Money Tree Investing
Today's Panelists: Kirk Chisholm | Douglas Heagren | Diana Perkins | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: Travis Jamison shares his journey from serial entrepreneur to full-time investing in legacy businesses, explaining that while tech is great for building, it’s risky for investing. He allocates capital into small, decades-old businesses via search funds, independent sponsors, and roll-ups, aiming for diversification, steady cash flow, and multiple expansion. Travis views AI less as a direct investment opportunity and more as a tool for operating...
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Kathleen Peddicord shares her experience living investing overseas. Her journey took her from publishing to becoming an authority on global real estate investing. She discusses why she prefers real estate over stocks while also outlining challenges such as lack of MLS systems, legal complexities, and cultural differences. Kathleen explained how to evaluate markets, avoid overpaying, plan exit strategies, and select properties with unique value rather than cookie-cutter developments. She stressed the importance of freehold title, sound property rights, and turnkey management solutions, while...
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Wall Street is selling beer, beaches, and barbecue. Want to invest? We also dove into the concerns about the reliability of government data. Investors should focus less on headline data and more on long-term directional trends, since recessions matter less to portfolios than actual corporate performance. We also talk labor markets, employment revisions, and rate-cut predictions, highlighting inconsistencies and the limited value of forecasts. Debt structures like extended auto loans and creative mortgages stress the importance of cash flow flexibility and smart loan structuring rather than...
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Philip Hoffman is here to share his journey from CPA to investing in fine art. He founded The Fine Art Group, where he advises wealthy families on art investing, valuations, lending, and education. He outlines the global art market as a $60 billion industry with only $6–10 billion considered truly investable, highlights the risks and pitfalls of treating art as an asset class without expert guidance, and shares cautionary tales of investors losing millions by buying discounted works without due diligence, contrasted with success stories where expertise and timing led to strong returns. We...
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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...
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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... Douglas Heagren | ...
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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...
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Douglas Heagren | Follow on Facebook: Follow LinkedIn: Follow on Twitter/X: For more information, visit the show notes at
info_outlineLaura Adams shares her journey into personal finance, podcasting, and authorship with her new book Money-Smart Solopreneur. She shares how she transitioned from corporate finance aspirations to helping individuals improve their money management through writing and podcasting. She discusses the evolution of book publishing, the growing need for supplemental income due to inflation and stagnant wages by starting side businesses, and practical advice on identifying marketable skills.
We discuss...
- Laura Adams has worked in personal finance for nearly 15 years, transitioning from a corporate finance path after noticing even smart professionals struggled with money basics.
- Her passion for financial education led her to blogging and podcasting in the mid-2000s, eventually growing the "Money Girl" community.
- Writing books is a major undertaking that requires deep effort, especially when promotion is involved.
- Her dream of seeing her book on bookstore shelves motivated her to pursue traditional publishing, despite the changing landscape of book promotion.
- How the financial pressures facing many Americans today, especially due to inflation.
- Laura encouraged people to consider starting a side business to supplement income and access tax advantages.
- Side businesses should ideally be enjoyable since they often take place during personal time.
- Starting small and testing the market with minimal upfront investment is a smart approach to launching a side hustle.
- People should leverage existing skills and interests when brainstorming side business ideas.
- If your goal is quick income, practical gigs like freelancing, tutoring, or becoming a virtual assistant may be for you.
- Many people feel intimidated by starting a business but advised against overthinking early-stage logistics.
- Wait until a side business earns around $10,000 annually before worrying about formal structures like LLCs or accountants.
- Market research through conversation can spark ideas and reveal where your talents might fill a gap.
- Iterative experimentation are a great way to discover what business ideas are both enjoyable and viable.
For more information, visit the show notes at https://moneytreepodcast.com/money-smart-solopreneur-718
Today's Panelists:
Kirk Chisholm | Innovative Wealth
Douglas Heagren | ProCollege Planners
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