My 2014

January 3rd, 2014 by Miles Leave a reply »

It is a new year. And I’m turning over a new leaf.

It was bittersweet coming to the decision that it is time to step back from running Higher One full-time. I’ve spent ~14 years building the company and am passionate about the people, products and mission. That said, it is the right time for the company and for me. Starting mid-January I’m going to be part-time, Chairman of the Board, and involved in various initiatives.

So, what else will I be doing with my time?

First and foremost, I’m focused on a successful transition at Higher One. Next, on shifting gears and taking some time to relax, hang out and travel with my growing family.

There is a so much I want to learn and do in my life. When your head is down growing a business, there is less time for learning things that are not directly relevant. I plan to take this year to look around and explore the world (intellectually as well as physically).


100 Books: While not yet firm, I am intrigued by the idea of setting a goal to read 100 books in 2014. I made a list, piled up the ones I already own, and tallied pages; at last count I’m up to 30,898. Is that too many? Would it sound better if I told you some of these books I plan to skim rather than truly savor every word?

Book Pile for 100 Book Challenge

Some of the books I'm considering reading this year

Online Classes: I want to take at least one online class both for the content as well as understanding the process. I have my eye on one regarding statistical programming and another on genetic engineering. Any other ideas for me?


In addition to my work on the boards of Yale New Haven Hospital, SeeClickFix, Higher One, the Yale Humanist Community and advisory board of Yale Entrepreneurial Institute, I may join one or two more.

One board I’m excited to be joining is AltSchool. I’ve long wanted to be involved in starting a school and now I’m getting the chance. A friend from high school and college has embarked on creating a child-centered primary education company. We are already up and running in San Francisco and hope to expand to other cities, too. Check it out.

Possible Projects

Here are a few other projects that have been rattling around in my head. I’m not fully committed to any or all of these although definitely building excitement and would like to hear your feedback and thoughts.

Digital Fabrication: One technology trend that continues to build momentum is digital fabrication. The ability to design objects, transmit them digitally and manufacture them in small batches and on-demand is truly revolutionary. The impact on rapid prototyping and customization is profound not to mention what it means for distribution networks and just-in-time manufacturing. I want to learn more about the tools, players and techniques. Perhaps New Haven could use a Fab Lab or Fab Academy-type set up where people can get certified in these techniques? Could it be a partnership with Yale, Gateway CC and/or MakeHaven?

For Benefit Business: I’m intrigued by operations like St Vincent de Paul and Greyston Bakery who focus on job creation while running a revenue-generating enterprise. I’d like to help instigate a similar business for New Haven. (Do we have one already?) One option is to run a business plan contest. Another is to support an existing organization in expanding in this way.

Impossible Festival: I like to dream bigger. I think it would be fun to celebrate the declaration of intent to accomplish impossible things and then embrace the success of those that succeed. I think New Haven could have an annual gathering for those tackling the impossible writ large and small. A place one could come to announce the creation of synthetic life, the colonization of Mars, and the secret to losing those stubborn 10 pounds. Or how to learn to juggle. Perhaps this starts as part of Arts & Ideas Festival?

Art: It was very gratifying to see the Inside Out NHV project come to life. Now it is time for more art! We’ve got another mural project starting and I’m thinking of making a short movie with a friend. Maybe more?

Money in Politics: As I have learned more about our political system, I’m increasingly passionate about changing the role of money in politics. If for no other reason than to restore some of America’s trust in our government. One group that I have been getting involved with is Fund for the Republic and I look forward to finding other ways to contribute.

New Haven Startup Scene: I hope to continue to support the New Haven startup community. For example, I want to help Grid New Haven be successful, to encourage New Haven Tech Bits to keep going, and attend InnoHaven events whenever possible.

The Next Dream?: I’m sure there are other things we can dream up together so please drop me a line.

  • John Berkowitz

    Sounds boring and I feel you are starting to lack ambition. No but really this is all awesome and would be better titled ‘how to live the best year ever!’ My favorite is the impossible fest. If you kick that off i would love to participate in anyway that i could. your post motivated me..thanks!

  • Anonymous

    Awesome, John. Glad to hear it! Would love to have your help.