S1 EP 3: How to Never Run Out of Ideas for Your Content or Business with Jeremy Enns

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This week’s episode of The DollarSprout Podcast features Jeremy Enns, CEO of podcasting agency Counterweight Creative.

He and his team help with “podcast strategy & production for scrappy brands looking to punch above their weight” → I had to quote that line from their site directly because I love it so much.

Jeremy has many titles – audio engineer, podcast producer, CEO. But above all else, he’s a creative.

In today’s episode, Jeremy shares some of his biggest lessons and tips from over 10 years as a creator and 6+ years growing Counterweight Creative, including:

  • How to come up with an unlimited number of ideas (for your business, content, writing, or any creative endeavor)
  • How to stand out and make more money on Upwork
  • A surprisingly important trait required for success in podcasting, blogging, and business

Side Note: Jeremy was extremely transparent about the number in his business, which we always appreciate! The first ~15 minutes of today’s episode is about his revenue, profit, email list size, and other business metrics.

Links and resources:

Key Takeaways

Huge thanks to Jeremy for all the tips, tools, and behind-the-scenes information he shared in this conversation. I went back through the recording and wrote down, like, 10 key takeaways, but that seemed like too much, so I narrowed them down to 5.

Here are my key takeaways and some action items that you can take away from this episode.

1. Don’t underestimate the power of a small, engaged email list.

Jeremy made $20,000 in his first year of selling courses with an email list of just 1,500 people. He said that about 80% of his sales came directly from his email list, so that works out to $16,000.

If you thought you needed tens of thousands of subscribers to make good money with your online business, think again. You can have thousands of subscribers on your email list and not make any money from it.

I’ve seen this with other business owners that I’ve talked to and worked with. I even got to a point in my own business where I had over 6,000 subscribers and was getting NO SALES from my list because they weren’t the right subscribers. It’s not about how big of an email list you can build. It’s about building an engaged list of the right people. 

In our episode with Pete McPherson, we talked about having something to sell before you start creating content. This is the product-first approach. You don’t have to have your product or service built out, but you need to know what you’re gonna try to sell. Once you know what you’re selling, you can work backward to create your lead magnet/opt-in – the thing that gets people on your email list – and create content that leads subscribers to your paid offering.

So with your lead magnet, for example, think about a quick win you can give to your ideal customer that’s the precursor to your paid course, coaching program, etc. Then once you have the right people on your list, don’t forget to email them, keep them engaged, and provide value even when you’re not selling.

That was more than what Jeremy and I discussed on this episode, but if I were to go back and start over with my financial coaching business, this is how I would approach it. Not from the perspective of “How can I get people on my email list,” but from “How can I get the right people on my email list?”

2. It’s okay to “sell out.”

Jeremy studied audio engineering in school. When he first heard about podcast editing, he knew he was overqualified for the work.

He thought, “What would all my audio engineering friends think?” Would they think he was a sellout or look down on him for doing work that was “basic” compared to what he could be doing?

But he did it anyway.

By “selling out,” he was able to quit his job in just 6 months to work for his business and travel full time. So don’t be afraid to “sell out” or do work that you or other people might think is “beneath you,” because that work could just be your ticket to freedom.

In fact, Jeremy said that the reason he was so confident and able to make money so quickly is because he found work that he knew he was overqualified for. So if you’re looking to start a service-based business, consider starting with freelancing and offering services that you know you’re overqualified to do.

3. You can still make good money on freelancer marketplaces like Upwork or Fiverr.

But there are two key tips Jeremy suggested:

  • #1, like we just mentioned, look for work you’re overqualified for.
  • And #2, add your own personality. People who post gigs on freelance sites often get 200+ responses. When you’re messaging someone on Upwork or wherever, make sure the subject of your message is catchy so it captures their attention. Then add your own personality and flair and mention anything relevant to the listing that sets you apart from other bidders.

4. The thing that sets your content and business apart is unique and novel ideas. And you don’t get those by listening to or reading tactical-style content.

There’s nothing wrong with tactical, how-to content. In many cases, it can be part of a well-rounded content strategy. And when you’re early in your business, you probably should be consuming some of that. It gives you a vocabulary and a basis for building your business.

But at a certain point, you have all the information you need, and you just need to start creating and getting as much of your own ideas out there as possible.

Jeremy mentioned three things that have helped him come up with new and unique ideas and that he recommends to other creatives:

  1. First, find and consume content that makes you think in new and different ways, like creative, non-business books, podcasts, blogs, etc. For Jeremy, that’s content like Seth Godin’s podcast, Akimbo (which I also love, by the way).
  2. Second, keep a list of ideas, and add to that list every day. I love that Jeremy brought up this exercise from James Altucher which is to have a daily idea practice. Similar to a gratitude practice, like you may already have, every day, you write down 10 new ideas. Or you can do 3 or 5, whatever works for you. By doing this, you can train your brain to always be looking for new ideas, which means you can create an endless backlog of ideas, content, etc. Jeremy said he has over 1,000 topics on his own idea list. If it sounds intimidating to think of new ideas every day, keep in mind that an idea doesn’t have to be fully formed or actionable. As Jeremy said, it’s just something small that’s interesting or that you’re curious about. It can be an opinion, a thought on something you read, a controversial take on common practices in your industry – anything. Two things to keep in mind when choosing where to keep your idea collection: you want it to be consistent (all your ideas are in one place so you can easily see, sort, and find them when you need to) and accessible (so you can pull out your phone or laptop and add to it as soon as an idea comes to mind). I thought this was a great point because I usually keep my ideas in a Google spreadsheet, but it’s not the most accessible option, even with the Sheets app, so I think I’m going to try Jeremy’s method of using Notion instead.
  3. And the third and most important thing Jeremy mentioned that helps him come up with unique ideas: creating content. Jeremy says, “If you want to find your voice, differentiators, and perspective, you really just need to get as much content out there as possible. Creating that content, thinking through your ideas, that’s what’s going to help you find your voice and your unique perspective. And that, ultimately, is what sets you apart.”

For more thoughts on how to come up with unique and creative ideas, check out the key takeaways in our episode with Lexi Merritt.

5. You don’t have to be the best. You just have to keep going.

Today, it’s easier than ever to start a website, launch a podcast, or open a new business. And because of this, it can feel like, “What’s the point? The market is already oversaturated.”

BUT here’s the thing — even though a ton of people are jumping on the online business or content creator bandwagon, most of them quit too soon.

Jeremy mentioned this stat on the show: 90% of podcasts don’t make it past episode 3. And 90% of those that do don’t make it past episode 20.

And while I couldn’t find the stats on how many people quit blogging before they make any money, I’d venture to say it’s pretty high. Which means you exponentially increase your odds for success just by staying in the race and outpacing your competition.

Does that mean you just keep doing exactly what you’re doing now forever until you’re successful? No!

You’ll probably look back at that blog post or podcast or YouTube video a year from now and think, “Oof. That was awful.” But be consistent, learn how to create better content and improve as you go, and you’ll outpace the vast majority of people in your space.

Related Podcast: Is Blogging Dead? Here’s How Blogging Has Changed in the Last 7 Years

Episode Transcript (click to expand)

Note: This transcript was automatically generated and may include typos.


[00:00:16] Megan: Hey there. Thanks so much for being here on the dollar sprout podcast. Today’s guest is Jeremy ENS. Jeremy is the founder of podcasting agency, counterweight, creative, where he and his team helped their clients create a podcast that stands out, cuts through the clutter and turns casual listeners into brand evangelists.

But more importantly, or at least equally important as his role of CEO at counterweight creative. Jeremy is first and foremost, a creative himself. If you’re interested in learning how to turn your own creative energy into money, how to come up with an endless list of new ideas or the number one thing that you can do to get ahead and stay ahead as a creator, then you are going to love this.

Don’t forget to stick around to the end of the episode, to hear my key takeaways, my thoughts, and some action items that you can take away from this conversation. I hope you enjoy this episode, please. Welcome. Jeremy ends everybody.

Interview with Jeremy Enns

[00:01:19] Megan: All right. Hi, Jeremy. Thanks so much for being on the show today. Welcome to the dollar sprout podcast.

[00:01:28] Jeremy: Hey, Megan, I’m excited to be here. Thanks for having me on.

[00:01:31] Megan: Yeah so, to get started, would you mind to tell us a little bit about your business counterweight, creative and what you guys do?

