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Welcome to Cutting Through The Fog.
Each week I share the thinking and frameworks I’ve used (and learned the hard way) to help you build with more clarity, more momentum, and fewer avoidable mistakes.
This week it’s investment timing.
When to bootstrap.
When to raise.
And how to avoid the mistakes that end a round before it starts.
Raising money does not mean you’re a “grown up business”.
It’s not a badge of honour.
It’s a strategic decision.
And if you get the timing wrong, you don’t just waste time.
You lower your valuation and lose momentum.
Business-ready vs Investor-ready
This is worth repeating.
Business-ready means:
You have an idea you’re passionate about.
You’ve got practical insight.
You’ve put a basic plan together.
Investor-ready means:
You have an investment strategy.
You understand the stages of growth and what investors look for.
And you have an investible business.
Many founders are business-ready.
Very few are investor-ready.
When to keep bootstrapping
Keep bootstrapping if:
1) You can deliver traction with the cash you already have.
2) You don’t have an immediate competitor threat breathing down your neck.
3) You can generate enough growth by reinvesting revenue.
4) You haven’t yet formalised your value proposition, your ICP, or your business model.
If any of these are true, waiting is your best bet.
When to raise
Raise if:
A) You are convinced funding will deliver growth, not just runway.
B) You know exactly what the money will do.
A cause-and-effect plan.
If we spend £X on Y, we get Z outcome.
Raise if you have a clear bottleneck that money can remove:
A) Key hires.
B) Essential marketing.
C) Distribution.
D) Product improvement.
The trap founders fall into
Fundraising has become fashionable.
Make sure you’re not just following the crowd.
And never raise as an alternative to revenue.
A business is NOT about fundraising. It’s about talking to customers.
Solving their problems. And charging money for it.
Most startups don’t die because they failed to raise funds, but because they never learned how to sell.
Investor money doesn’t fix that. It just delays the day of reckoning.
So be clear:
You are raising to sell more. Scale. Grow. Not to avoid selling.
What kills a raise (three cardinal sins)
I’ve sat in enough early-stage pitches to know the patterns.
Avoid these and you’ll be well on the way to hearing:
“I’m in.”
1) “We’ll figure out distribution after the raise”
Most startups fail before the pitch even starts.
If you can’t show a repeatable way to get customers without burning huge amounts of time, energy, and money, your problem is not funding.
Your problem is selling.
2) Founder certainty
Founders who are certain, with zero doubt, usually fall into one of three categories:
A) They haven’t tested enough.
B) They ignore data that contradicts the plan.
C) They’re emotionally attached to being right.
I’m personally far more interested in founders who say:
“This is our best guess based on the evidence we’ve gathered.”
“Here’s what we’re pretty sure about.”
“Here’s what we have a good hunch about, and we’re going to test it.”
“Here’s what we’re still winging, and why it’s not the priority yet.”
3) Claiming you want “smart money”, but not listening
Some founders say they want value-added angels.
But the moment they receive advice, they become defensive.
Investors have a simple way to spot this early:
They challenge a fundamental assumption.
A well thought-through counter gets support.
Defensiveness kills trust.
You don’t have to agree with every investor.
But you do have to show you can listen, process, and respond like an adult.
Now, how are deals actually get done?
Very important: Raising a round is a sprint, not a marathon.
However: Building relationships is a marathon, not a sprint.
Read that again.
Speak to investors long before you need the money.
When you are ready to raise, build momentum deliberately:
Start with confidence. Create urgency without desperation.
Signal to the whole investment committee, not just the person you met.
Run an organised data room and improve it after every meeting.
Secure a lead investor quickly, but choose them carefully.
The wrong lead drops out and kills the round.
Key ways to lose trust and lose a deal
This is the stuff that kills deals:
1) Slow responses and missing materials.
2) Founder misalignment.
3) Flip-flopping on valuation or terms.
4) Late disclosure of critical issues.
5) Misrepresenting traction or financials.
6) Hustle that turns into desperation.
7) Dragging the process too long.
Investors don’t just evaluate the company, but how you run the investment process.
Fundraising is a mirror of future execution.
If it’s sloppy now, it will be worse later.
Closing the deal
“What would you need to see in order to make a decision?”
When someone decides, move fast.
Never tell an investor to wait. Close as fast as you possibly can.
Speed is a weapon.
The longer a deal stays open, the higher the probability it dies.
Deals don’t close because investors are convinced.
They close because founders lead the process, control the tempo, and remove friction.
Final thought
If you’re considering raising, answer these two questions in writing:
Can we grow meaningfully without external capital for the next 6–12 months?
And if we raised tomorrow, what exactly becomes true that isn’t true today?
If you can’t answer the second one clearly, you’re not fundraising.
You’re hoping.
