The Money Confident Podcast with Jillian Todd

Happy Hour with with Sabrina of Seriously Sabrina Photography: Building a Sustainable Creative Career

Welcome back to Happy Hour, the bonus series where Jillian sits down with fellow creative entrepreneurs for honest conversations about business, money, creativity, and building a life you actually enjoy.

In this episode, Jillian chats with photographer Sabrina of Seriously Sabrina Photography, a longtime wedding photographer whose career has evolved to include commercial photography, interiors, agricultural photography, and a full-time role at the University of Kentucky.

Together, they talk about what it looks like to grow beyond the business you first built, balancing multiple income streams, learning to invest as a self-employed creative, and why sometimes the biggest goal is finally enjoying the life you've created.

Inside This Episode

• How Sabrina built a photography business that's evolved far beyond weddings

• Why diversifying your income can create more flexibility and stability

• The realities of balancing self-employment with a full-time creative job

• Setting clear boundaries when new opportunities come your way

• How Jillian and Sabrina met through a creative business retreat and how that friendship eventually led to financial coaching

• What it felt like to start investing and saving for retirement as a self-employed creative

• Why financial confidence isn't about knowing everything—it's about having someone to help you navigate the next step

• The joy of missing out (JOMO) and learning to enjoy the business you've already built

One of Jillian's Favorite Takeaways

"Sometimes success isn't about chasing the next goal. Sometimes it's about realizing you've built a business that finally lets you breathe."

After years of working toward bigger milestones, Sabrina shares why she's intentionally embracing a season of stability, trusting the systems she's built and giving herself permission to simply enjoy them.

Connect with Sabrina

You can follow Sabrina's photography work on Instagram at @SeriouslySabrina, where she shares weddings, commercial photography, portraits, and creative projects.

You can also find her agriculture photography work through Craft and Calling, highlighting stories from farms, food, and the agricultural community.

Join Jillian at Happy Hour IRL

If you're an Atlanta-based creative entrepreneur, come join Jillian's monthly Happy Hour meetups! Grab a drink, meet other creatives, and chat about money, marketing, business, and all the beautifully messy parts of running a creative business.

Follow Jillian on Instagram for upcoming Happy Hour dates, and if there's a creative entrepreneur you'd love to hear on a future bonus episode, send her a DM!

The Money Confident Podcast with Jillian Todd

Episode 14: Why Group Coaching Is Better Than 1:1 

When you think about getting support with your finances, your first instinct might be to look for one-on-one coaching.

But what if the fastest path to financial confidence isn't going it alone?

In this episode, Jillian shares her hot take on why group coaching can be even more powerful than private coaching when it comes to reaching your biggest financial goals. From learning alongside other creatives to finding accountability, community, and fresh perspectives, she explains why the people sitting next to you might be just as valuable as the coach leading the room.

If you've ever wondered whether group coaching is "enough" support, this episode might just change your mind.

Inside This Episode, You'll Learn:

• Why community can accelerate your financial growth
• How group coaching creates a safe space to ask the questions you're afraid to ask
• Why hearing someone else's coaching often leads to your biggest breakthroughs
• The surprising advantages of learning from creatives in completely different industries
• How Jillian's first mastermind changed the way she thinks about coaching
• Why accountability feels different when you're working toward a goal alongside others
• The Pilates analogy that perfectly explains why group coaching works

Why Jillian Loves Group Coaching:

✔️ You don't have to figure everything out by yourself.

✔️ You learn from other creatives' experiences—not just your own.

✔️ You gain fresh ideas from people with different business models and perspectives.

✔️ You build relationships with people who understand what it's like to run a creative business.

✔️ You stay accountable because your community is cheering you on every step of the way.

Jillian's Favorite Reminder:

"Sometimes you don't need to hear it from your Money Mom—you need to hear it from someone who's walking the path right beside you."

Ready to Build Your Financial Goal Alongside Other Creatives?

Breadwinner is Jillian's 12-month group coaching program designed to help creative entrepreneurs set—and actually achieve—their biggest financial goals.

Whether you want to pay yourself more, build your savings, invest for retirement, or finally feel confident with your money, you'll do it with expert coaching and a community of creatives cheering you on every step of the way.

Learn more and apply at:👉 jilliantodd.com/breadwinner

Have questions about whether Breadwinner is the right fit? Send Jillian a DM on Instagram—she'd love to chat and help you decide if it's the right next step.

The Money Confident Podcast with Jillian Todd

Happy Hour with with Jeannene of Intentionally Tabled: Building a Values Based Business

Welcome to the very first Happy Hour bonus episode! 🍸

In this new series, Jillian sits down with fellow creative entrepreneurs for honest conversations about business, money, creativity, and the beautifully messy journey of building a life you actually love.

