Afford Anything

#679: Will you still have a job in five years? Zack Kass, former OpenAI executive and 16-year AI veteran, joins us to tackle the question that keeps knowledge workers up at night. Most people worry about the economics — who can pay the bills if AI takes their job? Kass flips the question: What happens when work no longer defines who you are? He argues we're heading for an identity crisis bigger than any economic disruption. In this conversation, Kass explains why everyone wants everyone else's job automated (faster legal services, cheaper healthcare) but nobody wants their own work to disappear. He shares why some jobs will vanish while others explode in demand, and which professions might actually benefit from AI disruption. You'll discover why the real threat isn't job loss — it's that we've become addicted to our devices and forgotten how to live without constant work. Kass reveals how financial illiteracy keeps people trapped in debt cycles that AI could help break. He explains why housing, healthcare, and education costs stay high while everything else gets cheaper, and what might finally change that dynamic. The conversation explores what happens when AI makes basic needs affordable for everyone. Kass predicts some people will pursue passion projects, others will double down on work, and many will struggle to answer a simple question: What do you actually want to do with your day? We discuss practical realities like how a 53-year-old attorney might reinvent herself, why accountants face bigger challenges than lawyers, and which human skills will become more valuable as machines get smarter. Kass shares his theory about competing on kindness rather than intelligence when AI can outthink us all. This isn't another doom-and-gloom AI prediction. Kass makes a compelling case that automation could free us to rediscover community, creativity, and purpose … if we can get past our addiction to both work and screens long enough to imagine what that life looks like. Timestamps: Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. 
(0:00) Introduction (2:00) Zack's AI background at OpenAI (3:15) Will knowledge workers have jobs (4:52) Job automation is complex (7:53) Longshoremen strike over automation (9:06) Everyone wants others' jobs automated (10:14) Identity crisis bigger than economics (13:36) Lawyers might enjoy job loss (21:42) Societal thresholds stop automation (28:52) Bespoke services always find demand (41:34) AI won't replace human therapists (47:11) Dehumanization threatens physical connections (54:55) Financial illiteracy costs billions (1:03:21) Predatory lending traps explained (1:11:51) Housing healthcare education stay expensive (1:26:31) Screen time hides free time Resource: AffordAnything.com/financialgoals Learn more about your ad choices. Visit podcastchoices.com/adchoices

#678: Anonymous (01:52):  "Victoria" is 51, single, and still enjoying their W2 job while building a side business from a passion hobby. They’re thinking about heavy Roth conversions, planning for retirement, and wondering how much traditional money to leave untouched. Should Alex prioritize tax efficiency, or focus on growth and flexibility? Anonymous (34:29): "Gwyneth" and her husband moved to the U.S. to start a sanctuary for senior dogs and cats. With $100,000 in debt soon paid off, two properties in hand, and a dream to buy land for their sanctuary, they’re torn: sell, refinance, or keep their rental property? What’s the best way to fund a long-term dream while building wealth? Soyman (53:28): Soyman is 25, saving aggressively, and planning to take all of 2027 off to go backpacking. They see a rare tax opportunity to convert nearly $30,000 to a Roth at a negative tax rate—but is the strategy worth the small cash buffer and other risks? Resource Mentioned: Interview with Charity: Water founder Scott Harrison Share this episode with a friend, colleagues, your veterinarian: https://affordanything.com/episode678 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#677: Happy New Year! We're kicking off 2026 with a reality check on where your money stands right now. The Good News: Gas prices dropped below $3/gallon. Inflation cooled to 2.7%. The Fed cut rates again. GDP grew 4.3% (surprisingly strong). Gold hit $4,500 an ounce. And 19 states raised minimum wages. The Not-So-Good: Health insurance jumped 10-18%. Unemployment ticked up. Mortgage rates are stuck around 6.2%. And 80% of homeowners are unlikely to sell because they locked in rates below 6%. The Big Picture: The stock market is outperforming the economy. How It Affects You: I call it "millionaire malaise." Your 401k looks great. Your home equity is through the roof (no pun intended). If you bought before 2022, your assets look good on paper. Yet you're stressed out at the grocery store. Everything costs more – insurance, groceries, everything except gas. Jobs are stagnant. People are stuck. We're experiencing the difference between wealth and income. This is 2026: Wealthy on paper. Broke at the checkout line. Whether you're new to money management or a long-timer looking for clarity, this episode cuts through the noise to tell you what actually matters for your finances this year. Download the free resource: AffordAnything.com/financialgoals Timestamps Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (01:33) Warren Buffett's retirement (04:45) Unemployment at 4.6% in November (06:11) JOLTS data and November jobs data (08:04) Gold hitting record highs above $4,500/oz in December (11:26) US inflation at 2.7% in December (20:01) Commerce Department releases GDP numbers at 4.3% (23:08) Gas prices hitting record lows (25:20) Mortgage rates holding around 6.20% (30:26) Minimum wage increases in 19 states (32:23) Health insurance premiums up 10% (employer) and 18% (individual) (35:15) $12 billion USDA aid package for farmers (37:16) Workers over age 50 listing more disruptive tech skills on resumes (39:21) Consumer Sentiment rose in December Share this episode with a friend, colleagues, and cohorts: https://affordanything.com/episode677 