Ep 289 – From Tragedy to 65 Units: How Cara and Mark Truckey Built a Life and Business on Their Own Terms

In 2016, Cara and Mark Truckey lost their 14-month-old son. He never woke up at daycare.

Most couples don’t survive a loss like that. Instead, it became the moment that changed everything.

In this episode, E and Chris sit down with Cara and Mark Truckey — two STR Secrets boardroom alumni who have built a real estate portfolio of 65+ units across Wisconsin and Florida while raising three kids and running multiple businesses.

This is one of the most honest and human conversations we have had on this show.

In this episode Cara and Mark cover:

– How losing their son reshaped their entire perspective on time, work, and money
– How Cara quit her hospital job in 2020 and Mark quit his plumbing W-2 in 2021
– How they went from a few house flips to 65+ rental units across two states
– Their first STR — a lake property in Wisconsin they bought by accident
– Why Mark struggled with delegation for years — and the 80/20 rule that broke the pattern
– How to find the right people for the right seats — and why belief in the vision matters more than skills
– How Cara transitioned into Savvy Realty as a top agent in the Tampa Clearwater market
– What actually keeps a husband and wife business partnership aligned
– The daily habit that is their real superpower — and has nothing to do with business
– How to change your identity before the results show up
– Mark’s upcoming $130 million capital campaign for a K-12 school in Wisconsin
– Cara’s goal: 40 STRs under management in Florida by end of 2027
– Their #1 secrets to success: courage and fighting past limiting beliefs