Journey To Launch

Latest Episodes:

Episode 432: Creating a Future of Flexibility & Financial Security with Jackie Kasper Jun 25, 2025

Show notes

This week on the Journey to Launch podcast, I'm joined by Jackie Kasper, a fellow Journeyer who's intentionally building a life of connection and financial freedom. Jackie is a mom of two, a director of operations at a Chicago-based fintech startup, and someone who's actively pursuing Financial Independence (FI) within the next 2–7 years.

We also dive into how she and her husband are navigating the journey together (even if they're not always on the same financial page), the influence of motherhood on her long-term goals, and what reaching Coast FI means for her family's options and freedom.

In this episode, Jackie opens up about:

How she got into the FI movement after being introduced by her sister-in-law
The mindset and financial shifts she made to go from spending freely to strategically investing
Buying her first multi-unit property with her brother at 25 and how real estate plays into her FI goals + much more.0

Other Links Mentioned in episode:

Apply to Share Your Journeyer Story here.
Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
Get your copy of my book: Your Journey To Financial Freedom!
Join The Weekly Newsletter List to get updates, deals & more!
Leave Your Journey To Financial Freedom a review!
Get The Budget Bootcamp
Check out my personal website here.
Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!

Connect with me:

Episode 431: Die with Zero & Get All You Can From Your Money and Your Life w/ Bill Perkins REWIND Jun 18, 2025

Show notes

Bill Perkins, author and founder, managing partner and head trader for Skylar Capital, joins the podcast to discuss how to live your best life no matter your income and his two decades of experience in the trading industry.

We talk about the importance of balancing your financial goals with your time-appropriate life experiences and adding joy in your life right now while being intentional with what you want to do.

Bill's book, "Die With Zero," has been featured in The New York Times, Mr. Money Mustache, Success, and more.

In this episode we discuss:

How to enjoy your money and time now, instead of restricting yourself to the point of robbing you of your life
Balancing optimizing your life to fulfillment and saving for the future
Why certain experiences are useless for us at a certain point if we don't use them
Confronting fear-based mindsets by identifying goals
Why waiting until we die to give our children a financial foundation doesn't make sense + more

Other Links Mentioned in episode:

DiewithZero.com/welcome
Apply to Share Your Journeyer Story here.
Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
Get your copy of my book: Your Journey To Financial Freedom!
Join The Weekly Newsletter List to get updates, deals & more!
Leave Your Journey To Financial Freedom a review!
Get The Budget Bootcamp
Check out my personal website here.
Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!

Connect with Bill:

Connect with me:

Episode 430: How Christina Pivoted Careers, Tripled Her Income & Is Now on Track for Financial Independence with a $1.5M Goal Jun 11, 2025

Show notes

This week on the Journey to Launch Podcast, I'm speaking to fellow Journeyer, Christina Cates, a pediatric surgery physician assistant in Florida who pivoted from her career as a dietitian to triple her income and build a path toward financial independence (FI). Christina first discovered the FI movement through the Journey to Launch podcast and went all in—educating herself, shifting her money mindset, and making bold career moves, including negotiating her salary multiple times.

At age 35, she went back to school to become a physician assistant, all while managing ADHD, tackling debt, and staying committed to her long-term financial goals. She shares her journey from paycheck-to-paycheck struggles to becoming a confident investor with a plan to reach a $1.5 million FI number—all while enjoying the ride.

If you've ever wondered whether it's "too late" to make a change or if you're stuck in a low-paying field, Christina's story will inspire you to rethink what's possible.

In this episode we discuss:

Why Christina pivoted careers at age 35 and how she chose the PA path
How she negotiated her salary increases (and why it paid off—literally)
Balancing student loan debt with investing + her timeline to FI
Why mindset, not age, is the biggest barrier to change

Other Links Mentioned in episode:

Apply to Share Your Journeyer Story here.
Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
Get your copy of my book: Your Journey To Financial Freedom!
Join The Weekly Newsletter List to get updates, deals & more!
Leave Your Journey To Financial Freedom a review!
Get The Budget Bootcamp
Check out my personal website here.
Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!

Connect with Christina:

Instagram:@Rosie_d108

Connect with me:

Episode 429- How to Learn Less, Do More & Avoid Burnout on the Path to Financial Freedom w/ Pat Flynn Jun 04, 2025

Show notes

This week on the Journey to Launch podcast, I'm joined by Pat Flynn—digital entrepreneur, founder of Smart Passive Income, creator of Deep Pocket Monster, and author of Lean Learning: How to Achieve More by Learning Less. Pat shares how getting laid off from his dream job led to building a thriving online business, and how he's stayed grounded while growing multiple ventures across podcasting, YouTube, community building, and even Pokémon.

We explore the benefits of learning less, how to manage growth without losing yourself, what it takes to trust others in your business, and how to keep things fun while building a life aligned with your values.

