Afford Anything®

Picture this: you’re 26 years old, fresh out of Wharton, and you decide to start a business with two friends. You spend years building a digital marketing firm that eventually works with Dollar Shave Club and Madison Reed. You bootstrap the entire thing without taking a dime of venture capital funding.

That’s exactly what one Wharton graduate did — and her story represents the reality of entrepreneurship that most people never hear about.

Lori Rosenkopf, a management professor at Wharton Business School and head of Venture Labs, joins us to shatter the biggest myths about starting a business. The Mark Zuckerberg college dropout story? It’s not just rare — it’s misleading.

Research shows that the most successful entrepreneurs, those in the top 0.1 percent of venture-backed firms, average late 30s to early 40s when they start their companies. Many continue launching businesses into their 50s and 60s. 

Your age and corporate experience isn’t holding you back from entrepreneurship — it’s actually giving you an advantage.

Rosenkopf breaks down 7 different types of entrepreneurs, from disruptors who overturn entire industries to bootstrappers who build profitable businesses using their own resources. You’ll hear about a founder who disrupted the hair color industry in her 50s with Madison Reed, and a banker who built an entire financial services division inside Square.

We cover the rise of direct-to-consumer brands in 2013, why 80 percent of entrepreneurs are bootstrappers, and how artificial intelligence is creating new opportunities for people to start businesses without massive upfront investments.

Rosenkopf explains her “six Rs” of entrepreneurial thinking: reason, recombination, relationships, resources, resilience, and results. She argues that most people already think entrepreneurially without realizing it — even parents who optimize their family routines are solving problems through innovation.

We explore the world of “intrapreneurs” — people who build new businesses within established companies — and discuss acquisition entrepreneurship, where people buy existing small businesses instead of starting from scratch.

Whether you want to start a side hustle, position yourself for a promotion, or eventually launch your own company, Rosenkopf’s framework shows multiple paths to creating value through innovation.

Resources:

Unstoppable Entrepreneurs

Timestamps:

(0:00) Entrepreneurship myths

(1:28) Data on successful entrepreneur ages

(2:10) Seven entrepreneur archetypes 

(3:09) Defining entrepreneurship through value creation

(5:27) The disruptor model 

(8:13) Direct-to-consumer origins

(11:13) Bootstrapper 

(14:03) Transitioning from employee to bootstrapper

(18:38) AI’s impact on entrepreneurship

(28:27) Social entrepreneur 

(35:31) Technology commercializer 

(39:45) The Funder 

(43:12) The Acquirer 

(58:06) Intrapreneurship 

(1:03:12) Finding your entrepreneurial calling

(1:14:40) Six Rs of entrepreneurial mindset

(1:19:50) More information

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Paul is worried the private equity investment he’s about to make could be a scam. How can he do his due diligence and stay protected when there’s a shortage of reliable information?

Rob is questioning the purpose of a bond allocation in his eight-figure investment portfolio. Is he on to something, or is there a legitimate case to add them?

Dan can retire in a few years, but he’s itching to do it now. Would buying a business be the key to unlocking an earlier exit from his W2?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

P.S. Got a question? Leave it here.

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Paul asks (2:38): How do you verify a private fund is legit — beyond just trusting a podcast host?

I’m looking to diversify and had my eye on a mobile home park fund called Sunrise Capital, run by Kevin Bupp. I’ve listened to their podcast for a while, and the fund has what appears to be a solid track record.

I was about to invest, but when I went to wire the funds, the bank couldn’t verify the account number they gave me. That raised a red flag. I called investor relations, and they said they’d never heard of that happening before.

Then, when I called a financial help line, someone asked me, “How do you know they’re legit?” And I realized… I didn’t have a good answer. I know they’re public-facing and have raised three previous funds, but how else can I independently verify that this is a legitimate investment?

I have an $11 million net worth, with $17.3 million in real estate and $9.8 million in equity. My liquid assets are entirely in Vanguard Total Stock Market (VTI) and cash reserves for the properties — no bonds.

Given that more than half my wealth is in diversified, income-generating real estate, do bonds still play a role in my portfolio? If so, how much, and why — especially for someone whose career and balance sheet are already deeply tied to real estate and index funds?

I’m 56 and my wife is 55. We’ve saved $1.7 million for retirement—$600,000 in a Roth IRA, the rest pre-tax—and have another $450,000 in after-tax savings. Our side hustles (started in 2022 and 2024) now cover 20 percent of our expenses.

