#85: Paranoia Wins & The SendGrid Flip
June 8, 2025 – DevTools Brew #85
I’m Morgan Perry, co-founder of Qovery. Every week, I share the real, often uncomfortable lessons from building and scaling devtool startups—from 0 to 1 and beyond.
In today's edition:
Paranoia Wins
→ The calm is the trap. Why, as a founder, I now treat comfort as the biggest red flag, in hiring, deals or, execution.
The SendGrid Flip
→ How SendGrid (CEO) reversed its slowdown and scaled to a $2B exit.
Let’s get into it.
Paranoia Wins
The calm is the trap
“it’s never the ‘no’ that kills you. It’s the slow drift before it.”
There’s a line I used to think was exaggerated:
“Only the paranoid survive.”
Now I think it’s one of the truest things I’ve learned.
We just lost a key candidate. Senior profile, solid track record, cloud-native… could’ve been a game-changer. Everything seemed smooth: mutual interest, great fit, strong signals.
Until he slipped away…hours before signing.
Why? Because we didn’t press enough.
We didn’t challenge the calm.
Too many silent gaps. Not enough tension. Not enough truth, early.
Same happens in Sales.
A deal feels good. You’re aligned. They love the demo.
So you slow down. You assume intent. You stop pushing.
Then one day… ghosted, delayed, deprioritized, gone.
Fundraising’s no different.
You don’t lose when a VC says no.
You lose when you let your process drift.
When you stop asking the question that burns:
“What could break this tomorrow?”
The trap is comfort. The cost is momentum.
If I had to do that candidate process over again, I’d do it differently:
→ Surface tensions earlier
→ Create urgency, not comfort
→ Anchor the relationship with clarity, not assumptions
And this goes way beyond hiring.
Every week, I see how paranoia is not a weakness but a discipline.
Not about obsessing over competition.
But about protecting your edge.
Sharpening what makes you better.
Keeping the engine warm even when things look calm.
Because startups don’t lose to others.
They lose to drift.
To silence.
To thinking “it’s fine” when it’s already slipping.
In every deal, every hire, every feature decision — there’s a choice:
Be paranoid. Or pay the price.
Because when you start relaxing, reality starts rewriting the outcome without you.
The SendGrid Flip
From plateau to $2B exit: How SendGrid reversed the curve without breaking the culture.
When Sameer Dholakia (CEO) joined SendGrid in 2014, the company was at a crossroads. Growth had slowed from 100%+ to ~30%, and no one was sure whether the curve would keep dropping. He wasn’t a founder and in the Valley, that’s rarely an advantage.
But he had one thing on his side: brutal clarity.
“You don’t make a CEO change if everything’s going perfectly.”
His diagnosis was quick:
→ A loved product with strong self-serve motion (devs dropping in APIs + paying with credit card)
→ A company unsure of what it wanted to be: email-first, or a general devtools platform?
→ A culture that cared, but had outgrown its early leadership.
Here’s what changed the trajectory:
Mission alignment first.
The team needed a clear strategic bet: stay focused on email as a category-defining company. Instead of chasing other APIs, they doubled down and expanded horizontally into adjacent use cases (marketing email → multichannel comms). That gave them clarity and a bigger TAM.
New chapter = new leadership.
Over 24 months, 7 out of 8 execs changed. But Sameer didn’t rush.
“One exec hire per quarter. Because getting it wrong costs years.”
He prioritized culture fit + seen-it-at-scale experience. Every departure was handled with honesty and dignity.
Ops as a compounding advantage.
They built a plan called “Pipeline 2020” to redesign infra before it became a bottleneck. While the infra seemed to work, they projected the math: if growth returns, we’ll break. They future-proofed it before the curve turned up.
Turning product parity into pride.
A competitor was publicly comparing feature checklists. Instead of ignoring it, they built a tiger team:
“One missing feature removed every month. One check at a time.”
Six months later, the checklist disappeared. Nine months later, the competitor did.
Cultural foundation: before the IPO or acquisition.
Sameer kept hammering the “4 Hs”: Happy, Hungry, Humble, Honest.
That made change manageable and paved the way for a smooth IPO and, later, a $2B+ acquisition by Twilio.“Being public instills a rigor that makes you better. It forces you to be buttoned-up.”
What I love in this story is how operational clarity beat the mythical narrative of the genius founder-CEO. Sameer didn’t invent SendGrid. But he scaled it with discipline, not ego.
It’s not always about building something new. Sometimes, it’s about turning around something great before it gets forgotten.
Final Thoughts
Both stories are about what you do before things break.
→ When a key candidate slips away: not because of a ‘no’, but because you stopped pressing.
→ When a good company plateaus: not from failure, but from drifting without clarity.
In both cases, recovery starts with one shift: stop assuming things are fine.
→ At the early stage, that means asking the uncomfortable questions before it’s too late.
→ At scale, that means building the systems to stay sharp even when growth returns.
Whether you’re hiring your next exec or steering a $100M org, paranoia isn’t fear.
It’s maintenance.
It’s pressure-testing what looks smooth.
It’s refusing to drift.
Comfort never scales.
But clarity does.
That’s it for me today! :)
Thanks for reading and Happy Sunday!
— Morgan
Do you like personal lessons like this? More insights/stories from other devtool founders? Let me know, I’m always open to feedback.
You can reach out to me on LinkedIn.