- 17
- Episodes
- 11
- Ratings
- 2023
- First episode
- 23K
- YouTube views
About From Pies to Prosperity
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!
- Publisher
- Cooper
- Category
- business
- Language
- en
- Explicit
- No
- First episode
- 15 Sept 2023
- Latest episode
- 25 Jul 2025
Latest episodes
17 episodes in the feed.
25 Jul 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. Thi...
30 May 2025
FPTP Episode 15: Evidence-based Investing!
Industry experts demystify evidence-based investing strategies, explaining how diversification and long-term perspectives contribute to a successful investing journey.
9 Apr 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 spec...
6 Feb 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 obstacl...
16 Jan 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.comCooper's Score: 6.7Corinne's Score: 8.0Fro...
21 Oct 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.comCooper's Score: 5.4Corinne's Score: 4.8Forrest's Score: 5.0From Pie's to Prosperity is an educational podcast geared towards hel...
2 Oct 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.comCooper's Score: 8.3Corinne's Score: 8.8From Pie's to Prosperity is an educational podcast geared towards helping you navigate life's financ...
4 Aug 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/virginiaCooper's Score: 6.3Corinne's Score: 7.6From Pie's to Prosperity is an educational podcast geared towards helping you navigate life's financial obstacles, one slice at a time. Hos...
8 Jul 2024
FPTP: Episode 8 - Financial Considerations When Buying a House
The housing market has been a hot topic the last few years. For those considering jumping off the deep end, it is increasingly more important to go into the process in a strong financial position. In this episode, Cooper and Corinne discuss the nitty gritty of the financial details revolving around buying your first home. You can find more information on Virginia's down payment assistance grant here: https://www.virginiahousing.com/en/homebuyers/down-payment-assistance-grant (https://www.virginiahousing.com/en/homebuyers/down-payment-assistance-grant) This episode's Pizza spot and score: Angelo's Italian Restaurant - https://angelosmidlo.com (https://angelosmidlo.com) Cooper's Score: 7.6 Corinne's Score: 8.0 (https://www.jamesnay.com/) 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 (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 (https://rayolson.net/) Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 (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.
30 May 2024
FPTP: Episode 7- Working with a Realtor
The housing market has been a hot topic the last few years. For those considering jumping off the deep end, we thought it might be helpful to hear our story and hopefully learn from our experience and mistakes! This episodes Pizza spot and score: Sparrow's Pizza - https://sparrowspizza.com (https://sparrowspizza.com) Cooper's Score: 5.9 Corinne's Score: 5.5 James Nay @ James Nay Real Estate https://www.jamesnay.com (https://www.jamesnay.com)(804) 704-1944 (https://www.jamesnay.com) 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 (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 (https://rayolson.net/) Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 (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.
8 May 2024
FPTP: Episode 6 - Buying Our First Home
The housing market has been a hot topic the last few years. For those considering jumping off the deep end, we thought it might be helpful to hear our story and hopefully learn from our experience and mistakes! This episodes Pizza spot and score: California Pizza Kitchen - (https://zorchpizza.com/)https://www.cpk.com/ (https://www.cpk.com/) Cooper's Score: 5.6 Corinne's Score: 6.5 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 (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 (https://rayolson.net/) Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 (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.
6 Mar 2024
FPTP: Episode 5 - Taxes 101
With tax filing season upon us, we thought it might be helpful to walk you through the basics of taxes and why they are important for us to live our daily lives. Take a listen and learn how Corinne relates taxes to scoops of ice cream. This episodes Pizza spot and score: Zorch Pizza in Carytown - https://zorchpizza.com (https://zorchpizza.com) Cooper's Score: 6.8 Corinne's Score: 4.0 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 (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 (https://rayolson.net/) Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 (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.
9 Jan 2024
FPTP: Episode 4 - Budgeting!
