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?
Rob asks (30:10): If your portfolio already includes a large chunk of income-producing real estate, do you still need bonds?
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?
Dan asks (42:28): What if, instead of retiring, I bought a small business to replace my day job?
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 Katie Gatti Tassin
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