Breaking Glass Ceilings And Revolutionizing Businesses With Alec Stern


Significant successes are achieved by those who leave positive impacts with the right purpose to the right people. In this episode, Jen Du Plessis has Alec Stern to discuss his amazing breakthroughs in life. Alec is the Co-Founder of Constant Contact, a multi-million-dollar email marketing company that revolutionized the way small and medium-sized businesses are marketed. Becoming America’s Startup Success Expert was not a walk in the park for Alec, but his achievements amidst his cancer journey are proof that anyone can break their glass ceiling if they have the true will to do so. He shares the significance of working with the right people when innovating and offers his advice to those opting to transition their work during these challenging times.

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Breaking Glass Ceilings And Revolutionizing Businesses With Alec Stern

I have a wonderful guest with me, Mr. Alec Stern. I want to take this opportunity to tell you a little bit about his bio. He’s done a lot of things. Alec has more than 25 years of experience as a founder, investor, and hyper-growth agent for companies across various industries. As a primary member of Constant Contact’s founding team, Alec was one of the original three who started the company in an attic. Alec was with the company for eighteen years, from start-up to IPO, to the $1.1 billion acquisition of the company.

He performs hundreds of keynote addresses, which is where I met him. We’ve shared the stage together, hung out, and done other things together too. He’s known as America’s Startup Success Expert for his popular sessions at conferences like Secret Knock, CEO Space, City Summit, which I have been with him several times and many others. Alec is the keynote speaker at three out of the top five Inc. Magazine must-attend conferences for startups and entrepreneurs in 2019, which consisted of Secret Knock and some of those.

He appears as one of the Influence 100 Authority lists by Influence Magazine. He has been featured on the covers of other magazines such as Small Business Trendsetters, Success Profiles, Business Innovators, etc. In 2020, he won City Gala Visionary Award and the Habitude Warrior Conference Global Awesome Visionary Award.

He’s one of Northeast’s most accomplished entrepreneurs. He is a limited partner in Boston based G20 Ventures. He is also an Angel investor. One of the things I love about you is that you’re an accomplished drummer and that you’ve had the opportunity to play with Toby Keith’s house band in Vegas. There was an event that we were at together and you were going to be featured and I had a meeting, I couldn’t go and see. That’s when I first learned that you were a drummer and I said, “How fun is that?” I didn’t get a chance to see you but I’m sure I will.

I want to say thank you so much for taking the time with us to share your story. You’ve had lots of success. I know you in that realm of success and sharing fun things together like Craig’s watches that we bought. I see you as someone who’s such a giver to people and that’s the first thing I think of when I think of you, Alec. You’re humble about it as well. I appreciate that. I know that this may be uncomfortable, or maybe not, for me to ask you to tell us about your story. I want to know a little bit about the early years of Alec. Where were you brought up? What brought you to this point that is everything before the attic?

It was a great intro. I appreciate that. My mom was from Boston. My dad was from New York. They were living in Connecticut at the time. My mom came back up to Boston to have both my sister and me separately. I lived in Boston for five days and then moved to Connecticut where our house was and live there. At thirteen, we moved to New Jersey. I went to Syracuse for college and then I came to Boston after college. We have cousins up here that we visit. Since eight years old I said, “I’m going to live in Boston someday.” I follow through on that right out of college and broke away from everyone and came up here in Boston where I am to start my journey.

I have a lot of things that I had to overcome. From the age of 3 to about five and a half, I was in and out of children’s hospital up in Boston, even though we lived in Connecticut. I had a hip disease so I wasn’t allowed to walk. I had to be in a wheelchair, braces, and crutches. The way they treated Perthes disease back then was limiting any mobility for fear that it would do damage to the hips, which was a lack of blood flow for growth. They wanted you to be sedentary. I’m a little kid and I wasn’t like everyone else and I couldn’t play like everyone else. Anytime I tried to stand up, I got yelled at. It was one of the first things that I remember vividly and it was one of the first things in my life that I had to overcome and a challenge that I had to navigate because it wasn’t normal and I couldn’t be like everyone else.

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Especially as a child. I have grandkids and they are running everywhere at this age. There’s no way that you could have them sit. That must have been traumatic for you. When that happened, do you see that there’s something that still is an underlying issue as a result of that for you?

