Possible Options for a 55 Yr old (Not me, my buddies dad)

This is a super cool story and profile, the guy sounds like a legend. For someone with his array of experience and likely wide network, I would say he should look into wealth management. I'm sure he has some really strong connections that he could leverage into a solid book of business. He likely would be able to remain in the city he's currently in and would be able to get back out in the field while retaining good flexibility. Not sure how he'd feel about a sales position, but if he worked at startups and co-founded a company, it sounds like he has a knack for sales/networking. Keep us updated with any more correspondence you guys have, I'm interested to hear what he decides on.

He should consider running his own Consulting shop. That kind of resume would get him some hard looks.

Yeah I agree with the comment above. At this point you can't really 'apply' to jobs, you have to wait for people to contact you or set up your own shop.

The Stanford MBA alumni network will be highly valuable for him.

Maybe he should be reaching out to his Stanford network and not a bunch of kids.

If this post is serious - I doubt anyone on here has a clue what a 58 year old should do who wants to ride out of retirement on a white horse and find another pot of gold under the rainbow.

If he's really spend the past 15 years either retired, semi-retired or at a string of failed startups with no exits, he'd best hit that Stanford network hard and hope he's kept in touch. Usually these guys who crushed life in the 80's/90's and haven't accomplished much since, then suddenly are on the job market looking for the same type of prestige role they had back in the 80's 90's, are either one of two things:

Almost out of money because they burned cash on their startups/other endeavors, or overspent, or traded poorly, and don't want to change their spending to keep up appearances - or - They woke up one day to an aging wife, kids off with exciting lives or a drug habit, a house that feels smaller every year, and suddenly they want to relive their glory days

I don't know your dad's friend's situation and maybe he is an exception to the rule. But it's probably safe to assume he's already tapped his personal network. So if he is talking to his friend's son about job prospects, instead of executive recruiters, that's probably a good indicator as to how his life is going.

54 yr old here. Know several people that "look" just like him. They don't need monthly cash flow, (i.e. a job). They want to be intellectually challenged, work on some cool projects, make a difference. One former colleague comes to mind. He's 70 now but has been in this mode for many years. He networks and puts deals together, sometimes getting a deal fee, sometimes a piece of revenue, sometimes both. Most are potential home run type scenarios. Most don't make it. But he has a blast in the creative process of learning the business, putting people together, working through the details, etc. His current project has been quite lucrative, especially for part time work. It took 18 months to get off the ground but now is operating and generating consistent monthly cash flow (well in to 6 figures annualized).

It keeps him "young", interesting, and interested! Also very flexible so he can get off the grid whenever he wants. He does that frequently. Travels to Europe for a month, heads up to the city for a few weeks (loves going to the museums and all that Manhattan has to offer - used to live there).

It's a cool way to live. Starting to move in that direction myself.

That is a pretty badass resume. If he is indeed Philly-based feel free to shoot me a PM and I can try to brainstorm some ideas in the area.

Entrepreneurship could be a good idea. Another would to be to reiterate the wealth management track or working at a broker dealer. Make sure the B/D would be legit though. There are lots of cool ones that work with smaller companies to bring them public and raise money through retail and institutional investors. Getting to know the company inside and out then selling to accredited investors is intellectually stimulating and can be lucrative - especially with a good network!

How do I know you are either A. insane, or B. a liar? Cause you listed Charlotte as a T2 city. My man I would call that a T9 city, just a step above Livingston TX

^^^ Don't talk shit about Livingston, the locusts there are great this time of year. Plus, the concessions stand sold BBQ'd turkey legs during baseball tournaments. Nothing like a big ass turkey leg between games.

Also OP, with this guy's experience, I'm sure he could start doing some angel investing/start up advising. He could scale his involvement up or down with his desired hours, while remaining self-employed.

Has your friend's father considered doing a search fund (entrepreneurship through acquisition)?

Think of it as a micro private equity fund. Traditionally, it's a financing vehicle to provide capital to a entrepreneur looking to buy an existing small to medium private business. The idea is you raise money from investors and have 24 months to find a small or medium with stable free cash flows but plenty of room for growth with a new CEO, new strategy, operational improvements, etc. Put in at least 10% equity and finance the rest with debt.

Search funds are popular with MBA students and people with a few years of experience, so your friend's father will have an advantage in the search process since he has more experience (deal making and operating skills) and owners of small businesses, rightly or wrongly, feel more comfortable handing the reins over to a guy who has been around the block as opposed to a freshly-minted MBA. Moreover, assuming he has plenty of money in the bank, he can do a self-funded search and raise equity from investors once he has a deal under LOI (typically better economics for the entrepreneur)