Third Shift Entrepreneur summary

When you use a rideshare service or take a taxi, do you like to chat with the driver? Or are you more the type to pop in your earbuds and start answering emails? 

Our wannabe entrepreneur Matt is not usually a talker in these situations. But one morning, on his way to the airport, he decides to engage. The conversation gets interesting when driver Kenneth quickly moves past small talk to ask about Matt’s work – and then specific questions about how his company plans its leadership retreats. 

Matt doesn’t think much of it until he returns home and attends another business meeting with a new client the next day. Who’s that guy on the strategy team? thinks Matt. He looks so familiar. And then it hits him – Kenneth! 

Turns out, Kenneth has a day job as a consultant, just like Matt. When the two talk privately after the meeting, Matt learns that Kenneth’s rideshare work has a greater purpose: he’s using it to gather information on how to start a corporate retreat venue business. 

On hearing this, Matt shares that he also wants to launch a business – but he doesn’t yet know exactly what. Kenneth invites him to attend a meeting with his entrepreneur group, the Third Shift Entrepreneurs. 

The next morning, Matt meets a handful of people starting businesses, along with their mentor – an established entrepreneur named Regis. It soon becomes clear that the people and their businesses are all wildly different, but that they share a common thread: each one is guided by a mission to serve others with something that’s unique and deeply personal to the founder. 

This, Connor says, is the observation of obsession.

Matt is inspired by their stories, but he’s still a little fuzzy on his own obsession. So he gets two bits of homework: 

First, make a list of things you can’t get off your mind. These could be things you love, your talents, or even problems that frequently annoy you. Ask a friend or family member for input too. Keep your list handy.

Next, start mixing up your routine. This will help open your mind to new things. 

That afternoon, Matt chooses to go for a jog after work instead of immediately settling in for the evening. He finds the exercise and different view of his neighborhood invigorating, and decides to meet up with group member Yisel to learn about her coffee-roasting company – where he’ll have another big observation.