Startup Leadership……..It was me, sitting in my apartment in Ohio, arguing with a co-founder over Slack about button colors while also trying to figure out payroll and whether we could afford actual health insurance.
Not exactly cinematic.
Nobody tells you this, but startup leadership isn’t about being inspiring 24/7. It’s mostly about staying calm when everything is mildly on fire. Or sometimes fully on fire. Like “why is our server down at 2am?” fire.
And I learned this the awkward way.
Back in 8th grade, I wore two different shoes to school. Not on purpose. It was a Monday. That’s basically how I approached leadership early on—confident on the outside, mismatched and confused underneath.
You ever feel like that?
The First Hard Truth: Leadership ≠ Control
I used to think being a founder meant being in control.
Ha.
Cute.
Startup leadership actually means giving up control strategically. You hire people smarter than you (hopefully). You let them make decisions. And then you sit there resisting the urge to micromanage like a caffeinated raccoon.
One of my early team members looked at me once and said,
“Do you want to lead this company, or do you want to approve every pixel?”
That hit. Hard.
If you want entrepreneurial leadership to actually work, you can’t be the bottleneck. You’re the thermostat, not the temperature.
Skill #1: Emotional Stability (Even When You’re Internally Screaming)
This one isn’t glamorous.
But it’s everything.
Your team watches how you react. If you panic, they panic. If you spiral, they spiral. It’s like emotional dominoes.
I once totally lost it over a failed launch. Not publicly. But internally? I was convinced we were doomed.
Then one of my engineers casually said,
“Eh. We’ll fix it tomorrow.”
And I realized something.
Founders don’t get the luxury of constant emotional swings. Startup management skills include emotional regulation. Which sounds clinical. But it’s really just:
Don’t make permanent decisions in temporary frustration.
Also—therapy helps. Just saying.
Skill #2: Decision-Making Without Perfect Information
If you’re waiting for certainty, you’re already late.
Startup leadership means making decisions with 60% data and 40% gut. It’s messy. It’s uncomfortable.
You’ll say, “I think this is the move,” and half your brain will whisper, “Or maybe we’re idiots?”
I used to over-research everything. Analysis paralysis. Google tabs open like I was prepping for the LSAT.
Now? I set a timer. Gather what I can. Decide. Adjust later.
Speed beats perfection most days.
Skill #3: Hiring People Better Than You (And Not Being Weird About It)
This one bruised my ego a bit.
The first time I hired someone who clearly knew more than me in their domain, I felt… insecure.
Which is ridiculous, right? That’s the goal.
But founder mindset takes work. You have to shift from “I need to be the smartest in the room” to “I need to build the smartest room.”
It’s like assembling the Avengers. You don’t compete with Thor. You just let Thor be Thor.
(And no, I’m not saying I’m Tony Stark. Though the sarcasm levels might match.)
Skill #4: Clear Communication (Even When It’s Awkward)
If you’re vague, your team fills in the blanks. And they usually fill them with anxiety.
Startup leadership requires clarity:
- Where are we going?
- What matters this quarter?
- What’s not a priority?
I once thought I’d been crystal clear about a product shift.
Turns out I hadn’t.
My developer thought we were rebuilding the entire platform. My marketing lead thought we were pivoting industries.
Cool cool cool.
Now I over-communicate. Probably annoyingly. But confusion is more expensive than repetition.
Skill #5: Conflict Management Without Acting Like You’re in a Reality Show
Conflict will happen.
Co-founders disagree. Employees clash. Slack threads get spicy.
Your job isn’t to eliminate conflict. It’s to prevent it from becoming toxic.
I once avoided addressing tension between two team members because I “didn’t want to make it worse.”
Guess what happened?
It got worse.
Startup leadership sometimes means stepping into uncomfortable conversations and saying:
“Okay, what’s actually going on here?”
No drama. No sides. Just clarity.
Skill #6: Vision Casting Without Sounding Like a Motivational Poster
There’s a fine line between inspiring and cringe.
You don’t need to be on stage like you’re giving a talk at TED. But your team needs to know why this matters.
Why are we building this?
Why does it exist?
If the only answer is “because it might make money,” that’s… thin.
When I started talking more openly about the problem we were solving—who it helped, why it frustrated me personally—something shifted.
People leaned in.
Startup leadership isn’t hype. It’s conviction.
Skill #7: Financial Literacy (Even If You Hate Spreadsheets)
Listen. I don’t love spreadsheets.
They don’t spark joy.
But ignoring your numbers is like driving with your eyes closed and hoping vibes will steer the car.
You need to understand:
- Burn rate
- Runway
- Gross margin
- Customer acquisition cost
Even if you have a CFO someday, you still need fluency.
Otherwise someone can tell you, “We’re fine,” and you won’t know if that’s true or just optimistic delusion.
Skill #8: Adaptability (AKA Ego Flexibility)
The market doesn’t care about your original idea.
I’ve pivoted. Adjusted pricing. Killed features I loved.
It hurts. Like deleting a playlist you curated for months.
But startup leadership means falling in love with the mission, not the method.
Blockbuster didn’t adapt.
Netflix did.
That’s not subtle.
Skill #9: Resilience Without Martyrdom
There’s this weird glorification of burnout in startup culture.
Sleep four hours. Hustle harder. Grind grind grind.
I tried that.
I turned into a cranky, foggy-brained version of myself who thought ordering Uber Eats at midnight was a personality trait.
Resilience isn’t about self-destruction. It’s about sustainable grit.
Take breaks. Exercise. See your friends. Touch grass. (Literally.)
If you collapse, the company feels it.
A Quick Tangent About Leadership and Identity
Here’s something nobody told me.
When you’re the founder, your company becomes tangled up in your identity. If it struggles, you feel like you are struggling.
That’s dangerous.
I once read a brutally honest founder post on Paul Graham’s essays (highly recommend browsing those late at night if you enjoy existential spirals). It reminded me that companies are experiments. Not personal worth meters.
That reframing helped.
A lot.
Startup Leadership Is Mostly Learning on the Fly
I wish there were a clean checklist.
There isn’t.
Leadership skills for founders develop under pressure. Through mistakes. Through awkward meetings and bad hires and late-night doubts.
You’ll mess up.
I still do.
Last year I sent a company-wide message that had a typo in the first sentence. Not catastrophic. But symbolic.
We’re human.
Startup leadership isn’t about being flawless. It’s about being responsive. Self-aware. Willing to adjust.
If I Could Whisper Advice to New-Founder Me
It would be this:
You don’t need to become a different person to lead well. You need to become a more intentional version of yourself.
Develop:
- Emotional control
- Clear communication
- Financial literacy
- Adaptability
- Vision
- Conflict resolution
- Decision-making speed
But also keep your humor. Your quirks. Your humanity.
The best founders I’ve met aren’t perfect. They’re grounded.
They admit when they don’t know something.
They stay steady when things wobble.
And things will wobble.
A lot.
