Welcome to the Modern Family Finance podcast, hosted by Jennifer Dazols, a CERTIFIED FINANCIAL PLANNER™. On this show, Jenni invites guests to share their wisdom on finances, careers, and life. She focuses on the specific challenges and opportunities that Women and LGBTQ individuals encounter in today’s ever-changing landscape.
Whether you're managing your career, starting a business, or preparing for retirement, Jennifer's guests offer practical advice and support. Tune in for insightful conversations that feel like chatting with trusted friends. More at www.ModernFamilyFinance.com
Sitting on Highly Appreciated Stock? How a Charitable Remainder Trust Works (with Dr. Roger Silk)
Holding highly appreciated stock, crypto, real estate or a business interest? A charitable remainder trust (CRT) can help you diversify, defer capital gains taxes and maximize income for your family, even if giving isn't your main goal.
Jennifer Dazols, CFP®, founder of Modern Family Finance, sits down with Dr. Roger Silk, founder and CEO of Sterling Foundation Management. Roger has been helping families at the intersection of wealth and philanthropy since 1998. They cover how CRTs work, who they're a good fit for, when to start planning around an IPO or acquisition, and what happens if your life changes after you fund the trust.
In this episode:
The biggest misconception about charitable remainder trusts
How a CRT lets you sell low-basis stock without an immediate capital gains bill
A $10 million example comparing selling outright with selling inside a trust
How much income you can take out, and how to set the payout
Minimum amounts for public stock, private businesses and real estate
Planning for pre-IPO stock and why timing matters
What to do if you need the money later
Chapters
0:00 Intro
1:30 What Sterling Foundation Management does
3:50 How Roger got into philanthropy and private foundations
5:00 Who charitable giving tools are for
7:00 The tax problem with low-basis stock in California
9:30 How a charitable remainder trust works
13:30 A $10M example: trust vs. selling outright
20:00 How much income can you take from a CRT?
23:30 Balancing payout, deferral and family goals
26:30 Who is a good fit for a CRT
30:30 Pre-IPO stock: when to start planning
33:00 Do CRTs help with RSU or compensation income?
34:00 The biggest misconception about CRTs
35:30 Risks, regrets and how to get money out
37:30 How CRT assets are invested
40:30 Next steps and how to reach Roger
Resources
Modern Family Finance: https://www.modernfamilyfinance.com/
Sterling Foundation Management: https://www.sterlingfoundations.com
Subscribe for more conversations on money, career and life for modern families.
29 Jan 2026
Pre-Marital Agreements in the SF Bay Area: What Couples Should Know in 2026
Prenuptial agreements are one of those topics that many couples know they should talk about—but often avoid. They’re frequently misunderstood, associated with extreme wealth, or seen as unromantic. In reality, prenups can be one of the most thoughtful, practical tools modern couples use to protect themselves and each other.
In this episode of the Modern Family Finance Podcast (https://www.modernfamilyfinance.com/podcast/), I sit down with Katie Burke (https://burkelawsf.com/about/katie-burke/), a San Francisco–based family law attorney, to unpack what prenups (and postnups) really do, who they’re for, and why they matter—especially in California.
21 Jan 2026
SF Bay Area Family Guide to Credit Card Travel Rewards
How do Bay Area families use credit card rewards to take unforgettable trips—without hurting their credit or getting overwhelmed?
In this episode of the Modern Family Finance Podcast, Jenni sits down with Kerry Durkin of Carrie’s Points, Unpacked to break down how busy families can turn everyday spending into meaningful travel using credit card rewards.
Kerry shares how her family used points to book bucket-list trips like Italy and Europe, why rewards travel isn’t just for extreme “travel hackers,” and how families can get started with simple, realistic strategies.
29 Apr 2025
How to Protect Your Partner, Kids, or Chosen Family With the Right Legal Documents
In today’s episode, we’re diving into estate planning—one of the most essential and most often overlooked parts of building a secure financial future. It’s not just about what happens when you're gone—it’s about protecting the people you love and making sure your wishes are honored when it matters most.For women, LGBTQ+ families, singles, and unmarried couples, the stakes can be even higher. The default rules don’t always reflect our lives or our values—which makes thoughtful, proactive planning all the more important.That’s why I’m so excited to welcome Jaime Santos of Santos Walding to the podcast. Jaime is a seasoned estate planning attorney based in the San Francisco Bay Area. A proud East Bay native and a graduate of Berkeley Law, she brings over 20 years of experience in estate planning, business law, and tax strategy. She does it all—and what drives her is helping people protect their families and their futures.
15 Apr 2025
How to Plan for the Future When You're on Your Own or without Family Nearby
In today’s episode, we’re diving into a critical question: What do you do when you don’t have children—or family nearby—to advocate for you as you age?
Whether you’re single, child-free, part of the LGBTQ+ community, or simply navigating complex family dynamics, this episode is for you. My guest is Mia Owsley, a licensed professional fiduciary and founder of Mia’s Fiduciary Services which serves the San Francisco Bay Area. Mia is a true advocate for those needing financial management, estate planning, and care coordination, ensuring that her clients wishes are honored, even when they cannot advocate for themselves.
