From Pies to Prosperity

Cooper
  • 5.0 (7)
  • INVESTING
  • UPDATED MONTHLY

Welcome to the “From Pies to Prosperity” Podcast. The show where we navigate life’s financial obstacles and learn the truths of personal finance, one slice at a time. If you’ve asked yourself, “why wasn’t I taught this growing up?”, well, you’ve come to the right place. Your host, pizza guru, and Certified Financial Planner, Cooper Casillas, is on a mission to educate others and inspire financial freedom. It’s more than advice, it’s peace of mind... and pizza!

  1. FPTP Episode 16: Tax Withholding

    07/25/2025

    FPTP Episode 16: Tax Withholding

    Are you unknowingly giving Uncle Sam thousands of dollars in interest-free loans each year? If you're like 70% of Americans who celebrate receiving a tax refund, you might be missing a crucial financial opportunity. Tax withholding—that mysterious process where money disappears from your paycheck before it even reaches your bank account—is rarely understood. But mastering this concept could put thousands of dollars back in your pocket throughout the year instead of waiting for a refund. Think of your tax obligation like filling a bathtub: you want it just right. Too much water (overwithholding) means you've loaned the government your money interest-free. Too little (underwithholding) means a painful bill in April. The key to perfect withholding lies in your W-4 form, which most people complete once when starting a job and promptly forget about. Major life events like marriage, having children, or buying a home should trigger a W-4 review. We also tackle common misconceptions about bonuses. Contrary to popular belief, bonuses aren't taxed higher than regular income—they're just subject to different withholding rules. For self-employed folks and contractors, we explore the importance of quarterly payments and dedicated tax savings accounts to avoid April surprises. Ready to stop giving Uncle Sam an interest-free loan? Listen now to learn how updating your tax withholding could be one of the simplest yet most effective financial moves you make this year. Subscribe for more financial insights that transform complicated money concepts into practical, actionable advice. This episode's pizza and score: Pizza Hut - https://www.pizzahut.com/deals?gclsrc=aw.ds&ds_rl=1149043&gad_source=1&gad_campaignid=122485240&gbraid=0AAAAADyJNr0l7T4I2Ob8ukhN5_aPac8wS&gclid=CjwKCAjw1ozEBhAdEiwAn9qbzaXTAPRiAcPY-mRDHHvfxLTs5MJ1xdnD_AlomiWkbro6jroX1Q5fIhoC4zQQAvD_BwE Cooper's Score: 6.4 Corinne's Score: 8.8 From Pie's to Prosperity is an educational podcast geared towards helping you navigate life's financial obstacles, one slice at a time. Hosted by Cooper Casillas, this podcast will feature special guests, industry professionals, and topic summaries to help simplify complex financial decisions. To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes Make sure to hit that subscribe button to keep up with episodes and subscribe to our YouTube channel below to stay up to date with all the things Cooper and his team are working on! Website: https://rayolson.net Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 This information provided is strictly for educational purposes only and does not constitute financial, investment, tax, or legal advice. Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. Ray Olson, LLC is not affiliated with Kestra IS Thank you for listening!

    40 min
  2. FPTP Episode 15: Evidence-based Investing!

    05/30/2025

    FPTP Episode 15: Evidence-based Investing!

    Investing can be confusing, especially when there are so many different options out there. In today's episode we try to demystify and explain what evidence-based investing is in comparison to the other strategies out there. Keep it simple, invest for the long term, tilt the odds into your favor, diversify, and you'll be well on your way to a successful investing journey! Evidence-based investing microsite: https://invest.focuspartners.com/ This episode's pizza and score: Homemade Picken! (chicken pizza) - https://basicswithbails.com/ingredients/chicken/chicken-crust-pizza/ Cooper's Score: 6.3 Corinne's Score: 9.0 for chicken pizza, 2.0 for actual pizza From Pie's to Prosperity is an educational podcast geared towards helping you navigate life's financial obstacles, one slice at a time. Hosted by Cooper Casillas, this podcast will feature special guests, industry professionals, and topic summaries to help simplify complex financial decisions. To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes Make sure to hit that subscribe button to keep up with episodes and subscribe to our YouTube channel below to stay up to date with all the things Cooper and his team are working on! Website: https://rayolson.net Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 This information provided is strictly for educational purposes only and does not constitute financial, investment, tax, or legal advice. Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. Ray Olson, LLC is not affiliated with Kestra IS Thank you for listening!

