Your suggestions are interesting, but I'd rather focus on the real customer, and have the numbers speak for themselves, rather than simply perfecting the art of raising money.
I've founded startups in the past, raised money, and also invested both as angel investor and as a founding member of a micro-VC fund (and currently operating partner at a large VC fund, but not too relevant here).
In my personal experience, building a strong company most often trumps a founder's ability to play smoke and mirrors in front of an investor.
The founders that over index on what they think an investor wants to hear almost without lose me within the first minute. I’m not buying your 5yr projections. It’s not believable that you’re literally the only other company in the top corner of a competitive quadrant. Try and pitch me about the tax efficiency of my potential investment and we’re done. Sometimes a founder forces a deep dive and what typically surfaces is they have a pretty superficial understanding on most of this stuff and we end up a multitude of holes or inconsistencies in what got pitched. It’s not their fault, they’ve only learnt enough of this stuff for the sake of fundraising because that’s what someone somewhere told them they had to do. A meeting that ends with the overwhelming sense you didn’t know your stuff isn’t going to end with an investment.
Contrast that to the founders I’ve invested in. One I contacted originally because I was building a competitive product. A few referrals from people I know with “they could use a little help, would you mind having a chat and giving them some advice?”. More than one of those I thought was not a particularly viable idea and planned to help the founder map a path to working that out themselves as quickly as possible. Instead I walked away from all of those conversations feeling like a knee nothing. That I’d just been gifted a brain dump from one of the most insightful people I’d come across. And that they’d introduced me to a whole exciting new area of potential I’d been completely oblivious to only an hour earlier.
I definitely want to hear a different story to what you’d represent to a customer. I think people would be more successful if they gave me the version they’d give their first dozen employees and not the one they think investors want to hear.
What has been your experience using this strategy? Is there anything in particular that makes you say that?
Building a strong company also requires a different set of skills and much more work. Not everybody has those skills, or would want to develop them if their goals can be achieved by hacking the system.
Looking at cases like Theranos and WeWork, there's definitely something wrong with the game itself. The fake it-till-you-make-it culture is a little too prevalent to dismiss.
You are selling a product to a single customer (or small group of them). That product is an investor story that can sell for hundreds of thousands or even millions of dollars if you tell it ably enough, so it's worth putting in the time in to tell it well.
If necessary, you can even write a little toy website, and entice people to sign up for it, in the service of that story. If you can get yourself to believe in the story, you will be all the more persuasive in convincing that key customer.
But never forget that your primary focus is that customer—your investor. Learn their interests, learn to speak their language (perhaps by reading posts like the parent), learn how to flatter their sense of self until they feel like a genius visionary for finding you.
Startup investing is a luxury lifestyle product for the very rich. The art of selling that product well is pretending that the transaction is something different than what it is.