Money Tree Investing

Mark Flickinger shares his journey from engineering and building small businesses to working in private market investing at BIP Capital, where he helps both entrepreneurs and high-net-worth investors achieve their goals. He explains that private markets have grown as many high-quality companies remain private longer, creating opportunities for alpha that are less available in public markets, especially as IPO thresholds have risen. Flickinger highlights trends in alternatives, noting that while AI attracts attention, compelling private businesses can now be accessed at lower entry costs.

We discuss...

• Mark Flickinger combines his engineering background with investment expertise to support both business owners and high-net-worth investors.
• Private markets have grown in importance as alternatives, moving beyond hedge funds to include a wide range of private companies.
• Value creation that once happened in small-cap public stocks is now largely occurring in private companies.
• Only one out of ten U.S.-based companies with $100 million or more in revenue is public, leaving most growth in private markets.
• Entrepreneurs increasingly stay private due to regulatory burdens and the ability to grow without going public.
• Business development companies (BDCs) were created to simplify private market investing for U.S.-based companies and investors.
• Entrepreneurs are increasingly using a hybrid approach of equity and debt to raise capital without overly diluting ownership.
• Taking on a partner or investor is worthwhile if they bring expertise and add significant value to the business.
• Debt can be advantageous if the business grows faster than the interest cost, making leverage an effective tool.
• Capital should be taken strategically to overcome growth hurdles, not just for the sake of raising funds.
• Many business owners excel in specific phases of growth and benefit from focusing on their strengths rather than the CEO role.
• The private credit market is likely to expand further, while banks continue to reduce direct lending to businesses.
• A robust AI plan is now a key factor in evaluating a company's long-term potential, beyond just naming conventions.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Diana Perkins | Trading With Diana

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For more information, visit the show notes at https://moneytreepodcast.com/private-market-investing-mark-flickinger-740

It looks like the market is going on vacation! Well I am too. Today we talk everything from vacation plans to shifting markets. We also cover recent crypto volatility, the resilience of Bitcoin, and concerns over MicroStrategy's stock dilution strategy, framing dips as potential buying opportunities within broader trends. We chat on quirky social trends in China, like "pretend to work" jobs for unemployed youth, and highlight Ray Dalio's view that real estate is a poor investment in today's environment with recent price drops accorss the U.S. Today we discuss...

• Media narratives often obscure the real developments happening quietly in the background.
• Stablecoins are emerging as a substitute for the dollar and could diminish banks' central role in the financial system.
• This shift resembles the fragmented multi-currency era before the creation of the Federal Reserve.
• Recent crypto markets have been volatile, with Bitcoin showing resilience despite sharp pullbacks.
• Ray Dalio argued that real estate is a poor investment today due to its interest rate sensitivity and immobility.
• U.S. real estate markets are already showing significant price declines in several regions.
• The administration is talking up lower rates, Trump has pushed cuts, and Powell left rates unchanged at the last meeting.
• Market behavior appears disconnected from economic data, undermining the usefulness of traditional reports.
• Government statistics are viewed as unreliable, with references to Shadow Stats' alternative takes on CPI history.
• Given data doubts, the focus should be on how markets and investor sentiment actually react.
• Seasonally, mid-August to mid-November is typically weak, and the second year of a presidency often underperforms.
• August and September have historically been the S&P 500's weakest months, while 2025 has so far outperformed typical post-election patterns.
• Personal spending is slipping, and fast-casual chains' same-store sales have fallen since Q4, suggesting strain.
• Housing and renovation activity looks softer versus the last five years but closer to pre-2020 norms—a reversion to the mean, not necessarily recession.
• Student loan and credit-card delinquencies are spiking, hinting at cash-flow stress that clashes with low unemployment data.
• Tariff revenues jumped from roughly $8B/month to about $29.6B/month, with companies largely absorbing costs so far.
• Money is chasing select commodities like gold, silver, and uranium, while others like lithium lag and could move with China trade shifts.
• The dollar sits mid-range historically and could sink on aggressive cuts, though today's "broken" market dynamics muddy typical cause-and-effect.
• Despite risks, the market's underlying tone is bullish, so a continued climb is possible on favorable policy headlines.
• Research notes humans rate AI higher when it agrees with them, suggesting systems learn to avoid conflict and may reinforce user beliefs.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | ProCollege Planners

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For more information, visit the show notes at https://moneytreepodcast.com/market-is-going-on-vacation-739

Anders Inset is here to share on this new work The Singularity Paradox. He shares his journey from capitalist and athlete to author and shares the concept of the technological singularity and the associated risks of creating godlike, self-improving machines without fully understanding their implications. He argues for developing "artificially human intelligence" rooted in human biology to preserve humanity in the face of exponential technological growth. The discussion covers the profound transformations such advancements could bring, from curing diseases and achieving abundant energy to redefining economics, ethics, and human purpose, while warning about dangers like hyper-efficiency, mass unemployment, wealth inequality, and societal instability.

