Don't Believe Your Own Hype

TakeLessons' CEO talks about the realities of starting a business and walking the fine line between self-promotion and humility.

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Steven Cox is the founder and CEO of TakeLessons, a venture-backed startup that connects students with instructors of the arts, academics and foreign languages, locally and online.

#ThePlaybook host David Meltzer talks with Cox about the origins of TakeLessons. Cox also discusses the realities of entrepreneurship and how they differ from the myths.

Cox offers lessons of his own, advising entrepreneurs to believe in themselves, but not their hype — to not take their self-promotion too seriously and to be able to see that they can be wrong at times. To do this, Cox suggests, entrepreneurs should wear both the “founder” and “investor” hats as they grow their business.

Cox talks about how he started TakeLessons after helping his rock band’s drummer find work as a music instructor and how staying nimble, listening to customers and adapting allowed his company to find product-market fit before running out of money.

Cox and Meltzer also chat about how running a business compares to baseball, with the expectations shifting while the game stays the same over time. Cox explains that, at 12 years into running TakeLessons, he’s now focused on making sure investors are happy and planning for the next five years.

Related: How This Entrepreneur Taught Himself to Code by the Light of a Kerosene Lamp

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