a s*** proposal

Here’s a myth I bet you believe:

A proposal wins when it proves one of two things:

I believed it for years. And in year one of my first company, JRNY, it nearly sank us.

Here’s how I “did proposals” back then:

Someone would ask for one. I’d get excited, build the most compelling document I could, and email it over.

I’d make the price as low as I possibly could.

And I’d cram in every feature I thought they might possibly want.

Then I’d sit and wait for the reply…

Most of the time it was a version of “we’ll review internally and circle back.”

(In some cases, no reply at all).

When someone did say yes, I was charging $200 a month. For a product we’d spent a year building.

BUT then I learned a different way to structure a proposal, with a different method of presenting it.

I went from charging $200 a month to $10,000 a month.

Kinda wild, right?

Nothing about what we sold had changed. What changed was what the document was doing (and who it was being sold to).

The $200 proposal was trying to be cheap and trying to be impressive. The $10,000 proposal was trying to prove one thing:

Then it showed them the path to get there.

That’s it. That’s the whole job of a proposal.

Once they believe you get it, “cheapest” loses its power, because they’re no longer comparing like for like. “Best” loses its power too, because they’ve stopped judging you on a feature list.

They’re judging you on how well you understood them.

Remember: Nobody cares about you. You must make the proposal about your prospect.

If they don’t see themselves on every page, you’ll lose the deal.

So here’s the structure that took me from $200 to $10,000 (and the one I still use today, only ever after a proper discovery):

1. Their logo and their desired outcome on the cover. Open on them.

2. How we got here. A short recap of discovery. Proves you listened.

3. Where they are now. Their current problems, in their exact words. Use a meeting recording to capture the exact wording.

4. Where they want to be. The future state with those problems gone.

5. What’s at stake. The cost of staying where they are.

6. Your tailored solution, mapped point by point to their problems. Their biggest hidden fear at this stage is ambiguity, and defined scope says “I’ve solved this before.”

7. Timeline and investment. Priced against the stakes they just agreed to, so the number lands with context.

8. One matched case study and a prescribed next step. One story like theirs beats a wall of logos. Then tell them what happens next, like a doctor would.

Notice how far down you get before you ever talk about yourself?

And THAT is how you win a proposal.

There is one more rule you must follow:

The first time your prospect sees the proposal, you are presenting it live.

Emailing it was my other big mistake at my first company. Email it and it gets skimmed on a phone, the price lands in a vacuum, and it gets forwarded to a co-founder or a board member who missed the whole journey. When they say “just send it over,” hold off and use this line: “I would love to but I need to walk you through it. Can we chat at [time]?”

And boom - your proposal meeting will be set.

This is one of Sollo's many capabilities.

It builds the proposal for you from what the prospect actually said in discovery. Plus, there is a Canva template in the Sollo community.

Join as one of the first 100 and $97 a month is yours for life, instead of $247. Oh, and there’s a 14 day free trial so there’s literally no reason not to give it a go...

Do this today: audit your last proposal and see:

Fix those, and you'll start winning way more profitable deals.

Power to you,

Mike