Highly Visible & A Little Misunderstood

In episode 5 of Money Unmasked, Jonathan sits down with Tai Wiggins, first-gen corporate leader, sales strategist, financial wellness educator, and founder of Debt Down Assets Up and First Gen Corporate, to explore the real tradeoffs that come with chasing money, stability, and freedom. Tai has coached hundreds of clients through debt payoff and financial resilience, but her own story is shaped just as much by layoffs, career pivots, and the pressure of navigating corporate spaces without a playbook.   Together, Jonathan and Tai unpack what it means to build a life where money is not just about survival, but about choice, confidence, and alignment. Tai shares how three layoffs between 2020 and 2024, including one during maternity leave, pushed her to rethink security, success, and what she actually values. They also talk about first-gen identity, the emotional toll of uncertainty, and why financial wellness is about much more than numbers on a spreadsheet.   In this conversation, they explore: Why Tai chose the volatile corporate tech path over a more stable government route How layoffs can shake your sense of identity, safety, and future planning What it means to be first-gen corporate and first-gen entrepreneurial at the same time The difference between financial literacy and emotional readiness How money can amplify who you already are instead of changing you Why freedom, not just income, is often the real pursuit underneath the paycheck What we’re willing to trade for security, peace, and a better life   If you’ve ever wondered whether the thing you’re chasing is actually money, or whether it’s freedom, this conversation will give you a lot to sit with. Tai brings honesty, warmth, and sharp insight to the question of what it really costs to build a life on your own terms.   Connect with Tai Wiggins: https://www.linkedin.com/in/tainycole/ https://tainycole.gumroad.com/ https://tainyc.substack.com/   🎧Listen to Previous Episode: https://www.podbean.com/ew/pb-wpr4q-1abcdbf    Stay Connected: 📺Join our Community on Youtube 📬Get updates, behind-the-scenes content, and first access to the upcoming newsletter  👉🏾Buy me Ko-fi ☕️ 🔗All links → https://linktr.ee/highlyvisiblepod 📲Follow us on Instagram  🕰️ Follow us on TikTok    Credits: Produced & Edited: Jonathan Dumas Produced & Additional Editing: Reggie Hall Socials & Community: Myron Bobyrk-Ozaki Email: [email protected] 

In episode 4 of our Money Unmasked series, Jonathan sits down with financial empowerment coach and educator rita zhang, founder of Community Roots Financials, to talk about money as something we feel in our bodies, hearts, and spirits—not just in our budgets and spreadsheets.   rita works with low‑income, immigrant, and communities of color, and she’s less interested in “perfect” financial literacy than in what it means for people to feel powerful, seen, and self‑determined in their financial lives. Together, she and Jonathan explore how stress, guilt, and anxiety around money are often coping responses to systems that were never designed with us in mind—and how slowing down to actually feel those emotions can become a deeply liberatory practice.   They get into: How rita went from racial and immigration justice organizing to financial empowerment coaching Why she thinks of her work less as “finance” and more as holding space for people’s wisdom to emerge The quiet courage it takes for working‑class and first‑gen folks to name what they truly want—not just what they need to survive How grind culture and capitalism convince us we’re “not doing enough,” even when we’re doing everything The idea of class straddlers: being the “bridge” generation between low‑income roots and a different material reality What it means to see yourself as one drop in the ocean and the whole ocean when it comes to healing, money, and lineage   If you’ve ever felt guilty for wanting more rest, more joy, or more “non‑essential” spending—or if you’ve felt behind because you don’t speak the language of traditional finance—this conversation offers a gentler, more honest way to think about money, power, and healing.   rita closes with an invitation rooted in self‑compassion: meet yourself exactly where you are, take one next step that feels possible, and let that be enough. Connect with rita zhang / Community Roots Financials: Website: https://www.communityrootsfinancials.com/  Community Roots Financials on Linkedin  Follow on Instagram: @communityrootsfinancials  Resources Mentioned in the Show (If you purchase any of the books below I get a small commission): Rest is Resistance: A Manifesto by Tricia Hersey Learn more about “Class Straddlers”   🎧Listen to Previous Episode: Redefining a "Good Life" at 30 (with Dr. Tiona Sykes)   Stay Connected: 📺Join our Community on Youtube 📬Get updates, behind-the-scenes content, and first access to the upcoming newsletter  👉🏾Buy me Ko-fi ☕️ 🔗All links → https://linktr.ee/highlyvisiblepod 📲Follow us on Instagram  🕰️ Follow us on TikTok    Credits: Produced & Edited: Jonathan Dumas Produced & Additional Editing: Reggie Hall Socials & Community: Myron Bobyrk-Ozaki Email: [email protected] 

