The Thing We Never Talk About

In this solo episode, Tim pulls back the curtain and shares exactly how he invests his own money — not hot stock tips or market predictions, but the philosophy and decision-making framework behind his choices. He explains why he invests, how he thinks about risk and time, why maintaining strong cash reserves is essential, and why his timeline shapes nearly every decision he makes. Tim walks through when he buys, when he sells, and why he ignores financial media noise in favor of long-term discipline. This episode is about process over prediction — and about building a strategy you can stick with for decades.

One Key Takeaway: The real edge in investing isn’t knowing what the market will do next — it’s having a clear plan, a long timeline, and the discipline to follow it.
Links:
Send me a question to be answered on a future episode. ( https://www.iselerfinancial.com/podcast )
Sign up for the Keep It Easy newsletter. ( https://www.iselerfinancial.com/newsletter )

In this episode, Tim sits down with Vish Khanna, host and producer of the long-running podcast Kreative Kontrol, for a candid conversation about work, money, and creative independence. Vish reflects on leaving conventional media jobs to focus fully on his own show, and the emotional and financial tension that comes with choosing fulfillment over a steady paycheck. They explore how creative labor is valued (or undervalued), what it means to earn “enough,” and how freelancers navigate instability while trying to stay honest & engaged with their work. The conversation also touches on autonomy, burnout, family responsibility, and the realities of building a sustainable creative career outside traditional institutions.
Vish's question for Tim: how does one achieve a healthy, relatively stress-free balance between vocational fulfillment and financial stability as a freelancer or independent business owner, especially after entering a freelance realm after 20 years of conventional jobs with regularly scheduled and consistent pay?
Key Takeaways:
Vish Khanna left a career in traditional media, even though it meant giving up stability, status, and a predictable paycheck.
He describes the shift to independent work as emotionally liberating but financially disorienting, especially when there is no clear benchmark for success or failure.
Vish highlights how independent creators often undervalue their labor, particularly when passion and personal identity are tightly bound to the work.
He talks about the importance of building personal definitions of “enough”, and how that relates to industry norms or social comparisons.
Vish discusses the tension between audience appreciation and financial sustainability, noting that validation doesn’t automatically translate into income.
Links:
Send me a question to be answered on a future episode. ( https://www.iselerfinancial.com/podcast )
Sign up for the Keep It Easy newsletter. ( https://www.iselerfinancial.com/newsletter )
Kreative Kontrol ( http://vishkhanna.com/ )
Vish's profile on Talkhouse ( https://www.talkhouse.com/artist/vish-khanna/ )

Getting stuck in a “comfort zone” is often a sign that something isn’t actually all that comfortable—especially when it comes to money and long-term decisions. In this episode, Tim explores why so many important financial moves get stuck in the “I should” category, why waiting for the perfect moment usually makes things worse, and shares five practical, low-pressure ways to break out of an uncomfortable status quo and start making progress. One Key Takeaway: Real change doesn’t start with a perfect plan—it starts with small actions that gets you moving in the right direction.

In this episode, Tim sits down with Sarah Williams for a wide-ranging conversation about her creative path, professional evolution, and the realities of building a sustainable career on her own terms. Sarah shares her journey from early employee to co-owner & co-CEO, and how her leadership evolved as the company grew. She also reflects on burnout, delegation, financial stability, and redefining success beyond revenue. They explore how money, confidence, and self-trust intersect with creativity, especially when your career doesn’t follow a traditional path. Sarah 

Sarah’s question for Tim: how do you see the relationship between financial health and mental and physical health? Growing up I always had a lot of anxiety about Money. As I've gotten older and looked to create more financial security for myself, my family, and my business, that feeling doesn't really go away. How do you think about these challenges?
Key Takeaways:
Sarah Williams shares her path from being the first employee at her company to becoming co-owner and co-CEO, and how long-term commitment shaped her leadership style.
She discusses the difference between building a lasting brand identity versus chasing short-term marketing trends and quick wins.
Sarah reflects on learning to trust her instincts while also developing systems that support sustainable growth.
She talks openly about learning to delegate and empower others as her role shifted from “doing everything” to leading a team.
The episode highlights the importance of aligning personal values with professional goals in order to build a sustainable, fulfilling career.
Links:
Send me a question to be answered on a future episode.
Sign up for the Keep It Easy newsletter.
Beardwood&Co

In this episode, Tim breaks down everything you need to know about Individual Retirement Accounts (IRAs) and how they fit into a long-term financial plan. He explains the differences between Traditional and Roth IRAs, who can contribute, how much you can save, and how taxes work both now and in retirement. Tim also covers investment choices inside an IRA, rules around withdrawals, and advanced options for self-employed people like SEP and SIMPLE IRAs. Along the way, he shares practical strategies for balancing short-term flexibility with long-term growth. One Key Takeaway: An IRA is one of the most powerful tools for building long-term financial security—but only if you understand how it works and use it intentionally.
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