Dear founder,
We often joke in entrepreneurship about founders having to wear many hats. But I think that metaphor is wrong. It's not about swapping hats. It's about growing entirely new heads.
Not just the cover of the head — the head itself. A new brain that thinks different, speaks different, prioritizes different. And somehow, these heads are all attached to the same body. It's less of a mad hatter situation and more of a Medusa situation. Multiple perspectives, multiple personalities, all trying to navigate a world that treats each one differently.
I was on a consulting call recently, and we got into this topic of focus shifting and dealing with multiple projects. The founder I was talking to was struggling with something I see all the time: they were migrating from a successful consulting practice into building a software business, and nothing was working the way they expected. Their focus was off. Their priorities felt wrong. And despite having years of professional success behind them, they felt like they were starting from scratch — except worse, because their instincts kept leading them astray.
This is a situation a lot of founders find themselves in. You're coming from a salaried position, or from freelance work, or maybe you've been running a small agency with a low headcount — something personal, something you've built relationships around. And now you're trying to build a software business. A completely different animal.
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Here's what I've come to understand about this transition: one of the biggest threats to the success of a new software business is encumbrance with parts of the old one. And I don't just mean time commitments or scheduling conflicts. I mean the mental models, the assumptions, the instincts that served you so well before — they might be actively working against you now. The very things that made you successful in your previous career could be preventing success in this new one.
Let's talk about one of the big ones: urgency and immediacy. This is something that, particularly when you work on a low-touch, highly automated software as a service business, comes at a completely different time and in a completely different shape than what you're used to.
When you're freelancing or consulting, and your client has a problem, it tends to be a big issue. No matter what it is. As long as they don't express a problem, you're doing okay. You're doing all right. But the moment something goes wrong, the urgency and immediacy of these problems is palpable. And it often self-amplifies when you interact with a customer — because when a client tells you something is wrong, you promise them to fix it, you go about it, and it becomes a high priority.
Why? Because you have so few clients. Retaining any one of them is probably the most important customer success mission you might have. When you have five or ten people paying you four thousand dollars a month, acquisition all of a sudden is not even required — unless you have churn. You can coast. You can breathe. You can focus entirely on serving the people who are already paying you.
But the moment you try to project this approach onto a software as a service business, something that has a quite varied and distributed customer base by design, everything breaks.
In SaaS, particularly in low-touch, highly automated SaaS, churn is inevitable. Retention is never guaranteed, for many factors, most of which are completely outside your control. People's businesses change. Their needs evolve. They get acquired, they pivot, they go under. That makes acquisition not something you do when somebody churns — it's a constant act, a constant part of your operational presence that needs to be dedicated to that effort.
This distinction is often hard for people coming from an agency or consulting world to internalize. Acquisition needs to be this permanent funnel that you dedicate significant effort to on a very regular basis. Because it's always needed. It always needs to be running like a well-oiled system. In low-touch businesses in particular, due to that lack of urgency or immediacy when the product is purchased or sold, you can't wait for a trigger to start looking for new customers.
And here's where it gets even more challenging.
In the consulting world, you likely built your business on relationships. Your personal network. Your reputation. Word of mouth from satisfied clients who became champions for your work. When you needed new business, you could pick up the phone, send a few emails to people who already knew you, maybe grab lunch with a prospect. Quality over quantity, right?
That playbook doesn't translate to low-touch SaaS. Not even close.
The efforts to get a customer's attention, to get them to self-sign up and try your product — they usually go on deaf ears. People are quite hard on products they've never seen before, or on companies they've never had a positive business experience with in the past. You will find that outreach without a personal network, or rather outreach that outgrows the personal network or the established network you might bring from prior business experience in the agency world — it's a completely different beast in many unexpected ways.
There's nothing to connect with. Nobody there. Nothing pre-existing. The old playbooks, the high-touch playbooks, the connection and relationship playbooks — they are completely unworkable in this new context.
So when you try to go for quality instead of quantity — when you approach cold outreach or content marketing or paid advertising the way you used to from that more interconnected world, maybe a world in which you had way more reputation, maybe a world in which you had much better connections and much better understanding of how people purchase than what your software product and its specific new customer base offers — you find that the things you want to do don't work.
And the things you don't want to do? Those are exactly what's required.
Who wants to write email templates to start sending cold to thousands of companies in the world? Who wants to draft blog posts that won't rank for three, four, six months? It's not a very enjoyable activity. These tasks feel tedious, impersonal, and frankly beneath the level of sophistication you've developed in your career. But they are something you need to do, because the long-term effects of systematic, scaled outreach are significantly more important than what a quick lunch date or a catch-up meeting can provide in a low-touch SaaS environment.
