Building a Business Around Freedom, Family, and Flexibility: Josh Wollaston on Becoming an Entrepreneur

On C-Suite Chronicles, hosts Jeremy and Wendy talk with entrepreneurs and executives about what’s going through their heads at key points in their careers. In this episode they sat down with Josh Wollaston, co-founder of SPG Capital.

Seven years of doing both

Josh grew up around entrepreneurship, since his father and uncle ran a large family flooring business. Even so, the path he was pushed toward was the traditional one: get good grades and get a good job. After college he joined a major bank and moved up quickly. The senior people above him, though, had almost no work-life balance and took work calls even on vacation.

While still in college, Josh and his partner Alex had read Rich Dad Poor Dad and settled on real estate as the way out. They bought their first rental in 2016. At first they saved up a 20% down payment for each property. Growth took off once they switched to buying distressed homes with short-term private money, renovating them and refinancing. After that the portfolio roughly doubled each year, reaching about 50 units by 2022. That year Josh learned he was expecting twins and decided to go full-time.

When the market changes the plan

Josh expected to buy about 20 more properties in his first year out of corporate life. Instead, rising rates cut SPG’s deal flow to almost nothing within three months. The private investors who had funded SPG’s projects still wanted their money working, though. So SPG started lending that capital to other experienced local investors and earning the spread between what borrowers paid and what investors received.

Josh says that was the moment he actually became an entrepreneur. His approach was to look at the resources and advantages he already had and ask how they could add value for other people. He also notes he would never have spotted the opportunity if he hadn’t been full-time and talking with other investors every day.

Hiring to get time back

For a while the lending business was just Josh and Alex, and Josh says he had nearly “worked myself into another job.” Their first hire was a controller, who now handles wires, closing documents and cash management. That lets Josh spend his time on what he does best, which is building relationships and finding investors.

A relationship business

Josh describes himself as a natural introvert who had to become more outgoing, and he says a real desire to help people keeps him going. Many of SPG’s investors are friends and family nearing retirement who want monthly income to replace a paycheck. One investor was the woman who sold Josh his house. She had been waiting to find someone trustworthy to invest with in real estate.

Protecting family time

Josh’s parents made it to every one of his games growing up, and that is the standard he holds himself to. He schedules meetings between about 8:30 and 3:00, picks his kids up from school, and puts his phone on do-not-disturb in the early evening. He also gets up at 5 a.m. so he has an hour to himself before the house wakes up.

His outlook right now: stay conservative

Josh’s closing advice is to be cautious, keep reserves on hand and be ready for opportunities when the market shifts. He credits his accounting background with making him the more cautious of the two partners and says Alex pushes them forward. He believes that balance leads them to better decisions.

Key takeaways

• A change in the market can point to a better business model.
• Hiring to cover day-to-day operations frees the founder to focus on growth.
• In a business built on trust, relationships are the core asset.
• Protecting family time takes deliberate scheduling.
• Keep reserves so you’re ready when opportunity shows up.

Looking for steady, real-estate-backed income? Book a call with Josh