Entrepreneur Escape Weekend | Nantucket

by Sara Boyce

Entrepreneur” is such a big word.  It seems everyone (and their brother) puts it on their LinkedIn profile. Have you ever sold anything for money?  You don’t have to be Richard Branson or Steve Jobs to be an Entrepreneur.  Do you own a small business?  You’re an Entrepreneur.

There’s a certain archetypal energy to a person who has the entrepreneurial spirit.  It’s certainly not a choice and it’s not constant.  I think it’s woven into a person’s being.  For me, when an idea takes hold and starts a-buzzing, the road map lays out.  I can see the end result waaaaay off in the distance, and I have ideas on how to get there, who the helpful players will be along the way, and how to expand from an idea, into a real live business… when the juices are cooking, it’s exciting.  The energy rises and I’m filled with passion –  but, it can be solitary at times.  Very, very solitary.  And it can lead to lots of doubts.  Should I do it?   Is it a good idea? Will others agree and (more importantly) will they pay for it?  What is involved in achieving liftoff, funding, and the necessary promotion?  Pepper that with repeated thoughts of “Should I just get a regular job?”


Enter the 3E Entrepreneur Escape weekend on Nantucket, a collaboration between Meg Blair, Holly Finigan, Jason Bridges and Justin Joseph Taylor.


Roughly 40 people came together for various portions of the weekend to connect by sharing ideas, triumphs, doubts, inspiration and skills as we pursued existing or new projects.


We were wined (and beered). We were dined. We socialized at The Harborview before dinner and at The Second Story (upstairs from BookWorks) where I had my first experience with Greg Margolis’s Nantucket Culinary Center. I’ll definitely be checking our more of their offerings! Greg planned the menu with the dinner hosted by Cisco Brewers and during each course, we voted on whether we preferred a Cisco Beer or a Nantucket Vineyard pairing. (As you might imagine, it was pretty evenly split!).

handlebar 3E

We experienced the HandleBar Café for dinner. Yes, for dinner! David M. Handy transformed the coffee bar into an evening Entrepreneurs Supper Club and we dined on delicious food from Island Kitchen. This was a fabulous way to get to know our fellow Entrepreneurs.


The weekend was filled with big lessons, small nuggets of wisdom, suggestions and warnings, and many new relationships.  Here is a recap of the speakers…


Trish Fontanilla launched us with a passionate lesson on how to build, know, and expand your tribe.  A Community Builder, Trish is really a Brand Ambassador for whatever company she is representing.  A proponent of knowing the value of your time (in Massachusetts the average volunteer hour is valued at $27.80), she asked us the sexiest question of the entire weekend, “What is your superpower?” Once you know the answer, can you clearly articulate both the personal and the professional version?

money talks

The Clash’s song, “Should I stay (comfortable and not risk) or should I go (forward)” runs through every Entrepreneur’s head at times.  (Often, like an earworm, it’s on repeat.)  Jamey Bennett, formerly of LightWedge and Lending Tree, and Brian Mullen, of Therapeutic Systems, shared very honestly about the benefits and frustrations of launching businesses with investor money.  Of all the speakers, Jamey had cast the widest financial net when he launched Lending Tree by raising $100 million from investors like GE and Goldman Sachs.

Entrepreneurs can start businesses with their own money, with borrowed money, or by accepting investor money.  Most all of us wonder, at some point, if we should seek investor money because we know we could do more with additional funds?  Jamey and Brian shared about the obligations and responsibilities that come with accepting investor money.  Both were surprisingly frank about some of the downsides.  There are real risks when an Entrepreneur devotes 100% of personal time to a business.  Often times, in the desire to succeed and realize a gain for investors, personal health, relationships, and well-being can be sacrificed.  First, you see the vision and feel the itch. Then, it’s a combination of taking risks, building relationships, branding ourselves, setting intentions, and working as hard as possible (sometimes non-stop)….  At the end of the day, we are all human, and sometimes Entrepreneurs win and sometimes we lose.

kate weiler

Kate Weiler, of Maple Water, reminded us how important it is to do the work.  Research your idea and the competition.  Talk to people.  If someone can talk you out of it, it’s probably not meant to happen.  Understand that you’ll probably never feel completely ready, and there is a certain point where we all need to channel our inner Swoosh and Just Do It.  Then, once you’ve launched your business, if you have a partner, take time to nurture the relationship.  It’s important.  As important as a marriage.  Realize you might each have different goals and methods of achieving them, create a Founders Agreement, learn how to communicate with each other, and celebrate each other’s skills.

brand human

Jasmine Takanikos, of #BrandHuman, guided us through a 3-hour intensive on Branding in today’s Trust Economy….  In this brave new world of social media, we all have the ability (and responsibility) to self-market.  Every time we post, we send a message.  Jasmine walked us through a number of exercises that all supported her recommendation to BE AUTHENTIC (after all, her business name is “Brand Human”).  Let’s be honest.  It’s easy to throw a narcissistic, selfie-based “brand” up on social media.  But is it authentic?  Is it YOU?  Use this gut check: does your online persona match your offline reality?  Do the work.  Dig deep.  Figure out exactly who you are, what you want to do, what drives you, and set sail.

yellow prod 1

Laura Cunningham and Chris Wendizcki are the dynamic duo behind Yellow Productions, a video marketing company.  This creative team has produced some Nantucket videos such as “All About The Plates” that tell stories designed to elicit emotions and inspire viewers to act.  Again, we heard the message to plan your message, “90% of successful video marketing is done in pre production” and learned about an additional way to connect with customers.  The two are also responsible for the #MakingTheJump Entrepreneurship video series and gave the attendees a taste of what it’s like to tell an entrepreneurs story in just two minutes through video digital marketing. You can see more here.

marsha 3

Marsha Egan, of The Egan Group, is a successful Coach and Time Management expert with a national reputation. A “Washashore”, Marsha offers regular classes through the Chamber of Commerce and at Mitchell’s Bookstore.  Each day, we get 24 hours.  That’s 86,400 seconds.  How will we spend our time?   We all have a series of tasks that range in importance.  While everyone finds themselves doing the mundane at times, we have a choice in how we spend our time.  Organization can improve our efficiency and success.  Marsha walked us through a series of exercises to teach us how to move out of “Crisis Control” to focus on the “Important but not Urgent” tasks that will bring us success.  Get clear on the 10 Year goals; break it down into 10 Months, and then into the next 10 Hours.  The tasks we choose on a daily basis should always be leading towards our 10-month goal and be driven by our 10-year goals.

trish 2

Perhaps none of us at the 3E Entrepreneur Escapes weekend feel employable, in the traditional sense,  because we all want to run our own businesses, in our own way.  So what’s next?  I’m pretty sure we will all be starting another business sometimes soon.

all photos by Kit Noble 

 Sara Boyce, MBA, MPH brings her creative vision and personalized attention to each client.  With a 24-year career in marketing, her approach is strategic, collaborative, and effective. Coincidentally, she has also spent the last 24 years without flour and sugar and coaches people who want to transform their bodies and live a healthy lifestyle. A long-time Nantucket resident, Sara eats clean and healthy, but rarely turns down a glass of good wine or the occasional cream sauce. She has a crazy belief that a life that prioritizes beauty, health, and wellness is actually A Delicious Lifestyle… Email her at Sara A T SaraBoyce DOT com

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