We discuss...

• Anders shares his background as a former capitalist and athlete turned author of seven books blending science, philosophy, and technology.
• His latest work, The Singularity Paradox, examines the point where AI surpasses human intelligence and the risks of creating godlike, self-improving machines.
• Inset sees the singularity as a transformational moment possibly within 10–20 years, reshaping medicine, energy, ethics, and human purpose.
• He warns that AI's exponential growth leaves little room for error correction compared to past technologies.
• Potential benefits include curing diseases, abundant energy, and space exploration, but risks include hyper-efficiency eliminating human labor.
• This efficiency could lead to massive unemployment, extreme wealth inequality, and the need for new wealth distribution models.
• Inset is more concerned about societal impacts than "killer robot" scenarios, seeing existential risks alongside massive opportunities.
• The conversation explores whether humanity can responsibly slow or control AI development, drawing comparisons to nuclear weapons and cloning.
• Global governance is needed to regulate emerging technologies like biotech, AI, and quantum computing to avoid uneven playing fields.
• Advancements in biotechnology may soon enable life extension and age reversal, raising profound questions about human purpose.
• Investment opportunities exist in health tech, decentralized finance, and quantum computing, but risk levels vary widely.
• The decentralized financial system could disrupt traditional monetary structures, but it carries geopolitical risks.
• Quantum computing threatens current cryptographic security, posing challenges for cryptocurrencies like Bitcoin.
• Humanoid robots may create a new consumer market with personalized features and subscription services.
• AI's current impact is limited mostly to process optimization and customer support, with larger economic effects expected by 2026.
• Scientific breakthroughs in energy storage and new materials will likely drive new business models.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance

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For more information, visit the show notes at https://moneytreepodcast.com/the-singularity-paradox-anders-indset-738

Is private equity destroying your favorite consumer products? Today we discuss economic news, recent Trump-era tariffs, and private equity. We touch on corporate profit margins, wage growth versus price increases, and how different industries—like autos—are affected unevenly. We also explore interest rates and the possibility that traditional cause-and-effect in markets is "broken," questioning whether metrics like CPI, GDP, and rate changes meaningfully influence market behavior anymore, given recent patterns where markets defy economic logic.

We discuss...

• Recent economic updates included the rollback of several Trump-era tariffs, though many remain in place.
• Companies are currently absorbing most tariff-related costs instead of passing them directly to consumers.
• Concerns were raised that if companies start passing these costs along, price increases could hit consumers later in the year.
• Wage growth trends are compared with rising prices, raising questions about future consumer spending strength.
• Industry impacts from tariffs vary, with the auto sector singled out as experiencing specific pressures.
• Recent market resilience even in the face of economic data could historically trigger volatility or declines.
• Earnings reports no longer move markets as much because companies lower expectations to easily beat estimates.
• The focus on quarterly earnings is misleading; long-term company growth matters more on an individual level but less on a macro scale.
• Value investing has underperformed for about 20 years because fundamentals matter less in today's market.
• The Fed's interest rate tools are less effective because global capital flows and supply shocks weaken their control.
• The Fed can still cause recessions by raising rates too high but can't fine-tune the economy like before.
• Supply-driven inflation (like energy and supply chains) is less responsive to Fed rate hikes.
• Market rates often lead Fed policy, meaning bond traders set financial conditions before the Fed acts.
• Private equity often overleverages companies, leading to bankruptcies despite popular products, like Instapot.
• Private equity uses dividend recapitalization to extract value quickly, saddling companies with unsustainable debt.
• Examples like Sears, Joanne Fabrics, Red Lobster, and Toys "R" Us show how private equity can ruin beloved brands.
• Private equity has been successful for investors but often at the expense of the long-term health of companies.
• Financial planning for college funding is increasingly critical given new loan limits and repayment changes.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | ProCollege Planners

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For more information, visit the show notes at https://moneytreepodcast.com/favorite-consumer-products-737

Vincent Zurzolo shares his journey in investing in comic books. Vincent shares his lifelong passion for comics, which he turned into a successful business that has sold some of the most expensive comic books in history, including multiple million-dollar issues. We discuss how comic books have evolved from casual childhood reads to serious investments, and how third-party grading and online auctions have expanded the market. He emphasizes that comics—whether for fun, art, or investment—are still thriving.

