Here's how to turn your content into revenue, without feeling salesy
How solopreneurs can turn feedback, DMs, and comments into a revenue flywheel without feeling salesy
I started my career in product engineering at one of the largest energy companies in the world. The work was good, technically interesting, and completely disconnected from customers. I knew something was missing, I just didn’t have a word for it yet.
I found it at a group called 1 Million Cups, an entrepreneurial community that describes itself as a dolphin tank rather than a shark tank. Sitting in those rooms, listening to founders present their ideas and field questions from strangers, something clicked.
Sales is problem solving with another human.
You don’t have to persuade anyone to buy something. You just show up where your customers are, talk honestly about the problem you’re solving, and let the people who recognize themselves in that problem find you.
That’s why I reached out to Orel and asked to share this post with you today. Most solopreneurs are builders who started with a problem they faced themselves and whether they build in public or in private, at some point they have to sell the solution. That’s the part most technical founders haven’t built a system for yet. It’s what I spent 15 years and over $100M in B2B revenue figuring out. And it turns out the system looks a lot like what the best builders are already doing…they just haven’t called it that.
The Thing Most Solopreneurs Miss About Sales
When you share your journey you think of it as authenticity. And it is. But it’s also something more specific than that.
You’re showing potential customers that you’ve felt the same pain they’re feeling right now. That you didn’t theorize your way to a solution…you needed it. When someone reads your blog and thinks “hey, I’ve been struggling with exactly this,” that’s the first moment of customer engagement. You’ve confirmed there’s a problem they want solved, and you’ve done it before you ever asked them for anything.
The way I think about it: you’re prescribing the problem before you diagnose the solution. Most founders flip this. They lead with what they built and then try to convince people they need it. The builders who compound do the opposite they name the friction so clearly that customers self-identify before the pitch ever starts.
Friction is the signal. It’s what your customers will pay to remove, and it’s what your product roadmap should be built around. The founders who find it are the ones who ask the most specific questions and actually listen to what comes back.
The smart builders listen for the friction.
I Learned This the Hard Way
I work in industrial sales. We sell large pumps for heavy operations, medium ones for mid-scale applications, smaller ones for specific process needs. Not glamorous. But it’s where I learned every sales lesson I’ve carried forward across 15 years and over $100M in B2B revenue, including the most expensive one.
We had a customer I’ll call Firebird LLC. We’d built a real relationship with them over months and growing traction, several large pumps running well in their operation. Then their business started to scale down and they needed to move to a medium option. That’s where I stopped listening.
Our competition had two medium pump options on the market, a Pump 1000 and a Pump 1750. We only had the Pump 1750. Through several meetings with the customer we came to understand that the Pump 1750 wasn’t the right fit for Firebird’s operations. The competitor’s Pump 1000 was and we slowly lost the account.
The hardest part was how we lost it. Firebird told us directly, they named the product, described the specs, and said they would buy it from us if we had it. We could have built a new pump configuration wasn’t impossible. But I heard that feedback and filed it as a conversation rather than a signal worth acting on. I honestly thought we could make our Pump 1750 work, partially because I had to at the time. We did not have another option. I treated their clarity as context instead of as a brief.
That customer’s clarity was a gift I left unopened.
What I learned since Firebird is exactly what I want to share with you, because the mistake I made is the same one most solopreneurs make when their customers tell them what to build next.
Driver 1 — Customer Engagement: The Signal is Already There
Real engagement isn’t the golf game or the happy hour. Those build rapport, but rapport isn’t the same as signal. The engagement that feeds a flywheel is what happens when a customer stops being polite and starts being specific. When they tell you the exact workflow that keeps breaking, or the feature they’ve been waiting for, or the thing your competitor does that you don’t. That specificity is the signal. With Firebird, I was close enough to hear it. I just wasn’t treating it as something worth writing down and acting on.
The way I run the engagement driver now is simpler than most founders expect. Every meeting, email, or DM gets read as a signal, not just acknowledged as a response. I ask myself what problem this person is naming and what gap their question reveals. I write it down, because patterns only emerge when you can see them across multiple conversations. One customer frustrated by the same thing is noise, five customers describing the same friction in different words is a product brief.
The discipline that matters most: before you build the next feature check what the signals are already telling you. Most of the time, the answer to what you should build next is sitting in a reply you received three weeks ago and didn’t fully act on.
The engagement driver surfaces the ideas your audience already gave you.
Driver 2 — Improvement: signals only compound if you act on them
Most builders hear what their users say and keep building what they were already building anyway. Not out of arrogance (at least most of time 😁)… usually out of momentum. The roadmap is set, the next sprint is planned, and the feedback gets filed somewhere it will never be opened again. That’s the pattern that stalls the flywheel. Hearing the signal is the easy part. The hard part is treating it as an instruction rather than an observation.
