Everybody travels a different road, and every day brings a new chance to change your particular route.
When Jon Carson was a sophomore at Babson College, he started a beer keg delivery business for fraternities in the Boston area and an entrepreneurial career was born. Other than brief stints at Boeing (sales), McKinsey & Co. (junior analyst), and two years at the Yale School of Management, he has always worked on his own ventures which—for the last 20 years—have always emphasized a social impact mission.
To date, Carson has started, built and sold four companies, the largest of which was Family Education Network, which became the largest K-12 website on the Internet ultimately acquired by Pearson. His most recent company was BiddingForGood, a $60m marketplace for charity auctions.
In 1999, Carson was profiled by e-School News as one of the 25 most influential people in education technology. In 2008, he was an initial inductee into the Babson College Alumni Entrepreneur Hall of Fame, and was a finalist for the Ernst & Young Entrepreneur Of The Year award (New England Region) the following year. In 2015, he was featured in Insights—Reflections From 101 Of Yale’s Most Successful Entrepreneurs.
Carson has served on the boards of the National School Boards Foundation, The National PTA, Net Impact, Trinity Boston Foundation and Americas Charities.
Where did the idea for CollegeVine come from?
The idea for CollegeVine grew out of the Harvard Innovation Lab, where I began mentoring three young college students looking for a way to take their “side job” to the next level. They had been public high school students who—despite having less-than-ideal college guidance experiences—somehow navigated the process and knew they could impart valuable information to others following in their footsteps.
Originally started as a way to give back while earning extra money for college expenses, the idea took off—the business growing so much so that they realized they were onto something big. CollegeVine (then known as Admissions Hero) was born.
I initially became involved as a mentor, but I have since then become CEO. As part of this group effort, my contribution/role in the process has been to force us to focus.
What does your typical day look like and how do you make it productive?
I try to get in as early as possible, as I do my best work/thinking earlier in the day. With my commute, that means a typical start between 7:30-7:45 a.m. I have a lot of routine meetings built into the schedule, so I keep things fresh by giving myself 10-minute breaks every 90 minutes or so. I’ll also take a mid-morning workout to get fired up when I return. Every Monday morning, I step back and re-list my priorities for the upcoming week
How do you bring ideas to life?
I have a very high bias for action, so I tend to gather information and determine key steps. If it’s a product idea, I will develop a functional spec for the idea.
What’s one trend that really excites you?
Since I think climate change is the #1 challenge facing humanity, it is the quickly growing consensus in the U.S. that it really isn’t a hoax, which is driving rapid adoption of renewables.
The education trend that excites me the most is the amount of innovation that is working to solve the problem of lack of guidance resources for high school kids.
What is one habit of yours that makes you more productive as an entrepreneur?
I exercise every day. Not only does it obviously keep me healthier overall, but it also fuels the creative process when I need a little boost in the day.
What was the worst job you ever had and what did you learn from it?
I was a minimum-wage messenger boy in NYC during a hot summer. That experience gave me a real appreciation for how hard and dull working-class labor could be.
If you were to start again, what would you do differently?
I feel blessed that I can look back and honestly answer that I wouldn’t do much differently. I tend to see every hardship—whether a minor bump in the road or a serious challenge—as helping to form who I am today. Everybody travels a different road, and every day brings a new chance to change your particular route.
As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?
I always seek context—the bigger picture in which to see a trend.
What is one strategy that has helped you grow your business? Please explain how.
Producing a high volume of high-quality blog content has gotten us good natural search rankings, which has helped build the business organically.
What is one failure you had as an entrepreneur, and how did you overcome it?
At my last company, an online charity auction service, we were not getting as many leads as we needed. Thinking about where do charity auction folks go, we figured out they knock on the doors of local merchants and sports teams to get items. That led to the development of an online item donation system for the merchants, where we co-owned the list of charities making the requests. It became our biggest lead channel by far.
What is one business idea that you’re willing to give away to our readers?
We own a second home in Vermont that is often unused, so my idea is a vacation property rental management service that’s a step above VRBO and Airbnb by providing ONE, easy stop for everything from the listings and coordination to the property management and post-rental clean-up. Essentially, one phone call and I am out of the second home rental business. Such a service would have a lot of interested folks who have money but no time.
What is the best $100 you recently spent? What and why?
Buying my kids books. Reading is food for the mind.
What software and web services do you use? What do you love about them?
It’s hard to argue with the convenience of Uber. I also love online billpay from my bank
What is the one book that you recommend our community should read and why?
Dark Money: The Hidden History of the Billionaires Behind the Rise of the Radical Right, by Jane Meyer. Every citizen needs to understand what is behind the corrupting influence of money in our democratic system. If we don’t get our arms around this, we will become a feudal society.
What people have influenced your thinking and might be of interest to others?
The staff of try to explain with facts and figures “the why” behind what is happening in the news, and the reporters from The Economist provide probably the best news magazine/website out there. To focus on a single influencer, I would have to choose President Barack Obama. Aside of being very analytical, he keeps steady in the storm, doesn’t get emotional in the heat of the battle, and is super pragmatic.
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