We discuss...

• Vincent Zurzolo is the president and co-owner of Metropolis Collectibles and ComicConnect.com, leading companies in the vintage comic book market.
• He began collecting and selling comics at 15 and turned his passion into a multimillion-dollar business.
• His companies have sold some of the most expensive comics in history, including several copies of Action Comics #1 and Amazing Fantasy #15.
• Third-party grading, pioneered by his team, has made comics more accessible and investable for collectors worldwide.
• ComicConnect hosts regular online auctions featuring vintage comics, original comic art, and rare collectibles.
• Digital platforms like VeVe are changing how comics are collected, using NFT-like tokens to sell limited digital editions.
• The global comic market is expanding, with increasing interest in foreign editions and international collectors.
• Manga has become the most popular comic format globally, embraced by fans across cultures and countries.
• Original comic art—drawings used to create comic book pages—is a growing collectible category with high demand.
• People collect comics and art in creative ways, from themes like holidays and sports to specific characters or artists.
• Graphic novels, while popular and accessible, generally don't carry the same investment value as vintage comics.
• The comic book market offers entry points for all budgets, from dollar-bin finds to million-dollar grails.
• Zurzolo sees comic books as a major American art form that teaches vocabulary, inspires careers, and sparks imagination.
• He believes comic book movies will continue to thrive, despite variability in quality like any genre.
• He encourages people to read comics not just for collecting, but for joy, creativity, and escapism.

For more information, visit the show notes at https://moneytreepodcast.com/investing-in-comic-books-vincent-zurzolo-736

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Phil Weiss | Apprise Wealth Management

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Here's what not to do when buying a house! Today we explore my experience with buying a home. We also talk about what it means to be "anti-fragile" in markets that look stable but are actually full of hidden risks. We unpack why markets feel eerily calm despite cracks under the surface, point to red flags like rising margin debt and overvalued equities, and question the rosy government data that doesn't match what businesses are actually seeing. We also touch on the Fed's latest rate hold, the performative nature of their messaging, and why Japan might be the next weak link in the global system.

We discuss...

• We talk about how fragile markets can appear strong but collapse under pressure, while anti-fragile strategies are built to withstand shocks.
• There's growing skepticism around official data on inflation, unemployment, and job growth, which often don't match real-world experiences.
• We flag early warning signs like record-high margin debt and stretched market valuations that suggest hidden fragility.
• The Buffett Indicator is flashing red, pointing to historically high levels of overvaluation.
• We discuss how investors often chase all-time highs without considering the risks beneath the surface.
• The Fed paused interest rate hikes again, but its messaging feels more performative than predictive.
• Government job growth is outpacing private sector job growth, raising questions about the true health of the economy.
• Markets are euphoric about all-time highs, but this sentiment overlooks growing risks and valuation distortions.
• There's a widespread misunderstanding of the difference between correlation and causation in market data and recessions.
• Long-term market growth trends can be distorted by short-term performance comparisons, leading to misleading "chart crimes."
• Used car prices remain high, partly due to ongoing shortages and strong demand, especially for 2–3-year-old vehicles.
• Housing affordability has worsened dramatically, with mortgage costs far outpacing rent, making ownership financially unappealing.
• Personal experience with deceptive sellers reflects broader issues in the housing market's transparency and ethics.
• As interest rates fall, more inventory may hit the housing market, but price drops are likely in many regions.
• Homeownership is a personal expense, not an investment, due to ongoing maintenance, taxes, and volatility.
• Homeownership comes with hidden costs and liabilities that are often underestimated by buyers.
• The financial burden of owning—repairs, maintenance, interest—can reduce or erase the perceived gains over time.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | Mergent College Advisors

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For more information, visit the show notes at https://moneytreepodcast.com/what-not-to-do-when-buying-a-house-735

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Doug Lynam is here today to share about his new book, Taming Your Money Monster. Doug shares his unconventional life journey from a Marine Corps officer to a Benedictine monk for 20 years, where he confronted the inescapability of money even in a monastery and how he later transitioned to become a professional money manager focused on teaching healthier, ethical relationships with money. He discusses how people develop "money monsters"—unhealthy money habits tied to psychological attachment styles. He stresses that while thriftiness is valuable, it should not come at the cost of compassion or love.

