A potential client once looked at Nancy A Shenker’s hourly rate and said what some people always say: “That’s a lot.”
Nancy didn’t flinch. She didn’t stare at the ceiling hunting for a smaller number. She just looked the person in the eye and said, essentially, fine — go find less. “Hire somebody with three years of social media experience as opposed to 20 years,” she told me. “
You could buy your shoes at Payless, or you could buy good quality shoes.
Then she added the part that made me sit up: she’d just doubled that rate. At 70.
If you want to know one thing about Nancy, know this — she has been trying to walk out the corporate door since the day she walked in.
“My mother tells me that when I was an infant, I used to kick my covers off. I’ve always been a bit of a rebel.”
Nancy spent the first half of her career in rooms that sound like security itself: Citibank, MasterCard, the rollout of the “Priceless” campaign, then the world of trade shows where Comic-Con was taking off. But she was an English and psychology major who got, in her words, “sucked in because it was the 80s and golden handcuffs were really appealing.” Corporate handed her the weird, impossible projects — “let’s just give it to Nancy” — which was really entrepreneurship wearing a badge.
The break came in a meeting. A colleague made a sexist comment, and everything went Charlie Brown. “All I was hearing was wah, wah, wah, wah.” She knew she had a target on her back, so she did the George Costanza — kept showing up until they handed her a severance package. She left at 48.
What she didn’t expect was how little corporate had actually prepared her. “The hardest, honestly, was starting my own business with no previous entrepreneurial experience, because I thought I knew it all.” Then 2008 hit.
“Speaking of boats — the boat was hit by a torpedo. And I was not prepared for it. But I learned humility. So when COVID hit, I was ready. I had already lived through one torpedo attack.”
That’s what I admire about Nancy. Her story isn’t one clean reinvention. It’s five, maybe seven — a fleet, not a boat. Today she runs The OnSwitch (marketing consulting), does fractional CMO work, writes a serialized memoir on Substack, publishes a newsletter, and builds no-code apps for fun. She calls it a portfolio. I call it a fleet.
The reason Nancy’s story matters for anyone eyeing entrepreneurship at 50, 60, or 70 is that she doesn’t traffic in inspiration. She traffics in specifics. Here’s what she’d actually tell a woman sitting at her kitchen table wondering if she could do this.
Practice saying your price out loud.“You have to role play in front of a mirror,” she says. When someone balks, don’t retreat — reframe. My own version: “This is what it costs to get this result. We could take this off, this off, this off.” You’re not defending a number. You’re describing value, and the tradeoff of someone not going all in.
Your Rolodex is a superpower — use it without an agenda. Nancy’s first big retainer came from a lunch she scheduled with a former colleague just to catch up. She wasn’t pitching. “Golden rule 101 — care about what somebody else is doing.” The client appeared because she’d built the relationship years earlier. “It wasn’t random. You had already built that.”
Hire for what you hate, not for who you like. Nancy knew 23 years ago she was terrible at operations and finance. Her mistake? She hired more people like herself instead. “It’s a business, not a book club.” And don’t expect your ops person to be your happy-hour buddy. “If you vibe too much — terrible idea.”
Know if you’re building a dinghy or a yacht.“Size is a male measure of success,” she says. She sat down with an Excel spreadsheet — the very tool she loathes — and separated “what’s nice versus what’s necessary.” Her goal now isn’t venture scale. It’s enough to fund the next 30 years of a life she actually wants. There’s no shame in that number.
Run toward a vision, not away from a job. Nancy admits her own launch in 2003 was partly an escape. “You’ve got to get your headset in the right space — I’m choosing to do this because I want to,” not because you’re fleeing corporate or can’t land the next gig.
A lot of men start businesses with an eye toward scaling and selling. Many women start businesses with an eye toward adding value to their lives and to the world. There’s a happy medium in there somewhere.
Nancy was an AI pioneer — she wrote her first book about it in 2017, before most people had heard of ChatGPT. She still bristles that “the tech bros are getting credit for this when it was really their grandmother who was the godmother of AI.” She names her AI Beulah and gets most of her paid work done by noon, then spends afternoons on the analog stuff: a paper notebook split into three daily columns — self-care, passions, money projects — and neon index cards.
But she’s clear-eyed about the cost of visibility.
The LinkedIn posts that perform for her aren’t the smart ones. They’re the saloon-girl photo, the shot of her bouncing a robot on her knee in a lime-green apron. “It’s disgusting that I have to use my boobs to get eyeballs. But if that’s how LinkedIn wants to play, I can play that game too.” We live, she says, in a world that’s “youthified and browified,” where young founders get celebrated and the 70-year-old builders — and the intergenerational duos building boats together — get ignored.
And then there’s the mean-girl problem inside the very spaces meant to lift women up. Someone once commented “keep your legs closed” on a photo of Nancy in a bikini. Her response: “I’m 70. At this age I should be able to sit however I want.” She led with humor, refused the rage bait, and started a women’s group she calls the Break Room — Be Real And Kind. “If we hang together, there’s so much more strength in numbers.”
This is the roadmap I keep finding in these interviews: the world has the entrepreneurship story wrong. It says builders are young, male, and venture-backed. Nancy is none of those things, and she’s built more, longer, and with more nerve than most.
“The me that I was at seven years old is the same me I am at 70 — just with more nerve.”
So here’s the question Nancy leaves me with, and I’ll pass it to you: are you running away from something, or building toward a vision? Because one of those makes a much better boat.
👉 Check out the podcast of this interview, and those of the other amazing women that I’ve interviewed to be inspired and to glean ideas and tips from the playbooks they share.
If this landed for you, share it with a woman who’s been eyeing the door. And tell me in the comments — what would you name your boat?
Find Nancy Shenker:
Marketing consulting: theonswitch.com
Personal brand + serialized memoir “Your Nerve”:nancyaf.com
Follow the memoir and her writing on Substack, and on Facebook at her Nancy A. Shenker (Nancy AF) page.
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