Tactical insights for first-time founders to outsmart the burn, the churn & the breakdown.
Hey Founder,
You know what kills trust faster than a bad quarter?
Saying “I’m open and transparent” and then losing it the moment someone actually tells you the truth.
I watched a founder melt down in front of 80+ people. The team had been working nights, skipping weekends. Someone finally asked a fair question about roadmap risk, and the founder snapped. Red-faced. Slammed the table. Stormed out.
In that moment, the message was clear: honesty wasn’t welcome. And the team learned to shut up and nod.
That’s what being uncoachable looks like.
It’s also how you quietly kill momentum from the inside out.
Let’s unpack this.
The Margin
The Founder Trait Investors Bet On
If you’ve watched F1, you’ve seen the split.
Sonny Hayes, nearly 60, leads with composure. He takes ruthless yet strategic risks with emotional intelligence, not ego. He races with his team, even positioning his protégé, Joshua Pearce, to win.
Pearce? He’s young, insecure, addicted to clout. Mistakes help for competition. Sonny says it best: “He can’t analyze risks.”
Sound familiar? Founders rarely fail because the idea is bad, they fail because the ego blocks the pivot.
Coachability is the margin.
It’s the difference between walking out of a meeting with trust and a term sheet... or bristling at feedback and watching the deal die in real-time.
Patrick Collison (Stripe) once heard in a board meeting: “You’re the blocker.”
He didn’t flinch, he changed. Stripe doubled hiring and retention that year.
Airbnb? In 2009, they were flailing. Paul Graham told them to do something most founders would scoff at: “Go meet customers door-to-door.”
They did.
Their competitor, FlipKey? Never heard of them again.
Tiny Reframe
Instead of bracing against feedback, try asking:
“What might I learn if I got curious instead?”
Feedback hurts. That’s normal. But the real trap? Making it about your ego instead of the insight. Curiosity is key, it moves you from self-protection to real growth.
Ask yourself: “What can I take from this, even if it’s clumsy or off?”
Coachability isn’t about blind agreement. It’s about stress-testing the advice, running the experiment, measuring the results, and staying open to what you didn’t know.
You’re not supposed to have all the answers. And the best founders don’t aim to be right, they aim to find what’s true.
That’s the real game: digging through discomfort to uncover the one golden insight that shifts everything.
Why You Should Care
Startups are chaotic. No matter how sharp you are, you’ll be wrong a lot. The real risk? If you’re not coachable, you get stuck on your first (usually wrong) idea.
Founders who resist feedback often end up:
Building the wrong product by clinging to assumptions
Losing great people to “my way or the highway” culture
Stalling growth as blind spots become roadblocks
And if you're wondering: “Is coachability something you’re born with?”
Good news, it’s not.
Coachability isn’t a fixed trait. It’s a skill, a set of learnable behaviors that can be trained, practiced, and improved over time.
Here’s what coachable founders consistently do differently.
Margin Moves You Can Run This Week
1. Learn from a Real Startup Failure
Choose a well-documented startup that didn’t make it (YC’s archives are a great start).
Ask yourself: Would I have listened to the advice they ignored? If not, what blind spot do you share?
Example: Kiko was a web calendar app competing with Google. Would you have pivoted the moment Google launched?
2. Run a 24-Hour Reality Check
Pick one product assumption and validate it, fast.
Think your onboarding’s smooth? Send it to 5 new users. Ask them to screen-record their first 3 minutes. Watch for where they get stuck.
3. Spot the Missed Signals
Keep a log of your surprises this week. Add a simple score:
1 = total shock, 5 = I sensed it but ignored it.
Review on Friday: any patterns? What signs did you overlook?
4. Do a “Red Team” Review
Pick one decision you feel strongly about.
Assign someone to challenge it from every angle.
Back it up with data.
(Remember: “Don’t manage by opinion. Manage by evidence.”)
5. Switch Sides on a Tough Call
Pick a decision you’re debating with your team.
Swap roles: you argue for their view, they argue for yours.
This stretches your thinking and often reveals better answers.
Tough Love Corner
A founder DM’ed me:
“We added a $9 starter plan to boost signups. It worked, user count doubled. But…
- They churn fast
- Need more support
- Some $49 users downgraded
Now MRR is flat. Do we kill it or wait and see?”
Cheap plans look like growth. But they often mask churn, bloat support, and damage brand positioning.
Start with the hard numbers:
MRR: Are you making more, or just diluting value?
Support load: Are $9 users costing more per $ earned?
Upgrade funnel: What % move up within 90 days? Is that data or just hope?
If the math says no, here are your options:
1. Segment & Convert
Keep the $9 plan, but tighten it. Limit features, cap usage, nudge upgrades relentlessly. Price by value, not vanity.
2. Rebrand It
Position it for hobbyists, students, nonprofits. Let the low-LTV users self-select without cannibalizing your core.
3. Kill It (Gracefully)
Sunset it with a long grace period and an upgrade incentive. Refocus on the $49+ users who power real growth.
Track these before making the call:
Upgrade rate ($9 → $49)
Churn ($9 vs $49)
Support cost per user
LTV:CAC by plan
Downgrade rate ($49 → $9)
Bottom line:
Volume without value is a sugar high. Real growth comes from founders who are brave enough to cut the noise.
Got a burning founder question?
Send it my way, just hit reply.
Founder’s Toolbox
Want to know how coachable you really are?
These two personality frameworks offer a quick lens into how you handle feedback, uncertainty, and leadership pressure:
The following tests will give you sufficient reflection about your personality and leadership:
How to use them:
Don’t overthink the scores. Look for your edges.
Too agreeable? You might avoid conflict.
Too dominant? You might resist input that challenges you.
Before You Go...
Being coachable doesn’t mean agreeing with everyone.
In fact, being too open to advice can dilute your clarity.
Startups need direction, not consensus. And not all advice is equal, especially from people who haven’t built what you’re building.
So use coachability to refine your instinct, not replace it.
That’s your edge.
That’s your 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.
