The night I priced myself out of business (and how I fixed it)

Picture a kitchen table at 1:13 a.m. Coffee ring on a notebook. A pricing page open on my laptop that looked like an apology letter: $9, $19, $29. Friendly. Approachable. Lethal.

We had signups. We did not have a business. Every support ticket felt like a negotiation with my own self‑respect: “Could you add SSO for the $19 plan?” I said “maybe” too often because I was afraid of charging like an adult.

Two things changed my mind.

First, Jason Cohen’s line landed like a thud in my stomach: if you’re self‑funded, build a cash machine—predictable revenue that pays the rent—then scale that on purpose. Second, Rob Walling’s calm sequence reminded me there’s no magic: start from problems, price to value, market before you code, and launch in phases so you don’t burn your best list.

This is the story of how I took that advice, one unglamorous step at a time, and turned a lottery ticket into a machine.

If you’ve ever raised your price and immediately opened a new tab to check if anyone is mad at you, we’re friends now.

Raise your hand if…

• You’ve offered a “free 14‑day trial” that quietly burned a month of cash and taught you nothing.
• You launched to “everyone” and got noise instead of retention.
• You wrote “simpler, faster, better” on your homepage because you were tired and out of nouns.
• You’re undercharging because the product is “still early,” but somehow “still early” has lasted six months.

You’re not broken. Your model is.

The antidote is embarrassingly simple: boutique pricing, annual prepay, and a phased launch—under a positioning statement that punches the real alternative (meetings, spreadsheets, Slack purgatory), not just competitors.

Let me show you how this actually looked in the room for me.

The Cash‑Machine Framework I wrote on a sticky note

I wish I could pretend it was a grand plan. It was a neon sticky note stuck to my monitor for a month.

• Target: 150 customers × ~$70 ARPU ≈ $10.5K MRR per founder.
• Pricing: price like a boutique (clear tiers, a “Business” plan for grown‑ups, highlight the middle).
• Cashflow: push annual prepay with 2 months free; partner coupons work on annual only.
• Positioning: “We replace [ritual] with [measurable outcome]”—and prove it with one honest number.
• Launch: market before code; invite in cohorts; charge as soon as value lands.
• Channels: pick dollar‑in/dollar‑out engines first; social is gravy, not fuel.

It’s not sexy. It is, however, rent.

The morning after the price change

I dragged the $9/$19/$29 page to the trash and wrote what I wished I’d had as a buyer:

• A “Business” tier that included what serious teams actually need (SSO, priority response, usage ceilings that reflect reality).
• A middle plan that looked like a solid default, not a compromise.
• One tasteful decoy (“was $79 → now $49”) so people had something to feel smart about.
• And I swapped the trial for a 60‑day money‑back guarantee. I took the card up front. Under the CTA I typed the sentence I wanted to read as a buyer: “Refund in one click—no form, no feelings.”

Then I hit publish and immediately wanted to throw up.

Here’s the weird part: signups went up. Early churn went down. The guarantee felt safer than a trial. The cash leak stopped.

If you need a sentence to say out loud when your finger hovers over “publish”: “My price is a filter, not a confession.”

The first annual prepay that made my shoulders drop

You don’t forget your first annual. Not because of the money (okay, a little because of the money), but because of the feeling: someone just told you they plan to stick around. That little green “annual” tag in Stripe looks like oxygen.

I put annual right on the page with two months free. No webinar scavenger hunt. I nudged the monthly list price up slightly so annual felt like the adult choice. I gave one partner a code that only worked on annual (“3 months free for [Partner] readers”).

In two weeks, a quarter of new signups chose annual. Month‑zero cash was suddenly more than 3× what monthly alone would’ve delivered. Credit card settles today; ad bill hits next month; I can breathe in between.

If the words “infinite marketing budget” feel like a fairy tale, here’s the boring version: annual prepay just lined up your cash and your calendar.

The line that rewrote my homepage

Customers don’t compare you against competitors; they compare you against rituals. The Thursday status meeting. The spreadsheet that goes stale the minute you open it. The Slack thread with 119 replies and zero decisions.

So I rewrote the hero.

“Stop losing Thursday afternoons to status meetings. [Product] is a [category] for quick updates that actually ship decisions.”

Underneath it: “Cut recurring meetings by ~29% on average—measured across six teams. Early access. Refund in one click.”

Is that number perfect science? No. Is it honest enough to put my name under? Yes. It’s a better promise than vapor.

If you’re stuck, write three “We replace X with Y” lines that would make your favorite customers nod like you’ve been in the room. Use the truest one.

Market before you code (without becoming a “content person”)

I don’t love writing threads for the algorithm. I love building things. So I gave myself a deal: one landing page, one Friday note, and everything points there.

• Landing page first. A/B the headline until conversion isn’t embarrassing.
• Every mention—tweet, DM, hallway chat—points to that page.
• Friday field notes. Not hype. Notes. “We let 250 people in this week. Feature X made three people smile and one person swear. The swear was right; fixed on Tuesday.”

