Every founder I know bills monthly.
It sounds normal — predictable, even.
But monthly billing quietly kills your runway.
The Gap
In researching founder cash flow tactics, I found four bootstrapped founders who freed up an extra 30 days of cash.
They didn’t raise prices or ship a new feature.
They just changed when they got paid.
That small shift completely changed their stress level.
The Pattern
Most founders doing $10K–$15K MRR bill monthly.
Cash shows up every 30 days.
Burn happens every single day.
The result? You’re always 30 days behind your own business.
The founders who sleep better? They collect cash upfront.
The Stories
Sander Fish ($15K+ MRR):
Started requiring full payment before custom feature work.
“We start once the invoice is paid. Full amount.”
Abhi (indie dev):
Built a project on trust alone. Client disappeared.
“Never work without an invoice, no matter how convincing someone seems.”
Shan Han (agency → SaaS):
Signed a huge contract with Net-30 terms. Payment came 90 days late.
“I emptied my savings just to make payroll.”
Marty Kausas:
Scaled from $2K ARR to $30K ARR. The shift? Annual upfront instead of monthly.
Common thread:
Monthly billing creates chronic cash anxiety.
Upfront billing creates oxygen.
The Math
Let’s put numbers to it.
Say you’re doing $12K MRR, burning $4K/mo, and you’ve got 3 months of runway left.
If you convert just 3 customers from $100/mo to $1,000/year:
💰 You collect $3,000 today
🏃♂️ Runway extends to 3.75 months
🛠️ No product changes required
Formula:
The Math
Let's put numbers to it.
Say you're doing $12K MRR, burning $4K/mo, and you've got 3 months of runway left.
If you convert just 3 customers from $100/mo to $1,000/year:
Step 1: Calculate cash injection 3 customers × $1,000 = $3,000 collected today
Step 2: Calculate extra runway $3,000 ÷ $4,000 monthly burn = 0.75 months (≈23 days)
Step 3: Add to current runway 3 months + 0.75 months = 3.75 months new runway
Formula: Extra Months = (Cash Injection) ÷ (Monthly Burn) New Runway = Current Runway + Extra Months
🛠️ No product changes required—just timing.
It’s that simple — cash timing buys you time to breathe.
The Tactic (Use This Email)
Pick your 5 happiest monthly customers and send this:
“Hey [Name] — we’re offering 2 months free if you switch to annual billing this quarter.
$1,000 today instead of $100/month.
Lock in your rate — I get predictability. Win-win?”
Offer: 2 months free (16% discount)
Psychology: They’re already happy — you’re just changing timing
Urgency: “This quarter only”
Even two conversions can add 60 days to your runway.
Why It Works
Monthly billing optimizes for flexibility.
Annual upfront optimizes for survival.
At $10K–$15K MRR, survival should come first.
And one hard rule:
Never offer Net-30 unless they’re paying annual upfront.
A Real Example
Here’s how Sander Fish reframed his customer conversations:
Customer: “Can you build X?”
Old way: “We’ll add it to the roadmap.”
New way: “Sure — $5K upfront and we start Monday.”
Now he builds only what’s already paid for.
Immediate cash, committed customers, faster shipping.
Next Week
💡 The Churn Paradox — why $20K MRR founders obsess over it, but $8K MRR founders ignore it.
Founder Call
If you’re a bootstrapped SaaS founder doing $5K–$50K MRR,
I’m interviewing 100 of you about your financial systems.
👉 Book a 45-minute chat: Click here
To your runway,
Abraham Thompson (@IntelAbe on Twitter/X)