The irony is that the very activities that feel wrong — that feel like a step backward from your refined, relationship-based approach — are often exactly what moves the needle.
This is where the cognitive dissonance comes in. And I want you to really sit with this, because it's uncomfortable.
At the moment you become a founder, you have to strike this weird balance. On one hand, you're building something completely new that nobody has ever done in exactly this way. You have to make assumptions. You have to believe in yourself to be right to a quite significant degree. Without that confidence, you'll never ship anything. You'll second-guess yourself into paralysis.
On the other hand, you also have to assume that all the things you know to be right from prior jobs might not only fail to work for you in this new role, in this new circumstance — they might be actively preventing success. Because you're instinctively, from experience, in a kind of default mode, deprioritizing the things that need to be done right now.
I think this is what Paul Graham writes about in his essays on doing things that don't scale. Because the scalable stuff — the stuff that does scale — is meant for a different kind of business. Or in your case, probably a different size of business.
You will be able to have those enterprise deals eventually. Those conversations, those month-long sales cycles for your software company. Once you move upstream and get back into that enterprise world. But for your first hundred customers or so, you don't know what's going to work. Because if you did, somebody else would know too. They would have already built the business you're building.
In a sense, you have to develop this cognitive dissonance and be able to feel it, experience it, without falling prey to either of the extremes. You don't want to fall into overconfidence. You don't want to be overconfident that what worked until now will always work again. But you also don't want to lose track of the fact that your experience in prior roles has given you insights into customer psychology that you can still apply. They might look different now. But the learnings, the underlying psychological rules — they're still the same.
There's another layer to this that I want to touch on, and that's the concept Geoffrey Moore laid out in Crossing the Chasm. Because in all cases, you have to deal with this problem.
There is always a chasm between early adopters and the early majority of adopters. And when you're starting out, you'll likely find yourself surrounded by innovators and early adopters. But here's what you need to understand: these people do not function like the later-stage majority or the laggards that you might have worked with in your consulting days. Not even close.
In fact, the higher your jump-off point — the more senior you were at that point when you started building this side business or going into entrepreneurship — the harder it will be to understand the reasoning and idiosyncrasies of people who are experiencing their own professional life from a much more early adopter perspective. The way that things are done, the way that things are talked about, will be wildly different with these customers.
And even if you're aiming at enterprise customers eventually, their perception of security and safety is different. There's what's commonly expressed with the Lindy effect: things that have been around for a long time will likely be around for an equally long time in the future. And its inversion: things that have only been around for a short while are prone to end up being abandoned or ending quickly in failure.
That perception is very hard to fight with a customer in the later majority stage. They want proof. They want references. They want to know that you'll be around in five years. But an innovator? An early adopter? They'll likely ignore all of that. They might even become champions for your product within those same organizations, fighting against the institutional resistance.
The way you speak to an innovator, the way you get an innovator interested in your company, is so significantly different from how you talk to a laggard adopter. If you're used to selling to established enterprises, used to that later-majority communication style, you might find yourself completely out of sync with the people you're actually able to reach right now. You're speaking a language they don't respond to, addressing concerns they don't have, and missing the things that actually matter to them.
So what's the way out of this?
The way out is by allowing yourself to feel that experimentation is not just an optionality — it is a requirement. Because you will not know which things will work that worked before. So you have to try them and see if results are still possible. If you're calibrated right.
Maybe what you need is to spend a significantly bigger chunk of your time on different kinds of marketing efforts, sales efforts, product development efforts, documentation efforts — all the things you might not consider to be the most important ones, whatever that might be for you. Maybe those activities are actually a more aligned way forward for the current state you're in.
You always have to remember: if you're building something new, the situation is new. The thing you're building is new. The surrounding circumstances might be the old ones, but they're adjusting to a new presence. Everything is in flux, and your assumptions need to flex with it.
All this to say: when we migrate from one profession to another, when we start our businesses on top of our experience in the field, maybe the methods that used to work aren't that smart to use anymore. We should embrace not only the insights of people who have shown us that they've done this before — learn from founders who've made this transition successfully — but also embrace that uncertainty and new approaches are part of the deal. They're not obstacles to success. They're the path to it.
You're not just switching hats. You're growing new heads. And that's uncomfortable. That's disorienting. It might even feel like you're losing your identity, like you're becoming someone you don't recognize. But it's also exactly what the situation requires. The good news? Those heads are still attached to the same body. Your experience, your judgment, your understanding of people — that foundation is still there. You just need to let it express itself in new ways.
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