Build Your Own Boat

Janine Vanderburg
  • 5.0 (6)
  • Entrepreneurship

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/

Episodes

  1. 3d ago

    How Do You Turn a Passion Project Into a Business After 50? Sky Bergman Did It With a Film, an Airbnb, and Zero Regrets

    Episode Summary This episode answers a question many women over 50 are quietly asking: is it too late to build something new? Sky Bergman — award-winning photographer, former tenured professor at Cal Poly, and founder of Sky Bergman Productions — walked away from a secure academic career in midlife to become a full-time independent filmmaker. Her debut documentary, Lives Well Lived, began as a personal search for positive role models of aging and grew into a theatrical release, a book, a community screening movement, and an intergenerational education program now used at universities across the country. In this conversation, Sky and host Janine Vanderburg dig into the real mechanics of that transition: how Sky funded her film by renting rooms on Airbnb when grants didn't come through, why she stopped doing free screenings, what it actually takes to build a network from scratch in a field you've never worked in, and why she believes the only thing you'll regret is not trying. Three new films are in production. The boat is very much still being built. What You'll Hear in This Episode How Sky started making Lives Well Lived at 4 a.m. while still serving as department chair at Cal Poly — and what finally pushed her to leaveWhy she describes herself as an "accidental entrepreneur" — and what her undergraduate business degree taught her anywayThe Airbnb funding strategy that replaced two years of failed grant applicationsHer community screening model: how organizations pay for screenings so the audience attends for freeHow she built a network of filmmaker peers starting from zero — including cold emails, LinkedIn outreach, and a backyard potluck that now draws 75 to 80 women every monthWhat she told the University of North Carolina at Wilmington when they couldn't afford her fee (and why it took six years to get there in person)A preview of three films currently in production: The Mochi Movie (featuring George Takei), The Primetime Band, and The JollytologistHer unscripted advice to any woman in her 50s, 60s, or 70s sitting on an idea she can't stop thinking aboutKey Takeaways You don't need a traditional investor to fund a creative project. When grant funding for Lives Well Lived stalled, Sky rented out spare rooms in her home on Airbnb — and turned every guest into a member of her early fan base by telling them exactly where their money was going.Asking for help is a sign of strength, not weakness. Sky learned filmmaking from Apple Store employees, cold-emailed strangers whose work she admired, and built a network of filmmaker peers she still relies on today for pricing, distribution, and strategy."Exposure" is not a business model. Sky stopped doing free screenings after realizing that work offered for free is rarely valued. Her answer to "but you're trying to change the world" — charging for her time doesn't make the work less necessary; it makes it sustainable.Weak ties open doors your closest friends can't. Sky landed an interview with George Takei for her film The Mochi Movie by emailing her network and asking if anyone knew him. Two people did. It took two years of respectful persistence — and it worked.The biggest risk is not taking one. Sky credits a woman she interviewed for Lives Well Lived, who said at 50 she could either stay in a rut or jump off the cliff. That voice still guides her decisions today.FAQS How did Sky Bergman fund her documentary Lives Well Lived? Sky was unable to secure grant funding for the film, so she rented out spare rooms in her home through Airbnb. Every guest was told their money was going toward the film. When Lives Well Lived entered film festivals, those same guests became her earliest and most enthusiastic supporters. It is one of the most practical examples of creative bootstrapping in this series. How can a woman over 50 start a business if she has no experience in that field? Sky Bergman's answer is direct: ask for help, and don't wait until you feel ready. She learned filmmaking from Apple Store employees, cold-emailed filmmakers whose work she respected, and built a peer network she still consults today. Her consistent message is that people want to help when you have a genuine idea — but you have to be willing to ask. What is Sky Bergman's approach to pricing her speaking and screening work? Sky does not do free screenings or speaking engagements unless an organization genuinely has no budget — in which case she helps them find a sponsor. Her reasoning: five years of her life went into making Lives Well Lived, and every event involves hours of coordination beyond the event itself. She pays the people who work for her, which means she cannot work for free either. What is the Lives Well Lived community screening program? Organizations — universities, nonprofits, senior centers, libraries — license a screening of the film. The screening is free for community members to attend; the hosting organization covers the cost or finds a sponsor. Sky often participates in a Q&A following the screening. The model has taken the film to communities across the United States. What films is Sky Bergman currently working on? Sky has three films in production as of this episode. The Mochi Movie explores the Japanese American experience through the tradition of mochi-making and features an interview with George Takei. The Primetime Band follows a community band of musicians in their 70s, 80s, and 90s who reconnect with instruments they set aside decades ago. The Jollytologist profiles author Allen Klein and his work on using humor to navigate difficult times. All three are expected to air on PBS, tentatively in 2027. How does Sky Bergman build her professional network? Sky emails and messages people directly — even cold — when she admires their work. She is specific, personal, and brief. She also hosts a monthly women's potluck dinner at her home in San Luis Obispo that draws 75 to 80 women from across her community. Her philosophy: you never know who someone else might know, and connection is something we all crave. Where to Find Sky Bergman Website: skybergmanproductions.comLinkedIn: linkedin.com/in/skybergman Instagram: @skybergmanproductions 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.

