people kind of start podcasts because they’re cool, they’re trendy but those aren’t really good reasons if you know you’re trying to enjoy towards some measurable result, if you know that you’re doing it for the love of the craft or something like that, then it’s easier to keep going.
Let’s talk about books for a second since you brought them up. How do you think about the difference between audiobooks and podcasts because I know myself I probably spend five times longer listening to audiobooks as I do listening to podcasts every week?
Right. So this is where it gets into why are people actually listening to podcasts and when I psychoanalyze myself on this question, it leads me to some uncomfortable territory which is that I think people listen to the two-person audio interview format of a podcast often times, because they want to feel less alone. And they want to feel like they’re surrounded by the kinds of people that they want to be having dinner conversations with or just grabbing a cup of coffee with.
I think oftentimes peoples listen to these podcasts in a binge format because they’re really in a state where they’re not getting what they want out of their in-person social interactions but they feel desperately that they need social interactions that rise to the level of preferred quality.
If we’re talking about pure like that insights per minute idea, probably audiobooks are better but then again, like you know, then it’s like can you listen to an audiobook in the gym? I mean I can listen to a podcast in the gym. I can listen to a podcast when I’m going for a run. Audiobooks are more I have to be like cleaning the kitchen maybe, I have to be folding laundry, something that is much less mentally demanding. So, yeah, this is an evolving question for me and then also it depends on what kind of audiobook it is. There are some audiobooks that are just so compelling that I can listen to it even when I’m in a somewhat distracted state. So yeah, I don’t know, hard to generalize.
Yeah, I definitely find myself reaching for that rewind 30 seconds button a lot more often when I’m listening to an audiobook than when I’m listening to podcasts to your point.
They’re definitely just denser, they require more of your full attention but on the flip side, there’s also this phenomenon where books are often way too long. In order to justify publishing a physical copy of a book, you need to make it 200 or 300 pages long and so oftentimes books that could be just 50 pages or 100 pages end up being double that like.
I wonder if in a world where people are conditioned to listening to audio or relistening to so many bit-sized hour-long podcasts, if there’s not room for people for people to write books that are just the right length, just an hour long book that tells you everything you need to know. It doesn’t go into any fluff.
Did you listen to “Can’t Hurt Me”?
No, I haven’t.
That’s ones pretty good. That’s the David Goggins book. He’s a Navy Seal that’s been on a lot of podcasts recently. But the audiobook there is an interesting format because it’s actually audiobook in normal format interspersed with little interviews with David. So, they kind of blend it and so I do think that there’s a lot of room for exploration.
Very cool. I think things are going to be in a pretty interesting place five or ten years from now with this whole intersection of audio and learning stuff especially in a world where everybody is sort of comfortable listening to things for hours on end.
Let’s talk about what you mentioned earlier which is that a lot of people listen to podcasts to feel less lonely. I think the flip side of that is also true somewhat thought that being a podcast host can be pretty lonely. There’s no way to people to commandant your podcast really, there’s no way for you to really interact with your audience unlike so many other types of businesses.
It’s almost surreal. You can watch your download numbers go up every single week, week after week, but never actually talk to or meet anybody who listens to your podcast because it’s so distributed and you’re so disconnected from them as a podcast host.
I wonder how you think about this with your podcast, Jeff. How do you know what your listeners want? How do you know what they care about? How do you connect with them when there aren’t really any good channels for doing so?
I don’t know. We have a slack channel you know, I get email sometimes from people. I do the Twitter sometimes. What I find is that the listener base of Software Engineering Daily, they’re silent until something is wrong and if I do a show that’s not great, I will hear from people. If there’s something wrong I will hear from people. If I put out a call for suggestions I will hear from people. So, I know people are listening and you know, at conferences I talk to people occasionally.
Yeah, it’s like you have to go out and do it yourself. You have to go out and meet people. You have to go to conferences. You have to create the slack. You have to rile people up Twitter. Otherwise, you just never going to hear from anyone. It’s bizarre man. I think it’s so weird.
But you’re also good at getting your listeners to collaborate. For example, you’ve had a couple people who worked together to build a mobile app for Software Engineering Daily which is so cool. And you’ve also spun another project called FindCollabs. So, this is basically a website that allows people to collaborate on projects together with strangers over the Internet. I think it’s perfect to your audience because you’re catering to software engineers and who better to collaborate with strangers over the Internet on different projects. Tell us a little bit about FindCollabs. Why did you start it and how does it work?
