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Founder’s Friday featuring Caitlin Hoffmann @ Wandering Eye Co

Caitlin Hoffman

Please provide a brief description about your company.
Wandering Eye Co. is a travel agency dedicated to creating personalized itineraries for travelers seeking unique experiences around the world and close to home. Chicago is currently home, however my curious nature keeps me constantly traveling – absorbing and reporting back.

Two hashtags that best describe you.
#wanderlust #worldtraveler

What do you consider your greatest achievement?
Identifying a way to match my passion with my professional experience which led me to take on the risk of starting a business in a new industry. But it paid off – hence Wandering Eye Co

What is your idea of perfect happiness?
Late afternoon on the beach. Refreshing cocktail. No plans but sunset

Whom do you most admire?
People who meet adversity with strategy and wit

What are your top tips for balancing work and life?
I am big on calendar time blocking. This help me to better understand how long certain tasks take and helps to prioritize projects based on deadlines. Allows me to hold myself accountable and more confident to take time for myself.

What is something new that you learned about running a business this year?
Wow-what have I not learned this year. Travel was completely disrupted due to COVID. I was able to establish myself not as only a trusted advisor on how to navigate shifting of trips and cancellations, but also as a destination expert for travelers looking for inspiration when ready to get back out there and explore the world.

What is your most marked characteristic?

What is your motto?
Do what you love & love what you do

What is a legal mistake you wish someone warned you about?
Get your ducks in a row at the beginning – everything from trademark to terms & conditions. Be prepared for the worst, hope for the best and find a lawyer who gets your business.

When running your business, what do you struggle with most?
Running your own business you wear a multitude of hats. It has been so valuable to leverage experts to lean on for the parts of the business that are not my expertise. Cheers to you Meyer Law!

What advice would you give to yourself at 25 years old?
Try everything – do not dwell on the option of failure. But focus on the tools you can add to your toolbox so that when the stars align – you are the best woman for the job.

Tricia Meyer 301

Tricia Meyer is Founder + Managing Attorney of Meyer Law, one of the fastest growing law firms in the United States. Meyer helps entrepreneurs and technology companies from startups to large corporations with day-to-day matters and notable clients include companies that have appeared on Shark Tank to companies gracing the Inc. 500 to some of the largest companies in the world.

Tricia has been named on the Forbes Next 1000 list, is one of the Most Influential Female Lawyers in Chicago according to Crain’s Chicago Business and been recognized as a top 10 technology lawyer.

As an entrepreneur and a lawyer, Meyer has a unique perspective and has mentored thousands of startups and scaling companies at tech incubators and accelerators across the United States such as 1871, WeWork Labs and Techstars. Tricia has been featured in Inc., Crain’s, Chicago Tribune, NBC Chicago, American Express OPEN Forum, and more. Learn more at and follow Meyer Law’s story on Instagram @loveyourlawyer.