
From Generation to Generation
By Aspira Wealth of Raymond James Ltd


#10 Blockchain, Crypto and Stablecoins – Danger or Opportunity? with Dr. Michael King and Dr. Andreas Park
This episode explores the evolving role of cryptocurrencies and blockchain in our world. Host Chris Raper speaks with Dr. Michael King, Associate Professor at the Gustavson School of Business and author of Fintech Explained – How Technology Is Transforming Financial Services, and Dr. Andreas Park, Professor of Finance at the University of Toronto’s Rotman School of Management. Together, they debate whether crypto is a revolutionary force or a risky experiment, touching on Bitcoin, Ethereum, stablecoins, and even gold-backed tokens. We also reference insights from Cam Harvey of Duke University, whose research paper compares Bitcoin and gold. This conversation is for educational purposes only and not financial advice.
As always, if you have any questions or feedback, we would love to hear from you chris.raper@raymondjames.ca. Or you can find us at www.aspirawealth.com.
Thank you to Nathan Clark for composing our podcast music! He can be reached at nathancaclark@gmail.com

#9 Don't Leave a Mess - How to Disaster-Proof Your Family Legacy with Sandy Pollack
This episode of From Generation to Generation features a masterclass in thoughtful wealth transfer from two seasoned professionals. Chris Raper and author Sandy Pollack unravel the psychological and relational layers of estate planning, from money scripts and family dynamics to the silent pressures between generations. Listeners will gain practical tools and heartfelt perspective to transform financial planning into a legacy of clarity and compassion. Sandy’s insights come from decades of working with business families and culminate in her bestselling book Don't Leave a Mess. Chris, a baby boomer dad and seasoned wealth advisor, adds his own lens—personal, professional, and deeply reflective. Don't Leave a Mess: How to Disaster -Proof Your Family Legacy is available in print and audiobook for those looking to go deeper. Visit dontleaveamess.ca to learn more.
As always, if you haveany questions or feedback, we would love to hear from you:chris.raper@raymondjames.ca. Or you can find us at www.aspirawealth.com.
Thank you to Nathan Clark for composing our podcast music! He can be reached at nathancaclark@gmail.com.

#8 Navigating Uncertain Markets with Eileen Kelly, Wealth Advisor & Professional Athlete
As the Trump tariffs have caused a lot of angst recently, Aspira’s two wealth advisors bound together to talk about what we can control in stressful markets: how we think and how we act. Our guest, Cross Border Wealth Advisor Eileen Kelly (Millennial), speaks to “how we think” from her training as a professional golfer with top sports psychologist, Jim Murphy (you may recognize him as the author of New York Time's Bestseller Inner Excellence, the book A.J. Brown was reading on the Eagles football field). Having consistently executed a high level of performance amongst fierce competition in PGA tournaments around the world, she shares the secrets of her training and how it can help us navigate stressful markets. Cross Border Wealth Advisor and co-host, Chris (Boomer), shares his veteran wisdom on “how we act” from his investment career and as a student of history. Plus, we all discuss how each of our generations receives and processes the news – TikTok anyone?
As always, if you have any questions or feedback, we would love to hear from you: brittany.pilgrim@raymondjames.ca & chris.raper@raymondjames.ca. Or you can find us at www.aspirawealth.com.
Thank you to Nathan Clark for composing our podcast music! He can be reached at nathancaclark@gmail.com.

#7 Planning our First Family Wealth Meeting with Alexa Wowchuk (the other daughter)
We may be hypocrites for saying this but... we've never actually had a "family wealth meeting" as a family. Boomer dad Chris would like to start though. Since we can't feasibly host our entire family on the podcast and record our first family meeting live (we considered it), we thought we would do a live "prep meeting" with Chris and Brittany and the other daughter/sister, Alexa (Millennial). Things got vulnerable pretty quick. From family narratives, to what successful wealth management means to us, to the nitty gritty practical's, to the role of grandparents, to fighting dragons - we are so glad we had this conversation ahead of time.
As always, if you have any questions or feedback, we would love to hear from you: brittany.pilgrim@raymondjames.ca & chris.raper@raymondjames.ca
Thank you to Nathan Clark for composing our podcast music! He can be reached at nathancaclark@gmail.com.

#6 Young & Scrappy 102: How to Start Investing
After listening to our Y&S 101 episode, you may be thinking, "Okay, but how do I actually start investing then??". Welcome to 102! Here we outline a 5-step-process that you can use to make your first investment and that you can come back to for any investment decision in the future. To cap it off, Chris shares some hard-earned practical tips and Brittany walks through a real life example with Chris to see how this 5-step-process plays out. Listen, take out your headphones, and go open that FHSA!
As always, if you have any questions or feedback, we would love to hear from you: brittany.pilgrim@raymondjames.ca & chris.raper@raymondjames.ca
Or reach us at AspiraWealth.com.
Thank you to Nathan Clark for composing our podcast music! He can be reached at nathancaclark@gmail.com.

