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Welcome back to the Creator Spotlight podcast. Our guest today is Justin Gordon.

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He started blogging way back in 2012 as a fitness coach and has produced hundreds, maybe thousands, of articles and podcasts over the years.

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Uh, but back in 2018, while working to get an MBA, he started blogging about entrepreneurship, then he started a podcast interviewing entrepreneurs a few months later.

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And today, his main focus, as a creator at least, is his 21,000-plus subscriber newsletter, Just Go Grind.

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And on that newsletter, he still interviews some entrepreneurs, but mostly writes thousands of words long profiles about people like Sam Altman, Daniel Ek, and Coco Chanel. Um, is there anything else you'd wanna add?

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That's great. There's so many things, but that's, that's, that's [laughs] a great intro. You're a guy who does a lot of things. [laughs] Um, okay. So I'm not sure exactly how many people you've interviewed.

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I think it's somewhere around 500. Probably more, honestly.

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Um, but the reason I bring that up is, like, when I interview people for this, I don't think I'm necessarily learning, like, a new thing specifically every time. Maybe, like, you know, if I've interview...

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I've interviewed probably 100 people since the end, since the beginning of last year. And maybe those 100 people, I'm making up these numbers, but, like- Yeah... maybe I've learned 10 things, right?

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But I've learned 10 different angles on each thing. So my question to you is, like, do you feel like you've learned something new every time you research or interview somebody?

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Or, like, what is the new thing you gain from each new interview? 'Cause I, I don't- Yeah... I just don't think it can be 500 new things, like fully new. Yeah. It's definitely not 500 new things.

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I think what you end up happening with it is you have some things that stand out- Mm...

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and then some things that are kind of almost, like, reaffirmed across different industries or reaffirmed across different categories and you're like, "Oh, I heard that from this person two years ago, and now they're talking about a similar thing," or, "They took this approach to that.

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Oh, they're taking the completely opposite approach." So does it really not matter then what approach you take in this particular, like, category, whatever?

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So anywhere from when I started the podcast in 2018, I mean, there's founders from that that all across the spectrum of a lot of early stage, but across CPG, across tech, across media, et cetera.

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And then, as I said, the kind of these, like, world-class founders for the newsletter too.

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Like, now, it's a similar thing that some of these people are, like Coco Chanel you mentioned, like, obviously that she's been dead a long time- [laughs]... but the brand is still going.

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There's, like, a whole different spectrum of when she was building a company and, like, of that, that structure of how she set it up and she basically got startup capital back then as well, which you could say, you know, it wasn't, like, a VC-backed thing, but then she had some guy that gave her a, basically, like, a room or, like, a little, a little space to sell hats out of.

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Mm. And that kinda started the whole empire that it is for now. So then today, you have people who have got set up capital as a kid in their dorm room, [laughs] as, like, Dorm Room Fund, for instance. It's like it's...

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Some of the things transfer on in terms of that, and then the different ways people have approached acquiring customers, different ways people have approached building the team. Some of those things- Mm...

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kind of carry over over time, and you learn some of those lessons. But it's definitely not, it's definitely not 500 lessons, but some of the things that stand out to me are always the things that just pop up repeatedly.

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And so whether it be the importance of building a team and how people have gone about that, whether it be how you approach the sequencing even of focusing on acquiring customers versus- Mm...

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like, the distribution side versus the product side and how some people take product first, some people take a more of a distribution approach first.

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And any media creator or, like, content creator, they're taking a lot of times a distribution approach first- Yeah...

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and using that to sell products or services versus some people who are product people have gone the opposite, create a great product, and then figure they'll figure it out, you know, after that in terms of distribution.

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So it's all over the board on different things, but it's been fun to see the different journeys- Yeah... of all the people.

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Well, I feel like what you're describing is like you're searching for patterns, which is like it's not the new things.

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It's like, uh, I don't know, when you were talking about that too, like, oh, if this person who works in this industry is doing this one thing, and then this person in an entirely other industry is doing it in another thing.

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I g- I think it... Yeah, it's like that angle thing, and I'm thinking about it. It's like you're at a galla- a, an art gallery or, like, a museum.

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You're looking at some sculpture, and it's like there's the one sculpture, but you're walking around it and, like, seeing, like, different ways it works and different contexts and different lighting, and that's like when you learn, like, that Coco Chanel took, you know, some form of capital, and then X entrepreneur also took some form of capital.

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It's like same coin, different sides. Maybe not just a two-sided, but many-sided coin. It's a many-sided dice- [laughs]... or Dungeons, Dungeons and Dragons style. You're right. [laughs] Um. Right.

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So the podcast, though, you started it in t- 2018, summer 2018. Yeah. But what's- Yeah... really interesting to me is that in August 2020, you switched from doing it weekly to daily, um, and- Yeah...

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specifically not, like, every, you know, workday, but seven days a week, and I'm pretty sure you did this for over 100 days. So you started first day of August.

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You did all of August, all of September, all of October, and then November you fall off a little bit. Um, but then you... after that, you're still doing it, like, three days a week- [laughs]...

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if not more, for a little while. Um- Yeah... and all that just to say, like, that sounds horrible to me as, like- [laughs]... somebody who does a podcast. Like, it sounds like a bad idea for me.

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Like, I feel like I'd get burnt out. I'd worry- Yeah... that nobody is listening to them. Um, it's just, it's, it's horrifying to me. So [laughs] I, I really- Yeah, yeah...

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wanna know why you did that and what it was like. I, I think it was from hearing a podcast, I wanna say it's a marketing podcast, like,

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by Single Grain, um, this marketing agency that had done it daily, and I heard how they grew through a daily podcast. Mm.

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And I had seen daily podcasts that had done really well, even, like, Entrepreneur on Fire back in the day I think was daily as well with John Lee Dumas. And I remember hearing that, like, years and years ago.

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And so when I was doing my podcast, I was trying to think of any type of way to grow, because it is so hard to grow an audience. Totally.

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And then I also knew that, like, okay, if I do more episodes, I will just meet more founders. I don't know where this is going to lead to, but I'll build a be- network even faster versus one time a week.

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It's, like, seven times a week. And also then it... the thing I love about an, a daily anything, which is I fought the urge to do a daily newsletter, but trust me, it's still on my mind always- [laughs]...