Our current plan is for me to work another three to four years, then live off after-tax savings and side hustle income for five to seven years while our retirement funds compound. We’ve essentially hit Coast FI and could likely retire now if we were frugal and included Social Security.

But recently, I explored buying a small business. I signed an NDA, reviewed financials, and spoke to a bank about an SBA loan. That deal might not work out, but it sparked a bigger idea: could business ownership become our bridge to full retirement?

I’ve enjoyed my side hustle, but it won’t scale to full-time. I’m considering using after-tax savings—or the Rule of 55—to fund a down payment. Here’s my challenge: Unlike the FI space, the world of small business acquisition feels fragmented and hard to navigate. 

What are the best resources for learning how to buy a business? How do I vet a trustworthy advisor? And what framework can help me decide if this path fits our long-term FI plan?

Resources Mentioned:

Interview with Dr. Eric Cole

Interview with Katie Gatti Tassin

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#632: There are 10 conversations that a person should have at work in order to do a better job, have better relationships at work, and make more money.

Melody Wilding, Professor of Human Behavior at Hunter College, joins us to talk about how you can get the most out of your boss.

Resources:

Managing Up by Melody Wilding: managingup.com

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) The 10 Conversations Framework
(02:37) Shifting Workplace Dynamics
(06:11) Key Conversations for Alignment
(10:02) Understanding Your Boss’s Priorities
(12:02) Mapping Stakeholder Influence
(15:28) Visibility and Proximity Bias
(20:31) Managing Shifting Priorities
(22:11) Understanding Boss Archetypes
(28:01) Navigating Personality Frameworks
(32:06) Articulating Your Communication Style
(35:03) Taking Ownership and Suggesting Ideas
(39:59) Building a Reputation Through Ownership
(45:03) Setting and Framing Boundaries
(56:01) The Ripple Effect of Unaddressed Issues
(59:00) Feedback Conversations
(01:03:02) Recapping the Framework Steps
(01:11:09) Building Your Story Bank
(01:18:01) Advancement and Compensation Conversations
(01:25:15) Framing Your Compensation Request
(01:29:00) Navigating Policy-Based Responses
(01:31:51) Creative Compensation Solutions
(01:34:29) Knowing When to Leave
(01:36:13) Assessing Future Opportunities

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Your Next Raise is open for enrollment: Your Next Raise

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Jason’s analysis of his retirement plan shows that the simple path beats the efficient frontier. Is he right or is he missing something?

Minerva is worried about the impacts of tax inefficiency to her wealth. Are her investments properly located?

Scott feels frozen because he doesn’t understand the nuances of the efficient frontier. Where can he get a simplified explainer so he can start taking action?

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

P.S. Got a question? Leave it here.

Resources Mentioned:

Episode 577-qa-the-efficient-frontier-was-perfect-until-hr-got-involved/ | Podcast Episode

Episode 547-ask-paula-we-have-2-million-at-40-now-what/ | Podcast Episode

Your Next Raise | Course

Asset Allocation Made Simple | Free Download

The Truth About Making the Efficient Frontier Work in Real Life

Acorns Bonus Link 

Which Small Cap Value Funds Are Best for You?

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Jason asks (at 02:24 minutes):   Is it possible that my simple portfolio is already outperforming the efficient frontier? Or am I misinterpreting the data?

I’ve been intrigued by the efficient frontier discussions over the past year, especially episode 577, where Joe helped a listener named Kelsey work through limited 401(k) options. As a public safety officer, I’m in a similar position. 

I have access to both a 457(b) and a 401(a), plus a pension that’ll provide a guaranteed income. So, I’ve been fairly aggressive with a 90/10 stock-to-bond allocation. According to Portfolio Visualizer, this mix has an expected return of 13.22 percent with a standard deviation of 14.33.

To compare, I asked ChatGPT to create a 90/10 allocation that would fall on the efficient frontier, using the funds available in my 401(a). It suggested 25 percent S&P 500, 25 percent large cap growth, 15 percent mid cap, 15 percent small cap, 10 percent international, and 10 percent bond.

But here’s the twist: when I plug that allocation into Portfolio Visualizer — using the 30 percent max weight guideline — the expected return drops to 12.9 percent with a higher standard deviation of 16.75. 

