To tuck it in, or not to tuck it in?—That is the question

By KINJAL SHAH Communications Writer

Eight million shirts. Five hundred employees. Eighty six stores. Today, UNTUCKit cofounder Aaron Sanandres, class of 1992, and his business partner, Chris Riccobono, are celebrating their well-deserved success!

Looking Back…

Sanandres was eight years into a career at PricewaterhouseCoopers when he decided to pursue an executive MBA program at Columbia Business School. Little did he know that life was about to pose him one of the most challenging questions: To tuck it in, or not to tuck it in? When Riccobono approached him, planting the seed for making untucked shirts, UNTUCKit was born. It started with US$150,000 capital for a few thousand shirts, a small PR firm, and a company website.

Today, the company boasts 85 stores across Canada, the UK, and the US, and is celebrating 12 years in the business. Resilience has been the name of the game so far and UNTUCKit continues to surpass its pre-pandemic performance. It is one of the fastest-growing men’s retail brands in the US.

After graduating from Singapore American School, Sanandres attended Hamilton College in upstate New York, a liberal arts school he credits with honing his communication skills—which he believes is the single-most important skill set to learn in any newly minted career. He then took a postgraduate year in Beijing, China to focus on learning Mandarin—a result of the impact that SAS teacher Mr. Goh had on Sanandres. Spending a year immersed in Chinese language and culture allowed him to attain (temporary) fluency in Mandarin. He graduated cum laude from Hamilton College with a double major in government and Asian studies.

According to Sanandres, SAS was pretty special in many ways. “Although I might not have appreciated it at the time, going to school with such a diverse group of friends—Australian, Danish, Indian, Singaporean, and more—gave me a unique ability to bring out the best of cultural differences” he says. Among many favorite memories, it is the Interim Semester trips that he thought were particularly special. “From my first trip on a Johor safari to my final trip scuba diving in the Maldives, I couldn't have asked for more!”

Sanandres fondly remembers his educators at SAS and the impact they had on his life! They include Mr. Imperi, who had a phenomenal ability to engage his students in classroom discourse; Ms. Donahue, who always challenged Sanandres to do his best; Ms. Banks, who was one of the kindest teachers he remembers; and Mr. Goh, who inspired him to study Mandarin throughout college and then spend a year in Beijing in intensive language study.

To budding entrepreneurs, Sanandres has simple advice:

Do it. There is no fixed path to becoming an entrepreneur. Some quit their jobs and start something on their own. Some, like me, build their business as a side gig until they have the stability and cashflow needed to quit their day job and go full time. As Nike so perfectly articulates: Just do it. I’m almost certain you won’t regret it.

Sanandres’ Tips to Entrepreneurial Success

When it comes to entrepreneurship, there are literally hundreds of critical lessons I’ve learned along the way. Some I’ve had to learn twice! If I were to limit them into the top five they would likely be :

1. Make forward progress. So many business ideas die before they’ve even had a chance to breathe. Ideas don’t build businesses. So take action. Every day. Keep moving the ball forward. Progress begets progress.

2. Invest in market research. Market research allows you to stay ahead of your competition by keeping you updated on the latest trends and industry developments. You will gain valuable insights into your customer base.

3. Know your metrics. So much about being an entrepreneur is making decisions with incomplete information. So make sure you are using all the data you have to your advantage. With advances in AI, you don’t need to be a stats beast to win on analytics.

4. You don’t have to go big to go home. Don’t set lofty goals. Success isn't just about achieving huge milestones or reaching the top of the ladder. Celebrating small wins can give you the motivation and confidence to continue on your path toward success.

5. Have fun. It can be a daunting, often lonely path…so take the time to celebrate the little wins along the way.

Singapore American School