Growth In Reverse

AUDIO - GIR 009 v1
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[00:00:00] Chenell Basilio: Someone at Meta was actually sharing around your article and you got a bunch of new subscribers with Meta. com email address at that point. And so you must have just seen that and been like, Oh wow, this is like going viral inside of the company.

[00:00:12] Aakash Gupta: To actually convert these people, you have to send a lot of paywall to content.

One of the areas I've tried to differentiate is like just having more content. Where most of these guys, they'll do 52 deep dives while I do 88. It's really about my intentional strategy around trying to build a durable business. A business that I can do for 30, 40 years. Frankly, I love this lifestyle.

It's a lot easier than being a VP of product.

[00:00:35] Chenell Basilio: I tell people that all the time who are just getting started. I'm like one channel, just one. Stop trying to be everywhere.

[00:00:41] Aakash Gupta: I'm telling you right now, if you don't get any value after this, just email me and I'll refund you. If we're going to charge like 100 times more than the newsletter.

How he can actually deliver a hundred times the value.

So Akash, welcome to the show. Thanks so much for [00:01:00] having me. I literally read like almost every single one of your newsletter issues as they came out. I was like one of the earliest fans, so really excited to be on the podcast.

[00:01:10] Chenell Basilio: Wow. Thank you for that. I appreciate it. I remember, uh, interacting with you a couple of times, but I didn't realize how much you were growing.

I felt like it was like underground growth and then all of a sudden you like exploded with this huge newsletter.

[00:01:23] Aakash Gupta: It's very niche audience. So sometimes people are like, Oh, really you, you write? I was like, yep. You write a lot.

[00:01:32] Chenell Basilio: That's amazing. Um, yeah. So at the time, just to give people context, um, I wrote a deep dive on you back in.

I think it was March of 2024, so last year, uh, at the time you had 105, 000 email subscribers and now you're at 153, 000, uh, with over 350, 000 followers on social. Honestly, the followers was about the same. I mean, it was, it's definitely grown since then, but it was about the same back then. Um, so I, I'm excited to get into [00:02:00] that and like how you're growing now, but, um, In the deep dive that I wrote, I did talk about a couple of things that I picked out from your growth story.

And, um, you, a couple of the ones that I thought were the most interesting were the collaborations that you were doing and the optimizing for the internal share. Um, were those two like big, uh, pieces of your growth at that point, or did I miss something?

[00:02:22] Aakash Gupta: Yeah, those are critical. I think that, uh, collaborations, the study was done on, uh, Twitch creators where Twitch themselves were trying to figure out which creators are growing the fastest.

What are they doing? And basically when they ran their multilinear regression, they looked at it and wow, like the number one factor is how many collaborations they're doing. So that insight always stuck with me, which is that, okay, like. If I want to reach people who read newsletters, maybe I should collaborate with people who write newsletters and similar strategy with the [00:03:00] podcast.

Maybe I should collaborate with people who host podcasts and that the approach is really that the types of people who consume content in one area, for instance, social media, like LinkedIn may not be the same as those who consume content and sub stack. And so trying to reach people where they consume content is the pillar of my collaboration strategy.

And I've never forced a collaboration like I've actually rarely ever just sent out like a message like, do you want to collaborate with me? It usually comes out of some sort of organic friendship that I'm trying to build with another creator where at some point they'll be like, well, we've had dinner together.

When are we doing something together? And then we'll write a newsletter or something like that. So that's always really fun to do because it's just, it keeps you excited, keeps you connected to other people doing what you're doing. So I love the collaboration. And then for me, the internal share about 50 percent of my content is a really good fit, not just for product managers and growth people, but for developers, [00:04:00] designers, executives, founders, other people within tech companies.

And so for me, as I think about how do I kind of grow out of my niche, like any creator naturally will grow out of their initial niche of product and growth for me, the internal share is enabling a lot of that. And it's also causing me to reconsider then. Well, what do I write about? What how, what length do I write about?

How do I talk about certain roles? And before I might've had a very PM centric point of view over time that has kind of broadened.

[00:04:27] Chenell Basilio: I like that. That's so interesting. Um, and just to give context for anybody listening who hasn't read or listened to the deep dive, uh, the internal share, you came across this in one of your posts, you had realized that someone at Metta was actually like.

Sharing around your article and you got a bunch of new subscribers with all of that, like meta. com email address at that point. And so you must have just seen that and been like, Oh, wow, this is like going viral inside of the company.

[00:04:52] Aakash Gupta: I love that. Yeah. Substack kind of allows you to just get an email every time you get a free subscriber and up until about [00:05:00] 60, 70, 000 subscribers.

I just left that email on so that I could. See the types of names coming in the types of times of day, uh, and it was fun seeing that. That's

[00:05:09] Chenell Basilio: so fascinating.

[00:05:10] Dylan Redekop: Wow. So like 70, 000 emails in your inbox of a new subscriber coming in basically.

[00:05:15] Aakash Gupta: Yeah. Over like three years or something. Okay. It was just like the only good part of my inbox, you know, That's

[00:05:21] Chenell Basilio: fair.

That's totally fair. That's awesome. Based on that, like, how do you, Diving into that just a little bit more because I'm trying to think for the people who don't have a B2B newsletter, like is there a strategy or a way to think about this kind of content that you think somebody else could use that doesn't necessarily have like a product growth newsletter or something like that?

[00:05:40] Aakash Gupta: Yeah. Well, in particular, like if you're studying product growth, you're studying like how I grew the paid subscriptions because, you know, in the newsletter deep dive that you wrote, you assumed a 5 percent growth rate. 5 percent conversion rate, right? That conversion rate is everything. Like, are you actually getting 5%?

