Alec Stern, Entrepreneur, Speaker, Investor and Influence 100 Authority

June 21, 2019
Influence 100 Authorities
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I met Alec Stern in Reno, Nevada during a conference where we were both speaking to a group of entrepreneurs. His credentials were immediately impressive to everyone present. Alec is one of the founders of Constant Contact, a multi-million dollar email marketing company that revolutionized the way small and medium sized businesses are marketed. Beyond his impressive track record he was an engaging and authentic speaker. His message to the entrepreneurs in front of him was filled with encouragement and business tactics the audience could use immediately to improve their business. In other words? Alec impressed me by being both knowledgeable and personable, often a rare combination.

As Alec tells us in his Editor's Spotlight, he broke his back playing high school football which taught him some valuable lessons and changed the course of his life at a pivotal point. Knowing how to face setbacks and move forward without losing momentum is a key talent successful entrepreneurs have.

As the Editor-in-Chief of Influence I am passionate about sharing the story behind the success of entrepreneurs, speakers, authors and professionals from all walks of life. I am incredibly honored to share a peek into Alec's story and I'm certain you'll enjoy meeting this impressive and delightful entrepreneur, speaker and investor.

Sharon Ricci,

Editor-in-Chief and Founder of Influence

Alec, what makes you different as a professional? What makes you stand out?

I am fortunate to have a business background and experience that is well-rounded and encompassing. In my career, I have co-founded and scaled companies, raised funds, and successfully exited multiple times via acquisition and IPO. I meet and speak to thousands of entrepreneurs and startups each year. When I engage in a conversation with an entrepreneur or team and identify a problem area preventing them from going to the next level, I help them discover the breakthrough opportunities they are looking for. I regularly spend time thinking of ways to improve on existing products and better execute services. I make it a point to be a great listener; to be present, approachable, supportive, open to new ideas and to inspire others.

Where did you grow up?

I was born in Boston, Massachusetts, grew up in Connecticut and moved to New Jersey as a teenager. After graduating from Syracuse University in Syracuse, New York, I moved back to Boston and have been here ever since.

Did your home town make an impact on your life and what you are doing now?

My home town communities most certainly made an impact on my life. I was able to get started as a young entrepreneur mowing lawns, shoveling snow and washing and detailing cars. At an early age, I realized the value of relationships, learned how to market my services, negotiate, delight the customer, up-sell, cross-sell, manage my time, build a team and, ultimately, corner the market in my neighborhood.

What key events or memories changed the course of your life? Were there any driving factors that make you who you are today?

I broke my back playing high school football which taught me some valuable lessons and changed the course of my life at a pivotal point. It was the end of the season and college scouts were evaluating me, so what I thought was my life path vanished in that moment. It was extremely painful for me both physically, and mentally. While I recovered, I had to formulate a whole new passion and a new plan; one that I could commit to 100%. In that journey, I learned important life lessons that would be invaluable to me going forward. It taught me the value of perspective, how to handle disappointment, embrace change, overcome challenges and to be resilient.

Do you have or have you had a mentor? Who is/was it and what do they bring to your life?

I have had too many mentors to list. My mother was my first mentor. She was a small business owner who taught me about entrepreneurship and the value of good old-fashioned hard work. I watched how she built her business by listening, personalizing and customizing her services to “wow” her customers.  Through different phases of my life I have looked up to folks that I either aspired to emulate, could learn from and help me grow both personally, and professionally. What I learned from these individuals collectively has shaped who I am today.

Do you consider yourself a mentor? If yes, what is the most important thing you can share with someone seeking guidance?

Absolutely. I mentor and advise all stages of startups, small and even large businesses. I have been doing this for most of my career. I speak to thousands of entrepreneurs each year at events all over the world and my involvement in several startup accelerator programs is very rewarding. The most important piece of advice I can give is to make sure you focus on the one core thing you will offer to your target market. Listen to your customers and you will get valuable feedback. Act on it, and revenue will follow. Your business will grow from there.

If someone was to sum you up professionally, what descriptive words would they use?

Highly experienced, leader, strategic, analytical, innovative, ambitious, committed, great listener, big picture thinker and detail-oriented.

100 years from now how would you like to be remembered?

I’d like to be remembered as a gentleman. A generous, kind, caring and fair man.

Do you have a favorite saying or quote? If yes, please share it and if possible, tell us why it has made an impact on you.

“Accomplishments are something to build on, not rest on.”

These are words I live by. Any accomplishment is a beginning that can propel you to your next one. If you have a successful call or meeting with a prospective client, partner, investor, etc., harness that feeling, immediately make another call, book another meeting etc. Let your momentum push you forward. And, be sure to celebrate your wins both large and small.

Have you ever made a wrong turn professionally and had to course correct? If yes, please share the experience with us.

Absolutely. The wrong turns are just as important as the right ones. As we say “fail fast and fail forward.” Learn from all of your experiences. If you’re not failing occasionally, you’re probably not trying hard enough.  