[00:01:38] Jeremy: Yeah, so, um, of we creative is a podcast production and marketing agency. I started at two I’ll start, started out as a freelance podcast editor coming up on six years ago. I think the six year anniversary is coming up in three or four months, something like that. So getting close to that and since starting out as a freelancer who started hiring people on, and it didn’t really realize what I was building was called an agency at the time, I was just like, I’m feel like I’m making it all up on the fly, you know, reacting, putting fires out, just being very reactive and then kind of later realize like, oh, this is this established type of business model.

That w that was a real brainwave for me. So yeah, I’ve been doing that for six years and have recently in the. Two years started to expand more into the online education courses, teaching more consulting side of things as well.

[00:02:24] Megan: Yeah, that’s really exciting. What made you decide to branch into like the online courses in addition to your agency?

[00:02:31] Jeremy: Yeah. So for me, I guess, like, I’m like, I’m a creator at heart for sure. And I, I like building and running businesses as well. Like that’s something that I got into it. Really I started this business because I wanted to work online because I want it to be able to travel. And I happened to go to audio engineering school.

I wanted to work in the music industry and make records and all that kind of stuff. And that’s a hard industry to make it in these days, especially. And so kind of stopped doing that, set that aside. And a couple of years later, I’d gone on a big trip, spent a year traveling, just saved up and took the year off and came back and wanted to do more of that.

And kind of quickly realized learning about online businesses and listening to podcasts myself and realized that, oh, all these, you know, audio engineering skills crossed over into podcasting. So it was kind of just this convenient thing there. But for me, it’s always been like, even from the start, I was like, I want to be able to write, I want to make courses.

I want to do. I mean, at the start I wanted to do to create passive income streams. Now I know myself well enough that I’m never not going to be working on something. So it’s, I don’t care about like the passive part of it. I just like building things and marketing them. And so for, to me, that’s just where the fun is.

And so now kind of the. Got up to a point where it was systematized enough where I actually had, you know, 25 to 30 hours a week to actually spend on other stuff. And so that was where I was like, okay, I can finally get to work on these courses and do more writing and content creation and all that kind of stuff.

So that was kind of always something I was working towards, but for many years didn’t have the bandwidth to do.

[00:04:00] Megan: Yeah. Gotcha. Okay. So I definitely have some questions about your background and want to hear more about the story of your business. But before we get into that we send all of our guests a survey about what you’re willing to share. About your business on the show and really appreciate that you were open to being super transparent about the numbers and the behind the scenes of your business.

We always appreciate that our audience loves to see the behind the scenes. So do.

you mind if in sort of like a rapid fire style, we just go through some of those numbers.

[00:04:35] Jeremy: Yeah, let’s do.

[00:04:36] Megan: Okay, cool. So what’s your current business revenue?

[00:04:39] Jeremy: So I think last year let’s see last year was probably around 250 or two 75,000. This year will be less as I’ve kind of shifted all my focus away from the agency and more on to the kind of creator side of things. But the profit will actually probably be more this year. I would imagine by the time we get to the end

[00:04:58] Megan: oh yeah. Through adding courses and

your education. Yeah.

Cool. What percentage of that, if you know, off the top of your head is from your agency side of your business versus your courses?

[00:05:10] Jeremy: So last year, if we’re going from last year and let’s just, let’s just make it even at like 250,000, I think it was somewhere between there and 2 75. But I would last year, certainly that was the first year I launched the courses. So I probably made maybe 20,000 from the courses. And the rest of it from the agency this year will be more from the courses.

Not that much more, but maybe like 30,000 from the courses. And then the rest will, will be from the agency, which this year, I think it might be like 1 75 from the agency, something like that in revenue.

[00:05:43] Megan: that’s awesome. I feel like that’s a really good, you know, first year for your courses.

[00:05:49] Jeremy: Yeah. And yeah, it’s, it’s, it’s interesting. Like I, of course, like anyone had way, I know many course creators who make hundreds of thousands of dollars from their courses. And so I knew that wasn’t really realistic, but it’s still in your head. Like maybe it could happen. And so it’s been, I’ve do a cohort based course.

And so I’ve launched at four times run four cohorts of it and. What I’ve realized and what I’ve in talking to way more course creators is that probably you’re not going to find the version of the course that works. You’re gonna need to run it like six or seven times probably before things really start to gel.

And I feel like that after this fourth one, I’m like, oh, okay. I think I’m actually onto it now. And things are starting to come together. And so now it’s more about like building out a whole ecosystem. That’s more naturally leading people into it. So I kind of feel like the first two years having just been the experimentation and figuring out how to actually deliver the thing in the best way and as well as how to market it.

And so I think that’s something I wish I heard more people talk about at the start was like, it’s not just, you have the idea you make the course, you’re going to be successful. You have to like remake the course many times, a lot of times for it to like, get to be a thing that can be that

[00:06:51] Megan: Yeah. Interesting. Did most of your sales from your courses come from like your existing audience and email list? Or how did you market those in year one?

[00:07:03] Jeremy: Yeah. So the in year one, those were both I would say 80% of sales were from existing audience and email list. And then the other 20% with both of those two those were very like internal launches. Like I didn’t really know what I was doing at a bigger launch scale at that point. And it just all felt overwhelming.

So I was just marketing to my existing audience. And I also did a lot of cold outreach to people looking at podcasters and who, like, I had a bunch of criteria that I was like, okay, probably they’ve been doing it this long. They probably have this many like, reviews on on apple podcasts. You know, you can’t see download numbers or anything like that.

But I reached out to a bunch of people like that and I probably got a few customers that way, but not a ton, but at the start, like, you know, three customers, I think probably in I think I sold 19 and the first, the presale, the, the course wasn’t even created yet, but I think I got three of those people were through cold outreach.

So, I mean, I was, that makes a, it’s actually a kind of significant percentage of, of the 19. So it was definitely.

[00:08:01] Megan: Yeah, I’m so bad at rapid fire questions. I’m sorry. Everything I do is so slow. Okay. So I’m just thank you for sharing that. I’m going to keep going through these and try to go through them a little faster. Cause I did say rapid fire. Okay, so that was business revenue, all of that. What about your business profitable?

[00:08:19] Jeremy: Yeah. So that would be let’s see again, look at last year and that would probably be, and I’m kind of technically, it would be pretty low. If we’re not looking at paying myself as well, like on top of my salary, the profitability would probably be, I would say like 5% maybe, which is something that I think, yeah, I did not understand a lot about finances until the past couple of years and have now been kind of understanding where the benchmarks are and trying to work towards those with.

[00:08:50] Megan: yeah. Yeah. And I feel like, I don’t know what numbers, what typical numbers are for an agency, but yeah. I mean, that’s part of having a business is like learning how to do the business side of it and you know, the numbers that are important. So,

[00:09:05] Jeremy: they are agencies are notoriously low compared to other businesses, especially what I’ve learned from one of my coaches in the phase I’m in like years kind of like, I mean up until probably he was five or six, something like that, like it’s pretty lean. And then oftentimes you get through the other side and you can start increasing them.

But I know she had said like, yeah, if you’re at like 10% profitability, like you’re probably doing pretty good for where you’re at right now. And so I would say I’m between kind of, yeah. Five to 10, somewhere in there.

[00:09:31] Megan: Interesting. So what happens at like fear five or six or whatever you just said where like the profit margins increase for an agency specifically? Is it just, you get to a certain point and you can raise your prices?

[00:09:43] Jeremy: I think there’s probably lots of things. I think it takes a lot of people, a long time to get the systems in place in order to actually scale and get the team in place. And, and I think there’s like a compounding effect where you just have to kind of like take all these little incremental gains of like, you get a little bit more income.

So then you can like hire outsource a little bit more. And eventually you get to the point where you can actually hire someone who can handle a lot of the, either sales or maybe it’s client onboarding, which frees you as the founder up to do marketing. And then all of a sudden, like it just really accelerates.

So I haven’t hit that phase. And I don’t know that I will, because I may offload the agency to do the education stuff. Full-time, that’s kind of the goal right now, but that’s where I feel like I, if I wanted to, I feel like that’s kind of like would be an option. I am not necessarily interested in that though at this

[00:10:31] Megan: Yeah.

Okay. Very cool. So you mentioned your personal income paid by the business earlier, and that’s different from profit, obviously. So what is the salary, if you don’t mind to share that you get paid from your business?