Are you getting two and a half percent? Seven and a half percent. [00:06:00] The headline number for the article will vary wildly just based on that one percentage point and to drive paid subscriptions. First of all, you need to think about, you know, who has a lot of disposable. Typically, people working at corporate jobs tend to have the most disposable income, you know, bigger corporations, especially corporations whose stock prices have appreciated as much as met as even more.

So and so in terms of thinking about how to grow a paid newsletter. Understanding and learning more deeply who my potential buyer actually is and then creating content for them. And, you know, as even within the space of product and growth content, I could create a lot of content for small and medium sized businesses.

There would be a certain flavor of content, or I could create more content for these larger companies. And what I noticed, especially while analyzing my internal shares, because it's such an important metric, is that when I tailor that content, For those enterprise people who have a lot of income, especially in areas like [00:07:00] California and New York, the sub stack also shows where those people are coming from.

That's when I see really, really good conversion rates into those paid subscribers and those paid subscribers tend to retain a lot better. So for me, it was really latching on to figuring out where are the number of internal shares? How are those internal shares converting to paid and how well are those paid subscribers retaining?

I can tell when

[00:07:22] Dylan Redekop: I was researching as well for this that you've really kind of honed in on the expensing, you know, the expensing aspect of this, uh, to the point where you've created a document like a Google doc that's called expensing product growth that just shows a whole bunch of different ways or for product managers, product leaders, for designers, for engineers, which people can email their boss and say, Hey, I've, I've signed up for this newsletter and I think it's going to help me in my job.

Can I expense it basically. So can you walk us through like. Okay. When you decided, like, this is probably a good idea and I need to do this.

[00:07:52] Aakash Gupta: Yeah, so if you think about the big bad killer of subscription newsletter businesses, it's really churn. [00:08:00] And so if you think about what drives churn, a lot of it is who are the subscribers you are acquiring and how are they paying.

And the subscribers you acquire, if you can get them to pay for their company credit card, They're not going to feel the pain every 15 a month that they get charged or every 150 a year that they get charged. And so the subscriber you gain who is doing it on their own, maybe for six months, they're reading it a lot and they want to pay, but.

Then they're going on vacation. They might just cancel it while they're on vacation for a month, but then never resubscribe versus if they're on a corporate account, they're not going to compare it to their Netflix bill. It's just going to be one of the benefits. I expect my next employer to give me one more tactic to negotiate on at the very end of my negotiation.

Oh, and I want a 500 learning and development budget. And then this 150, it feels like nothing. Right? So it's really about my intentional strategy around trying to build a durable business. A business that I can do for 30, 40 years. Frankly, I love [00:09:00] this lifestyle. It's a lot easier than being a VP of product.

So I want to do this for a lot longer and trying to acquire those customers then that are the stickiest looking at my retention rates. When I have a corporate credit card, you know, the retention rates are basically double. So if we're looking at like. Double retention rate, way less churn, half as much churn after 12 months, after 24 months.

Now I have that data as well. Then I want to acquire more of those users. So it's really that intentional strategy of trying to increase my retention rate as much as possible.

[00:09:30] Chenell Basilio: So how do you know if it's a corporate credit card? Is it just like Amex? Mostly,

[00:09:34] Aakash Gupta: um, you should be able to, uh, like stripe or wherever you look at, we'll help you look at these things.

And then you can also, for me, a lot of times, a lot of my corporate accounts, there'll be bought under a group discount. So I can also look at people under a specific discount code.

[00:09:49] Chenell Basilio: That makes

[00:09:50] Aakash Gupta: sense.

[00:09:50] Chenell Basilio: I was like, how do you know that? That's so interesting. A little rabbit hole question on my end. Um, but no, that's awesome.

That's. It's [00:10:00] fascinating just to see how well you use the data that you have and are able to take that and turn it into like growth and media and content decisions. Essentially.

[00:10:09] Dylan Redekop: I've got one more question just about on the subject of monetization. I know we were going to touch on this a little bit later, Chanel, but I'm really curious because you are so focused on, um, um, You also do run ads, correct,

[00:10:20] Aakash Gupta: in your newsletter?

Yeah, so, interestingly enough, I basically have three sort of business lines. I have the paid subscriptions on the newsletter. So those people, they're never going to see any ads. Then I have the free ads. free newsletter, which whenever advertisers want to come around and make paid content free for the free subscribers, they can.

So that's basically the main ad in the free newsletter is this idea of kind of buying out the paywall so everybody can enjoy all of the content. And then I have ads in my podcast. So that's my main focus and relationship with advertisers.

[00:10:56] Dylan Redekop: So is all the free content that you publish? Let's call it [00:11:00] free, quote, unquote, free content.

Um, is that all then like sponsored content

[00:11:03] Aakash Gupta: in general to actually convert these people? You have to send a lot of paywall to content. I don't know anybody who's actually gotten to like a high conversion rate without regularly sending Emails to your free list and what I try to do. I try to read a lot of other Product and growth newsletters.

And I look at what the quality level about how many insights do they have? And I try to put that much always free, but for those people, which again, now I'm narrowing my audience quite a bit, who like even deeper content, even longer content than I have content posts that pay well,

[00:11:35] Chenell Basilio: I read in one of your posts, I can't remember where it was at this point, but that you have about 2, 500 words free and then.

Potentially 2500 plus more words after the paywall. Is that right?

[00:11:45] Aakash Gupta: Yeah, that was exactly what I was doing right around March of 2024 when you wrote that. And then since then, I launched the podcast in like August or something like that. And with the launch of the podcast, I realized that like my volume of content [00:12:00] going out into the world is so high that I actually have reduced the size of those posts.

So now it's some more like 1200 words before the paywall, 1200 words after the paywall.

[00:12:10] Chenell Basilio: But even, even so, I think if someone reads that much of your content, they're probably way more interested and likely to want to pay eventually, because like, if they get to the end of the article, they're probably like interested in that concept or the topic that you're referring to.