We discuss...

• Doug explains his "attachment theory of money," comparing unhealthy money relationships to attachment styles in psychology, with anxious and avoidant money behaviors.
• He highlights how people often show mixed money attachments across the four pillars of finance: earning, saving, investing, and giving.
• Doug reflects on his monastic life as a quest to understand the meaning of life and spiritual unity, which influences his compassionate approach to money.
• They discuss the impact of upbringing on money attitudes, using Doug's father as an example of anxious earning and avoidant saving driven by early scarcity and trauma.
• Kirk and Doug talk about cultural and generational influences on thriftiness and money control, including weaponizing money as a form of control.
• They explore parenting approaches, emphasizing the importance of setting firm but loving boundaries to teach children respect for money and responsibility.
• Doug warns against conditional love based on behavior, advocating for unconditional affection alongside clear consequences.
• Doug introduces the Enneagram personality system as a key tool in understanding financial behaviors and emotional patterns related to money, promising to explain it further.
• Unlike the more fixed Myers-Briggs system, the Enneagram offers a fluid growth framework that guides emotional and spiritual development over time.
• Personal experiences with anger are shared, highlighting how generational values around toughness and self-control shape how anger is handled.
• The Enneagram is described as having a spiritual layer that underpins common virtues found in many religions, such as honesty and courage.
• Doug stresses that meaningful transformation takes effort and mental work—there are no quick fixes—and that sustained self-awareness and practice are essential.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Douglas Heagren | Pro College Planners

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For more information, visit the show notes at https://moneytreepodcast.com/taming-your-money-monster-doug-lynam-734

It's a Crypto Bonanza today we we discuss the new Clarity Act and how it impacts digital currencies. We also chat about the emotional and financial rollercoaster of buying a home in today's market, as Kirk shares about falling in love with a house—only to walk away after discovering many issues the sellers failed to disclose. We talk about how the cost to buy is now far above the cost to rent in many areasb and how sellers are increasingly unwilling to drop prices—even as supply builds and interest rates stay high. We also dig into how real estate, while deeply emotional, ultimately comes down to math, and why renting may still make more sense...

Wee discuss...

• The cost to buy a home is currently much higher than the cost to rent, especially in higher-priced markets.
• Emotional attachment often causes sellers to keep unrealistic home prices despite market shifts.
• Many markets are seeing a growing supply of homes and longer times on market, leading to price pressures.
• Real estate equity is a major source of wealth but is difficult to access without selling or borrowing.
• Sellers tend to suppress or avoid disclosing problems to preserve home value, increasing risk for buyers.
• Inflation-adjusted home prices show 2025 prices are very high, but official inflation numbers may understate true inflation.
• Buying a home is often an emotional and personal decision rather than a purely financial investment.
• Renting can be mathematically cheaper, but many still desire homeownership for personal reasons.
• The Clarity Act aims to define regulatory authority over digital assets between the CFTC and SEC, though it hasn't passed yet.
• Regulation is viewed positively if it prevents fraud without overly restricting innovation in crypto.
• The banking sector may resist crypto innovation due to potential threats to their traditional business models.
• Concerns were expressed about government overreach via CBDCs that could control or monitor personal spending.
• Despite risks, the government already has many tools to combat financial crime without needing intrusive surveillance.
• Bitcoin and Ethereum prices have risen recently, prompting some profit-taking but maintaining belief in long-term value.
• MicroStrategy pivoted to Bitcoin investment after years of flat or breakeven performance, using debt and financial engineering to buy more Bitcoin.
• The history of MicroStrategy's CEO includes a past SEC investigation and company struggles before embracing Bitcoin.
• The line between genius and stupidity can sometimes be just dumb luck.
• MicroStrategy's strategy resembles a Ponzi scheme by relying on new money to pay returns and leveraging debt to buy Bitcoin.
• If Bitcoin crashes, the company faces margin calls and financial stress due to heavy debt.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | ProCollege Planners

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For more information, visit the show notes at https://moneytreepodcast.com/crypto-bonanza-733

Shaan Patel is here to discuss how you can slash the cost of college through some more advanced strategies. We also discuss major education changes packed into the "Big Beautiful Bill," starting with the introduction of new Trump Accounts—a kind of IRA for minors with no deductions and withdrawal restrictions until age 18. We cover expanded uses for 529 plans, including tutoring, test prep, homeschool materials, and more. Repayment options are narrowed down to just two, and several popular income-driven plans are scrapped.