[00:10:43] Jeremy: Yeah. I’d say it has ranged between 30 and 50,000 a year, which actually, and this year will be interesting because I think it will be probably, oh, it would be higher than that. I would imagine because the course is almost a hundred percent profit and there’s very few expenses to it. So that’ll be the interesting to, to just look at, at the end of the year as well.

So I’ve got like a couple of other products that are still just launching right now. So there could be a boost at the end of the year here, but yeah, I would say historically it’s, it’s been, I mean, pretty, pretty low considering how much. Revenue the business makes, which is I’ve also made, I think an important part to understand is that like I’ve really optimized for time.

And so I have built the business over the past few years where I only spend, you know, five to 10, maybe 15 hours a week on it so that I have time to do other stuff. So I could take on way more work that my team is doing right now and make a lot more personally, but I’ve chosen to like pay my expenses so that I can focus on building the next thing that I really want.

I would say over the past year, it’s like maybe eight hours a week is on the agency and everything else is on kind of content and course kind of stuff.

And and all


[00:11:52] Megan: Very cool. It sounds like you’ve really been able to optimize. And also if I’m not mistaken, you guys, you said you travel full-time right. So have you been strategic about where you guys travel to and where you live to make sure that.

you can keep your personal expenses low and spend more in the business so that you can optimize your time?

[00:12:11] Jeremy: That’s at times we’ve definitely done that. I don’t, I don’t think we’ve ever picked a place specifically. Like the only reason was that it was cheap. That’s definitely been a, an attractive reason to go somewhere, especially at a certain time. If we know that, you know, we don’t has my, my partner is also, she’s a freelancer and I mean, my business is very like a subscription business where our clients run a monthly plan and they just keep producing their shows, hers as much more classic freelance where, you know, it’s boom and Boston, you don’t always, you know, you do a huge project, then there’s nothing for three months or something like that.

So sometimes it’s like, okay, it would be nice to be, we can’t go here. It was probably more, that’s how we think about it, of like, we’d like to go here, but now it’s not the time to do that. So. Typically optimize more for time zone and just keeping it, you know, we, we don’t go to Asia or we haven’t together.

Since we started like working in traveling and we’ve kind of stayed in Europe and north and south America

[00:13:02] Megan: Gotcha. Very cool. Okay. So the last two rapid fire quote-unquote questions that I have for you are, if you don’t mind to share what your website traffic is like and your number of email subscribers.

[00:13:15] Jeremy: Yeah. So email subscribers are at around 1500 and the website traffic is let’s see, I would have to actually look this up. I would imagine it’s around like a thousand users, unique users a month, which I’m not, I need to like hire an SEO consultant because there was actually a lot more and I hit a huge drop that Google must’ve done some update earlier this year and it was.

Yeah, just a massive hit to it. And I’m just like, I’m not doing anything wrong here with SEO that I know of. I’m not doing any like black hat stuff, but I’ve been more focused on core stuff in marketing to like dig into that. Cause I know that could be a rabbit hole, but it feels like something that probably needs to be

[00:13:57] Megan: Gotcha. Well, thank you so much for sharing all of that. Yeah, just appreciate you being willing to be so transparent about all the numbers. So I want to take a step back and get back into what you started to touch on earlier, which is your story of how you got started with a podcast. In podcast production, how you started your agency and yeah.

What all of this looked like in the beginning for you? So you said you started out freelancing, is that correct?

[00:14:25] Jeremy: Yup. Yup. I actually, when I first started learning about online business I was looking to build a photography business. I wanted to, I was thinking like, you know, travel photography, something like that. I done shot some weddings and things like that when I was still living in Vancouver. And but so it was starting to blog and, and try to, you know, build an online business around photography.

And I was thinking courses and that kind of stuff. But I was doing that for about six months and I was listening to podcasts at my day, job landscaping. Like I listened to like 50 hours a week of podcasts all day everyday at work plus more in the off time. And I listened to it like two X speed and just all business podcasts, you know, online business stuff.

And so I had a lot of ideas coming in.

And at some point, listening to all these podcasts, something clicked. I was like, I think it was actually a friend of mine. I was listening to his show and he mentioned his podcast editor and something clicked. And I like new people edited podcasts, but I’d never really thought about it.

I kind of thought it was like beneath me, like going to school for this, working in a studio, all these things. I was like just a podcast editor. Like what would my other audio engineer friends think it feels like a sell, selling out or something like that. And so I kind of just ignored it. And then for some reason, something about how my friend mentioned his editor on the podcast, it just clicked.

And I was like, huh, it’s going to take a long time to build up a business and create courses and get that audience for that to allow me to travel. I can start editing podcasts today for people and get paid. From people and I could start traveling really quickly. And so I think I, I signed up for Upwork that day.

And within three days I got my first client and within six months I was equaling my day job or passing the day job income. And so I ended that and within two weeks of quitting the day job and going full-time on the business, I was on a flight to the UK where I spent the next four months or so.

[00:16:09] Megan: Wow. Yeah.

that’s very fast to get your first paying client in three days. And then in six months you were

able to go full time, essentially.

[00:16:20] Jeremy: Yeah. Yeah. I think it is fast. And I think when, when I think about that and what I th when I think about what probably holds a lot of people back, like I had so much confidence because I was so overqualified for the job. I was like, and I, I started off my rate low because I was like, well, I don’t have any portfolio or anything to do with this, but I did have a portfolio of, you know, music projects, which are way more complex and complicated than producing a podcast.

So I had some of that, but it wasn’t really relevant. But, you know, I just knew, like, this is so easy and like, I’m so much more qualified than almost everyone else on here. So like, I should be hired by people and they should want me to produce their show, which I don’t think I’m that confident in everything that I do.

But that was something where it was just so clear to me that there was this external validation of, like, I went to school for this. I’ve done all this work on this. That’s way harder than this. Like, this is a cakewalk kind of. And so I think that that’s one thing that helps. And I think then over. One of the things I learned over the next six months, really starting on Upwork, getting most of those clients, if not, all of them was just, I, this is, I guess, just classic marketing now.

And something that I teach for, for podcasters, anybody creating content is around differentiation. And I, like, I got zany and pretty wacky with my intro requests to people on Upwork, because in my mind I was like, they are probably getting 200 people responding to this. Like they’re not gonna read through all of them.

They need something to catch their eye immediately first sentence and be like, huh. And then like, that’s, it’s like the subject line of an email or an episode or blog, post title or anything like that. Like the goal is to catch attention and make people go like, wait, what? And like lean in and and read the rest of it.

And the rest, it was just normal and professional, so to speak, but it was still a lot of personality. And so that’s what I found. Like as soon as I started doing that, I also upped my rate around the same time. And so I think there’s something about like having a high rate and also. A little out there.

People think you, maybe they just think you’re like eccentric rather than just like an amateur. And so I have no way of proving any of that, but that was my experience. And I’ve told other people to do that as well. And I think they’ve had better results as well from what I’ve heard. So I that’s, that’s my big advice for, for standing out on Upwork is that I think, I think you can do it.

There’s it’s of course crowded, but I think you just have to like, understand what is the person who’s putting the job listing out there? Like what’s their experience? How many listings are they responses? Are they getting and what can you do to kind of stand

[00:18:42] Megan: Yeah. Interesting. So if you were just starting your business today do you still think that Upwork or Fiverr in these freelance marketplaces are like, is that where you would start and recommend that somebody else start? If they want to begin with freelancing?

[00:18:57] Jeremy: I think I would I’ve thought about this before and I think it that’s to me still feels like. You have control, which I think is important. I think, I think you also like long-term building long-term like building your business. I think it’s important to have content and ways for people to come back to you, but those things aren’t going to pay dividends for a long time.

Like, I think it took me a year of writing blog posts before the first client ever came in through that and like had read most of them. And so like that, and I didn’t start writing blog posts immediately that took me a year to even start that. So it was two years into the business before I had any kind of inbound other than through referrals.

And so yeah, if I was starting today, I would probably go either. Cold outreach or through, although I did that too, and that was, I think I had sent like 250 emails before I got my first client out of that. That was a lot of work. It did result in a client who ended up staying with me for three years, but Upwork, I got way more and and some great clients, I didn’t have a single negative experience on Upwork.