And I can see that. Being a high conversion rate for sure

[00:12:27] Aakash Gupta: depends on the topic. Depends on the article. I feel like sometimes I put the paywall too low. You know what I mean? Like I just give away too much of the article that I'm like, I wrote this banger article and then I look at the conversions and I'm like, ah, that was disappointing.

So it's one of those things that. That's the metric that really matters for me is like acquiring new subscribers and preventing unsubscribes. So those are what I'm looking at after an email send.

[00:12:50] Chenell Basilio: Interesting. And then I guess going over to some other growth stuff, like the collaborations that you were and are still doing.

I, I found this, I, I forget who I was [00:13:00] researching, um, but I found Maya Voer and I was like, oh, interesting. She had like 3000 subscribers on her substack at the time, and then all, all of a sudden in her like, feed on Substack, I saw. Your name and her name collaborating and I was like, wow, okay, this is super interesting because you had over 100, 000 at the time and I was like, this is going to be really big for her potentially, like to be able to get her name as a byline on your newsletter with all of those same, I mean, you guys are talking to a similar audience, like it might be a different, uh, angle, but I think that that's so fascinating.

Like, how do those, how do these collaborations come about? I know you said you were, you know, you're potentially friends with these people at a certain point. Um, Beforehand, but is there like, are you always looking for collaborations? Like, how does I'm curious?

[00:13:46] Aakash Gupta: Yeah, literally, it was the friendship angle. I think, uh, so I started by seeing her on my LinkedIn feed.

Then eventually I commented on one of her posts because she had a bunch of good posts. She sent me a connection request with. [00:14:00] Some question or something like that, which I answered turned into a dialogue. At some point we were like, we should write a newsletter collab together. And so that came about, I think probably Maya suggested it.

As you said, I think like the subscriber difference was a little high, but. I was more than thrilled to I've been reading her content, her content, super high quality. So for me, I definitely am keeping my eye out for smaller creators who are really good in my niche, because if I can showcase them early, if it can be like, Oh, a cautious newsletters where I saw them, then, you know, I'm showing that taste that curation.

And that's my goal.

[00:14:34] Chenell Basilio: Do you strive to do like a certain number of those every quarter or anything?

[00:14:38] Aakash Gupta: I have no goals. Um, I actually create my entire content calendar and everything like that. Just based purely on myself doing everything. And then if collaborations come in, that's totally fine. Like the cool thing about collaborations and by not having like a clear publishing schedule, like your average newsletter, like every Tuesday they send like, you know, X piece of content for me, like I can [00:15:00] just send any time of day, any day of week if a collaboration piece comes in.

Usually the amount of time I'm putting into a collaboration piece is a around half, and so it means that I can actually put out another piece coming up. More quickly and so one of the areas I've tried to differentiate where I've been a very crowded niche for paid newsletters on product management and growth is like just having more content where most of these guys they'll do 52 deep dives while I do 88 so I've just managed to squeeze in some more so hopefully I've added some value for you.

[00:15:29] Chenell Basilio: I like that. I think more creators. Need to do collaborations, and I've talked about this quite a bit recently, but, um, it's just, I don't know, it's such a underrated thing. I think YouTubers know it, like you said, Twitch streamers know it, but I think the, the newsletter space writers, uh, they can really grow faster using collaborations and it's just building those relationships, like you said.

[00:15:50] Aakash Gupta: Yeah, I think that, uh, realistically, like my metrics are not that different when I do a collaboration in the short term, but I think in the long [00:16:00] term. What it's building for me is I'm being able to tap into like other people's areas of expertise. Usually if we collaborate, that's like something they're like deeply an expert in.

So on the longterm, it's raising like the quality bar of the content that I can talk about, uh, because I'm not just tapping my own expertise, being able to tap others. Um, so I really like that. You mentioned, uh, starting the podcast last

[00:16:21] Dylan Redekop: year. Talk to us about how that has. Um, I mean, obviously it's adding that much more work to your plate.

So how has that benefited the newsletter as a whole? Like, has it been a positive thing? Um, talk to us about a little bit about that.

[00:16:34] Aakash Gupta: I would think about it in three ways. And I think Chanel wrote about like my funnel. So I was thinking about in terms of the top, the middle and the bottom funnel. Right? So in the top funnel, if you think about LinkedIn, LinkedIn's.

favorite format to promote is video right now. So like one of the easiest ways to tell how much LinkedIn likes a particular type of content is to look at, uh, your likes to impressions ratio. So for on an image post, my likes to impressions [00:17:00] ratios, almost always around a hundred on video. It's like three, 400.

So they're, they're just pushing out these videos that. People don't like compared to the other content three to four times more heavily. So, uh, you get a good sense, like how much priority they're putting on that in the algorithm. So certainly what I've noticed is that as soon as I started posting like shorts, like, I don't know if you noticed, but in about two weeks ago, LinkedIn updated the way they present shorts.

So before they used to present shorts with these ugly gray boxes on the sides. Uh, now they just present it full screen, which means it's even taller. It like literally takes up your whole home feed to see one of those TikTok short videos. So I've noticed, uh, that the creators growing fastest on LinkedIn, we're posting a lot of shorts.

I was like, how is this person growing faster than me? And then I'm, I analyze very carefully, like, okay, first of all, they're putting up more content than me instead of just a daily text or picture post. They're also added in these shorts three to four times a week. So I did that myself and. [00:18:00] Instantly starting to see much better follower growth on LinkedIn.

You mentioned my follower growth on LinkedIn slowed down. It's sad, right? But this is one of the things that has sped it up. So that's the top of the funnel. The middle of the funnel for me is like how many free newsletter subscribers I have. And the podcast is probably a negative. To free subscribers, because every podcast episode two week, I'm sending to my email list.

