Raising Thriving Companies— And Daughters: Advice From Billion-Dollar Co-Founder Kristi Ross
Recently, I had the opportunity to interview Kristi Ross, Co-CEO and co-founder of tastytrade, which she helped navigate to a $1 billion acquisition by IG Group in June, 2021. Prior, she joined thinkorswim as CFO in its early days. Ross helped the founders create and scale the company to its sale to Ameritrade in 2009 for over $700 million.
We explored leadership within (rapidly!) scaling enterprises scaling and how her life shapes her leadership.
I was also interested in how she and her (equally Type A) husband have simultaneously raised three successful daughters. As a father of two daughters, Jolie and Sage, I’ve grown to appreciate not only the challenges of leadership within organizations but also within families. (Or at least the pretense of family leadership!)
Find our full video interview here.
The Power Of Great Dyads
Apple had Steve Jobs and Steve Wozniak. Berkshire Hathaway has Warren Buffett and Charlie Munger.
You can think that way of Kristi Ross and Tom Sosnoff, the visionary behind thinkorswim and tastytrade. Complementary co-founders are a blessing to any company. Sosnoff, Ross and their investors have been doubly blessed.
That doesn’t, though, mean they’ve always been right. The original concept behind tastytrade was to “make finance fun” while also empowering the self-directed investor. Ross recalls, “we started a little too heavy on the fun.” After about six months of going big with comedians and improv, they found their customers wanted a lot more finance and just a “flare of fun.”
The company had a compelling vision, but still had to discover the right formula. She advises to “be accessible” to customers and ensure its a two-way conversation. “If we hadn’t listened to our customers, we would have failed.”
Ross also confesses, “I really hope those original archives are buried deep somewhere and no one ever sees them.” Understandable sentiment— though those early missteps enabled their eventual billion-dollar success. (I’d love to see those videos!)
Leadership Begins Early— In Life And Breakfast
Early in our interview, Ross goes to the source— her parents. While her mother died while Ross was still a teenager, she reflects often on her influence. Her mother advised and modelled, “just be nice,” even when you need to disagree or stand up for yourself. We could all benefit from such vigilant civility— if I may brand Ross’s mother’s wisdom— as we face a society-wide decline in trust.
Her father featured large. “I was lucky enough to witness a man with endless optimism.” While she shared that his ventures never quite took off, he never relented. “I learned it was OK to fail and it was ok to have big dreams— but you should do something about it.”
While in elementary school, Ross would often rise “very early” to spend time with him before work. Over his morning coffee, Ross and her father would muse plans for new businesses. “I recall one was for a hotdog stand…. You’d sit inside a big bun with an umbrella over it. Creative conversations is how I’d frame it.”
As she grew older they’d debate topics like race, religion, “touchy subjects. He welcomed my opinion.” Sometimes disagreeing but never judging, these experiences were foundational for her leadership style. “Listening is key to developing the people around you. Allowing them to talk through to solve their own problems.”
Confidence Does Not Equal Competence
When I asked Ross to share a career epiphany, she summoned an experience during her first role leading a major M&A deal. She inquired with a much older colleague about a critical point. He opined with such confidence, she at first assumed he must be right. Dubious, she spent hours researching— discovering he had been critically wrong.
She cautions, “Confidence does not equal competence. Confidence equals the perception of competence. I learned not to assume someone knows more than me.”
Tackling Life Decisions— Still Like A CFO
As any great CFO, Ross structures the tough decisions— even about life.
“Any time I’ve had to go through a difficult decision in my life, I pull out one of those trusty oversized yellow legal pads.” She lists pros and cons, assigning a numeric rating to each point.
When she started to have kids, her legal pad protocol led to a major career change. She loved her job but hated the extensive travel. She respectfully quit, “to create that special time with my family.” Still all-in on her demanding career, she created a family tradition. Connecting with her family every morning at breakfast— a tribute to those breakfasts with her father.
Ross recommends, “forcing mindfulness into difficult life decisions.” Create symbolic opportunities for impactful moments. “As a parent and as a leader, we all want that.”
Calvin and Hobbes: Parenting Experts
There are life decisions— and then there’s life.
Soon after marriage, Ross and her husband discussed how to prepare to have children. She shared with him a Calvin and Hobbes cartoon that gave her pause. Calvin interrogates his parents, “What assurance do I have that you’re not screwing me up?”
She and her new hubby reasoned, we should try plants and see how that goes, then a pet. “We never got a pet…. We just jumped in with both feet to have kids.”
While you can never really prepare for children, the journey becomes its own preparation. “As they grow older, you realize you really do have an impact on who they are and what they believe, and to some degree who they become. That’s a lot of pressure.”
Ross draws a leadership parallel. “I still have that comic. It’s a good reminder to me of the impact we have on the people around us. [As leaders] we should be mindful of what we do, what we say.”
Advice For Our Daughters
I couldn’t resist soliciting Ross’s advice for my daughters. “I have a hundred pieces of advice.” Literally. Ross penned a private book for her daughters as they departed for college. It pronounces 100 life lessons.
In addition to her many mottos such as “Just Do It” —featured on her wall during our interview— she advised, “It’s about making decisions for you, not necessarily for the people around you. You are here to find the right path for you.” We could all value that book.
I’ve since shared Ross’s wisdom with my daughters. At 12 and 10 years old, I imagine they’ll grow into Ross’s advice. (We all must.) My wife Ada and I do our best to support them. Meanwhile, we’re optimistic— and thankful for Ross’s example.