    36 min

  2. 3d ago

    She Built Scaffolding, Not a Safety Net: How Alrie McNiff Daniels Left a Health Foundation to Launch a Consulting Practice at Midlife

    Episode Summary What does it look like when a seasoned communications professional leaves a respected philanthropic institution in her early 60s—not because she was pushed out, but because she did the math and decided she had something better to build? In this episode of Build Your Own Boat, host Janine Vanderburg talks with Alrie McNiff Daniels, a reframing-aging consultant and communications strategist who spent nearly a decade leading communications for the Point32 Health Foundation (formerly Tufts Health Plan Foundation) before launching her own practice in September 2024. Alrie's story is a clear-eyed roadmap for women in midlife who are weighing whether to leave institutional roles and build something of their own. It covers what actually triggered her decision, how she structured her launch to reduce risk, how she got her first clients, and why she's built a thriving practice without a content strategy, a LinkedIn thought-leadership campaign, or a single cold pitch. What You'll Hear in This Episode The moment that changed everything. A friend's offhand remark—"I had one big job left in me"—sent Alrie into a week of quiet reckoning. She shares exactly what she concluded and why it pointed her toward entrepreneurship rather than another institutional role.What it means to do "the community's work." Alrie spent years amplifying the stories of community organizations rather than talking about her own institution. She explains how that orientation shaped her skills—and why it made leaving harder than it might have been otherwise."I don't think there's a market for that." Someone Alrie respected said this to her face. She shares why she didn't take the bait, drawing on what she'd watched happen to the narratives around smoking and marriage equality over her career.The scaffolding strategy. Rather than leaping without a net, Alrie thought through two complementary income streams before leaving—one in the reframing-aging space, one in corporate citizenship and employee engagement—and explains exactly how she thought about that combination.How she got her first clients without selling. Alrie made a handwritten list of two or three dozen people she'd worked with and started scheduling coffees to say thank you. Several of them immediately asked what she was charging and when they could book her.Referral-only business development. No content machine. No LinkedIn posting cadence. No cold outreach. Alrie explains what she does instead—and why it works for the kind of practice she wanted to build.How to price yourself when you come from mission-driven work. Alrie shares the three sources she used to figure out her rates, including a peer network of foundation communications consultants who were open and generous with real numbers.Experience vs. expertise. Alrie has trained governors and keynoted conferences on reframing aging—and she still refuses to call herself an expert. She explains the distinction, and why it matters for the quality of the work.Caregiving years count. One of Alrie's most direct pieces of advice: if you've stepped out of the paid workforce to provide care, you haven't lost years—you've gained skills in project management, healthcare navigation, recruiting, and more. "You probably have twice as many years as you think."The five things she'd tell any woman considering this. Know your strengths. Know what you're not good at. Be honest about your tolerance for income variability. Know your value and stop apologizing for it. Anchor everything in your core values.About Alrie McNiff Daniels Alrie McNiff Daniels is a communications strategist and reframing-aging consultant based in Massachusetts. She spent nearly a decade as Director of Communications at the Point32 Health Foundation (formerly Tufts Health Plan Foundation), where she led external communications, storytelling, and the foundation's reframing-aging initiatives. She was part of the inaugural cohort of the Frameworks Institute's Reframing Aging Training of Trainers program in 2017. Since launching her consulting practice in September 2024, she has led workshops across Massachusetts for nonprofits, aging services organizations, municipal agencies, and academic programs, and serves as an executive advisor at the Boston College Center for Corporate Citizenship. Connect With AlrieLinkedIn: https://www.linkedin.com/in/alriemcniffdaniels/ 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.