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is that the habit of doing anything daily, and I used to tell my clients this when I was a personal trainer way back in the day, was likeThere's not a question of if you'll do it or not, the question is what am I doing for this thing?

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Yeah. So it really shifts everything doing it daily. It's reps. So for the... Yeah, it's reps. And for the podcast, it was the same way.

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When I knew I was doing it daily, it was like my eyes were always open to, okay, who could be a potential guest? And I, I had a, you know, high bar.

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The, a lot of these people had raised millions of dollars in, in venture capital, or they were investors who were, were great. And so I was on Twitter all the time.

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I was, like, looking on LinkedIn, always, like, asking for referrals. It made it r- way simpler to be like a reach-out thing. If you have an ambitious thing you're doing, it's easier for people to help you. Mm-hmm.

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So I would reach out to people and be like, "Hey, I'm doing this daily podcast. I need guests all the time, but they have to be great. Do you know one or two people?"

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And I, like, would constantly ask- They're volunteering for the fun to be on almost. Yeah. Yeah. And people would be like, "Oh, I'll definitely help you. You're doing what? That's insane. How are you doing that?"

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But then if it is insane [laughs] people give you more help because they're like, "Oh, it's more ambitious that you're doing this thing." Yeah. So that's why.

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It's not like if, if you're, like, biking across the country, it's, like, way easier to get strangers to let you, like, sleep in their yard or their house other than being like, "Oh, I'm f- I'm, like- Yeah...

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biking across town. Could I stay at your house tonight?" It's like, "No." [laughs] Yeah, no one gets sponsors for a bike ride to their neighbor's house, right? Yeah. Yeah.

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[laughs] Like, you get sponsors for a bike ride across the country. It's more ambitious. And so I always like... It's part of, like, the, I think the Tim Ferriss thing around, uh, Magic of Thinking Big.

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He always recommended- Mm-hmm... that book and talked about it, and you say, like, it's easier to pursue more ambitious goals oftentimes 'cause- Mm-hmm... there's less competition and people are willing to help you.

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So I had that in mind too when I did that. I was like, "What's a more ambitious version of what I was doing?" And the podcast was called Just Go Grind, so, like, clearly, [laughs] like- It's on brand... I live that.

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Yeah, it's on brand [laughs] to be like, "I'm doing this daily." And I did meet so many great founders through that that I have still, like, kept in touch with and know and always knew- Mm-hmm...

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like, the relationship side of podcasting and, and media is what, what I loved, how you could leverage, like, media to meet people.

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And then now doing a lot more of that now we can get into, but, like, always kind of had that in mind. Mm-hmm. And that's the only reason why I stopped daily is 'cause I was... I got into VC from that, so that's why.

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Oh, okay. So that... I love that. I always think, like, with any type of creator, there's some kind of monetization in the goal, but, like, monetization can be getting a job or, like- Sure...

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network, like something that brings you some kind of monetary benefit down the line. Uh, uh, so a few questions here. One- Yeah... uh, it, it got you this job, but did it grow the podcast? It did.

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I mean, d- downloads grew and then inherently the audience kind of, the momentum kind of grew from that. Mm-hmm. It was still... It's never been, like, huge. It's always been, like, relatively small.

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It's kind of niche in some ways. Mm-hmm. Um, it definitely grew the podcast.

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I think the thing that also, if you're thinking about, like a, as a creator hat is on, you're thinking of surviving, if you have something that's smaller, it's fine, but when it was...

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I was doing it daily, the, the amount of ad slots I had then is more as well. Yeah.

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So it was easier to pitch and then, like, I got maybe a couple sponsors for it, where it was like, okay, August, whatever, maybe it was like $2,000 or something, and it's like for one episode.

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Obviously, it's, like, way too much given the downloads, but it's like, okay, I have seven a week though, and there's always new things I'm promoting on social- Lots of surface area... for the podcast.

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So there's lots of surface area. Exactly. And then you can think about the amount of content I can create with having a daily podcast. There's so much- Yeah... to repurpose and stuff. Well, so- So it's easier...

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what about, what about, like, um, each podcast, I'd say, I, like, scrolled through this period on, on Spotify. Yeah. And I think the average length is probably 50 minutes. Yeah. So I'm interested in a bit of the process.

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We don't have to go too granular, but, like, how long- Yeah... before you start... How long before August 1st had you started, like, pre-recording and getting people booked, and, like, were you- Mm...

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doing, like, batch recording in a day? How did you pull this off executionally? Yeah. Yeah, I was a little bit ahead, but not much.

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I might have been, like, a week ahead of interviews that were, like, ready to roll, but not much more than that. Yeah. So the actual process then, so I had a, one assistant help me on the editing side of things.

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Um, I did a lot of it myself in the early days, but I did have someone help me after a little bit. But I had maybe, like, seven, uh, seven episodes kind of ready to roll. So I had a little bit of, like, leeway.

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And then I would just batch as many as I could in a week. And so, I mean, the most I did was maybe, like, four-ish or five maybe. I think it was four in a day. Uh-huh.

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And, and that's a lot of, like, mental space- Yeah, wait... to pull it off. How long, like how many hours would you spend per episode in terms of, like, research, recording, prep, et cetera? It varied.

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So normally for that, it was, like, hours and hours of research. Still, like, I do deep dive research- Yeah... for these, uh- It's your thing... deep dives. Yeah.

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I, I think you have to be prepared 'cause what happens is so many times I get, uh, guests that would come on, and they would...

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I love it when they say, like, "Oh, I didn't," like, you went, you did your homework or you did your research or you really- Yeah... that makes it stand out, and there's a reason for that, and I can give them that too.

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But it's a whole process for, like, if you do a good job with that and they've have had an amazing experience, and part of that is the research you did beforehand. Remember, I was doing it daily.

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I needed recommendations from every guest. So what I would do at the end of the episode is I would always ask for a recommendation to another potential guest. Mm.

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And if I did my homework and did it better in that episode, they're more likely to give me a, another referral to other good guests.

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And these are people who, like, at the time, I didn't have a network, network that was too huge to, like, be able to refer to other, like, vetted kind of, like, venture-backed founders who had raised a lot of money or, like, who are hard to reach if I just cold outreached to them.