Physically, everything’s fine. Most people grow into what they need to with regard to the hips and blood flow and everything else and I was fortunate to be so. That went away and I became a normal kid physically. I don’t carry it with me mentally these days. It’s part of who I am, starting with some adversity young. I had some other things that kicked in along the way. It shaped me to not let it weigh on me. I handle the obstacles and things in life both with business and personal. There are an art and a science to how you address those. I talk about that often when I speak. Especially in business and if you’re a startup, you see obstacles daily and sometimes many times a day. It’s how you address those and breakthrough those, that’s what will make the difference from you succeeding or not.

At least you carry that. You went to school to go to college. What was your degree?

I was at Syracuse University and I have a degree in Business and Marketing. Growing up and stuff, my mom was an entrepreneur and she had her own small business. I often got pulled into to do things with her. She was an event planner and also did a lot with all the promotional items and customizing things for different events. I would get woken early on a Saturday morning as a teenager to get dressed up and put a bow tie on or go do something for her often. My dad was successful in intimate apparel, as a designer and led the designs for many companies but he wasn’t present. He traveled a lot. He wasn’t there much for us. They ultimately split when we’re younger.

I bet your mom taught you a strong work ethic.

They both did. In fact, my dad was definitely a workaholic. I didn’t want to go into business because I saw how hard he worked. Initially, I thought I’ll go to college and my major was Sociology and I did it for a semester and then I said, “This isn’t for me.” I switched to business school. Honestly, I’d seen it in a way that I didn’t want it, although I saw my mom and how she had the drive and then the success working as her own boss. When we were kids, if there’s something you wanted, you had to go work and make some money and get it yourself. I was an entrepreneur 8, 9, and 10, mowing lawns, shoveling driveways, car detailing, waxing, washing, whatever all odds and ends for the neighborhood. I did that all the way up when I went to college. I learned that if I want something, I’ve got to get it.

You have that drive in your DNA. It becomes part of your DNA. We’re right in the middle of the Coronavirus. We don’t know if we’re in the middle. We could be at the beginning. Our governor shut us all down. We are confined in Virginia. We don’t know what we’re going to do. That helps with the drive because I know a lot of people are at home saying, “What’s next for me? What’s happening?” This is a great time for you to be thinking about what you truly want in life. If you truly want it, you have to have the drive to go get it. You have to get off your tushie and get it.

STS 2 | Constant Contact
Use this opportunity to re-engage, reconnect, and build back some of those amazing relationships you have had in the past.


Also, on the business side, I’m talking to a lot of startups, hundreds of thousands a year. They’re not quite sure exactly what to do. This gives us an opportunity both personally and professionally. They talk about social and physical distancing. I call it long distancing because I’m checking back in with a lot of people in my life that were always special to me but as life goes on, we lose touch. I use this opportunity, personally, to re-engage, reconnect and build back some of those amazing relationships I’ve had in the past. I’m calling friends that don’t live near me that I wouldn’t see often.

On the business side, I’ve talked to people and everyone’s like, “What should I do? What should I focus on instead?” What I’d say to them is, “This is your opportunity to step back and look at things strategically.” We get caught up every day in the tactics. People are doing their day-to-day and you get on that hamster wheel of doing things tactically and try to build your business and have success, but this gives us a time to pause to say, “Let’s look at it strategically.” Several that I’ve been on the phone with and we’ve had video conferences and so forth, we’ve had breakthrough moments on stuff within their existing business for staying in the lane that they were in but maybe shifting over a little bit and finding an opportunity. That has been rewarding for me to assist and help them see that. People are taking time to look at things more strategically, getting back on their vision and how we’re going to get to that vision and not be caught up on what they’re doing day-to-day.

That’s important too. The Law of Polarity is that many people are stuck in fear versus freedom or scarcity versus success. If we look at everything that we’re experiencing in our businesses and say, “What is the polar opposite of this? How could I look at that strategically to accomplish it?” I know I’ve had to do that too. Both of us are speakers, we’re on the road all the time speaking all over the country and all over the world. We sat down and I said, “I get to do all the admin things. I have my assistants do some more admin things.” Until I realized, “There’s a shift that I need to be working on as an entrepreneur and those things are going to have to wait.” That shift is what is going to bring me out on the other side.