    55 min

  3. 3d ago

    How Do You Fight Age Bias at Work? Sheila Callaham Built a Global Nonprofit to Answer That Question

    Episode Summary Age discrimination in hiring is not a fringe issue—it is a structural one, and Sheila Callaham has the three-year job search spreadsheet to prove it. After a 15-year corporate communications career spanning the US, Europe, and the Middle East, Callaham returned to the workforce and received zero offers over three years—despite applying at every level, spending thousands on coaching, and doing everything "right." When she looked up who got the jobs instead, she found people who couldn't be 30 years old sitting in executive roles. That moment of clarity became the foundation for the Age Equity Alliance, a global nonprofit dedicated to eliminating age bias across all ages and life stages in the workplace. In this episode, Callaham and host Janine Vanderburg break down how she turned long-term unemployment into 200-plus Forbes articles, a knowledge partnership with AARP and the OECD, and a thriving organization she now runs from Portugal—on her own terms. Key Takeaways Age discrimination in hiring is measurable and systemic. After three years and zero job offers, Callaham tracked down the people who were hired into roles she applied for. They were not just younger—they were decades younger. The pattern was impossible to explain away.Writing about a problem and solving a problem are not the same thing. Callaham's Forbes column gave her a platform, but she knew from her change-management background that real organizational change only happens from the inside. That insight is what drove her to build Age Equity Alliance.The first client comes to you—if you build visible credibility first. Callaham did not chase her first paid employer. By year two, she was already an AARP knowledge partner on a global initiative in partnership with the OECD and the World Health Organization. The credibility came first; the client followed.Making bold asks is a learnable skill, not a personality trait. Callaham cold-pitched Ashton Applewhite on Twitter and asked AARP for a formal knowledge partnership when the organization was barely a year old. Both said yes. Her framing: the worst outcome is a 50/50 coin flip.Women over 50 already have what they need. The gap is not competence—it is belief. Callaham's message to women sitting on decades of expertise: stop waiting for someone to discover your talent and build your own boat.FAQs What is the Age Equity Alliance? The Age Equity Alliance is a US-based global nonprofit, headquartered in Austin, Texas, dedicated to eliminating age bias and stereotyping in the workplace—across all ages and life stages. It works directly with employers to identify how age bias shows up in hiring, development, retention, and promotion decisions, and helps organizations commit to measurable change. It operates largely as a volunteer organization and has its strongest market traction in Europe. What is the Mobley v. Workday lawsuit and why does it matter for age discrimination? Mobley v. Workday is an active federal discrimination case in Northern California alleging that Workday's hiring algorithms disproportionately screened out applicants based on race, disability, and age. For age discrimination specifically, the case tests whether AI-driven screening tools violate the Age Discrimination in Employment Act (ADEA). Workday's attempts to have the case dismissed—including arguments that the software, not the employer, made hiring decisions, and that applicants are not covered under the ADEA—have so far been rejected by the court. A ruling in favor of the plaintiffs could create employer accountability for algorithmic age bias at a scale not seen before. How do women over 50 successfully transition from corporate careers to entrepreneurship? According to Callaham, the skills that matter most—team building, change management, stakeholder communication, and the ability to hold a vision under pressure—are exactly what experienced corporate professionals have already developed. The practical gap is operational: learning to do everything yourself, stretch a budget, and ship work that is useful rather than waiting for it to be perfect. The psychological gap is belief. The strategic gap is visibility: building credibility publicly before the first client appears, rather than chasing clients before you have proof of value. What does "building your own boat" mean for women in midlife? It means recognizing that if the job market, workplace, or industry you built your career inside is no longer working for you, the answer is not to apply harder—it is to build something of your own. The expertise, relationships, and perspective you have accumulated are the raw material. The boat is what you build with them. How do you price services for a nonprofit or social enterprise? Callaham's framework: build visible credibility and expertise first (through free training, speaking, writing, and partnerships), so that clients come to you already convinced of your value. Once you are in a negotiating position, name your price with confidence—there is no universal rate, and one determines one's own value. Speaking without a fee is only worth it when there is a clear, specific return: access, credibility, partnerships, or market exposure. About Sheila Callaham Sheila Callaham is a globally recognized expert on age equity in the workplace, a Forbes contributor, and the co-founder of the Age Equity Alliance—a nonprofit dedicated to eliminating age bias and stereotyping for workers of all ages and life stages. She brings to that work a career that spans civil service with the US Department of the Army, corporate communications for a global pharmaceutical company, defense contracting, and extensive work across the US, Europe, and the Middle East. After 15 years in corporate—12 of them leading inclusion and diversity initiatives—Callaham stepped away to focus on her family. When she tried to return to the workforce years later, she encountered the very bias she had once helped organizations address. Three years and zero job offers later, she channeled her experience and her frustration into a cold pitch to Forbes. A month later, she had a column. She has been writing about age equity, multigenerational workplaces, and the business case for age inclusion ever since—publishing more than 200 articles to date. In 2019, she co-founded the Age Equity Alliance, launching it in January 2020 under the mentorship of anti-ageism activist Ashton Applewhite. The organization has since grown into a knowledge partner with AARP and the OECD's Living, Learning & Earning Longer initiative, and has its strongest market traction in Europe, where Callaham now lives, splitting time between Portugal and France. She is a sought-after speaker, a researcher, and a fierce advocate for the idea that experience is an asset—not a liability. Connect with Sheila Callaham 🌐 Website: ageequityalliance.org 💼 LinkedIn: linkedin.com/in/sheilacallaham 📰 Forbes: forbes.com/sites/sheilacallaham 📺 YouTube: youtube.com/@AgeEquityAlliance About Build Your Own Boat Build Your Own Boat is a podcast serie...

