From her beginnings as a college student dating her boyfriend (now co-founder of a cookie empire), Tiffany Chen of Tiff’s Treats has many valuable nuggets from her journey to share, whether or not you have a sweet tooth. 

On this week’s episode of In the Details we dig into Chen’s adjustment from baker to business owner, the connections that were instrumental to her success and how to move past failure and identify your greater purpose. 

From baker to business owner

When Chen was 19, she baked her boyfriend cookies as an apology for standing him up one night. This gesture sparked her boyfriend’s idea that they should create a business to deliver fresh-from-the-oven cookies.

While her marketing major boyfriend possessed an entrepreneurial drive, Chen was working her way through college and never anticipated that her path would lead her to founding a company. But I’ve often heard it said that life is a question and how you respond is the answer—so Chen reframed her journey accordingly.

As the company grew more successful and took on its first outside investment in 2008, Chen realized she had to take the proverbial oven mitts off. She couldn’t help grow the company if she only stayed in the kitchen.

She and her co-founder asked themselves what they spent the most time on and what they didn’t love doing, and they decided to off-load their hiring processes and get help with the overall human resources function. Next, they got someone to handle accounts payable and receivable as they weren’t experts at accounting, nor was their work there helping move the business forward.

Chen initially wondered that, if baking was her value and she abandoned it, how was she going to add value to the business? She later found that by setting aside the things that didn’t give her energy to people who actually enjoyed them, she was able to step further into her genius zone. When she handed over certain tasks and watched those people do it 100x better than she felt she could, it was beneficial both for her business and helping her invest in others.

How connections can produce a butterfly effect

In Tiff’s Treats first few years of operations, they opened a satellite location—a walk-up on a busy strip that didn’t offer delivery. The brand wasn’t established enough for an offshoot and the location failed. Tiff’s Treats was also on a month-to-month lease with their main kitchen and was kicked out of their spot. If they were unable to find another space to bake and deliver from, they faced going out of business entirely.

However, the landlord of the failed satellite location had a good friend in real estate that worked with them to find a new space. Additionally, the husband of the woman that had been working on their books had a business partner who later became Tiff’s Treats’ first investor and helped them open several locations.

Stress forces you to think outside of the box and go beyond your comfort zone in order to start considering things differently. A lot of times we get stuck in failure, but we have to remember it isn’t the end of the road. Leon, Chen’s partner and husband, believes that there is no choice but to succeed. You have to solve the problem or go out of business, so it forces you to come up with creative solutions. 

Overthinking is dangerous—and why opposites do attract

While Chen and Leon are aligned on life’s bigger things, they both bring different skill sets, interests and personality profiles to the table. This helps them to grow both separately and together, in terms of business and life. For example, Tiff’s Treats was presented with a partnership opportunity. Leon was only present for the initial idea. Chen was there for the entire meeting, and after churning through the details thought they should pause on the idea. When she told Leon, he replied it was too late—he had already texted the other business owner and conveyed his excitement, so Tiff’s Treats made it happen.

Chen said there was a good chance that if they had simply paused, the opportunity would never have surfaced again. And while it’s important to be thoughtful, sometimes you just need to responsibly go and trust yourself to make that decision.

What’s your purpose?

Along the way, Tiff’s Treats realized they weren’t just selling a convenient way to get fresh-from-the-oven cookies. They were providing a connection point for people, in what Chen refers to as “warm cookie moments.” Her business enabled people who couldn’t physically be together to still show up for their loved ones and communicate that they cared for them and were thinking about them. What better way to say “I love you” than with warm cookies?


Jill McDonnell

Jill McDonnell is a Chicago-based content writer and communications professional. She has a bachelor’s degree in magazine journalism from the University of Missouri-Columbia and a master’s degree in public relations and advertising from DePaul University. She is currently at work on a psychological thriller novel.






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