And so I get a ton of unsubscribes on those, but to grow my podcast at the beginning, I just view it as a necessary investment. So I've told myself like, yes. Probably for the next year I'm gonna have to email my newsletter my podcast and it's gonna cost me a lot of free subscribers But I'm just gonna have to bite the bullet on that one to bootstrap and start this podcast And then there's bottom of funnel paid subscribers before I used to spend my entire time my entire life For these paid subscribers, creating the best content for them.

Now I have a second job a podcast, so it's probably been [00:19:00] a ne negative there as well in terms of like the quality and quantity of posts that I can create for paid subscribers. And so where I need to win it back then is kind of that advertising revenue that I'm getting in the podcast. So I'm slowly doing that.

[00:19:14] Chenell Basilio: So you started the podcast in August. September.

[00:19:18] Aakash Gupta: Yes, I think August, middle of August last year.

[00:19:21] Chenell Basilio: Because I was getting ready to ask you on Substack, you went from posting like eight or nine posts a month to now 10, 15, 20 posts a month. And I was like, Whoa, this is a lot. So that's mostly the podcast then you think?

[00:19:34] Aakash Gupta: It is the podcast entirely. Yeah. Well, I've also been trying different strategies in my content calendar. I figure my content calendar is ultimately my product. Like. The topics that you write about, that's so important, at least student business I'm operating. So I've just started treating that as a product.

So, uh, in like, uh, I would say something like, I don't know the exact timeline, but for basically like two or three months last year, I did a test where I did like [00:20:00] very high quality. So I did like one a week deep dives and then for two or three months I actually went more for quantity where I did two a week deep dives.

And so I've been trying sort of different tests with my content calendar to understand what is the trade off on open rates versus free unsubscribes versus paid subscribes because each time you send a paywalled email you have more opportunity for those paid subscribes. So trading everything off and trying to figure out the right mix.

[00:20:25] Chenell Basilio: That's a lot of content.

[00:20:26] Aakash Gupta: Yeah,

[00:20:27] Dylan Redekop: it is. And so when you said trading off, um, quantity for quality, so were the two a week, were you doing like just not shallow, but like just less of a deep dive, like less content, less, um, research or how, like, how did you decide how much to scale back those

[00:20:42] Aakash Gupta: for two a week?

Basically what I did is I hired a team to help me. So hire. So basically about half my time for a typical piece was allocated to infographics. So just creating, you know. Social shareable graphics that are going to work and so hiring a [00:21:00] designer immediately free up a lot of my time, although they aren't exactly me.

So there is, it's not like I get all of the time back. I have to write. It works best when I write a really good spec for them for the infographic. So that takes, I don't know, almost half the time probably. But so I save like a quarter of my time there. Because you do a lot of thinking on your canvas when you're designing a graphic and you're the content creator.

Getting the designer, that's one element. And then what I decided is like, I love this model, this hub and spoke model. I think Matt Gray talks a lot about it. For me, it's like, you know, your hub. Is your newsletter. And so if I want to keep like a really, really high content quality bar, I'm going to always be the one writing the newsletter, researching the newsletter.

But what if somebody else is creating, for instance, my promotional pieces about it? What if somebody else is optimizing the SEO for it? So that is what I did. Next is hired people to work on the SEO element, which is like an optimization. You just have to do at the end of every post, right? For two [00:22:00] to three hours.

Now I don't have to do that. And the option of basically, you know, the way I do my LinkedIn posts is those infographics that I create. I create a, I'll create three infographics per newsletter. And we mostly draw from the newsletter for those LinkedIn posts. Whereas before it might take me like an hour to create each one of those LinkedIn posts now, somebody else does that and I can just edit.

So all in all, you know, able to shave off places of time here and there, but. I look at the pieces and I do say, okay, there's no, um, real way to replace just thinking about something deeply for seven days. If you think about it deeply for three and a half days, that's going to be the level of marination and bakedness of your insights.

[00:22:43] Chenell Basilio: I feel that for sure. Uh, yeah, the deep dives are definitely much more challenging to get out. at a faster clip. Uh, it just doesn't work in my case anyway. Um, that's a lot of content. So three infographics per article.

[00:22:58] Aakash Gupta: Yes, that's what I've been [00:23:00] doing for a long time now. I would say like maybe like a year and a half or so.

[00:23:04] Chenell Basilio: And so those turn into your LinkedIn content as well as the podcast clips. I'm just like scrolling through your LinkedIn now looking at this. I'm like, Oh yep, I see it. Okay. Yep. This makes sense. So, okay. So infographics. Do you have someone helping with the podcast, like editor?

[00:23:19] Aakash Gupta: Yeah, of course. The podcast is a crazy amount of work.

So I have two sort of, or three roles on the podcast. One, editor. Two, packaging. So creating the sub stack post, creating the YouTube description, creating the episode show notes, creating the infographics. All of the myriad things that go out of that, and then shorts.

[00:23:39] Chenell Basilio: You have quite the team now.

[00:23:40] Aakash Gupta: Unfortunately, I really wanted to just be me, but then I launched the podcast, so. And then I was, yeah, so I had to hire a team.

[00:23:49] Dylan Redekop: And you wanted to sleep as well, right? Sleep is important. Yes,

[00:23:52] Aakash Gupta: yes, I have two kids, so. I just, I also have like. A limit on the amount of time I work. I used to have my entire career, I think, until I [00:24:00] had kids.

Thankfully to my wife, who's been my partner this whole time, I used to just work more than other people. That was like one of the key ways I got ahead. Now I can't do that.

[00:24:08] Dylan Redekop: Yeah,

[00:24:08] Aakash Gupta: I

[00:24:08] Dylan Redekop: can feel that. Um, you touched on SEO. I think that'd be a good, a good direction to go because, um, in a post that you, you wrote, I guess, towards the end of 2024, kind of a year in review style post, you'd mentioned that things that had worked for you in the past.