Show notes: https://www.modernfamilyfinance.com/how-to-plan-for-the-future-when-youre-on-your-own-or-without-family-nearby/
21 Mar 2025
How to Take Control of Your Time, Your To-To list, and Your Life in 2025
In this episode of the Modern Family Finance podcast, we’re diving into a topic that affects everyone—time management and productivity. Whether you’re juggling a demanding career, personal responsibilities, or just trying to keep up with life’s never-ending to-do list, finding balance can feel overwhelming.
Jenni welcomes Alexis Haselberger, a time management and productivity coach in the San Francisco Bay Area. Alexis has helped thousands of people "do more and stress less" through her coaching, workshops, and online courses.
View show notes here: https://www.modernfamilyfinance.com/how-to-take-control-of-your-time-your-to-do-list-and-your-life-in-2025/ (https://www.modernfamilyfinance.com/how-to-take-control-of-your-time-your-to-do-list-and-your-life-in-2025/)
(https://www.modernfamilyfinance.com/how-to-take-control-of-your-time-your-to-do-list-and-your-life-in-2025/)Sign to up receive Jenni’s email newsletter: https://www.modernfamilyfinance.com/download-article/ (https://www.modernfamilyfinance.com/download-article/)
Website: www.modernfamilyfinance.com
12 Feb 2025
2025 Update: SF Bay Area Real Estate
In this episode of the Modern Family Finance podcast, we talk Bay Area real estate with Dan Risman-Jones of Ascend Realty. Dan is an incredible resource with deep expertise in the San Francisco Bay Area housing market, specializing in San Francisco, Alameda County, Marin, and San Mateo. In today’s episode, we’ll dive into everything from Bay Area market trends and navigating mortgage rates to retirement planning and financial strategies for modern families.
25 Sept 2024
How to Obtain a Second Passport or Residence Permit Abroad
In this episode of the Modern Family Finance (https://open.spotify.com/show/7uNq7WaGgZIqLgsG3cY1W8) podcast, I’m diving into the exciting world of international living. As a financial planner based in the San Francisco Bay Area, I love helping women and LGBTQ professionals navigate their financial goals. Having lived in Europe and Asia for years at a time myself, I’m a huge advocate for the benefits of international living—not just for the adventure, but also as a way to reach financial independence faster.
I often hear from clients who want to live abroad but aren’t sure how to secure residency or citizenship in another country. That’s why I’ve invited Jon Green, director at Latitude Consultancy (https://www.latitudeworld.com/teams/jon-green/), to join me. Latitude has helped over 6,000 people obtain second passports or residency permits in 20 countries, and Jon is here to share his expertise.
15 Aug 2024
Beyond The Basics: Tax Strategies for High Income Earners
Today, we have the pleasure of discussing tax-saving tips for high-income earners with Gio Bartolotta. Gio is the co-founder of GoJo Accountants and is pioneering a tech-savvy tax advisory firm. What's particularly fascinating about Gio is that he defies the stereotype of a traditional CPA. He has masterfully integrated his professional practice with his personal lifestyle, allowing him to pursue his passion for traveling around in his RV with his wife.
Show notes: https://bit.ly/tax-strategies-for-high-income
Website: www.modernfamilyfinance.com
11 Jun 2024
Empowering Transitions: From Attorney to Mom to Life Coach
In this episode, we focuses on career and life transitions, addressing questions like discovering one’s true calling, reclaiming identity after a career break, and making significant career changes. We have a great conversation with Tracy Crothers (https://www.modernfamilyfinance.com/?p=5704&preview_id=5704&preview_nonce=ca0ce8911a&preview=true#), a former public interest attorney who transitioned to a life coach. Tracy shares her journey of discovering her true calling and how she now helps others navigate life’s transitions with resilience and purpose.
Show notes: https://bit.ly/show-notes-empowering-transitions
23 Apr 2024
Money with My Honey: How to Manage Finances as a Couple
In this podcast episode I talk about money and relationships with one of my favorite couples, John and David Auten Schneider. My wife and I have had the pleasure of becoming friends with them after getting to know them through their content at the Debt Free Guys (https://debtfreeguys.com/) website and the Queer Money podcast (https://queermoneypodcast.com/kickstarter).
John and David help LGBTQ people and their allies live fabulously, not fabulously broke. Today’s podcast centers around the topic of “Money with your Honey” as relationships and finances are undoubtedly intertwined. We discuss how couples can effectively manage their finances while strengthening their bond.
Show notes:
https://www.modernfamilyfinance.com/money-with-my-honey-how-to-manage-finances-as-a-couple/ (https://www.modernfamilyfinance.com/money-with-my-honey-how-to-manage-finances-as-a-couple/)
11 Feb 2024
How to Buy a Home in the Bay Area in 2024
As a financial planner in the Bay Area, I get a lot of people who want to talk to me about getting their finances in order because they’re preparing to buy a home. But in today’s real estate market, it can be hard to figure out what to do. So in today’s webinar, we’re going to talk with my friend, Brook Baird (https://www.compass.com/agents/brook-baird/).
