Tactical insights for first-time founders to outsmart the burn, the churn & the breakdown.
Hey Founder,
The most difficult part of your journey often isn’t the early hustle, the late nights, or even getting your first customer.
It’s realising that what got you here, being hands-on, doing it all, moving fast, isn’t what will get you to the next stage.
It’s that quiet leap from founder to CEO.
Stepping into that role demands a different kind of thinking. Yet most founders aren’t taught how to make that shift without second-guessing themselves or losing momentum.
In this issue, I’ll break down what truly changes when you move from founder to CEO, and how to navigate that transition with clarity, confidence, and control.
The Margin
Outgrowing the Founder You Were
Luis von Ahn built reCAPTCHA. Then Duolingo. A classic hacker-founder, deeply hands-on until he couldn’t be.
“Most of my job now,” he says, “is culture carrier, mascot… and making tough philosophical decisions.”
He micromanaged until employee 50. “I should’ve stopped at 30.”
Zuckerberg made the shift too, from hoodie to Mandarin-speaking diplomat, expanding Facebook into new markets.
Travis Kalanick didn’t. He built Uber by brawling, and lost it the same way.
I’ve seen the in-between up close. A founder scaled to $10M ARR, then slowly slid back to $1M. Not because the product broke. But because leadership never evolved.
Scaling doesn’t ask for more effort.
It asks for a different version of you.
(Wonder why this isn’t Mark’s official business card anymore 🤔💭)
Tiny Reframe
Founders build products. CEOs build companies.
Ignore the shift, and the role will outgrow you.
At its core, the transition is about mindset:
From Builder, doing whatever it takes to find traction
To Scaler, hiring the right people, building systems, and making decisions around finance, structure, and long-term strategy
It’s not about doing more. It’s about thinking differently.
(99% never make this shift)
The Traps That Keep Founders Stuck
Control addiction: Letting go feels unnatural, like you're stepping back. But often, it's not responsibility. It's the fear of becoming irrelevant.
Comparing yourself to “real” CEOs: You look at polished execs and wonder if you even belong. Spoiler: you do.
Impostor syndrome: You start believing the success was luck. That someone, your team, your board, will figure you out.
Limiting beliefs:
"I'm just technical."
"I'm bad at people."
"I'm not a visionary." False.
They're stories, not facts.
What These Stories Miss
Every CEO you admire once stood where you are. “The founder-to-CEO transition kicked my ass,” said Scot Chisholm. Jonathan Lowenhar puts it simply: Founder is identity. CEO is craft. And craft is learned.
Leadership isn’t about having all the answers. It’s about growing into better ones.
So… What Does a CEO Actually Do?
A practical frame, adapted from executive coach Jonathan Lowenhar:
Set direction: Define why the company exists, where it’s going, and how progress is measured.
Build the team: Hire well, fire when needed, empower constantly.
Create structure: Operating rhythms beat chaos.
Own the story: Repeat the narrative until it echoes without you.
Make the hard calls: Culture is what you tolerate. Guard it.
The Margin CEO Upgrade: 5 Moves to Run This Week
1. Audit Your Calendar
Pull up your past 7 days. Highlight anything tactical (approvals, execution, firefighting).
Now replace one of those with a real CEO move, strategy time, a leadership 1:1, an investor conversation. Your calendar reflects your altitude.
2. Run the PDP Check (Purpose, Direction, Progress)
Ask 5 random team members:
Why are we here?
Where are we going?
How are we doing?
If you get 5 different answers, congrats, you’ve just found your #1 job for the next month.
3. Fire Yourself (In Public)
Pick one task you’re still clinging to: approving copy, running demos, reviewing sprint tickets.
Announce it at the next team meeting. Hand it off, name the new owner. Coach quietly. Don’t step back in.
4. Write the Culture Memo
Jot down 3 behaviors you’ll always reward, and 3 you won’t tolerate. Share it. Don’t wait for a crisis to define your culture.
5. Activate Your Talent Radar
List the 3 hires that matter most for your next chapter. Book one coffee with a candidate this week, no agenda, just a connection. That pipeline starts now.
Tough Love Corner
“Everyone’s busy, but we’re not aligned.”
A founder emailed me last week with this:
“Despite my best efforts, I can’t get my team moving in the same direction. Is there one habit or meeting that actually works?”
Short answer?
No meeting alone will fix misalignment. You need a clear, shared goal first, monthly or quarterly. Only then can a ritual create real traction.
If I had to choose one, it’s this: Weekly Rose-Bud-Thorn Check-In (30 mins).
Rose: A win or progress
Bud: A priority or opportunity
Thorn: A blocker
No slides. No deep dives. Just visibility, momentum, and early detection of drift.
Run it weekly, and alignment stops being something you chase and starts being something you build.
Got a burning founder question?
Send it my way, just hit reply.
Founder’s Toolbox
A practical guide for navigating the messy transition from founder to CEO, covering core roles, common pitfalls, and what to expect.
Focused on Deep Tech, Vertical AI, and Biotech. $500K–$2M checks, pre-seed and seed stage. Fast decisions, direct pitch link here.
At the end of the day, becoming a CEO isn’t about changing who you are. It’s about growing into who your company needs next.
Before you go…
You don’t “graduate” into leadership. You practice it, one behavior, one shift, one week at a time.
Tiny upgrades. That’s the moat.
See you next Thursday,
— Mariya
What did you think of today’s issue?
Hit reply and let me know. I read every single one (for real).
About me
Hey, I’m Mariya, a startup CFO and founder of FounderFirst. After 10 years working alongside founders at early and growth-stage startups, I know how tough it is to make the right calls when resources are tight and the stakes are high. I started this newsletter to share the practical playbook I wish every founder had from day one, packed with lessons I’ve learned (and mistakes I’ve made) helping teams scale.
