When venture capitalist Annie Lamont bets on companies, she thinks a lot about timing. "Too early is wrong," she says, noting that timing is "probably the most important decision other than backing the right people."

By contrast, “early” in politics can be a smart strategy to lay the groundwork for eventual success. For example, Annie Lamont’s husband, Ned, championed ideas like gay marriage long before they were broadly accepted. His bold advocacy of controversial social issues helped him win the job he has today: Governor of Connecticut. 

Annie and Ned Lamont were our guests on our latest episode of Making a Leader on SiriusXM. Although both Lamonts consider themselves progressives in their respective fields—Ned is a reformist governor and Annie is an intrepid investor—they contend that "getting in early" typically pays off better for politicians than for VCs.

When she isn’t performing her various duties as First Lady, Annie is Managing Partner of Oak HC/FT, a Connecticut-based firm that finances early and mid-stage companies in healthcare and fintech. Here’s how she thinks about timing her bets on startups: "Is the market ready for what the entrepreneur wants to sell? So often, particularly in healthcare, there’s the way the world should be versus the way it is."

"How do you know if you’re too early unless you try?" asks the governor, who learned plenty in his rough ride to high political office. Ned Lamont's success in politics came after he stumbled in two high-profile races—first for a seat in the U.S. Senate and later for the governorship in 2010. He won Connecticut's gubernatorial race in 2018.

Before betting his career on politics, Lamont endured the risky ups and downs of business, as an entrepreneur in the cable TV and telecom industries. "Maybe in business, you don’t want to be that much early because you’re pouring money down a rathole before the market is ready," he says. "In politics, sometimes you gotta be willing to take that risk and be a little early. If you get knocked down, you get back up."

"So, that’s why he’s the entrepreneur and I’m the investor," says his relatively risk-averse wife, smiling at the workable balance of their power coupledom.

On Making a Leader, award-winning interviewers (and Co-CEOs of SellersEaston Media) Pattie Sellers and Nina Easton talk with extraordinary leaders about how they find and define success. You can listen to the full interview with Ned and Annie Lamont on Making a Leader on SiriusXM Business Channel 132 at 6:00 pm ET today—Tuesday, January 14. This episode will repeat on Channel 132 at 2:00 am and 6:00 pm ET on January 15, at 2:00 am and 8:00 am ET on January 16, at 4:00 am and 6:00 pm ET on January 17, and 9:00 am and 4:00 pm ET on January 18. To listen on demand on the SiriusXM app, search Making a Leader and tell your friends!