With, with anyone who’s like a jerk or didn’t pay or anything like that. So I think if you kind of position yourself in the right way, there are tons of, like, I know tons of people who hire on Upwork who are great clients and like they run great businesses. And so like there’s certainly on there not everyone is a jerker is, is really cheap or anything like that.

[00:20:15] Megan: Yeah. I want to talk about two things that you mentioned when you were kind of going through how you got started here. The first is, you said earlier that.

you were listening to like 50 hours of business podcasts a week when you first started out. Are there any podcasts that stood out to you and any that you still listen to today?

[00:20:34] Jeremy: I listened to the, so the first one I ever listened to the first one I discovered, I like didn’t know anything about podcasts at the time. And I had started this new job and I, we were allowed to listen to stuff at work. And so I thought, oh, I’d listened to audio books before. Maybe I’ll do that. And then I thought like, oh, I’ve heard about these podcasts things.

I wonder what’s out there. And I didn’t know anything about online business that like, that was a term digital nomads. Like I didn’t, I was trying to do these things that I didn’t know. There were phrases for kind of like, I guess there’s a theme kind of like I was building an agency that I didn’t know is called an agency.

So I think I went home and I looked on, on iTunes at the time and I think I looked up like creative business or something like that. And the first show I discovered was called creative warriors and the host was Jeffrey Shaw. And I think he, I have not, haven’t listened to that in five years probably, but that’s the one that he’s, I know he still does it.

I look it up every so often it may have changed names, but I listened to that one for a long time. And then both smart, passive income with pat Flynn and online marketing made easy, made simple with Amy Porterfield. I think those were the two that I really got into. I listened to entrepreneurial on fire for awhile, but wasn’t really, it just kind of all gets the same, the daily interviews.

You can just hear the same stuff over and over again. Yeah. Th so I would say pat Flynn’s was really the one that I stuck with the longest, and there was a few others here and there, but no today I don’t really, I only really listened to three podcasts now with any regularity. And the one that kind of has to do with business, I suppose, is Seth Godin’s akimbo

podcast, which is my favorite show.

Yeah. And it’s, it’s pretty like oblique, like in, in terms of like, it’s not actionable, it’s like philosophical and like makes you think differently about things, which is, I feel like is important now. I don’t really consume any tactical stuff that much anymore. And so, yeah, now, now I’m just more looking for, I guess, like inspiration or like, I guess I want to have my perspective changed in some way in, in the content I listened

[00:22:27] Megan: Mm. Yeah, that makes a lot of sense. I I also used to listen to a lot of like tactical style podcasts and at a certain point it’s just. It’s just too much it’s information overload. So I think it was great for me when I started out. There was just so much that I didn’t know. And so it gave me the vocabulary, like you mentioned earlier and also ideas on just where to.

start, but then once you get past a certain point, Yeah.

It’s like a lot of information. And especially if you listen to a lot of information on things that you’re not ready to take action on immediately, and then it’s just sitting in the back of your brain. And for me, I found that like, it could cause like feelings of guilt, you know, because you have all this stuff

in your brain and Yeah.

you’re just, you know, you’re not going to do it, but you feel like, should I do all this, but I just don’t have the time and it’s not a priority. yeah. So.

[00:23:23] Jeremy: Yeah. I had the exact same experience and for me it was like, once everything started sounding the same and you just heard the same things again and again, and again, I felt like, okay, either I’ve got to. Conclusions I can draw from this. The first one is that this is all just generic stuff. That isn’t actually true.

And it doesn’t work because I’m like, I think I’m trying it, but it’s not working. Or I can say like, oh, this is all true because everybody says it and I’m just not committing to it enough. And I need to stop listening to this. I already know, I’ve heard all this a thousand times from a thousand different people, it’s time to just do the work.

And so I think that was where I was like, okay, I don’t need to listen to more of this. I’ll listen to other stuff. That’s more maybe just general knowledge building. That’s not business, that’s just storytelling or whatever perspective, shifting interesting content. And just like in the business, I’m not adding to my to-do list anymore.

It’s just like, I’ve got a long enough to do list. I can’t even get through it in my lifetime already. Like probably I should just start doing those most important things.

[00:24:18] Megan: Yeah.


And I also find that like creatively, I get so many more ideas when I listen to podcasts like Seth Godin’s akimbo, you know, and I, I feel like it gives my brain space to think for itself. And also those perspective shifts that you were talking about just they spark new, new ideas and new ways of thinking that yeah.

Are just more inspiring than like here’s how to do Facebook ads or here’s how to market your blog, you know?

[00:24:47] Jeremy: Yep. Well, yeah. And so I think that’s, that’s, I think you’ve hit on like exactly the key that I think I’ve ignored for many years until like this year, I feel like I’ve leaned into it. And I think a lot of people never get past, this is the thing that’s going to set you apart. That’s going to make people that’s going to grow your audience or, or in your business.

And all this stuff is not like, okay, if you’re a freelancer, maybe it’s how well you can do the job. But if you’re creating content and want to be known as someone like a thought leader, something like that. The thing that will get you, there is ideas and like unique and novel ideas, and you don’t get those listening to tactical podcasts because then you’re just like, oh, I can just re rehash this in my own way.

And where what’s you look at anybody who has a big audience who really stands out, they think differently from other people and their ideas are unique to them and people may be copying them, but they kind of like came up with this thing that is no one else is really doing. And so I think once I kind of realized that I was like, oh yeah, I, it is actually detrimental to me at this point to keep listening to more tactics and things.

And I need to be like the, the thing that’s going to get me to the next level is coming up with unique ideas. And so I just need to like open my kind of, or broaden my spectrum of like what I’m consuming and allow those kinds of connections to happen and unique ideas come out of those.

[00:25:57] Megan: Yeah.

I feel like, so that kind of touches on another thing that I wanted to talk to you about, which is that I was reading or looking at a survey recently, specifically about podcasts and it was done in 2019 by discover pods and the stats that they have are that 30% over 30% of podcasts, don’t make it past their first year and over 60% quit before year three.

And I feel like part of that, you know, Could be exactly tied to what you’re talking about is like not having enough unique ideas, rehashing the same old content that’s already out there. But what are, like, what are your thoughts on that? Why do you think it is that so many podcasts don’t make it past the first year or three years?

And what can someone do to set themselves apart and set themselves up for success.

[00:26:50] Jeremy: I’ve heard more recent stats that are even worse than that. And cause I think a lot of people started shows in the pandemic because what the most recent stats I’ve heard is that 90% of shows don’t make it past episode three. I think 90% of people who start don’t make it past episode three and then a further 90% of those who make it past that don’t make it past episode 20.

And so you just have this tiny percentage of shows that, and even those there’s 3 million shows, maybe 200,000 of those or something like that are actually active. And which is kind of when you’re looking at it from a competition standpoint, it’s like, oh, there’s actually way less competition out there.

And all I need to do to make it into the top, like few percent of podcasts is get past episode 20. So that’s kind of an interesting way to think about it. would say like when it comes to why people quit. I think the biggest thing is that it’s just so much more work than anybody thinks going in. And I even started a show last last fall around this time, a little bit earlier than this, and having produced shows for five years for other people knowing how much work goes into it.

I still, I mean, I opted for a really ambitious show with like music and sound design and like narrative breaks and stuff like that, which even though it was like a kind of standard interview show, but it was a more highly produced version. And I ended up ending it after 30 episodes. Cause I was just like, oh, I cannot, this is taking 20 hours a week and I don’t have 20 hours a week to put into this podcast.

And so it was you, you, of course you can do it with less time than that. But I think to produce a good show, like it just does take time and I already spend probably 10 hours a week on my newsletter and it was kind of like, I, the newsletters, the thing that like really gives me life and is where all my ideas.

Come from and through and where they get sorted out. And so the podcast was this like tactical strategic thing that was like, probably would have worked, but I just didn’t love it enough to put that kind of time and effort into it. And I didn’t love it as much as the newsletter. And so I think that that’s the big thing is like, I guess for one people underestimate how much effort it is, they underestimate how long it will take to get results.

And like, usually I tell people like, if you’re not willing to do a show for two years, like just don’t start. Like you should go going in. You should be like, yeah, I would do this for two years. I would do this for five years. I would just do this indefinitely regardless of, you know, the results. I think that’s a good place to start from.

The show is like doing something that is going to be a win for you, even if you never build up, you know, a thousand listeners or 10,000 listeners or whatever it is. That’s kind of how I feel about my newsletter. It’s like, if nobody read it, I would still get so much value out of writing it that it would be worth doing anyway.

