Build Your Own Boat

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/

Build Your Own Boat is a business podcast hosted by Unknown Host, with 34 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Build Your Own Boat, a business show with 34 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #33

  How Do You Turn Relational Courage Into an Unfair Advantage? Hatton Littman on Redesigning Your Career After 50

  Aug 13, 202651 min

  Episode Summary This episode answers a question many accomplished women ask at midlife: how do you leave a stable, high-impact career and build a consulting business that actually fits the life you want? Hatton Littman, founder of Surf HL, left a 25-year career in education, government, and nonprofit leadership to launch her own leadership development and strategic communications firm in Montana — and six years later, she's grown revenue tenfold, learned to price on value instead of guilt, and deliberately engineered a lower-revenue year to protect her health and freedom. She names "relational courage" as her unfair advantage: the willingness to have hard conversations, fire a client when the outcomes aren't there, and tell the truth even when it costs her short-term comfort. This episode gives a practical, numbers-based roadmap for women considering entrepreneurship after 50 — covering pricing psychology, energy management as an introvert-leaning extrovert, and how to spot paradigm-shift opportunities using tools like AI. Key Takeaways Relational courage is a defensible business asset. Hatton Littman defines it as the willingness to name hard truths, have uncomfortable conversations, and act on them — including firing a client mid-contract when she couldn't deliver the promised outcome, because protecting her integrity mattered more than the revenue. A lower-revenue year can still be a successful year. At age 50, Hatton deliberately planned to reduce her workload; gross revenue fell 43%, but net profit margin only dropped 25%, and she used the freed-up time for travel and rest — proof that revenue targets and life goals need to be integrated, not separated. Value-based pricing beats hourly billing for long-term growth. Instead of pricing by time spent, Hatton tracks client outcomes annually (e.g., helping win $32.2 million in public school funding) and uses those documented results to justify raising her rates and quiet the internal voice that resists charging more. Energy management matters as much as skill. As Hatton has aged, her introversion has strengthened even though extroverted facilitation work is her biggest revenue driver; she's now shifting toward roughly 30% "desk work" — deep analysis and one-on-one projects — and using AI as an executive-assistant tool for synthesizing qualitative data, rather than replacing the relational work only a human can do. Paradigm shifts create opportunity, not just disruption. Drawing on her philosophy of science background (Thomas Kuhn's theory of scientific revolutions), Hatton argues that periods of chaos and uncertainty — like today's AI-driven shift — open new markets for people who can build relational trust on teams and help organizations navigate change together. Guest Bio: About Hatton Littman Hatton Littman is the founder of Surf HL , a Montana-based consulting firm specializing in leadership development, expert facilitation, and strategic communications. She works with nonprofits, school districts, government agencies, and businesses navigating complex change and teams that need to collaborate under pressure. Before launching Surf HL, Hatton spent more than 25 years in education, government, and nonprofit leadership — including nearly a decade as director of technology and communications for Missoula County Public Schools, where she helped pass $158 million in public funding bonds and built a 21-mile fiber network that reshaped the city's infrastructure. She holds a degree in philosophy, with a focus on