It means precisely that -- if you're in your 50s, and have the experience of someone in their 20s, that's a red flag. Good: - You ran a successful business -

It means precisely that -- if you're in your 50s, and have the experience of someone in their 20s, that's a red flag. Good: - You ran a successful business - You managed a division at Google - You were faculty at an elite university - You were a management consultant at an elite firm, and build out a rolodex of elite connections - You had a diverse array of jobs which give you a unique skillset for the startup at hand. For example, if you worked in a hospital, in China, and as an EE, you might be in a unique position to start a medical devices outsourcing firm. Etc. Bad: - Spending 35 years as a SWE at a random company. - A series of random jobs, with no coherence or anything of note (e.g. sales rep, admin, IT, etc.) - ... and so on. "incredibly capable with knowledge, experience and connections that would give them a massive advantage" means you can either get funding from a friend who knows you, or you probably want to find some way to signal that. If you haven't found a way to signal that in 35 years, odds are you won't be able to e.g. signal why someone should partner with you, buy your product, work for you, etc.