Right. So actually I started FindCollabs with the goal of making a music collaboration tool do I’m very passionate about music and the thing that’s tough for me about music is that I really like to write music with other people but there’s very few people I like working with on music because I like people that take it seriously. Like it’s like if we were to, you know, if we were to say hey, Courtland, let’s go – let’s start a company and we’re going to bunch ideas off of each other for the next week. We’re gong to meet twice a week and we’re going to bounce ideas off of each other, then we’re going to start hacking on something. We would take the whole process pretty seriously.
The musicians I worked within the past, there is no way to get them to take it seriously. It’s literally like let’s get together, let’s like have a beer, let’s chat. Maybe we’re going to work on some music. Maybe not. Who’s gong to be doing what? It doesn’t matter. We’re not going to be organized about this thing. So, FindCollabs started as a place where people would take it seriously to collaborate on something.
I kept it general but really the goal for me was to create music collaboration place. A place where a drummer could get together with a producer and a vocalist and perhaps another producer and collaborate on things. And they could rate each other. The rating system is really important. That’s a big component of FindCollabs.
So really the backbone of FindCollabs is a place where you can create a product, you can create a system of roles and people can slot into those roles and work on the project together with a well-defined division of labor.
Now obviously this works well for software engineering to the same degree that in fact it’s turned out to be a better fit for software engineering largely probably because of my audience. I’ve announced this on Software Engineering Daily and I’m like hey, if you’ve got a project and you’re looking for collaborators post your project on FindCollabs or if you’re a person who’s looking for a project go on FindCollabs and look for a project.
Obviously, my audience is software engineers and software engineers are producing a lot of software. They’re not producing a lot of music so it hasn’t into really the music collaboration site that I envisioned but there’s a lot of people that are posting software engineering projects and finding collaborators for software.
Yeah, I mean if you’re a software engineer of if you have a creative project or creative business in mind and you’re looking for people you can go to FindCollabs. I mean more generally the problem that I’m pursuing is we’ve got all these tools for making very cool things on the Internet. We can make music, we can make businesses, we can make art projects, we can make open source software.
Why are we going at it alone so often? Why is it so hard to find other people to work with and to collaborate together? I think there’s a variety of reasons for that but it definitely does not feel like we are at the end state of internet creativity because if we were, we would see a lot more large collaborative projects.
Yeah, it’s a tough problem to solve. There’s a lot of friction there that prevents people from working together and you’re right, the tools we have today with email, with slack, with video chat, with pretty much all the tools that make remote working so possible and so common, it should be easier for people to collaborate.
This whole thing reminds me of my fate question from earlier where I was talking about how the fundamental algorithm of life is to figure out what work and keep doing it. It seems to me that what’s working with your business is the software engineering angle because of your audience, with your podcast, because software engineers are familiar with using computers to collaborate already whereas musicians maybe use other means that your using to meeting in-person and studios, etc. How do you think about the future of FindCollabs given that it’s veered off the course that you initially intended?
I think it’s fine. You know, the vision for FindCollabs is very big. The idea is that if you want to develop a reputation as a person that builds collaborative projects online, this is the place where you build that reputation. So when you finish working on a project, your collaborators give you a review from zero to five stars and I believe that much like Air B&B moat over the long run has been the reputation system, I think that FindCollabs the moat will be the reputation system.
And I think that if you develop a good reputation at producing open source software, maybe people will correlate that reputation with being a good musician. I feel like if the site grows big enough then people who develop a lot of open source software, some of those people are going to be musicians. Maybe eventually they’ll start working on music projects with each other. Or maybe somebody listening to this right now will come and work on music projects with me which would be fantastic. I’ve got some projects posted. You can post yours. I’ll work on them with you.
So yeah, I mean I just – the thing is I just haven’t really seen other people solving this problem. I think it’s an acute problem. I think it’s going to exist for a long time. I don’t know if I’m going to be the one to solve it but I just think it is strange that it is not easier to collaborate with other people on projects on the Internet.
It’s not easy to find people and I think it’s largely a trust question. That’s why the reviews are so important to the FindCollabs website, is the idea that you will be reviewed at the end of your projects, puts some accountability on you. And I just think that accountability is crucial. It’s what’s lacking in our current environment.
Yeah, you said a couple different things there that I think are underrated. The first is reviews. If I look at a website like Amazon, a huge part of the reason why I shop there is because of the reviews. If I go to a random store on my street and try to buy a blender, how do I know which blender is good?
If I go to Amazon, every blender has hundreds of reviews. I can be pretty confident that I’m going to pick out one of the best blenders in the world because if the reviews. Air B&B is another example. Twenty years ago, I probably would not have stayed at a random stranger’s house when traveling, but today I can go on the website. I can see that this place has been reviewed by hundreds of people who stayed there. They say what’s good. They say what’s bad. So, I feel a little bit safer. I feel like I’m not going to be axe-murdered just because of this review system. And of course, there’s hundreds of other websites that rely on reviews, that create new models of collaboration and interaction because of reviews so perhaps FindCollabs will be one of them.
