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.