    43 min

  4. 3d ago

    Can You Start a Business After 50? Ande Lyons Has Done It—More Than Once

    Episode SummaryThis episode answers a question millions of women in midlife are quietly asking: is it too late to start something new? The short answer, backed by decades of lived experience, is no—and Ande Lyons is the proof. Ande Lyons, 69, is a serial entrepreneur who has launched and closed multiple businesses across completely different industries—from dot-com venture capital and a nationally distributed food brand to a desire-and-intimacy platform, a startup mentoring practice, and now a pro-aging podcast and thriving podcaster community. She has raised angel funding, survived a lightning strike that burned her manufacturing facility to the ground, been "shamed out" of a business by her peers, and come back every single time. In this conversation, Ande and host Janine Vanderburg unpack the real story behind building a business at any age—the failures no one posts about, the internalized ageism that sneaks in around age 50, and the practical, MBA-tested framework Ande uses to test ideas before betting everything on them. If you have ever talked yourself out of starting something because you thought you were too old, this episode is your reframe. Key Takeaways Failure is part of the business-building curriculum. Ande's position is that you always win when you launch a business, even when it closes—because the skills, self-knowledge, and market insight you gain directly fund your next venture. Most successful businesses are not the founder's first.Ageism in entrepreneurship is learned, not innate. The belief that entrepreneurship belongs to the young is absorbed slowly over decades through media, pop culture, and even well-meaning people who stop asking "what do you want?" and start asking "when are you retiring?" Recognizing it as indoctrination is the first step to dismantling it.Launching a podcast is one of the fastest ways to become an expert in a new industry. Ande has used this strategy repeatedly: enter a new space, interview the established experts, ask every question you have, and let the content build your credibility while you learn.Build in public before you build in full. Ande's New England Podcasters Group started as a single monthly in-person event to test whether people would show up. Only after proving consistent attendance did she introduce a paid membership—and the founding member price of $100/year for life made it an easy yes.Midlife is not the end of ambition; it is the beginning of clarity. At 50+, you finally know who you are, what you will and will not tolerate, and what genuinely lights you up. That self-knowledge is a competitive advantage that no 28-year-old founder can buy.Frequently Asked Questions Is it too late to start a business after 50? No. Ande Lyons has launched businesses in her 30s, 40s, 50s, and 60s—and she argues that midlife may actually be the best time to start. By 50, most women have decades of domain expertise, a strong professional network, clearer personal values, and a much sharper sense of what problem they actually want to solve. The belief that entrepreneurship belongs to young people is a culturally absorbed assumption, not a fact. What is the biggest mistake new entrepreneurs make with marketing? According to Ande, the most common and costly mistake is treating marketing as a creative exercise—clever copy, eye-catching graphics, and social media posts—rather than a data discipline. Marketing is fundamentally a numbers game. Understanding your target market, your customer acquisition cost (CAC), your lifetime customer value (LTV), and your break-even point matters far more than any single viral