In this episode we discuss:

How a $19.99 PDF launched Pat's entrepreneurial career

The mindset shift that helped him avoid burnout and delegate effectively

Strategies to decide if an idea should be monetized or kept as a hobby

What it means to build a business that truly fits the season of life you're in

Why reflection, experimentation, and service are key to sustainable growth

Check out the video to this episode on YouTube here: youtube.com/journeytolaunch

Other Links Mentioned in episode:

Check out Pat's book, Lean Learning: How to Achieve More By Learning Less
Listen to Pat's previous episode on the Journey to Launch Podcast, Building a Community, Using Entrepreneurship to Build Personal Wealth & Scaling a Business
Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
Get your copy of my book: Your Journey To Financial Freedom!
Join The Weekly Newsletter List to get updates, deals & more!
Leave Your Journey To Financial Freedom a review!
Get The Budget Bootcamp
Check out my personal website here.
Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!

Connect with Pat Flynn:

Connect with me:

Episode 428: Student Loans in 2025: What You Need to Know Now with Travis Hornsby May 28, 2025

Show notes

In this episode of Journey to Launch, I'm joined once again by Travis Hornsby, founder of Student Loan Planner. Travis returns to break down the current state of student loans, including what's changed under the Biden and Trump administrations, what borrowers should expect moving forward, and how to navigate the uncertainty with smart, strategic planning. Whether you're a recent grad or have six-figure student debt, this episode will help you better understand your options and next steps.

What You'll Learn in This Episode:

What happened to Biden's student loan forgiveness and SAVE Plan—and why they're essentially dead
How the IDR account adjustment and PSLF waiver may still benefit you
What the new GOP proposals could mean for repayment plans and forgiveness timelines
The difference between public vs. private student loans—and strategies for managing each
Why many borrowers should consider enrolling in an Income-Driven Repayment (IDR) plan now

Check out the video to this episode on YouTube here.

Other Links Mentioned in episode:

Book Your Custom Student Loan Plan at Student Loan Planner, here.
Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
Get your copy of my book: Your Journey To Financial Freedom!
Join The Weekly Newsletter List to get updates, deals & more!
Leave Your Journey To Financial Freedom a review!
Get The Budget Bootcamp
Check out my personal website here.
Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!

Connect with Travis Hornsby:

Connect with me:

Episode 427: The Long Game of Wealth Building & Staying the Course with JL Collins May 21, 2025

Show notes

This week on the Journey to Launch Podcast, I'm excited to welcome back the often called "Godfather of Financial Independence", JL Collins, author of the bestselling book The Simple Path to Wealth. In this episode, we dive into how to stay calm and confident in today's unpredictable market and why keeping it simple is still the most effective path to building real wealth. We also discuss the timeless power of index fund investing, how to approach investing at different stages of your journey, and why avoiding debt and living below your means are the most powerful tools for building financial freedom.

In this episode you'll learn:

The 3 core principles of The Simple Path to Wealth and why they haven't changed
What to do (and not do) during market downturns and volatility
How to approach financial advisors, and when they might actually hurt more than help
What's new in the updated edition of The Simple Path to Wealth + much more!

Check out the video to this episode on YouTube here.

The next FIRE LIVE class is on May 22nd! Get the FIRE Calc tool and save your spot for the class here. A walkthrough of the tool is available here as well.

Other Links Mentioned in episode:

Check out JL's book, The Simple Path to Wealth here.
Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
Get your copy of my book: Your Journey To Financial Freedom!
Join The Weekly Newsletter List to get updates, deals & more!
Leave Your Journey To Financial Freedom a review!
Get The Budget Bootcamp
Check out my personal website here.
Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!

Connect with JL Collins:

Connect with me:

Episode 426: The Ambition Trap — How to Stop Chasing & Start Living with Amina AlTai May 14, 2025

Show notes

This week on the Journey to Launch Podcast, I am sharing a powerful conversation I had with Amina AlTai—holistic leadership coach, chronic illness advocate and author of The Ambition Trap: How to Stop Chasing and Start Living - to unpack the truths behind ambition, burnout, and redefining success. We explore the emotional and cultural roots of ambition, especially for historically excluded groups, and why the traditional definition of success is no longer serving us. This is a must-listen if you're under the pressure to "do more" while wondering if there's a better, more sustainable way to grow and thrive.

In this episode, we discuss:

The difference between painful ambition and purposeful ambition
How core emotional wounds (rejection, betrayal, etc.) shape your drive and work habits
Why ambition doesn't always have to be tied to work or productivity
Navigating the ambition penalty in the workplace and reclaiming space

Check out the video to this episode on YouTube here: youtube.com/journeytolaunch

Other Links Mentioned in episode:

Check out Amina's book, The Ambition Trap: How to Stop Chasing and Start Living
Get the FIRE Calc Tool and join us for the next live class here.
Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
Get your copy of my book: Your Journey To Financial Freedom!
Join The Weekly Newsletter List to get updates, deals & more!
Leave Your Journey To Financial Freedom a review!
Get The Budget Bootcamp
Check out my personal website here.
Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!