For the inaugural episode, Jillian is joined by wedding planner and creative community builder Jeannene, founder of Intentionally Tabled. Together, they chat about meeting at a retreat in the French countryside, finding your people as a creative entrepreneur, rebranding your business to better reflect your values, and why community can change everything.

It's like grabbing a drink with two creative business owners who can't stop talking shop—in the best way.

Inside This Episode, You'll Hear About:

• How Jillian and Jeannene met while attending a creative retreat in France
• Why creative community is so important when running a solo business
• The story behind Jeannene's rebrand from Jeannene Lillie Events to Intentionally Tabled
• How leading with your values can transform your business (and make marketing feel more authentic)
• Why separating yourself from your business can create healthier boundaries
• The role that mentorship and creative friendships play in business growth
• A behind-the-scenes look at Jillian's wedding planning experience and why shared values mattered more than aesthetics
• How honoring clients' privacy and experiences can become part of your brand values

One of Jillian's Favorite Moments:

"Sometimes the people in your community can see something in you before you can see it yourself."

Whether it's a business rebrand, a new offer, or simply taking the next brave step, this conversation is a beautiful reminder that you don't have to build your business alone.

Connect with Jeannene:

Learn more about Jeannene's wedding planning business, Intentionally Tabled, and her Creative Collective events designed to bring creative entrepreneurs together for intentional connection and community.

Want to Join Jillian in Person?

If you're an Atlanta-based creative entrepreneur, don't miss Jillian's monthly Happy Hour meetups! Grab a drink, meet other creatives, and chat about money, marketing, business, and everything in between. Follow Jillian on Instagram for upcoming dates and details.

Have someone you'd love to hear on a future Happy Hour episode? Send Jillian a DM—she'd love to hear your ideas!

The Money Confident Podcast with Jillian Todd

Episode 13: Real Breadwinner Success Stories: Retirement, Cash Flow & Big Life Goals

What does financial confidence actually look like?

In this episode, Jillian is taking her mentor's advice and bragging a little—in the best way possible. She shares three real client stories from inside Breadwinner to show what happens when creatives stop running their money on vibes and start building a financial plan that supports the life they actually want.

Whether you're feeling behind on retirement, stuck on the cash flow rollercoaster, or simply know you could be more strategic with your money, these stories will help you see what's possible.

Featured Success Stories:

✔️ Client S: Went from $1,500 invested to $25,000 invested while creating a retirement strategy that also reduced her tax bill

✔️ Client T: Escaped the cash flow rollercoaster and successfully made it through the slow season without using credit cards

✔️ Client J: Went from "running my business on vibes" to creating a strategic financial plan that gave her the confidence to pursue a move and grow her family

Jillian's Favorite Reminder:

"Sometimes you don't need a rags-to-riches story. You just need to know that someone like you has done the thing you're hoping to do."

Thinking About Breadwinner?

If you're ready to feel more strategic, more confident, and more powerful with your finances, Breadwinner is currently open for enrollment.

Inside, you'll build a financial plan that works for your life, your business, and your brain—with support every step of the way.

Apply Now

Have a big financial goal but aren't sure how to get there?

Every application comes directly to Jillian. You can text with her, ask questions, or schedule a free call to talk through what's going on in your business and how she can help.

Got questions? Send Jillian a DM on Instagram @_jilliantodd. She'd love to hear from you.

The Money Confident Podcast with Jillian Todd

Episode 12: Financial Planning for Artists

When most people hear "financial planning," they picture spreadsheets, retirement calculators, and people with traditional 9-to-5 jobs.

But what does financial planning look like when you're an artist, creative, or small business owner with inconsistent income?

In this episode, Jillian breaks down the six essential areas every creative needs to understand to build a sustainable, profitable business and create long-term financial stability without giving up the work they love. Whether you're currently "checking your bank account and vibing" or you're ready to get more strategic with your money, this episode will help you take the next step.

Inside This Episode, You'll Learn:

• How to manage inconsistent income with a simple cash flow planning system
• Why understanding your pricing is the key to building a profitable business
• The biggest tax mistake creatives make (and how to avoid it)
• How retirement planning actually works when you're self-employed
• Why your money mindset may be impacting your financial results more than you realize
• How to use your financial data to grow your business intentionally and sustainably

Jillian's Favorite Reminder:

"You don't have to choose between being creative and being financially secure. You can build a life you love using your art, your creativity, and your gifts while also creating stability, peace of mind, and a plan for the future."

Want More Support?

