Tactical insights for first-time founders to outsmart the burn, the churn & the breakdown.
Hey Founder,
We’ve all seen the exit fantasy: build fast, sell big, and coast into freedom, champagne in hand and inbox full of “you made it” messages.
But behind the headlines, most founders tell a different story...
The truth? Exiting is often more disorienting than the chaos of scaling. The payout feels smaller than promised. The identity you built your life around disappears overnight. And no one really prepares you for that part.
Even big names like Dorsey and Ohanian have spoken about exit regret, and they had resources most don’t.
So in this issue, I want to explore what actually happens after you sell, and how to make sure the freedom you’re chasing doesn’t turn into a very expensive identity crisis.
The Margin
When Equity Doesn’t Become Wealth
Let’s get one thing straight: exits aren’t the enemy. But they do punish founders who aren’t prepared.
We all know the Reddit story: Ohanian and Huffman sold early for ~$10M, then watched the company soar to a multi-billion valuation. At the time, the decision made sense - no playbook, no financial context, just the safety of cash in the bank. But years later, the regret is real.
(Fortune)
Ankur Warikoo faced a different version: Nearbuy was a $65M company. On paper, he was wealthy. In reality, he left with five months of runway and credit cards maxed out. The exit didn’t rescue him, and the pandemic nearly wiped him out. His advice? Don’t wait for the term sheet to get financially literate.
Then there are stories like Pebble’s founder walking away with $0 from a $23M sale. Or insiders at Blue Apron were watching the stock plummet 95% before they could sell. Or James Altucher losing almost everything after selling for $10M.
The point is: exit doesn’t equal wealth.
Not unless you're ready, with clean books, tax planning, equity clarity, and a plan for what comes next.
Most founders prepare their company for exit.
Very few prepare themselves.
Let’s talk about how to change that.
Why “Exit Disasters” Happen
Most founders walk away from an 8‑figure exit still stressed about cash, not because they sold too cheap, but because they never saw where the money actually goes.
The structural leaks start early:
Investor preferences (30–50%) – Preferred shares get paid out first.
Dilution (25–40%) – By Series B or C, your slice is much smaller than you remember.
Taxes (35–50%) – Between federal and state, it adds up fast.
Fees (2–5%) – Bankers, lawyers, advisors… everyone gets a cut.
Locked stock (~50%) – Most of your “payout” isn’t liquid right away.
(Dilution after multiple rounds)
That shiny $20M headline? It might be $3–6M at best, and that’s before the stock drops or the earn-out underdelivers.
Then come the cracks inside the business: messy books, unclear contracts, last-minute ESOPs, all red flags to buyers. They’ll either discount the deal or walk.
And the traps inside the founder’s head:
Assuming the payout will be bigger than it is
Avoiding tough conversations around tax and liquidity
Post-exit identity crisis (it's real, ask anyone who’s sold)
The founder of Loom shared that after selling to Atlassian, he felt lost, no purpose, no direction. James Altucher sold for $10M and still lost nearly all of it chasing “freedom” with no real plan.
Tiny Reframe
You can’t control the market, but you can control how exposed you are.
Prepare now, with clean systems, smart paperwork, and a financial buffer for you, not just your cap table.
Because the riskiest thing you can do is wait until after the exit to figure it all out.
6 Margin Moves for Becoming Exit-Ready
Whether you’re years away or already taking meetings, these are the moves that protect your outcome (and your sanity).
Pre-Exit Moves
1. Pay Yourself Like a Grown-Up
Once the business can afford it, aim for 50–70% of your market salary.
Build a personal runway (6–12 months) and keep finances clean, no mixing personal with business.
2. Know Your Actual Take-Home
Run an exit waterfall: ownership, investor prefs, fees, taxes. What matters isn’t the headline; it’s what hits your account.
Update it regularly so you’re not guessing when it counts.
3. Make Your Equity Work Harder
File your 83(b) early (or regret it later).
Look into QSBS if you qualify - structured right, it can save millions in taxes.
Keep your cap table and 409A tight - early equity only matters if it holds value.
4. Clean Your House
Tidy books, monthly closes, contracts organized, data room live. Even if you’re not planning to sell soon, this is your leverage when you do.
After the Exit
1. Hit Pause
No new ventures in week two, no houses, no angel sprees.
Give yourself 6–12 months to reset and build your circle: therapist or coach, CPA, planner, other founders who’ve been through it.
2. Don’t Let One Check Define Your Future
Start selling concentrated positions when possible.
Keep 60–90% of net worth in boring, diversified assets. Use rules: no single investment >5%, and a 72-hour pause on major money moves.
Tough Love Corner
A founder shared this week:
“I’m burned out and low-key resenting my customers. I know it’s a red flag, but I don’t see a way to slow down without hurting the business. How do I pull back without breaking everything?”
Burnout isn’t a weakness. It’s a warning light that you’ve been operating without boundaries for too long.
Here’s how to pull back before you snap:
1. Delegate the roles that drain you most
Make a quick list of everything you do - CEO, sales lead, ops, therapist. Start with the ones you dread. Hire or offload those first.
2. Re-train your customers
If they expect 3-minute replies and weekend support, that’s a system you taught them. Reset expectations: response times, communication channels, office hours. Put it in writing.
3. Push decisions down
If every call runs through you, you’ll burn out by default. Create a simple “who owns what” doc, real accountability, not performative job titles.
4. Redesign your role
This isn’t just about managing your calendar. It’s about shifting toward work that energizes you and stepping out of what drains you, on purpose.
Will it be messy? Probably.
But it’s less messy than hitting a wall and resenting the thing you built.
Got a burning founder question?
Send it my way, just hit reply.
Founder’s Toolbox
A few small but mighty finds for the long game:
Before you go…
A great exit isn’t just about the check size, it’s about what life feels like after.
Control. Clarity. Breathing room.
If you’re sitting between “I made it” and “Now what?” you’re not broken. You’re just entering your next chapter.
Vinay Hiremath (Loom) is rebuilding from scratch. Sam Altman sold Loopt, wandered a little, and eventually built OpenAI.
Because purpose, not a payout, is the real 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.
