Brian Spaly loves top quality pants. You can tell because he calls them “trousers” the way Francis Ford Coppola talks about his “films” rather than his “movies.” And when a CEO who loves what he does takes the time to talk honestly about his experience as an entrepreneur, it’s time to listen up.

Last week, Brian sat down at Catapult Chicago to discuss his journey from a business school student selling handmade trousers out of the trunk of a car to the chief executive of men’s style startup Trunk Club. A service for men who want to look great without investing the time it takes to shop for top drawer clothes, Trunk Club is poised to become a leader in both the men’s fashion world and the Chicago tech scene.

 What follows is a condensed version of his Catapult Conversation.

  • It never stops being important to ask yourself, “What do I want to get out of my life, my career, the next five years, and this summer?” What you ultimately want should inform what you do today.
  • Effective and empathetic communication is a cornerstone of building a business—the most talked about class at  Stanford business school was affectionately called “touchie feelie.”
  • Failing does not make you a failure. My first venture in the fashion industry worked but it didn’t work out.
  • Trunk Club is growing and successful, but there have been a few hiccups. This summer’s numbers have been sluggish, at least partly because “it’s been hot as balls.”
  • That’s not to say that the weather or the economy are ever excuses for poor performance. High unemployment means the market is labor rich.
  • The hardest thing about being CEO is figuring out how to be a real servant leader.
  • Criticisms should be delivered in a way that they can’t be misinterpreted as personal attacks.
  • Failing fast means failing cheaply.
  • Chicago is a great place to build a business. “It has a shit-ton of Fortune 500 companies in it, and you can fly anywhere in the country for about $300.”
  • In the end, jobs one, two, and three for a business leader are to win.
  • Investing safely is no fun. Besides, “if the world gets to a place where you need to invest in guns and gold, then I’m probably just going to jump out my apartment window anyway.” 

Picture of Brian via www.brandingtheman.com