- Milly Barker
- Jun 25
- 8 min read
Updated: 4 days ago
This just in: raising money is hard.
You've got to fit into so many brackets to be able to successfully raise cash (and have quite specific demographics, let's be honest...).
You need to be an 'investible' business, you need to show initial traction, have good unit economics, show that you're able to scale without breaking, have an exit strategy, and manage to communicate all of this to the people who hold the purse strings - the very busy, very (understandably) judgemental, and very over-subscribed people who hold the purse strings.
Even if you do hit the criteria jackpot, you might fail to get a good outcome for yourself - raise on the wrong terms and you could see the fruits of your hard work going to everybody but you when you exit.
Lucky for you, this is a block I've been around more than a few times. Despite looking like a 15 year old work experience kid who accidentally stumbled into the boardroom and is now too embarrassed to leave, I've been at this for 20 years. I've been a hands-on COO for a while now and I've helped with raises worth over £100m.
I'm going to help you figure this crazy shit out - we're going to build a path to investment readiness via some excellent operational discipline. In this new series of articles, we're going to learn about all the critical areas of your business that investors will scrutinise:
Strategy: how to define, refine, and document your path forward (this article)
Operations: assessing and optimising for genuine scalability.
Finance: building robust models and projections that stand up to scrutiny.
Collateral: preparing comprehensive due diligence materials and data rooms.
Coaching: getting ready for the tough questions with due diligence prep and Q&A coaching.
Investment Strategy: mastering cap table planning and investor identification.
I'm writing this series (in part, I'm also writing it because it's really useful) because I just launched a new Investment Readiness service to help startup and scaleup Founders and Operators get the best raises on the best terms by honing their operational effectiveness - we call that service 'Op Eff It' because there are few things I love more than a cute play on words.
Or, if you can't wait for the rest of the series, why not get ahead of the game and take Op Eff It's free Investment Readiness Healthcheck to assess how you're doing right now across all 6 of the categories?
Let's get stuck in.
What is 'Strategy'?
Fun fact, I've written a whole book about just that very thing. It's called How To Write Your Strategy and here's what the introduction to that book says:
"A Strategy is like the circulatory system of your business, carrying information from the top of your plan to the bottom and connecting everything in between. It’s what you’re doing, why you’re doing it, and how. It’s a living, breathing part of your company that weaves together every department, every person, every Task. It’s the detailed plan of action that takes you from the time before you’ve even opened the (physical or metaphorical) doors to your business, to the day that you’ve achieved all the goals. It’s also a big part of the power that gets you to those goals.
Your Strategy tells you what to do today, how far you need to go, where and how far to go tomorrow, and how you’ve been doing on your progress since you started.
A business without a Strategy is like an empty shell that’s being blown down a road - it’s moving, sure, but there’s no control over where it’s going or when, and there’s nothing to stop it crashing into a wall and nothing to start it up again when it does."
The rest of the book covers my framework for Strategy design, which has 6 parts - The Mission Statement, The Objectives, The Key Results, The Projects, The Tasks, and Performance Management.
If you want to learn more about how to build a good Strategy, you can get your copy of How To Write Your Strategy here.
Why does your Strategy matter to your investment readiness?
Because your Strategy is the difference between your business looking like a bit of a gamble and it looking like a genuine, investible opportunity.
Clarity = confidence
Investors are busy people, and honestly, sometimes they’re looking for reasons not to invest in you. If your Strategy is an opaque mess - i.e. if you can't clearly (quantitatively) articulate exactly what you do, who it's for, and how you're going to do it - then you’re a massive risk.
A transparent strategy tells potential investors that you know what you're doing, you’ve actually thought this through, and you have a defined plan to get from A to B without breaking. It screams competence, and competence breeds confidence, and confidence opens the purse strings.
Strategy is a blueprint for scalability
I'm sure you've heard of 'scalability,' but what does it actually mean?
Scalability means being able to grow your business without it imploding under its own weight. And one thing you certainly can't scale is chaos.
Your Strategy acts as the blueprint for building repeatable, efficient operations. If you know your target market, your unique selling points, and how you plan to acquire customers, you can build processes that work at five customers, fifty, or five hundred. Without that clear direction, trying to scale is a frantic, unsustainable scramble, and, trust me, investors can spot that a mile off.
Strategy mitigates risk
Investors are obsessed with risk.
Your well-defined Strategy isn't just about showing them your grand vision; it's about showing them you've actually thought about what could go wrong and how you'll deal with it. A robust Strategy identifies potential market shifts, competitive threats, or operational hurdles, and it outlines how your business plans to navigate them.