Like Twitter, like LinkedIn, um, had really slowed in the past year for growth and you're focusing more on SEO and sub stack you called out as kind of the two places you're focusing more. So, um, we talked a little bit about what you're doing with sub stack, but what, what are you doing with SEO and how have you seen that?

Impact your growth.

[00:24:41] Aakash Gupta: Yeah. So just so people know, like Substack has the recommendations network. This is like how like Lenny and Gergely, I probably mispronounced his name. I've grown so fast. I do the same thing

[00:24:50] Chenell Basilio: all the time.

[00:24:50] Aakash Gupta: Yeah. Yeah. They have like, they're number one in business and tech and everybody just recommends them.

So they're just going like crazy. Right. So I don't have like nearly [00:25:00] the flywheel. Like I think Lenny, like every month or two, he's like, here's another hundred thousand. Like, I'm not like, I don't have that many recommendations, but I do have like for like recommendations with some of my friends. So they do help.

Um, and in particular between LinkedIn and X, you mentioned, you know, LinkedIn, interestingly enough from like a trackable site visits. Yes. Way down. But like from my own like impressions, plus like what I can see in terms of like free and paid subscribers, probably not really down much. So if anything, what LinkedIn has done is they've.

Instead of showing my content to people who are just tangentially interested is only showing it to people who would be super and which for me is fine. So LinkedIn hasn't really slowed down my business, but X has where like X before it was a platform you could actually grow on. Like there are very few people nowadays growing on X who aren't like building in public or aren't entrepreneurs or like have a political content.

So I'm neither building in public or have. political [00:26:00] content. So, and the thing I noticed was to improve my retention rate amongst paid subscribers, I needed to only talk about stuff that I had expertise in. And so I really cut out a lot of the top of the funnel content that Chanel mentions in that piece, actually.

So like all my viral Twitter threads, I don't even write those anymore. So first of all, Mostly pre kids, so had time to write those from like 11 p. m. to 1 a. m. Now don't even have that time, but second of all, just like, yeah, it doesn't help my retention rates to be talking about stuff I'm not an expert in and so I don't have much top of the funnel content So X is evaporated like literally used to be like hundreds of paid subscribers a month Thousands of free subscribers a month to like almost like zero ish numbers when you in count for especially they're not liking links either so it's like There's no trackable traffic that's any value of me.

So X is the real one that I need to make up. So sub stack recommendations. That's one component. And then SEO is the one that I've really started to tap [00:27:00] into now. You know, we all think search must be dead. Like personally for me, I do very little searching. Everything's done through perplexity and chat GPT, but other people are still searching.

Um, and so just optimizing for Google, like the very basic stuff, like having a target keyword. Putting that keyword in your title of your post, in your subtitle, in the first paragraph, in a couple headings, refreshing your content. So your best performing SEO pages, they'll degrade over time if you don't refresh them.

So refreshing your content, adding in internal links to key things, looking at the other people like two through 10, or even one through 10, if you're not number one, like what do they have on there and adding more of that type of content into your post. So all of those things are. My main SEO strategies.

And then surprisingly, the podcast is really good for SEO. So basically once people are guests on the podcast, they often link to it from their newsletter. And so you get really good backlink. Um, so those are the main things I'm doing on SEO.

[00:27:58] Chenell Basilio: You're definitely growing [00:28:00] an SEO. I can, I'm looking at like a drafts just to see, um, I can see the intentionality behind it.

It like really starts to pick up. Recently, beginning of last year, essentially. That's, that's fascinating. And you're just continuing to do like the best practices. It doesn't sound like you're doing anything like extraordinary.

[00:28:18] Aakash Gupta: Yeah. I don't think there's any magic to SEO besides just actually doing the basics.

I mean, if you're already a good writer, if you're not a good writer, you're kind of screwed.

[00:28:27] Chenell Basilio: Yeah, it's fair. So the podcast is helping just because people are linking to the episode from their newsletter. I can see that. Especially if it's

[00:28:36] Dylan Redekop: somebody with some You know, reputable, where the backer is so much more valuable.

[00:28:41] Chenell Basilio: Um, are you doing anything with, um, Substack Notes?

[00:28:44] Aakash Gupta: I wish I was doing more. Like, Substack Notes doesn't, uh, connect into anything. So I use, like, Buffer, for instance, to manage, like, my LinkedIn, X, threads, Instagram, Facebook, all of that. It's just [00:29:00] managed through this and it can't. So I would have to manually like do it all.

Like I'd have to just take it out of buffer and put it into sub stack notes. So the podcast, I'm bootstrapping the podcast, growing that thing. And so that's the only thing I go through the extra effort of posting my trailers on sub stack notes. But I know it would work. Uh, I think it is a credible growth strategy.

There are a lot of people in my niche who are using it, but it's just a kind of an ROI for me, uh, focusing on LinkedIn. Like I almost like this idea of like one ICP, one go to market channel. And so. If I just had to choose one ICP product manager, one go to market channel, LinkedIn. And so anytime I'm trying to like make a prioritization decision about where to focus, I just think about that.

[00:29:44] Chenell Basilio: I tell people that all the time who are just getting started. I'm like one channel, just one, stop trying to be everywhere. And they're like, but it would do so well if I posted it across different places. I'm like, yes, sure. You can have it auto posts, but like, do not spend time anywhere, but one channel. [00:30:00] So that's, it's exciting to hear you say that.

Moving on to just the, the paid newsletter in general. Like I don't know a ton about this cause I have not gone the route of a paid newsletter as much as I wanted to in the beginning. Are you, is there anything you think you would have done differently when you launched the paid side? Then you did. Um, like what you know now, would you go back and change anything?

