
I've spent the last fortnight interviewing investors. After a raise there's real pressure to scale quickly, and our clients have been asking for somewhere to work through that with people who've been there. So we're starting to bring some of the best minds on both sides together around it, and I wanted to hear what investors see from their side of the table first.
I asked each of them the same question. After the money lands, where does it go wrong?
(Brittany, who's helping me build it, gave me one note after the first call: I ask a question and then answer it myself before anyone else gets a chance. There’s a reason Anna runs all our research interviews! So for the next few I asked, and then sat in the silence. Uncomfortable, and far more useful.)
The answers overlapped more than I expected.
One investor described founders throwing money at problems they haven't diagnosed. The classic is hiring salespeople and marketers to push harder on a funnel that isn't converting, before anyone has worked out why people aren't buying. Another talked about the US plan that turns up before the UK is nailed. Another about hiring decisions put off for months, then made in a rush.
I understand every one of these. You've just raised, the board wants to see the money working, and hiring is the most visible way to show it. The pull is real.
But capital makes whatever you already do louder. If conversion and positioning are shaky, a bigger team gets you a more expensive version of the same shakiness, faster. And the reorg that follows costs you months, which one VC reckoned is what really kills momentum.
One investor said something I've been chewing on since. In his experience, the amount of personal brand work a CEO does is often inversely related to how well the business is doing. The loudest founders on LinkedIn, he said, tend to have the weakest businesses. The ones doing well are heads down.
I post on LinkedIn a lot and it’s been a very strong acquisition channel for my business so I took that personally for a hot second.
Then I decided I only half agree with him. A founder whose thinking an investor has been reading for 6 months walks into the first meeting with some of the trust already built. Done well, a personal brand makes raising easier, and hiring, and selling.
He's right about the version that goes wrong, though. The founder posting event selfies at 10pm while the funnel needs fixing, counting their own reach as a growth number, and mostly talking about themselves. Investors can spot that from a mile off.
What separates the two is what the brand is built on. The thing he rated most was proof. Case studies and customer references, he reckoned, are worth 10 times a conference slot or a LinkedIn following, especially in B2B. If a big insurer raves about you, word reaches the next few insurers on your list before you do. And if you can't describe your product in one sentence, you can't sell it.
So the founder brand that works is a clear point of view backed by what customers say about you. Investors respect it and buyers trust it.
Your buyers now ask an AI tool who to shortlist, check social for proof, then Google you by name. All of those reward the same thing: other people saying specific, credible things about you. Our Organic Strategist Beka found that in a low-competition niche, around 16 external mentions can put a brand in the top 10 of AI answers. A named case study with a real number in it is exactly that kind of mention. A founder's opinion on its own mostly isn't.
So I'd treat visibility as one job across Google, AI search and social, with customer proof at the centre. The founder owns the point of view and the replies, and that part can't be handed over. The team owns finding the proof, writing it up and getting it published somewhere other than your own website.
Another investor made the same point from the funding side. Polished decks are table stakes now that AI writes them, and he put the average time an investor spends on one at around 10 seconds. What he looks for is traction, customer evidence and a live demo. Same answer, different audience.
Ask your team to pull up your last 10 customers and mark each one against two questions:
That's your proof count. If it's under 3, closing that gap is a better use of next quarter's marketing than anything that adds volume. It also gives the founder's posts something real to stand on.
Drop me a line and tell me your number out of 10. I'll tell you honestly where I'd start, including when the answer is that you can fix it without anyone's help.
PS. More on what we're building soon. If you've raised in the last couple of years and this is a conversation you'd want to be part of, mention it when you reply and I'll keep you posted. Declared interest: it's also how we meet founders who might one day want a fractional CMO and a senior team to deliver the plan, so discount my generosity accordingly.