We also talk about how Pell Grants are being expanded for short-term workforce programs and the future of the Department of Education as it sees deep funding cuts—all pointing to less federal support, more private lending, and a growing need for serious college planning.

We discuss...

• Major education reforms packed into the "Big Beautiful Bill," starting with the new Trump Account—a savings vehicle for minors with a $5,000 annual cap, no deductions, and no early withdrawals.
• The bill expands 529 plans to cover tutoring, test prep, online learning, homeschool materials, and special education services.
• A new federal tax credit scholarship program allows individuals and corporations to donate up to $1,700 annually to scholarship organizations, with a 100% tax credit.
• There's also $500 million in grants for "American Values" curricula promoting patriotism and national pride.
• On the college side, new federal loan caps include $100K for master's degrees, $200K for professional degrees (like law or med school), and a $257,500 lifetime limit—while Grad PLUS loans are eliminated entirely.
• Repayment options are now limited to a standard plan or a new Repayment Assistance Plan (RAP), ending other income-based programs like SAVE and PAYE.
• Public Service Loan Forgiveness survives but faces tighter eligibility, and deferment options for hardship have been significantly cut.
• Workforce Pell Grants are expanded to include short-term training programs (8–15 weeks) for in-demand technical jobs.
• Wealthy universities face a major increase in endowment taxes—up to 8%—especially impacting Ivy League schools.
• The Department of Education will see a nearly 20% discretionary funding cut over five years, potentially affecting programs like TRIO that help low-income students access college.
• With fewer federal dollars and tighter lending, private loans may fill the gap—making proactive college and financial planning more critical than ever.
• Parents of younger students (7th–10th grade) should start planning early for the PSAT.

Today's Panelists:

• Kirk Chisholm | Innovative Wealth
• Barbara Friedberg | Barbara Friedberg Personal Finance
• Diana Perkins | Trading with Diana

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For more information, visit the show notes at https://moneytreepodcast.com/slash-the-cost-of-college-shaan-patel-732

Kirk changes his tune on housing as he moves towards purchasing a new home. Today we explore how homeownership is often more of an emotional choice than a smart financial investment, with many people misunderstanding the real cost compared to renting. We talk about the burden of property taxes, why paying off a mortgage early might not always make financial sense, and the social pressures around owning a home. We shift gears to a surprising discovery in credit reporting systems—a "Human Trafficking Request" option—which leads us to reflect on the serious issue of human trafficking, especially in border areas, and how complex and unexpected some financial topics can be. We also talk property taxes, economic growth, and more! Today we discuss...

• Buying a home isn't just about numbers—it's emotional, from nesting instincts to worrying about what neighbors think.
• Contrary to popular belief, owning a home often isn't a great financial investment; it's mostly a personal expense.
• There's a sweet spot where owning beats renting, but for expensive properties, renting often comes out cheaper.
• Paying off a low-interest mortgage early might feel good, but financially, investing that money elsewhere often makes more sense.
• You never really "own" a home because ongoing costs like taxes and maintenance keep coming.
• A bizarre credit bureau feature for removing human trafficking info—raises a lot of questions about what's on our reports.
• Trying to freeze or check credit reports online turned into a frustrating experience with errors and security concerns.
• A "chart crime" was discussed involving misleading silver price charts that artificially suggest massive future price spikes.
• Everyone, including experts, has biases, and the best investing involves independent thinking free from crowd influence.
• Warren Buffett's investment strategy of avoiding Wall Street noise by focusing on fundamentals is highlighted, though his recent performance is debated.
• The US stock market has outperformed international markets over the past two decades, with Europe's regulatory environment hindering growth.
• Government remains the largest job growth sector in the US, followed by healthcare, while mining, logging, and wholesale trade experience declines.
• The overarching advice is to think independently and critically about economic and investment data rather than relying solely on common narratives or biased sources.
• Silicon Valley Bank's collapse risked systemic damage due to concentrated wealth in California's tech sector and the bank's insolvency.
• Banks face difficulty raising liquidity quickly without selling assets at steep unrealized losses, causing stress in both banking and real estate markets.
• Tech giants like Apple, Microsoft, and Nvidia are performing well in earnings season, while healthcare and oil services sectors lag.
• Caution is advised against chasing recent market gains, with better opportunities expected in the fall after potential market pullbacks.

Today's Panelists:

Kirk Chisholm | Innovative Wealth Douglas Heagren | ProCollege Planners

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For more information, visit the show notes at https://moneytreepodcast.com/kirk-changes-his-tune-on-housing-731