The night before our first hire started, I couldn’t sleep.
Not because I was excited, though I was. Not because I was worried about the work, though I was that too. I couldn’t sleep because the math had just become real. There was now another person whose rent depended, in part, on me making good decisions.
This sounds dramatic. It is dramatic. Anyone who tells you hiring your first employee is “just a step in the growth journey” has either forgotten what it felt like or never experienced the full weight of it. You go from being responsible for yourself — your income, your schedule, your mistakes — to being responsible for someone else. The transition is instant and total.
One day you’re a founder. The next day you’re a boss.
Those are very different things.
The Decision
Bruno and I argued about timing for months. He thought we should hire when we needed to. I thought we should wait until we could comfortably afford to. We were both right, which meant we were both wrong, which meant the argument went in circles until a client deadline forced the issue.
We’d taken on three new clients in the span of six weeks — more growth than we’d planned for — and the workload became physically unsustainable. I was writing content until midnight, waking up at six to run client calls, and spending weekends on strategy docs. Bruno was managing accounts, handling operations, and doing half the design work himself. We were both reaching the point where the quality of our work was beginning to degrade, and in a services business, quality is everything.
The math was tight. We could afford to pay someone a fair salary if two conditions held: the three new clients stayed, and we didn’t lose any existing ones. Both conditions felt fragile. Client retention is never guaranteed, especially when you’re a small agency without a deep bench.
We hired anyway. Because the alternative — burning out and losing clients due to declining quality — was worse.
What I Looked For
Our first hire needed to be a generalist. We couldn’t afford a specialist. We needed someone who could write decent content, manage a project board, communicate with clients, and not panic when the plan changed on a Tuesday afternoon. That last part was non-negotiable.
I interviewed about fifteen people. Most of them were fine. Competent, professional, reasonable. But “fine” isn’t what you need for hire number one. You need someone who’s genuinely adaptable, because at a two-person company becoming a three-person company, the job description is going to change every month. Maybe every week.
The person we hired — I’ll call him Alfredo, because that’s his name and he’d laugh at me for trying to anonymize him — stood out for a specific reason. In the interview, I asked him to walk me through how he’d handle a situation where a client needed a deliverable by Friday, the brief was unclear, and the founder (me) was unreachable for the afternoon.
Most candidates described a process. They’d check the project management tool. They’d review previous deliverables for context. They’d draft something and wait for approval.
Alfredo said: “I’d make my best guess, do the work, send it to the client with a note explaining my reasoning, and copy you so you could course-correct when you got back.”
That answer told me three things. He was biased toward action. He wasn’t afraid to make decisions without permission. And he understood that a wrong deliverable sent on time is almost always better than a perfect deliverable sent late.
He started the following Monday.
The First Week
The first week was terrible. Not because Alfredo did anything wrong. He was great. The first week was terrible because of me.
I couldn’t let go.
Every piece of content he wrote, I rewrote. Every client email he drafted, I edited to within an inch of its life. Every task I delegated, I checked three times. I was, in the most literal sense, paying someone to do work and then doing the work myself anyway.
Bruno pulled me aside on Thursday. “You’re going to break him,” he said. “And you’re going to break yourself. You hired him because you trusted him. Now trust him.”
He was right, obviously. But the gap between knowing you should trust someone and actually trusting them is wide, and it can only be crossed by doing the uncomfortable thing: letting go and accepting that the result might not be exactly what you would have produced.
I forced myself. The next Monday, I assigned Alfredo a blog post for a client, gave him the brief and the brand guide, and didn’t check on it until he submitted the final draft.
It was different from what I would have written. The structure was different. The tone was slightly different. Some of the word choices weren’t what I’d have chosen.
And it was good. Not good “for a first attempt.” Good. The client loved it. They specifically praised a section that I know I wouldn’t have thought of.
That was the first time I understood that delegation isn’t about getting someone to produce your work. It’s about getting someone to produce their work, which — if you’ve hired well — will be different from yours in ways that make the whole better.
The Mistakes
I made a lot of them in those early months. Here are the ones that mattered most.