    39 min
  3. FPTP Episode 14: 401(k) Plans!

    04/09/2025

    FPTP Episode 14: 401(k) Plans!

    Make sure to listen to this month's episode and learn the in's and out's of 401(k) plans and why they are the most popular vehicle to successfully grow your wealth! This episode's pizza spot and score: Redemption BBQ in the West End - https://redemptionbbq.com/ Cooper's Score: 9.1 Corinne's Score: 9.0 From Pie's to Prosperity is an educational podcast geared towards helping you navigate life's financial obstacles, one slice at a time. Hosted by Cooper Casillas, this podcast will feature special guests, industry professionals, and topic summaries to help simplify complex financial decisions. To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes Make sure to hit that subscribe button to keep up with episodes and subscribe to our YouTube channel below to stay up to date with all the things Cooper and his team are working on! Website: https://rayolson.net Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 This information provided is strictly for educational purposes only and does not constitute financial, investment, tax, or legal advice. Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. Ray Olson, LLC is not affiliated with Kestra IS Thank you for listening!

    44 min
  4. We're Getting Married! (Why are Weddings so Expensive?)

    02/06/2025

    We're Getting Married! (Why are Weddings so Expensive?)

    Today's episode has little educational content but lot's of fun! We are officially engaged and wanted to share the story for you all to enjoy. We appreciate you and promise to get back into the educational format next month! This episode's Pizza spot and score: Fire & Hops Pizza in the Museum District  - https://fireandhopsrva.com/ Cooper's Score: 7.7 Corinne's Score: 6.8 From Pie's to Prosperity is an educational podcast geared towards helping you navigate life's financial obstacles, one slice at a time. Hosted by Cooper Casillas, this podcast will feature special guests, industry professionals, and topic summaries to help simplify complex financial decisions. To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes Make sure to hit that subscribe button to keep up with episodes and subscribe to our YouTube channel below to stay up to date with all the things Cooper and his team are working on! Website: https://rayolson.net Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 This information provided is strictly for educational purposes only and does not constitute financial, investment, tax, or legal advice. Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. Ray Olson, LLC is not affiliated with Kestra IS Thank you for listening!

    51 min
  5. The Psychology of Money! (continued)

    01/16/2025

    The Psychology of Money! (continued)

    You wanted more money psychology talk so you got it! In today's episode Cooper and Corinne dive into the fascinating psychology of money—how emotions, biases, and beliefs shape our financial decisions; learning practical strategies to build a healthier mindset around money and make more confident financial choices. We hope you enjoy this one! This episode's Pizza spot and score: Belmont Pizzeria in the Museum District  - https://belmontpizzeria.com Cooper's Score: 6.7 Corinne's Score: 8.0 From Pie's to Prosperity is an educational podcast geared towards helping you navigate life's financial obstacles, one slice at a time. Hosted by Cooper Casillas, this podcast will feature special guests, industry professionals, and topic summaries to help simplify complex financial decisions. To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes Make sure to hit that subscribe button to keep up with episodes and subscribe to our YouTube channel below to stay up to date with all the things Cooper and his team are working on! Website: https://rayolson.net Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 This information provided is strictly for educational purposes only and does not constitute financial, investment, tax, or legal advice. Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. Ray Olson, LLC is not affiliated with Kestra IS Thank you for listening!

    50 min
  6. FPTP: Episode 11 - Saving and the Psychology of Money!

    10/21/2024

    FPTP: Episode 11 - Saving and the Psychology of Money!

