Take Risks And Win Big With Sukhinder Singh Cassidy (2026)

Saving money on take risks win big does not have to be complicated. We rounded up the essentials so you can spend less and skip the guesswork.

Key Takeaways

• Sukhinder Singh Cassidy has sold three startups, most recently the Boardlist, but she feels like she’s just getting started.
• Unfortunately, even in 2024, female startup founders are few and far between.
• A recent survey from Startup Genome found that only 15% of startup founders are female, and when asked, just 22% of people can name a single...

Sukhinder Singh Cassidy has sold three startups, most recently the Boardlist, but she feels like she’s just getting started.

Unfortunately, even in 2024, female startup founders are few and far between. A recent survey from Startup Genome found that only 15% of startup founders are female, and when asked, just 22% of people can name a single famous female in tech, despite brands like YouTube, Oracle, and Canva being run by women. We hear about female serial entrepreneurs even less…

But Sukhinder Singh Cassidy is one of those women. She’s sold not one but THREE startups , but her journey to get there has been paved with numerous successes and failures, both of which she’s extremely proud. “People sometimes give me a lot of credit for being confident,” Cassidy says. “I’m confident because I have a resilience to failure. I know that I am not unstoppable, and that I am fallible. If something doesn’t work out the way I imagined, I know it will work out a different way.”

She previously founded a video shopping platform, a financial data platform, and her most recent sale was Boardlist, a board candidate discovery platform that lets you board-ready executives find their first seats, and lets you companies find diverse board talent. 

Cassidy not only knows when to sell a company, but she also recognizes when it’s time to leave. She thinks it’s imperative to recognize when you’ve maxed out in a role, and is an advocate for always taking small risks and seeking out new challenges. “Not moving is the riskiest thing of all because while you are staying still, choice-making is going on around you. So then, you are not responsive to the environment you’re in,” Cassidy says. 

Listen to to learn more about Cassidy’s philosophy in her role as CEO at Xero, her philosophy on hiring people who have experienced failure, and why she believes it’s imperative to take risks in your career , large or small. 

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Final Thoughts

The bottom line: a little research on take risks win big goes a long way. Compare your options, watch for seasonal offers, and never pay full price when a better deal is one click away.

Originally published at savingswitch.com.