This as-told-to essay is based on a conversation with Michael Chang, who runs a short-term rental business with his wife, Elizabeth and advises other professionals on investing in vacation rentals.
Claims about the size of the Chang’s portfolio and their clients have been verified by Business Insider. The interview has been edited for clarity and length.
“Oh, my son works on Wall Street,” my mom would proudly tell people.
My parents sacrificed so much to move from Taiwan to San Francisco when I was four. My dad worked at the airport, and my mom worked at a hotel in union service jobs. They helped me get an education that led me to 10 years as an M&A banker at Citi, Merrill Lynch, and Jefferies.
But after I got engaged to my wife, even before we had kids, I realized that I didn’t see how I could be a great banker and a great father.
My wife, Elizabeth, and I began renting out apartments and listing them on Airbnb as a side hustle while I was a banker and she worked in fashion at Kate Spade. After doing that for a year and a half, I quit my job to go all in.
When I first quit, some people at work looked at me like I had three heads when I told them why I was leaving.
Now, a decade later, we have a portfolio with eight homes, a growing mentorship business, and two children whom I get to spend more time with than ever.
My path to Wall Street
I learned my work ethic from my mom. Even though the bus fare was a quarter or two, my mom would get up early and walk to work so they could save up money to buy a house.
I went to UC San Diego on Pell Grants and worked odd jobs. My first job after school was as an insurance adjuster with State Fund, the state-sponsored workers’ comp carrier, but I had aspirations to work in the financial markets. At 24, I took a temp job off Craigslist at a proxy research firm, Glass Lewis, that had recently been founded in San Francisco.
My parents asked what I was doing, since it was a pay cut, but I explained that this was my path to investment banking. Eventually, with the help of some mentors, it paid off.
I started banking full-time in 2009 after graduating from Cornell’s Business School. It was the most money I’d ever made. I was working on multi-billion-dollar deals that I’d see in The Wall Street Journal, flying business class, and staying in nice hotels. Exactly what you think investment banking is.
I learned a lot, but I realized that I wanted more. I saw how disruptive the career could be for my colleagues’ families: kids in boarding school and a spouse in a different state.
A colleague of mine was turning comments on a board deck while his first child was being delivered, and was back at the office the next day for the deal. And I remember thinking — that’s the job. That’s what it asks of you if you want to win in this business.
You only get your kid’s first moments once, and the deal will always be there asking you to miss them. I didn’t want to be the guy who made that trade.
Walking away
By my mid-30s, I’d saved enough money that I was ready to get married and start a family. But well before our wedding, my wife, Elizabeth, and I were trying different side hustles to build a business that could eventually give us more control over our time.
She married a banker, but she was willing to take a step back to take two steps forward.
You didn’t need to be an investment banker to understand that cashflowing $10,000 a month on an apartment with a $2,500 monthly lease and $1,500 of monthly expenses was pretty good.
We kept growing that business, and eventually, after a year and a half of sacrificing nights and weekends to build our portfolio, I was ready to quit my job in 2018.
When I did, one managing director could not process it when I told him —he froze like a computer.
The biggest bump in the road was COVID. After everything shut down, we lost all of our bookings but still had to pay rent on our apartments. For a moment, it felt like the business we had been building for years was over and I might have to return to banking.
But we rebuilt, and later that year, we bought our first property in the Smoky Mountains of Tennessee to take advantage of the short-term rental tax benefits. We now have eight.
It took three years to get back on track financially from where we were when I quit banking.
After getting so many questions about how I got out of banking while living in New York with two kids, we started a short-term rental mentorship business in 2023 called STR like the Best, along with a podcast.
After the One Big Beautiful Bill made bonus depreciation permanent, we launched a homebuying program buoyed by the tax benefit. We’ve since helped over 100 of our clients purchase an investment property
Why it was worth it
This summer, I’m spending seven weeks in Taiwan bringing my two children to summer camp and visiting my wife’s parents while still running our business. I never could have done this as an investment banker. I would have dropped them off, given them a hug, and then not seen them for two months.
My parents are older now, and I can spend more time in San Francisco to help take care of them. I see it as a small way to pay back what they did for me.
When you’re a banker, you’re optimized for the firm. They control your calendar. Now I can optimize for my family. The business is a means to fund our own personal freedom.
In investment banking, you’re never off the clock. It’s the same with entrepreneurship. But now I own all the upside and downside of my decision here. I didn’t want someone else to decide the outcome for me.
I miss the intellectual firepower of colleagues and the clients I worked with. I learned a ton from banking. It made me a much better businessman by working alongside some of the smartest CEOs and operators in these large businesses.
There’s something Keanu Reeves said on Colbert that resonated with me more than any other quote. Colbert asked him what happens when you die, and Reeves said, “I know that the ones who love us will miss us.”
That really stuck with me. Your money is not going to miss you. Your kids, your wife, your family will.
As for my parents, my mom is no longer able to say her son works at a big bank. She instead says that her son went to Cornell.
But now that they’ve seen how much time we spend with our family, they’ve come around to it.
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