When I match the standard deviation of my current portfolio (14.33), the return drops even further to 11.65 percent, which seems contrary to what I’ve taken from your episodes. I thought the efficient frontier should help me increase returns for the same level of risk? 

I’m perfectly happy with a VTSAX-and-chill approach, but if the efficient frontier really can deliver better returns at the same risk level, I’d love to understand how to take advantage of it.

Am I misinterpreting something here?

Minerva asks (at 37:20 minutes):   What’s the best way to avoid paying unnecessary taxes on investments—without doing anything shady?

As we approach retirement, my spouse and I are starting to think about where our investments live. Up until now, we’ve focused almost entirely on tax-advantaged retirement accounts, but we’re ready to build out our brokerage account to complete our tax triangle.

That brings up a big question: Which types of funds belong in each type of account? 

Which investments are better off in IRAs or 401(k)s because they generate high tax drag? And which ones are more efficient to keep in a taxable brokerage because they throw off minimal gains along the way?

We’d appreciate a deep dive into tax-efficient asset placement—especially for those of us closing in on retirement.

Scott  asks (at 01:19:19  minutes): Do you have any straightforward resources that explain the efficient frontier and offer actionable steps for someone ready to move beyond a basic index fund strategy?

I appreciated Joe’s thoughtful take on the “VTSAX and chill” approach versus optimizing for the efficient frontier. I’m intrigued by the idea of taking 15 minutes to shift my portfolio toward something more efficient—but I’m not sure where to start. 

Part of the appeal of VTSAX is how simple and clearly defined the steps are, thanks to JL Collins. Are there any articles, videos, or guides that simplify the efficient frontier in the same way?

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The Bureau of Labor Statistics issues massive job revisions on Friday morning. The revisions wipe out nearly 90% of previously reported gains for May and June. This raises fundamental questions about how our most trusted economic data gets calculated.

Friday arrives. The BLS delivers what appears routine: 73,000 new positions added in July. But the revisions tell a different story. May’s initially reported 144,000 job gains become 19,000. June’s seemingly solid 147,000 drops to just 14,000. These represent 87-90% overestimates. They fundamentally alter the economic picture for those months.

The BLS surveys 560,000 businesses each month. They use payroll data from the 12th of the month. But only 60-73% of those businesses respond by the initial release deadline. The remaining portion gets filled through statistical modeling. The models rely on historical patterns.

This approach typically produces revisions in the 20,000-50,000 range. But throughout 2025, average monthly revisions reach 66,000. That’s triple the normal size. The statistical models aren’t capturing current economic conditions effectively.

The problem becomes clear when economic conditions shift rapidly. Historical patterns become unreliable guides. The 2024 annual revision was the largest since 2009. What happened in 2009? The Great Recession. Another period when traditional forecasting tools struggled with rapid change.

ADP is a private payroll processor. They serve 460,000 companies. They provide useful comparison data. For May, their 37,000 private-sector job estimate aligns reasonably well with BLS’s revised 19,000 total. For June, ADP reports a 33,000 job loss. BLS shows a 14,000 gain.

ADP’s independent data helps validate the revised numbers while highlighting the magnitude of the initial errors.

These numbers drive real decisions. Federal Reserve officials use employment data for interest rate policy. Investors allocate capital based on these reports. Workers make career decisions based on perceived labor market strength.

When the initial data misses by 90%, everyone operates with fundamentally flawed information.

The revisions expose how fragile our economic measurement systems become when conditions change faster than models can adapt.

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Interesting observations about the current housing market, meme stocks (again), GDP, Fed Meeting, Stock Market, and the latest Jobs Report updates. 

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 Introduction to Economic Turmoil 

01:21 Jobs Report According to the BLS 

09:23 Impact of Tariff Negotiations 

12:36 The Broader Trade Landscape 

16:04 Stock Market Reactions 

24:11 GDP and Inflation Insights 

31:52 The Fed’s Steady Hand (Interest Rates) 

39:55 Housing Market Dynamics 

39:40 Affordability Crisis in Real Estate 

50:23 The Return of Meme Stocks 

Resource mentioned: 

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Here’s the thing about personal finance advice: what works when you have $10,000 won’t work when you have $1 million. 

Yet most financial guidance treats everyone the same, whether you’re scraping together a $1,000 emergency fund or deciding whether to upgrade to business class.

