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Underrated Habits of Successful Startup Leaders

Underrated Habits of Successful Startup Leaders

Sasha Reid (Founder & CEO)

October 20, 2025

Everyone talks about the big things: vision, hustle, grit, innovation.
But if I’m being honest with you, what reliably distinguishes great startup leaders from the quiet curl-up-and-burnout ones is not often what gets the headlines in TechCrunch. It is usually the smaller, almost invisible habits, ones built in silence, accompanied by near-zero engagement, and they are the things nobody posts about on LinkedIn.

Let’s get into the ones that truly make a difference for successful startup leaders.

1. They stay calm when everything’s on fire

The true measure of a strong leader is not how well they carry themselves when things are going well, but rather when they are not going well. The best leaders in startups don’t flinch; they simply pause, breathe, and think clearly during the chaos of the day. Emotional regulation is an important soft skill to master; it is the difference between reacting and responding, and between an impulsive call versus the right call.

Example: Steve Jobs once said, “Details matter, it’s worth waiting to get it right.” 

That mindset – slowing down when pressure is high, isn’t just about perfection. It’s about not letting panic dictate your decisions.

2. They move on fast

Sounds odd, but it’s true. Successful founders have a short memory for both wins and losses. Celebrate the victory, learn from the loss, and move on. That’s how they keep moving. No dwelling on it, no ego, no shame spiral – just moving forward. The startup world doesn’t wait, and neither should you.

Example: Eric Ries (author of The Lean Startup) often talks about “validated learning”: build, test, measure, then pivot or iterate. Insofar as the failures become inputs, not anchors. (He has said many times that holding too tightly to mistakes blocks growth.) 

3. They choose real over polished

You can feel it when someone’s pretending to have it all figured out, it’s exhausting. Teams want truthfulness over perfect leadership. The most well-liked founders all openly share mistakes, request assistance and vocalise their uncertainty; it’s what creates loyalty versus compliance. Instead of spending forever polishing every small detail, some startup leaders really lean into authenticity and speed.

Example: In “Learning from My Failures: Lessons from a 2-time Founder” (TechCrunch), a founder described how in their first venture, they used a high-end creative agency, built stage-set-level photography, perfect product launch pages, etc. It impressed people. But slowed them. In their second company, they pared back design polish, used lean marketing, iterative feedback, and focused on what customers actually valued. This changed their trajectory.

Another is Tristan Walker (founder/CEO of Walker & Company): he spoke about authenticity, how, early on, he realised his startup couldn’t pretend to be something it wasn’t. He says being “the person best able to solve that problem you feel called to solve” is more sustainable than chasing what looks good from the outside.

4. They say “no” a lot

Leaders who turn down distractions, even exciting ones, give themselves room to chase what actually matters. They understand that every “yes” costs time, energy, and clarity.

Example: Brian Chesky, CEO of Airbnb, still practices what he calls founder mode. He remains intimately involved in decisions like hiring, promoting, and even firing up to dozens of employees, skipping organisational layers so he can say “no” to things that don’t align personally with his vision. This lets him safeguard the core values and avoid creeping distractions.

5. They seek out uncomfortable feedback

Most people run from criticism. Great founders hunt for it. They ask users what’s broken, tell teammates to be brutally honest, and listen to people outside their bubble. Painful? Definitely. But that’s where the real growth hides. And the irony? When leaders openly welcome feedback, teams feel safer to speak up, so everyone levels up together.

Example: Elon Musk said it clearly: “I think it’s very important to actively seek out and listen very carefully to negative feedback. This is something people tend to avoid because it’s painful.” Startup Archive

He adds: when friends try a product, he asks them, “Don’t tell me what you like. Tell me what you don’t like.” 

That habit of leaning into discomfort is what keeps leaders sharp rather than blind to flaws.

6. They repeat their vision until it sticks

Your vision needs to be alive, not something you state once in a team meeting. In a startup environment, the chaos can lead to distractions very quickly. The best leaders repeat the “why” and repeat the “why” again. That is how they ensure that every coder, designer, and marketer is moving in the same direction. Repeating the “why” is not repetitive and boring. It is the point of view of how the details and specificity come alive.

