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Build Your Own Boat

Build Your Own Boat

Von: Janine Vanderburg
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An entrepreneurship podcast for women in midlife and beyond. What if the most powerful thing you could do right now — for your finances, your freedom, and your future — was to stop waiting for someone else to hand you an opportunity and start building your own? Build Your Own Boat is the podcast for women in midlife and beyond who are done playing by rules that were never written with them in mind. Hosted by award-winning 3x entrepreneur Janine Vanderburg, each episode features real conversations with women in midlife and beyond who made the bold decision to bet on themselves — launching businesses and creative ventures, building wealth, and rewriting what entrepreneurship looks like in the second half of life. This isn't a podcast about hustle culture or overnight success stories. It's a roadmap — built from lived experience, hard-won wisdom, and the kind of honest conversation you rarely hear anywhere else. Guests include founders, consultants, creatives, coaches, media makers, and civic leaders who are proving every week that midlife isn't a ceiling. It's a launchpad. Whether you're just beginning to wonder if entrepreneurship is for you, actively building your business, or simply looking for proof that it's not too late — you'll find it here. Every episode, you'll discover: 1. How real women in midlife launched and grew successful ventures — and what they wish they'd known sooner 2. Practical strategies for building financial independence and freedom on your own terms 3. Honest conversations about the challenges of midlife entrepreneurship, and how to navigate them 4. Inspiration that's grounded in reality, not motivational posters The Encore Economy is booming — and women in midlife are driving it. Build Your Own Boat is where their stories live. Subscribe now and join a growing community of women who are building something that's entirely, unapologetically theirs. And do SUBSCRIBE to Build Your Own Boat on Substack as well, to read the full stories of our guests, and their best tips and resources. https://buildyourownboat.substack.com/© Janine Vanderburg Management & Leadership Ökonomie
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  • How Do You Build Multiple Businesses in Midlife? Nancy Shenker's Portfolio Career Playbook

    How Do You Build Multiple Businesses in Midlife? Nancy Shenker's Portfolio Career Playbook
    Jul 28 2026
    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 —...
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    42 Min.
  • Leaving Chiropractic for Health Coaching in Midlife: Dr. Sam Graber on Rebuilding Your Identity and Your Business

    Leaving Chiropractic for Health Coaching in Midlife: Dr. Sam Graber on Rebuilding Your Identity and Your Business
    Jul 23 2026
    Episode SummaryDr. Sam Graber spent decades as a practicing chiropractor before walking away from disease-focused medicine to build a health and life coaching business from scratch. In this episode of Build Your Own Boat, she explains how burnout, an undiagnosed perimenopause transition, and a growing frustration with insurance-driven "disease management" pushed her to close her practice and start over — without a business plan, a mentor, or a clear name for what she was building. Sam shares the real, unpolished mechanics of that first year: undercharging for her services, encountering predatory business coaches, and slowly discovering that self-knowledge — not a perfect strategy — is the real foundation of a sustainable second-act business. She also unpacks why she now treats the body itself as business infrastructure, explaining how sleep, nutrition, and hormone health directly determine an entrepreneur's capacity to build and sustain a new venture.About the Guest: Dr. Sam GraberDr. Sam Graber spent decades practicing as a chiropractor before leaving the field to build a career in holistic health and life coaching. Frustrated by a conventional medical model built around diagnosis codes and disease management rather than prevention, she closed her brick-and-mortar practice and reinvented herself as a health strategist — helping clients bridge the gap between their doctors and their own bodies. Today, through her "Strong Over Skinny" philosophy, Dr. Sam works primarily with women navigating perimenopause and menopause, coaching them toward stronger bodies, sharper minds, and metabolically sound lifestyles instead of restriction-based diet culture. She offers one-on-one coaching and a membership community, writes regularly on Substack, and also serves as Board Chair of The Starr Institute, a nonprofit dedicated to youth development.Key TakeawaysCareer transitions in midlife are identity transitions, not just business decisions. Leaving a licensed, credentialed profession like chiropractic care means rebuilding not only your income model but also how you introduce yourself to the world.Undercharging is one of the most common first-year mistakes for new coaches and consultants. Without a clear sense of the time, expertise, and transformation being delivered, many women entrepreneurs price their services far below their actual value.Not all business coaches are a good fit — vet them like you would a business partner. Red flags include coaches who ask for large financial commitments without first asking questions about your goals, background, or readiness.Self-knowledge is a prerequisite for sustainable entrepreneurship. Understanding what specifically energizes versus depletes you prevents you from unconsciously rebuilding the same "box" you just left, under a different name.Physical health is business infrastructure, not a personal indulgence. Sleep, nutrition, and hormone balance directly affect an entrepreneur's energy, decision-making, and capacity to sustain a new venture — especially during perimenopause and menopause.FAQHow do you know when it's time to leave a long-term career and start a business?According to Dr. Sam Graber, the signal is often less about a single dramatic event and more about cumulative burnout — a growing sense that the structure of your current work (such as insurance billing requirements in healthcare) no longer aligns with why you entered the field in the first place. She describes reaching a point where the day-to-day demands were "sucking the life and the light" out of her, which became the real catalyst for change.What should you look for when hiring a business coach during a career transition?Look for a coach who asks detailed questions about your background, goals, and readiness before asking for a financial commitment — especially at four- or five-figure price points. Dr. Sam Graber warns that coaches who skip this discovery process, or who treat all clients the same regardless of experience level, are a red flag, particularly for licensed professionals moving from a regulated field into entrepreneurship.Why do many new entrepreneurs undercharge for their services?Many first-time entrepreneurs, especially women, undercharge because they underestimate the time, expertise, and value of what they're delivering, and because of broader cultural conditioning that discourages women from focusing on money. Dr. Sam Graber says she "didn't know what it would even cost" to deliver her services in year one, a common gap for people transitioning from an employed or credentialed role into independent coaching or consulting.How does perimenopause and menopause affect entrepreneurship?Hormonal transitions can affect energy, sleep, mood, and metabolic health — all of which directly impact an entrepreneur's capacity to build and sustain a new business. Dr. Sam Graber notes that many women misattribute these shifts purely to sex hormones, when lifestyle factors like ...
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    38 Min.
  • What Happens When Caregiving Interrupts Your Midlife Business? A Conversation with Wendy Green

