Caitlin Crowe

Don’t wait until everything is perfectly ready to start something or you’ll never start it. What’s holding you back?


Caitlin Crowe of Portland, Maine is the co-founder of Topo Pino, a tranquil retreat bordering the White Mountain National Forest in New Hampshire. As a certified health coach, Caitlin is passionate about providing a beautiful space for individuals to reconnect with nature and oneself.

A strong work ethic and overall zest for life helped Caitlin Crowe pursue her dreams via various avenues. Crowe graduated from Dartmouth College in 2008 with a Bachelor of Arts in Human Geography and a minor in Public Policy focused on Social Justice. While at Dartmouth, she co-founded an education nonprofit in Ghana, West Africa. This was her first entrepreneurial venture, although it would be several years until the idea for Topo Pino formed.

Instead, Crowe kicked off her finance career as a Private Equity and Venture Capital Services Associate at Silicon Valley Bank following Dartmouth. From there, she entered the world of investment banking and took on an M&A Sell-Side Analyst position with Raymond James & Associates in Boston. Recognizing a need for greater work/life balance, she then spent five years at Citizens Financial Group as a Portfolio Manager in the Nonprofit and Healthcare Division. Crowe continued her involvement in the Boston startup scene, all while serving as a Board Member for the Boston Chapter of the Dartmouth Entrepreneurial Network until 2017.

The spring of 2017 offered Caitlin Crowe the opportunity to spread her wings once again. She accepted a position as Vice President and Relationship Manager on the Middle Market Commercial Lending team at KeyBank in Portland, Maine. The new position would allow Caitlin to develop relationships with growing Maine companies and return closer to her family’s New Hampshire property — a peaceful destination she’d loved since childhood. In fact, she’d spent many summers hiking, kayaking, and swimming on this 30+ acre haven in the mountains. The property was originally named Topo Pino in the early 1900s during its time as the summer location for the Fannie Farmer Boston Cooking School run by Janet McKenzie Hill.

Crowe was in the process of pursuing her health & wellness coach certification around this time, and realized the property would be an ideal outlet for her creativity and desire to inspire others. Topo Pino retreat was officially born in 2017— the result of a collaboration between Caitlin and her mother, Lucy. Now, one year later, Caitlin Crowe couldn’t be happier to live, work, and build community in Portland, Maine, which is a short drive away from the retreat.

When she’s not at the office, Caitlin can be found at local networking events, hosting Dartmouth alumni events, enjoying live music with friends or hosting wine & cheese soirées. On weekends, she enjoys all of the beauty that Topo pino has to offer while constantly planning for its future. She’s nurtured partnerships with local farmers to improve farm-to-table offerings, fostered relationships with Tentrr to create a unique glamping experience, and works closely with Mayflower Venues to provide a beautiful wedding destination on the Topo Pino grounds.

In any remaining spare time, Crowe likes to go on outdoor adventures with her camera. While she’s out and about, Caitlin Crowe enjoys practicing her photography skills and observing the creativity of others in various formats. She is particularly fond of photographing the natural beauty found at the Topo Pino retreat and in the surrounding White Mountain National Forest. She’s also an avid cyclist and enjoys riding her Peloton bike indoors during the week.

Moving forward, Caitlin hopes to help others unlock their creativity, achieve their wellness goals, and live fulfilling lives while simultaneously expanding her creative endeavors and pursuing personal and professional growth.

Where did the idea for your company come from?

Topo Pino is a destination – a destination not just to visit, but to reconnect with nature and oneself. My family has owned the Topo Pino property for over 50 years. I was inspired to launch Topo Pino as a destination for personal and group retreats as well as a non-traditional wedding venue during my studies to become a Wellcoaches® Certified Health & Wellness Coach. Topo Pino was always a place of retreat for me in the summer as a child. I spent every summer there hiking, riding my bike, kayaking, running, dancing in the fields and swimming. I grew up in York, Maine and attended Dartmouth College. While at Dartmouth, I studied in Lyon, France and the Czech Republic and spent my off-term in Ghana where I co-founded an education nonprofit. Upon graduating in 2008, I moved to Boston where I lived for nine years. While in Boston, I became further immersed in the world of entrepreneurship through my time working at Silicon Valley bank and board role through the Dartmouth Entrepreneurial Network. In realizing my dreams with Topo Pino, I set out to move back to Maine to be closer to the property and turn my vision into reality.

What does your typical day look like and how do you make it productive?

I have a full-time finance career in Portland, Maine in addition to my responsibilities with Topo Pino. My typical weekday involves waking up, enjoying a cup of tea while I get ready to exercise, and then hopping on my Peloton bike for a 45 minute class. I recently completed my 750th ride! After a good post-ride stretch, I get ready for and walk to work. I love walking as much as possible. It provides me with the much needed time to call my mother and discuss what’s next for Topo Pino— whether that’s planning for our next guest or dreaming into the future. Once I get to work, I settle in for my day which is often full of client/prospect meetings, but I get as much done as possible while in the office. The rest of my time is spent on the road. I work with growing Maine companies typically $10 million and over in revenue. I greatly enjoy building new and deepening existing relationships. After work, I often attend networking events. I also serve on two boards, the Maine Women’s Network and Dartmouth Club of Maine, so I am frequently attending and hosting events. If I don’t have an event, I usually run any necessary errands and then head home to work on Topo Pino. I try to get to sleep by 9:00 pm so I am refreshed the next morning.