In episode 3 of our Money Unmasked series, Jonathan sits down with licensed marriage and family therapist Dr. Tiona Sykes to unpack what happens when money, hustle culture, and our sense of worth all get tangled together. Tiona shares how growing up with the message that “nothing in life is free” shaped her belief that safety only comes from working multiple jobs and constantly grinding. Now 30 and in a season of employment transition, she reflects on what happens when that grind stops, the anxiety that surfaces, and how easy it is to feel like you’re failing even when your life looks “good” from the outside. Together, Jonathan and Dr. Sykes explore: How family stories (“you have to earn everything”) and hustle culture form our earliest money scripts The pressure to always be doing more, making more, and optimizing more—and how that erodes joy The guilt of wanting more when you were raised to “just be grateful” and not ask for too much What travel, community, and non‑U.S. cultures have taught them about money, happiness, and consumption The quiet grief and anxiety that show up around bills, debt, and time, even when the numbers technically “work” How to start redefining a “good life” at 30 in a way that honors your values, nervous system, and relationships—not just your bank account If you’ve ever looked at your life on paper and thought, “I should feel more secure than this,” or wondered what you’re actually chasing when you chase more money, this conversation will feel like exhaling with a friend who gets it. At the end, Jonathan and Tiona invite you to name your own story around enoughness and success: When you think about money right now, what emotions come up first? What would a “good life” at this stage actually look like for you? Connect with Dr. Tiona Sykes: Linkedin: https://www.linkedin.com/in/tiona-sykeslmft/  Resources Mentioned in the Show (If you purchase any of the books below I get a small commission): Psychology of Money by Morgan Housel Here is the Emotions/Feelings Wheel 🎧Listen to Previous Episode: Building Wealth That Actually Feels Good (with Reni Eniola aka xoReni)   Stay Connected: 📺Join our Community on Youtube 📬Get updates, behind-the-scenes content, and first access to the upcoming newsletter  👉🏾Buy me Ko-fi ☕️ 🔗All links → https://linktr.ee/highlyvisiblepod 📲Follow us on Instagram  🕰️ Follow us on TikTok    Credits: Produced & Edited: Jonathan Dumas Produced & Additional Editing: Reggie Hall Socials & Community: Myron Bobyrk-Ozaki Email: [email protected] 

