I'm writing this from a café terrace where I've consumed my body weight in croissants and madeleines. So. Worth it.

I was here speaking at SwiftConnection about something that's been keeping me up at night… we're designing AI interfaces that accidentally leave half the population behind.

Turns out even senior iOS developers are hungry for human-centred thinking in this AI gold rush.

The room went quiet. Not awkward quiet, but that focused, "oh shit" quiet when something clicks. Afterwards, dozens of thoughtful questions and several developers pulling me aside to say "you just articulated what I've been feeling for months but couldn't name."

I'll share the full breakdown when the video's live. The principles matter for anyone building with AI or trying to use it effectively which, let's be honest, is all of us now.

But first, something immediately useful for those of you staring down funding decisions...

"So that's actually too much money," the founder said, mid-pitch.

We both paused. They'd spent weeks preparing for this funding round. Investors were ready to wire $1.5M. And here I was, suggesting they walk away from it.

This founder was debating whether to raise $1.5M at a $12M valuation. Sounds brilliant on paper, right? But when I asked what they planned to do with the money, they paused.

"I'd hire another salesperson... maybe an engineer."

Their burn rate would increase by around $15K per month. That's it. With their current bank balance and revenue, they already had 8 months of runway. This raise would extend it to 25 months.

"So that's actually too much money," they realised mid-conversation.

Exactly.

In my experience, there are really only two legitimate reasons to take VC funding:

1. You're pre-revenue with a proven track record

Investors are betting on you, not your product. You've built and sold companies before. You know what you're doing. The money buys you time to prove your new vision.

2. Money is your only constraint to growth

Your business model is proven. Your team is executing brilliantly. Customer demand is there. The only thing stopping you from 10x growth is capital for rapid expansion.

If neither applies to you, taking investment is probably a mistake.

My client was already on track to reach 50% of customers in their market within 8 months. Adding more people might speed things up slightly, but the sales cycle has natural timing constraints. They couldn't meaningfully accelerate the process even with more resources.

Here's how I think about fundraising: The raise should unlock a specific checkpoint—if it's not doing that, it may not be the right time.

A checkpoint is a significant milestone that fundamentally transforms your business trajectory. It's not just doing more of what you're already doing; it's enabling an entirely new phase of growth.

For my client, their first checkpoint was reaching 50% of their B2B customer base. Their next checkpoint was expanding to direct-to-consumer. The $1.5M wasn't enough to fully fund the second checkpoint, meaning they'd need to raise again anyway.

So why dilute now at a lower valuation when they could wait, hit their first checkpoint, then raise at much better terms to properly fund their second phase?

The checkpoint principle works for any major decision.

Let me be clear: incremental progress is how you win. Ship that feature. Call another customer. Iterate on your design. That daily grind is essential.

But when you're considering a big investment, say, hiring that expensive developer, doing that major rebrand, or betting it all on a complex new feature, the checkpoint question matters.

Incremental improvements keep you moving forward. Checkpoints change the game entirely.

Thinking about hiring that developer? If they let you ship faster, that's incremental. If they unlock an entirely new product capability that transforms your market position, that's a checkpoint.

Considering a rebrand? If it looks nicer, that's incremental. If it repositions you to compete in a different market segment, that's a checkpoint.

Every risky resource investment—time, money, attention—should unlock a checkpoint. Save your incremental improvements for your daily work. If you can't articulate the checkpoint for a major decision, you're probably not ready.

If you're worried about runway (and you should be), here's a practical tip I often recommend:

Separate your operating funds from your runway safety net into different accounts.

Instead of keeping all your cash in one place, create a high-yield savings account specifically for your "runway reserve." Each month, transfer a portion of your revenue into this untouchable safety fund.

This accomplishes two things:

My client had healthy cash reserves in the bank. By moving part of it to a separate account as their initial safety net and adding to it monthly, they could build towards a full year of runway protection while still having freedom to invest in growth.

Many founders raise money "just in case", i.e. without a clear plan for deploying it effectively.

This is a mistake.

Every dollar of investor money should have a specific job. If you're raising "for comfort" or "because we can," you're likely to:

I've seen founders raise at the wrong time, then spend years trying to grow into their valuation rather than building what their customers actually need.

The goal isn't to “raise money”. The goal is to build a sustainable business that creates value. Sometimes that means saying "no, thank you" to investor money that doesn't serve your immediate checkpoint.

So here's my question for you: What specific checkpoint would additional funding (or resources) unlock for your business right now?

If you can't articulate exactly how that money transforms your trajectory (not just accelerates it slightly), you might be better off bootstrapping a bit longer.

As my client concluded: "We could grow into a sustainable business, or we could raise and dilute. I think I'd rather just handle business."

Sometimes the most powerful fundraising strategy is patience. And sometimes the bravest thing a founder can say is: "Not yet."

PS — If you know a founder wrestling with fundraising decisions, please forward this email to them or share your referral link! And if you're facing a similar dilemma, I'd love to hear about it - just hit reply.

😍 Did you like today’s issue? Ring this bell 🔔 so I can celebrate!

🤷‍♀ Did you think it was meh? Hit reply and lay your feedback on me!

🤩 Want more? Check out the video below!

Code explained in plain English for founders who need to work with developers

Quick legal note: This newsletter shares my experience and opinions, but it's not official financial, legal, or business advice. Every situation is different. Make your own decisions, do your own research, and consult professionals when you need them. You're the expert on your business.