Kristi Ross – Entrepreneur Extraordinaire

Hosted by
Bill Brewster

Bill Brewster is a private investor. He cohosts the podcast Value: After Hours with Tobias Carlisle and Jake Taylor. Tobias, Jake and Bill met at a Berkshire Hathaway meeting and formed a lasting friendship. And, as it turns out, people really like the podcast.

While Bill tries to replicate Warren Buffett and Charlie Munger’s thought processes, he is heavily influenced by Bill Miller III, Stan Druckenmiller, and others. This podcast is his attempt to dig deeper into other investing/business philosophies and share the knowledge with the world.

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.

We hope you enjoy the discussion. Detailed show notes below the Stream by Mosiac sponsor copy and thank yous.

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Album art photo taken by Mike Ando. Please see https://www.mikeando.com/.

Thank you to @mathewpassy for the show production.


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

Disclaimer: Bill manages a portfolio under the name of Sullimar Capital Group. This podcast is for informational and educational purposes only. Nothing in this podcast or on SullimarCapital.Group is investment advice. All information in this is opinion based, potentially biased, and requires verification.

Bill and his guests make no representation, warranty or undertaking, express or implied, as to the accuracy, reliability, completeness or reasonableness of the information contained in these podcasts. Any assumptions, opinions and estimates expressed constitute the participant’s judgment as of the date thereof and are subject to change without notice. Any projections contained in the information are based on a number of assumptions as to market conditions and there can be no guarantee that any projected outcomes will be achieved. This podcast does not accept any liability for any direct, consequential or other loss arising from reliance on the contents of this presentation.

This podcast series DOES NOT CONSTITUTE AN OFFER TO SELL OR THE SOLICIATION OF AN OFFER TO BUY ANY SECURITIES MENTIONED OR DISCUSSED. Seek the your financial, tax, legal, accounting, or other advisor’s advice before making any investment decisions. We are not your fiduciary or advisor.

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