post. How do you test a business idea before going all in? Ande's method is to start small and build in public. For her New England Podcasters Group, she ran a free monthly in-person event for nearly a year before introducing any paid tier. When she saw consistent attendance and growing demand, she introduced a founding membership at a price that made the decision easy. Proof of concept before capital commitment is the through line across all of her ventures. How do you transition from one professional identity to a new one? Deliberately, and with a bridge. When Ande moved from startup mentor to pro-aging advocate, she did not just rebrand overnight. She ran a 30-episode podcast season called Your Ink Story—interviews about people's tattoos—as a "palate cleanser" that kept her publishing, kept her audience engaged, and gave her time to develop the new platform without a jarring public pivot. What should women in midlife do first if they want to start a business? Ande recommends starting with deep self-inquiry before strategy. Her go-to resource is Don't Retire, Rewire by Jerry Sedler, which offers structured questions to help you identify what genuinely lights you up. From there, the practical steps follow: identify the problem you want to solve, confirm that people will pay for the solution, and launch before you feel ready—because the real learning starts the moment you open for business. What is the New England Podcasters Group and the Podgarden? The New England Podcasters Group is a community Ande founded in May 2024 for independent podcasters across New England (Connecticut, Rhode Island, Massachusetts, New Hampshire, Vermont, and Maine). It meets monthly at a TV and podcast studio in Westford, MA. The Podgarden is the group's owned online community platform, launched in June 2025, which extended membership to podcasters worldwide. Its goal is to solve the isolation that independent creators often experience by building genuine, ongoing connection—both in person and online. Find Ande LyonsWebsite: https://www.dontbecagedbyyourage.com/LinkedIn: https://www.linkedin.com/in/andelyons/ About Ande Lyons Ande Lyons is a five-time business founder, startup champion, and the host and producer of the Don't Be Caged By Your Age podcast — a pro-aging show dedicated to dissolving the internalized beliefs that tell us our best years are behind us. Over a career spanning more than three decades, Ande has built businesses across wildly different industries: from co-founding CollegeBroadcast.com (one of the first streaming entertainment platforms for college campuses, backed by $8M in venture capital) to scaling Goddess Granola into a nationally distributed women-owned brand, to mentoring hundreds of early-stage startup founders across the Boston ecosystem. She has raised angel funding, judged and co-produced pitch events, and served as a mentor in accelerator programs throughout Massachusetts. In 2024, she founded the New England Podcasters Group, a thriving in-person and online community for independent podcasters across New England and beyond — built on her conviction that the antidote to creator isolation is genuine human connection. The community's online home, the Podgarden, launched in 2025 and now includes members from around the world. Ande is an energetic connector who has spent years bridging the gap between the energy of young founders and the hard-won wisdom of older entrepreneurs. Her core belief is simple and a little radical: innovation is ageless, the Third Act can be the most creatively fertile period of a life, and the only thing standing between most people and their next great venture is the story they've been told — and started telling themselves — ...