philosophy of science, and is a graduate of the Leadership Montana program. Now in her sixth year running Surf HL, Hatton has grown her business tenfold, contributed to the forthcoming book Compass and Chaos, and is developing a new body of work on building and honoring personal power inside organizations. Episode Overview Janine Vanderburg sits down with longtime friend and former colleague Hatton Littman to trace her path from a decades-long career in public education and government to founding her own leadership consulting firm, Surf HL, in the middle of the 2020 pandemic. They dig into the exact moment Hatton knew it was time to leave her director-level role, the trusted circle of women (and her husband) who helped her make the leap, and the "anchor client" strategy that turned a side hustle into a real business. The conversation moves into pricing — including why so many women avoid talking about money and how Hatton learned to argue back against her own rate-increase anxiety using documented client outcomes. Later, they explore Hatton's decision to deliberately shrink her revenue at age 50 to protect her time and energy, her discovery that her introversion has intensified with age even though extroverted facilitation is her top revenue source, and how she's using AI as a thinking partner for qualitative analysis rather than a replacement for relational work. The episode closes with a discussion of paradigm shifts — grounded in Hatton's philosophy of science background — and where she sees the biggest opportunities opening for new entrepreneurs right now. FAQ What is "relational courage" and why does Hatton Littman call it an unfair advantage? Relational courage is the willingness to have honest, sometimes difficult conversations in professional relationships — stating your needs clearly, naming conflict directly, and delivering hard truths to clients or teams even when it's uncomfortable. Hatton considers it her unfair advantage because it's a human skill that can't be replicated by AI or easily copied by competitors, and it directly built her credibility with long-term clients. Why did Hatton Littman plan for a lower-revenue year in her business? At age 50, Hatton deliberately reduced her workload to about 75% of full capacity to prioritize travel, rest, and professional development instead of chasing maximum revenue growth. Her gross revenue dropped 43%, but her net profit margin only fell 25%, showing that a strategic pullback doesn't have to mean financial failure — and the following year she rebounded with a tenfold increase in contract opportunities compared to her first year in business. How does value-based pricing work for consultants and solopreneurs? Value-based pricing means setting fees based on the outcomes and impact delivered to the client rather than hours worked. Hatton tracks measurable results for every client engagement — such as helping secure $32.2 million in public school funding — and uses that documented evidence both to justify rate increases and to overcome her own internal resistance to charging more. How can entrepreneurs use AI without losing the human relational element of their work? Hatton uses AI as an "executive assistant" for tasks like summarizing large bodies of qualitative interview data or generating professional-looking charts quickly — freeing up her energy for the in-person facilitation and conflict-navigation work that AI cannot replicate. She positions relational courage and live human trust-building as the differentiators AI can't replace. What opportunities does Hatton Littman see opening up during the current AI-driven paradigm shift? Drawing on her philosophy of science background, Hatton points to growing demand for people who can help teams navigate uncertainty with trust, work addressing cultural and civic polarization, and innovation at the intersection of AI efficiency and human connection. She also recommends following futurist Amy We...