How do you bring ideas to life?

I love brainstorming and am constantly thinking of new ideas. In order to truly bring an idea to life, I let the idea simmer while I research its feasibility. I closely study the local market, any relevant comps, talk to potential target customers and gather as much information as possible. Once I confirm that it is doable, logical and fitting with the Topo Pino business model, I don’t hold back. I am an all-or-nothing sort of person, so once I decide to do something I am all in. When I was pontificating Topo Pino, the more I spread the word the more positive feedback I got which helped drive the direction of the business. At first, I was completely focused on retreats and didn’t realize its potential as a wedding venue or glamping site. Over time, I realized it is a perfect destination for couples interested in escaping the city without the hassles that go along with traditional camping. Tentrr agreed with us and we had our first summer of campers this year! Through many other conversations, people kept suggesting I consider opening it up to weddings. That led to discovering Mayflower Venues (founded by a fellow Dartmouth alum!) and realized it was a wonderful fit for Topo Pino. In summary, I would highlight the power of doing your research and talking your ideas through with others before diving too far into a project and realizing another direction may have been more appropriate. Share, listen and digest. Then do it!

What’s one trend that excites you?

One trend that really excites me is the idea of the non-traditional– everything from non-traditional vacations to non-traditional weddings– people don’t want the same old experience as the next person; they want a unique experience of their own. Topo Pino embodies this concept and allows for people to experience non-traditional, comfy camping, allowing couples (or a solo camper) to have a personal retreat nestled among our tall pines. There is only one comfy camping site and one Topo Pino, so it’s an experience that no one else can duplicate. The same goes for Topo Pino as a non-traditional wedding venue. I can’t wait to see what couples dream up and execute for their Topo Pino weddings. We want couples to have a truly unique wedding that embodies them in every way.

What is one habit of yours that makes you more productive as an entrepreneur?

Prioritizing my sleep definitely makes me more productive in my full-time career and as an entrepreneur. I need to aim for 8.5 hours of sleep per night. I notice a big, negative difference with even 7.5 hours of sleep. With 8.5 hours, I am much more likely to exercise before work and be very energetic all day. Caffeine (I drink tea) never masks a lack of sleep for me. There is no substitute for a good night’s sleep.

What advice would you give your younger self?

Don’t wait until everything is perfectly ready to start something or you’ll never start it. What’s holding you back?

Tell us something that’s true that almost nobody agrees with you on.

Work/life balance is possible. I think finding work/life balance first starts by identifying a career, opportunity and team that embrace this mentality. If you are striving for “balance” in a position that expects you to work 80 hours per week, that is less realistic. Create your balance through first identifying what balance means to you. Balance to one person may have an entirely different meaning to someone else. Find your balance.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Carve out time not only for a good sweat but also creativity. I am most inspired after a good workout to do something creative such as photography, write a poem or play the piano. Harness the power of endorphins into your own creative endeavors.

What is one strategy that has helped you grow your business?

Instead of reinventing the wheel, we decided to initially launch by partnering with two existing startups – Tentrr and Mayflower Venues. This prevented us from shouldering the startup costs and priorities on our own, while also providing us with a broader marketing platform to spread the word about Topo Pino.

What is one failure you had as an entrepreneur, and how did you overcome it?

When first starting Topo Pino, we didn’t have a single reservation for over a month. I got very discouraged and felt all my efforts were for nothing. Then one day– a reservation request! We have been happily booked ever since. Key takeaway? Good things come to those who wait. Don’t give up and keep moving forward.

What is one business idea that you’re willing to give away to our readers?

A tablet for the elderly that is designed to help someone effectively navigate through their day while providing entertainment such as audio books, news and music. The differentiating factor is that it could be programmed with a recording of a loved one’s voice, so the tablet speaks in that voice and provides the person with a greater sense of comfort and familiarity.

What is the best $100 you recently spent? What and why?

I would say the cumulative $100 I’ve spent on coffees with new and existing connections. Those conversations lead to brainstorming, new ideas, further introductions and it just keeps going. Business and entrepreneurship is all about relationships and understanding what your target audience wants.

What is one piece of software or a web service that helps you be productive? How do you use it?

The Peloton bike has been a game-changer for me in terms of exercise and productivity. I can exercise when I want in my own home and track my progress over time. My day isn’t complete without a good sweat and moving my body to music. With each ride, I feel calm, strong and invigorated for my finance career and for Topo Pino.

What is the one book that you recommend our community should read and why?

One of my favorite books of all time is Siddhartha. Siddhartha helps one realize the importance of the journey in life, the difference between seeking and finding, the interconnectedness of the world, and how everything we do releases our unique frequency into the world. We all have our path with lessons to absorb and grow from in life. “Your soul is the whole world.” ― Hermann Hesse, Siddhartha

What is your favorite quote?

“Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” – Mark Twain