First-Gen Millionaire on a Teacher Salary — with Davy Yap

From Teacher to Author, Speaker, and Founder: Building a Calling Beyond the Classroom — with Rochelle Wilson

Rochelle Wilson was a sixth-grade ELA teacher who saw a problem she couldn’t look away from. When a student she was mentoring through a painful season needed someone in her corner, Rochelle showed up — and one lunch period turned into fifteen girls, then thirty, then sixty, then a full mentoring program. That program became Intelligent and Ambitious Minds — her “I AM” mentoring — and the calling kept growing from there: a published book, a national speaking career, and a company of her own. This conversation is for the teacher holding a dream they keep moving to “next year.” Rochelle walks through her “Prepare Them with Purpose” framework, the real (and unglamorous) sacrifices behind building something while teaching, how an anti-TikTok teacher became a sought-after keynote speaker, and the money fears wrapped up in betting on yourself. Her throughline: take the chance on the thing that scares you — the dream you can’t stop thinking about is usually the one that’s yours to chase. This episode covers: • How a single act of mentorship grew into Intelligent and Ambitious Minds — Rochelle’s “I AM” program — and what it taught her about purpose • “Prepare Them with Purpose”: her framework for living your purpose first so you can actually teach it — because kids always know when you’re faking it • The problem that won’t leave you alone: why the thing that bothers you more than it bothers your colleagues might be the breadcrumb to your calling • “Positive jealousy,” or teacher envy — how to read the ache of wanting what someone else has as a signal, not a flaw • What it actually took to build it: trust, terror, four years of consistency, and real sacrifice (Rochelle is a mom of four who wrote her book on lunch breaks and summers) • Becoming a speaker by saying yes before she felt ready — her very first ask was a keynote — and how social media (and her students) opened the doors • Self-publishing Purpose Over Popularity on Amazon KDP: what she’d do differently, and the second book on the way • The money side of the leap: building income beyond the paycheck, and what she’d say to a teacher who’s scared to start • The one move for this week — write the dream down, put it where you’ll see it, and say it out loud as if it has already happened 🍏 Rochelle’s book: Purpose Over Popularity: Living Beyond Likes and Follows  Connect with Rochelle: @mrs.wilsonsclassroom (Instagram) [https://www.instagram.com/mrs.wilsonsclassroom/] Mrs. Wilson’s Classroom (YouTube) [https://www.youtube.com/channel/UCMOa7T2uLQulg9eCCIY3klQ] Rochelle Wilson (LinkedIn) [https://www.linkedin.com/in/rochelle-wilson-58226a327] mrswilsonsclassrm.com — newsletter, freebies + the I AM mentoring program [https://www.mrswilsonsclassrm.com/] Purpose Over Popularity (book) [https://www.amazon.com/Purpose-Over-Popularity-Living-Follows/dp/B0BF2XK6FQ] 🎧 Subscribe now for new episodes every Tuesday. Come hang: Instagram → @teacherswithmoney [https://www.instagram.com/teacherswithmoney/] Instagram (Christa) → @christajeanjones [https://www.instagram.com/christajeanjones/] LinkedIn → Christa Jones [https://www.linkedin.com/in/christajeanjones/] Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab [https://christajones.samcart.com/products/tpt-launch-lab] This podcast is for educational and entertainment purposes only and does not constitute financial advice.

Get RICH on Your Terms: A New Definition of Wealth — with Jenn Jamali of First Jenn Money

Jenn Jamali spent years in tech — at companies like Indeed and Spotify — negotiating other people’s salaries for a living. Then, at eight weeks pregnant, she was laid off. Instead of scrambling, she leaned into a plan she’d already started building: during the pandemic she got obsessed with money, bought her first investment property, and turned all of it into First Jenn Money, where she now coaches women to build real wealth on their own terms.  This is a warm, honest conversation between two friends — and two reformed “I’m just bad with money” spenders — about what rich actually means. Jenn breaks down her full RICH framework, gets practical about the first money system a tired teacher can truly automate, and reframes wealth as options: control over your time at every stage of life. This episode covers: • How Jenn went from “ask my husband about the finances” to real estate investor — and why money is a skill you can learn, not a personality trait you’re stuck with • The story behind the name First Jenn Money, and getting laid off at eight weeks pregnant — and how years of money and mindset work turned a scary moment into the start of her business • Jenn’s RICH framework, piece by piece: Rewrite your money story · Integrate systems for saving and investing · Career and money-making capabilities · Honor your values • Money as three separate skills — making it, managing it, and spending it — and why spending is the one nobody teaches (especially women) • The first system for an exhausted teacher: a six-month emergency fund you automate straight from your paycheck, starting as small as $25, kept in a separate high-yield savings account • Redefining “rich” as options and time freedom — Jenn now runs her business from Bogotá, Colombia • Values-based spending without white-knuckling: the “leave it in the cart for a week” hack, a $100/month laundry service, and the twice-a-year salon splurge • Vision boards that actually work — putting a real picture to the dream, from a Business Insider feature to the life you’re building Connect with Jenn: @firstjennmoney (Instagram) [https://www.instagram.com/firstjennmoney/] Jenn Jamali (LinkedIn) [https://www.linkedin.com/in/jenn-jamali-/] firstjennmoney.com [https://www.firstjennmoney.com/] Newsletter — raw, real money stories + challenges [https://firstjennmoney.myflodesk.com/gie0t8qnen] RICH Reset Roadmap Call with Jenn [https://calendly.com/firstjennmoney/richreset?month=2026-06] Payday Club Podcast (find it wherever you listen) Jenn Jamali is a money coach; this episode is for educational and informational purposes only and isn’t personalized financial advice. Always consult a qualified financial professional about your specific situation. 🎧 Subscribe now for new episodes every Tuesday. Come hang: Instagram → @teacherswithmoney [https://www.instagram.com/teacherswithmoney/] Instagram (Christa) → @christajeanjones [https://www.instagram.com/christajeanjones/] LinkedIn → Christa Jones [https://www.linkedin.com/in/christajeanjones/] Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab [https://christajones.samcart.com/products/tpt-launch-lab] This podcast is for educational and entertainment purposes only and does not constitute financial advice.

