Take Lessons’ CEO talks about the realities of starting a business and walking the fine line between self-promotion and humility.

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June 27, 2020 2 min read

Opinions expressed by Entrepreneur contributors are their own.

Steven Cox is the founder and CEO of Take Lessons, 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 Take Lessons. Cox also discusses the realities of and how they differ from the myths.

Cox offers lessons of his own, advising to believe in themselves, but not their hype — to not take their 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 Take Lessons after helping his rock band’s drummer find work as a 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 , with the expectations shifting while the game stays the same over time. Cox explains that, at 12 years into running Take Lessons, 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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