That was the subject line of a recent email with a clear ask that actually caught my attention.
And as an investor who receives dozens of startup pitches and even more follow-ups each week that’s saying something. It wasn’t in a professional tone and it wasn’t polished, rather subtly self-deprecating but undeniably honest.
The sender had decades of real operating experience, named specific companies he’d been part of, explained a personal reason he was contacting us specifically, and referenced something from our own website that resonated with him.
It wasn’t just the subject line that caught me, it felt unmistakably human, a trait that is vanishing from my email communications with others. It wasn’t perfect writing, but it was incredibly refreshing.
I call it out at the risk of getting mountains of copycat emails over the next 18 months.
I, like many other investors, have been at the receiving end of an AI-powered pitch-fest from startups.
There’s a funny irony that some of AI’s most vocal proponents, startup investors, are now at the bleeding edge of homogeneity being bred by its rampant use.
Writing and communication are skills we have always seen value in. When the cost to send an email falls to zero and there is little time invested because the sender thinks it’s a game applying “law of averages” what the sender overweights is that they are building the top of the funnel but actually they underweight how poor written communication immediately lacks credibility and therefore fails to get any real attention and misses an opportunity. It simply doesn’t convert.
Moreover, if you can’t succinctly articulate your unique insight and show an ability to execute in an email, it’s hard to believe you’ll convince investors, recruit employees, win customers, or lead a team.
The email is the audition.
I’m not alone in feeling this AI copy malaise.
We’ve noticed a distinct movement on the internet whereby people are calling out that this was written by them not AI and even adding deliberate mistakes into their communications to appear more human. Even that’s too hard for some: There’s an AI tool that will add typos for you.
Even LinkedIn, owned by Microsoft, one of the world’s most vocal proponents of AI, has said enough is enough. They are starting to crack down on AI-generated posts and it’s about time. When people can’t even muster a sincere congratulations on a new role, or award win, and need to use AI-generated copy to muster one up for them, surely something is deeply wrong.
This is all not to say there isn’t a place for AI in dealing with investors.
I personally think it’s fantastic for refining pitch decks and it definitely has a place with complex cap tables. Like most venture investors, we also expect AI to be built into the operating system of the business and continually evolving, that’s table stakes nowadays. Discernment becomes more critical; when and when not to use AI.
I like to think LLMs are like the greatest cover band in history. They can play anything, flawlessly, on demand. But every song belongs to someone else and they’re optimised to play it in a way the whole room accepts as OK or meh, not wow. There is no risk and therefore no edge which is how they are built.
There’s room for growth here too. I think we’ll see new models emerge, ones with access to unique datasets built around real thought leaders, and tools that genuinely understand how you think and help you refine it. That’s an interesting direction.
But I don’t see a world where outsourcing the thinking completely produces anything of value. The model can learn your tone and mirror your cadence. What it can’t do is have the experience, the scars, the contrarian insight about something that hasn’t happened before – those thoughts make something worth reading. The thinking has to start somewhere human.
So before you push send. Pause and think: Is this message actually communicating well on my behalf? Or is it just really generic?
Because I think I’d prefer an inbox with hundreds of irreverent, but sincere subject lines over mountains of messages that just all sound the same and get immediately discarded.
- Will Richardson is the Managing Partner of Giant Leap, Australia’s first venture capital fund dedicated to impact.