Nick Maggiulli, author of “The Wealth Ladder,” joins us to break down how money strategies must evolve as your net worth grows. He’s mapped out 6 distinct wealth levels, each requiring different approaches to spending, saving and investing.

The levels start simple. 

Level 1 covers anyone with less than $10,000 in net worth — that’s 20 percent of American households. Here, bad luck gets amplified. A flat tire that costs $200 could spiral into job loss and debt if you can’t afford the repair.

Level 2 spans $10,000 to $100,000 in net worth. Maggiulli calls this “grocery freedom” — you can splurge on the nicer eggs without checking your bank balance. 

Level 3, from $100,000 to $1 million, brings “restaurant freedom.” 

Level 4, the $1 million to $10 million range, unlocks “travel freedom.”

Getting beyond Level 4 — into the $10 million-plus territory — requires business ownership or extreme patience. Maggiulli calculates that even saving $100,000 annually after hitting $1 million takes 23 years to reach $10 million, assuming 5 percent annual returns.

The data shows income matters more than frugality, especially in the early levels. The median household income in Level 1 is $32,000, but in Level 4 it’s $197,000, and in Level 6 it reaches $4.3 million.

We discuss why homeownership dominates wealth in Levels 2 and 3, how investment assets become crucial in higher levels, and why many people in Level 4 choose “Coast FIRE” over the grinding path to Level 5.

Resources mentioned:

The Wealth Ladder Book

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You follow all the right personal finance advice. You know you should save more, invest regularly, and build an emergency fund. 

So why does it feel so much harder for some people than others?

The answer lies in your personality.

Dr. Sandra Matz, a professor at Columbia Business School, studies the intersection of psychology and money management. She joins us to explain why one-size-fits-all financial advice often fails.

Her research found that agreeable people — those who are caring, empathetic, and put others first — have a harder time saving money. 

The solution isn’t better budgeting apps or stricter rules. It’s reframing financial goals to match your personality type. 

For example, agreeable people save more effectively when they view their emergency fund as protection for loved ones or a way to help others during tough times. 

By contrast, competitive personalities respond better to framing savings as getting ahead in life.

This personalized approach extends beyond personality assessments. Algorithms can now predict your financial behavior using digital footprints — social media activity, spending patterns, even smartphone usage. With just 300 Facebook likes, artificial intelligence understands your money habits better than your spouse does.

The conversation also covers the darker implications. Companies exploit these same psychological insights to manipulate spending decisions. Dr. Matz discusses data cooperatives as a solution — member-owned entities where people collectively benefit from their shared information.

We dive into negotiation strategies for salary increases, breaking out of financial echo chambers, and using AI to optimize your money management without losing your decision-making autonomy.

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) Big data meets financial psychology

(3:34) Psychology and computer science intersection

(6:26) Algorithms vs spouses at predicting personality

(7:21) Curly fries predict intelligence

(9:01) Self-talk reveals emotional distress

(11:04) Nice people struggle with money

(14:03) Personality-based savings strategies

(22:21) Privacy versus convenience tradeoffs

(24:36) Data privacy management burden

(26:28) Organ donation defaults

(30:40) Data cooperatives concept

(36:01) ChatGPT for financial advice

(40:04) AI as unlimited intern

(44:06) Breaking financial echo chambers

(53:14) AI negotiation training

Resources Mentioned

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Jlyn and her husband are 20 years from retirement, but they’ve got their eye on a second home they’ll live in when the time comes. Should they make the purchase now, or keep saving?

Reese was recently laid off, and she’s struggling to choose between two financially responsible paths. Should she continue her long-term disability insurance? Or is it wiser to save money?

Kip’s youngest has finally graduated from college, and he’s looking forward to an early retirement. But, with the eyewatering costs of long-term healthcare, is this still a viable path? 

Former financial planner Joe Saul-Sehy and I tackle these three questions in today’s episode.

Enjoy!

P.S. Got a question? Leave it here.

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Jlyn asks (at 02:31 minutes):  How do you balance competing financial goals when you’re doing well, but want to do even better?

My husband and I are both 41, with three kids ages 8, 11, and 13. I’m a physician, and he works as a commercial project manager. Together, we earn $350,000 a year. We tithe 10 percent, invest 18 percent, and still have a $3,000 monthly surplus after all our expenses.