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I needed, I needed those recommendations. Yeah. So that was helpful. So there, there was, like, hours of research for each one.

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So to do three or four in a day, that means I was doing research on each one before then to prep. So, like, it was, at the most, it was probably, like, 10 or 15 episodes in, like, a week I would do. Jeez. Yeah.

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That's insane. But constantly on- ongoing, just you have to be ready to roll. Yeah. And that was, like, like you said, 100 days, so it was like three months, four months of that.

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I, I, I, again, like, to me, that, that's... I, I would not do that personally. That's just [laughs] not something I would do. Don't recommend it necessarily. Um, dude, would you, would you do it again?

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Or, like, would you recommend people do that? Or, like, would you recommend people d- do a similar thing in a different way? I actually think it's great for jump-starting any project- Mm. Mm-hmm... as a purely...

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And yet there's different, like, trains of thought on this. Some of the- Well, famously, Ship 30 for 30 is a big, you know, thing people do. Exactly.

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I think the benefit of it is it gets you reps on becoming better- Yeah...

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at the art of doing podcasts and of doing outreach and getting momentum and having something to promote daily that you can just, like, you know you have a new episode to promote.

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So you always have to be kind of-Promoting and self-promoting and shipping, which some people struggle with that. I've gotten over that after, like years of blogging, but, like that was helpful too.

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So I, I think from that perspective, it's helpful. The, the problem is, like you have to be [chuckles] willing to kind of, uh, suck it up a little bit because it's hard, obviously- Yeah...

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but also figure out the monetization, make it make sense, 'cause it's way easier to do that when you have money coming in for each episode, right? So, like there's trade-offs on that.

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But for me, I mean, it was, it was so worth it. L- thinking bigger picture, it was incredibly worth it. Tough at the time- Yeah... but life-changing. Yeah, absolutely. Yeah. Um, so one more thing about podcasting.

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Six months into podcasting, so before your, you know, w- your marathon, uh, you wrote this Medium article, "Six Lessons Learned From Six Months of Podcasting." Yeah. Uh, and I'll, I'll read what those six things are.

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So just start, don't be afraid to ask, uh, as in ask guests to come on, um, don't expect perfection, have backups, meaning audio specifically, uh, get referrals to guests, and do your homework.

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Um, so six lessons from six months of podcasts. It's been about six years since then. Uh, is there anything you'd add or change?

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I don't know if the, the lessons-- Like the main takeaway from podcasting in general has been relationship building. It is like the best tool for doing that. It gives you an excuse to reach out to anyone.

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Most people are-- A lot of people-- I said most. A lot of people are willing to come on a podcast. Yeah.

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I think a lot of people will make time if you've done your homework and done all those things that I've mentioned in there, is like they will jump on and do a podcast.

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And if you use the r- use it the right way, like it's almost like second to none in terms of relationship building. 'Cause even like- Mm-hmm...

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obviously, like in person is the, like top thing for building relationships, but most of these people, if you wanna expand outside your city and kind of broaden your network and have these second connections, second-level connections and stuff, I think it's the best thing.

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But I would just say that if you c- if you approach it more strategically, it's helpful. Yeah. So I'll give you some context.

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So I knew from the beginning this is gonna be great for building relationships, but if you just do a podcast interview and that's it, you've kinda wasted that podcast interview in my, in my head. Mm-hmm.

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'Cause what you could do or should do, one, like are you following them on social already? Are you kind of engaging and having those like nudges? But also, like I would ping all the guests. I, I'll give you an example.

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I just did this this week. I pinged almost all my podcast, almost all the podcast guests that are relevant for this new thing I'm building called Village Lane.

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So I pinged them just like giving an update of like, "Hey, by the way, here's what I'm up to now," and I did that for when I joined a venture firm, when we launched an angel group, when I left the venture firm.

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Those things that people probably wouldn't think to do, and it takes a lot of time 'cause it's like 350 something messages I just sent. Yeah, individually. Like-- Individually, [chuckles] exactly.

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Like that's something like, "Oh, why would I spend the hours on that?" 'Cause it's worth it if you're playing the long game.

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And even though a few people will, you know, not care at all or not respond, I always get people to respond and still keep that up after years.

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Like I'm having a call tomorrow with someone who I haven't talked with in four years. Yeah. But we've kept in touch from the podcast, which is insane to me.

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But I think that's the best part of the podcasting thing, is like the relationship building side of it, uh, is just second to none. Yeah. Okay, I wanna move on b- from podcasting, though.

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So the newsletter, um, get into the, the, the details of it. It's like it's, it's called Just Go Grind.

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It's this thing that's evolved from like your early days of blogging about career, entrepreneurship, and now it's largely these founder profiles. Um, but before we get into what it is, what are the stats?

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What's the-- How many you've got-- Uh, I know, all I know is you've got- Good question... over 21,000 subscribers, so what's the subscribers open rate and click rate? Yeah, subscribers are around 21,000.

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Open rate's around, I have to think about this, look it up. It's like probably 45. Click rate varies, honestly. Click rate's probably like 2%, so probably- Mm...

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probably pretty low, relatively low click, like depends on like what you gauge it by. Yeah. Um, yeah, that's kinda the baseline at least of it so far. 42? Yeah. I'll take it. What about, um...

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I mean, I feel like your newsletter isn't a big click newsletter. Um- Yeah, 'cause they're reading a deep dive profile, which- Yeah... has been a whole different vibe. [laughs] What is it, like 2% or something? Yeah.

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Like 2%. That's, that's pretty good, um- Yeah... for, for what it is. The first i-issue of your newsletter I, I found like as it exists today as like a dedicated- Yeah...

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thing seems to be from December 2022, which was like a review of- Yep... of your 2022 and- Yep... you know, your plans for 2023, and it, a-as you note in the top, you sent it to 519 subscribers. So that was, uh, what?

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Like 18, 19 months ago or something like that. Um, so why did you start this a-again, it's like this 12-year thing of you making content in various ways. Yeah.

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Why did this thing happen where you started doing this like dedicated newsletter? I mean, that's [chuckles]... It's a funny thing about like things that people prioritize, uh, in terms of careers. Mm-hmm.

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I always kinda have prioritized things around impact, things I'm inherently curious about, things that can eventually get big. I guess I'm willing to wait, and I want- Mm-hmm... so like that's kind of always...