Teacher Boundaries and Knowing When to Say No: Union Work and Online Summits — with Bryson Tarbet of That Music Teacher

Bryson Tarbet is a former PreK–6 music teacher and the founder of ThatMusicTeacher.com and Tarbet Education Network, where he builds content-specific professional development for music and arts specialists. He's also one of the earliest supporters of Teachers With Money — someone who helped Christa workshop the mission months before this show was live. This is a conversation between two former elementary music teachers who both stepped out of the classroom and never stopped fighting for the people still in it. Bryson coined a phrase for something a lot of teachers feel but can't quite name: the Specialist's Burden — the isolation of being the only one doing your job in the building, with no team and no support built for your content. From there the conversation opens into the bigger setup underneath it: the story that your sacrifice is your value, that asking for more somehow makes you a worse teacher. Bryson and Christa trace that same story across three levels — the classroom, the business, and the bargaining table — and land on the one boundary every teacher can start practicing tomorrow. This episode covers: * The Specialist's Burden — why being the only music, art, or PE teacher in your building leaves you isolated and underserved by general PD, and why naming it out loud is the first move toward fixing it * "Do it for the kids" as systemic gaslighting — how a phrase that sounds noble puts the whole broken system on teachers' shoulders, and Bryson's reframe that flips it: teacher working conditions are student learning conditions * The charging guilt that follows you out of the classroom — why "I should just give it away for free" is the same voice that ran you ragged in the room, and how Bryson made peace with charging by anchoring to his values: inclusivity, community empowerment, advocacy * Inside the summit model — how free access funds paid access funds free initiatives, and why putting it all on the table (no sneaky tactics, "we can still be friends if you don't upgrade") is both the kinder and the more sustainable way to sell * Paying speakers fairly — how Bryson moved from affiliate-only to a base-pay-plus-affiliate hybrid so it's not only the big audiences that get paid, and how he coaches first-time speakers to leverage the opportunity * The collective layer — Bryson's years as a union rep and then VP, what he saw on the negotiations team during a contract year that came right up to a strike, and why individual mindset work and collective action are the same conversation, not either/or * Where to start if you've never opened your contract — read it, know it word for word, and remember that a union is only as strong as the people in it * The one walkaway: it's okay to say no — why saying no is the boundary that protects both your health and your career, and how it pushes the system to deal with what it's been quietly offloading onto teachers 🎵 Music teacher friends: Join us for the Summer 2026 Elementary Music Summit! [https://christa_jones--thatmusicteacher.thrivecart.com/all-access-pass-jul26-fa/]*   Connect with Bryson: ThatMusicTeacher.com — for elementary music teachers [https://thatmusicteacher.com] Tarbet Education Network — for arts specialists [https://tarbeteducationnetwork.com] @thatmusicteacher (Instagram) [https://www.instagram.com/thatmusicteacher/] Bryson Tarbet (LinkedIn) [https://www.linkedin.com/in/bryson-tarbet] *This is an affiliate link — Christa may earn a commission if you register through it, at no additional cost to you. 🎧 Subscribe now for new episodes every Tuesday. Come hang: Instagram → @teacherswithmoney [https://www.instagram.com/teacherswithmoney/] Instagram (Christa) → @christajeanjones [https://www.instagram.com/christajeanjones/] LinkedIn → Christa Jones [https://www.linkedin.com/in/christajeanjones/] Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab [https://christajones.samcart.com/products/tpt-launch-lab] This podcast is for educational and entertainment purposes only and does not constitute financial advice.

