Heather Dolland: New York’s Finest Food Crawler

Heather DollandJob security isn’t everything, even in New York City, one of the world’s most competitive job markets. And sometimes you have to risk it all to figure that out. Just ask Heather Dolland who turned down a promotion from her environmental consulting firm, where she’d been for more than a decade, to start her own online company.

“There’s never a right time to leave. Usually we just need a little push out of the nest. No matter where this goes, I can say I gave it a 110%. My biggest regret would have been not trying,” Dolland says emphatically.

After 20 years in the US, Dolland’s Grenadian accent may have mellowed but it’s still music to the ears. She moved Stateside in 1995 to study architecture only to find while doing her thesis that her dream turned into a nightmare. So she switched gears and launched into environmental science, getting a Masters from the NY Institute of Technology.

She began her career with the NYC Department of Environmental Protection before moving to an environmental consultancy where she was a Business Development Manager for 11 years.

Halfway through her time at the firm, Dolland took on a side gig. “I bought a house in Long Island by myself, but I had no idea how expensive it would be. Three months into the purchase, a friend from Grenada who promoted wines and spirits asked me if I could help her with promotions in Long Island so I became a brand ambassador on nights and weekends, mostly as a means to supplement my income.”

“I really wanted to go for it, but I was so nervous to leave my job. It never seemed to be the perfect time. Then my manager offered me a promotion but made it very clear I would have to drop ‘my distraction’ and focus 150% on my work. I guess it was what I needed to hear because I said ‘Thanks, but no thanks,’ and I knew then I was turning down the money to do something I really loved. Hopefully the money will follow.”

Dolland was so good at brand evangelism, hosting events, spirit tastings and launches, she took on several brands in the Bacardi family. It wasn’t an issue with her employer because she was doing the promotions outside of working time and there was no conflict of interest. But increasingly she realized which work she was more passionate about.

“Even though I was making progress and moving up in the company, I knew I had topped out. I could Heather Dolland with her booksee what the rest of my life was going to look like. I liked what I did, but the idea of living this life for the rest of my life was frankly a little depressing. I was by no means reaching my potential,” she explains.

When the work day ended, Dolland looked forward to the evenings which were spent promoting her clients products. “No matter how long the day had been, I always had energy. I loved it. I had this gut sense that this is what I was meant to do.”

The inspiration for her shift came during a visit to South Beach, Florida, with her mother who lamented they didn’t have enough time to try all the great restaurants. “I remember saying to her, ‘Who says we have to eat the entire meal at one place? Why can’t we enjoy each course as we like?’ So we did just that and had a food tour of the restaurants.”

As a huge foodie herself, it occurred to Dolland that she could market a more formal experience to others. And so, while still working as an environmental consultant, she launched a website – All the Tastes of New York – offering a food crawl concept. Clients enjoy each course at  a different restaurant within a few blocks of each other in various neighborhoods like Hell’s Kitchen and the East Village. Dolland arranges everything directly with the restaurants.

“I feel like my brain is a portfolio of restaurants. I have eaten through the Zagat – from Afghanistan to Zaire so I know my stuff! I do a lot of bachelorette parties and themed events like dining at places where there are celebrity chefs or eating a specific cuisine such as Italian. I tailor the experience to what the clients want and everything is built in.”

Heather Dolland Book SigningInitially, the business was just an outlet, something that gave her joy but, as the demands on her time grew, Dolland knew she had to choose.

“I really wanted to go for it, but I was so nervous to leave my job. It never seemed to be the perfect time. Then my manager offered me a promotion but made it very clear I would have to drop ‘my distraction’ and focus 150% on my work. I guess it was what I needed to hear because I said ‘Thanks, but no thanks,’ and I knew then I was turning down the money to do something I really loved. Hopefully the money will follow,” she laughs.

Starting a small business is scary for anyone, but Dolland had now lost the salary that was funding All the Tastes of New York. Because she had seen the day coming, she had extended lines of credit for her business while still employed. But without the comfort of her paycheck to fall back on, she lived lean and got serious about money management.

A year and a half after she left her secure job as an environmental consultant, Dolland is seeing the Discovering the New York Craft Spirits Boom Book Coverpayoff of all her hard work. Match.com was an early client and, as the culinary experience she has created lends itself to movement and communication, she has many corporate clients doing team-building events. She has plans to replicate the concept in other cities like Las Vegas and South Beach and has written a book, Discovering the New York Craft Spirits Boom, promoting small distillers in the New York area as a way to spread word about her business but also to integrate locally produced beer, wine and spirits into her food crawls.

“If I think about the journey I’ve been on since I left my job, I know now that you can’t have one toe in. It’s all or nothing. You only really see all the aspects that you need to manage when you are fully in it. It’s not really possible to run a business effectively when you’re doing it on a part-time basis. I still feel like I’m still figuring it out but having so much fun doing it.”

Tips from Heather Dolland
  • When you start a business in a new space, be open to evolving. Don’t stray so far afield that you lose sight of who you are you. Try to build on your competencies.
  • The irony of having a small budget is that it keeps you very cautious. If I had a ton of money, I would have burned through it.
  • While it’s not sustainable in the long run, having another job enabled me to evolve slowly and cover big ticket items early on. My business wouldn’t have survived if I didn’t have that salary because I wouldn’t have been able to afford all the mistakes I made early on.

Watch this video to learn more about All the Tastes of New York.