[00:30:22] Aakash Gupta: Oh, gosh. So the story of me doing that was like literally somebody, one of my friends are just like, you have to turn it on and he's like, you have a huge list. It's growing fast. Uh, Substack will just automatically paywall your archive and your archive will start to print money for you. And I was like, really?

Okay. Won't there like be some sort of trade off somewhere? And so, you know, just turned it on. That person was right. Like I'm starting to pay subscribers are trickling in just based on this idea. And there are some big paid newsletters that still do this. That like the free list, they get the full article.

But if they want to check it a week or two later. It's paid. [00:31:00] I think it's a cool strategy. That's how I started, but then I realized like, oh, there's this way faster way to grow your paid list, which is You send a paywalled article to your free list. And then people who are really enjoying the article convert to pay.

And so then I started writing these multi part, uh, newsletters where I'd have like four topics. And so two of the topics would be free and then two would be paid, but that didn't work as well as one time I wrote. A one topic newsletter where half was free and half was paid. And I was like, Oh, boom, like finally figured it out.

Like this is how you actually grow your paid list. And so I slowly walked into product market fit around understanding how to grow a paid list. Um, and then I've really just. Triple down on what works, which is send a lot of that type of content, but somehow keep your free users still reading. So we talked about buyouts, for instance, the podcast, there's no paywalls on the podcast, different things like that.

So that your free list is [00:32:00] still getting a lot of value and I try to always compare it to like other free lists. Like you want to give more value than those other free lists if possible. And so subjective value to you, like I also believe that it's really easy if you just create for yourself. And you have some, like, judgments about what is good and what is bad, because if you're trying to be super politically correct, it's just, it's gonna be very hard to write good content, so, in my own mind at least, like, I have this judgment, like, okay, this is good content, this is bad content, and I'll try to write better than that content, so that has been my overall strategy, if I had to go back, um, I think, like, a couple things I would do, like, number one, try to avoid Predetermining like everything in advance that I'm going to send this article on Tuesday, this article on Thursday, like really keep it open for experimentation.

Cause as you heard in my story, like the things I thought were going to work before I started versus the day I started versus a month later, we're completely different. And so not having the calendar, I think really helps. And I was probably still overly predetermined in that it took me a long time to.

actually [00:33:00] notice those shifts, even though I told the story relatively quickly in terms of evolution. So that's one area I would fix. The second area I would fix is for a paid newsletter, try to add something new to each piece. So only recently, about the last year or so, I realized this, which is like, I try to always interview some new people, or I try to create a new framework, or I try to collect some new data for a paid newsletter.

You don't want to just to be like, what's behind the paywall is my opinion. There are some paid newsletters that do well like that, but that doesn't work for me.

[00:33:31] Chenell Basilio: That's interesting. So I think one of the more recent episodes, Dylan and I were talking about exclusive content and this is what's making me think of this is you're essentially creating content that doesn't live anywhere else.

Whether you were. You know, curating a different data set and then adding that into the paywall, um, or vice versa. And it's, it's actually interesting because now I'm realizing like you're putting that behind the paywall and then people will share that, but the people they share it with can't read it unless they buy.

So,

[00:33:58] Aakash Gupta: well, you can always forward [00:34:00] an email. So that's the cool thing, right? And that's, I think a good. feature functionality of the design is like they can see if their friends forwarding it to them. And we do hear lots of cases of like, yeah, my entire product team is on your newsletter. I'm like, really?

Cause we have one email address from your domain. It's like, yeah, that's set to auto forward to the whole product team. So, you know, there's easy hacks around it, but in general, you know, for the good hearted Samaritan, who wants to support the work of an independent creator, they can do that.

[00:34:29] Chenell Basilio: That's interesting.

Okay. So you have like different data sets that you're pulling in different interviews. Is there any other types of content that you try and put into that new area?

[00:34:38] Aakash Gupta: So that's for me, like it's interviews are the best source. So for instance, recently, if you Google on Google, actually, there's a lot of search for this Google product management interview.

And you look at the first three results and they were the first result will say they have five interviews. The second result will say they have seven interviews. The third result will say they have 10. Well, what is the actual truth, right? And so that's something I can [00:35:00] go talk to people who recently interviewed at Google.

And I can put it behind the paywall and I can say, Oh, there's actually X number of interviews. These are the interviews that you're likely to see. These are the exact questions that people I talked to were asked. That's valuable.

[00:35:13] Chenell Basilio: That is valuable. Yeah. Um, huh. Okay. I can see that. This is, it's just bringing me back to like, so I was, I did some SEO work like years ago and it's just like, It's all coming full circle because this is the stuff you used to do back then.

And I'm like, Oh, okay. It still works.

[00:35:29] Aakash Gupta: Yeah, it does. It's what academics do. If you think about it, like they're not going to publish in a journal unless they have something new to contribute.

[00:35:37] Chenell Basilio: That's interesting. Um, this one got me. So on the topic of the paid paid newsletter, I saw that you have a subscription guarantee that I had.

I've never seen this before with a newsletter and maybe that's just me missing it, but you say that. I promise this paid newsletter essentially will have a more than 10x ROI on your career or you get your money back. I love it.

[00:35:57] Aakash Gupta: I'm happy to, happy to refund anybody. Like [00:36:00] almost nobody has ever told me like, Hey, your content, it wasn't good.

Like give me a refund. I have to deal with all the customer support requests. I get plenty of people who like the day they subscribe, they're like, Oh, I didn't mean to subscribe or something like that. I have to deal with all those refunds. I've never had a refund like this. Uh, so yeah, it's a really easy guarantee to make.

It's really just copywriting. If you think about it just for that sales page, like there's no way for you to measure 10x ROI or for me to measure it. But if you think about it, 150 a year average product management salary. In the world is something like 100, 000. Most of my readers are in the US or Europe.

