All the Hacks: Money, Points & Life

Host: Chris Hutchins
Episode: 10 Lessons That Challenged My Thinking on Money and Life
Guest: Tad Fallows (Long Angle)
Date: November 5, 2025

Overview

In this episode, Chris Hutchins and Tad Fallows, co-founder of Long Angle, break down the 10 most impactful lessons and themes from a recent retreat with top investors. The conversation quickly moves beyond money to explore fundamental assets like health, relationships, intentional living, and managing risk. Drawing from both personal stories and breakout sessions with experts, they share the insights that most changed their thinking about wealth, happiness, and designing a values-driven life.

Key Discussion Points & Insights

1. Health as the Ultimate Asset

• Health vs. Wealth: While the group was full of savvy investors, Chris notes that health, not money, was the “most important asset that came up in this retreat.”
• Healthspan vs. Lifespan: It's not about living longer, but maintaining a high quality of life until the very end.
• Be Your Own Advocate: Modern healthcare often misses the cutting edge. Chris shares his story of discoveriing key biomarkers after years of bad advice and stresses the need to push your providers (e.g., asking “If I were willing to spend a little bit out of pocket, what should I do?” – [05:16]).
• Women's Health & Menopause: There’s underinvestment and out-of-date thinking; “You have to be your own advocate…if you’re not testing, you might not know what caused the change” – Chris ([07:56]).
• Outsourcing Health: If you’re not proactive, consider paying for extra screenings, tests, or even a personal trainer to ensure you follow through ([08:20]).

2. Relationships Trump Money

• Building Adult Friendships is Hard: Many successful attendees admitted they struggle to make real friends as adults ([12:58]).
• Intentionality is Key: Repeat interactions are necessary; things like church, regular hobby groups or set meetups help forge real bonds ([14:04], [15:27]).
• Family Dynamics: Sometimes, the most valuable thing kids want isn’t money, but your time:
  • “Dad, I don’t need any of your money. Can you just spend some time with me?” ([16:21])
• Travel for Connection: Best trips aren’t about checking sights but deepening relationships ([17:42]).

3. Rethinking the Purpose of Travel

• Intent Matters: Are you traveling to check boxes or to create shared experiences?
  • “Are you trying to reconnect with your spouse? …then travel can get you what you’re trying to accomplish.” – Tad ([19:07])
• Repeat Destinations Shine: Magic often comes on the 2nd or 3rd visit, when the pressure’s off ([20:15])
• Travel with Kids: “To watch your children experience a thing you’ve experienced in the past…is interesting.” – Chris ([20:41])

4. Parenting: Embracing Imperfection

• Lighthouse Parenting: Guide and support; don’t always interfere ([21:20]).
  • “Your job is to be this grounded thing…not always to just go get in the waves with them.” – Chris ([21:46])
• Letting Kids Struggle: “You have zero temptation to pick your kid up and put them at the top of the staircase…” but as they get older, it’s harder to let go ([22:41])
• Grace for Parents: There’s no perfect way—give yourself permission to fail and adapt ([22:41], [24:50]).

5. Let Your Imagination Expand What’s Possible

• Learning from Kids: Kids believe they can have unlimited careers; adults get stuck believing what’s possible is limited ([25:02]).
• Life Diagnostics Exercise: Rate satisfaction and importance across life domains, then imagine a “wildly successful” version ([25:57]).
• Think Like a Kid Again: “What would a crazy version of this look like?” ([27:19]).
• Multiple Seasons in Life: Don’t pigeonhole yourself—adults in other cultures regularly switch careers or passions ([30:36]).
  • “In Iceland … it’s very normal for people to live their life in seasons…” – Chris ([30:36])
• Applying Skills to New Realms: Success in business can translate to purpose-driven nonprofit work ([28:48]).

6. Start With Your “Why” Before Strategy

• Estate Planning & Investing: Abundant discussions on complex structures, but most attendees hadn’t defined their objective ([35:04]).
  • “What is the objective you are trying to accomplish? Top three answers: ‘I’m not sure,’ ‘I don’t know,’ ‘I have no idea.’” – Tad ([35:58])
• Check the Cart-Horse Problem: Don’t set up elaborate financial structures unless they serve a clear, personal purpose ([37:56], [38:25]).
• Travel Analogy: “If you find a killer deal on a flight to Frankfurt, but you didn’t want to go…you really shouldn’t buy it.” ([38:25])

7. Managing Risk, Not Eliminating It

• Insurance Wisdom: Insurance exists to move catastrophic risk. “If you can afford the loss, don’t insure it” ([39:13], [42:06]).
• Rising Premiums & Claims Strategy: Small claims can make you uninsurable; set deductibles above the threshold you’d actually use ([42:06]–[43:02]).
• Confirm Insurability: Always check insurance BEFORE buying property ([43:02]).
• Risk Inherency: Risk persists—it just moves around; you can’t eliminate it ([38:39], [43:29]).

