From Start-Up to Grown-Up summary

Another founder, Jake, was struggling to get his investors to put more money into his start-up. The investors were skeptical about revenue growth and cost structure. They wanted to see a new backer step in to take on some of the risk.

The uncertainty sent Jake into a tailspin. What if he couldn’t raise the round elsewhere? What if this meant the end of the company? He became convinced that people would discover that he was unable to get more funding from his investors and conclude he was a bad leader. 

Have you ever watched Rafael Nadal play tennis? Before a match, he’s known to drink his energy gel, water, and recovery drink in precisely the same order every time. This routine is a ritual he uses to center himself. 

Little rituals like this are common in sport – like in baseball, when the batsman steps out to swing the bat, and maybe looks up at the sky before he’s ready to get back into position and make a hit.

Jocelyn was the founder of a health-care start-up, though she wasn’t medically trained herself. To fill the gap in her knowledge, she hired as many doctors as she could. 

During her coaching sessions with the author, Jocelyn shared her frustration: the doctors were experts, but they weren't cooperating, they weren't meeting deadlines, and their teams were confused. Although Jocelyn had hired the doctors based on their medical expertise, she hadn’t considered the importance of leadership and work styles.

Lindsey was building a skincare empire. One day, when the author stopped by the office, she noticed a packaging designer named Wilson was visibly upset at his desk.

When asked what was wrong, Wilson said that he worried Lindsey didn’t like one of his new designs. She hadn’t said so directly, but there was a rumor that she’d been critical of it. 

An early-stage start-up can feel like a wild ride. You’re making it up as you go along but everything feels fresh and exciting. If things go well and the company gets a first round of funding, you know your chances of doing it again are possible.

You keep going and going until – fast-forward – you’ve become a company of 50 people. Suddenly, you have way too many people to manage personally. 

When you first start a business, it’s tricky to predict how much you’ll sell or how many new leads you’ll land. In the early stages, selling more in one quarter is considered a mark of success. But what if you could have sold even more than you actually did?

This is where metrics come in handy. 

Josie and Raj met in college, where they discovered they’d both had the same idea for an online marketplace. Although they didn’t know each other very well, they decided to start a business together. 

The pair quickly raised $10 million and, as their customer base grew, got office space and hired 18 people. All was fantastic – except for one problem: Josie was having issues with her cofounder.