Their average product management salary is something like 200, 000. 150 to have an impact on you. That's 10x. I need to increase your pay from 200, 000 to 201, 000. I'm pretty confident I can do that. It's a very small percentage increase on your salary. And every PM who works, they get like between like a three to 10 percent yearly.

Increase. And so for them to attribute, you know, I [00:37:00] got five this year. Cause I was reading a cautious newsletter, I think is pretty easy.

[00:37:03] Chenell Basilio: No, I like the framing. I had just never seen it before. And I was like, Oh wow. That's fascinating.

[00:37:08] Dylan Redekop: It's like added, added peace of mind, right? Like the very worst. If this has brings me zero value, I can ask for a refund.

That's it's like a, it's just a deal closer.

[00:37:17] Aakash Gupta: Exactly. And unless people start using it, I'll just keep that.

[00:37:22] Chenell Basilio: Yeah. Why not? It's just giving them a, yeah. Like you said, the peace of mind so that they're probably, I have to wonder what you're like, I'm sure there's no way to measure this, but like what the conversion increase was or like the speed to conversion, you know, like how much faster are people subscribing to the paid side of things because they're like, well, it's a no brainer.

Like I can get my money back.

[00:37:41] Aakash Gupta: I should test that. Yeah.

[00:37:44] Chenell Basilio: I don't know if you'd be able to, but. That's interesting. If you, if you're able to let us know.

[00:37:48] Aakash Gupta: I could just remove it from that page or alternatively, I could just tell people like, Hey, I'm telling you right now, if you don't get any value after this, just email me and I'll refund you at the top of the next email or something.

Yeah.

[00:37:59] Dylan Redekop: I was gonna say, do you [00:38:00] ever mention it actually in a, just before a locked part of the article, a gated part of the article where it's like, if you're worried about giving me all your money, never getting it back for, uh, like I have a guarantee essentially mentioning that. Have you ever tried that?

[00:38:12] Aakash Gupta: I should, maybe I'll do that on Saturday's piece.

The, uh, But the thing I do offer, and I've tested this, is whether I should have a free seven day trial. And so, I do have a free seven day trial out there. And I think, I mean, you can read the whole newsletter if you want over seven days. Yeah. Yeah.

[00:38:28] Chenell Basilio: Yeah. I saw that. I subscribed to your newsletter when I was doing the deep dive.

So I think now me going back, I don't have that option anymore because you can't give it an extra time.

[00:38:38] Aakash Gupta: Interesting. I do have a lot of people who I. Who when they churn, I try to like, I email people like, Oh, you can meet with me if you want. And I can just do like a normal coaching session and like, Oh, this has to be a couple of things.

And so people do take me up on that. And a lot of times they will say, yeah, I do plan to resubscribe. And I don't know how many of those people actually have only probably one or two have, but people often [00:39:00] aspire to.

[00:39:03] Chenell Basilio: That's interesting. I found certain people will unsubscribe from my newsletter and I find that.

You know, they might see it through a recommendation from someone else, and then they resubscribe, and then they're like more active than ever. And I'm like, okay, that's interesting. I kind of like that. It's a good use case for recommendations.

[00:39:18] Dylan Redekop: For sure. I'm curious what, um, like 2025 is, is upon us now. So what, what do you see as like a huge opportunity for you in 2025 for the newsletter?

[00:39:28] Aakash Gupta: Great question. I think that, uh, One of the most important things I'm trying to do is continue to grow that B2B segment. So, like, recently just had, like, 50 seat purchase. Like, love to see a 50 seat purchase. Also, like, an annual purchase, right? And, like, that's, like, the best thing you want to see. So. Driving more of those purchases where like, you know, we have a head of product and they're trying to uplevel their product organization.

So they just buy everybody one of these. There's a lot of people who do stuff like that. If you think about it, a lot of times they'll pay even more. So one of [00:40:00] the competitors in my space is called Reforge. Their courses are often at like a thousand dollars for a course or like two to 3, 000 a year for an unlimited seat.

Which a lot of tech companies currently have memberships of they're willing to pay two to 3, 000 for access to course material. If I can try to kind of elevate my content quality, maybe even I package some of it as courses. So that's one of the tests I'm planning on running in 2025 packaging more of my work into like unique courses, and then maybe even hosting those like a standalone courses that you could potentially purchase too.

And so thinking about. Courses and education and competing and kind of this B to B segment of career content is one area that I think is a pretty interesting growth area. The second one for me is really tripling down. Like my podcast is so young. Like if you think about my newsletter, when I went full time on the newsletter, I had probably spent like three or four years on it.

I'm just like five or six months into the podcast. I'm, I want to set it up for, you know. Three or four years from now, it is like a [00:41:00] huge business as well. And so thinking about accelerating my learning loop there. So what I have now, I mentioned to you guys, like we have people on shorts, packaging, editing with them, just like I've approached my entire newsletter, always coming up with really good tests, tests that we have really high conviction in tests that we can somehow measure that we can articulate a hypothesis and then look at over several podcast episodes.

Okay. Did having, for instance, the trailer. At the beginning of the YouTube episode, like, interestingly, we just looked at that test this afternoon. So we looked at, like, the last 10 videos, five with trailer at the beginning and five without the average view duration was quite a bit higher without the trailer, but the average views.

Was quite a bit lower. So if you actually look at total time watched, it was a little bit higher with the trailer. So then you're kind of like confused, you know, you're like, you don't have full clarity and signal. So we haven't like kind of made a conclusive decision on that and we'll just continue to test into it.

But continuing to look at things like that, continuing to make smart [00:42:00] decisions and uplevel the technology really around the newsletter, around how we're doing SEO is the other big opportunity.