The other thing you said that I think is underrated is that as a founder, you don’t necessarily have to stay at the place where you start. You can start something small, you can accumulate some advantages, build up your revenue, build an audience and use that to sort of parley yourself into a bigger win and the next step – a different market, a different type of customer, building more features to different products – whatever it is.
You don’t necessarily have to start with whatever your end goal is. I think this is very unintuitive to first-time founders.
I find myself saying this over and over again. People bite off way more than they can chew when they start because they think that whatever they start with that’s what they’re stuck with but it’s not true at all. And I think if you look at your business, you’ve generated a ton of revenue from your podcasts. You’ve used that to create FindCollabs. FindCollabs targets software engineers which is great, it’s kind of a foothold. And if you get enough traffic and attention from software engineers, you can parlay that into perhaps getting musicians to start collaborating and other types of collaborations.
So, yeah, you’re a good example of the fact that that you don’t really have to start at the end. You could start at the beginning with something simpler or something easier and then work your way to where you ultimately want to be.
And that’s the biggest lesson from Amazon is the adjacencies, being able to move from one adjacency, in the case of Amazon the most humble business selling books on the internet has become just the beachhead from so many lateral points of expansion. That I think is the most interesting aspect of how Amazon has grown to become what it is today.
Let’s talk about making time to make these sort of lateral moves. You have pretty operationally-intensive business. I mean you are listing a new podcast every day of the week. You’ve got a lot of preparation that goes into it. You’ve got to record it; you’ve got to edit it. You’re also selling advertisements – enough advertisements – to generate $60 grand a month in revenue. I imagine that takes a lot of time as well. How do you as a founder structure the sort of nuts and bolts of your business to allow you the time to start something on the side?
Well first of all there’s definitely been a cost to just kind of working pretty hard on things and doing a lot of different things. You know, I have a vision for what I want to do and that vision like I don’t know of another way to get there other than to just put in a lot of hours. So, I put in a lot of hours.
That’s kind of – there’s not like secret sauce to Software Engineering Daily. That’s kind of why I’m pretty open about like sharing what I do. There’s just no secret sauce. I just put in a lot of hours. And so, the reps – you know, it’s like reps. Reps help. If you do more podcasts, you get better at them; if you do more podcasts, you have more ad slots to sell.
So, that’s kind of the thing is like – and as I’ve gotten into the habit of doing the reps, like the reps have gotten easier. And so, you know, as the reps get easier you start to find yourself with a little more time. You can start another business, you know? You can write a little more music. You can start another podcast. So, I would say that’s the way I’m scaling is just put in a lot of hours if you can.
What about growing your download numbers? There are a lot of people who start podcasts and the reason they quit is that it just doesn’t grow. The download numbers never really get beyond the low 10s, the low 100s, whereas with Software Engineering Daily, you’re getting some 20,000 downloads a day. How do you grow your podcast?
Well there have definitely been periods where we’ve stagnated and had just periods of just not growing of being flat and then, you know, the growth starts again. I don’t know what it is. I just – you have long streaks of shows where things are like mediocre and like the show doesn’t stand out. But then you occasionally have shows that really stand out. You have really good ones.
I don’t know. I wish I had a causal understanding of the growth of the show. You know, if I pulled back – the thing is like if I pulled back the zoom, on the Lipson Analytics – I use Lipson. If I pulled back the zoom it looks basically flat for the last year. I have to go to a different view and have the zoom where it’s like you can zoom out to the entire four years for it to actually look like an incline.
So the growth is very slow.
In the Indie Hackers podcast, it’s the same. I mean it grows pretty slowly, pretty steadily though, it’s consistent. And I’ve found that the most important thing is just to not miss epsiodes.
As long as I’m consistently putting out decent episodes, and I’m not missing a week, it continues to grow. It’s kind of hard to see the growth if you’re zoomed in too far but like you said, if you zoom out, you kind of see it.
There have been some other tricks too. Like having a guest on a show with a big audience can help growth the podcast, especially if that guest hasn’t been on a lot of other podcasts. If they’ve done like 15 podcasts in the last month, their audience probably doesn’t care if they Tween another one Butt yeah, mostly it’s just consistency.
Let’s talk about the early days for you since it seems that most of your growth seemed to happen back then. How did you get started? How did you get from no listeners to your first 100 or your first 1,000 listeners?
It was easier back in the day. You know, four years ago people were hungrier for podcasts than the number of podcasts that were available to sate their appetite.
