Angels who forgot their wings: When money alone doesn’t fly

When I raise money for startups, I meet these lost souls far too often — angel investors who forgot their wings. Mostly successful men with wonderful wives, fantastic children (or no wives and no kids) and tragically empty inside.

They feel a void, lack of faith, irritable, restless, craving meaning, finding none. They thought a purposeful life was building wealth and sharing it. Now that they have, they ask, is that all there is?

They write checks to startups and checks to charity. Yet rarely they write a check of time — time to change a life whether it’s an entrepreneur or a homeless child. Even the ones who do, don’t value how meaningful the time they give is worth.

One Texas angel investor told me he craved purpose in his life. I asked if he is involved with charitable causes. He told me for years he’d been on the board of a charity that supports and mentors underprivileged kids. He even led the campaign to build the kids a school.

“That’s great! How many of the kids have you mentored? I’m sure you have great stories.”

“None,” he shamefully admitted. “ I don’t have time.”

I bit my native Texas tongue and didn’t say, “That’s bull shit” instead I said,

“Darling you know, we don’t change the world one dollar at time, we change the world one person at a time.”

Jewish wisdom says whoever saves one life is considered to have saved the world. We need to be reminded of this, especially when we yearn to live with purpose. Or the opposite, we feel our lives are small and what we do doesn’t count. It does.

I embody this philosophy by being a connector. I don’t worry if the connections have a positive outcome, but I welcome the opportunity to make an introduction that can change someone’s life.

My motto is “I got a guy” literally I know a guy or gal for whatever you need. I get hit up for travel advice, Israeli miracle cures, and most often, for meaningful work or the love of your life. I make a lot of romantic and professional matches (never both at the same time). Often it’s solicited, yet sometimes I make a match without being asked (a trait referred to as Chutzpah).

For example, three years ago ‘Samuel’, a handsome 40-something with a chiseled jaw and bright green eyes, came to my office to learn how to be an angel investor. He was Manhattan raised, Columbia MBA, and built and cashed out of his hedge fund. He moved to San Diego to enjoy his riches. I asked him about his life.

“What do you do all day?”

“I play golf and date.”

“That’s it? You should to do something to give back to society.”

Being a Jewish mother, I told him exactly what he should do with his life.

“You should teach. It’s the most honorable and meaningful profession.”

So I introduced him to my colleague who’s an attorney and a part-time professor at San Diego State University Business School. They became friends and Samuel started volunteering, teaching finance. He loved it. Now he teaches four to five classes a semester and is one of the most popular professors in the department. He even invites me to guest lecture on venture capital.

Samuel is genuinely grateful I enriched his life and he’s now able to inspire hundreds of students.

A year and a half later he returned the favor. He recommended I hire his star student Maddie to be my intern. She was fantastic and became an integral part of my San Diego team. Sadly Maddie’s graduating now. At a tearful goodbye last week, she gave me a gift and handed me this letter:

“Dear Audrey,

I am SO grateful to have had the opportunity to work for you at OurCrowd for the past year and a half. There’s never been a boring moment working for Audrey Jacobs.

You have become my mentor and I’ve learned so much from you. You never let anyone stop you from pursuing your dreams and are never afraid of a challenge.

You have taught me to be persistent, fearless, and go after whatever I want in life. You’ve also taught me the importance of community and the power of a strong network.

You go above and beyond for your employees and it’s truly inspiring to have a boss who cares so much. I hope one day to have a career as successful as yours and be able to give my staff as much as you give us.

Keep being your unique, authentic and hilarious self, because the world needs more people like you!!! I’ll be visiting often so you won’t even have a chance to miss me!

Love, Maddie”

My wings were a flutter with joy. Maddie called me her mentor, yet I preferred to be seen as her angel during that pivotal time in her life. But I wasn’t done.

Maddie needs a job and wants to work as an investment advisor. She’s been interviewing, but I don’t like the firms she’s considering. I want her to work with great people that will continue to push and inspire her. So I introduced her to Russell Grossman, a colleague I respect who works for Alliance Berstein. Maddie went after the opportunity with great zeal. Today she called to say she accepted their offer.

Angels who forgot their wings will soar again with purpose when they recognize how valuable the small acts of kindness matter. Today whether someone asks you or not; make an introduction, invite them to an event or meet them in person to reconnect. Our legacy of meaning is the culmination of the meaningful connections we make.


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