A rocket needs its tail to lift off. Without it, the launch fails. But once altitude is reached, that same tail becomes drag. If it doesn’t detach, it limits how high the rocket can go.
Founders are the same.
Early on, my obsession and need for control were my biggest assets. I succeeded because , took the biggest risks, and made the tough calls myself. But as the company grows, these exact traits can drag me down. For me, the real skill now is knowing what to let go of and exactly when to do it.
Over the past two years, I’ve watched founders proudly announce that they’re cutting head count and replacing people with AI. Andreessen Horowitz has invested across nearly every layer of the AI stack, effectively putting eggs in every basket. OpenAI CEO Sam Altman has predicted the rise of “solo-unicorns,” billion-dollar companies built by one technical founder and a stack of models.
For many people in tech, building a unicorn with zero employees feels like the ultimate proof of genius.
I understand the appeal.
In my first startup, my cofounder and I believed we could do everything ourselves. Even though we had no background in sales, we were convinced we would outperform anyone we hired. We treated delegation as weakness and hiring as dilution. However, that mindset limited our ability to scale.
The ego trap in early-stage tech
In 2012, my cofounder and I started SailPlay, a SaaS platform for loyalty and marketing automation. We eventually sold it to Retail Rocket. Enterprise customers require integration, customization, and hands-on implementation. Beyond selling software, you’re selling trust and operational alignment.
Yes, we exited successfully. But looking back, I’m certain we could have built something 10 times larger if we had been more mature as leaders. If we had done the psychological work earlier, the company would have grown faster and further.
Intch, my current company, is already 40 times larger in annual revenue than my previous venture, despite having a smaller team now. The difference, in case you’re wondering, is not the product—it’s how I think about people.
When I was growing a different startup, LinguaLeo, my cofounder and I would go to the office at 2 in the morning to release updates. We would stay until everything stabilized, go home for a few hours of sleep, and return by 10 a.m. I told myself that 100,000 users would wake up and improve their English, and that was enough to justify the exhaustion. Yes, it felt meaningful. But it also kept me small, trapping me in the role of a hands-on operator instead of a leader building a scalable system.
I’ve seen the same pattern outside of tech. A relative of mine runs a furniture manufacturing business with multiple production facilities. When growth stalled, he brought me in as a consultant. I walked through one of the factories and saw him personally checking electrical wiring. His reasoning was simple. Half of factory fires are caused by wiring, and if he doesn’t inspect it himself, something could go wrong. Or that’s how he feels.
He wasn’t wrong about risk. He was wrong about leverage. Control can feel responsible. But in practice, it often blocks scale. While he was on his knees checking wires to prevent a hypothetical fire, the actual business was burning cash because no one was steering a long-term strategy, negotiating supplier contracts, or opening new distribution channels.
In the same spirit of doing everything myself, for years I built companies without HR. It was a costly mistake. Without dedicated people operations, talent acquisition was entirely reactive, and organizational drift went unnoticed until key people had burned out and left.
Ironically, I now run a company that serves HR leaders, and I recently hired a head of people for the first time. Her name is Kate. Since she joined, the leverage we get from our people has grown significantly. Hiring her formalized how we approach hiring, performance, and culture. It turned instinct into structure.
I finally made the move because we reached a point where my personal bandwidth could no longer match our organizational complexity. I realized that if I didn’t transition from managing people by gut feeling to building a solid talent infrastructure, we would plateau.
What hiring a head of people actually changed
When Kate joined, she rewrote half of our job descriptions. She explained why certain roles were written in a way that protected my ego instead of attracting strong candidates.
In areas where I didn’t feel personally competitive, the descriptions were reasonable. In areas where I saw myself as the strongest operator in the room, the descriptions were unrealistic. It was as if we were inviting someone who had just finished leading Microsoft to its IPO or led a wartime transformation effort to “come join us today.” Naturally, the requirements were set so high that absolutely no one applied.
As it turned out, by hiding behind these unrealistic expectations, I was unconsciously filtering for people who wouldn’t threaten me.
Kate asked a simple question: Why would someone who is smarter than you choose to work here?
I didn’t have a convincing answer.
Top talent doesn’t join companies for slogans. They join to work alongside other high performers. They want intellectual friction. They want standards. They want peers who challenge them.
The founder’s role is to create that environment.
Kate also pushed us to articulate our values as well as focus on building our culture. A few years ago, I would have laughed at the idea of a company retreat focused on culture. Now we’re preparing for our first off-site to define how we make decisions, how we resolve conflict, and what we expect from each other.
This shift is happening in a market where employers have significant leverage. We regularly see 4,000 to 5,000 applicants for a single opening. On paper, that sounds like strength. In reality, resentment accumulates quickly in environments where people feel disposable. Candidates accept offers and disappear. Engagement declines quietly.
This is why hiring a head of people during a wave of automation is a strategic move.
The discipline of delegation
As a company grows from 30 to 50 to 100 employees, the skills that helped the founder survive early chaos become constraints. Deep involvement in every decision feels productive. It limits the organization’s ceiling. The traits that helped you lift off cannot carry you into orbit.
Hiring a head of people forced me to confront this transition directly. Kate’s presence introduced structural accountability around hiring, performance, and culture. She professionalized areas I previously treated as instinct.
The result is a sharper organization.
Engineers spend more time on complex architecture. Commercial leaders focus on partnerships. Managers receive clearer feedback loops.
The narrative that AI will eliminate the need for strong teams assumes that building a company is primarily a technical problem. It isn’t. It’s a coordination problem, a trust problem, and, ultimately, a leadership problem. Founders who see AI as a shortcut to scale risk shrinking their own ambition. Scale requires systems. Systems require people who know how to operate them.
We hired a head of people while others were downsizing because we intend to build an enduring organization. AI expands our capabilities, but it doesn’t define our culture.
The question for founders is not whether to adopt AI. That decision is already made by the market. The question is what you choose to delegate to machines and what you choose to elevate in humans.
Get that balance right, and AI becomes a multiplier.
Get it wrong, and you end up alone with very efficient tools and very limited leverage.