HerMoney Podcast Episode 328: Your Big Money Bet 

Over the last few months and weeks, there have been more ups and downs in the stock market than we care to count, and experts say that market volatility isn’t going anywhere anytime soon. It’s easy to see why investors are nervous. How do you take risks in an era that already seems so very risky? 

In other words: How do you find safety while also stretching yourself, and opening yourself up to possibility? We know that big risks can equal big rewards. And most, if not all of us, have imagined what it might be like to start our own thing, and have wondered if we have what it takes to lead an organization, develop a new product or generally just test our limits as women. 

We spend a lot of time at HerMoney talking about what it means to find success — in our financial lives, in our careers, even with our families and friendships. And the truth is that there’s an incredibly wide spectrum for exactly how women can take the kinds of risks and make the big decisions that can benefit our lives. And that spectrum is growing wider every day as more career paths open up  and more women find success in traditionally male-dominated fields. 

On this week’s episode, we’re learning about those calculated risks and how to make big money decisions from one of the absolute best — Jenny Just, one of the few self-made female billionaires in the United States. From her early career days on the trading floor in Chicago to now running a fintech empire, she has started and/or turned around more than fifteen companies. She co-founded her company PEAK6 in 1997 with $1.5M in seed capital as a proprietary options trading firm and since then has grown it into a multibillion-dollar financial services and technology giant. In addition to Jenny’s ability to transform, Jenny looks for underfunded and under-appreciated sectors into high-growth businesses, and is also adept at finding opportunities for women to succeed at every table — from the classroom to the board room —  even to the poker table. In 2020, Jenny also launched Poker Power, a company that teaches poker to all who identify as female, and by extension, teaches women strategic thinking, capital allocation, and decision-making skills.

As you might expect, Jean and Jenny cover a lot of ground in this show. They discuss risk and gaining the confidence to take risk — in life, in work and in the markets. (They discuss Poker Power, what women are being taught, and why there’s such electricity in the room when women take their seats at the table.) You don’t want to miss what Jenny says about how to perfect your “poker face,” and how it helps with all manner of negotiations. We also break down what it is that truly scares us about risk — why does the “status quo” sometimes feel better, and how can we move past that? 

They also discuss decision making and deal-making, as they relate to your career and investing. We dive into what Jenny is seeing in the markets today, and she offers up her best advice for investors, particularly for those of us who may be more risk averse. In Mailbag, we advise a woman on where to put additional money for retirement, and we hear from a listener wondering where she should put money for her niece and nephew’s futures. And in Thrive, how to host the cheapest summer BBQ (and still have a blast).