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  Episode #32

  How Do You Build a Writing and Speaking Career in Midlife? Maria Leonard Olsen on Side Gigs, a Shocking DNA Discovery, and 50 After 50

  Aug 11, 202637 min

  Episode Summary Attorney and author Maria Leonard Olsen shows how women can build a fulfilling second career — as a writer, speaker, and podcaster — without giving up the financial security of their primary profession. After becoming a lawyer to please her immigrant mother, Olsen used the "side boat" of writing during a career break to eventually publish eight books, deliver two TEDx talks, host the podcast Becoming Your Best Version, and appear on CBS Sunday Morning, all while continuing to practice law full-time. The episode also covers a life-altering twist: a consumer DNA test revealed that the man who raised her was not her biological father, a discovery that became the subject of her upcoming book, Before and After the DNA Test. Listeners get a real, step-by-step roadmap — writing articles to build credibility, applying repeatedly for TEDx talks, posting daily on social media, and learning to say no — for turning a side project into a legacy-building second act. Key Takeaways You don't have to quit your day job to build something new. Olsen kept her law practice as a financial safety net while building her writing, speaking, and podcasting career on the side — proving a "side boat" and a primary career can coexist. Credibility is built in layers: articles first, then books, then stages. Olsen advises aspiring authors to write articles and build a "clip file" before pitching a book, because publishers and speaking bureaus want proof that others have already paid for your work. Consistent, low-effort visibility compounds over time. Daily posting on LinkedIn (which cross-posts to Facebook, X, and Threads) built the following and credibility that eventually led to a CBS Sunday Morning feature — after a producer found her simply by searching "bucket lists." Misattributed parentage from consumer DNA tests is more common than people think. Olsen's own 23andMe result revealed her father was not her biological parent, a discovery so disruptive that she spent a year researching it, wrote a book about it, and now warns others about the emotional and legal consequences of home DNA testing. Saying no to others is often saying yes to yourself. Escaping a lifelong pattern of people-pleasing — by asking "Do I really want to do this, or am I just trying to please someone?" — freed Olsen to focus her time on what actually aligns with her goals. Guest Bio: Who Is Maria Leonard Olsen? Maria Leonard Olsen is a practicing attorney in Washington, D.C., an author of eight books, and a two-time TEDx speaker. Her most popular book, 50 After 50: Reframing the Next Chapter of Your Life, chronicles the 50 new things she tried during her 50th year following divorce, sobriety, and becoming an empty nester — and became the basis for her TEDx talk, "Turning Life's Challenges Into a Force for Good." A graduate of Boston College and the University of Virginia School of Law, Olsen served in the Clinton administration's Justice Department before building a career in civil litigation. She hosts the award-winning podcast Becoming Your Best Version, where she has interviewed more than 300 guests about personal growth and reinvention. Her story has been featured on CBS Sunday Morning, and she writes for outlets including AARP's The Ethel. Her forthcoming book, Before and After the DNA Test, explores the emotional and legal fallout of misattributed parentage — a subject she researched after a consumer DNA test revealed her own father was not her biological parent. Frequently Asked Questions How can I start a side career while keeping my full-time job? Start small and build proof of your work over time. Maria Leonard Olsen recommends writing articles first to build a "clip file," then using that credibility to pursue books, speaking engagements, and other opportunities — all while your primary job continues to provide financial stability. How do you get a TEDx talk? Getting a TEDx talk typically requires persistence and a track record. Olsen submitted twelve applications before she was accepted, and recommends building a platform and publication history first, since TEDx organizers vet speakers and often require coaching before the event. What are the risks of taking a consumer DNA test like 23andMe? Consumer DNA tests can reveal misattributed parentage, meaning the person who raised you is not your biological parent — a discovery Olsen experienced firsthand. She warns that these tests, often marketed as fun holiday gifts, can uncover unexpected family secrets with significant emotional and legal consequences, which is why she wrote Before and After the DNA Test. How do you stop being a people pleaser? Olsen suggests pausing before saying yes to any request and asking two questions: "Am I doing this because I want to, or just to please someone?" and "Does this bring me closer to who I want to be?" If the answer is no, she recommends politely declining without over-explaining, recognizing that saying no to others is often saying yes to yourself. Can you make money from writing books, speaking, and podcasting? It's possible, but Olsen describes it as slow going unless you're a skilled marketer. Speaking engagements at corporations can be lucrative, while books tend to build credibility and open other opportunities rather than generate direct income. She recommends keeping a primary source of income while building a following through consistent content and public speaking. Resource Stack 50 After 50: Reframing the Next Chapter of Your Life by Maria Leonard Olsen Maria Leonard Olsen's official website (books, TEDx talks, speaking inquiries) — marialeonardolsen.com TEDx Talk: "Turning Life's Challenges Into a Force for Good" — available via her website Becoming Your Best Version podcast — Apple Podcasts | Spotify 23andMe DNA testing service (referenced in the discussion of misattributed parentage) — 23andme.com Where to Find Maria Leonard Olsen Website: marialeonardolsen.com Instagram: @fiftyafter50 Facebook: @FiftyAfter50 Podcast, Becoming Your Best Version: Apple Podcasts | Spotify Book: 50 After 50: Reframing the Next Chapter of Your Life — available on Amazon Forthcoming book: Before and After the DNA Test — available for pre-order via her website About Build Your Own Boat Build 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 ar...

