Kristi Ross stops by The Business Brew to discuss her career, leading companies through M&A, and two notable exits exceeding $1.5Bn (the most recent of which was valued at $1Bn. Kristi is the co-CEO of tastytrade, which launched in 2011. She also co-founded dough, a visual front-end trading technology platform that launched in 2014 and ultimately merged with and rebranded as tastytrade when the team launched their own online brokerage firm, tastyworks, in 2017.
Kristi is an award-winning entrepreneur who believes in empowering the do-it-yourself investor to engage more with their finances. She also uses her time to interview innovative entrepreneurs on her show, Bootstrapping in America. She also walks through the ins and outs of taxes for traders in Kristi’s Tax Bursts.
Kristi started her career in public accounting, specializing in financial services industry clientele including individual traders, proprietary firms, market makers, and advisory firms. After her run as a public accountant, Kristi acted as CFO of Automated Trading Desk Specialists, a stock specialist on the Chicago Stock Exchange. She then partnered up with Tom Sosnoff to serve as CFO of thinkorswim Group where she led numerous mergers, acquisitions and integration. thinkorswim sold to TD-Ameritrade for $750M in 2009.
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Detailed Show Notes
- 3:30 – Kristi’s background
- 5:05 – How Kristi growing up formed her views on entrepreneurship
- 7:00 – Applying for a CFO job at 24/25 years old
- 10:00 – getting into the trading industry
- 13:00 – A primacy of customer service and education
- 17:10 – Comp as incentives
- 24:00 – starting tastytrade
- 26:00 – trading small and defining risk
- 29:20 – Selling a business today vs 2009
- 33:30 – Team building, a “can do” attitude, and the advantages of remaining private
- 39:30 – Kristi’s involvement in 1871, a Chicago based incubator
- 42:15 – Kristi’s show, Bootstrapping in America
- 43:15 – Why Chicago is the greatest place on Earth
- 47:30 – Payment for Order Flow
- 58:20 – Trading vs Investing
- 58:30 – Kristi’s thoughts on passive investments.
- 1:02:30 – How to instill entrepreneurship in your child according to Kristi
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