Our primary home is worth over $1 million, with a $550,000 mortgage that we expect to pay off by retirement. We’ve already paid off $300,000 in med school debt, so aside from the mortgage, we’re debt-free. 

We’ve saved $500,000 toward retirement so far, and our kids’ 529s are funded by a $980/month rental on part of our home. We’re on track to retire around age 60 to 62, and now we’re wondering whether to buy a second property. 

We’d like to use it extensively in retirement, and it could also serve as a short-term rental for now. But we’re also juggling other goals—saving for college, cars, weddings, and continuing to build our retirement accounts.

How should we prioritize between investing our surplus and purchasing a second home? And what are the biggest financial risks we should watch out for when considering a lifestyle-based second property that we hope to eventually use for part of the year in retirement?

But should I also continue paying for the long-term disability insurance offered through my former employer? 

Realistically, it could take six months to a year to find a new job. And while the risk of needing healthcare during that time feels high, the risk of becoming disabled long-term seems much lower.

So here’s my question: Should I drop the long-term disability coverage for now, and if my next employer doesn’t offer it, look into buying it on the private market? Or is there an advantage to sticking with the same plan and provider for continuity’s sake? 

With health insurance, switching means resetting your deductible—but I don’t think that’s the case with disability insurance. What should I know about switching disability policies, and how should I weigh the cost versus the risk?

Kip asks (at 40:55 minutes): What’s the smartest way to prepare for the massive cost of long-term care, especially if you’d rather retire now?

I’m 47, my wife is 48, and we live in a western suburb of Atlanta. Our youngest just finished college, and I’d like to retire, mainly because I hate my job. But it pays well, so I’ve kept at it. We live very frugally, and I could cover our current expenses if I quit now. 

The problem is long-term care. Skilled nursing facilities in our area cost around $10,000 a month per person. That’s $20,000 a month if both my wife and I ever needed it. Based on the four percent rule, I know I can’t afford that.

I’ve looked into long-term care insurance, but the cost, vague terms, and potential for rising premiums make me skeptical. It seems like the most responsible thing to do is to keep working so I can self-fund those future costs. 

And if we never need it, the money could become an inheritance for our kids. Is that the right move—or is there a better way to approach this?

Resources Mentioned:

#417: Ask Paula: Marriage and Money – What Are the Right Conversations?

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A software programmer and an accountant walk into retirement planning. Are they being creative? Dr. Zorana Ivcevic Pringle, a senior research scientist at Yale University’s Center for Emotional Intelligence, says absolutely.

Pringle defines creativity as something that’s both original and effective, whether you’re solving an accounting problem or planning an unconventional retirement.

We explore the gap between having ideas and actually implementing them. You have this brilliant vision for starting a business, changing careers, or retiring early, but somehow you never take the first step. Pringle calls this the implementation gap, and she explains why it happens.

The conversation centers on a hypothetical couple: both 55 years old, one a programmer, the other in middle management. They want to retire at 57 and travel the world. Pringle uses this example to illustrate how creative problem-solving works in real life.

She explains that creativity requires comfort with uncertainty. When you’re doing something new, you don’t have a blueprint or checklist. There’s always the risk that your early retirement plan could fail spectacularly — imagine having to return to work at 59 after the market tanks and your portfolio gets crushed.

Here’s the key insight: you don’t need full confidence to start. Pringle compares creative confidence to fuel in a car. You don’t need a full tank — you can start with just a quarter tank and refuel along the way. Each small success builds more confidence for the next step.

The bottom line? Innovation happens through constant iteration. Your final destination might change throughout your career and retirement, and that’s completely normal. 

Resources Mentioned:

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) Implementation gap intro

(1:00) Creativity beyond arts

(2:00) Original plus effective

(3:00) Ideas to action gap

(5:00) Retirement as creativity

(7:00) Openness drives creativity

(8:00) Problem finding process

(10:00) Big Five traits

(12:00) Openness and creativity

(15:00) Traits can change

(18:00) Uncertainty creates risk

(20:00) Courage versus comfort

(23:00) Self-efficacy challenges

(25:00) Quarter tank confidence

(28:00) Creative failure recovery

(32:00) Creative blocks

(36:00) Pivoting versus quitting

(39:00) Emotions as information

(42:00) Metrics versus intuition

(50:00) Implementation strategies

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