And so I think that’s, that’s a hard thing to find that, and I think. This ties into, like, when we’re talking about coming up with unique ideas as well, you’re not just going to start creating something and have that. Like before I started my newsletter, before I started the podcast, I started doing a daily writing practice, actually inspired by Seth Goden, among many other people who I know do that at the start of 2020.

And I kept that up for, I think I wrote and published a daily blog post for nine months or something like that, and then took a break. And then I went back to daily and when I took a break, I was doing the weekly newsletter. And then did another kind of stretch of, of daily writing. But I feel like after a year of writing daily or mostly most of your writing daily.

Everything just like leveled up in my life. Like, I felt so much more confident. I felt like I wrote a lot of those were about podcasting. A lot of them were about other marketing ideas. A lot of them were just sorting through whatever, whatever was in my brain. And I realized like, oh, when, when I get on a consulting call with a client and they have a question, it’s easy for me to answer.

And I go in with confidence. I’m like, I’ve already written about all of this. Like I know exactly what to say. I can articulate it well. And I feel like that really came through in helping people get results and having a better experience working with me. And then really like for my course that I created, I wrote it all out as blog posts.

Like not intentionally, but really that’s what I did. Kind of unintentionally, I suppose. And then it came time to like build the course and I was like, oh, I already have all the content here. It’s just organizing it in maybe a little bit different way, recording it for video. So I think that, yeah, there’s something about.

Your show is not going to be successful early on, especially if you don’t have a long history of creating things. And so like putting in the work and understanding like, okay, this is going to be a grind for a while. And I have to figure out what I want to say and like what my perspective is and what I have to offer that actually is different from what’s out there.

And it’s, it’s something that like, yeah, it’s, I’m a huge, like strategizer going in. I want to plan and know everything before starting anything. And I’ve kind of realized. Producing a lot more work that that’s a big inhibitor. And I think for some projects, that’s a, a good way to go about it. Like if someone were hiring me to do something, I would want to go through all that strategy with them.

So they’re not paying me to just figure out what their voices for months and months and months, like that’s not worth it for them. I don’t think. So I think there’s regardless depending on the expectations, that might be a different approach, but I think if you’re like trying to find your differentiators and your voice and all of that stuff, it’s just like get as much out there as possible.

And you know, some that you’re probably going to do another project later on that maybe you, you do a podcast for a year. That’s like, that was just the podcast that needed to get you to the next podcast that you’re going to do. That’s actually going to be, you know, more focused and more successful.

[00:31:55] Megan: yeah, so, so correct me if I’m wrong, is this writing practice, this daily writing practice that you have, this has been the main thing that’s helped you come up with those ideas, those like thought leadership ideas of things that like set you apart and like new creative content that you can put out into the world.

That’s not necessarily been said by anybody else.

[00:32:20] Jeremy: Yeah. And I think that, like, I’ve heard this before for, well, a lot of things, I know, gratitude. This is often a common thing of like, if you set the intention of writing down three things, to be grateful for each day, you start noticing things to be grateful for it. Because you know, at the end of the day, you’ve made a commitment to yourself.

Like I got to write three things down. So your brain is like, we got to find three things in the date in order to write them down at the end. And so the same with, if, you know, you have to write a blog post tomorrow, you, your brain starts like every, I know the first 20 probably that I wrote I every day I was like, what am I going to write about?

I got nothing. And all of a sudden, slowly over time you keep doing it. And then your brain starts understanding like, oh, I need to build up a backlog of ideas so that, you know, when it comes time to sit down and write in the morning, I’ve got 20 things to choose from. And I know I keep these all in a database.

In a, in notion. And I looked at that like from the start of the year, I don’t, I didn’t have it in there last year, but I think in the first six months of the year, I looked at like, how many listings are in my idea’s database here? And there was over a thousand and, you know, I wrote about maybe 70 of them.

And most of the thousand were terrible. Like I’ll never write about those. And they, they weren’t, I look back on them. I was like, what even is this? I don’t, I don’t even know what that is or what I was thinking, or it’s just like nothing worth writing about, but I think once you start building that habit and it’s, it’s kind of, I think it starts with making the commitment to write the next day, your brain, there’s a bit of a lag period, but then it catches up.

It’s like, oh, if we’re doing this, we better come up with ideas and you just start finding them everywhere. And that’s, I think when things get fun, when you like, have so much, so many ideas that you can’t actually get to all of them, and then it’s like becomes the really interesting ones

that you, you end up working on.

[00:33:55] Megan: Yeah. So what is this writing process look like for you? Is it like a stream of consciousness, a morning pages style thing, or what’s your process?

[00:34:06] Jeremy: Yeah. So at this point, so this point I still write every day, but it’s all just part of the newsletter at the end of the week. And even back then, like, it wasn’t, it was never stream of consciousness. It was always like a round an idea. And usually it was business or marketing or podcasting related.

And so anyone who’s read, having been influenced a lot by, by Seth Goden, like that kind of style, often of short for anyone who’s read his blog, he has done a daily blog for like 7,000 posts or something like that for many, many years. Yeah, probably these posts, some of them would have been like a thousand, 1500 words long.

Many of them were like a couple hundred, but it was just. I, I would, oftentimes it would be like something I was thinking about that morning as I would like walk to a coffee shop or something like that. A lot of times it would be like, I’d sit down and be like, what am I going to write about? And like, look at the list of ideas I had there and be like, are any of these interesting to me this morning?

And you know, one would jump out. And I guess the interesting part of it is that usually the ideas were like a single sentence. And so it, and so usually I didn’t really know where, what was going to come out of it. And so there would be something that I’d be like, huh? Yeah. That’s an interesting thing. So for me writing and a lot of people who have this kind of practice say the exact same thing, which is that like really writing is not just like dictating what you already know.

It’s like finding out what you know and what you think. And so there’s this idea that catches your eye and you’re like, huh, there’s something interesting there. I wonder, I don’t really know what it is. But then in sitting down to write, it’s actually like the physical process of thinking through something and figuring out what you do think about it.

And so I know that’s like, I feel like I have one. Stronger or more kind of my opinions are based on more of a foundation because I’ve actually thought through it now. And I’m like, oh, I think this thing, why do I think this? What is, how can I flush this out? And like talk through right through, you know, whatever’s going on beneath the surface in my brain.

And so I think that that’s been like that leads to competence and I think more confidence leads to more ambitious projects and leads to more success. And so I think it’s just this like virtuous cycle that kind of kicks off by kind of being prolific

[00:36:05] Megan: Yeah.

[00:36:05] Jeremy: whatever you’re creating.

[00:36:06] Megan: Yeah. Okay. So it sounds like in order to set your podcast up for success, you need to accept that it’s going to take more work than you think, and also figure out the ideas and the thoughts and the opinions that are going to set you apart from the content that’s already out there instead of just rehashing tactics and strategies.

[00:36:34] Jeremy: Yeah, the other thing I would add in there is also with so much more competition. Like we said, a lot of those shows that start don’t end up continuing to be produced, but there’s still a lot of competition and I think. A lot of times, like we copy this is I think the next phase of podcasting where there’s now another hurdle to, to kind of hurdle over, I suppose.

Is that like the interview show, especially in like the business or content kind of like an Infor informative content kind of world is just like a standard interview show. I’m going to start an interview show doing this, interviewing these people who all know this thing that is so played out in almost every niche imaginable that it’s really hard to stand out, no matter how good of an interviewer you are.

And so I think one of the things that’s necessary in order to stand out. It’s coming up with what I call a kind of unique show concept. And so the concept is really the combination of the content you produce and the way in which you deliver it. And so if it’s just like, you’re starting a show on business and it’s interview with successful business owners, like that’s been done a lot in, it’s hard to stand out that way.

Or we could say creators as well, and maybe we should go with creators because I have an example for this. But a friend of mine, J a Kenzo who everybody should follow. If you’re interested in podcasting as well and content creation he produced a show for I don’t know if anybody, any course creators out there, probably know the company podia, which is a course hosting platform.

And they, that’s where I host my courses. And then I think it, this was for them. I’ve heard him tell this story and I’m pretty sure it was podia, but they were like, okay, we want to create a podcast, helping creators be more. That would be the same end goal as anyone creating a interview show for creators, that’s kind of, you want to help creators be more successful, learn how to run their businesses, whatever.

