From Abandoned at 11 to Trusted Advisor to Millionaires: Victoria Woods' Story

In this episode of Unconventional Wisdom About Conventional Wisdom, Kim Miller-Hershon sits down with Victoria Woods wealth advisor, trusted advisor to millionaires, and founder and CEO of Chapelwood Financial Services, where she specializes in high-net-worth investment advisory. Victoria has been featured in Newsweek, named one of 100 Women to Know in America in 2023, and is the author of It's All About the Money, Honey. Victoria's story doesn't begin with wealth. It begins with a father who abandoned the family when she was eleven, a stay-at-home mom suddenly raising four kids on $96-a-month rent, and a childhood spent cooking for her siblings on a hot plate. She started babysitting at twelve and quickly went from minding one child to running six at a time. She built a celebrated retail career, walked away from the corporate world at twenty-three, and eventually built three companies over three decades. In this conversation, Victoria challenges one of the most paralyzing beliefs in business: the idea that you have to have all the answers before you're allowed to lead. Early on, she pretended she had it all figured out confident on the outside, "sweat running down my back" on the inside. What she learned was that nobody expects you to know everything, and admitting you don't isn't weakness. The real skill is being clear about who you are and where you're going, then having the nerve to ask for help getting there. A turning point came the night she asked her store manager for a raise she had earned top sales, most departments and was told the money was going to "Lazy Bill" in furniture instead, because Bill was married with children and she was single. By the next morning she was clear: she would never again let someone else decide her worth. It's the moment that crystallized the phrase she still lives by in the absence of courage, do it scared. Much of the episode is a masterclass in asking for what you want. Victoria describes the goal card she created in her fifties her photo, a QR code, and a handful of specific annual goals which she hands to powerful people across the table, then sits back in silence and lets them volunteer how they can help. She writes their names down, names the commitment out loud, and follows up. Even her own business coach was left speechless watching it work. Victoria and Kim also dig into generosity as a discipline rather than a reward "give while you're living" and the lesson that what you give out rarely returns from the direction you sent it, but always returns. They talk about the loneliness of building something that eventually doesn't need you, which is exactly the point: if the company depends on the founder, Victoria says flatly, you don't have a business, you have a hobby. And underneath it all, she's candid that imposter syndrome never fully leaves her answer is the same as always: keep serving, keep moving, and don't take advice from broke people. This episode explores: Why you don't need all the answers to start — and why pretending you do holds you back How a childhood of scarcity became an entrepreneurial education The raise that wasn't, and the "fork in the road" moment that changed everything "In the absence of courage, do it scared" as a working philosophy The goal-card method for asking powerful people for help — and why silence is the secret Why asking for advice is a strength, not a weakness Giving while you're living, and treating generosity as a responsibility That you don't have to be rich to help: a dollar's a dollar Why a business that depends on its founder isn't really a business The bittersweet goal of training your team so well that clients stop needing you Why imposter syndrome can persist at every level of success Speaking to clients in plain English instead of jargon "Don't take advice from broke people" — and how to vet credibility before you listen Victoria's perspective is a powerful reminder that success isn't about arriving with all the answers it's about clarity, courage, and a willingness to keep serving even when you're scared. Her journey from a broken stove and floated checks to one of the most respected women-owned advisory firms in the country shows that you can build real wealth without losing your warmth. If you're an entrepreneur, advisor, leader, or anyone who's ever felt like they don't quite belong in the room, this conversation offers practical tools, hard-won wisdom, and a refreshing case that the bravest thing you can do is ask for what you want and then do the work. Connect with me here: Website: https://www.kimmillerhershon.com LinkedIn: https://www.linkedin.com/in/kmillerhershon Newsletter: https://link.kimmillerhershon.com/widget/form/aEdmdA1W5MhoMCMfy5O8 Webinar: https://webinar.kimmillerhershon.com/?utm_source=Podcast Guest Details: Guest: Victoria Woods Company: Chapelwood Financial Services Book: It's All About the Money, Honey (also available as an audiobook) Website: FinancialDiva.com Hosted by Simplecast, an AdsWizz company. 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