I didn’t set clear expectations early enough. I assumed Alfredo would intuit what “good” looked like because I knew what it looked like. But my standards were in my head, undocumented and inconsistent. I’d approve something one week and flag a nearly identical thing the next week, and the only explanation was that my mood or my mental model had shifted. This is crazy-making for an employee, and I didn’t realize I was doing it until Alfredo, very diplomatically, asked me to write down what I actually wanted.
So I did. I wrote a style guide. I wrote process docs. I wrote checklists. The act of documenting my expectations forced me to examine them, and in examining them, I realized some of them were arbitrary. The ones that survived the scrutiny became our operating standards. The ones that didn’t were abandoned.
My second mistake was not giving feedback fast enough. When something wasn’t right, I’d sit on it. I’d tell myself I’d bring it up in our next one-on-one. By the time the one-on-one came around, I’d either forgotten or the feedback had lost its relevance. Meanwhile, Alfredo was repeating the same patterns because nobody had told him otherwise.
I learned to give feedback within twenty-four hours. Not harshly, not publicly, not in a way that felt like a reprimand. Just: “Hey, noticed this thing. Here’s what I’d suggest instead. Make sense?” Short, specific, immediate. The quality of his work improved dramatically once the feedback loop tightened.
My third mistake was the biggest. I forgot to tell him he was doing well.
When you’re running a startup, you’re constantly focused on problems. What’s broken. What needs fixing. What’s not good enough yet. This creates a selection bias where the only feedback you give is corrective. You notice the errors and miss the wins.
Three months in, Alfredo quietly mentioned that he wasn’t sure if he was meeting expectations. I was stunned. From my perspective, he was exceeding them. He’d become essential to our operations in a matter of weeks. But I’d never said that. Not once. I’d given him dozens of corrections and zero affirmations.
I changed that immediately, and I’ve been deliberate about it ever since. For every piece of corrective feedback, I try to give at least two acknowledgments of something done well. Not empty praise — specific recognition of specific work. “The email sequence you wrote for Client X had a 14% response rate. That’s exceptional. The third email in particular was perfectly pitched.”
People don’t need to be coddled. But they need to know they matter. Especially when they’re the first hire at a company where everything is uncertain.
How the Dynamic Changes
There’s a loneliness to being a solo founder that people romanticize. The lone wolf. The visionary. The person who needs nobody.
It’s nonsense. Being alone in a business is exhausting in a way that having a team is not. Not because of the workload — though that’s part of it — but because every decision, every doubt, every 2 AM anxiety attack happens in isolation. There’s no one to say “that’s a good idea” or “that’s a terrible idea” or “let’s figure it out together.”
When Alfredo joined, something shifted. Not just operationally. Emotionally. There was someone else in the building, figuratively speaking, who cared about the same things I cared about. Someone who could see a problem I’d missed. Someone who could carry a piece of the weight so I didn’t have to carry all of it.
The flip side is that you now carry their weight too. Their concerns, their career development, their bad days. When Alfredo had a rough week — personal stuff, nothing work-related — I felt it. Not as a manager managing a situation, but as a person who cared about another person’s wellbeing. That emotional investment is part of the deal, and it’s the part that nobody warns you about.
What I’d Do Differently
If I were hiring my first employee again, I’d do three things differently.
I’d write the expectations document before they started, not three months in. The clearer you are from day one about what good looks like, the faster someone can get there.
I’d build feedback into the daily rhythm from the start. Not weekly one-on-ones. Daily check-ins, even if they’re five minutes. The frequency matters more than the duration.
And I’d tell them, on their first day, something I wish someone had told me: “You’re going to see me make mistakes. Some of them will be obvious. I need you to tell me, not work around them. We’re building this together.”
Because that’s the truth of it. The first hire isn’t someone who works for you. They’re someone who builds with you. And the sooner you treat the relationship that way, the better everything gets.
Alfredo is still with us. He’s not the first hire anymore — he’s the general marketing manager, running operations I couldn’t have imagined when he started. But I still remember that sleepless night before his first day.
The weight of responsibility.
The exhilaration of not being alone.
Both real. Both permanent. Both worth it.