Example: Jack Zhang of Airwallex reflected in a recent interview that one of his early mistakes was not prioritising company culture THEN. Over time, he’s made culture statements, mission reminders, and vision summaries part of onboarding, team meetings, and hiring. That repeated reinforcement helped the team align through rapid international expansion. 

Also, Daniel Lubetzky (founder of Kind Snacks) talks about his morning routine: he altered it years ago to include affirmations or reminders of why he founded the company. Repetition of “why” in daily rituals anchors purpose. Entrepreneur

7. They build culture early, before it’s convenient

It’s easy to say “we’ll figure out culture later” when you’re three people in a coworking space. But that’s exactly when culture starts forming.

Example: Ben Horowitz (A16z cofounder) often talks about how culture isn’t just perks or mission statements. He says you must define early: “Who are we? Who do we want to be?” and bake real behaviours into day-to-day work. He shares how Amazon’s frugality was encoded via small things (like crude desks) early on, because their strategy needed to show that practice. That culture then scales. Startup Archive

Also, when Okta was still growing, its leaders made a decision: when a sales deal required promising features they didn’t have, they chose to lose the order rather than compromise customer trust. That decision, though painful, reinforced their culture of reliability over speed. Over time, that trust became a competitive edge versus rivals who shipped more features but had breaches or reliability issues. 

8. They guard their quiet time

Walks. Journaling. Thinking without a screen shining in your face. Undervalued? Absolutely. But this is where clarity takes place. Founders who make quiet thinking spaces apart from Slack pings and never-ending to-dos make better decisions. They see misalignments before they become issues. This is not a luxury, this is maintenance for the mind.

Example: From The Startup Chat with Steli & Hiten, there’s an episode “Why Founders Need to Schedule Quiet Time to Think Deeply.” They talk explicitly about how many founders say they don’t have time for it, but those who force it in (even 30 minutes a day) make better long-term decisions. 

Another example: Daniel Lubetzky described in interviews (Entrepreneur) how he used to try to clear inboxes till very late, had horrible sleep habits, and no clear boundaries. He then restructured so that mornings have “quiet blocks” with no meetings or emails. That helped reduce mistakes and stress.

Great advice on clear thinking from Sam Altman

9. They actually understand the numbers

You don’t need to become a bookkeeper or accountant. You just need to know cash flow, burn rate, and runway. This is how startups quietly die. Leaders who understand their numbers will sleep more easily. They’ll be able to make smart decisions without panic. Financial fluency doesn’t mean you have to love spreadsheets, it just means you respect their power.

Example: Mark Cuban recently advised startup CEOs not to get caught up in hype or mimic Silicon Valley norms, but to focus on building real, sustainable businesses. He emphasised talking to customers, doing sales, and understanding revenue & costs. It’s about knowing if the business model actually works, not just raising rounds.

10. They stay humble, even when they’re winning

Ego kills more startups than bad ideas. Staying humble keeps you grounded. It helps you avoid viewing everything through your own lens. The best leaders? They pay attention to advice that stings a bit, while maintaining curiosity. Humility does not make you small; it keeps you eminent in your own charism and coachable. That is why their teams are the ones that stick it through when things get dicey.

Example: The story of Dave Balter (founder, BzzAgent) is powerful. In his words, during the early success period, the hype got to him. When that ego kicked in, he misjudged competitors (one instance, he laughed off Facebook when it was tiny compared to his user count). Later, he reflected, learned to listen, take feedback, and respect others’ ideas even when under pressure. That humility changed how his team saw him, how investors saw them and saved the business in tough times.

To wrap things up

There is nothing glamorous about these habits. They are not featured in a founder interview or investor deck. But these habits will create the leader that people actually want to follow – the leader that not only survives in chaos, but knows how to thrive in that chaos! 

Startup success has nothing to do with the loudest pitch in the longest funding round. Startup success is about quiet consistency behind the scenes and daily habits that create something that lasts!

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