But the concept of the show was that each interview is still an interview show, but each interview was centered around the the creator who they had on the guest talking through one project, you know, the project that was most successful, full for them. And so of course, all the other stuff about their backstory comes out in there.

You talk more broadly about it, but there’s this central hub that each kind of show is anchored in. That makes it interesting. And you hear that and you’re like, that’s not just a show interviewing creators. It’s like, oh, a show about the most successful project of these creatives careers. And every interview is centered on that.

And it’s like, oh, that’s, that’s more interesting than just a general interview show. And you can kind of understand a little bit about what you’re going to get from it. And of course you want to make your own most successful creative project. And you want to hear about like, oh, so what was the lead up to this?

How did they come up with the idea? How did they, you know, iterate on that? What were the results. And so that’s kind of like a more unique show concept than just an interview. And so I think thinking about that, which again can be hard and it’s not something you’re just going to think of immediately is going to be a thing that like, I think you want to get to the point where when somebody hears it, even if they’re not in your target audience, they’re like, huh, that’s kind of interesting.

The, the other example I’ll give that as super clear for this is the YouTube show hot ones. And so if anybody’s watched this it’s I can’t remember the host name, but he. He has a celebrity guest on and they eat five hot wings. They’re progressively hotter, hot wings, or maybe it’s even more than five, but the questions get hotter with each wing as well.

And more kind of like vulnerable. And so this is, this is a classic, like kind of a concept where it’s not just, you know, Oprah talking with, you know, whoever she’s having on just a little interview here, there’s this whole other element that brings into it. That is unique and engaging. You hear that and you’re like, nobody else can create that show because like, it would just be clearly be a copy of this one.

And it’s, it’s interesting in many different ways, other than just the questions that are come out of it, even though he is a fantastic interviewer as

[00:40:00] Megan: Yeah, that is interesting. Yeah, I think that’s, that’s a great woof stutter. I think that that’s so great. Kind of roadmap you said. So the concept of your show, but also the way that you deliver it.

[00:40:15] Jeremy: And well, yeah, and I would say the concept is like that combination of topic and delivery. Or the, yup. And so, yeah, and just the last thing on that, like the first step I think is just start paying attention to any media and you just start seeing concepts show up like these central themes that tie everything, everything kind of circles around that in a way.

And once you start noticing them, then it’s a lot easier to think of like, oh, I see how these work. And I’m starting to have ideas of how I could create something like that as well.

Slow Round Questions

[00:40:41] Megan: Getting into the next segment of our show, it’s called the slow round. Definitely took this from Mike Birbiglia. I don’t know if you know who Mike Birbiglia is. He is my favorite comedian. I will bring him up on every single episode if I get the chance just to,

[00:40:59] Jeremy: It’s like me and Seth Goden,

[00:41:00] Megan: yeah.

Every single chance I get to bring up Mike Birbiglia, I will take it. So everyone go watch. My girlfriend’s boyfriend on Netflix. Okay. So slow round is the opposite of a rapid fire. So we have a list of questions that we like to ask our guests and we let our guests choose their favorite questions from this list.

And instead of, you know, rapid fire answering quickly, you can take your time. Like I said, everything I do is slow. So take your time. We like slow

[00:41:33] Jeremy: as we heard everything I do is slow as well. Clearly we’re, we’re two, two peas in a pod. They’re given our rapid fire round earlier.

[00:41:42] Megan: Yeah. Okay. So, three questions for you today in our slow round. So the first one is in the last five years, what new belief, behavior or habit has most improved your life and or business?

[00:41:54] Jeremy: So, okay. So this, the first one we actually kind of already talked about, which is the daily writing. And I think that I feel like things have so significantly accelerated for me on a personal level, as well as a professional level, since I started writing daily. The second thing is kind of ties into that actually, and it has to do with, I guess it’s kind of like, it relates to idea generation, which, which of course ties into the writing, but we all need ideas for everything we do.

And what I found is I don’t, I feel like I need to come up with a name for this of this concept, but to me, I just think about it as like, you need a place to put things. And so we’re all, you probably don’t realize it, but we’re all having tons of ideas. Every single day. And I know one of the things anyone, I don’t know if anyone’s aware of James ,

but he

he’s been on a lot of podcasts yet.

He has his own and he’s written books, but he has this idea of coming up with 10 ideas a day. And I remember he was one of the people I first started listening to when I was listening to business podcasts. And I was so intimidated by this idea. I was like, how could you ever come up with 10 ideas a day?

And of course I was thinking, these are like 10 fully formed business ideas that like, and now I know that’s not what an idea is. An idea is something little that catches your eye, that you’re interested in, that you can explore further maybe, or you can just ignore it forever, but we’re all having these ideas.

And so I think the first thing is like lower your bar of like what counts as an idea. Just look for things that are interesting, where you’re curious about. I think we don’t realize them because it’s almost like this. It is very similar to meditation where, you know, we’re all having these thoughts, but meditating is about noticing the thoughts and that’s the same thing goes for noticing the ideas.

And so there’s this element of mindfulness first noticing them, but then putting them somewhere because otherwise they’re gone. Like you everybody’s probably had that thing where you like, have an idea in bed. You’re like, oh, I remember this in the morning and you don’t write it down and then you never remember it again.

And you just like, I had something that was so perfect and it’s gone. And so for me, I use a tool called notion. I don’t know if anybody is aware of this. It’s kind of, I don’t really know how to talk about it. It’s kind of like a blank slate of software that you can really build into anything you want and you can kind of build.

Really basic apps in a way, but it’s also, I use it to just like for word processing as well, but I have a, a database in notion. That’s just my idea collection database, and I just dump every stupid idea. Good idea. Everything just goes in there so that it’s all in one place. And I know whenever I need to look through my ideas, I can just go through there and then I can go back through and I can rate them, or I can assign them different tags for like, oh, this is about podcasting.

This is about marketing. This is about whatever else. And so I can filter them and sort them and look through my old ideas and just see them there. And so I think for one capturing. Capturing your ideas feel frees up so much mental space where you’re trying to hold all these things in your brain. And so there’s, I think a lot of benefit to just offloading as much stuff that you don’t actually need to remember in your day to day into somewhere else where you can easily go and find it later.

But so this idea of where to put things, I was thinking about this the other day, and I haven’t written about it yet, but I wrote down a few notes and I had three things that were important for this. And I don’t know if I can remember them now, but the one I’ll try and talk through them here. So the one was that it’s like consistent so that you always put things in the same place.

You don’t have three different notebooks where you are collecting ideas in different places. Like everything needs to go into one place. The second thing was that it’s accessible. And so for me, like I have a, on my, so I have I have the notion app, but I also have a Crappy on, on mobile. And so I just have a link on my phone homepage, which has almost nothing on it.

It’s just like, there’s like three, three apps and two links to notion pages that if I click it on my phone’s home screen, it directly goes into my idea capture bucket. And so it’s like, I can, I always have this on me. And I also always have it open on my computer. Like it’s always in a tab right there, easily accessible.

And so like, it’s the same place I always put things. And then it’s, it’s just always accessible to me. I don’t need to like reach for anything, look for a panning thing. I’m like wherever I am in the world, like I can capture an idea when I have it there. And so those were two of the, the three things.

And then I can’t remember what the third one was, but I think those two are a good enough place to start. And whenever I end up writing the article on that, then the third one will be illuminated. It’ll save that one for, for anyone who wants to subscribe and find that at some indeterminate point in the


[00:46:15] Megan: If that article is out, when we publish this episode, we’ll definitely include it in the show notes so that people can reference that.

But Yeah I agree, great place to start consistent and accessible. Awesome. Second slow round question is when you feel overwhelmed or unfocused or you’ve lost your focus temporarily, what do you do?

[00:46:36] Jeremy: so this okay, so you, and microbic you me and Seth Goden and also notion which I’m going to talk about. Again, these are the things I will bring up. Every, every time I talked to anyone that got to bring them up and so notion what I’ve also done in there is essentially made a list of like all these kind of practices that it’s like, okay.

Each, each one has a they’re in columns essentially. And so it’s like, when I want to feel this, or when I am feeling this, like, here’s how I can undo that or get out of that. And so a lot of times, for me, like going for a walk is one of those things. And so for, for unfocused, like definitely I think. Going for a walk.