The way I think about the improvement driver: every product release is a test, and the results come back through usage, reviews, and the DMs you weren’t expecting. What matters is what you do with them. After every launch I look for two things specifically. What did customers push back on, because that tells me either the problem wasn’t as clear as I thought, or the solution didn’t land the way I intended. And what did customers ask about that I didn’t cover, because those questions are usually features I didn’t think to build or adjacent problems I didn’t know existed. Both of those are signals worth acting on. Neither of them shows up in your original plan.
The builders who compound aren’t the ones with the best initial ideas. They’re the ones with the shortest loop between what they hear and what they change. Firebird handed me that loop clearly. The Pump 1000 conversation was the improvement driver working exactly as it should a customer telling me precisely what the next version of our product needed to be. I heard it. I just didn’t treat it as the most important item on my backlog. That’s the mistake.
The builders who compound are the ones with the best feedback loops and the discipline to act on what comes through them.
Driver 3 — Re-Engagement: The Customer Who Told You What They Needed is Still There
The person who replied to your post six months ago describing a problem they couldn’t solve… they still have that problem. Time passing doesn’t make friction disappear. It just makes it easier to assume someone else solved it, or that the customer moved on. Usually none of that is true. The window is still open. You just have to knock.
Re-engagement is the discipline of going back. Not with a pitch, but with the thing they told you they needed. That’s a fundamentally different motion than sending a follow-up email into a cold thread. You’re not restarting a conversation you’re closing a loop that the customer opened and you could not close at the time. When you ship the thing someone named six months ago and go back to tell them, that message lands differently than any outbound you’ve ever sent. They remember asking. They know you listened. The trust that took months to build gets activated in a single reply.
The re-engagement driver also works beyond the original customer. When you build what your audience asked for and talk about it publicly (in a articles, a Note, a DM to the people who raised their hand) you’re evangelizing a solution that already has demand behind it. You know they need it because they told you.
With Firebird, I had the exact conversation. They named the Pump 1000, described what it needed to do, and told me directly they’d buy it from us. It took close to a year, but we built it. The re-engagement is happening now, we’re working to win that account back. It’s an uphill battle because we waited too long. But the conversation is alive again precisely because we finally shipped what they asked for.
Who in your user base has already told you what to build next and have you shipped it yet?
If the answer is no, that’s a listening gap. The fix is going back to the conversation where they told you exactly what they needed and treating it as the most important item on your backlog.
When You Put the Three Drivers Together
This is what I call the Revenue Flywheel System. This is the system I use to help technical founders build our their sales process for growth. It’s build on 3 Drivers that compound when they run together:
Customer Engagement — staying close to the people in your world. To listen.
Improvement — using the signals you collect to build sharper, more specific, more useful things. Every pivot is the improvement driver working correctly.
Re-Engagement — going back to the people who told you what they needed, with the thing they asked for. Closing the loop.
I’ve watched founders and solopreneurs run this system without ever calling it that.
Orel is one of them. He started building an AI article outliner, a tool he believed his readers needed. His readers told him they weren’t struggling with articles. They were struggling with Substack Notes. He didn’t defend the roadmap he’d already committed to. He listened to what his audience was actually asking for, pivoted, and launched WriteStack directly into the gap they had named. The product that exists today isn’t the product he set out to build. It’s the product his audience told him to build and there’s a meaningful difference between those two things.
That’s the flywheel running the way it’s supposed to. Not as a framework someone handed him, but as the natural result of staying close to his audience, acting on what they said, and going back to them with the thing they asked for.
The solopreneurs who compound their revenue are the ones who listen the best and act on what they hear.
Action Step
Go back through your last 30 days of e-mail, DMs, and comments.
Find the three most specific pieces of feedback you received, the ones that:
Named a problem
Described a struggle
Asked a question that shouldn’t need asking
Write them down. Then ask:
“Have I built anything in response to these signals or have I kept building what I was already building?”
That gap between the signals you’ve collected and the action you’ve taken is where the flywheel stalls. Close it.
Are you ready to go deeper than just knowing your weakest driver? The Revenue Leak Finder runs an audit on your current pipeline and shows you where deals are slipping and the 3 steps you should take today to fix them. The first 20 are 75% off.
Find me at engsales.substack.com
 | A guest post by
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The content-to-revenue gap is where teachers especially get stuck. They post brilliant free lessons all day, then feel weird the one time they mention they sell something. The selling has to live inside the content, not get bolted on at the end. How do you coach people through that first awkward pitch?
The awkward pitch is a structure problem, not a confidence problem. If your free content tells someone what to do, the paid thing just has to do it faster or do it for them. Then the pitch is one line: here’s the shortcut. No throat clearing, no pivot. I run a free reading list that feeds a $17 diagnostic. The handoff only works because the free piece already earned it. The people who felt it ask for the next step themselves.