We lost €70,000 on a sales hire. That was my most expensive lesson in bootstrapping.
When you're running a young company, everyone starts offering the same advice: "You need to hire a Head of Sales." Investors say it. Advisors say it. Other founders say it. And when everyone's telling you the same thing, it starts to feel like truth.
So we listened. We found exactly what people told us we needed: a Head of Sales with an impressive resume, years of experience at well-known companies, big strategic plans, and even bigger salary expectations. On paper, this person looked perfect.
What We Got
Lots of meetings. Lots of slides. Lots of grand ideas.
Our new Head of Sales came in with energy and ambition. Strategy sessions about market positioning. Decks about sales funnels and conversion optimization. Proposals for new partnerships. Detailed plans for building out a sales team. Everything looked professional. Everything sounded smart.
But here's what we didn't get: actual sales. Real customer conversations. Closed deals. Revenue growth.
The gap between strategy and execution turned out to be enormous. While we were busy discussing frameworks, we should have been talking to our customers. While we were negotiating partnerships, we were losing momentum in the market.
What We Lost
The reality was that we lost months of growth during a phase where every euro and every hour counts. We weren't just paying a salary. We were paying an opportunity cost. Those months could have been spent iterating on our product, talking to customers ourselves, or investing in channels that actually worked.
And here's the part that really stung: we didn't even have enough revenue to fund the hire. Bernhard and I paid for it out of our own pockets. We believed in the advice so much that we were willing to personally bankroll what turned out to be an expensive mistake.
In the end, I might as well have thrown the money out the window. The result would have been the same.
The €70,000 wasn't just salary. It was salary plus wasted time plus deals we didn't close plus the motivation we lost as a team when we realized this wasn't working.
The Real Lesson
Today, I know that blindly following external advice won't get you anywhere. What you really need, you only learn through your own mistakes.
Stage matters more than credentials. What works for a Series B company with product-market fit doesn't work for an early-stage bootstrapped business still figuring things out. We needed someone who could roll up their sleeves and make calls, not someone who wanted to build an empire.
Bootstrapping requires a different mindset. The best hires for bootstrapped companies aren't necessarily the people with the fanciest resumes. They're the people who thrive in ambiguity, who can do the unglamorous work, who understand that strategy without execution is just expensive daydreaming.
External pressure leads to bad decisions. When everyone's telling you what you "should" do, it's easy to doubt your instincts. But outsiders don't know your business, your customers, or your constraints the way you do. Their advice might be right for them. That doesn't make it right for you.
The pressure to scale quickly can push you into decisions that feel professional but aren't practical. A fancy title and a polished strategy deck mean nothing if they don't move the needle. In bootstrapping, execution beats strategy every single time.
Moving Forward
After this experience, we completely changed our approach to hiring. We started looking for people who fit our stage, not people who looked impressive in an org chart. We valued scrappiness over credentials. We hired people who wanted to build, not people who wanted to manage.
But more importantly, we raised the bar for when we hire at all. Now we only hire when the pain is absolutely unbearable. When we've exhausted every other option. When staying small is no longer possible without breaking something critical.
The goal isn't to build a big team. It's to stay as small as possible for as long as possible. Every new person adds complexity, communication overhead, and coordination costs. Sometimes that's worth it. Most of the time, it's not.
And we stopped listening to every piece of advice that came our way. Some lessons, it turns out, you have to pay for yourself.
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Want the full story? I shared more details about this experience on the Happy-Bootstrapping Podcast with Andreas Lehr. Fair warning: it's in German only, but if you speak the language, check it out for the unfiltered version of what went wrong and what we learned.