8. Diversification: Beyond U.S. Stocks

• Overconcentration Risk: The S&P 500 has become tech-heavy (approaching 50%), so diversification is lower than it appears ([44:19]).
• Luck vs. Skill: Don’t be lulled by recent U.S. stock outperformance; other countries have seen dramatic reversals ([44:59]).
  • “If you’d been all in on Argentina in the ‘20s, you’d have lost everything.” – Tad ([45:36])
• Other Assets: You don’t need a huge portfolio for exposure—REITs, ETFs, and more are available for all investors ([47:47]).

9. Don’t Let Tax Optimization Rule Your Life

• Qualified Real Estate Professional Example: Optimizing taxes can eat up your time and joy without meaningful gain ([50:41]).
  • “Do you even like doing that? No, but I saved $3,000.” ([51:45])
• If It Fits Your Life, Great—But Don’t Force It. ([51:45]).
• Real Wealth vs. Tax Obsession: Guy Raz: After a point, money doesn’t matter. “There’s nothing a billionaire can do that I can’t do that I actually want to do.” ([53:07])
• Don’t Overconcentrate Assets to Avoid Taxes: Sometimes, realizing gains and paying taxes is wiser than risking everything ([54:10]–[55:12]).

10. There’s No One-Size-Fits-All Answer

• Outsource vs. DIY: Decide where you want to be hands-on (health, investments, parenting, taxes), and where you’d gain more by outsourcing ([55:12]).
• Cost of Mistakes vs. Cost of Experts: For some, even hiring two or three CPAs makes sense if mistakes are very costly; for others, TurboTax is enough ([60:15]).
• Personal Fit, Not Mimicry: Just because others structure things one way doesn’t mean it’s right for you ([59:06]).
• Prioritize Time and Values:
  • “If you take money off the table…there are a lot of human problems we all have that seem pervasive…[59:57].
  • “How do you spend your time on the weekends? Is it actually focusing more on your career and your money, or on the things you actually care about?” ([61:23])

Notable Quotes & Memorable Moments

• “One of the most important assets that came up in this retreat was health...If you don’t have health, you can’t let those [other] assets compound.” – Chris ([03:04])
• “You have to be your own advocate.” – Chris ([07:56])
• “If knowledge was the limiting factor, we’d all be billionaires with six pack abs.” – Tad ([09:15])
• “Dad, I don’t need any of your money. Can you just spend some time with me?” ([16:21])
• “Magic often comes on the 2nd or 3rd time you’ve visited a city.” – Tad ([20:15])
• “Let them deal with the struggles…Your job is to be this grounded thing that’s there, that’s supportive, but not always to just go get in the waves with them.” – Chris ([21:34])
• "In Iceland…it’s very normal for people to live their life in seasons." – Chris ([30:36])
• “What is the objective you are trying to accomplish? ‘I’m not sure, I don’t know, I have no idea.’” – Tad ([35:58])
• “Insurance is not a silver bullet…If you want to transfer that risk, you’re going to have to pay a lot because you create a lot of risk in the first place.” – Tad ([41:31])
• “There’s nothing a billionaire can do that I can’t do that I actually want to do.” – Guy Raz, recounted by Chris ([53:07])

Selected Timestamps for Key Segments

• Health as an Asset & Self-Advocacy: [03:04] – [08:20]
• Relationships are Hard/Easy to Neglect: [12:27] – [16:06]
• Travel as Connection (not Checklist): [17:42] – [20:15]
• Parenting—Letting Kids Struggle: [21:20] – [24:50]
• Expanding Possibility—Imagination & Seasons: [24:50] – [31:34]
• Defining Purpose Before Structure (Estate, Investments, Travel): [34:10] – [38:39]
• Managing Risk w/ Insurance & Diversification: [39:13] – [47:47]
• Tax Optimization vs. Life Optimization: [50:41] – [55:12]
• Personal Fit & No One-Size-Fits-All: [55:12] – [62:01]

Final Takeaway

Money matters, but it’s not the most valuable thing. Health and relationships compound in ways wealth can’t—yet they’re easy to overlook. Define your goals before you optimize, manage risks thoughtfully, and stay intentional in spending your time where it matters most. And remember: there’s no perfect playbook—so use frameworks that help you live a life you’re excited about.

For resources and further reading, check out allthehacks.com and longangle.com.