I heard about a retired guy named Sam in his late 60’s who joined a b2b Saas startup in the manufacturing space. It was a traditional industry and they needed a traditional guy. They brought him on as a sales guy, and he was able to bring on old connections from his “rolodex.” He crushed it.

A first they were hesitant to bring him on for several reasons. He was 3x older than the average employee, so they feared there would be communications gaps.

There were.

Sam would make racist and lame jokes amongst colleagues.

“What do you call a Mexican baptism?

…Bean dip!”

These jokes didn’t jive well with the PC-police…but clients loved him. The “sales team” was in the office typing emails while Sam was out meeting people and building relationships.

Another issue. The sales team has to use their CRM system after every meeting to input meeting notes and track client information — they were meticulous. It was all about ‘data.’ But Sam didn’t even know how to use a computer. He didn’t give sh*t about the nerds and their data. He had a knack for sales and that’s all that mattered.

He closed more deals than anyone and individually brought in more business than the entire sales team combined.

“Sam, you’re the man!” they finally started saying.

They say never compromise on culture. Yes, to some degree, that’s true. However, it’s also possible that you might actually learn something from other people who may not “fit” your culture and that you see as different. Maybe they can add value in different ways.

When he interviewed he addressed the elephant(s) in the room.

“Look, I know I’m older than your average employee here. I’m not going to fit perfectly, and heck, I type 5 words per minute.”

The interviewer broke a smile, refreshed by the honesty and humor. Sam then came up with a solution to make it worth their while.

“But if we can get past that, I think I can really help. I can get you a contract with company x, y and z. I don’t even need a big title or a team, just call me sales guy. Hire me for a few months and if it doesn’t work out, then no hard feelings.”

They didn’t give Sam a full time job but hired him on a 6 month contract. It would give him a chance to prove himself. The startup took a risk and it paid off.


If you’re older than the average startup employee but interested in a startup, not all hope is lost.

Find a startup where you can truly add value and show them how you can. Admit your shortcomings and address the elephant in the room. Lower your expectations for pay and title. Tell them you’re willing to take a risk if they are.

If they still don’t get it, go lower. Ask if you can be an unpaid intern. Or a driver. That’ll get their attention. You gotta start somewhere, anywhere!

P.S. Go watch The Intern where Robert Deniro plays the old guy in the startup who is a chauffeur for a pretentious and unexperienced startup CEO (Anne Hathaway), all the while gently giving her advice and pulling the strings in the background.

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