    43 min

  5. 3d ago

    How Do You Start a Business After 50 When No One Will Hire You? Barbara Brooks Did It — and Built a Community of 24,000

    Summary Barbara Brooks, founder of Second Act Women and pro-age keynote speaker, sent out 100 resumes in 2018 as an award-winning marketing director — and received zero job offers. Instead of waiting for a door to open, she built her own. This episode of Build Your Own Boat answers a question thousands of women over 50 are asking right now: Can I really start a business at this stage of life, and what does it actually take? Barbara's answer is a clear yes — grounded in seven-plus years of real-world experience building a 24,000-member women's community from scratch, surviving a pandemic, navigating caregiver burnout, and restructuring her entire revenue model in midlife. This is not an inspiration story with the hard parts edited out. It is a practical, honest account of what solo entrepreneurship over 50 actually costs, what nearly ended the company, and what Barbara would do differently if she started today. Key Takeaways Ageism in hiring is a data problem, not a personal one. Barbara sent 100 resumes, received five interviews, got ghosted on several, and received zero offers — despite being an award-winning marketing director. The experience that gets women pushed out of corporate America is precisely the edge they need to build their own companies.Building a community business around a stigmatized identity is a long game. Second Act Women sold only 25 of 250 tickets to its first event in 2019 because women weren't yet ready to publicly own their age. By 2023, those same women were standing up and shouting their age with pride. Cultural change takes time — and repetition.Solo aging and solo entrepreneurship carry real, unspoken financial costs. As a solo ager — single, child-free, with no second income in the household — Barbara carries 100% of her financial risk. The entrepreneurship stories that skip over this detail are doing women a disservice.Caregiving and entrepreneurship collide more often than anyone talks about. When Barbara's mother had a stroke in 2023, she was already running on burnout. She considered shutting the company down entirely. Understanding that caregiving and business-building can overlap — and planning for it — is essential, not optional.You cannot scale a company you haven't built a revenue strategy for. Barbara spent years making other women visible while her own financial foundation stayed shaky. Her turning point was deciding to stop being the janitor and the admin and start being the CEO — with quarterly revenue goals, weekly sales focus, and structured time-blocking.Episode FAQ What is Second Act Women and who is it for? Second Act Women is a community of 24,000 women and allies focused on midlife reinvention, entrepreneurship, career transition, and owning your age. It was founded by Barbara Brooks in 2018–2019 for women over 40, 50, and 60 who are navigating what comes next — whether that means starting a business, changing careers, or simply finding a community of people who understand where they are in life. How did Barbara Brooks start a business after being rejected from 100 jobs? After sending out 100 resumes and receiving zero job offers despite decades of experience as an award-winning marketing director, Barbara took an idea she'd been holding on the shelf and started building it. She brought women into rooms to brainstorm, kept hearing the same unmet need, and eventually landed on the name Second Act Women during a Monday night breakthrough moment in December 2018. What does it mean to be a solo ager running a business? A solo ager is someone navigating midlife — and entrepreneurship — without a partner, second income, or built-in support system at home. For Barbara, that means every business expense, every late-night pitch deck, every moment of doubt, and every financial risk lands entirely on her. It is more expensive, more isolating, and more exhausting than most entrepreneurship narratives acknowledge. How do you balance caregiving with running a business? Barbara became a caregiver after her mother suffered a stroke on March 16, 2023. She describes living in a state of anticipatory grief — never knowing what the next phone call will bring. Her advice: get legal and financial documents in order for aging family members before a crisis hits, talk openly about the emotional and financial toll caregiving takes on business owners, and treat self-care as a structural business necessity, not a luxury. What is "return on experience" and why does it matter to corporations? Return on experience is Barbara Brooks' framework for communicating the business value of hiring workers over 50. Her argument to corporations: age-diverse, five-generation workplaces see measurable gains in productivity, creativity, and innovation. With one in three Americans now over 50, companies that dismiss experienced workers are making a provably bad business decision. What should a woman over 50 do before launching a business? Barbara's concrete starting framework: identify the specific problem only you can solve, write a one-page business plan, define your target audience, build your key messaging and elevator pitch, set a revenue goal and break it down by quarter and month, and get visible — especially on LinkedIn. The most important move, she says, is getting it out of your head and onto paper. About the Guest Barbara Brooks is the founder of Second Act Women, a 24,000-member community for women navigating midlife reinvention, and a keynote speaker whose signature message — Age Is an Advantage — challenges corporations to recognize the measurable business value of age-inclusive, five-generation workplaces. A three-time entrepreneur with a background in marketing, PR, and media sales, Barbara has been a leading pro-age voice since 2018. She was named one of the Top 25 Women in Business by the Colorado Women's Chamber of Commerce in 2023 and is a 2026 Denver Business Journal Women in Business honoree. Find Barbara Brooks Speaking, keynotes & media inquiries: BarbaraBrooks.comSecond Act Women community: SecondActWomen.comLinkedIn: linkedin.com/in/barbaralbrooksAbout 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. Subscribe to the Substack newsletter here.

    42 min

  6. Jun 4

    From Fortune 500 to Founder: How Colleen Paulson Built Ageless Careers—and Why Women Over 50 Are the Most Underestimated Entrepreneurs in America

