We just spent six weeks migrating our email newsletter from Beehiiv to Substack. Within one day of going live, I realized I'd made a mistake and had to course-correct. This episode opens up what happened, why it was a mistake, and more importantly—the framework for deciding when to pivot versus when to persevere. Because I've always struggled with this: am I being frantic and erratic by changing course? Or am I being stubborn and falling into sunk cost fallacy by staying? Here's what went wrong: Day One on Substack, I realized the audience is mostly creators writing for other creators, the growth engine requires building another Twitter-like feed (the exact treadmill email newsletters were supposed to solve), and I risked diluting my most valuable asset—my list—with the wrong audience while having no analytics to detect it. I break down the exact questions I ask myself at these decision points: What core problem was I solving? Why was it really a problem? Does this actually solve the underlying issue? What will make me regret this in six months? The lesson: perpetual pivots destroy progress, but stubborn perseverance does too. Learn how to course-correct strategically instead of emotionally, and be aware of your own tendencies—I tend to pivot too quickly, maybe you stick too long.

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Welcome to Repeatable Revenue, hosted by strategic growth advisor , Ray J. Green.

About Ray:

→ Former Managing Director of National Small & Midsize Business at the U.S. Chamber of Commerce, where he doubled revenue per sale in fundraising, led the first increase in SMB membership, co-built a national Mid-Market sales channel, and more.

→ Former CEO operator for several investor groups where he led turnarounds of recently acquired small businesses.

→ Current founder of MSP Sales Partners, where we currently help IT companies scale sales: www.MSPSalesPartners.com

→ Current Sales & Sales Management Expert in Residence at the world’s largest IT business mastermind.

→ Current Managing Partner of Repeatable Revenue Ventures, where we scale B2B companies we have equity in: www.RayJGreen.com

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We just spent six weeks on a project that, within one day of going live, I realized I had made a mistake and had to course-correct. And I'm going to share what that was today, like just kind of open up on what the situation was, why it was a mistake. And more importantly, what I'll want to share is the lesson of when to pivot and when to persevere.

Because whenever we face these decisions, we're like, "All right, do we backtrack? Do we undo this? Do we stay the course?" And for me, it's always been a challenge to try to determine: "All right, if I change this and go back, am I just kind of like being frantic? Are we running like this erratic business and constantly switching shit and now we have to go back and dada da? Maybe I should just stick with it. Or am I being stubborn and just staying the course and falling into kind of like sunk cost fallacies?" So I'll share how I approach this because the way that I've been doing it has been really helpful to me.

So the situation was we migrated our email newsletter from Beehiiv to Substack. We have about 6,000 subscribers, 7,000 subscribers. We get really good engagement. The deliverability is good. We get solid opens, good clicks when we ask people to click through, but it's intended to be a value-add. It's not a... it's a marketing nurture tool value-add type of thing more so than it is client acquisition and direct response for leads.

So we were looking for a way to get better engagement, right? Like to take that engagement that we get through the email and actually turn it into more engagement. Like, hey, you can like posts on Substack. You can comment on posts on Substack. So rather than somebody just read the email and email back and say "Hey, cool email," or read the email and tell me when they see me in person, "Hey, I loved your last email," they could actually just like click through and have that conversation there. And I thought, "Hey, that would be really cool." Like engage with our readers more. And also get feedback, right?

The other thing behind Substack was it was a place in my mind where we could consolidate content into one library. You know, we have this podcast, we have the YouTube channel, we have the email newsletter, we have other popular posts or tweets from elsewhere. And I thought, "Hey, let's get this into one place so that if somebody comes into our ecosystem and wants to explore it more, we make it easy for 'em," right? So Beehiiv in my mind... much more email oriented. Good tool, nothing... it was just an email tool. And I was looking for something that was more comprehensive and integrated and allowed more engagement.

So we set everything up. We got Substack set up, we got the thumbnails taken over, we got the email list ported over, domains, blah blah blah. We tested it. We went through everything. And Day One, which was literally yesterday, my email goes out. And I realized like there was like this... ah shit... like a few things that we didn't know. Now there were some things that we knew, right? Like we tested the platform and I have some friends that have been using it successfully and I got feedback. So there were some things that we knew going into Substack.

We knew that the sign-up process had some friction. Like when you sign up for somebody's newsletter through Substack, you're probably gonna get like three windows, right? Instead of just like "put in your email and go to the page," you're gonna put in your email and then it's gonna refer some other publications and then it's gonna ask you to download an app and then it's gonna take you to the publication. Like whatever those steps are, there's typically more than one and a little bit more friction than you want in a newsletter. But you know, we knew that.

We knew that the analytics weren't very good. Like compared to Beehiiv, the actual engagement metrics beyond opens and likes... there's not a ton there on Substack. We knew, as we were setting it up at least, we learned: Okay, you can't segment audiences. There's no automation. There's virtually nothing that you can do in Zapier or with APIs or anything like that. So if you're using it as part of a funnel, probably gonna have some limitations. Again, knew this. But they all factored into the decision as I'll share here in a second.

