Advice Line with Chris Riccobono of UNTUCKit

Chris Riccobono, co-founder of UNTUCKit, returned to the Advice Line to help three founders navigate growth, marketing, and brand strategy. He brought a blunt, battle-tested perspective shaped by building a 73-store apparel brand from scratch, surviving COVID debt, and absorbing a $9 million tariff hit. His advice was less about inspiration and more about hard choices: who you target, how you spend cash, and whether you are truly committed to building something big.

The Volleyball Shorts Founder: Find Your Tribe Before You Try to Own Everything

Adrian Alvarez, a college sophomore, built Era Shorts to $400,000 in annual revenue by selling affordable hybrid shorts. His question was how to turn his brand, which had found traction with volleyball players, into a mainstream competitor like Nike or Lululemon.

Riccobono pushed back on the premise. He argued that Adrian’s real advantage was that he had already found a tribe with little competition. “Maybe you do want to focus on volleyball right now,” Riccobono said. “You start running ads to volleyball players… you’re the only game in town.” He warned against the temptation to use a generic message like “shorts for everyone” when the brand’s actual strength was specificity. Guy Raz reinforced this, noting that Lululemon and Vuori built on specific communities before scaling.