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  Episode #30

  What's Your "Unfair Advantage"? Jennifer Stapleton on Turning 20 Years of Nonprofit Connections Into Fire and Bliss

  Aug 4, 202638 min

  Episode Summary Jennifer Stapleton left a senior communications executive role at a national nonprofit at 46 to launch Fire and Bliss, a consulting firm that now helps foundations and well-funded nonprofits with crisis communications and fundraising strategy. This episode answers a question every experienced professional should ask before going out on their own: what is your "unfair advantage" — the accumulation of experience, insight, and connections that no one else can easily copy, replicate, or purchase on the open market? Stapleton explains how two decades of nonprofit and philanthropic relationships became the foundation of her business, why she launched without a website, why deliberation without action never produces clarity, and how she navigated the "messy middle" between early friend-referred clients and a sustainable, sellable business. She also shares candid numbers on pricing mistakes, losing money in year one, and why women should charge at least twice what they think they should charge. Guest Bio Jennifer Stapleton is the founder of Fire and Bliss , a communications and fundraising strategy consultancy serving foundations and well-funded nonprofits. Before starting her business, she spent nearly two decades in nonprofit and philanthropic communications, holding senior executive roles at organizations including Pew, Freedom House, and Bread for the World. After reaching the top of the traditional nonprofit communications ladder and finding it unfulfilling, she left her executive role in the wake of January 6th and the pandemic, relocated from Washington, D.C. to Colorado, and built Fire and Bliss from a mountain-cabin meditation session into a six-year-old firm specializing in crisis communications planning and fundraising consulting for the nonprofit sector. Key Takeaways Your unfair advantage is the experience, insight, and connections no one else can easily copy, replicate, or buy. Stapleton didn't set out to build Fire and Bliss around her network — but roughly 90% of her business over six years has come from friends or friends of friends built during two decades in nonprofit and philanthropic communications. You don't need a website, brand, or logo to start a consulting business — you need a name, a clear offer, and a list of people to tell. Stapleton launched Fire and Bliss on word-of-mouth alone and didn't build a website until roughly 18 months in. Deliberation doesn't create clarity — action does. Borrowing a metaphor from business mentor Chuck Blakeman, Stapleton compares starting a business to sailing without a map: you move, hit obstacles, adjust course, and that's how clarity is built, not by planning from the shore. Price at least double what you're thinking, and expect trial and error. Stapleton lost money in year one, broke even in year two, and didn't feel financially solid until year three; she now recommends a project-based (not hourly) pricing model for clarity with clients. There is no "messy middle" shortcut — you have to learn business development. After the early wave of friend-referred clients dries up, sustainable growth requires deliberately investing in yourself through cohorts, mentors, and peer business communities rather than working in isolation. FAQ What is an "unfair advantage" in business? An unfair advantage is the combination of experience, insight, and connections a person accumulates over their career that no one else can easily copy, replicate, or purchase on the open market. It's not a negative or anti-competitive concept — it's the unique foundation someone already has for starting a business, often without realizing it. Jennifer Stapleton's unfair advantage was two decades of relationships built across nonprofit and philanthropic communications, which became the primary source of clients for Fire and Bliss. Do I need a website to start a consulting business? No. Jennifer Stapleton launched Fire and Bliss using only email and word-of-mouth outreach to her existing professional network, and didn't build a website until about a year and a half after starting the business. A website, logo, and brand are refinements that can come later — what you need first is a clear offer and people to tell about it. How much should I charge when starting a consulting business? Stapleton recommends charging at least twice what you initially think you should charge. She underpriced her services in year one, lost money, and had to revise her pricing strategy multiple times before settling on project-based pricing, which gives both the consultant and client clarity on deliverables instead of debating hourly rates. What is the "messy middle" in starting a consulting business? The messy middle is the stage after the early rush of clients from friends and existing contacts dries up, but before a consultant has developed real business development skills. Many new consultants get through their first one to two years easily on referrals, then stall because they don't yet know how to generate new business systematically. Is it risky to leave a stable job to start a business in midlife? Stapleton argues that in-house jobs offer a false sense of security — salaries, benefits, and titles can disappear overnight through layoffs, grant cuts, or reorganizations. Starting a consulting business does require learning new skills, but it isn't inherently less secure than staying employed. Resource Stack Fire and Bliss (Jennifer Stapleton's communications and fundraising consultancy): fireandbliss.com Chuck Blakeman — business mentor whose "boat without a map" philosophy (action drives clarity, not deliberation) is referenced in the episode Kami Gildner — business network/cohort connection referenced as a source of peer learning and community for entrepreneurs Fire and Bliss free advice newsletter — sign up via the "Free Advice" button at the bottom of fireandbliss.com Build Your Own Boat Substack — full written profile of Jennifer Stapleton's story, part of the broader Build Your Own Boat storytelling project Where to Find Jennifer Stapleton Website: fireandbliss.com LinkedIn: https://www.linkedin.com/in/jenniferbcstapleton/ Free Advice newsletter: Sign up at the bottom of fireandbliss.com About Build Your Own Boat Build 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.