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So at the time, to give more context, at the time working full-time at Vitalize Venture Capital. Mm-hmm. Was doing the podcast still.

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Had shut down a founder community I was-- like an online founder community I was, I was running. Um, too many things going on, right? [laughs] So I sh- so I paused the podcast like not long after that. Mm-hmm.

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And I just wanted to get back to writing. Again, I'd done it for like a decade, so I wanted to get back to like writing on the internet, and I just had some ideas that I wanted to like share.

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Uh, I didn't really know at all where it was gonna go. I didn't really plan on it being a thing necessarily, but I knew that I'd seen other people writing more. I wanna get back into like a newsletter.

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I kinda had played with newsletters in the past in different formats. Justin's Journal was one of those. Mm-hmm. I think there's like a startup hiring one.

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There's like other stuff I played with, and that's where those 500 subscribers came from- Okay... like past newsletters I just imported.

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And I just wanted to start getting these ideas together, and so that was like the genesis for a minute. Obviously, it evolved, which I'll get into, but it evolved over this like first couple of months.

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But I just had certain things I wanted to get out, and I think any project I've, any project I've done it's always kind of stemmed from that, of like something I just want to do. Mm-hmm.

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And we'll see how it turns into something bigger. Yeah. You, you've got a lot of motion. [laughs] I think it's helpful. Um, yeah. Uh, so okay.

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So 519 subscribers then to over 21,000 now is, is quite good growth, and like 21,000 is like a super strong list. Where did they come from? How did you grow it?Yeah, it's a mix.

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So I started with organic originally 'cause I had a Twitter audience- Mm-hmm... which was helpful. So I built that up over time.

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So, like, let's see, by 2023, which was really when I switched to the current format, probably had 20,000 maybe Twitter followers, some- something like that. Um, definitely leveraged that.

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So I probably got to, like, the first three-ish thousand maybe, around that subscribers, um, organically. Started doing paid ads a little bit after that, and trying to think of the timing.

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Took a, a newsletter course, um- Mm... with, like, Jack Raines and Nathan Bas. Um, that was helpful.

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Learned a bit more about paid acquisition, used that as well to grow it a little bit more, um, which was helpful to get that to a kind of critical mass. 'Cause for me it was, I liked doing the newsletter.

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It was taking up a lot of time 'cause the deep dives take forever- You read a lot, yeah... which I get into to write. [laughs] And then I was, like, you know, working at Vitalize.

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So I wanted to grow to a point where I could, could I get this to a point faster where I can potentially figure out what this thing is and maybe- Mm... quit my job, which is what ended up happening by May. Okay.

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By, by last May? Yeah, last May, 2023. Okay. How many subscribers did you have at that point? I think it was, like, 7,000 or 8,000 maybe- Okay... by then. Yeah. Yeah.

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Um, okay, so we're, we keep talking about, like, what the newsletter has become now. So when I- Yeah... looked through it, there's, like, I think there's about 72 issues since that first 2022-2023 planning one. Yeah.

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Um, 56 of these are your, like, in-depth profiles which, you know, at the first one, which was February 2023, was Sam Altman from obviously OpenAI.

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Uh, it's, like, 3,700 words long, and you sent it to 677 people, and this seems to be the genesis of this format. Um, and then the rest- Yeah...

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are, like, you've done maybe a dozen interviews, like, obviously a kind of an evolution of the, the podcast. Uh, there's a few, like, five lessons from, you know, Stewart Butterfield or other entrepreneur.

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But it's by and large these in-depth profiles. So tell me why you started doing these profiles and what they mean to you. Yeah. Oh my gosh. So I was listening to- [laughs]... My First Million podcast. Yeah.

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And they were talking about their Billy of the week. Mm. And it's a fun segment they had. And they were talking about Sam Altman, and I think they had mentioned- Billy of the week. It was, it's like, uh, their...

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It's like Fool of the Week, whoever made... It's like Donkey of the Week on, uh- No... their, what is it? Like their Billionaire of the Week. Oh, Billion. Yeah, yeah, yeah. Like Billy that way. Yeah. Yeah.

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So, like, they were, like, talking about Sam Altman, and I, they were talking about his... I think they had mentioned his investment in, like, Helion or something the name of it. Mm.

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It's, like, a couple hundred million himself invested, and I was just like, "Wait, wait, wait, wait." I, I know Sam Altman, like, I've heard of him at the time. Like, I knew, like, Y Combinator related, whatever.

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I didn't know the depth of his investing and other stuff he had done, and I was just... Again, I do things that I'm inherently curious about- Yeah... and we'll see what they become.

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So I was just like, "Okay, I've done these kind of deep dives on founder workouts a decade ago." Mm-hmm. And now it came back into writing, I was just like, "All right.

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Let me start to research Sam, and maybe I'll do, like, a piece on him and see what this thing becomes." And so it took me a couple weeks 'cause I didn't have any format down. I didn't have... I don't know how much...

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I took a lot of time researching 'cause also I didn't have any, like, idea of this process and what it would be. There's no system. Yeah, no system in place or anything.

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And so that was over the course of, like, two weeks I put together this thing, and again, still working full time. So it, it was a lot, but I, I love the process of it, like, figuring out.

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Like, basically it's going through, going through old articles or profiles of him, listening to podcasts, watching videos, and then curating that into, like, one cohesive piece and one cohesive, like, narrative of his story.

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And I found it just utterly fascinating 'cause I wasn't limited by who I had access to like I was- Yes...

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with the podcast, and I wasn't limited by, like, a time constraint the same way of, like, I have an hour to talk to them, how much can I get out of them in an hour?

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And also then I can corroborate, like, their story across different versions if they've ever told it differently to be like, "Hmm," like, is what's consistent or not? Or like- Yeah...

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they mentioned this, but actually they mentioned closer to the time it actually happening, this is how it was, and I trust that more.

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So there's, like, other things like that I just found fascinating, uh, and that was a, the genesis for doing deep dives. Uh, yeah, and it morphed from there- Mm-hmm... in a lot of different ways. But yeah.

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Do, do you have a preference between doing those or doing interviews? They're so different. So the current, like, right now with working on a new venture, again, called Village Lane, more of a community focused thing.

