The Business Owner's Dilemma: Reinvest or Diversify?

Your business might be the best investment you'll ever make. But at what point should you stop putting everything back into it and start building wealth elsewhere?In this episode , Bob Fraser and Ben Fraser tackle a dilemma nearly every successful entrepreneur faces: when to keep reinvesting in your business and when to start diversifying.Bob shares lessons from losing millions in the dot-com crash, including why he wishes he'd taken money off the table sooner. They discuss the risks of having too much wealth tied to one business, how much to set aside for passive investments, and why building wealth outside your business is essential for long-term financial security.They also explore the role of alternative investments, the importance of liquidity, and how to gradually shift from actively building a business to creating a portfolio that can support you without it.Enjoyed this episode? Hit follow so you never miss a new episode. If you found it valuable, leave us a rating and send this episode to someone who should hear it.Have a question for the show or want more resources, including our tax calculator? Visit ⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  to explore more and join our community.Want to invest alongside Ben, Bob & Ellis? Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/

What can individual investors learn from the world's largest endowments? And how can you apply those same investment strategies to your own portfolio?In this episode of Invest Like a Billionaire, Ellis Hammond sits down with Wendy Li, Co-Founder and CIO of Ivy Invest, who has spent her career managing institutional investment portfolios, including overseeing a $4 billion portfolio at the Mother Cabrini Health Foundation.Wendy shares how endowments build resilient portfolios, manage risk, and invest for long-term growth.In this episode, you'll learn:How endowments approach asset allocation and diversificationWhy institutions invest in private markets and alternative investmentsHow to balance risk, returns, and liquidityHow to apply institutional investment strategies to your own portfolioEnjoyed this episode? Hit follow so you never miss a new episode. If you found it valuable, leave us a rating and send this episode to someone who should hear it.Have a question for the show or want more resources, including our tax calculator? Visit ⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  to explore more and join our community.Want to invest alongside Ben, Bob & Ellis? Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/

What does overseeing $11 billion in retirement assets teach you about building and protecting wealth?David T. Yu is a financial advisor and airline pilot who served on a five-member pension committee overseeing approximately $11 billion in retirement assets. Today, he helps high-income earners navigate wealth management, alternative investments, and tax planning.David joins Ellis Hammond to explain why he believes investors need more than traditional stocks and bonds, how alternative investments like private credit and real estate can help diversify a portfolio, and what high earners often overlook when it comes to taxes.Plus, he shares how his firm helped a client defer a $6 million tax bill for up to 21 years.If you're earning great money and looking to build, diversify, and protect your wealth, this conversation is for you.Enjoyed this episode? Hit follow so you never miss a new episode. If you found it valuable, leave us a rating and send this episode to someone who should hear it.Have a question for the show or want more resources, including our tax calculator? Visit ⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  to explore more and join our community.Want to invest alongside Ben, Bob & Ellis? Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/

From the Vault: We’re bringing back our most-watched episode ever, edited down to the best moments. How do you build a family office without being a billionaire? Jim Dew breaks down the virtual family office model and how successful entrepreneurs and high net worth investors can take a more coordinated approach to wealth management.We get into alternative investments, asset allocation, portfolio diversification, choosing the right financial advisors, and why the strategy that helps you build wealth may not be the same strategy that helps you preserve it.This conversation was originally released in 2023 and has been condensed and re-edited for this From the Vault edition.Enjoyed this episode? Hit follow so you never miss a new episode. If you found it valuable, leave us a rating and send this episode to someone who should hear it.Have a question for the show or want more resources, including our tax calculator? Visit https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  to explore more and join our community.Want to invest alongside Ben, Bob & Ellis? Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/

Cody Barbo, founder and CEO of Trust & Will, joins Ellis Hammond to talk about building, investing, and protecting wealth.Cody shares how he thinks about having most of his net worth tied up in the company he built, what raising more than $80 million taught him about choosing investors, and how he plans to diversify after a future liquidity event.Plus, Cody breaks down estate planning, including wills vs. trusts, when you actually need a trust, and how to protect and pass down the wealth you’ve worked hard to build.Enjoyed this episode? Hit follow so you never miss a new episode. If you found it valuable, leave us a rating and send this episode to someone who should hear it.Have a question for the show or want more resources, including our tax calculator? Visit ⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  to explore more and join our community.Want to invest alongside Ben, Bob & Ellis? Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/