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#676: Ally:How can I optimize my asset allocation and Roth contributions now that I’m over $1 million in assets? I’m 45, single, never married, with about $1.2 million in assets. Roughly $100,000 is in stocks, which might scare some people. Here’s my breakdown: Vanguard brokerage account: VTSAX $132,000, ISCV $5,000, VOO $5,000 Vanguard Rollover IRA: VTSAX $65,000, IVV $25,000, VOO $62,000 Vanguard Roth IRA: VTSAX $228,000, ISCV $6,000 Pre-tax 401(k): Active stock fund $218,000 (0.01% expense ratio), Equity dividend fund $55,000 (0.01% expense ratio) Russell 1000: $270,000 (0% expense ratio) HSA: $9,000 in the Russell 1000 and Russell 2000 ESPP: $90,000 Savings account: $12,000 I view my brokerage accounts as savings, where I can sell assets if I need cash, as well as sell my company shares. My questions: How far am I from the efficient frontier? How efficient is my asset allocation? I’ve mostly been a “VTSAX and chill” type. If I rebalance, what’s the best way to do it without incurring taxes? Next year, I’ll make more than $150,000, even after contributing $24,500 to my pre-tax 401(k) in 2026. Can I still do a backdoor Roth, given that I already have an IRA balance? I was told it could be complicated. Am I out of luck investing in a Roth next year? Also, should I roll over my 401(k) into my existing Rollover IRA to gain more investment options, even though the 401(k) fees are very low? I’ve reached over $1 million in assets, but I’m not confident my first million was invested efficiently. I want to correct it before reaching my next million. Emma: Can We Split a Dependent’s Tax Status Midyear to Maximize Health Insurance Subsidies? We’re a family of four with two adults and two children, ages 15 and 21. Our 21-year-old is a full-time university student and is expected to graduate in May 2026. The hope is that she’ll secure a full-time job after graduation. Our health care broker told us that we could claim her as a dependent for half of the year and then have her claim herself for the second half. According to the broker, this would allow her to stay on our health insurance and help us qualify for a larger premium subsidy. Is it actually possible to split a dependent’s tax status this way within a single year, or is this a misunderstanding? Anonymous: Is It Wise to Hold Some Investments Outside the U.S. for Geopolitical Diversification? I’ve always believed that “this time isn’t different,” but lately I’m feeling uneasy. I’m increasingly concerned about what seems like a slow erosion of institutional trust in the U.S., especially regarding agencies and structures that support our financial system. From leadership changes at key government institutions to growing political influence over economic policy, I’m starting to wonder if it’s prudent to hold a small portion of assets physically and legally outside the U.S. I’m not talking about exotic offshore schemes. I mean legitimate ways to invest in broad index funds or ETFs through a brokerage account based abroad—as a form of geopolitical diversification and personal contingency planning. I’d love to hear your perspective. Share this episode with a friend, colleagues, your brokerage rep: https://affordanything.com/episode676 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#675: Welcome to Greatest Hits Week – five days, five episodes from our vault, spelling out F-I-I-R-E. Today’s letter E stands for Entrepreneurship. This episode originally aired in September 2018, at a moment when startup culture was loud, venture capital was abundant, and entrepreneurship was often framed as something that involves outside investors and rapid growth. ____ In this episode, we rewind the clock to 2018. Remember what entrepreneurship was supposed to look like back then? Build a startup. Raise capital. Scale fast. Get rich. That was the dominant story. But our guest, Rand Fishkin, told a different story – a story about founder burnout, debt, and the downside of startup culture. Rand, the founder of Moz, shares how he and his mother accumulated nearly half a million dollars in debt while running an early services business. He talks about what it felt like to face creditors, negotiate settlements, and keep going under intense financial pressure. From there, we move into one of the most misunderstood ideas in entrepreneurship: the difference between service businesses and product businesses. Rand breaks down the trade-offs. Services generate income faster. Product businesses rely on outside capital. And founders often earn far less than people expect. That leads to a deeper conversation about incentives. Once venture capital enters the picture, priorities shift. Profits matter less. Growth matters more — and it affects both the business and your personal finances. High revenue does not automatically translate into personal wealth. We also talk about the side of entrepreneurship that rarely makes the highlight reels: Loneliness. Anxiety. Depression. And the relief that comes from realizing that even the most successful founders often feel lost while they’re building. This conversation feels less like startup advice and more like a long-term framework for thinking clearly about risk, money, and meaning. If you’ve ever questioned whether entrepreneurship automatically leads to financial freedom, this episode offers a grounded and very honest answer. Timestamps Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths. (00:00) Facing creditors and repayment negotiations (08:50) How a services business really works (11:40) From consulting to software (15:00) Services vs. product businesses (12:20) Why high revenue doesn’t mean personal wealth (25:05) Venture capital incentives (27:50) Founder salaries and financial reality (30:40) Startup mythology vs. lived experience (33:20) Loneliness and mental health (36:15) Founder strengths and weaknesses (39:50) Feedback and self-awareness (42:30) Designing a business that fits your life Learn more about your ad choices. Visit podcastchoices.com/adchoices