The dreaded B-word... but... is it really that bad? Listen and learn how to use it as an empowering tool to accomplish your goals and not a dreaded, restrictive obligation. With the new year here, I challenge you to stick with it in 2024 and I promise you'll thank yourself down the road. Make it fun, make it exciting, make it color coordinated! You got this!! My personal budget spreadsheet: https://docs.google.com/spreadsheets/d/1xTmfxZyes4-yIvXntPI1wP3UuJH3zOukAVfCOqvFNXc/copy?usp=sharing (https://docs.google.com/spreadsheets/d/1xTmfxZyes4-yIvXntPI1wP3UuJH3zOukAVfCOqvFNXc/copy?usp=sharing) Video tutorial on how to use the spreadsheet: https://www.youtube.com/watch?v=uZuTmcvJk9M&t=1s (https://www.youtube.com/watch?v=uZuTmcvJk9M&t=1s) Popular online budgeting tools: Rocket Money: https://www.rocketmoney.com (https://www.rocketmoney.com) YNAB (You Need a Budget): https://www.ynab.com (https://www.ynab.com) Monarch: https://www.monarchmoney.com (https://www.monarchmoney.com) 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 (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 (https://rayolson.net) Email: cooper@rayolson.net Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 (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.
17 Nov 2023
FPTP: Episode 3 - Credit Cards
What are credit cards and credit scores and why should you take them seriously? Listen to this episode and learn how to work within the system and build your credit! The most traditional/formal way to check your credit is by creating an account at https://www.annualcreditreport.com (https://www.annualcreditreport.com/) and accessing each credit report. You can get this for free each year. Alternatively you can sign up with credit karma here: https://www.creditkarma.com Freeze your credit with the following links: Transunion: https://www.transunion.com/credit-freeze (https://www.transunion.com/credit-freeze) Equifax: https://www.equifax.com/personal/credit-report-services/credit-freeze/ (https://www.equifax.com/personal/credit-report-services/credit-freeze/) Experian: https://www.experian.com/freeze/center.html (https://www.experian.com/freeze/center.html) 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. 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! To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes (https://www.buzzsprout.com/2100362/episodes) 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.
6 Nov 2023
FPTP: Episode 2 - Compound Interest - The 8th Wonder of the World
What is compound interest and why should you take it seriously? Listen to this episode and learn how to leverage your money and save for your future! To be entered into the giveaway, you’ll need to subscribe to the show, share this episode with one friend, and then send me an email (cooper@rayolson.net) confirming you have done so and remember to share your favorite pizza spot. The winner will be announced in our next episode! Thank you again! Compound Interest Calculuator: https://www.investor.gov/financial-tools-calculators/calculators/compound-interest-calculator 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. 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! To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes (https://www.buzzsprout.com/2100362/episodes) 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.
15 Sept 2023
From Pies To Prosperity: Trailer Episode
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. 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! "Thanks for joining me and listening to the “From Pies to Prosperity Podcast”... the place to be to accelerate your financial success and simplify your life. I’m Cooper Casillas, your host, your Certified Financial Planning Professional, and your partner in wealth... Tying all that together is why I have named the Podcast “From Pies to Prosperity”. I think we can all remember a past of cheap frozen pizzas… and actually some of us might still be in that phase and that’s okay, I’ll admit I can always go for a solid frozen pie. But, the point here is. Let’s move past those days… let’s keep them in the rearview window, let’s steer towards a better tomorrow… Let’s steer towards prosperity." Website: https://rayolson.net (https://rayolson.net/) Email: cooper@rayolson.net (https://mailto:cooper@rayolson.net/) Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 (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.
15 Sept 2023
FPTP: Episode 1 - Stocks and Bonds?
In our inaugural episode of this podcast I am joined by my partner in crime, Corinne. We talk about what stocks and bonds are, why you might consider investing in them, and the considerations to think about when doing so. We also visit one our our favorite pizza spots, so listen in to find out where and hopefully learn something new about stocks and bonds! 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. 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! To view past FPTP episodes click here: https://www.buzzsprout.com/2100362/episodes (https://www.buzzsprout.com/2100362/episodes) Website: https://rayolson.net (https://rayolson.net/) Email: cooper@rayolson.net (https://mailto:cooper@rayolson.net/) Phone: 804-379-0316 YouTube: https://www.youtube.com/@rayolsonfamilyfinancialpla2161 (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.
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
- YouTube views
- 22,978
- Score snapshot 15 Sept 2025
- Apple Podcasts (US)
- 5.0 / 5
- 7 ratings
- Spotify
- 5.0 / 5
- 4 ratings
Podcast Authority Score: 40 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
- Quality
- 23
- Social presence
- 0
- YouTube
- 72
- Engagement
- 71
Contact From Pies to Prosperity
- Guest appearances
- Does not typically book guests
Based on episode analysis; this does not confirm that the show is currently accepting guests.
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