Episode 17: Follow up conversation with fashion entrepreneur Jeff Alpaugh of Jeff Alpaugh Custom, maker of the World’s Most Dangerous Dress Shirts. Jeff is the first repeat guest on the PDB (first appearance: Episode 4) and provides an interesting update on his entrepreneurial journey since striking a deal on the Dragon’s Den. Jeff opens up about the ups and downs of entrepreneurship, lessons learned in scaling the business and raising capital, and the importance of building a great team around him. All business owners — startup or seasoned — will get a ton of value from Jeff’s candid insights in this interview. And you’ll have a few laughs too!

In this show Jeff and Andy discuss:

  • the ups and downs of entrepreneurship
  • why Jeff feels he’s just getting to Day 1 after 3.5 years in business
  • Dangerous Socks…you not only can wear them with suits and jeans…you can run marathons in them…seriously!
  • NBA Finals predictions…see if Jeff and Andy (and Mayor Mike) got it right
  • Jeff’s favourite book on entrepreneurship
  • what Jeff considers the best clothing logo/brand of all time
  • the history and future of retail and the fashion industry
  • Jeff’s plans for expanding the company’s retail footprint
  • which Ontario city will be home to the newest Jeff Alpaugh Custom retail store
  • where the first U.S. store will be
  • Jeff’s favourite PDB episodes so far
  • the importance of a positive mindset, and focusing on the joy of the journey
  • will Jeff be the Billy Madison of business school?
  • Jack Benson Alpaugh…the newest member of the JAC family

Quotable: “I could talk about the future of retail and clothing forever, and it almost frustrates me how much people are like ‘retail is dying’ and they don’t see that we are on the cusp of a big revolutionary curve.” — Jeff Alpaugh

Featured craft beer:  King West American IPA (King West Brewing Company, Fredericton, NB)