Breadwinner is Jillian's 12-month group coaching program designed to help creatives build money confidence, pay themselves well, and create a sustainable business that supports the life they want.

Learn more at:👉 jilliantoddcoaching.com/breadwinner

If this episode resonated with you, send Jillian a DM on Instagram @_jilliantodd and let her know what stood out most.

The Money Confident Podcast with Jillian Todd

Episode 11: Pay Yourself More Without Earning More (Webinar Replay)

You’re making money in your business… but somehow not feeling paid?

In this replay of Jillian’s live training, she breaks down exactly how creatives can pay themselves more—without taking on more clients, working more hours, or burning out.

If your income feels inconsistent, your savings feel confusing, or you’re just “checking your bank account and vibing”… this episode will give you a real plan.

Inside This Episode, You’ll Learn:

• Why earning more doesn’t automatically mean taking home more

• The 3-step framework to pay yourself more without increasing revenue

• How to predict your income (even if it feels inconsistent)

• Why raising your prices isn’t just about money—it’s about your life

• The truth about saving too much (and why it might be holding you back)

• How to stop avoiding your numbers and actually feel confident with them

The 3 Steps Jillian Teaches:

✔️ Predict your income so you can trust what’s coming in

✔️ Keep more of what you earn by focusing on profit (not just revenue)

✔️ Save less (strategically) so you can actually enjoy your money

Real Client Wins from This Episode:

✔️ A seasonal business owner who turned 4 months of income into year-round stability

✔️ A photographer who raised her prices, worked less, and paid herself more

✔️ An author who stopped hoarding money and started spending in alignment with her values

Jillian’s Favorite Reminder: “You don’t need to hustle harder to feel financially secure. You just need a plan—and the confidence to trust yourself with money.”

Want Support With This?

Jillian’s 12-month program, Breadwinner, walks you through this work step-by-step—so you can build real money confidence (not just more income).

Doors are open April 6th - 30th. Apply now: 👉 jilliantoddcoaching.com/breadwinner

Got questions? DM Jillian on Instagram—she’d love to help you figure out your next step 💛

The Money Confident Podcast with Jillian Todd

Episode 10: You Just Became a Breadwinner… Now What?

So you joined Breadwinner (or you’re this close to signing up)… but you’re wondering: what actually happens after you enroll?

In this episode, Jillian gives you a peek behind the scenes of what your year inside Breadwinner will really look like. From onboarding to coaching calls to getting the support you need when life throws a money curveball, this episode is your roadmap for what’s ahead.

Inside This Episode, You’ll Learn:

• What happens the moment you join Breadwinner (spoiler: no waiting around)

• Why Jillian offers a bonus 1:1 call for waitlist signups and what you can use it for

• How monthly coaching calls + co-working “Get Sh*t Done” sessions help you take action in real time

• What the on-demand training library includes,  from cash flow workshops to retirement planning guides and more 

• Why you’ll never feel lost in the group chat (hint: there’s a warm welcome waiting!)

  How quarterly 1:1 calls give you custom support all year long

Here’s What You’ll Get When You Join:

✔️ Bonus 1:1 onboarding call (if you join from the waitlist)✔️ Immediate access to all trainings 

✔️ One-click Google Calendar sync for all Breadwinner calls

✔️ Access to Jillian via Voxer M–F for questions between sessions

✔️ Monthly coaching calls focused on real-world money strategy

✔️ Monthly Get Sh*t Done calls to finally knock out that financial to-do list

✔️ Quarterly private Zoom calls with Jillian to go deep on your goals

Jillian’s Favorite Part:

“You don’t have to figure everything out in 6 weeks. Inside Breadwinner, you’ve got support all year long — when big wins happen, when hard stuff comes up, or when new questions arise. I’m here for all of it.”

Ready to Join Breadwinner?

Doors open again soon. Join the waitlist now to lock in your bonus 1:1 call and be first to know when enrollment begins:

👉 jilliantoddcoaching.com/breadwinner

Got questions? Slide into Jillian’s DMs on Instagram! She’d love to chat and help you decide if it’s the right fit.

The Money Confident Podcast with Jillian Todd

Episode 09: Stop Saying You Hate Taxes — Here’s What to Do Instead

If you’ve ever muttered “I hate taxes” under your breath (or screamed it into the void), this one’s for you.

In this empowering, no-nonsense episode, Jillian gives you a Money Mom butt-kick to stop spiraling about taxes and start taking back control. Because avoiding your tax strategy doesn’t protect you, it just keeps you from building wealth.