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Like, the deep dives take 20, 30 hours. Yeah. Podcasts are just way shorter, which in some ways is helpful from doing it. But I think

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I enjoy the research phase of the newsletter piece probably more, um, because I just get to consume a ton of content and learn things- There's so many directions you can go in... all the time. Yeah.

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I, sometimes the [chuckles] actual putting those pieces together, uh, is less fun, let's just say. Buddy, I know it. [laughs] Especially- It sucks. Yeah, yeah, yeah. So there's that piece of it.

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But you just kind of do it 'cause you know... I- I'm fueled by clicking Publish. Mm-hmm. So the, [chuckles] having done all the research then I'm just like, "I wanna publish this thing. I wanna get it out there.

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I think it's gonna be useful." So slog through the rest of it to make it an actual cohesive narrative. Mm-hmm. So a couple questions about these profiles.

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One, like, reading through, I read through a couple of them and, like, just looking at the mass of them I'm like, so many of these people- Yeah... are very well covered. So, like- Yeah...

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obviously my first question was like, well, what do you, like, what's additive about what you're doing? What's- Mm... how are you telling this story in a new way?

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Or, like, what's the layer you've added by collecting these things? Which the way you're kinda saying it, um, I'll, I'll say something and then let you answer.

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The way you're kind of saying is that, like, you are corroborating these different things, different ways they've said it.

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Um, and then, like, what I kind of landed on as, like, what I thought the greatest value was, was, like, you've got this audience of now 21,000 people, um, and you've got great open rate, right? You said, like, 45%.

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So it seems like to me maybe one of the main values is, like, regardless even of any, the way you're telling the story, it's the curation of it and this, like, delivering of it to the audience, um, in a way where maybe they weren't going to look up Sam Altman this week, but you've delivered it to them.

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Um, anyways, I don't wanna put too many words in your mouth.

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So yeah, what, what do you think is, like, the thing that you're bringing that's additive of what you're doing on these stories that have been told?Yeah, the problem inherently with any of these people I cover is because they've done so many different...

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Some of them have done, like, a ton of podcasts and stuff- Mm-hmm... and so, like, done a in- a bunch of interviews. Some haven't as many, so it's a little bit different.

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But there's always bits and pieces that are missing or- Yeah... they add...

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Even if I listen to one podcast, I- So typically, you know this too, it varies from, like, 10 sources to, like, 30, 40 sources depending on- Yeah...

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like, it could be one source if it's a book for someone, but it could be a lot of sources.

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So there's always bits and pieces they add to each one where, okay, there's this one thing here that was good, there's this one thing here that was good, there's this other thing here that was good, but they didn't have it all in one spot.

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And to me, I like things that are complete. [laughs] And, like, I can ask anyone who, like, uh, talks to me, that's like I'm organized, very organized on things. Mm-hmm. I like things in their place.

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I like to, like, have it in one spot. So, like, to these people I write about, I want this story and this narrative and their insights in, like, one spot, both for me personally and then other people find it useful.

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Um- You've got this completionist tendency. Yeah. Like, just in terms of that. Like, if I'm gonna do it, I'll do it deep dive.

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Like, that's why it's, like, impossible to do a daily newsletter for me, 'cause I don't know how- [laughs]... I can complete something daily. And I would do it, but it'd have to be the right format. Mm-hmm.

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Uh, that would seem enough to me to organize in a way that was also beneficial. Um, and it's like you're kind of attracting inherently a different audience because it is so...

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The depth is there, and I'm, I'm not going for mass appeal. So- Yeah...

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like, I don't care if it's ever gonna be mass appeal because to me it's like people who would enjoy these stories the most are, like, like a friend of mine who is, like, a Series B founder and he, like- Yeah...

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likes the newsletter a lot. And, like, he doesn't really... He's a hard critic. So him- [laughs]... saying it, he's, like, legit when he says it, like, he enjoys it, that, like, is a win for me 'cause he has a high bar.

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Other people who said the same thing when I've talked to them, and, like, I don't get a ton of feedback always on it, but when people tell me it's like, "Oh, yeah, the newsletter, like- Mm...

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keep that going, by the way," it's like, okay. Well, again, it sounds like, like the podcast, it's like this network value is such a huge part of why you do what you do. Yeah. For sure. Yeah. 100%.

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That's, like, the main, the main thing. And it just... This is just way better in terms of this versus news, uh, the podcast. Yes, they can both scale, but just way easier to scale a newsletter. Yeah.

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Um, now it's a different, like, audience of course in terms of, like, you're not having them for an hour listen to a podcast. You have them for less time, but- Mm-hmm...

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if they're gonna read the newsletter, it's gonna take them 20 minutes if they wanna actually- Well, wait. So I'm curious though, like, a- about the audience and your relationship to them. Like, 21,000, it's, uh- Yeah...

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I'm sure that's still not mass appeal, but that's, like, quite a large audience for a newsletter. Um, w- who do you know, like, who they are on, from, on, like, a mass scale or, like, individually- Yeah...

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people you didn't know earlier? Yeah. And I've used, I've used, like, forums to get some, some feedback, so I know it's more than half that are founders. Mm. Um, and others are a mixture, operators.

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There's definitely some investors there as well.

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It's interesting 'cause I've, especially early on, thought a, a little bit more in terms of looking at every single subscriber that comes in and you're, like, looking- Yeah...

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through who are they, whatever all- Google their name and see where they-... in super early days. Yeah. Mm-hmm. But, like, I have...

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It's an interesting list because it's, like, I know people on that list who are founders of multi-billion dollar companies and some, like, tier one VCs, but also people who are just getting started or operators to, you know.

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So it's, like, a full spectrum of it because of the depth of it and because- Mm-hmm... of who I cover. It attracts this, like, unique kind of group of people.

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But inherently if anyone's gonna subscribe to a newsletter and they stay subscribed, and it's, like, sometimes 7,000 words,

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they care about the s- subject or the topic and they're probably filtering for some level of ambition and stuff.

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So, like, all those things to me, like, I've never really cared about the size that much, it's more like- Yeah. The who... I'm gonna keep writing how I wanna write. Yeah, the who. Exactly. Mm-hmm.

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And so that's, like, the big benefit of doing it at least that way for me. Yeah. Um, uh, so I'm, I'm struck by something.