Brook is a Bay Area native and she’s had a real estate license since 2005. She works with a lot of single women, alternative family households, and entrepreneurs. Last year, we did a popular webinar together called How to Buy a Home in the Bay Area Without a Gazillion Dollars (https://www.modernfamilyfinance.com/how-to-buy-a-house/), in which she shared with us different alternative financing programs for first time buyers.
Join me for a Q&A with Brook, followed by my insights on financial ratios for determining if a home is affordable for you.
Show notes: https://www.modernfamilyfinance.com/2024-update-how-to-buy-a-home-in-the-bay-area/
11 Feb 2024
How to Use Equity to Fuel Financial Independence
When I used to work in Silicon Valley as a tech employee, I received restricted stock units (RSUs) that helped fuel our financial journey (https://www.modernfamilyfinance.com/our-story/). If you’re a tech employee who aspires to live and work on your terms, your equity based compensation could have the potential to accelerate your path to financial independence. But we know it can feel complicated, especially around taxes.
My go-to guru when it comes to tax is Bay-Area native Kirsten Pfenning (https://kirstenpfenning.com/), a CPA serving individuals and small business owners with 15+ years of experience.
Show notes: https://www.modernfamilyfinance.com/how-to-use-equity-comp-to-fuel-your-financial-independence/
11 Feb 2024
How to Win at Salary Negotiation
As a woman, a person of color, as an LGBTQ individual, I get how negotiation can be in an uncomfortable conversation when you’re used to having a fight just to get a seat at the table. So that is why I wanted to talk to Kimberly Aguilera (https://www.linkedin.com/in/kaguilera/), founder of Zocalo, (https://zocalo.cc/) a recruiting firm bringing top-tier talent to today’s most ambitious and admirable companies.
Kimberly is a recognized leader in the executive search space. She is a hands on matchmaker who understands the needs of both companies and candidates. Impressively, 85% percent of her placements to date have been filled by people of color, LGBTQ individuals and members of other underrepresented groups.
Show notes: https://www.modernfamilyfinance.com/how-to-win-at-salary-and-benefit-negotiation-for-women-and-lgbt-professionals/
11 Feb 2024
How to Set up a CA Business and Save Taxes
As a financial planner who works with women and LGBTQ professionals, a lot of my clients are self-employed and small business owners. As a small business owner myself, I’ve had to figure out how to navigate the legal of setting up our business and hiring. I always turn to Jaime Santos (https://santoswalding.com/people) of Santos Walding LLP (https://santoswalding.com/) for help. Jamie is a native of the East Bay. She got her law degree at UC Berkeley and she has been in legal practice for 20 years. After working at top tier law firms she started her own law firm specializing in estate planning, business law, tax planning, and nonprofit management. So we wanted to invite Jamie here to talk to us all things self employed and small businesses.
Show notes: https://www.modernfamilyfinance.com/how-to-setup-your-own-business-and-save-taxes-in-california-for-2024/
11 Feb 2024
How to Make Successful Career Leaps Mid-Career
If you are a mid-career woman or LGBTQ professional, this might be a time in which you are asking yourself what’s important for the next phase of your career. For some of you, the goal might be to get to the next level as an executive. Others of you might want to make changes such as staying in the same industry but changing the type of company or role you’re in.
When I left my company after 15 years, I turned to executive coach, Lana Kairos, (https://www.linkedin.com/in/lana-kairos/)for help. Her advice was really instrumental in helping me clarify my vision and getting to what I’m doing today. So, I’m really happy to have Lana join me today for a conversation about redefining your professional narrative and how to make successful career leaps.
Show notes: https://www.modernfamilyfinance.com/redefining-your-professional-narrative-a-mid-career-guide-to-successful-career-leaps/
10 Feb 2024
How to Buy your Own CA Health Insurance
When I left my Silicon Valley tech job after 15 years to start my own business, one of my main concerns was how to buy health care coverage for my family. Access to health care coverage simply isn’t a concern when you work for a Fortune 500 company competing to offer the best benefits packages to attract top talent.
As a financial planner who specializes in working with self-employed individuals (https://www.modernfamilyfinance.com/self-employed-and-money/), I see how health care can be a roadblock if you’re considering launching from salaried security. Freelancers, contractors, job seekers, and those wanting to take a break from conventional work life or retire early worry about how to access comprehensive and affordable coverage.
This month during open enrollment, I interview Ariana Brill (http://askariana.com/), a healthcare advocate who also has a law degree and MBA. After her own frustrations witnessing her partner struggle to get health insurance, she opened her own business helping individuals in California navigate their options and enroll in coverage. She shares with us the latest on accessing healthcare through Covered California for coverage in 2024.
Show notes: https://www.modernfamilyfinance.com/how-to-buy-your-own-health-insurance-in-california-for-2024/
Reach and audience
Public platform figures. Ratings count people who left a rating, not total listeners.
Apple Podcasts (US)
5.0 / 5
2 ratings
Podcast Authority Score: 21 / 100
A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.
Quality
19
Social presence
0
YouTube
0
Engagement
60
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