We set out to diversify our income. We ended up buying a business, and betting our savings on scaling it.
ICYMI, we’ve been talking about a topic most couples avoid: money. More specifically, how to have conversations that actually move you forward financially.
I invited my husband, Jason, onto the podcast to share how we schedule “Money Dates” to align on our goals and build a financial plan together. In the first part of this series, I walked through the agenda for our very first one so you could easily plan your own Money Date too: understanding what we earned, what we spent, and how we wanted to grow.
But our second Money Date is when things got real.
We sat down to create a plan for diversifying our income, because we knew that long-term wealth and flexibility would come from building beyond our paychecks.
We landed on a clear path forward: invest in something “passive.” Something that could earn on autopilot while we both continued working full-time. Real estate felt like the safest next step for us, so we started there. Jason ran numbers, researched markets, studied options on Roofstock late into the night.
Eventually, we bought a vacation rental in Tahoe.
It was meant to be our introduction to “passive” income. Instead, it became our crash course in what ownership of a rental actually takes… maintenance calls, property management issues, broken decks, snow damage, and a long list of lessons about how “hands-off” short-term rental real estate investing rarely is.
That experience changed how we thought about investing. Because yes, we really wanted passivity, but we also wanted purpose.
So when the opportunity came up to buy an existing Pilates studio, we looked at it through a different lens. Could this be the next evolution of our strategy? Could something active, something aligned with what we actually love, become both an investment and a lifestyle?
The numbers worked. The timing felt right. We said yes.
Shortly after, we sold the Tahoe property and reinvested fully. Our plan was modest: grow to three studios, eventually replace Jason’s income, and create a more flexible life. But within six months, we started to see potential we couldn’t ignore.
The business was way outperforming expectations thanks to our strategy applying best practices from the startup world into our organization. Our complementary skill sets in finance and marketing gave us an edge. Multiple macro-trends were colliding with all arrows pointing to success.
So we made the biggest decision of our financial lives: we decided to go all-in into scaling this business, including Jason leaving his W2 job last February.
We went from “how do we earn a little extra?” to “how do we build something much bigger?”
And while we walk through the full story in this Toolkit episode, this conversation is really about you. If you and your partner are trying to figure out your next step, whether that’s real estate, side gigs, or entrepreneurship, this episode gives you the questions to ask and the strategy to get aligned.
Here are 3 lessons we share in the episode:
“Passive” income still takes energy. The moment you stop paying attention to it, it stops performing.
Run the numbers, but listen to your gut. Data will tell you what’s possible; intuition will tell you what’s right.
Double down on what gives you energy. The right investment feels like fuel, not a chore.
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TLDR, inside this episode:
In this episode, we break down how to navigate your second Money Date: how to explore different income streams, assess your risk tolerance, define your roles, and align on a strategy that fits your actual life, not just the one on paper.
💼 Find your money mix - The pros, cons, and effort behind different income streams.
🏠 Passive income myths - What Airbnb ownership really looks like.
🏋️♀️ Passion as profit - How buying a Pilates studio changed our view on investing.
🧰 Your Second Money Date - An agenda for your next meeting to evaluate diversification paths and take action together.
💬 Drop a comment and tell me: what passion would you love to turn into profit?
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Thanks for listening,
Barbara