All of this is great because it demonstrates foresight and a mature approach to building an actual business, which is going to de-risk the investment in the eyes of the investors because you’re not just hoping for the best - you've also got a plan for the worst.
Strategy increases team alignment & improves execution
Although this entire series of articles is about how to charm investors, your Strategy isn't just for them - it's also for your team. A clear strategy ensures everyone, from your Co-Founder to your most recent hire, understands the Mission and their role in delivering on it.
When everyone is pulling in the same direction, understands the actual priorities, and sees how their daily list of Tasks contributes to the bigger picture, execution becomes infinitely more efficient.
This high level of internal alignment and operational discipline are exactly what investors want to see, because it means you're a whole lot more likely to be able to deliver on the promises you made in your investment deck.
How do you best show off your Strategy to investors?
Obviously, it's not just enough to have a Strategy, you have to be able to show it off. You might be deep in the weeds of it every day, but this is brand new information to your potential investors and you need to be able to show it off in its best light.
There are two key things to consider if you want to properly showcase your Strategy
Make it visual AND verbal - it's a balance
Documenting your Strategy does not mean writing a lengthy, lengthy document that you'll never look at again. What you need is a concise, living, breathing visualisation of what's what.
You need something that’s clear, easy to access, and genuinely helpful.
This isn't just a tick-box exercise for investors; it's your operational playbook - you're actually going to be using this Strategy to execute with your team so make it suit both purposes.
Personally, I like a Miro board, a virtual whiteboard that's accessible to anyone working anywhere. A Miro visualisation of your Strategy can allow anyone to follow the thread from a single Task all the way through to the overarching Mission of the company and it can play really nicely with your communication tools (like your project management system), but it's also REALLY easy to screen-grab and put into an investment deck.
Include your metrics
How will you know if your Strategy is actually working? Only by measuring it. The sixth and final part of a full Strategy is Performance Management.
The way that you communicate your Strategy to your investors of your Strategy needs to clearly outline the key metrics (Your Objectives and Key Results) you'll track to gauge your progress. These aren’t just vanity numbers to get investors excited about how much you're going to grow; these are the genuine indicators of whether you’re already on your way there.
Investors will want to see these, and they’ll want to see that you’re religiously tracking them. It shows you're serious, accountable, and understand how to manage your growth, not just dream about it.
Is YOUR Strategy showing off investment readiness?
Now you know what Strategy is, why it's important for investors to see a good one, and why you absolutely need to get it out of your head and onto paper, it's time to interrogate yours. Is your Strategy ready to be taken out as a tool for raising you the cash you need?
Answer these ten questions honestly to start to get an answer on where the current gaps are.
Can you explain your entire Strategy to anyone in under two minutes, without them having no idea what you're talking about? If it's a complicated mess in your head, it'll be indecipherable to an investor.
Do you know, with absolute clarity, the exact problem you're solving and for precisely who you're solving it? 'Everyone' is not a customer segment.
What makes your solution truly unique? Not just 'better', but genuinely different or more compelling than anything else out there? Investors want to see differentiation to be able to see defensibility.
Can you clearly articulate exactly how your business makes money, and crucially, how that revenue model scales as you grow? Remember - quantitative is communicative.
Have you actually put your core assumptions to the test with real customers or solid market data? Hopes and dreams are great, but evidence is better - no matter how early on you are in the journey.
Do you have clear, measurable metrics (Objectives and Key Results) that tell you if your Strategy is actually working, and are you tracking them religiously? You can't manage what you don't measure.
Are your current operational capabilities and team realistically capable of delivering on your strategic ambitions for the next year or two? Grand plans need solid execution - can you scale what you have?
Have you genuinely considered the biggest potential risks to your Strategy (market shifts, competition, execution failures) and how you'd tackle them? Showing foresight builds confidence that you can weather the storm.
Can every single person in your company, from top to bottom, tell you what your core Mission is and how their work contributes to it? Alignment means everyone's pulling in the same direction.
Is your Strategy plan a living, breathing document that you regularly review and update, or is it gathering dust somewhere? A static Strategy is a dead Strategy - the market will move and you need to too.
Take the time to answer these questions honestly. Your answers will give you a pretty good indication of whether your Strategy is robust enough to attract the right investment, and more importantly, to actually execute and scale your brilliant idea.
If you’re struggling to answer any of them, or want any additional help, just give me a shout via the link below or why not get ahead of the game and take a free Investment Readiness Healthcheck to assess how you're doing across all 6 of the categories?
Otherwise, I'll see you next time we'll be diving into how your Operations contribute to your investment readiness.
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