Connect with Amina:

Connect with me:

Episode 425- Looking Back On My Early Retirement Dream- My Vision Then vs My Reality Now May 07, 2025

Show notes

In this solo episode, I'm revisiting a blog post I wrote eight years ago—one where I boldly declared that I wanted to retire by 40. You'll hear me read the post out loud and reflect on what actually came true, what's changed since then, and the parts I didn't expect.

If you've ever thought about what your life could look like beyond the 9–5 or you're just starting to dream about a different path, remember that it's okay for your definition of success to evolve—and that you're never too late to start.

In This Episode, I Share:

The blog post I wrote when I first dreamed of retiring early and what I actually made happen—like quitting my job and turning Journey to Launch into a business
How my view of retirement has shifted and what I didn't expect emotionally and mentally about entrepreneurship
Why I've become more flexible with money and life goals over time
How I used my FIRE Calculator to model my exit strategy—before I felt "fully ready"

Other Links Mentioned in episode:

Read my early retirement goals blog post here: journeytolaunch.com/blog/my-early-retirement-goals
Get the FIRE Calc Tool and join us for the next LIVE class here.
Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
Get your copy of my book: Your Journey To Financial Freedom!
Join The Weekly Newsletter List to get updates, deals & more!
Leave Your Journey To Financial Freedom a review!
Get The Budget Bootcamp
Check out my personal website here.
Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!

Connect with me:

Episode 424: Listener Q&A - Overcoming Investing Fears, Dealing w/ Inconsistent Income, Can You Coast to FI? + More Apr 30, 2025

Show notes

In this solo Q&A episode, I answer your top questions around investing, financial independence, and managing money through the ups and downs of real life. From overcoming investing fears to navigating inconsistent income, I share personal insights and strategies that have helped me make progress on the path to financial freedom.

You'll hear my thoughts on balancing debt payoff with investing, how to approach FIRE with an average income, and why mindset plays a bigger role than many realize.

In this episode, I share:

How you can start investing even when it feels overwhelming & one money habit that changed everything

Thoughts on Coast FI and Barista FI for parents or part-time workers plus is FIRE in high-cost cities like NYC or LA possible?

Ways to calculate your FIRE number even when your future feels uncertain, and how to factor pensions and Social Security into your long-term plan.
How to rewire limiting money beliefs from your upbringing and how to stay motivated when your progress feels slow

Other Links Mentioned in episode:

Get the FIRE Calc Tool For Yourself Here.
Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
Get your copy of my book: Your Journey To Financial Freedom!
Join The Weekly Newsletter List to get updates, deals & more!
Leave Your Journey To Financial Freedom a review!
Get The Budget Bootcamp
Check out my personal website here.
Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!

Connect with me:

Episode 423- Sisterhood, Entrepreneurship & Giving Yourself Grace: An Updated Convo w/ My Sisters Imani & Shaina Apr 23, 2025

Show notes

In this special crossover episode, originally recorded for the Brown Ambition Podcast, Mandy Woodruff-Santos sits down with me and my sisters—Shaina McGregor and Imani Manning—for an honest conversation about our individual and shared journeys. We dive deep into our unique paths in entrepreneurship, wellness, and culinary arts. From Jamaica to New York and everywhere in between, this episode explores family dynamics, building dreams, overcoming self-doubt, redefining success on your own terms and so much more!

In this episode, we share:

How sisterhood shaped our paths in entrepreneurship, wellness, and culinary arts
Shayna's pivot from dance to wellness coaching and social work
Imani's journey as a chef—feeding kids gourmet meals while growing her catering biz
Real talk on money, mindset, imposter syndrome, and giving yourself grace along the way

Other Links Mentioned in episode:

Check out the Brown Ambition Podcast here.
Get the FIRE Calc Tool For Yourself Here.
Join the Journey to Launch Book Club to dive deeper into financial freedom with guided discussions and resources here!
Get your copy of my book: Your Journey To Financial Freedom!
Join The Weekly Newsletter List to get updates, deals & more!
Leave Your Journey To Financial Freedom a review!
Get The Budget Bootcamp
Check out my personal website here.
Leave me a voicemail– Leave me a question on the Journey To Launch voicemail and have it answered on the podcast!
YNAB – Start managing your money and budgeting so that you can reach your financial dreams. Sign up for a free 34 days trial of YNAB, my go-to budgeting app by using my referral link.
What stage of the financial journey are you on? Are you working on financial stability or work flexibility? Find out with this free assessment and get a curated list of the 10 next best episodes for you to listen to depending on your stage. Check it out here!

Connect with me:

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