    What happens when a top-performing Fortune 500 engineer decides the system isn't worth fighting anymore—and builds something better on her own terms? In this episode of Build Your Own Boat, host Janine Vanderburg sits down with Colleen Paulson, founder of Ageless Careers and one of LinkedIn's most trusted voices on age discrimination in the workplace. Colleen holds an engineering degree and an MBA, built her career at Procter & Gamble and FedEx, and walked away from it all after being told she could come back to work full time—or not at all. No job share. No flexibility. No exceptions. That was 2006. Since then, she has built a thriving practice helping professionals over 50 fight age bias, rewrite their stories, and land roles that actually value what they bring. She has worked with more than a thousand executives, grown a LinkedIn following approaching 100,000, and rebuilt her entire business—twice—on her own terms. This conversation covers all of it: the corporate ultimatum that made her decision easy, the single cold email that launched her business, what age discrimination actually looks like up close, and what she would tell any woman sitting at a kitchen table wondering if she has what it takes to start something new. She does. Here's the proof. What You'll Learn in This Episode Why flexibility—not ambition—was the breaking point that pushed a Fortune 500 top performer out the doorHow one cold email to a Yahoo Finance columnist became the foundation of a 20-year businessWhat age bias really looks like when experienced professionals walk through the door of a hiring processWhy "staying in corporate" is no longer the safe choice—and what the data says about who is actually at riskThe LinkedIn strategy that rebuilt Colleen's business after COVID and now drives more than 80% of her clientsWhy women over 50 are uniquely positioned to build businesses—and what most of them are still getting wrongHow to find the "through line" in a nonlinear career and use it as your greatest competitive assetThe one thing Colleen wishes she had done 10 years earlier (and why it's not too late for you to do it now)Where to find Colleen Paulson 🌐 Website: agelesscareers.com 💼 LinkedIn: linkedin.com/in/colleenpaulson

    36 min

  7. Jun 4

    How Do Women Over 50 Stop Starting Over? Donna Cravotta on Tried & New, Intentional Visibility, and Building From What You Already Have

    What if the thing holding accomplished women back isn't a lack of skills or experience — but the pressure to start from scratch every time they want something new? In this episode of Build Your Own Boat, host Janine Vanderburg talks with Donna Cravotta — founder of Cravotta Media Group, creator of the Intentional Visibility Project on Substack, and host of the Real 50 Over 50, a weekly livestream series now in its third year featuring nearly 200 women redefining leadership and visibility after 50. Donna's path includes 25 years in law firms, a first business launched at 42 as a virtual assistant (before that was a real category), and a deliberate pause at 58 to ask — for the first time — what she actually wanted. What emerged from that pause is her methodology: Tried & New, a framework that helps accomplished women stop starting over and start building from what they already have. This conversation covers all of it: the career pivot that started at a diner at nine o'clock at night, the hand cream client who generated $100,000 in sales in eight months with no budget, what 200 interviews with women over 50 actually revealed (hint: it wasn't "reinvention"), and the wisdom bomb every woman sitting on the edge of something new needs to hear. Where to find Donna Cravotta Substack — Intentional Visibility Project: @DonnaCravotta LinkedIn: Donna Cravotta Website: Cravotta Media Group

    42 min

  8. Jun 4

    From Amazon Alexa to AI Entrepreneur: Polly Allen on Burnout, Building a Business, and Creating Security on Your Own Terms

    What does it actually take for a woman to walk away from a high-level corporate job—one with status, a good salary, and a brand name on the resume—and build something entirely her own? In this episode of Build Your Own Boat, host Janine Vanderburg talks with Polly Allen, former Principal Project Manager on Amazon Alexa AI and founder of two ventures: AI Career Boost, a program helping professionals become AI-fluent leaders, and Escape Velocity AI Studio, which helps business owners and aspiring entrepreneurs build their first AI-powered revenue stream. Polly's story is a real account of burnout so severe she took six months of medical leave, the financial math she ran before quitting, the loneliness of launching a webinar with no proof points, and the accidental Calendly moment that generated 130 customer conversations in three weeks. Questions This Episode Answers How do you know when burnout has crossed a line you can't come back from?What financial runway do you actually need before leaving a corporate job?How do you sell something before you've finished building it?Why do women consistently underprice their services, and how do you break that habit?Can you build an AI-powered product or business without a technical background?What does "action comes before clarity" mean in practice—and how do you apply it when you're scared?How do women use their corporate experience as a competitive advantage when starting a new business?Is it too late to build something with AI if you haven't started yet?Key Insights from This Episode Corporate environments were not designed for women. Polly is direct about this: the systems that rewarded the people around her were built for people whose domestic lives were managed by someone else. Understanding this brings the clarity that opens the door to building differently.The risk of entrepreneurship is smaller than you've been told. Before Polly left Amazon, she calculated her runway, then asked herself a harder question: When's the last time I really tried to figure something out and failed for six months in a row? The answer reframed everything.Sell first, build second. The biggest mistake new entrepreneurs make is building a complete product before testing whether anyone wants it. Polly's first 16 clients came from a program that wasn't finished yet.Pricing is a mindset problem, not a math problem. Polly's 10x game: before setting a price, ask whether the offer is worth ten times what you're charging. If you can own that story and believe it, you're no longer underselling. Charge for outcomes, not hours.You will have to do it afraid. Before her first public webinar, Polly nearly cancelled. She didn't. Her word for that moment: you're going to have to do it afraid.AI has lowered the barrier to building a product dramatically. Tools like Lovable now allow non-technical founders to describe what they want in plain English and have a working product in an afternoon. The hard part is no longer building. It's knowing what to build and for whom.Where to find Polly Allen 🔗 LinkedIn: Polly M. Allen 💻 AI Career Boost: aicareerboost.com 🚀 Escape Velocity AI Studio: escapevelocityai.studio

