‘They destroyed us.’ Pitching to students was more nerve-wracking than being on ‘Dragons’ Den’

“I know that every single person in this room would love if every time they walked out of their house, they were walking under a waterfall of compliments.”

Big, bold and descriptive — that’s how Jeff Alpaugh’s pitched his custom dress shirts in the Den as a handful of models stood before the Dragons, donning his vibrant designs.

Alpaugh, a former military officer, and his business partner (and real life partner) Emilee Boychuk pitched “the world’s most dangerous dress shirts” on Dragons’ Den: Jeff Alpaugh Custom.

He promises his shirts’ loud colours and patterns will get heads turning, especially in a “sea of blue and white” shirts that dominate common retail selections. The eye-catching shirts were just part of the duo’s success in the Den. Alpaugh’s animated, vibrant personality surprised the Dragons — which made them pay extra attention to the pitch. 

But it was more than personality that made their pitch memorable. From the moment Jeff Alpaugh found out he was going to be on the show, he prepared “deliberately and meticulously” for the pitch. And he recommends other pitchers do the same.

Meticulous preparation

“I prepared answers to every possible question I could think of.” He re-watched the entire last season of Dragons’ Den and took notes on the types of questions the Dragons asked .

And then he and his partner Emilee did a dry run, pitching to the University of New Brunswick’s MBA students. “They destroyed us. I was more nervous there than in front of The Dragons,” said Alpaugh.

Divide and conquer

When their day in the Den came, they felt prepared.

“Emilee and I decided on roles and responsibilities [for the pitch]. I would answer A,B,C type of questions and she would answer X,Y,Z questions.”

They also knew which Dragons they wanted to reach: Michele and Michael. They tailored their pitch to appeal to them.Initially, it was Jim who took a particular shine to Alpaugh, seeing in him a reflection of his own journey from veteran (of both military and police force) to entrepreneur.

Describing his time in the service, Jim said, “It put some discipline in me that I never had before.”

Alpaugh agrees. “The army has taught me that I am responsible for everything that happens or fails to happen,” said Alpaugh. “That victory depends on assessing the factors, detailed planning, communicating the plan effectively and relentless hard work in execution. All that simply boils down to discipline.”

In the end, Jim promised Alpaugh “a hell of a deal” — if he ever decides to get out of the clothing business.

“If, for some reason, it does not work out, I would not be too proud to approach Jim,” said Alpaugh. For now, however, he is sticking to clothing. “I plan on making JAC a global brand within five years.”

Partners in business and love

Alpaugh’s business partner is also the love of his life, Emilee. While some entrepreneurs would balk at working with their real-life partners, Alpaugh only sees a benefit to having her close.

“Business is incredibly personal. I share every victory and defeat with Emilee,” said Alpaugh. “We are always in tune with each other and can understand one another.”

And with shared passion comes the thrill of the shared challenge.

“It feels like being on The Amazing Race together 24/7. We face obstacles and problem solve together constantly and it strengthens out relationship,” said Alpaugh.

Building a brand with personality

If, like Alpaugh, you’re considering using your own personality to market your brand, he warns, “it’s not for everyone.” But starting a business in a new city with no money, he knew that he could be the marketable figurehead his company needed. “It's all about assessing the factors and using the tools available,“ said Alpaugh.

And what were fans of Jeff Alpaugh Custom thinking during the pitch? Alpaugh shared a video of his viewing party which features friends, supporters and even the mayor of Fredericton, N.B..