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)

Jenn Jamali (LinkedIn)

firstjennmoney.com

Newsletter — raw, real money stories + challenges

RICH Reset Roadmap Call with Jenn

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

Instagram (Christa) → @christajeanjones

LinkedIn → Christa Jones

Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab

This podcast is for educational and entertainment purposes only and does not constitute financial advice.

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!*

Connect with Bryson:

ThatMusicTeacher.com — for elementary music teachers

Tarbet Education Network — for arts specialists

@thatmusicteacher (Instagram)

Bryson Tarbet (LinkedIn)

*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

Instagram (Christa) → @christajeanjones

LinkedIn → Christa Jones

Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab

This podcast is for educational and entertainment purposes only and does not constitute financial advice.

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

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

Instagram (Christa) → @christajeanjones

LinkedIn → Christa Jones

Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab

This podcast is for educational and entertainment purposes only and does not constitute financial advice.

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 (Instagram)

linkedin.com/in/rose-mendonca (LinkedIn)

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

Instagram (Christa) → @christajeanjones

LinkedIn → Christa Jones

Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab

This podcast is for educational and entertainment purposes only and does not constitute financial advice.

If you're a teacher and you're tired — bone-deep, paycheck-to-paycheck tired — this episode opens with the sentence you need to hear: it's not your fault. The math hasn't been mathing for a long time. The system that's supposed to support the people who shape every future generation has been quietly underpaying you for decades.

And then it pivots. Christa names what most teachers have been told to keep quiet about: you were never supposed to be broke, wanting wealth doesn't make you ungrateful, and building a side income is not selling out. It's surviving. It's thriving. It's refusing to wait for the system to catch up.

This episode covers:

• The teacher pay gap by the actual numbers — 27% less in weekly wages than other professionals with comparable degrees, and the gap widening (not closing) over the last decade.

• The script teachers were handed and never asked for — "teachers don't do it for the money" as a personal ceiling on what you're allowed to want.

• Why side hustles aren't hustle culture — the difference between grinding yourself into burnout and building something on your own terms that gives you breathing room, choices, and a real safety net.

• The counterintuitive truth — a side hustle can give you energy BACK, not just take it. And for a lot of teachers, it's the thing that actually makes staying in the classroom sustainable.

• A first taste of what's coming on the show — real teachers building real income streams (TPT, tutoring, curriculum writing, coaching, consulting, content) without leaving the classroom they love.

🍏 If this hits home, share it with a teacher who needs to hear "it's not your fault" today. That's how this grows — teacher to teacher.

🎧 Subscribe now for new episodes every Tuesday.

Come hang:

Instagram → @teacherswithmoney

Instagram (Christa) → @christajeanjones

LinkedIn → Christa Jones

Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab

This podcast is for educational and entertainment purposes only and does not constitute financial advice.

Courtney Johnson is a career content creator, personal brand strategist, and the author of Career Cheat Codes. She's also Christa's personal brand mentor, business coach, and the person who helped her build the thing you're listening to right now. In this conversation: why teachers should work louder (not harder), and the smallest possible step toward building a personal brand.

Plus: cringe mountain, why receiving compliments is the same muscle as receiving money, and Courtney's exact starter pack for anyone who wants to start posting online but doesn't know where to begin.

This episode covers:

• The case for working louder: why staying visible matters more than staying late, and how teachers can practice it without feeling like they're bragging.

• Cringe mountain: the gap between where you are and where you want to be, and why everyone who's already up there had to climb it themselves.

• Career advice that actually translates for teachers: most of it assumes a corporate ladder. What the cheat codes look like when your path isn't a ladder.

• Receiving compliments → receiving money. Why one is the practice muscle for the other, and what teachers can do this week to start.

• The personal brand starter pack: pick one platform. Post one time a week. For one year. That's it.

Connect with Courtney:

@courtlynnjohnson (Instagram)

@courtlynnjohnson (TikTok)

Courtney Johnson (LinkedIn)

Career Cheat Codes (Penguin Random House)

🎧 Subscribe now for new episodes every Tuesday.

Come hang:

Instagram → @teacherswithmoney

Instagram (Christa) → @christajeanjones

LinkedIn → Christa Jones

Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab

This podcast is for educational and entertainment purposes only and does not constitute financial advice.

Davy Yap is a full-time middle school teacher in California. She's also on track to retire at 45 as a millionaire on a teacher's paycheck. As a teacher who got specific about money and made moves most teachers haven't been told they're allowed to make.

In this conversation, Davy walks through the actual plan: the high yield savings accounts that pay you 3-4% instead of 0.02%, the retirement accounts many teachers haven't opened, the earning streams she built outside the paycheck. And the mindset work that made all of it possible, including unlearning the “money is bad” wiring most of us absorbed without realizing.

This episode covers:

• Davy's path from default-saver to wealth-builder, and the specific moves teachers can copy

• High yield savings accounts (HYSA): what they are, why Chase and Bank of America are quietly costing you, where Davy keeps her money instead

• The reframe that lifts the entire ceiling: there's a cap to saving, no cap to earning

• Davy's three side income streams (focus groups, content + brand deals, digital products) and how she actually built each one, including the brand deal she landed at 4,000 followers and the one Instagram bio detail that unlocked it

• Money guilt for teachers who talk publicly about money: how Davy navigates the haters, the affirmations practice that rewired her thinking, and the book that started it all (Secrets of the Millionaire Mind by T. Harv Eker)

• Why being a great teacher and building wealth are not mutually exclusive

🍏 Millionaire Mind affirmations playlist (mentioned in this episode): Listen on Spotify

Connect with Davy:

Davy on Instagram

Davy on TikTok

Davy on Substack

🎧 Subscribe now for new episodes every Tuesday.

Come hang:

Instagram → @teacherswithmoney

Instagram (Christa) → @christajeanjones

LinkedIn → Christa Jones

Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab

This podcast is for educational and entertainment purposes only and does not constitute financial advice.

Christa waited ten years to open her Teachers Pay Teachers store. Ten years of “I’ll do it this summer” and “the market is probably too saturated.” Sound familiar? In this episode, she dismantles the three biggest lies keeping teachers from starting — and replaces them with frameworks you can actually use.

Plus: the Olipop vs. Coca-Cola strategy for finding your niche, the Liquid Death approach to standing out with style, why Cringe Mountain is the only path to the Land of Cool, and a 15-minute exercise you can do right now to find your first product hiding in your own files.

This episode covers:

• The originality myth: why “someone already made it” is not the reason you think it is (and what Steal Like an Artist taught Christa about good theft vs. bad theft)

• The saturation myth: two brand strategy frameworks (Olipop vs. Coca-Cola and Liquid Death) that show you exactly how to find your corner in a crowded market

• The time myth, Cringe Mountain, and the garden: the honest conversation about where your hours actually go, why waiting to feel ready is a trap, and the metaphor that takes the pressure off perfectionism

• The 15-minute resource hunt: a concrete exercise to find your first TPT product hiding in your Google Drive right now

🍏 FREE TPT Store Optimization Checklist

🎧 Subscribe now for new episodes every Tuesday.

Come hang:

Instagram → @teacherswithmoney

Instagram (Christa) → @christajeanjones

LinkedIn → Christa Jones

Let's finally start your Teachers Pay Teachers store, together! → TPT Launch Lab

This podcast is for educational and entertainment purposes only and does not constitute financial advice.