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Like, I've talked to a few people who are creators, but they're also a- athletes and y- so I know you played, uh, football in college and you're a big runner. Um- Yeah...

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I g- I, I get the sense, like, the way you do things is, like, you're just at full tilt. You're always- [laughs]... kind of running, like, leaning forwards. You're, you're, like, falling forwards but just running fast.

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Um, I s- uh, uh, if I have a question here it's, like, is there a relationship between, like, do you think between, like, you being an athlete and the way you do these things?

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Like, is there a mindset that is the same for both or something? Yeah. I think it's a combination of things. Like, if you look at being an athlete also and just researching these people I research every, every week,

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to get to where they wanna get to, whether you wanna be an elite athlete or you wanna create a big company or even just a, the best com- whatever, it takes massive action.

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Like, massive action is, like, the only way you get there. So I've always as a baseline been like, "I will for sure be taking plenty of action in anything I do 'cause I will get more feedback, I'll move faster- Mm-hmm...

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whatever." And I, I, like, journal every d- every day. I have a daily journal. I journal every single... So I always, like, reflect and think back.

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So, like, even though I'm sprinting I do take the rest 'cause I also, I'm- Yeah... a former personal trainer and exercise sports science, uh, major and all that. So, like, I understand the importance of rest.

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But the thing that separates most people is just action. Yeah.

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Like, even anyone you, like, always research all these people, I've had done all these interviews, it's always just action, and [laughs] they're just, like, normal people who then took a ton of action and then that over time makes them seem very much so not normal, I would say.

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Uh, and I always say, like, I love these, like, crazy people. Most of my friends are founders who are crazy as well. Yeah. And so, like, for me that's, like, table stakes. So, like, if I'm, like...

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See, people see some of the running stuff or the, like, um, waking up super early or- Mm-hmm...

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the daily podcast and all that, but to me, like, I'm looking at, like, the crazy David Goggins of the world or, like- Yeah...

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the crazy, like, founders who, like, took things way too far and to me they're just, like, they're normal.

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[laughs] Well, there's, there's this quote I like about Kobe Bryant that he, like, he's the lead scorer of the NBA but also the leader in shots missed, right? He just took more shots. Yeah. For sure.

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And I, I mean, and also that he just played long enough to have such so many accomplishments in his career, right? But, like, the action part of it to me was always just, like-That's table stakes. Mm-hmm.

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So, I mean, that is something I can control super easily. I could at least do a system every day. Like, that's table stakes is the action piece of it.

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And like at least if that's the case, I know I was making progress towards things, and I always like kinda step back and reflect, but I will always be making progress and not be like...

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I don't wanna make mistakes from being a sloth and not moving fast. That to me is, like, unacceptable. [chuckles] Yeah. Um, we... You know, we've been talking about all these things you do.

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How do you actually make money?

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Like, if the newsletter is a loss leader, and it's, like, helping you funnel to, funnel to all these things, you know, I don't necessarily need you to tell me, like, exactly how much money you make- Yeah...

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et cetera, but, like, how do you make a living within all these different things? Yeah. Yeah, so early on, so the, the... Before I quit Vitalize, the main thing I wa-wanted was, like, validation on sponsorships.

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So when I got my first sponsor, I was like, "Okay." It's like, just, like, a mental weight of I can get sponsors for this newsletter was lifted off.

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And then it was like, in my head, it's always like, if you can do it once, you can do it twice, right? So, like, I got a sponsor. It was clear that I could get another sponsor, uh, at some point in time.

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And so then it was like, okay, I used that to get sponsors. So the majority of the thing has been sponsors so far. Um, I had a paid subscription I launched in, like, end of May, maybe June last year.

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Uh, that was, like, a mixture kind of, like, online community and, like, bonus content. So I did that as well. So those are, like, been the kind of two pillars of making money for this whole thing over time. Mm-hmm.

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Now it's evolving. [laughs] So now we'll see- Well, also real, real quick. Be- Yeah... before I move on from sponsors. So it's like this goes back to, like, you don't need a huge audience- Yeah...

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because it's who is in the audience. So you're able to charge to get these- Way higher... specific sponsors and, yeah, and charge higher rates because you have this, like, very value concentrated audience.

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Yeah, and also the market's definitely changed last year in terms of, um, ad rates and sponsors and all that. Mm-hmm. So it's still, like, a premium, premium always.

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So maybe at the peak, at the peak, I've gotten over 100 dollar CPMs. Now it's m- it's less- Yeah... for sure. Like, it's been more like 50 or 75, but at the peak it's that. Still very good. So, like...

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Yeah, and like it... There's variance, right? You know, you charge more, it's hi-harder to get sponsors, all that sort of thing.

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So I think for the first, like, long time it was sponsors and then this, like, paid subscription. So that fueled enough to, like, survive off of, et cetera.

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And then as I've changed this community thing, it's evolved to, like, I've kind of taken a step back both from, like, outreach for sponsors and, like, this paid newsletter, all that. I'm rethinking everything.

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So I'm at-- [scoffs] I've killed off communities that I've started that were pay, had paying members 'cause it just didn't feel like the right thing. So- Yeah... I'm not afraid to do that. Which is good.

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You gotta know when to quit. Yeah. Even if it's making money and people are like, "Why are you starting?" Like, "Maybe just find a different way to do it." Like, "No, I don't wanna do it.

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My energy's not there, so I'm, like, not gonna do it." So now the focus is on, like, Village Lane as a membership community is part of it.

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Sponsors, I took a step back for a little bit, but now it's, like, more evolving around sponsors will be a mix of, like, event sponsors, some media assets- Mm-hmm... with the newsletter,

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the Luma calendar I have, like, they can promote in there. It's, like, a mixture of things. I haven't quite figured it out yet, but I'm definitely prioritizing members.

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So to your point of the audience, there's 21,000 subscribers.

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Like, I'd rather have a thing that's 1,000, 2,000 bucks a year or whatever, or 100 bucks a month, whatever, that type of price point for a membership thing- Mm-hmm...

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to me long term for my audience, like, that's what I just want to run. So I'm transitioning towards that if that makes sense.

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You have enough people that will pay more than you have, like, total people who will pay a five dollar a month thing or whatever. I... That's the thesis. [laughs] Yeah. Well, I mean- Talk to me in a year. [laughs] Yeah.

