In general: always be extra nice to HR. They are underpaid, under-appreciated, under-loved, put in the middle of every dispute, and told to make the impossible possible. Like IT, but with squishy meat bags.
"Good thing nothing is up to you, then"
This is invaluable advice. I had a similar problem when returning to the market after years doing my own things. Someone here suggested leaning into the failed startup I’d attempted with a colleague rather than downplaying it. Despite that, I still had a tough time getting initial calls.
I eventually landed a three-month contract job. That rehabilitated my resume and I had no trouble getting callbacks once I had some recent work history. Don’t be above taking a short term gig if you find that the phone isn’t ringing. It might be the thing that turns that around.
I like the failed internet billionaire. It's clever, obviously tongue-in-cheek, and implies one shot for the moon, but landed among the stars.
I recommend against attempts at humor front and center like this on a resume. It’s too early.
I’m in a serious mood trying to solve a serious problem when I’m reviewing resumes. This would fall very flat with me. I would not think you were serious about finding work.
Sneak in some humor later and it might work. If I’m interested enough to read the details of your resume, something humorous later on might get a chuckle out of me.
Now, if in the course of a phone screen, you described yourself as such, you'd probably get a chuckle from me.
Then why are they interviewing? Taking people at face value until you know you shouldn't is an important interpersonal skill. Second guessing what people tell you is pointless. This would be one item in a list of his experience, not what you see first.
I would think it's fun little icebreaker if you are applying for a position making cute iOS games.
However if you are applying for a position developing power-plant control systems it's a bit inappropriate.
The goal should be to build a great product, company and reputation. If that makes you a billionaire, that’s fine. Most likely you will achieve this goal but not the billionaire status.