How Do You Build Multiple Businesses in Midlife? Nancy Shenker's Portfolio Career Playbook

Episode SummaryNancy Shenker left a 20-year corporate marketing career at Citibank and MasterCard at age 48 and, over the next two decades, built not one but a fleet of ventures — a marketing consultancy called The OnSwitch, fractional CMO work, a serialized Substack memoir, and an AI-focused newsletter. In this episode, she explains how women over 50 can price their expertise with confidence, land their first clients by mining relationships they already have, and use AI as a daily thinking partner without losing their own voice. She also tackles the harder conversations: ageism and sexism inside LinkedIn's algorithm, "mean girl" dynamics in women's professional spaces, and why "enough" money — not venture-scale growth — is often the smarter financial goal for entrepreneurs starting later in life.Key TakeawaysYour existing network is your first client pipeline. Nancy landed her first major retainer client not through cold outreach, but by reconnecting over lunch with someone from her corporate past and simply asking what they were working on — no pitch required.Price according to value, not insecurity. Nancy doubled her hourly rate at age 70 and recommends role-playing pricing conversations out loud until stating your rate feels natural, comparing it to what accountants or lawyers charge.Hire for your weaknesses, not your comfort. One of Nancy's biggest early regrets was not hiring for operations and finance sooner; she warns against hiring people you simply enjoy hanging out with over people who complement your actual skill gaps."Enough" is a legitimate financial goal. Rather than chasing venture-scale growth, Nancy built a detailed budget separating "nice to have" from "need to have," and checks in quarterly with a financial advisor to fund a lifestyle — not a valuation.AI works best as a structured daily collaborator. Nancy uses an AI tool (which she nicknamed "Beulah") alongside analog systems — a paper notebook divided into self-care, passions, and money projects — to get her work done most mornings by noon.About the Guest: Nancy ShenkerNancy Shenker spent the first half of her career in corporate marketing at Citibank and MasterCard, where she worked on the rollout of the Priceless campaign, before moving into the events and exhibitions world at Reed Exhibitions (where Comic-Con emerged). At 48, she left corporate life to found her own marketing consultancy, The OnSwitch, which she has run for more than two decades under the tagline "bright and timeless."Today Nancy operates a portfolio of ventures rather than a single business: she consults through The OnSwitch, takes on fractional CMO engagements, writes a serialized memoir and self-help graphic novel on Substack, publishes a newsletter called Bodies and Bots, builds no-code apps, and is launching a new business with a 39-year-old business partner. She rebranded her personal identity as "Nancy AF" (nancyaf.com) at 70. Nancy was an early AI adopter, publishing a book on artificial intelligence back in 2017, and she recently founded a women's community called The Break Room, built around the principle of “being real and kind."FAQHow do I find my first clients when starting a consulting business?Start by reconnecting with people from your previous career — not to pitch them, but to catch up and genuinely ask what they're working on. Nancy Shenker landed her first significant retainer client this way: a former colleague she met for lunch ended up asking her to help write a strategic plan, with no sales pitch involved.How should I price my services as a new entrepreneur, especially as a woman?Set your rate based on the value you provide, not your comfort level saying it out loud. Practice stating your hourly rate in the mirror or with a friend until it feels natural, and be ready to respond calmly when a prospect says it's too much — offer to scale back scope rather than dropping your price.When should I hire help in my business versus doing everything myself?Be honest about which tasks you're genuinely bad at — for Nancy Shenker, that was operations and finance — and hire for those gaps early, even before you hire for roles that feel more comfortable or fun. Avoid hiring people simply because you like them personally; prioritize complementary skills over personal chemistry.Do I need to aim for venture-scale growth to be a successful entrepreneur in midlife?No. Many entrepreneurs, especially those starting later in life, are well served by defining "enough" — a number that covers their desired lifestyle and supplements retirement income — rather than chasing rapid scaling or a big exit. Building a detailed personal budget and separating "nice to have" from "need to have" expenses helps clarify that number.How can older entrepreneurs use AI effectively in their business?Treat AI as a daily thinking partner for structuring your workload — for example, asking it to help organize multiple projects into a clear framework — while still using analog tools like notebooks or index cards to track priorities and boundaries. Time-blocking and setting hard stops each day helps prevent AI-assisted work from expanding indefinitely.Has ageism affected visibility for older entrepreneurs on platforms like LinkedIn?Yes. Nancy Shenker has observed through her own analytics that posts referencing her age or more provocative imagery consistently outperform posts she considers more substantive, reflecting a broader cultural bias toward youth. She addresses this by leaning into humor and authenticity rather than avoiding the topic.Resource StackThe OnSwitch — Nancy Shenker's marketing consultancy: https://www.theonswitch.comNancyAF — Nancy Shenker's personal brand site and home for her memoir updates: https://www.nancyaf.comYour Nerve — Nancy Shenker's serialized memoir/self-help graphic novel on Substack The Break Room — Nancy Shenker's women's community, built around the principle of "be real and kind"Build Your Own Boat podcast, hosted by Janine VanderburgWhere to Find Nancy ShenkerWebsite (The OnSwitch): https://www.theonswitch.comPersonal brand website (Nancy AF): https://www.nancyaf.comSubstack memoir, Your Nerve: available via nancyaf.comFacebook: Nancy A. Shenker / Nancy AF pageAbout Build Your Own BoatBuild Your Own Boat is a podcast series hosted by Janine Vanderburg — award-winning three-time entrepreneur and anti-ageism advocate — featuring women who have launched new entrepreneurial ventures in midlife and beyond. The series is part of a larger storytelling project that includes a Substack publication and a forthcoming book, all built around one goal: changing the narrative about who entrepreneurs are and making women in midlife and beyond visible as builders of wealth, freedom, and possibility.