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Yeah, exactly. Depends on what you deliver. Right. We'll see. Yeah. Yeah, exactly. But I think that those incentives align a lot for what I wanna build. Mm-hmm.

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So that's where I'm shifting now to that, which is a little adjustment period to just figure out, like, what this looks like now. Yeah.

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So now it's, like, giving up some maybe short-term revenue for longer term what you wanna build- Yeah... which I'm happy to do. Um, well- As long as I have enough runway.

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Speaking of that, yeah, so I'm curious more about Village Lane. So does this spring out of- Yeah... like, the Just Go Grind meetups you're doing, where you're like, "This is interesting. It's working.

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I'm, like, facilitating these things. I think I can do it with more value- Yeah... on a higher scale"? Yeah, and, like, something... I did, like, 40 or 50 discovery calls with founders too, and like- Wow...

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a vetted thing that's, like...

252
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A vetted community of some sort is what people wanted, especially, like, if you imagine some founder who's, like, raised money or a founder who's, like, done 100K in revenue, which is the requirements.

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Like, they wanna be around others who have done the same- Mm-hmm... not someone who's just getting started. So otherwise, it's just kind of like they're not getting value from it, but they are just giving, giving value.

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So it's like a hard- You need a bit of gatekeeping. Yes, it has to be in some way. So, like, the LA kind of startup ecosystem, um, events I'm doing for Just Go Grind, those are free. They're open. Mm-hmm.

255
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So I think you gotta allow, allow some serendipity. Village Lane is more vetted. Mm-hmm. Now, the vetting can change in terms of, like, those requirements.

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Like, right now it's, like, 100K in revenue or 250K raised minimum. Those may change. Like, I don't know if I'll keep them forever that exact way, but it'll always be vetted in some way.

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Like, I have a call with everyone, like, who applies. So, like, it's so early. I, like, only a couple weeks ago have launched it.

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So, um, still, like, having member calls and all that and figuring out what this looks like.

259
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But that's very much so intentionally a higher price point membership thing, which I haven't really done much of before, so we'll see- Mm-hmm... how that ends up playing out.

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You have to kind of overcome this, like, cold start problem of getting members, which is gonna be fun. But I have applicants, and, like, I can work, work that list.

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So I want, I wanted a distinctly separate thing that was membership and that was in-person focused and that I could use the media to drive people to that. Yeah, that makes sense. Um, okay, just a couple more questions.

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Yeah, yeah. One, what is the most disastrous interview you've ever done as an interviewer? Um, and you don't have to, like, name names. Um, that, you know, if you want to, you can.

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But I'm more interested in, like- Yeah, yeah... as somebody who interviews people, I'd love to learn, like, what went wrong, why it was bad. Maybe there's none. Yeah.

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Maybe you've, you know, knocked it out of the park every time. Oh, no, there's definitely one. Yeah. Okay. Yeah, yeah. [laughs] Yeah, let me know. [laughs] There's th- There was one who was, like, a...

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This is, like, typically not always a telltale sign, but, like, there's one who reached out to me specifically to be on the show. This was, like, early on. Maybe one- I usually say no to those. I'm always skeptical.

266
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Exactly. Very much so. And I didn't know that 'cause it was early. It was maybe the first, like-30 or 40- Mm... one of the first ones.

267
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And it was when I was doing not necessarily just founders, it was kind of across the board. So this one, they just... [laughs] One, they droned on about everything.

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Every answer I c- felt like I couldn't get them to be concise in any way, shape, or form and m- I would take full responsibility for some of that when it's like you have to warn your guests like how to do that. Mm.

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Es- especially if they haven't been on a show before, they don't know. So some blame on me for that. But they droned on for every answer, and it was clear they would kinda like sell more than like- Yeah...

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just- Than chat... be natural. Yeah, than have a conversation. It wasn't a conversation at all, which wasn't enjoyable for me. It lasted way too long. It felt like, "How do I get out of this?" Like- [laughs]...

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it was a lot of like... I felt trapped behind the mic. It was terrible. And I was like, "Never again." Like, I will never again... Like, I will be more prepared, I will make sure to vet the guests more.

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Taught you the lesson. I will only talk to people who, like, I'm genuinely think I'll be excited to chat with.

273
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And this was already hesitant in the beginning, and I went with anyways, and, like, all of those things I would never do again. Yeah. Um, so as you said, that was the first 30.

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What, what about the best interview on the opposite side? And why was it- Yeah... why did it go so well? I almost always think of Rob Mather from Against Malaria Foundation. Um- Mm... anything where people,

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like, think differently about things, I love, 'cause that just, like, changes your whole mindset shift, whatever. But he started, uh, Against Malaria Foundation.

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It's basically, like, one of the most impactful charities in the world. So, like, if you look up, like, charity rankings and stuff, like- Mm...

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Against Malaria Foundation always ranks, like, highest or, like, one of the highest, like, every year. And started from a, you know, wanting to make an impact.

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Uh, and one of the things he mentioned in that interview, which is why I enjoyed it so much, was, like, this idea, I don't know if it's, like, seven-minute thing here.

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The idea basically of using, like, only a few minutes of time, how could you make maximum impact? Mm.

280
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For him, it was, like, a one-minute call with, like, five to 10 of the most impactful, like, um, important people that would help his cause.

281
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And it just gets you to think a little bit different when people put limits on something, or they put, like, these, our own kind of blockers on things.

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It's like you could really probably do 10 times, 100 times more than you think if you kind of thought of it or took a different approach to it. Mm-hmm.

283
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Which is why sometimes it's hard when you're just kind of cranking through stuff. You're like, "Well, but if you took a step back, then maybe it'd actually be better."

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So that interview was just enjoyable, building something impactful, learned some things from it, was a joy to talk to. And I've had many interviews that I, I truly have enjoyed. Like,

285
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like, you sit back after and you're like, "What just happened? That was amazing." Like, you're like kinda like had to walk, take a walk or something. Yeah. Had many of those.

286
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But Rob Mather from Against Malaria Foundation's always one of the ones that stands out. I'll check that one out. Um- Yeah...

287
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okay, how about any advi- first advice for, for other podcasters, anybody out there who, like, is, you know, whether they're thinking of starting one or they're deep in one, um, what advice would you give about podcasting?