    What Happens When Caregiving Interrupts Your Midlife Business? A Conversation with Wendy Green
    Jul 21 2026
    Episode SummaryWhat happens to your business when an aging parent moves in and needs your care? Wendy Green, founder of Hey Boomer and host of the Boomer Banter Podcast, faced exactly this — and instead of powering through, she made a deliberate choice to scale back her podcast and refocus her energy on the work that gives her the most fulfillment for the least burnout. In this episode of Build Your Own Boat, Wendy shares how she built a "fleet" of ventures — coaching, a podcast, a Substack newsletter, group coaching, travel experiences, and in-person classes at continuing care communities — and how she used a simple return-on-investment framework (time, energy, fulfillment, not just money) to decide what to keep, pause, or let go when caregiving for her 96-year-old mother became her new full-time responsibility. This conversation is a candid, practical roadmap for the millions of women who are simultaneously entrepreneurs and family caregivers — a reality the entrepreneurship world rarely discusses honestly.Key TakeawaysCaregiving is a business risk that deserves real planning, not silent sacrifice. According to AARP, the majority of family caregivers are women, many in the same 50+ age range building or running businesses — making caregiving a mainstream entrepreneurial challenge, not an edge case.You don't need every credential before you start. Wendy earned a coaching certification and change leadership credentials, but she stresses that certifications gave her confidence, not permission — waiting for "one more course" is often just delay disguised as preparation.Evaluate ventures using time and fulfillment, not just income. When caregiving demands increased, Wendy assessed each business activity by asking what it gave her versus what it cost her in time and energy, then cut the parts (like heavy podcast promotion) that drained her most for the least return.Solopreneurship is lonely — collaboration fixes it. Wendy co-founded the Age-Wise Collective, a peer-support network of 12+ women podcasters over 50 who cross-promote, share resources, and problem-solve together instead of competing.Reinvention isn't always about starting over — sometimes it's rediscovery. Wendy is shifting her focus from building new things to rediscovering past skills and interests, describing her next phase as "rediscover and redefine" rather than reinvent.Protecting your mindset matters as much as protecting your schedule. While caregiving for a mother who says "96 is enough," Wendy holds onto her own age-positive beliefs by journaling daily, noticing small wins, and staying connected to people and work that make her feel useful.About This EpisodeIn this episode of Build Your Own Boat, host Janine Vanderburg talks with Wendy Green, a certified professional coach and founder of Hey Boomer, about the entrepreneurial journey most business podcasts skip: what happens when you have to recalibrate your growing venture because a parent needs your care. Wendy walks through her path from a computer science career and corporate training roles into coaching, podcasting, and teaching — and then candidly describes putting her podcast on hiatus to prioritize caregiving for her 96-year-old mother, while still finding ways to stay financially and personally engaged through in-person classes and writing. The conversation covers building multiple income streams ("a fleet of boats"), avoiding the trap of over-preparing before launching a venture, using a peer support network to combat entrepreneurial loneliness, and a practical, three-part framework for deciding what stays and what goes when life happens.About the Guest: Wendy GreenWendy Green is a certified professional coach, speaker, and founder of Hey Boomer, a platform dedicated to helping adults navigate the second half of life with purpose and confidence. She hosts the Boomer Banter Podcast, a long-running show (270+ episodes) that has become a go-to resource for people exploring aging, transition, and reinvention after 50. Wendy holds change leadership credentials from Georgetown University and a professional coaching certification, which she draws on in her one-on-one coaching practice, her monthly Banter Circle group coaching community, and in-person classes she now teaches at continuing care communities near her home in Greenville, South Carolina. She also writes Thriving Through Time, a Substack newsletter exploring caregiving, personal growth, and life balance, and co-founded the Age-Wise Collective, a peer network of women podcasters over 50. Wendy is currently caregiving for her 96-year-old mother while continuing to coach, teach, and write — a real-time example of the recalibration she now speaks openly about.Frequently Asked QuestionsHow do you balance running a business with caregiving for an aging parent?Wendy Green recommends evaluating every business activity by what it gives you versus what it costs you in time and energy, then scaling back or pausing ...
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    39 Min.
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