    38 min

  9. Jun 4

    From Nonprofit CEO to Cookie Entrepreneur: How Liddy Romero Built a $250K Business in Midlife After Divorce

    What does it actually look like to walk away from a celebrated career — with nothing in your pocket — and build something new? Liddy Romero did exactly that. For sixteen years, Liddy ran Work-Life Partnership, a nationally recognized Colorado nonprofit social enterprise she founded that helped over 200,000 frontline workers navigate real crises — housing instability, domestic violence, childcare emergencies — in partnership with companies like Starbucks and The Gap. She raised millions of dollars, won national awards, and helped take the program from a single-county Colorado initiative to a model replicated across the country. Then, in 2024, she walked away. No severance. No profit sharing. Zero. What came next is a story about transferable skills, strategic risk, cultural pride, and what happens when a CEO-level brain gets pointed at a four-generation family recipe that had never left South Texas. Today Liddy runs Romero Cookies — a handmade, elevated Mexican heritage cookie business built around the pan de polvo (Mexican wedding cookie) her family made in their Rio Grande Valley bakery for forty years. In her first full year of business, she hit $250,000 in sales. What You'll Learn in This Episode How to fund a product business with no revenue — Liddy used her knowledge of community development financial institutions to land a $150,000 small business loan before she'd sold a single cookieWhy nonprofit skills transfer directly to for-profit entrepreneurship — from closing corporate contracts to building financial models, nothing she learned was wastedHow to test a product idea before you know how to make it — Liddy ran Meta ads before she had a recipeThe mindset shift from social impact to personal wealth building — and why it matters for women who have spent careers fundraising for othersHow to say no to bad opportunities — even when cash flow is tight and the offer is sitting right in front of youWhat corporate gifting looks like as a business model — and why it beats the consumer packaged goods margin game for a bootstrapped brandWhere to find Liddy Romero and Romero Cookies 🌐 Website: romerocookies.com📸 Instagram: @RomeroCookies💼 LinkedIn: Liddy Romero on LinkedIn🛍️ Shop: romerocookies.com (corporate gifting inquiries go directly to Liddy via the contact form)🏪 In-store: Coming soon to Tony's Market, Colorado

    38 min

  10. Jun 4

    From Corporate Layoff to Coaching Empire: How Kami Guildner Built a Business Around Helping Women Entrepreneurs Find Their Voice

    Kami Guildner spent nearly two decades building a career in oil and gas, rising to VP of Marketing and Branding before a 2008 layoff changed everything. What followed was 17 months of uncertainty, an epiphany in a barn with her horse, and the launch of a coaching practice she has now run for 17 years. Today, Kami works with high-achieving women entrepreneurs through her Movement Maker Mastermind, her annual Extraordinary Women Ignite conference, and her award-winning podcast Extraordinary Women Radio — all in service of a singular vision: to help 1 million women raise their voices, their visibility, and their revenue. In this episode, she shares what actually works when you're building a business from scratch after a corporate career, why focus is the most underrated business strategy, and what she's learned from nearly two decades of coaching women who are done waiting for permission. Where to Find Kami Guildner Website: kamiguildner.comPodcast: Extraordinary Women Radio (available on all major podcast platforms)Conference: Extraordinary Women IgniteLinkedIn: linkedin.com/in/kamiguildnerInstagram: @kamiguildnerFree monthly trainings: Sign up at kamiguildner.com

    35 min

  11. May 31

    Trailer

    Build Your Own Boat, an entrepreneurship podcast for women in midlife and beyond will drop on June 4. The podcast will feature stories, lessons learned, and actionable advice from women who have started new entrepreneurial ventures in midlife and beyond.

    2 min

Trailer

Ratings & Reviews

5
out of 5
6 Ratings

About

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/

Information

  • Creator
    Janine Vanderburg
  • Years Active
    2K
  • Episodes
    11
  • Rating
    Clean
  • Copyright
    © Janine Vanderburg

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