Tactical insights for first-time founders to outsmart the burn, the churn & the breakdown.
Hey Founder,
Today’s topic isn’t glamorous, but it’s exactly what sinks promising deals.
Just last week, I met a founder in Brooklyn. Great pitch. Clear traction. I was genuinely intrigued.
Then I asked, “Can I see your data room?”
Silence.
What followed said more than any pitch ever could. Disorganization, missing numbers, outdated files, it was a masterclass in what not to do.
In this third issue, we’re shining a light on something that rarely makes headlines but regularly kills momentum: the data room.
The Margin
The Silent Deal Killer (& Winner)
Over coffee, the founder, clearly frustrated, shared a painful near-miss.
He’d bootstrapped to $1M ARR and finally got a shot with a top-tier VC. The pitch went well. The room was excited.
Then came due diligence.
His “data room” turned out to be a Google Drive mess:
Files named P&L_Final_v4_EDITED.pdf…
Decks labeled USE_THIS.pptx…
Unexplained SAFE notes… missing employment schedules… financials scattered everywhere.
What followed wasn’t diligence, it was a scavenger hunt.
Investors lost confidence, and a competitor with the same numbers but clean, ready docs? Closed in ten days.
The difference? Operational readiness.
It’s not flashy, but it closes deals.
And the worst part? It’s entirely preventable.
Start early. Set it up right. First principles win.
Why You Should Care
Raising Capital?
Due diligence is the pitch. Investors will comb through everything: corp docs, financials, product roadmap.
Your CAC, LTV, churn, burn... they’re not skimming, they’re scrutinizing.
If your deck says $500K ARR but your books say $300K?
You’re not “early”, you’re “not serious.”
Thinking M&A?
70–90% of M&A deals fall apart. Why? Poor prep and murky data. If your answers are slow or sloppy, buyers walk.
Working with Big Clients or Banks?
Enterprise clients, lenders, B Corp certifiers, they all need a clean audit trail.
Org charts. IP assignments. NDAs. Security docs.
I’ve seen deals stall for weeks over a missing SOC 2 folder.
Scaling Beyond Hustle Mode
Once you hit $500K ARR, hustle isn’t enough, execution is everything. Outdated statements? Red flag.
Whether bootstrapped or VC-backed, clean ops signal you’re built to last.
Bonus: Your Own Sanity
One central source of truth > digging through email threads and scattered PDFs.
Even if no one’s looking yet… you should be.
Tiny Reframe
A data room isn’t about legalese or bureaucracy.
Instead of a chore, view it as the behind-the-scenes proof of your promise.
Even minor inconsistencies can make investors raise eyebrows. It’s about showing you’re in control.
Hustle Fund puts it best: "Impressive companies are organized."
5 Margin Moves to Run This Week
1. Organize Your Data Room
Create a clean, easy-to-navigate folder (Google Drive, Notion, or DocSend).
Use clear labels: Finance, Legal, Tech, Sales
Add a simple table of contents
Rule of thumb: No doc should take more than 2 clicks to find
2. Upload Core Docs
Get the essentials in place:
12+ months of financials
Tax returns, incorporation docs, cap table
Key contracts, IP assets, major customer agreements
Here’s the ultimate cheat sheet to keep your data room organized and investor-ready:
3. Check the Numbers
Audit your deck and financial files:
Make sure every metric matches the source
Label projections clearly
Discrepancies (like $500K ARR in deck vs. $450K in Excel) erode trust fast
4. Upgrade Security
If you're gaining traction:
Move from Google Drive to a VDR (Ansarada, Digify)
Set permissions + access logs
5. Assign a Gatekeeper
Choose someone to own the VDR (you or a fractional CFO):
Update it regularly
Run mock investor Q&As to stay pitch-ready
Source: Mario Peshev
Tough Love Corner
Someone asked me last week:
“If you had full access to my business for 30 days, what would you fix first?”
Easy:
I’d start with internal hygiene: clean data, clean docs, clean dashboard. Your data room should be investor-ready now.
If I can’t understand your last 12 months in 30 minutes, you’re not ready.
Next: cash flow. Plug leaks, cut waste, and make every dollar earn its keep.
Then ops: automate what’s clunky or manual.
Finally, metrics: no fluff, just KPIs that drive real decisions. If your dashboard can’t tell me what’s working or broken in 60 seconds, it’s not doing its job.
Litmus test: If you vanished for a week, would the team know what to do and why?
That’s the bar.
Got a burning founder question?
Send it my way, just hit reply.
Founder’s Toolbox
Investor-Ready Data Room Template
Need a founder-friendly way to get your data room in shape?
This Google Drive template includes a clean folder structure, clear headers, and a checklist I’ve used with startup teams. Now it’s yours.
Click here to access it.
Bonus:
Thomas Budnik’s legal write-up on data rooms (use it as a roadmap)
One Last Thought
All it takes to pass due diligence is preparedness.
Laura Roeder shared what made selling her SaaS business, MeetEdgar, surprisingly smooth:
“Due diligence was REALLY easy. We had a 30-day period. All our code was in GitHub, and all transactions were in Stripe.”
During handover, when the acquirer could ask anything, she added:
“We’ve always been good about keeping processes and information clear and organized, so there wasn’t a ton to ask.”
Takeaway: Clean, transparent systems aren’t just for show they’re what make transitions seamless.
And that? That’s 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.