For people like me, that’s still the case even today but there were so little quantity of episodes, especially in the realm of technical content that was fairly well-prepared for. So, it was just easier back then. I think it’s still pretty easy today to get started. The market is just soft, you know. It’s just soft. There’s not enough podcasts out there.
You spent a lot of time talking to other podcasters, Jeff. We were you into sort of a meeting of a minds a few weeks back with Mike Solana who does Founders Funds podcasts and Sonal Chokshi who runs – who’s the editor-in-chief at A16Z and who runs their podcasts operations as well.
What are some things you’ve learned from talking to other podcasters and from observing how other media operations work?
So, those are – those are two different things. Learning from individual podcasters, I will say I’ve learned more from listening to the podcasts than talking to them. And sometimes I will have conversations with the other podcasters where I will just say an observation from their – like something that I’ve noticed about listening to their podcast that I think they do distinctly well. And they will say yes, I have refined that technique. I’ve worked on it really, really hard.
You know, my Mike Solana from Founders Fund who was at that meeting – the Kabal pocast, just Kabal – he does this thing where most of his shows are very well produced. They’re the sliced together, from different interviews and then monologues from him. And then some of his shows are just interviews, just like an unedited interview. This is the same thing that Reid Hoffman with Masters of Scale where has the – the highly-edited Masters of Scale episodes then he’s done a couple of just unedited raw interviews, like the interview he did with Reed Hastings.
And you know, when I was talking to Mike about this, I was like I don’t know why you do the over-edited – not over-edited – I think in Reid Hoffman’s case it is over-edited, but in Mike Solana’s case I think it’s adequately edited. But to my mind, like, I guess this is just because I’m a power consumer and because I hate inbox zero, I would just rather people have higher output with less editing and just – you just don’t need the editing.
You just don’t need – I just think people want to hear the one-on-one conversation, this one-on-one podcast conversation format has so much depth and so much dynamism within it that just talking to people about that specific format is something I never get tired of. And there’s a lot of finesse to discuss.
Having one of these highly-produced, highly-edited shows just takes a ridiculous amount of time and planning. I mean if you’re just staring at a wav form trying to figure out when somebody said something , where to cut, how to rearrange things to make it more interesting, that’s going to take you five plus hours per hour of audio to do something like that.
Whereas the normal conversation, if you just sort of release it as it is, you can sort of churn through episodes. That’s sort of the magic behind what makes your show work. You’re releasing five episodes a week. You get a ton of downloads because you have so much content and I think that’s only possible if you aren’t really editing things too heavily.
Yeah, and I should add that I’m definitely not confident that I’m in the majority of this opinion of being – and like I love Mike Solana’s interviews. That’s part of the reasons I would rather listen to his long-form interviews. I would just prefer that because I like it so much.
But I know there are people who just love hard-core history for example and that’s like the most edited – it’s like super-edited. So, you know – and some people love Radio Lab which is just like also editing carnival. So, I don’t know different strokes.
Different strokes. Well, listen, Jeff, we’ve talked for a solid hour about podcasting so I think it’s a good place to wrap up. Why don’t we end by you telling listeners, especially the early-stage founders, the early-stage people who might be considering getting into podcasting or any sort of business. What’s your advice for them? What should they know before going into this?
Have a vision. Know what you want, pursue it and don’t give up. Put in the reps. Develop a style that is your own and prepare. Those things.
So, simply stated, great advice. Thank you so much for coming on the show, Jeff.
Thank you for having me, Courtland. I’m a huge fan of the podcast. I’m really glad that you started it and I am seriously an adherent listener.
I’m glad you helped me start it. I almost forgot. Can you tell listeners where they can go to get to FindCollabs and where they can go to listen to Software Engineering Daily?
Absolutely. So, you can go to FindCollabs.com to find collaborators for your projects, to post your projects. You can listen to Software Engineering Daily on Spotify or on your podcast player. Just search Software Engineering Daily and yeah, I hope you enjoy it.
If you enjoyed listening to this conversation and you want a really easy way to support the podcast, why don’t you head over to iTunes and leave us a quick rating or even a review? If you’re looking for an easy way to get there just go to ndhackers.com/review and that should open up iTunes on your computer.
I read pretty much all the reviews that you guys leave over there and it really helps other people to discover the show so your support is very much appreciated. In addition, if you are running your own Internet business or if that’s something you hope to do someday, you should join me and a whole bunch of other founders on the indiehackers.com website. It’s a great place to get feedback on pretty much any problem or question that you might have while running your business.
If you listen to the show, you know that I am a huge proponent of getting help from other founders rather than trying to build your business all by yourself, so you’ll see me on the forum, for sure, as well as more than a handful of some of the guests that I’ve had on the podcast.
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As always, thanks so much for listening. I’ll see you next time.
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