Founder Spotlights: Insights from Annie Cheng, founder of The Table Less Traveled

Grasshopper Bank
Grasshopper Bank
Published in
5 min readMay 28, 2020

In case you haven’t heard, we’re hosting a virtual event series in partnership with the NY Tech Alliance! Hosted by NYTA’s Andy Saldaña and Grasshopper Bank’s Micah Baldwin, “Don’t Panic, Let’s Talk” is a bi-monthly check-in for tech founders, entrepreneurs, and small business leaders looking to have candid conversations while we all navigate a global pandemic.

We all make decisions about our businesses everyday that appear clean cut to others. While the end result may be clear, the process of making those decisions is usually a bit more complicated. We were grateful to have a candid conversation about this with Annie Cheng, founder of The Table Less Traveled, a boutique, small-group tourism company, which has offered culinary-centric tours to amazing destinations for the last five years. The trips are thoughtfully packaged so all travelers need to do is show up and be present. They’re intimate in terms of group size, plus they’re often hosted at people’s homes. And The Table Less Traveled helps to support small businesses and independent freelancers such as guides, chefs, and hosts all around the world.

As we all know, travel was one of the industries hardest hit by the pandemic. With the onset of the COVID-19 pandemic, the tours offered by The Table Less Traveled came to a halt with no definitive end in sight. Annie’s willingness to examine her emotions and mindset as she navigated this challenge made for some insightful takeaways that we’re excited to share with you here.

Do the work to resolve conflicting emotions

Every entrepreneur knows your business can often feel like your baby. Building a new company takes a lot of determination and The Table Less Traveled was finally selling out trips right before the pandemic happened, a hard earned milestone of success for a founder. When travel came to a screeching halt due to coronavirus, Annie was devastated. But she was grappling with another emotion as well — guilt. Annie says, “I felt shame that I was so upset about this situation for me and the people we support through our business, when so many others were being more drastically hurt. There were people going out of business overnight, laying off hundreds of employees and people whose family members were dying of COVID-19. I felt guilt for my sadness”. Annie recognized these feelings and the stress the juxtaposition of them was causing her. Even though this issue seemed to stem from her business, what Annie needed was emotional support. Her family and her therapist were there to help her process her grief. Only then was it possible to move forward with making sound business decisions.

Don’t be afraid to embrace new perspectives

Like most travel-based businesses, Annie didn’t know what the next move for The Table Less Traveled would be. Her non-stop, unstructured brainstorming led to several middle of the night ideas and ultimately, the concept of live cooking classes aligned best with her mission of providing shared cultural experiences. But this was still a major change. Previously, the website was simply a way to validate that the company existed. Suddenly, it became a destination for people to find what they’re looking for and engage with the community. Annie acknowledged, “I had been so involved in every aspect of the business… I realized if we were going to make this change quickly and effectively, I needed to let go a little bit”. She recognized that she was not the right person to handle the UX and data analysis of the website and that she needed to delegate. Now, website updates are an iterative process, regularly influenced by user feedback. Trading in perfectionist tendencies for a new perspective, Annie has been impressed by her newly formed team’s talents and passions. She tells her team, “I will lead by example in the things I’m good at, but I need YOU to lead me by example in the areas where you’re an expert”.

Remain open to others and they may surprise you

Annie wanted to find a way to create value, maintain the business, continue paying employees, and support her partners around the world. She had no idea if her clients and partners would have an ‘appetite’ for live cooking classes. When the live cooking classes launched, Annie said they were met with overwhelming generosity and understanding and compassion. “For hosts across the world — in Peru and Italy especially — this was not about the money but about humanity and how we can make a difference and keep people connected to one another”. It’s been incredibly effective. The classes are taking place in the chefs’ homes, complete with pets and kids, which has helped fuel the intimacy of the experience. Hosts and attendees alike have had honest conversations about how COVID-19 is affecting their lives. Would-be-travelers are getting a glimpse into how the virus is impacting tourism-dependent economies. And The Table Less Traveled is reaching a wider audience now, extending an interactive cultural experience to those who may not have been able to travel otherwise. Those hosting the live cooking sessions are receiving 50% of the “pay what you can” proceeds. Annie says she’s “Proud that we’ve stuck to our mission and haven’t been advantageous or opportunistic in negative ways… I’m proud that what we’re doing supports real peoples’ lives”.

Annie has shown us that reflecting on your own feelings and your natural tendencies can go hand in hand with good business sense. Together, they can have a lasting positive impact on your startup. What do you think? We’d love to hear!

Our next virtual event in the “Don’t Panic, Let’s Talk” series will be with Julia Niero. Julia Niiro is the founder and CEO of MilkRun, an online marketplace and distribution technology that makes it easy to buy food directly from local farmers. She started MilkRun in 2018 as an Oregon farmer with an idea for a better way to get local groceries to urban markets. Fast forward to 2020 and Julia has given a TEDx talk, partnered with Social Impact Capital, and joined the Techstars Anywhere program. MilkRun is now gearing up to go national, and we’re excited to have her join us to share her experience with us. Register here!

In the meantime, please have a look at some resources we have pulled together that we’d like to share with you: Grasshopper Bank’s Resource Guide — A compilation of the best articles, strategies and tips for managing a business and maintaining your mental well-being during challenging times.

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Grasshopper Bank
Grasshopper Bank

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