Tactical insights for first-time founders to outsmart the burn, the churn & the breakdown.

Hey Founder,

You’ve just raised a round. Your days are now filled with hiring, shipping, and fixing what breaks faster than you expected. That’s normal. That’s the job.

What usually gets pushed aside in this phase isn’t execution, it’s continuity. Specifically, the habit that quietly makes your next raise easier: consistent, honest monthly investor updates.

Not a polished board deck. Not a “we’re crushing it” narrative.

A simple monthly field report: what moved, what didn’t, what you learned, what you’re testing next, and where you need help.

Most founders skip this because it feels non-urgent. In practice, it’s the difference between a warm next round and a cold one.

This issue breaks down how monthly updates compound trust with current investors, and start pre-selling the next raise long before you need it.

Let’s get into it.

Most founder–investor relationships still revolve around events: a pitch, a quarterly update, then silence. But trust isn’t built in presentation mode. It’s built in the middle, when results are uneven, experiments are running, and you show up without a narrative to sell.

That’s the real value of monthly updates: continuity.

Tyler Denk at Beehiiv did this for years. He sent honest monthly updates not just to investors, but to people who had passed, operators he respected, and future investors he wanted to stay close to. No fundraising angle. Just metrics, what worked, what didn’t, and what he was testing next.

So when Beehiiv raised its Series A, there was no “catch me up.” The Lightspeed partner already knew the story, not the highlights, but the trajectory. The round closed in six days.

As Mark Suster puts it, investors don’t invest in dots, they invest in lines. Monthly updates turn you from a snapshot into a track record.

When you finally say “we’re raising,” it doesn’t feel like a leap of faith. It feels like reviewing a credit report, one you’ve been building all along.

This isn’t hygiene. It’s leverage.

Most investors aren’t unwilling, they’re uninformed. A monthly update that includes one or two concrete asks gives them context and a clear way to engage, without forcing them to guess where they’re useful.

Early‑stage investors live in constant noise. The companies that show up monthly stay top of mind; the quiet ones fade into a vague “I wonder what happened there.” Consistency, especially when you’re not raising, keeps you in the first category.

Founders who send updates don’t “announce” a raise; they arrive at it. By the time capital is needed, investors have already seen the progress, the missteps, and the learning curve. Saying yes feels natural, and the investors who passed quietly start paying attention again.

If you treat them as something you owe your investors, a way to “keep them warm”, they’ll always feel like homework. Performative. Easy to postpone.

A more useful frame is this: your monthly update is a self-debrief that happens to be shared.

Once a month, you’re forced to slow down and answer questions most founders avoid when things are moving fast: what actually moved the business, what didn’t, what you learned the hard way, and what you’re changing next. You also make explicit where you’re stuck, instead of carrying it quietly.

That exercise is valuable even if no one ever read it. The fact that investors do is incidental.

Seen this way, it stops being about “updating the adults in the room.” It becomes a personal checkpoint, a way to make sure you’re not narrating progress that isn’t really there.

Investors get a clear window into how you think.
You get a recurring moment of clarity when it’s hardest to create one.

This only works if it’s easy. If updates feel like a project, they won’t survive a bad month.

Use the same structure every month. Not because it’s elegant, but because it removes friction.
Same subject line. Same order. Same sections.

If this takes more than half an hour, you’re overthinking it.

Only sending updates to your cap table misses the point. Include:

The rule is simple: if someone has context on the business, keep them in the loop.
The invite doesn’t need a ceremony.
“I send a short update every month. Want me to add you?”
That’s it.

Most founders don’t stop sending updates because they forget. They stop because the month wasn’t great.

Put it on your calendar as a recurring block. Same day, same time, every month. When the hour is up, you send whatever is true.
No polishing. No waiting for a better story.

If you miss two months in a row, don’t treat it as a habit problem. It usually means you’re avoiding something in the business, and that’s worth paying attention to.

Straight from my DMs:

Start with burn. Always.

Keep what you need for the next ~90 days in your operating account. That’s payroll, vendors, and the stuff that keeps the lights on.
Anything beyond that is no longer operational cash; it’s idle cash.
That’s the portion that belongs in a high-yield business savings or money-market account.

If you’re consistently sitting on more than ~$50k of stable, unused cash, you can look at sweeps or debt paydown, but only if fees are minimal and cash flow is predictable. Liquidity comes first.

If you rarely have more than three months of runway, don’t bother optimizing yield yet. The upside is small, the setup is annoying, and it won’t move the thing that actually matters.

Financial optimizations are useful.
Just don’t optimize pennies while dollars are still on fire.

Send it my way, just hit reply.

A few things worth your time this week:

Before You Go…

Bezos’s and Buffett’s shareholder letters are legendary now, but they didn’t start once they “made it.” They started as regular updates, written for years when almost no one was paying attention.

If you have any ambition to one day write a great S-1, a candid “we sold the company” note, or a real post-mortem after a miss, you don’t need another framework.

You need evidence.
Twelve months. Twelve updates.
Twelve receipts of how you actually think when things are in motion.

Block one hour a month. Send the update.
If your next raise isn’t warmer, faster, and less painful, you can drop the habit.
But you probably won’t.

See you next Thursday,

— Mariya

Hit reply and let me know. I read every single one (for real).

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.

Mariya Valeva

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