I have a friend and his pastor had said this, and I thought it was cool, “A boat doesn’t sink unless you let the things on the outside get in.” It’s good because that’s what can happen to us entrepreneurs, we let all these external things get in and that’s what sinks our boat. I’m not bailing things, I’m just not letting anything get in and I’m saying, “Where is my boat going to go right now?” It is going to go in a little different direction than I’m ready for. I love that you’re sharing that with people and having those breakthroughs come through as well. I know you had some other diversities and things that you had to overcome and breakthrough. Tell us about your experience with cancer.

I want to be a poster guy for PSA testing for men 50 and older, and if you had it in your family even younger. I have a great doctor and nurse practitioner team for many years and he went private into the home and she went to practice further away. I ended up switching over to someone that they had recommended. I was with that team for about five years. The test is maybe an indicator, maybe not and it never got run and I didn’t know to ask about it. I didn’t know much about needing that. Five years went by and we didn’t have any results for that.

I went back to the nurse practitioner who moved close to me again. In her normal workup, she ran the test and came back and it was above zero and she said, “We don’t have any history. We should get some biopsies done to be sure.” Seven out of twelve of the biopsies had cancer and two were 90% and they were up against the wall of the prostate. I went in for robotic surgery. I had a great attitude. I thought, “I’ll get through this and then I’ll be that poster guy for telling them about the PSA testing.” When I was going in for the surgery, I was high-fiving everyone and asking them to see the maintenance records for the robot. I was ready. It was go time, “Let’s get this thing done. A couple of weeks of in-home recovery and then I’ll be on my way.”

In the last cut of the surgery, a vessel burst and tucked up to where they couldn’t get to it robotically and it was too late to open me up. They rushed those two minutes that they had to deal with. I lost 100% of my blood, went into shock and cardiac arrest. They were pouring in more blood as they could to replace it. They were able to revive me and resuscitate me. The five-hour surgery turned into nine. I woke 22 hours later. They woke me out of an induced coma. It’s tricky to go from anesthesia to an induced coma in the middle of surgery and post-surgery.

There's opportunity abound for people to start a business simply by doing something that's out there and doing it better. Click To Tweet

I woke and I looked around and the first thing I thought was, “This is not routine.” There are doctors and nurses. I have all these tubes in my throat. They put me under for a couple more hours and then brought me out to take all the tubing out. I didn’t recall the conversations well for that. I was ambulanced to another part of the hospital where the care was needed for the situation. I was there for eight days. It wasn’t routine and it went south but someone up there was looking out for me. It wasn’t my time.

My perspective is that I don’t sweat anything, small and even large for the most part. I was always giving back. I was paying it forward with trying to help as many startups and entrepreneurs and raising the water level of that as much as I could. I took to heart having the opportunity to work with some great mentors and go to conferences, see amazing speakers, be motivated and said, “If I ever get asked, I will gladly accept.” That’s hundreds a year, which is great. For me, I don’t want to say a new lease on life because my life hasn’t changed much, but it’s given me a new perspective and that’s to do as much as I can for myself. I’ve got a lot of ideas. I’ve co-founded five companies.

You have Handy Cane. I was looking at that. That’s cool. I like that.

It’s a cane and grasper combined. Reacher-Grasper Cane is the company name. We’re working on innovative things in markets that haven’t been disrupted in 75 to 100 years and are $1 billion markets. We have an Innovation Think Tank where we spun out three and having some success in that. For me, I charge forward and give as much as I can and help where I can, and be there for others to succeed.

When did you have your cancer? Was this before you created Constant Contact or was this after?

Months ago.

I had no idea.

STS 2 | Constant Contact
The gap between someone with an idea and someone who is an innovator is that process of taking the idea that you came upon and sharing it with someone else.


I’m not hiding the story.

I was around you and I didn’t see it.

I didn’t want it to define me. I wasn’t going to let it bring me down.

You’re doing okay now?

Yes, knock on wood so far. Seventy percent chance it’s completely gone but I get tested every 3 to 6 months.

I’m thankful that you’re here with us. I want to ask you this last question about when you started Constant Contact. Take us back to this attic because a lot of people that are following this blog are people that perhaps have had this long corporate job and they’re saying, “I want to make this transition.” Coronavirus or not, they’re at this age where the Baby Boomers are getting older and where we’ve been in the careers for 30 and 40 years.