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  Episode #29

  How Do You Fund a Business After 50 Without Venture Capital? AnnMaria De Mars on Bootstrapping 7 Generation Games

  Jul 30, 202637 min

  Episode Summary Most women over 50 who want to start a business don't have angel investors lining up — and AnnMaria De Mars, founder of 7 Generation Games, didn't either. In this episode of Build Your Own Boat, De Mars explains exactly how she funded her math-and-culture-based educational game company without a single six-figure investor check: SBIR federal research grants, three Kickstarter campaigns, two seed rounds through startup accelerators, crowd equity raises, and dozens of friends who each invested $5,000 to $20,000. A world judo champion turned statistician, professor, and programmer, De Mars founded 7 Generation Games at 57 and shows why perseverance, deep community relationships, and a willingness to "do hard things" — lessons she learned competing internationally in judo — are the real predictors of entrepreneurial success in midlife, not access to venture capital. Guest Bio AnnMaria De Mars is a technology executive, statistician, author, and the first American to win a gold medal at the World Judo Championships (1984, -56kg). She holds a Ph.D. from the University of California, Riverside, and has built a career spanning industrial engineering, university statistics teaching, and software development. She has founded four companies, including Spirit Lake Consulting and The Julia Group, and is the co-founder and president of 7 Generation Games , an educational technology company she launched at age 57 that builds cross-curricular math games rooted in Latino, Indigenous, and U.S. history storylines. Her latest venture, 7 Gen Blocks , is a no-code educational game builder — "WordPress for educational games" — that lets anyone build a custom learning game without programming knowledge. De Mars has been named one of Forbes' 40 Women to Watch Over 40, is an AARP Purpose Prize Fellow, and was the first woman to serve as president of a national judo organization. She is also known as the mother of Olympic judo bronze medalist and former UFC champion Ronda Rousey, and of sports journalist María Burns Ortiz, who co-founded 7 Generation Games alongside her. Key Takeaways Non-dilutive funding, like SBIR grants, is often the best money a startup can get. Unlike venture capital, small business innovation research grants don't require giving up equity, yet many founders overlook them because they don't carry the same prestige as a seed round. Perseverance built through years of high-stakes competition transfers directly to entrepreneurship. De Mars credits 14 years of international judo competition with teaching her that success takes years, not months, and that setbacks along the way are normal, not signs of failure. Starting a company as a side hustle while keeping a paying job reduces risk during the leanest years. De Mars recommends bootstrapping, working without pay when needed, and scaling back lifestyle costs rather than waiting for outside investment to arrive. Older founders have a funding advantage most people overlook: a wider network of financially stable friends. Instead of waiting for one investor to write a six-figure check, De Mars raised her first seed round from a large group of friends who each contributed $5,000–$20,000. Relationships built over decades — not just age itself — open doors in education and rural communities. In many Indigenous communities in particular, De Mars found that gray hair signals authority and trustworthiness rather than irrelevance, and long-standing local relationships made it possible to get schools to test her products. Owning your own code, rather than building on top of a third-party AI platform, protects a startup from unpredictable price hikes. 