Teaching Abroad and Building a Side Hustle as a Financial Strategist — with Kennedi Crosby

Kennedi Crosby is a secondary math teacher with six years in the classroom, and a journey most teachers don't get to live. She has taught in New Orleans, Washington D.C., Kuwait, and now China. Somewhere along the way, she also became a financial strategist working specifically with teachers: walking them through the kind of financial education most of us never got. This episode moves through her winding path. From biochemistry pre-med at an HBCU, to teaching algebra in New Orleans. To the international classroom in Kuwait. Through the brutal reverse culture shock of coming home to the U.S. job market — over two hundred applications, less than ten interviews, a year and a half of stringing together seven jobs at once. And into her current dual life: math teacher in China + financial strategist for teachers stateside. Part travel story, part U.S. system reality check, part very practical money advice from someone who learned it the hard way. This episode covers: • Kennedi's path from biochemistry pre-med to math teacher  • What teaching internationally actually looks like — IB curriculum, 48-hour offer letter decisions, schools that start their hiring cycle in September, and the contract realities most U.S. teachers don't know about • The reverse culture shock of coming home: why returning to the U.S. job market after teaching abroad was harder than the original move • Seven jobs at once: tutoring, bartending, nannying, online teaching platforms, what a year and a half of stringing it all together actually looks like with no salary, no benefits, no safety net • How Kennedi became a financial strategist — a LinkedIn outreach from another educator that opened a new chapter of her teaching life • What a financial strategist actually does (a "thought partner" for your money) and what a first conversation with one looks like in practice • The generational money advice gap — why what worked for our parents and grandparents won't get you to retirement on a teacher's salary in 2026 • Pay yourself first: the one shift Kennedi most wants teachers to make next, and why it has to come before everything else 🍏 Heads up: this episode contains (very!) brief adult language. Tagged E for explicit. Connect with Kennedi: linkedin.com/in/kennedi-crosby [https://www.linkedin.com/in/kennedi-crosby-/] Kennedi Crosby works as a financial strategist with the Miliare Group. Always consult a licensed financial professional before making significant financial decisions. 🎧 Subscribe now for new episodes every Tuesday. Come hang: Instagram → @teacherswithmoney [https://www.instagram.com/teacherswithmoney/] Instagram (Christa) → @christajeanjones [https://www.instagram.com/christajeanjones/] LinkedIn → Christa Jones [https://www.linkedin.com/in/christajeanjones/] Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab [https://christajones.samcart.com/products/tpt-launch-lab] This podcast is for educational and entertainment purposes only and does not constitute financial advice.

From Credit Card Debt to Financial Confidence: An Educator's Story with Rose Mendonca of Teacher Talks Money

If you're a teacher carrying credit card debt right now — the kind that sits in your chest at 2am — this episode is for you. Rose Mendonca is a 26-year educator, school counselor, and the founder of Teacher Talks Money, a financial education platform built for teachers by a teacher. She climbed out of credit card debt on a teacher's salary, paid off her mortgage years ahead of schedule, and built her platform without ever leaving the classroom. Rose's story is the spine of this conversation. The credit card trap she fell into as a first-gen college student. The merged-household debt she and her husband carried into newlywed life. The five to seven years of consistency it took to get out. And the single habit that did the most heavy lifting: automation. Plus the three steps Rose teaches educators to go from a $36,000 salary to a million dollars, the number one retirement mistake she sees teachers make, and why she believes every teacher should open a Roth IRA — even while still in debt. This episode covers: • Rose's debt story: the credit card trap that started in college, the merged-household debt of early marriage, and the five to seven years of consistency it took to climb out • The first move that did the heavy lifting: automation, and the specific weekly cadence Rose used to turn $50 a paycheck into seven figures • Rose's counterintuitive take on debt vs. investing: why she tells every teacher (even those in serious debt) to open a Roth IRA and start funding it with $50, before clearing the credit card balance • The 403(b)/457 conversation: how to find what your district offers, the fee question that quietly costs teachers hundreds of thousands of dollars, and the bad actors to watch out for • The pension myth: why "my pension will cover it" is the number one retirement mistake Rose sees teachers make • Building Teacher Talks Money while staying inside education — proof that financial confidence doesn't require leaving the work you love 🍏 Books mentioned in this episode: Your Money or Your Life by Vicki Robin · Clever Girl Millionaire by Bola Sokunbi Connect with Rose: @teachertalksmoney [https://www.instagram.com/teachertalksmoney/] (Instagram) linkedin.com/in/rose-mendonca [https://www.linkedin.com/in/rose-mendonca] (LinkedIn) teachertalksmoney.com [https://teachertalksmoney.com] Rose Mendonca is the founder of Teacher Talks Money and offers financial education and coaching. Always consult a licensed financial professional before making significant financial decisions. 🎧 Subscribe now for new episodes every Tuesday. Come hang: Instagram → @teacherswithmoney [https://www.instagram.com/teacherswithmoney/] Instagram (Christa) → @christajeanjones [https://www.instagram.com/christajeanjones/] LinkedIn → Christa Jones [https://www.linkedin.com/in/christajeanjones/] Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab [https://christajones.samcart.com/products/tpt-launch-lab] This podcast is for educational and entertainment purposes only and does not constitute financial advice.