#5 Your Parents' Last Days with Dr. Mike Jones, MD
*Unbeknownst to us at the time of recording, this episode was recorded on Chris's dad's last day. This makes it all the more special to us and hopefully to you as well. *
You either have already, are currently, or will in the future navigate caring for your parents in their final chapter. Chris spent a great deal of time since January caring for his dad, who is now in his final chapter and after all the financial planning he has done for countless clients, it is not how he pictured it. As our good friend Dr. Michael Jones knows, having been the doctor to many patients in their last days, it never is. Most of us wish we had of talked through all the details before anyone got sick. From a medical, financial, and emotional perspective, this is what to expect and how to prepare for when things go south, when your parents are in their final chapter.
More on Chris, Brittany, and Aspira Wealth: https://www.aspirawealth.com/
As always, if you have any questions or feedback, we would love to hear from you:brittany.pilgrim@raymondjames.ca & chris.raper@raymondjames.ca
Thank you to Nathan Clark for composing our podcast music! He can be reached at nathancaclark@gmail.com.

#4 Funding Post-Secondary Education Across Generations
What is the best way to save for your kids or grandkids education? And what should a student do if no one saved anything for them?
Chris and Brittany get into the 4 different ways to fund a post-secondary education, and which way will serve you and the generations to come best. Chris resurrects some unexpected financial advice he gave Brittany around student loan repayments. Brittany shares her experience navigating the workforce with an arts degree. Chris also gets to nerd out about the sectors where he predicts massive job opportunity in the next 10-20 years.
More than anything, education is one of the most incredible opportunities we have to help grow the generations to come. Let’s make sure we ring everything we can from it.
More on Chris, Brittany and Aspira Wealth: www.aspirawealth.com
As always we'd love to hear your questions or feedback: chris.raper@raymondjames.ca & brittany.pilgrim@raymondjames.ca.
Thank you to Nathan Clark for composing our podcast music! He can be reached at nathancaclark@gmail.com.

#3 Young & Scrappy 101: Mastering the Basics
Our intermittent series YOUNG & SCRAPPY is made for 25-35 years old who want to set themselves up for success financially. We recognize that not everyone has a Financial Advisor for a dad. Not to mention, when you are starting out, the reality is you are largely relying on your own decision making. Chris has learned some things over the years about what young people can do with their money habits to best serve them throughout life. Brittany has benefited, but also has more questions. Consider this an open family discussion and you are part of the family. If you didn’t have a financial-advocate-mentor-friend-in-your-court, now you do.
In Mastering the Basics we cover: spend less than you make, paying yourself first, anti-budgeting, good debt vs bad debt, the magic of compound interest, owner vs lender, and finally how to get started investing.
More on Chris, Brittany, and Aspira Wealth: https://www.aspirawealth.com/
As always, if you have any questions or feedback, we would love to hear from you: brittany.pilgrim@raymondjames.ca & chris.raper@raymondjames.ca
Thank you to Nathan Clark for composing our podcast music! He can be reached at nathancaclark@gmail.com.

#2 Giving with Jason Roberts
Just in time for the Holiday season, we sit down for a humbling discussion about being generous. In Canada right now, only about 18% of us report giving in our tax filings (The Giving Report, 2023). In 1990, that number was 29.5%. Researchers have even given this staggering statistic a moniker, “the Giving Gap”. With an incredibly unique story, Jason provides valuable insights about how we teach our children to be generous and why it matters. Chris gets uncomfortable (as usual!) reflecting back on raising his kids. Brittany is given new hope for her fellow young people. With great purpose and fresh perspective, 'we wish you a merry Christmas'!
Jason Roberts came out of the mess of addiction at 25 years old, when he checked into Wagner Hills, an addiction recovery facility in Langley, BC. He later began working with addicts through Community Builders at Christian Life Assembly. He spent some time in Hong Kong working with St Stephen’s Society and Jackie Pullinger. After moving back to the Lower Mainland, Jason ran the social work department at CLA. While he was back at CLA doors opened for him to speak to pastors in Russia about addiction treatment. He started helping and eventually moved to Russia to help build and train a team to run a treatment centeroutside of Moscow. After living 2 years in Russia, he came back to Canada and started Recovery Church where he pastored for 10 years. Jason then moved into the position of Men’s Campus Director at Wagner Hills Farm before becoming the current Executive Director of Wagner Hills. He is married to the most excellent Nicole Roberts and has Ali, Max and Zoe as his wonderful children.
More on Jason:
https://ca.linkedin.com/in/jason-roberts-23398612a
More on Chris,Brittany, and Aspira Wealth: https://www.aspirawealth.com/
As always, if you haveany questions or feedback, we would love to hear from you:brittany.pilgrim@raymondjames.ca & chris.raper@raymondjames.ca
Thank you to NathanClark for composing our podcast music! He can be reached atnathancaclark@gmail.com.