We’re saying, “What’s next? What else is out there for life?” They’re saying, “I don’t know if I can do that. I’m afraid to do that.” What would you say to those people? When you think back about how you were feeling, there’s some excitement, you’re like, “Can we do this?” There’s also the risk and the nerves. What advice can you give to people that are thinking about making a transition into becoming an entrepreneur that you feel would resonate with people?

It is how you address obstacles and breakthrough them that will make the difference between you succeeding or not. Click To Tweet

First, I want to say so everyone knows Constant Contact, that’s the one that always gets the billing. I’ve started eight companies, three acquisitions and two IPOs. I’ve been there and done that, and there are others that people wouldn’t necessarily know by name, “I’m a serial entrepreneur that likes cereal.” It’s my tagline. Honey Nut Cheerios for everyone who wants to know what the cereal is.

I was going to say, “What do you like?” I like those too and so do my grandkids.

Let’s step back from the question to say that on any day, week, month, we’re all experiencing products and services. We all say something like, “They could have done that better. That product could have worked better. I bet if it worked like this, it would be better.” We always are thinking about these things. Everyone has that, we all have ideas. I’ll ask a roomful of people, “How many of you think you’re an innovator?” Five percent of hands go up.

The only difference between someone with an idea and someone who is an innovator is if you take the idea that you came upon and you share that with someone else, or you run it by someone or you team up with someone and vetted a bit more and dig in, you’re moving toward being an innovator. Eighty-plus percent of the companies that are out there are not new, they’re taking an existing idea and executing on it better. There’s opportunity abound for people to start a business simply by doing something that’s out there and doing it better. The other 15% to 20% are new ideas like Constant Contact and Uber, Airbnb, Facebook and so on. You can do either.

There’s always a lot more to do if it’s something brand new because you’re having to create and promote a new category of a product and then ultimately your brand. There’s more to it. I would say to anyone that’s thinking about it, “You can’t go at anything in life with hesitation because if you do, you’re not going to succeed.” If you’re truly passionate about something that you want to create or take a stab and see if it can be done better then go for it, don’t hesitate. You don’t have to quit your job.

You may not have a choice, unfortunately, with what’s going on where you’ve maybe lost your job or furloughed or whatever it may be. Use this opportunity to work on that idea. Surround yourself with others that could maybe help you with the idea or others that could advise and mentor you with the idea. Most importantly, decide who it’s for and talk to them. I’m talking to the target market, potentials for products through Zoom and through other tools to converse and ask their thoughts about something.

When you do find your target market, the first thing you want to do is ask them what their goals and objectives. What’s not being met? What do you want more? They’ll give you the roadmap for what they’re looking for. If you can then share with them what you’re thinking of doing and it could map to helping them succeed, you’ll see that you have a winner. You might feel you do but don’t guess at it. Go have your target market and confirm that.

STS 2 | Constant Contact
Accomplishments are something to build on, not rest on.


I would say to some people and I hear it all the time, “I was that target market customer before. I know what they need because I was them.” It changes every day. I would say, get out of your own bubble and go talk to people. You need feedback from that target customer because it does evolve and change. There are many things like we’re seeing in the environment, society and all kinds of things that are hitting us that will change perspective. I would say, get out there and do that. I’m an idea guy. A week doesn’t go by that I don’t have a couple of ideas. Oftentimes, I want to run it by and vet it. That’s where you start and that’s where it will motivate you.

When we started Constant Contact, we heard many noes like, “No one’s going to use email as a marketing tool. No one can sell the small businesses out on Main Street without an army of salespeople.” I could give you all the noes. To me, no means not now. I look at it as a matter of time before we’ll come back around and potentially team up, work together, partner or possibly get investment or whatever it may be. I don’t hear no, I never did as growing up and I still don’t, which did cause little issues when my mother would say no many times but I wouldn’t hear it.

Get out there and work with others. Get that feedback and be driven by what your target customers are saying. When we saw our customers, we would ask them what they wanted. They wanted more customers. Drive people back in. Get new customers. They want revenue. We could provide a self-service, easy to use tool that they could use to achieve that, then they got wide-eyed when we started to show to our initial four customers that the others were testing it. We saw the promise in what we had and then it was a question of, “How do we scale it?”