Early in my career, I was in sales and had cultivated a large pipeline of business set to close within the year. I had an offer to join a startup which could not guarantee that I would be paid at all or that I’d have a job within six months, much less enjoy a successful long term outcome. I chose to decline the offer. I later learned I had made a big mistake which taught me to consider opportunities more carefully and to be more comfortable with taking risks.

What do you consider to be some of the highlights of your career so far?

One big highlight was being a co-founder of Constant Contact. Our mission, which has always been a passion of mine, was to help small businesses succeed. We started with 3 people in an attic in Brookline, Massachusetts to go on to build a company that we took public 10 years later and then sold for $1.1 Billion. A major part of that was experiencing success with others on the journey. As they say, “If you want to go fast, go alone. If you want to go far, go together.” Through stress, missteps and pivots, it’s the people at your side that are most important. I consider the amazing, rewarding and lasting relationships I’ve maintained with talented people I’ve worked with closely over the years to be a true highlight.


If you had to choose a totally different career than the one you have, what would it be and why?

I would be a drummer!  I have been playing the drums since I was 8 years old. It’s an important creative outlet for me and I always love to jam with others on, or off-stage.

What are you looking forward to professionally? What are you excited about?

I am very excited about delivering keynote addresses Worldwide at conferences focused on entrepreneurs, startups and small businesses.  I’ve become known as America’s Startup Success Expert for my talks at conferences like Secret Knock, Powerteam International, City Summit and Habitude Warrior. In 2019 I’ll be the Keynote speaker at three out of the top five “Inc. Magazine Must Attend Conferences for Startups and Entrepreneurs in 2019.”  I really enjoy sharing my knowledge, expertise and early days, lessons learned experiences with audiences.

Life isn’t all about work. Tell us what a perfect weekend looks like to you.

Long walks with my best buddy -- my Tibetan Terrier dog, Bandit, connecting with friends and family, sailing or any other way of being on or near water and, last but not least, sitting behind a drum kit jamming with a band.

Jeans or suits?

Jeans for sure.

Feet flat on the floor or up on the desk?

Feet on the floor at a stand-up desk.

Favorite foods, drinks and hobbies or sports?

I love to cook complete meals on a grill year-round even in the middle of a snowy Boston winter. I love to sail and play the drums. I love to lead and motivate others, so I consider speaking and mentoring one of my favorite things to do.

If you could have dinner with anyone, alive or not, who would it be? What would you ask them?

Would they be buying? :)  

Seriously, I’m inspired by entrepreneurs and small businesses. I love to hear their stories, hear their passion and learn how they plan to take their idea or business to the next level.

Alec, how do people connect with you to find out more?

Entrepreneur * Speaker * Mentor * Investor

"America's Startup Success Expert"

Co-Founder, Constant Contact

Co-Founder, The Handy Cane

Limited Partner, G20 Ventures

Co-Founder, Point2Point Global



c: 617-834-3738



Alec Stern's Bio

CEO, Co-Founder, Point2Point Global

Alec has more than 25 years of experience as a founder investor and hyper-growth agent for companies across various industries. He is an innovator with extensive expertise in growing and scaling companies, startup and operational growth, go-to-market strategy, strategic partnerships and more.

As a primary member of Constant Contact's founding team Alec was one of the original 3 who started the company in an attic. Alec was with the company for 18 years from start-up, to IPO, to a $1.1 Billion-dollar acquisition. Alec has also been a co-founder or on the founding team of several other successful startups including VMark (IPO & acquisition), The Handy Cane, MOST Cardio and Point2Point Global amongst others.

Performing hundreds of keynote addresses Worldwide, Alec has become known as America’s Startup Success Expert for his popular sessions at conferences like Secret Knock, Powerteam International, City Summit and Habitude Warrior. In 2019 Alec is the Keynote speaker at three out of the top five “Inc. Magazine Must Attend Conferences for Startups and Entrepreneurs in 2019.” While on tour, Alec has shared the stage with the likes of Tom Bilyeu, Jack Canfield, Les Brown, Kevin Harrington and Mark Victor Hanson. Alec has also recently been featured on the covers of several magazines including “Small Business Trendsetters,” “Success Profiles” and “Business Innovators.”

Alec advises a variety of early stage companies and serves as a judge, mentor and advisor for nationally known startup accelerators and programs including TechStars, MassChallenge and the Stevie Awards and speaks at Universities including Harvard and MIT.

One of the Northeast's 20 most accomplished entrepreneurs, he is a limited partner in Boston-based G20 Ventures, which provides early traction capital for East Coast enterprise tech startups. Alec is also an angel investor in a number of rising startups in various industries.

Only a sideman when it comes to music, Alec is an accomplished drummer and has had the honor of sitting in with a number of musicians including Toby Keith’s house band in Vegas.

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