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

Hey Founder,

Somewhere in your business, 2–5% of your ARR is slipping away. Not a pipeline you might close someday, but revenue you’ve already earned, but that never makes it into your bank account.

On paper, everything looks fine. ARR is growing, the model says you’re on track. But in reality, the cash never quite lines up. You stay cautious on spending, hold back on hires, and still feel like the runway is shorter than it should be.

That gap usually comes from small, unglamorous leaks between selling, billing, and collecting. Deals marked “Closed Won” that sit unbilled for weeks. Discounts that quietly stick around. Customers paying late because no one is really following up.

Individually, none of these seems critical. Together, they add up.

And when you fix them, nothing about your growth changes; you just start getting paid for work you’ve already done.

I’ve seen companies unlock $50–100k in cash without signing a single new customer, simply by tightening billing and collections.

This issue is about that missing cash and how to stop letting it slip through the cracks.

Let’s dive in.

Revenue should be simple: close, deliver, bill, collect.

In reality, most startups end up with a mix of tools, handoffs, and “we’ll fix it later” workarounds. The more moving parts you add, the more places revenue quietly leaks between ARR on paper and cash in the bank.

And this isn’t just a startup problem. It’s everywhere. Large organisations (as per BCG) lose significant revenue every year simply because their billing and collections don’t fully capture what they’re owed.

At the company level, Chassi found an industrial services firm leaking about 8% a year - roughly 21M - simply between contracts, billing, and collections, without anything being “broken” in an obvious way.

In SaaS, the numbers are smaller but just as real. It’s common to see 1–5% of ARR quietly disappear through billing gaps, failed payments, or unenforced terms.

At $10M ARR, a 3% leak is ~$300k a year. That’s real budget - hires, growth, or the difference between breaking even and burning. And at a 7x multiple, that same leak translates into millions in lost enterprise value.

More importantly, in today’s market, this isn’t just about numbers. If you work hard to win revenue and then casually leak it, it signals a lack of control.

The good news is you don’t need another tool to fix this. You need a different way of looking at revenue, and some very unglamorous discipline in how it’s managed.

Founders tend to describe GTM as a path from lead to demo to proposal to Closed Won.

But the funnel that actually drives runway starts after that: sell → contract → provision → bill → collect → renew → expand

You don’t grow when deals close; you grow when cash shows up.

Most leakage happens after “Closed Won,” when everything that follows is unstructured or loosely owned.

So even if sales are working, your cash funnel can quietly work against you.

These are patterns I see over and over.

Individually, these feel like small operational gaps. Together, they point to the same issue: no clear ownership of what happens after the deal closes.

And that’s where revenue starts to leak.

Now, before fixing it, it’s worth checking if this is actually happening in your business.

If your ARR is growing but cash and runway don’t feel as strong, run a quick check this week. Look at whether Closed Won is growing faster than cash collected, how many invoices drift past terms, and whether you’ve recently “found” revenue that was never invoiced or discounts that never expired.

If any of that sounds familiar, you’re not dealing with a growth problem yet, you’re dealing with a payment discipline problem.

And that’s fixable.

Here’s how to start plugging those leaks over the next 30–60 days.

This is the space between what you sold and what actually gets invoiced.

It shows up in simple ways: deals marked Closed Won but never billed, invoices going out weeks late, or usage customers being undercharged because the data is messy.

Give this one focused pass over the next 30 days. Compare contracts, invoices, and cash across your top accounts and look for gaps. Then simplify how invoicing happens: fewer manual steps, fewer exceptions.

One rule helps here: a deal isn’t done until there’s an invoice in the system with an amount and a due date.

Most companies “find” a meaningful amount of money just by fixing this.

Here, billing happens, but cash arrives much later than it should.

Net-30 quietly becomes Net-45 or Net-60 because no one really owns collections, and follow-ups only happen when cash gets tight.

Treat this like a core motion. Put in a simple reminder cadence, assign clear ownership for collections, and start tracking how long it actually takes to get paid.

This is the slow bleed from “just this once” decisions that never get reversed.

Discounts extend far beyond their intent, reps over-discount to close, and credits get used to smooth problems instead of fixing them.

Make discounts visible and finite. Every exception should have a reason, an owner, and an end date.

And periodically review your most discounted accounts; those are usually where margin is quietly leaking.

This is what stops the problem from coming back.

Without it, you fix things once, “find” money, and six months later you’re back in the same place.

Put a simple structure in place:

When this has a name, an owner, and a number, it stops being invisible, and starts improving.

A founder messaged me this week:

This is a common confusion, but it’s usually easier to diagnose than it feels.

If most leads are ignored, hard to reach, or quickly dismissed as “bad fit,” it’s likely a marketing issue. You’re generating volume, but not the right kind.

If leads look solid but nothing converts, slow follow-ups, long cycles, deals drifting into “no decision” - that’s usually a sales problem. The input is there, but the conversion isn’t.

The simplest way to look at it is where things start to break. If the drop happens early, between lead and real opportunity, it’s marketing. If it happens later, between opportunity and close, it’s sales.

Most teams debate this endlessly in meetings, but the answer is already sitting in your funnel.

The quickest way to get to it is simple: ask your reps to walk you through a few recent lost deals and explain what actually happened.

Their answers will tell you whether you have a demand problem, a sales problem or, more often than people realise, a revenue integrity problem where activity looks healthy, but cash never quite catches up.

Send it my way, just hit reply.

Some reads this week for founder wisdom:

Before You Go…

You’re already doing the hard part, convincing people to buy and delivering real value.

If you’re not consistently getting paid for it, the fix isn’t a big transformation. It’s a handful of decisions, clear ownership, and some very unglamorous discipline.

And when you get it right, it feels almost unfair.

Because running a business that actually collects what it earns…
Is the real moat. 

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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