7 Generation Games uses AI tools like Gemini and Adobe Firefly to assist with content creation but keeps its core game-building technology proprietary so pricing and product control stay in-house. Episode Notes AnnMaria De Mars has lived what looks on paper like five separate careers — industrial engineer, world champion judoka, math professor, statistician, and software developer — but she describes them all as variations on the same skill set: math, probability, and programming. The exception, she says with a laugh, is judo, though even there she approached competition by studying probability and looking for underused strategies rather than "the prettiest" way to win. She and Janine dig into what 14 years of elite judo competition — in a sport where, as De Mars puts it, "people can legally knock you down, choke you unconscious, and break your arm" — taught her about building a business later in life. The biggest lesson: perseverance. Success isn't a straight line, and the willingness to "do hard things" repeatedly, for a long time, is what actually separates successful founders from everyone else. De Mars founded 7 Generation Games at 57, growing it out of Spirit Lake Consulting, a firm she co-founded on the Spirit Lake Nation in North Dakota. The company makes math-teaching games woven into Latino, Indigenous, and U.S. history storylines, aimed at helping students — particularly those in grades three through eight — avoid falling behind in math before they even realize it's closing doors to careers like engineering, architecture, or medicine. The conversation turns candid around funding. De Mars walks through every method she used to finance the company since traditional investors weren't interested in an idea "scratched on a napkin" from a founder who, in her words, doesn't "look like Mark Zuckerberg." That included multiple SBIR (Small Business Innovation Research) grant phases, three Kickstarter campaigns, two accelerator-based seed rounds (through an ed-tech accelerator in Salt Lake City and Start-Up Chile), crowd equity raises, and — critically — a large group of friends who each invested smaller amounts. She makes the case that being older is actually a fundraising advantage: by your 50s, you likely know people in stable careers who can afford to invest a few thousand dollars, even if no one is writing six-figure checks. De Mars also traces 7 Generation Games' customer pivots: from selling directly to parents, to school and district bulk sales, to its current model of custom game development for tribal nations, nonprofits, and federal agencies, and now to 7 Gen Blocks — a no-code platform anyone can use to build their own educational game, similar to building a blog on WordPress. The episode closes on two important threads: how age and long-standing community relationships have functioned as an asset rather than a liability in her work with Indigenous communities and rural schools, and why — despite building an "AI-integrated" product — De Mars and her team ultimately chose to own their proprietary code rather than build their platform on top of a third-party AI service, after watching what happens to businesses that lose control when a platform they depend on changes its pricing or rules. She closes with direct advice for the woman in her 50s who is done with the corporate job search and considering starting something of her own: build it on the side while you still have income, get comfortable operating on much less money than you think you need, and delay hiring until it's genuinely painful not to. FAQ How did AnnMaria De Mars fund 7 Generation Games without venture capital? She combined multiple funding sources: several rounds of federal SBIR (Small Business Innovation Research) grants, three Kickstarter crowdfundi...

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  Episode #28

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

  Jul 28, 202642 min

  Episode Summary Nancy 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 Takeaways Your 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 Shenker Nancy 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." FAQ How 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 Stack The OnSwitch — Nancy Shenker's marketing consultancy: https://www.theonswitch.com NancyAF — Nancy Shenker's personal brand site and home for her memoir updates: https://www.nancyaf.com Your 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 Vanderburg Where to Find Nancy Shenker Website (The OnSwitch): https://www.theonswitch.com Personal brand website (Nancy AF): https://www.nancyaf.com Substack memoir, Your Nerve: available via nancyaf.com Facebook: Nancy A. Shenker / Nancy AF page About Build Your Own Boat Build 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.

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