That is a huge one, both for coming up. But for me, walking is like the cure all for everything. If I want to have ideas, if I want to be inspired, motivated, get my focus back. It’s like go for a 20 minute walk or even a 10 minute walk, get outside and come back and I feel way better. So I would say like, that’s, that’s my go-to other things that I feel are on that with unfocused, one of the things I’ll do is I’ll just set a timer.

I have a timer in my, on my Mac book. Some the toolbar at the top, and I can’t remember what the app is called, but I’ll just set that and say like, okay, I know I’m procrastinating on this thing. And so I’m just going to set like 10 minutes. I’m going to put it in. And as soon as I start the timer, I’m like, okay, it’s just, now we’re just doing this.

And I also do that. Like I track all my time using toggle. And so that’s another one that I found, like if I, if I go into toggle and I say like, okay, I’m doing email now. And I click start on that. I want. I’m kind of like a data nerd, I suppose. So I want my listings to actually be accurate to what I’m doing.

So for me, I’m like the timer’s running. I better be doing that because otherwise I need to change it and to whatever else I’m doing, like scrolling on Twitter or something

like that. So I would say that those are two of the big ones for me going for a walk and then just like setting a timer, especially when it’s something I don’t want to do and being like, okay, we’re just doing a sprint right now, 10 minutes, 20 minutes, whatever.

And I’m just going to get it done. And so those are the big ones.

[00:48:28] Megan: That’s funny. Yeah.

I feel the same way. I also use Toggl to track my time and I used to

just do it when I was doing like free Lance work, you know, for clients. But now I do it for everything that I do, even if it’s not freelance, if it’s like working. We’re on my business. I still track my time and Yeah, it’s very true for me also that if I have a timer running, my brain is like, all right, you got to do the thing.



[00:48:54] Jeremy: Yeah, I think, I think that the time-tracking is like, everyone should do it. And it takes a bit of work maybe when you first setting it up. But like, if you ever want to hire someone else, like, then you have this whole list of like, okay, where am I spending the most time? If I could hire one person, what would free up the most of my time?

Or like, and the one of my coaches at one time, she got me started doing this. And then it’s like, go through your weekly timeless thing and label everything. You know, red, yellow, green, red is like things that drain your energy. Yellow is like, you know, neither here nor there green are things that give you energy, look to offload as many of those red things as you can.

Because a lot of times they’re not even complex tasks. They’re just things that are like dull and boring and that are actually easy to outsource. So there’s a lot of benefits to tracking your time.

[00:49:35] Megan: Yeah. It can be a tricky habit to get into, but I’m at the point now where if I open my browser, the first place I go is toggle. So, and I’m

[00:49:44] Jeremy: Yeah. And my default, when I open Chrome, that’s one of the tabs that like by default is the first one that

opens up.

[00:49:49] Megan: yeah. And I, I got into the habit being somebody who like, I am typically very flowy. I like to go very slow. I don’t love tracking time as a concept, but yeah, I it’s been one of the best things for productivity. Okay. So last question. How has a failure or an apparent failure set you up.

for a later success in your business?

And do you have a favorite failure? They could be one in the same.

[00:50:17] Jeremy: oh, favorite failure. So I think let’s see, I think the, I did a, I created, and this was late 2018, early 2019. I think I created a bundle sale for podcasters. And so I had some friends who had done this in the travel space. And another friend who had done this with a belly dance bundle, where it was essentially a collection of products that, you know, you didn’t create, you were just facilitating, bringing all these people together.

And so I think I had like 25 products and the, it was a $300 product. But the value of if you bought each of those things, individually would have been $3,000 or something like that, 4,000. And so it was a great deal. And I was like, this is the perfect thing for podcasters. I know this model works because these two friends have both made, well, the one friends, they had done it for many years and made like hundreds of thousands of dollars.

Every time they did it every year. And the other one in the belly dance space, she made, I think like 30 or $40,000 from doing it each year. And I was like, This is like, this could be, this could be it, this could be my whole business going forward. And so I spent months putting this together and I mean, I had them, like, I could ask them all the questions.

I knew everything about the setup, the technical side of things, and had a bunch of affiliates. And essentially how these bundle sales work actually, I should say is all the people who contribute are also affiliates for it. So they are sharing it with their audiences. And so I didn’t have really any audience of my own at that point, maybe a couple of hundred people but was able to grow quite a bit through that and for them pushing attention to it.

But it, it did not end up working out so well. And so I was certain, like I had the website was like, great. I had hired my girlfriend, who’s a web designer to put together this great website. It was like, so slick. And I loved the design. I thought the product was amazing. And ultimately it ended up losing like $10,000 or something like that.

And it got you know, maybe like 30 sales or something like that. Most of that was paid to my girlfriend for the web design, which ended up just taking longer. So that was kind of like, okay. That it like stayed within our circle. But then I also hired someone to do Facebook ads. Cause I didn’t know anything about it and the, the ad cost and it just, yeah, it just flopped.

And I think in the years that have followed, I’ve been able to identify maybe some of the, just little things. Like, I don’t think there was one big reason it failed. I think there’s just a collection of tiny little things that added up that it didn’t really work. And there’s actually another company that does it now, a similar thing.

They charge $50 for it when they do it and I’ve actually contributed my own products to it. And I think that one does really well. And so I think, yeah, probably there was something about. In some niches, like both my friends who did it charged a lot more for it. And I was like, ah, $300 like that it, the value is there it’s 90% off or something like that.

People will be all over this. But I think it was potentially too overwhelming. There was too little focus on like what you, what you’re actually getting for this. I think it’s a different niche where people have different types of goals versus those other spaces. Although, I mean, belly dancing seems like an interesting one.

It doesn’t feel like a super high pain point or anything like that, that it’s targeting. But so that, yeah, that one was the big one where I think, you know, people talk all the time about failure and I always get annoyed that people don’t talk about. Like what it’s actually like. I think. Public failure like that, where, like, I, I think I was gun shy for at least a year and a half of doing anything else, creative, like just no appetite to produce anything other than like blog posts or whatever, but it was like legitimately painful.

Like I, the only thing I can think of it as kind of like getting your heartbroken kind of where it’s that type of just like presence in your like, chest, almost that like, you just can’t get away from other than through time. And so that one, like, yeah, put me off doing any kind of product thing for a long time and had tons of doubt going into everything I launched.

I assumed it would fail. And so like that’s, and I’ve talked to so many people who were like, yeah, that’s that nobody talks about that. And that’s what it’s like. And also I think like that’s just a necessary. Part of building products is like getting back on the horse after that first painful one. And you know, this is, I always draw this analogy to like dating and relationships.

It’s the exact same, like, are you not going to do another relationship because one failed, like, no, you’re going to go out there and you’re going to find someone else at some point and you’re going to get excited about something again. And so I think, I think a lot of people probably let that first failure just impact their view of themselves as incapable of doing anything that’s going to be successful, which I certainly had.

And I think you just need to like find the one thing that actually does work. And then you’re like, oh no, that was just one thing one time. And it’s not a problem with me. And so I think like now I think I tell people, or I wouldn’t tell people. Like expect the first thing will fail. Like, do it as best as you possibly can try to avoid it, but keep in the back of your mind, like, there is a pretty good chance that you’re not going to get it right on the first time out.

And I would say with that in mind, probably don’t spend $15,000 investing in web site design and Facebook ads, like the big lesson. So the big lesson I learned from that, that set me up for future success is when I launched my current big course podcast marketing academy. I think I mentioned before that I pre-sold that.

And so I didn’t create anything other than a landing page and a lesson outline until I had 19 people. Who’d each paid $500 in order to sign up for it. And then I got to work in like hustle to get the, create the videos and do all of that. That. And, and once I did that, I was like, oh, this is how it’s supposed to work.

This is why people tell you to do that. And I was kind of like, well, I’m never doing it that other way. Again, like everything I create is going to be pre-sold and there’ve been a number of things where I’ve sent out things to my email list saying like, you know, I’m looking for 10 people to do this. I’m looking to create a course in it.

I need the first 10 and I’ve got like three or four people. I’m like, okay, well, I guess there’s no demand for it. I won’t do that. And like, I’ve got enough other ideas that I’m not going to waste my time on ones that there’s no appetite.

Speaking of podcast concepts. This is what I want somebody to make is called a show called Wyatt flopped. And so that would be, every interview would focus on like a business owner or creator and talking through like their failure and in hindsight, why they think that happened, even though they may not know.