288
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I mean, at first it's always just about, like, figuring out what you want from it. Okay. And you may not know at the beginning, but having at least an idea of what you want from it is something.

289
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I knew I wanted to build relationships as a starting point. Mm. So I've always wanted- Oh, oh, so wait, sorry to interrupt. That, that's really interesting to me, 'cause, like, it, that...

290
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it's clear that that's what came out of it for you, but, like- Yeah... I'm, I'm surprised that that was, like, what went into... like, that that was your thing at the start.

291
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It was like, "This is a networking tool for me." Yeah, because I was doing it as blog posts originally, but I didn't get to talk to people and form a relationship with them. It...

292
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when I was doing it as blog posts, I was doing- Were you doing, like-... guest posts... written survey interviews or something? Yeah. Yeah. Exactly. Exactly. And I was like, "Well, I can't talk to them.

293
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I can't ask follow-ups. I can't, like, build any rapport with them." So then I was like, "Wait a minute, like, it has to be a podcast." You can't interrupt them- That's the only-"... like I just did you.

294
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[laughs] Ask a follow-up question. Right. You can't do that. But the- [laughs]... some interruption's good, though. Yeah, exactly. But some... Jason Calacanis does maybe sometimes too much, as an example. Mm-hmm.

295
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Love his, like, his style, but it always stands out to me when some people do too much of it. But you can't do any of that with a written interview- Mm... which is the limitations. Yeah.

296
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How about, um, for newsletters- Right... what's a piece of advice for people to... Uh, especially, and I, I really ask this of you 'cause, like, part of why I wanted to interview you is, like, people don't write 7,000...

297
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You just don't write 7,000-word newsletters. It's not done. Um, so- [laughs]... that's, that's one of the main reasons I actually wanted to talk to you.

298
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I was like, "This guy's, [laughs] this guy's doing something different." Um, so yeah. What's your- [laughs] What advice would you give to people, uh, trying to write a newsletter? Besides, like...

299
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I, I, I think of this as the same reason, um, like figure out- Yeah, yeah... why you're doing it. But beyond that, like, format specific. Is it... Or does it even- Yeah. I mean, I have strong opinions on that always.

300
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Like, I think the thing of, like, Acquired as a podcast, for instance, I know you've come- Mm... on newsletters.

301
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But Acquired as a podcast, for instance, like breaking every rule of podcasting because this was what they wanted to do, and they're just kinda scratching their own itch and whatever, and you find your people through that.

302
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I think more people, more people should be doing that without worrying about constraints. Yeah. Just based on what do you want to create, period.

303
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If it would've been, like, asking me, I would've followed the advice, done like a super short newsletter, maybe had it daily 'cause it was like, uh, you know, you had The Morning Brew, you had The Hustle- Mm-hmm...

304
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you had, like, The Milk Road, all these ones, right? That would've been probably the advice I'd follow. Like, but to me, it was always like, "What am I gonna find interesting enough to be able to do consistently?"

305
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And that has always been a thing I wanted to, like, try to pursue is, like, the things I would just enjoy doing anyways.

306
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And so, like, I was already researching people in some capacity, being like, "I'm curious about so-and-so." I'm like, I would just- Yeah... do that.

307
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So, like, then it's like, okay, I can make a business out of this or make a thing out of it.

308
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So for anyone, like, starting a newsletter, it's like what is the thing you just are curious about anyways, and then you start and it morphs from there. But, like, the newsletter, you know, I started in late 2022.

309
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I didn't release the deep dive until 2023, February.

310
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So because I just got started on something and kinda scratching my own itch on the whole, like, wanting to write something, and it morphed, 'cause I knew it was gonna change probably over time.

311
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That's how it became a thing. Not, but not because I, I started knowing I wanted to write deep dives. Yeah. So it just morphed over time. So I think anyone get started and kind of pursue your curiosity is always...

312
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Just, 'cause, like, the thing... I always go back to the Compare stuff, which is-No, consumable is content.

313
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But like, [laughs] the thing is, like, if you can do something and you learn and win, even if it's a, quote-unquote, "loss"- Mm-hmm... like, that's the goal for my stuff. So like you do a podcast.

314
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What's the worst thing that happens? You had some good conversations with people. Cool. So like that is like I will do that again and again because looking back on it, I wouldn't find it to be a waste. Yeah.

315
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Same with the writing of newsletter. I wouldn't find it to be a waste to publish a newsletter. These are ideas- Worse thing, you got better at writing. Yeah, exactly. You get better at writing.

316
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I wanted to publish these things, these ideas I wanted to be out there anyways.

317
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And so even when I've created content around, like my MBA experience, I still get people to comment on a video I made about my MBA experience from like years ago, 'cause I just wanna get that out there, and I knew some people would find it interesting, and they were t- it was four years later from that, and I still get responses to that.

318
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Well, which is really interesting actually with your YouTube channel. I was, I was checking it out. Um,

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you've got like a hundred twenty, twenty, hundred twenty-two videos I think exactly, and most of them, a- about half of them have like under 100 views. A few of them have- Yeah... thousands of views.

320
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But a- again, it's like the same thing. It's like do the thing. Worst case scenario, you get better at doing the thing or you meet people. Yeah. But yeah.

321
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Um- Well, yeah, and then I end up doing videos for someone else 'cause I had that. It's like, yeah, there's... You never know what- Yeah... comes from that. Um, I, I think that's a great place to end it.

322
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So where should people find you? The easiest place is probably Twitter, I would say. [laughs] But e- what I'm focusing now is Village Lane. So let's just, we'll start with that as well.

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VillageLane.io, focusing on building community for, uh, petty community of startup founders, but I'm very active on Twitter, so JustinGordon212, because that's the boiling point of water. That's why.

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Very strange, but that's why. Wait, why? Why is that? It's like the whole one degree actually makes a difference- Oh, okay... idea. Yeah, yeah. One degree lower than that, you're not boiling. One degree more- No motion.

325
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Exactly. Yeah. So that's why I have that, if people don't know that. Perfect. Um, cool. Well, this has been the Creative Spotlight Podcast. Our guest has been Justin Gordon, and I have been and shall remain Francis Sear.

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I will see you next week. [outro music]