Did one of you have the problem too? Where did it come up? Innovation is one thing. As you’re telling this whole story, I’m thinking about how many times something has come out. I see an ad. Our co-friend, Kevin Harrington, an ad comes and goes, “Why did I think of that?” Was this something that somebody had an idea, a challenge or a problem of their own that it came out? Do you find that happens with you on a regular basis? Are you taking some downtime every day to say, “What are some things that are around my house that I don’t like?” Where does that stem from? Is it natural? Do you have to think through it?

I don’t take downtime in that situation to meditate. I take downtime to innovate. I’m always looking for things. Some of the companies before Constant Contact that I was part of that we had an IPO in two acquisitions that worked in the small business space and we’re on the backend like eCommerce and payment merchant systems. I wanted to move on the frontend to do something on the revenue side to help them grow their business and help them gain new customers and so on.

The original founding guy, Randy, had a technology and he was working on some things that were circling that. We were introduced by a mutual friend who was a successful entrepreneur and also an investor. He said, “You guys should meet.” I’m good on market and getting things out the door and he was great at working through and figuring out how to work on those technically. We had a third person, Margaret, who is the software architect. They were working under the iceberg. We clicked and we were passionate about helping small businesses. We wanted to help them succeed.

Our original mission and vision was how do we level the playing field for small businesses against their big competitors? Amazon and others were firing up the marketing engine and they have enterprise tools, they had agencies and they had staff. Small businesses on Main Street didn’t have any of that. How do we level that playing field, create an easy to use self-service tool that all they had to worry about was, “What do I want to say or send? Who do I want to send it to and when?” We wanted to take care of everything else. That was the original premise. We were wide-eyed with a lot of many ideas to help small businesses. That was our one core thing that we started and is still the anchor of what Constant Contact is.

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It’s funny you say that because back then it was like, “How can we help small businesses?” Thank you for helping small businesses. It was helping small businesses and now we look at that and say, “Everybody emails. Everybody has a funnel. Everybody has that.” You guys were in the forefront of making that happen for the small business owner. Look how far it’s come. I’m amazed at what the opportunities are ahead of us that we don’t even know.

Thanks for creating that foundation for everybody. That’s wonderful. Thanks for sharing how that came together. One of the things I always say is, “Stop talking, take action and get results.” Take the time to think through things and be innovative. Want it bad enough. Share with your community, your mentors, your board of advisors. The most important thing is to take action because that’s where you’re going to get the results. Thank you so much for sharing that wonderful story. As we leave, do you have a quote or a mantra that you live by that you’d like to share with us?

I shared two. I shared, “No means not now.” The other one I live by that I say often and have for many years of my career is, “Accomplishments are something to build on, not rest on.” Every day, if we make a successful call to a potential partner, celebrate and I would say, “No, don’t,” make another call. They’re going to hear it through the phone, they’ll feel that energy. If you’re going to see someone, go see someone else right after that. If you have a successful follow-on call, you make another one and then at the end of the day, celebrate.

Alec, I want to say thank you so much from the bottom of my heart for giving me the time and to share this with my audience. I appreciate it. If you’re reading and you want to have Alec be a speaker at one of your events, you can give him a call and see if he has the time to put you in. I am honored and grateful for the opportunity for you to share your time with me.

I want to thank you because I know we’ve tried to schedule this for a while. Thank you to your audience.

We will catch you next time.

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About Alec Stern

STS 2 | Constant Contact

Alec has more than 25 years of experience as a founder, mentor, 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), Reacher Grasper Cane and MOST Cardio 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, CEO Space International, City Summit, Powerteam International 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 appears on the Influence 100 Authority List by Influence Magazine which recognizes his contribution to helping and advancing startups and entrepreneurs worldwide. He has also recently been featured on the covers of several other magazines including “Small Business Trendsetters,” “Success Profiles” and “Business Innovators.”  Alec was honored with the “2020 City Gala Visionary Award” and the “Habitude Warrior Conference Global Awesome Visionary Award” for all his accomplishments as an entrepreneur as well as speaking before thousands of entrepreneurs and startups each year.

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, The American Business Awards, The Stevie Awards and speaks at Universities including Harvard and MIT.

One of the Northeast’s 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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