I think that would be such a great, helpful show that somebody should

[00:56:15] Megan: Are you going to make it? Cause if you don’t make.

it, I might make that show. I think that’s a

[00:56:19] Jeremy: Yeah. I mean, I’ve been telling people about it, so

yeah, I’ve been thinking like, I don’t know that I want to do that forever. I think like I might do it as like maybe a season of a show that I do, but I’m kinda like, I would just maybe rather listen to it and so somebody else can do it, put it out there and yeah, if you do it, I will be your first

[00:56:34] Megan: Okay, great. You can come back and talk more in depth about your failure.

[00:56:40] Jeremy: Yeah.

[00:56:42] Megan: Awesome. Okay. Well, we’re getting to the end of the show. So I want to thank you so much for being here. This has been a great conversation. I really appreciate it. Where can our listeners follow you, connect with you and just learn more about you.

[00:56:55] Jeremy: Yeah. So I’m most active on Twitter at I M Jeremy ENS and that’s I put that and a bunch of other links to everything else, including my newsletter, blog posts, free podcast, content, all that kind of stuff at counterweight, creative.co/dollar sprout, all one word. And so you can find all the links there and and please, you know, send me an email or send me a DM on Twitter and, and definitely happy to chat.

Key Takeaways

[00:57:18] Megan: Thanks again to Jeremy for joining us for this episode, I went through back what I went back through this recording and wrote down like 10 key takeaways from this episode, but that seemed like overkill. And I didn’t want to overwhelm you guys. So I narrowed them down to my top five key takeaways.

So here are my top five takeaways and some action items that you can take away from this episode.

Key Takeaway #1

[00:57:46] Megan: Can you take away number one?

 Don’t underestimate the power of a small engaged email list. Jeremy made $20,000 in his first year of selling courses with an email list of just 1500 people. He said that about 80% of his sales came directly from his email list.

So I did some quick math and that works out to $16,000 with less than 1500 people or with about 1500 people. So, if you thought you needed tens of thousands of subscribers to make good money with your online business, think again, you can have thousands and thousands of subscribers on your email list and not make seen this with other business owners. I’ve seen so many people talk about this. And I got to the point in my own financial coaching business, where I had over 6,000 subscribers and was getting no sales from my list because they weren’t the right subscribers.

So it’s not about how big of an email list you can build. It’s about building an engaged list of the right people. How do you do that? Well, in episode two of this season with Pete McPherson, we talked about having something to sell before you start creating content. So this is the product first approach, right?

You don’t have to have your product or service fully built out, but you need to know what you’re going to try to. And then once you know what you’re selling, you can work backwards to create your lead magnet or your opt-in the thing that gets people on your email list and create content that leads your subscribers to your paid offering.

So with your lead magnet, for example, think about a quick win that you can give to your ideal customer. That’s the precursor to your paid course, your coaching program, et cetera. And then once you have the right people on your list, Don’t forget to email them, keep them engaged and provide value even when you’re not selling.

That was more than Jeremy and I talked about on this episode, but if I were to go back and start over with my financial coaching business, this is how I would approach it. This is something I did way wrong in the beginning of my own business. So I wouldn’t approach it from the perspective of how can I get people on my email list, but from how can I get the right people on my email list?

Because with the right people, you really don’t need that many to start making good money.

Key Takeaway #2

[01:00:15] Megan: Key takeaway number two.

 It’s okay. To quote unquote, sell out. Jeremy studied audio engineering and school. And when he first heard about podcasts editing, he knew he was overqualified for the work he thought, what would all of my audio engineering friends think?

Would they think that he was a sellout or would they look down on him for doing work? That was quote unquote basic compared to what he could be doing, but he did it anyway. And by selling out, he was able to quit his job and just six months to work for his business and travel full time. So don’t be afraid to sell out or do work that other people might think is beneath you, quote unquote, because that work could just be your ticket to freedom.

In fact, Jeremy said that the reason he was so confident and able to make money so quickly freelancing is because he found work that he knew he was overqualified for. So if you’re looking to start a service-based business consider starting with freelancing and offering services that you know, you’re overqualified to do.

Key Takeaway #3

[01:01:22] Megan: Key takeaway number three.

 You can still make good money on freelancer marketplaces like Upwork or Fiverr, but there are two key tips that Jeremy suggested. Number one, like we just mentioned, look for work that you’re overqualified for. And number two, add your own personality. People who post gigs on freelance sites often get 200 or more responses.

So when you’re messaging someone on Upwork or wherever. Make sure the subject of your message is catchy so that it captures their attention and then add your own personality and flair and mention anything relevant to the listing that sets you apart from other bidders.

Key Takeaway #4

[01:02:04] Megan: Key takeaway number four. Now this one’s a big one.

It has a few different parts, but I think they all fit under the same key takeaway. So stick with me here. Key takeaway number four.

 The thing that sets your content and business apart is unique and novel ideas. And you don’t get those by listening to, or reading tactical style content. There’s nothing wrong with tactical, how to content.

And when you’re early in your business, you probably should be consuming some of that. It gives you a vocabulary and a basis for building your business, but at a certain point, you have all the information you need and you just need to be creating content and getting as much of your own ideas out there as possible.

 Jeremy mentioned three things that have helped him come up with new unique ideas and that he recommends to other creatives first find and consume content that makes you think in new and different ways like creative non-business books, podcasts, blogs, et cetera, for Jeremy that’s content like Seth Godin’s podcast akimbo, which I also love by the way, highly recommend.

Second, keep a list of ideas and add to that list. Every day. I love the Jeremy brought up this exercise by James Altucher, which is to have a daily idea practice similar to a gratitude practice. Like you may already have. Every day, write down 10 new ideas, or you can do three or five or whatever works for you.

By doing this, you can train your brain to always be looking for new ideas, which means you can create an endless backlog of ideas for content or your business or whatever.

Jeremy said he has over a thousand topics on his own idea list. Now, if it sounds intimidating to think of new ideas every day, keep in mind that an idea doesn’t have to be fully formed or actionable. As Jeremy said, it’s just something small that’s interesting, or that you’re curious about.

It can be an opinion, a thought on something that you read a controversial take on a common practice in your industry. Anything. Two things to keep in mind when choosing where to keep your idea collection is you want it to be consistent. So all your ideas are in one place and you can easily see sort and find them whenever you need to and accessible so that you can pull out your phone or your laptop and add it.

As soon as you come up with your. I thought this was a great point because I usually keep my ideas in a Google spreadsheet, but it’s not the most accessible option even with the sheets app. So I think I’m going to try Jeremy’s method of using notion and stuff. And the third and most important thing Jeremy mentioned that helps him come up with unique ideas, creating content.

Jeremy says, if you want to find your voice, your differentiators and your perspective, you really just need to get as much content out there as possible. Creating that content, thinking through your ideas. That’s, what’s going to help you find your voice and your unique perspective. And that ultimately is what sets you apart.

Key Takeaway #5

[01:05:15] Megan: Key takeaway number five.

[01:05:19] Megan: You don’t have to be the best. You just have to keep going today. It’s easier than ever to start a website, launch a podcast or open a new business. And because of this, it can feel like what’s the point. The market is already over-saturated, but here’s the thing, even though a ton of people are jumping on the online business or content creator, bandwagon.

Most of them quit too soon. Jeremy mentioned the stat on the show. He said 90% of podcasts don’t make it past episode three and 90% of those that do make it past episode three. Don’t make it past episode 20. And while I couldn’t find the exact stats on how many people quit blogging before they make any money.

I’d venture to say it’s pretty high, which means you exponentially increase your odds for success just by staying in the race and outpacing your competition. Does that mean that you just keep doing exactly what you’re doing now forever until you’re successful? No, probably not. You’ll probably look back at that blog post or podcast or YouTube video a year from now and think, whew, that was awful, but be consistent.

Learn how to create, create better content and improve as you go. And you’ll outpace the vast majority of the people in your.


So there you have it. Those are my key takeaways and some action items for you. If you enjoyed this episode, don’t forget to follow and whatever app you’re listening on. And if you really enjoyed this episode, please leave a review.

Those help us get the show seen and in front of more people so that I can keep my job and keep producing these podcasts episodes for you. So thank you for listening and thank you for your support. I hope you enjoyed this episode and I will see you in the next.