    The core principal of personal finance - saving and planning for the future. In today's episode Cooper and Corinne discuss why it's so important, how to get paid more on your savings, and even dive into the psychology of saving. We hope you enjoy this one! This episode's Pizza spot and score: Genova's Pizza Station in Bon Air  - https://www.genovaspizzastation.com Cooper's Score: 5.4 Corinne's Score: 4.8 Forrest's Score: 5.0 From Pie's to Prosperity is an educational podcast geared towards helping you navigate life's financial obstacles, one slice at a time. Hosted by Cooper Casillas, this podcast will feature special guests, industry professionals, and topic summaries to help simplify complex financial decisions. To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes Make sure to hit that subscribe button to keep up with episodes and subscribe to our YouTube channel below to stay up to date with all the things Cooper and his team are working on! Website: https://rayolson.net Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 This information provided is strictly for educational purposes only and does not constitute financial, investment, tax, or legal advice. Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. Ray Olson, LLC is not affiliated with Kestra IS Thank you for listening!

    41 min
  7. FPTP: Episode 10 - Traditional IRA's!

    10/02/2024

    FPTP: Episode 10 - Traditional IRA's!

    While Cooper may not be quite as passionate about the Traditional IRA compared the Roth IRA, it is still an incredibly powerful way to minimize your tax bill. Listen to this episode to learn more about the Traditional IRA and how it compares to the Roth IRA! This episode's Pizza spot and score: Sergios Italian in Midlothian  - https://sergiositalian.com Cooper's Score: 8.3 Corinne's Score: 8.8 From Pie's to Prosperity is an educational podcast geared towards helping you navigate life's financial obstacles, one slice at a time. Hosted by Cooper Casillas, this podcast will feature special guests, industry professionals, and topic summaries to help simplify complex financial decisions. To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes Make sure to hit that subscribe button to keep up with episodes and subscribe to our YouTube channel below to stay up to date with all the things Cooper and his team are working on! Website: https://rayolson.net Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 This information provided is strictly for educational purposes only and does not constitute financial, investment, tax, or legal advice. Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. Ray Olson, LLC is not affiliated with Kestra IS. Thank you for listening!

    36 min
  8. FPTP: Episode 9 - Roth IRA's!

    08/04/2024

    FPTP: Episode 9 - Roth IRA's!

    What's that I hear in the distance? Thunder? No! Earthquake? No! A Roth IRA you say? Yes! Oh the power!!! Listen to this month's episode to learn why the Roth IRA is Cooper's best friend when it comes to investing. This episode's Pizza spot and score: Mac Pizza & Wings  - https://www.macpizzawings.com/virginia Cooper's Score: 6.3 Corinne's Score: 7.6 From Pie's to Prosperity is an educational podcast geared towards helping you navigate life's financial obstacles, one slice at a time. Hosted by Cooper Casillas, this podcast will feature special guests, industry professionals, and topic summaries to help simplify complex financial decisions. To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes Make sure to hit that subscribe button to keep up with episodes and subscribe to our YouTube channel below to stay up to date with all the things Cooper and his team are working on! Website: https://rayolson.net Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 This information provided is strictly for educational purposes only and does not constitute financial, investment, tax, or legal advice. Securities offered through Kestra Investment Services, LLC (Kestra IS), member FINRA/SIPC. Investment advisory services offered through Kestra Advisory Services, LLC (Kestra AS), an affiliate of Kestra IS. Ray Olson, LLC is not affiliated with Kestra IS. Thank you for listening!

    36 min
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Ratings & Reviews

5
out of 5
7 Ratings

About

Welcome to the “From Pies to Prosperity” Podcast. The show where we navigate life’s financial obstacles and learn the truths of personal finance, one slice at a time. If you’ve asked yourself, “why wasn’t I taught this growing up?”, well, you’ve come to the right place. Your host, pizza guru, and Certified Financial Planner, Cooper Casillas, is on a mission to educate others and inspire financial freedom. It’s more than advice, it’s peace of mind... and pizza!

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