In This Episode, Jillian Breaks Down:

• Why saying “I hate taxes” keeps you in victim mode, and what to do instead

• What a write-off actually is (Schitt’s Creek fans, you’ll appreciate this)

• How to stop guessing and start getting the deductions you actually deserve

• Her favorite tax-saving moves for creative business owners (from S-Corps to retirement accounts)

• What to do if you’ve been letting tax stress simmer in the background all year

Tax Tools Jillian Recommends:

✅ Get all the write-offs you deserve by staying on top of your bookkeeping

✅ Know your retirement options (yes, even if you’re self-employed)

✅ Explore your eligibility for S-Corp election

✅ Hire your kids, donate to causes you care about, and contribute to your future — all while reducing your tax burden

Upcoming: QuickBooks for Creatives Workshop

🧾 Live co-working session in March (with coffee + croissants, virtually!)

📚 Access to all trainings ahead of time

🧠 Get unstuck live — Jillian will help troubleshoot your QuickBooks with you

🗓️ Doors open Feb 23, 2026

🎧 DM Jillian @_jilliantodd to say “heard it on the pod” and get an early bird discount

Jillian’s Reminder:

“Stop giving the government more money than they deserve — especially when you could be using it to support your family, your future, and your financial freedom.”

Have tax Qs or want to build your own custom strategy? DM Jillian or inquire via her site! She’s happy to help you make a plan that actually supports your life and your business.

🎙️ The Money Confident Podcast with Jillian Todd Episode 08: Tax Strategies for Creative Business : S-Corp vs. LLC 

You've probably heard the buzz: "Become an S-Corp and save thousands on taxes!" But is it really worth it for your creative business?

In this episode, Jillian breaks down what most accountants, Instagram tax influencers, and financial bros won’t tell you — the real pros, cons, and math behind filing as an S-Corp vs. staying an LLC (or sole proprietor).

By the end, you’ll know whether this move belongs on your to-do list or if it’s time to scratch it off for good. ✨

💼 In This Episode, You’ll Learn:

• The difference between an LLC, S-Corp, and sole proprietorship (and how each affects your taxes)

• What self-employment taxes actually are — and how S-Corp status helps reduce them

• Why “putting yourself on payroll” is required for S-Corps (and how to do it right)

• How to determine a “reasonable salary” (and why the IRS cares)

• Plus a Jillian walks through a real client example: how one photographer gave herself a $10k raise without paying more tax

🔎 Not Sure If This Is For You?

Download Jillian’s S-Corp vs. LLC Calculator

Plug in your revenue, expenses, and salary to see if switching to an S-Corp makes sense for your business.

🧾 Jillian's Reminder:

“An S-Corp can absolutely save you money, but only if your business is ready for it — and you're managing it correctly.”

📬 Want Personalized Support?

DM Jillian on Instagram @_jilliantodd with your numbers or questions — she loves helping creative business owners get clarity on this stuff.

🎙️ The Money Confident Podcast with Jillian Todd Episode 07: The Magic of Get Sh*t Done Calls

Have you ever had something on your to-do list for way too long? Like:

⏳ Opening your Roth IRA

📊 Finally catching up on bookkeeping

📬 Sending that price increase email

🧾 Paying your quarterly taxes

In this episode, Jillian shares one of the most powerful tools inside her signature program, Breadwinner, the Get Sh*t Done Calls, and why they’re the secret weapon for actually following through on the money tasks you keep avoiding.

💡 In This Episode, You’ll Learn:

• ​What a Get Sh*t Done call actually is — and how they’re different from normal coaching or accountability
• ​Why even financially savvy creatives still procrastinate the “scary” money tasks
• ​How body doubling and community support can radically shift your momentum

Actual Tasks Breadwinner Clients Have Completed on GSD Calls:

• ​Gotten caught up on months of bookkeeping
• ​Filed their own taxes with Jillian’s support
• ​Sent scary client emails (price raises, renewals, etc.)
• ​Reworked their entire pricing strategy using Jillian’s profitability tool
• ​Paid their quarterly taxes on time
• ​Opened and funded retirement accounts (Roth IRA, SEP IRA, etc.)
• ​Mapped out new offers and launched them on the spot
• ​Set up consistent salaries and automated transfers

💬 Jillian’s Take:

“It’s not just about giving you the plan. It’s about helping you implement it. These calls are baby steps toward full money confidence.”

Breadwinner isn’t just about learning what to do — it’s about actually doing it with expert support and an encouraging community. The GSD calls are a standout part of what makes this program so unique and successful.

Want in? Doors to Breadwinner open again soon. Head to jilliantoddcoaching.com/breadwinner to get on the waitlist or apply!

DM Jillian on Instagram @_jilliantodd  to let her know which task you’ve been procrastinating (and want to knock out on the next Get Sh*t Done call)!