The number of replies to those Friday notes became my meter. “Keep me on” beats “Nice!” every time.

The first Tuesday cohort (and the ping I won’t forget)

We let in 250 people every other Tuesday. Not a waitlist for drama. A pace we could keep.

We charged as soon as someone said, “This saved me an hour.” Not because I’m greedy, but because payment is the adult version of a “like.” If you comp early adopters for life, you blur your instrument panel.

On the first Tuesday, half the cohort asked for the same thing. The old me would have tried to ship all ten by Friday. The new me picked one, did it properly, and wrote the other nine a note: “We heard you. This goes first. You’ll like why.”

Three days later, a Slack ping from a CTO I admire: “Not to be dramatic but this just saved my Thursday.” I screenshotted it and taped it above my desk.

The 30‑minute tune‑up I’d make you do if we had coffee

• Rewrite the hero to punch the real alternative (meetings, spreadsheets, Slack purgatory).
• Add a 60‑day money‑back guarantee; take the card at signup.
• Put annual on the page with 2 months free; make partner coupons annual‑only.
• Raise monthly list price slightly so annual feels like a win.
• Add a “Business” plan; highlight the middle tier; include a decoy price.

Does this feel “salesy”? Good. Salesy is just what useful looks like when you’ve been apologizing for too long.

Metrics that kept me honest (and off the roller coaster)

• ARPU: the early‑stage king. If you can raise price without tanking conversions, do it before buying more traffic.
• Annual mix: aim for ≥25% of new signups on annual. It turns “someday” into “this month.”
• CAC envelope: when you have no data, start here—CPC ≈ ARPU/25. If ARPU is $70 and you’re paying $6/click, you better be converting like a magician.
• Cohort retention: watch who stays and what they used first. That’s your roadmap.
• Refund rate: a healthy guarantee shows up here. If refunds spike, fix the value or the promise—not the guarantee.

Channels that funded next week (not next year)

You can move fast without inventing a brand overnight. My order of operations:

• Partners with annual‑only coupons (clean attribution and clean cash).
• Focused paid search on bottom‑of‑funnel terms (people looking to switch now).
• Integration marketplaces (aftermarkets where buyers already gather).
• Niche newsletters with trusted editors (one good placement beats 50 generic posts).

Nice‑to‑have later: “it might go viral,” brand social, and broad content plays. If a channel can’t answer “dollar in → dollars out, when?” it’s a hobby for after you’re funded or rested.

Red flags I wish I’d respected sooner

• Free trial + no card on file + no success path = cash bleed and noisy signals.
• Commodity headline (“simpler, faster, better”) without naming the alternative.
• Annual buried behind a sales call.
• Lifetime deals for a launch‑day dopamine spike.
• Launching to everyone at once because you’re “running out of time.”

If you see one of these in your mirror, you’re not in trouble; you’re in decision.

Scripts you can steal and say in your voice

Price change without sounding like a ransom note:

“We added priority response, SSO, and usage ceilings that reflect how customers actually use us. New pricing starts next month; if you’re already on a plan, you keep it. If you want the new features, here’s a one‑year coupon for 3 months free (annual only).”

Early access invite for grown‑ups:

“You’re on this list because you raised your hand early. We’re letting in 250 people this week. It’s not everything yet, but it’s useful. If you get value, we charge monthly or annual (2 months free). If you don’t, hit refund in the app—no form, no feelings.”

Partner CTA that nudges annual:

“Readers of [Site] get 3 months free when you choose annual. The code only works on annual because it’s meant to make your CFO smile.”

Say them once out loud. Your shoulders will drop.

A one‑month plan you can actually finish

Week 1 — Pricing & copy

• Rewrite the hero to name the real alternative and promise one believable outcome.
• Add a “Business” tier. Highlight the middle. Replace the trial with a 60‑day guarantee.

Week 2 — Annual & partners

• Launch annual with 2 months free. Create one partner‑only annual coupon.
• Email legacy customers: keep current plan, or switch to annual with 3 months free.

Week 3 — Landing & cohorts

• Ship landing page v2. Start the Friday field notes.
• Invite the first 250. Charge when value lands. Watch what they actually use.

Week 4 — Tune & scale

• Kill one feature request that doesn’t move revenue.
• Double‑down on the channel with the cleanest CAC payback.
• Plan the next cohort; ship one hard thing the first cohort asked for.

If you only remember three lines from this “talk”

• Your price is a filter, not a confession.
• Annual prepay is cashflow you can think with.
• Launch like you plan to keep people.

I used to think the founders who “made it” were louder, braver, everywhere at once. Turns out, the ones I want to copy are just steadier. They price like adults, take cash up front, write sentences that sound like a person, and launch like they intend to keep customers.

If you’re tired of the lottery, build the machine.

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