In episode two of our Money UnMasked series, Jonathan sits down with financial educator and content creator Reni Eniola aka xoReni to talk about money, emotions, and building wealth in a way that actually feels good—not restrictive, shame-filled, or overwhelming. Reni bought her first house at 23 and has since become a trusted voice on financial literacy, career development, and “adulting” online. But beneath the milestones and the numbers, Reni is most interested in the emotional relationship we have with money—especially how childhood experiences quietly shape the way we save, spend, hustle, and dream as adults. Together, Jonathan and Reni explore: How her parents started teaching her about money at age four—and the stories that left an imprint What she thought money would give her when she bought her first house, and what it actually did Why so many of us think we have a “money problem” when what we really have is an emotional or identity story The tension between taking bold risks and having a financial safety net What people are really pursuing when they say they want “financial freedom” How to start relating to money from self-worth and self-compassion instead of fear and self-judgment If you’ve ever felt behind with money, ashamed of what you “should know by now,” or overwhelmed by all the rules and advice, this episode offers a gentler, more honest way to think about wealth, security, and the kind of life you want to build. At the end, Jonathan and Reni invite you to reflect on your own story:Money representsWhen I think about money, I feel Your answer might show you what you’re actually pursuing when you pursue money. Timestamps (Approx.) 0:00 – Intro & why this conversation matters in Money Unmasked 3:00 – Who Reni is and how she became “Reni the Resource” 7:00 – Learning about money at four years old: early lessons & family influence 13:00 – Buying a house at 23: what she hoped money would give her 20:00 – Emotions, identity, and why “just budget better” isn’t enough 28:00 – Financial risk vs. safety nets in entrepreneurship 36:00 – What people are really chasing when they chase financial freedom 44:00 – Practical ways to start healing your relationship with money 52:00 – Jonathan’s reflection & audience invitation Connect with Reni: YouTube: https://www.youtube.com/@xoReni  Instagram: https://www.instagram.com/xoreni/  TikTok: https://www.tiktok.com/@xoxoreni  Website: renitheresource.com Check out the Don’t Go Broke Collective Accountability Group Don’t Go Broke Trying Podcast:  Listen on Youtube or Apple Podcasts or wherever you get your pods  Resources Mentioned in the Show (If you purchase any of the books below I get a small commission): Rest is Resistance: A Manifesto by Tricia Hersey The Trauma of Money by Chantel Chapman The Debt Trap: The Hidden Brain Podcast  Everything but Money by Jessica Morehouse Steph & Den Free Budget Template  Money for Couples with Ramit Sethi I Will Teach You to Be Rich by Ramit Sethi 🎧Listen to Previous Episode: What Are We Really Pursuing When We Pursue Money Stay Connected: 📺Join our Community on Youtube 📬Get updates, behind-the-scenes content, and first access to the upcoming newsletter  👉🏾Buy me Ko-fi ☕️ 🔗All links → https://linktr.ee/highlyvisiblepod 📲Follow us on Instagram  🕰️ Follow us on TikTok    Credits: Produced & Edited: Jonathan Dumas Produced & Additional Editing: Reggie Hall Socials & Community: Myron Bobyrk-Ozaki Email: [email protected]

Welcome to Highly Visible, A Little Misunderstood—where we explore life's most complex conversations with curiosity, vulnerability, and zero pressure to perform. In this season premiere, host Jonathan Dumas invites you into an intimate exploration of money that goes far beyond budgeting and financial literacy. What are we really pursuing when we pursue money? Is it freedom, safety, status, or something deeper? This season—Money Unmasked—explores the tension between needing money and not wanting money to define who we are. Through personal stories, reflections on childhood lessons, and four intentional lenses (Identity, Relationships, Values, and Society), Jonathan examines how money shapes our fears, our relationships, and our sense of worth. In this episode, you'll hear: Jonathan's reframing of poverty and enoughness through his brother Reggie's wisdom: "We aren't broke—we just don't have money right now." The unintended lessons about money he inherited from his mother's generosity Why money is spiritual, emotional, and deeply connected to our unconscious fears The moral tension of success: "If we make it, how do we refuse to forget the systems that kept others out?" An invitation to share your own relationship with money This is not a season of solutions. It's a season of questions—the kind you ask at your kitchen table late at night with people you trust. If you've ever felt conflicted about wanting more while fearing what that means about you, this season is for you. Complete the sentence in the comments: "Money represents ___" or "When I think about money, I feel ___" Your responses may appear anonymously in the season finale as we reflect on what shifted together. Timestamps0:00 — Introduction, Team Updates & Welcome to Myron Bobrick Ozaki1:30 — What This Season Is (And Isn't)1:43 — The Guiding Question: What Are We Really Pursuing?2:46 — Reggie's Wisdom: "We Aren't Broke, We Just Don't Have Money Right Now"3:40 — Inherited Lessons: What His Mom Taught About Money5:37 — Money Is Emotional, Not Neutral11:13 — Four Lenses: Identity, Relationships, Values, Society11:42 — The Big Questions Holding the Season13:05 — Audience Prompt: "Money Represents " or "When I Think of Money, I Feel "15:06 — Closing Question & Invitation 📬 Stay Connected:📺 Join us on Youtube: https://www.youtube.com/@HighlyVisiblePod📬Get updates, behind-the-scenes content, and first access to the upcoming newsletter: https://heyjonathandumas.com/hvlmpod👉🏾 Buy me Ko-fi: https://ko-fi.com/highlyvisiblepod🔗 All links → https://linktr.ee/highlyvisiblepod📲 Instagram & TikTok: @highlyvisiblepod Production:Produced & Edited: Jonathan DumasProduced & Additional Editing: Reggie HallSocials & Community: Myron Bobyrk-OzakiEmail: [email protected]