Users get asked to download the app. So they kind of get... Substack wants to grow Substack, right? So the intention is if you grow, they grow. But ultimately their goal is to grow Substack. So they don't want people just to read your publication; they want people to get the Substack app and start experiencing Substack more broadly, right? So they're gonna push people: download the app, look at these other readers, sign up to these other newsletters. And they do some of that promotion. You know, and so like one of those things, they refer other publications. Sign up for... they're reading your newsletter, they're gonna say "Oh hey, you like this one? Maybe you like some other ones." Which, maybe not the end of the world, but again, it promotes the Substack experience more than it does your own newsletter. And that one we kind of figured out as we were signing up.

Now the big one that really hit us was on Day One. And so as we found these things out, my desire to migrate had declined. But it was like, "You know, we set it as a project, we made this decision, let's see this through. And there's nothing here that's a huge surprise." So the challenge was, it goes live and I got a couple messages from friends, from people that said, "Oh hey man, I got... interesting... I got peppered to download the app or this and that." And so some of the feedback that we kind of knew... we had users actually tell us.

But the big thing was: the strategy for Substack right now is that they're migrating to their own... basically to become their own social media platform. And once you get going and once you go live, you realize: "Oh hey..." like you start looking through your own feed on Substack because there's a feed, right? So it's just like... I'm one of millions... I'm one of million creators on there. And in my feed, I'm scrolling through my own feed and I realize... Holy shit. Like this is... like half of the audience here are creators writing for other creators. Like within my feed it's like: "How to grow on Substack," "How to write for this," "How to get your first 25 subscribers," "How to do this." And I talked to a friend of mine and said, "Hey, do me a favor." And we look at it; his is basically the same thing. And we realize that the audience on Substack is a whole lot of people who are just creators, creating for other creators. There's nothing inherently wrong with creators creating for other creators. But the challenge is: if your audience starts growing on Substack and your audience is other creators, I'm now not writing for my audience, right?

So if part of the reason that you go to Substack—which I'll get to in a second—but if part of the reason that you go there is to leverage its organic growth engine and take advantage of the growth that happens within Substack, and then you realize while you're there that the vast majority of the users are creators creating for other creators... Now, I mean there's some other people, right? I mean there are some decent-sized publications there. But in terms of leveraging the growth engine, I'm going through the feed and I'm like: "Oh god. Like this is just another social media platform where the biggest people here are just teaching other people how to use the social media platform." Which was a huge turn-off.

And the strategic concern is: If your audience starts to grow and it's not the right audience, and you're using any of that data and growth to inform your content strategy, then you start... you run the risk of creating for the wrong people. And then ignoring or alienating your actual group, right? So that was one of my thoughts.

And then the second piece, the big one, was that if you look at any of the content on "How to Grow on Substack," the overwhelming majority of it is: "Oh hey, use this notes feature." Which is basically Twitter, right? So they've created their own Twitter within Substack and it's like, if you tweet a lot, if you write good notes, if you write good posts, then your stuff's gonna get seen and that's how you're gonna grow on Substack.

And I thought, "You know the last thing I want on the fucking earth right now is yet another social media platform that I have to waste... not waste, but I have to invest time into posting and engaging and liking and commenting and creating more content for and doing this." It's like... which, I mean that's just like any other... that's that treadmill of content creation is the very reason that you create an email newsletter. So that... or any owned media, right? Like any owned media where you take your audience and make sure that you, the creator or the business, own the audience. That LinkedIn doesn't own it. That X doesn't own it. That Facebook doesn't own it, right? Like you create these assets so that you own it. And otherwise what you have to do is keep creating content for these platforms and it's like a treadmill. You know, because the post that you put up today is gone tomorrow.

Well Substack's basically created that engine within their newsletter tool. But the newsletter was the asset that I designed to get off the treadmill content. So I looked at this and I just went like: Combined with the other things that we already knew going in... and looking at the audience... and realizing that leveraging the growth engine is probably gonna require creating more tweet-like content... and then the risk is significantly that you can't... that you create for the wrong audience... and then within that you can't segment the audience... and the analytics suck, so determining whether it was the right audience... I got this put together and I was like: "Ah shit."

And literally the same day as it goes through and I get some feedback from readers, I get my own experience in going through, and I go: "Fuck, I've got a decision point." Right? And here, what I've really been more diligent about is taking advantage of a strength of mine which is: I move very quickly. But not allowing it to become a weakness, which is: you perpetually pivot. Right? Because if you perpetually pivot, you're gonna constantly... you're gonna destroy your progress. Because all real progress happens after momentum has been built. And if you're constantly changing then you're constantly starting over, which means you're constantly staying in the area that has the lowest return. The best returns come later, where things start to compound. And if I'm changing directions all the time, I'm staying in the beginner lane, right?

So recognizing that, I go: "Okay, I've got to get more disciplined about being quick to move, but not having that turn into a weakness." And at this moment I got a decision to make. Like am I being rational, strategic, and making an informed decision and just moving quickly? Or am I being emotional and rash and should just calmly see this through and see how it goes and measure it and come back to it? And that decision point I think is what I hope is helpful here.