#1 Well-Being with Dr. Tanis Farish
Who else watched the blue zone documentary*? For us, it was an incredible reality check that we can gather money, build relationships, achieve career success, and have a family, but none of that matters if we aren’t able (or even around!) to enjoy it. Health is probably every parent’s ultimate wish for their kids at the end of the day. Our well-being is precious. And yet, as Chris (boomer) said before recording this episode, “what does wellness even mean??” We’ve brought on Dr. Tanis Farish to have a deep discussion on this question. Brittany (Gen Z) is elated to get her dad in the room for this eye-opening conversation. If your family gets heated when talking about mental health, exercise, and wellness – this is a good listen for all ages.
‘When health is absent, wealth is useless´ is a quote from Herophilus, an ancient Greek physician, and it still rings true today.
Dr. Tanis Farish (Gen X) is an advocate and ambassador for lifelong movement and mental health. She has been a teacher and researcher in the fitness & performance field for over 25 years. Curious and inspired through her training as a clinical exercise physiologist, health coach and yoga instructor, her research focuses on the connection of how we move, feel, and think. She holds a doctorate in the area of mental health and fitness promotion where she conducted her research with the Department of National Defense. She also holds degrees in coaching (MEd – University of Victoria) and life sciences (BSc – Queens University). Tanis teaches and conducts research in the Centre for Sport and Exercise Education at Camosun College in Victoria BC. She is an adjunct faculty in the School of Public Health at the University of Alberta and is a lecturer and graduate supervisor at several other post-secondary institutions.
References in this episode:
- Martin Seligman, The PERMA Model https://positivepsychology.com/perma-model/
- “Live to 100: Secrets of the Blue Zones”, Netflix and Dan Buettner https://www.netflix.com/ca/title/81214929
- https://www.participaction.com/
- Kelly McGonigal, The Joy of Movementhttp://kellymcgonigal.com/the-cover-story
- Adam Grant https://adamgrant.net/
- Dr. John Ratey, Spark: The Revolutionary New Science of Exercise and the Brainhttps://www.amazon.ca/Spark-Revolutionary-Science-Exercise-Brain/dp/0316113514
- Dr. Gabor Maté https://drgabormate.com/
More on Tanis: https://ca.linkedin.com/in/tanisfarish https://wellandwhyresearchlab.opened.ca/page-2/present-students/
More on Chris, Brittany, and Aspira Wealth:https://www.aspirawealth.com/
As always, if you have any questions or feedback, we would love to hear from you: brittany.pilgrim@raymondjames.ca & chris.raper@raymondjames.ca
Thank you to Nathan Clark for composing our podcast music! He can be reached at nathancaclark@gmail.com.

The Pilot: Starting with our Family
To start the podcast, we wanted to check in with our own family. In this pilot, we sit down with Ann and Harold - Chris's 88 and 92 year-old parents, aka Brittany's Grammy and Grandad. In a candid discussion between widespread generations, we unpack the experiences in our family and in our world today. Brittany had some humbling thoughts on how hard work was taught in our house, Harold highlighted some key differences on the economy now compared to his day, Ann had some wonderful insights on the unspeakable value of relationship and Chris tried to shine some light on how things will change for the young people of today.
From Generation to Generation is hosted by Chris Raper and Brittany Pilgrim. Chris Raper is Co-Founder, Portfolio Manager and Senior Wealth Advisor at Aspira Wealth of Raymond James Ltd in Victoria BC. He is married to the backbone of the family, Arleen, and has two married adult daughters, Alexa and Brittany. Co-host and youngest daughter, Brittany is a marketing assistant by day and actor by night. She and her husband, Zech, are newly married and love being Aunty B and Uncle Z to Alexa and her husband's one-year-old, Willa.
As always, if you have any questions or feedback, we would love to hear from you :)
www.aspirawealth.com
brittany.pilgrim@raymondjames.ca
chris.raper@raymondjames.ca
We want to give a big thanks to Nathan Clark for composing our music. He can be reached at nathancaclark@gmail.com.