Making a high income doesn’t automatically make you wealthy.For high-income earners, the challenge often isn’t making more money, it’s turning that income into assets that compound and create long-term financial freedom.In this episode of Invest Like a Billionaire, Ben Fraser and Ellis Hammond break down how to make the shift from earning a great income to actually building wealth. They discuss lifestyle creep, debt, taxes, investing, and why getting to your first $1 million in investable assets can be such an important milestone.They also cover the short-term rental tax strategy many high earners overlook, how to “pay yourself first,” why protecting against losses matters when you’re building your portfolio, and the mindset shift from focusing on your income to focusing on your balance sheet.If you’re a high-income earner who wants to put your money to work and accelerate your path to financial freedom, this episode is for you.Enjoyed this episode? Hit follow so you never miss a new episode. If you found it valuable, leave us a rating and send this episode to someone who should hear it.Have a question for the show or want more resources, including our tax calculator? Visit ⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  to explore more and join our community.Want to invest alongside Ben, Bob & Ellis? Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/

Is the multifamily market finally at the bottom? After years of rising interest rates, falling property values, and distress across commercial real estate, the data may be pointing to a major buying opportunity.In this episode, Bob Fraser, Ben Fraser, and Ellis Hammond break down the current state of the multifamily market, the nearly $800 billion maturity wall, where distress is actually showing up, and why they believe the bottom is here.They also explain why today’s higher interest rates could create a unique buying window, how inflation impacts real estate over the long term, and why borrowing costs are temporary, but your basis is forever.Enjoyed this episode? Hit follow so you never miss a new episode. If you found it valuable, leave us a rating and send this episode to someone who should hear it.Have a question for the show or want more resources, including our tax calculator? Visit ⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  to explore more and join our community.Want to invest alongside Ben, Bob & Ellis? Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/

What does it actually take to find a good private market deal?Aleksey Chernobelskiy, founder of GP-LP Match, joins Ben Fraser and Ellis Hammond to break down what he’s seeing across private markets today, from the biggest mistakes investors make to the risky assumptions hiding in real estate deals.Plus, why sophisticated investors may look at dozens of deals before saying yes to one.Enjoyed this episode? Hit follow so you never miss a new episode. If you found it valuable, leave us a rating and send this episode to someone who should hear it.Have a question for the show or want more resources, including our tax calculator? Visit ⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  to explore more and join our community.Want to invest alongside Ben, Bob & Ellis? Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/

Private alternatives are becoming a bigger part of high-net-worth portfolios. Is your advisory practice keeping up?Ellis Hammond sits down with Steve Woodruff, Principal and CIO of Venture Financial Advisors, to discuss why investor demand for private alternatives is growing and what RIAs need to know to stay competitive. They cover how to incorporate private markets into client portfolios, evaluate managers, conduct due diligence, and navigate opportunities across private credit, private equity, energy, and more.Enjoyed this episode? Hit follow so you never miss a new episode. If you found it valuable, leave us a rating and send this episode to someone who should hear it.Have a question for the show or want more resources, including our tax calculator? Visit ⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  to explore more and join our community.Want to invest alongside Ben, Bob & Ellis? Learn more at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/

China has a repeatable playbook for dominating entire industries. And now, it’s targeting sectors critical to America’s economic future.In this episode, Bob Fraser, Ben Fraser, and Ellis Hammond break down the strategy outlined in Ram Charan’s China’s 90% Model, how China gained control of critical industries like rare earth minerals, and why AI could be the next major battleground.Is the U.S. prepared to fight back? And what does this growing economic battle mean for investors?Have more questions, or want more resources like a tax calculator? Go to ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://investlikeabillionaire.org/⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  to learn more about our community. Check out Ben & Bob’s company and invest along at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://aspenfunds.us/