Why Founders Shouldn’t Be Too Positive: Lessons from The Hard Thing About Hard Things
When you're building something from nothing, optimism is fuel. It's what gets you started when no one else believes. But as your startup grows, optimism alone can become a liability — especially if you’re the one in charge.
Ben Horowitz, in his must-read book The Hard Thing About Hard Things, shares a surprising but vital lesson from his time as a startup CEO: his biggest growth moment was learning to stop being so positive.
At first, that sounds counterintuitive. Aren’t founders supposed to radiate belief, inspire confidence, and “fake it till they make it”?
Yes — and no.
Let’s unpack why realism beats relentless positivity, especially in the hard moments that define every startup’s story.
Positivity Can Undermine Trust
When leaders constantly project that “everything’s fine,” they may think they’re motivating the team. But often, the opposite happens.
Your team knows when things are hard.
They feel the tension in the numbers. They see product bugs, missed targets, or funding delays. If you, as the founder, keep smiling through obvious challenges without addressing them, people start to doubt you.
“If our CEO can’t see how bad this is… are we really in good hands?”
Ben Horowitz writes that honesty — even when brutal — was the turning point in his leadership. He realised that false positivity broke the most important currency a founder has: trust.
Hiding Problems Kills Startups
Startups don’t fail because of one big mistake.
They fail because of a hundred small ones — and no one said anything.
When a founder or CEO is “too positive,” they unintentionally create a culture where:
People are afraid to share bad news
Problems are buried or delayed
Teams focus on looking good, not being honest
The result? The CEO becomes the last person to find out what's really going wrong — and by the time they do, it’s too late to fix it.
Horowitz argues that great leaders must encourage bad news, not punish it. It’s how you stay close to reality and make decisions based on what is, not what you hope is true.
Realism Is Not Negativity
Here’s the key distinction:
Being honest ≠ being pessimistic.
Acknowledging hard truths ≠ giving up hope.
The best startup leaders maintain morale and motivation, but they ground it in reality, not fantasy.
“We missed our growth target. We’re tight on cash. But here’s what we do know, and here’s how we’ll respond.”
That kind of leadership builds confidence. It tells your team: We’re not hiding. We’re facing it head-on. Together.
Leadership Is About Facing the Hard Things
The title of Horowitz’s book is not accidental.
The hardest part of building a company is that there are no easy answers. Sometimes, there are no good options at all.
Your job isn’t to pretend things are fine. Your job is to:
Gather facts
Accept reality
Communicate with clarity
Make the best possible decision, even when it sucks
This is where leadership actually begins.
Final Thought: Trade Positivity for Clarity
At Entreprenerds, we often say: startups are built on clarity, not comfort.
That clarity starts at the top.
If you're a founder or early team member, remember:
You don’t need to pretend things are great
You do need to be honest about what’s hard
Trust is built in truth, not spin
The sooner your team knows the real terrain, the sooner you can work together to navigate it.