[00:42:06] Chenell Basilio: I like that. Are you. Do you have plans to expand? I know like SEO is SEO, but you know, perplexity coming in and like chat GPT, like I'm even seeing subscribers come from those places and I'm not really focused on SEO like that.

So I'm wondering if there's anything different you're doing thinking about those channels versus typical Google or.

[00:42:24] Aakash Gupta: Yeah, I see some traffic from there, but it's like much less than Google and. None of them turned into free or paid subscribers really for me, so it hasn't been a good source of quality traffic.

I think it's part of the AI Armageddon, really. I think it's like a very sad fact, though, that, uh, they're just gonna start to eat up a lot of traffic that, uh, independent sites like ours used to actually get. Um, because they just summarize the information and yeah, they're not really good vehicles for subscribers.

So it's pretty sad. I think I want to like clarify my thought process on how to take advantage of it in light of that. Uh, and I don't know that I have a good answer, but I do know that like a lot of my content that ranks for [00:43:00] Google search also for the same queries and chat, GPT and perplexity does really well.

And I'm sure you probably see that too. Right. Like, I think if you search my newsletter. Um, and I think it's kind of the same thing for Chad Chubuti's mind. They'd probably like, look at your article if you ask them about my growth. So I think that, uh, right now I'm just optimizing the same as Google until I learn more.

[00:43:23] Chenell Basilio: It's fair. Yeah. I was thinking the same thing. I just wasn't sure if you had any like insider knowledge on these new platforms that you're looking at.

[00:43:30] Aakash Gupta: I wish. Yeah.

[00:43:33] Chenell Basilio: That's interesting. Yeah. The podcast I think is going to be one of the ways that you kind of stand out a little bit more as well. Thank you.

We'll Because, you know, like I said, that's also exclusive content, if you will. Nobody else is interviewing the same people at the same time with the same questions. So, um, that's going to be a good way for you to stand out moving forward too.

[00:43:50] Aakash Gupta: Yes. Although the more I study podcasts, the more I'm learning that like the same podcast guests appear on every single podcast, especially guests that [00:44:00] drive views.

So it's interesting.

[00:44:02] Chenell Basilio: Yeah. But it's your personality. I think that will stand out above more above the other ones. So I

[00:44:08] Aakash Gupta: hope so. I hope so. Yeah. I need to continue to improve my craft there. I feel like

[00:44:13] Chenell Basilio: yes, us too. So

[00:44:15] Dylan Redekop: yeah, ongoing process, learning process. Do you have any plans on, um, any kind of new channels or new types of content?

Cause you just launched the podcast in 2025 and 2024. Um, give any of anything else that you're thinking of doing in 2025 that you'd see as being either fun or experimental or anything like that.

[00:44:33] Aakash Gupta: Yeah, it's like kind of like every six months or so, I want to try to launch something new. So I'm not at like the Mark Liu, like monthly level new startup.

I think that's amazing for me, probably every six months or so. So before the podcast, I actually self published a book on Amazon, for instance. So that was like a fun sort of experimental process to do that. Uh, as I mentioned with my biggest opportunity around course, I think that's kind of the next big sort of experimental opportunity for [00:45:00] me.

Some sort of. Self paced course with heavy discount for newsletter subscribers type of package product. And so that is on my mind, like figuring out we have like basically with the team, we're thinking about like between three different ideas, which idea is going to like be the best topic to cover and then making sure we have the right content behind it and making sure that, you know, if we're going to charge like a hundred times more than the newsletter.

How he can actually deliver a hundred times the value in this course. So, uh, that's like my, probably my highest, uh, conviction hypothesis of a new product or new direction. But really, I feel like I have the right to main business lines. So whenever like a prioritization decision comes up, if the course is going to take something away from the newsletter or podcast, I'd rather not do it because.

I feel very high conviction on both of those two and want to just, they're, they're all the returns to these types of businesses happen way down the line. Like the work you're doing now, it pays off like four years down the line. [00:46:00] So I want to make sure to kind of put in that grunt work now.

[00:46:02] Dylan Redekop: Yeah. Plant that tree now instead of, you know, 20 years from now, right?

As the saying goes.

[00:46:06] Chenell Basilio: Amazing. That sounds great. Um, I think a course would do well for you. You already have the content. You already have the. Um, interviews that you could pull in even, um, I think that would do quite well. Excited to see that come to life on your end. Other than that, I mean, wrapping up, like where can people find you?

Where can they find your work? What's the best channel? It sounds like LinkedIn, Substack, podcast.

[00:46:27] Aakash Gupta: Yeah, exactly. Anywhere, anywhere. Akash Gupta, uh, the website, like I have this, I haven't fixed my like website. I'm stuck on Substack. And once you choose. One domain redirect. They're like, Oh, you can't have more than one.

We're not going to write the 301 redirects for you. So I'm just like stuck on www. news. akashji. com or you could just do product growth. com one day, maybe I'll have to buy some better domain. I don't know. Um, but that's where I'm at right now and all the social media.

[00:46:57] Chenell Basilio: I have to imagine at this point with your [00:47:00] subscribers and the people on the platform, they'd probably make an exception.

No?

[00:47:03] Aakash Gupta: Maybe they would. If they would, I would buy like a better custom domain like today. Worth reaching out, worth reaching out to them.

[00:47:11] Chenell Basilio: Well, thanks for coming on the podcast Akash. Really appreciate it.

[00:47:15] Aakash Gupta: Thank you so much for having me. I was really excited when I got your email.

[00:47:20] Chenell Basilio: I thought you'd be a great guest.

I think there's a lot for people to learn based on, you know, the paid side of things with your, uh, paid content and just you're putting out a ton of content. So I think it's the prolific nature of it is, is interesting. So appreciate you coming on.

[00:47:34] Aakash Gupta: My pleasure.