And the first thing I do in this point now is I pause. Like I stop, right? Like look, we're not gonna act right now. Like we're gonna just think calmly about this, objectively about this. I'm not gonna make a decision until I'm very confident that I'm making an informed, educated, non-emotional decision that's, you know, based on any number of kind of logical fallacies or broken thinking models, right? So the first thing I do is pause.

Then, lay out my options. And this is what I did yesterday. So, you know, I said: "Alright, what are my actual options here?" You know, and in this case, I can stay the course, right? Like I can stay where we're at, you know, run it for say 60, 90 days, look at what the results are and then make a decision then. Or I could say: "Listen, we've sent one issue through this new platform and I'm just gonna course correct really quickly." And you know, I laid out like a couple other options, but it really came down to those two things. So you know, I... Alright, so I've got my options.

Then the questions I start asking myself—and actually wrote these out, I plugged some of them into my AI thinking partner—like one question is: "What was the core problem that I was actually trying to solve with this change?" What was the real core problem? Not "what are all the benefits of Substack" or "what are all the problems of Substack" or "what are all the benefits of Beehiiv." It's: what was the core business problem that I was trying to solve? And in my case, it was faster organic growth. And you try to get that down to like one core problem. Like there's always a number of problems, but the more complexity you add in this, the easier it is to rationalize and justify the decision that you want to make based on an emotional bias. So like: one core problem. What was I trying to solve? And then the other question is like: "Why was that a problem?" Why was that a problem in the business, organic growth of the newsletter? Like what happens if you solve that? Or what happens if you don't solve that?

And in my case, it wasn't really a problem if I don't solve it. It was an opportunity if I do. Right? So I looked at it and said: "Okay if I can grow the newsletter organically, more aggressively and faster, there's some correlation to bringing in more business, like more credibility, more educational material out there." Like people that engage with my newsletter tend to at some point go, "Hey, you know what? I'm gonna explore this now." Like a lot of our sales and a lot of our booked calls come from people who've seen five, six, seven newsletters and said, "Hey, this one finally hit me," or "I've been reading this and you kind of struck a nerve." Right? So it's like, well if I have more people on that list, theoretically there's more people that are that are engaging with it and will subsequently grow the business.

The question I ask at that point is like: "All right, is this going to solve that?" Right? So you've got the core problem. You understand why it was a real problem. Is this actually going to solve the underlying issue? Not the growth issue, not the email subscriber, because I might solve that with Substack. But I also might get a bunch of other creators that just like the way that I write... and so it doesn't necessarily mean that it's my ideal clients or my target market or the people that I'm actually writing for or want to read my stuff, right? So does this solve that underlying issue? And in my case, no, I wasn't... I wasn't certain that it would, right?

And then the last question I kind of ask is... and this is a really important one... "What's gonna make me regret this decision in six months?" Either way. Like if I stay the course, stay on Substack and just stick with it. Or I pivot today and go back immediately. What's going to make me regret this decision? And I started listing reasons. And the number one reason that stuck out to me was: A diluted list six months from now is a huge pain in the ass, right? Like if I have... if I double my email subscribers but half of them are people that came from... that are not within my market... and giving me bad data... and I don't have the data tools or the analytic tools within Substack to understand who's joining or when they're joining or better engagement metrics... then I end up with a diluted list. That is the last thing... that is very dangerous to me. Like this is... your list is a really important asset. It's one of your most valuable assets in your business, I think. And a diluted list is not something that I want to run the risk of doing. So, I wasn't positive that I was gonna solve the actual problem, and it posed a risk now that I actually looked at it.

So I said: "We're switching. Like we're going back. Like, you know, sorry, this sucks, we invested time, energy, effort... but this is... we've got to go back. And what we'll do is we'll solve the underlying problem a different way. Right? Like we can address it some other way."

So the lesson for me, like the takeaways: You know, one is like just remembering: Perpetual pivots always... they destroy your progress. If you're constantly changing directions, you never give yourself a chance to build momentum and let things compound. And that destroys more businesses than I see actually get destroyed because people stay the course. That being said, stubbornly persevering and, you know, because of sunk cost bias and fallacies and all of that, also destroys your progress. So looking at this and recognizing: "Hey, you know what? Mistakes are part of the game." Like if you're gonna do anything in life, you're going to make some mistakes along the way. Like that's just... just fact of the matter.

So understanding: if I go this way, if I go this way, there's some... there's inherent risk. And figuring out how to course-correct in a logical, strategic way and not be emotional about it. And be aware of your own biases, like your own... your own tendencies. That, you know, maybe you're somebody that tends to stick with it a lot more. I tend to be somebody that would just pivot a lot more. And making those decisions more strategically—not frantically or not out of habit—that they are, you know, based on their situation. And handling them the right way.

Kind of working through some questions. Getting real... getting real honest with yourself about the problem that you're solving, why that thing is a problem, what does this really solve the underlying problem, and what's gonna make you regret this later on. Like that has really worked for me and, you know, candidly been a reason that we've stuck with certain things and changed others. And as of now, we'll be going back to Beehiiv and building our engagement metrics and better ways to engage our email list there.

By the way, if this resonated and you want to join the list, link's probably in the notes below. So hope this helps. Adios.