TTM Dinners

Later tonight, at a small restaurant in Park Slope, Brooklyn, I am hosting a dinner of ten. Some are old personal friends, others are former colleagues, and a few are people I’ve recently met. All are accomplished in their respective fields. Tonight’s gathering is the fourth such dinner I’ve put together since the first in nearby Carroll Gardens last January.

The genesis of the dinner idea came from my belief that interesting things happen when you bring together a cross-section of people of different backgrounds and industries, from organizations large and small — and that being at that intersection is a great place to be. As I’ve put together the previous dinners I’ve been asked “Is there a theme?”, “Is there an industry focus?”, “Is this a dinner where investors can meet founders?” The answer to all of these questions is “no.” It’s just dinner and conversation.

Now nicknamed “TTM Dinners”, those attending tonight represent a cross-section of industry sectors including edtech, investment banking, fintech, film, consumer packaged goods, venture capital, and technology. At previous dinners, we’ve had leaders and founders from other industries such a real estate, adtech, academia, public sector, and philanthropy.

While my intent is to keep diverse the industry sectors of the attendees, the dinners have been weighted somewhat towards media, education, financial services, and the technology startup community (i.e., founders and VCs). That’s probably a reflection of both the industries in which I make a living as well as the commercial dynamics of New York City. What does concern me a bit is that the dinners have been sometimes too male, too white, too straight, too economically privileged, and perhaps too comfortable in a narrow center-left lane of political opinion. I have work to do to make the dinners authentically inclusive of different perspectives and backgrounds while also avoiding the appearance (or reality) of tokenism.

What is central to the dinners, and I think non-negotiable, is Brooklyn. I love my adopted borough of Brooklyn as much as I do my home state of Maine. Going back to my years at Deloitte and the work I led there with Silicon Valley Bank, NASDAQ, and Cooley to create the Digital Media Center, I have been excited about the idea of encouraging the business community to embrace Brooklyn as someplace where great ideas are incubated in a one-of-a-kind setting. I remember the excitement (and relief) I felt in March 2011 when I saw Deloitte colleagues, and then TMT industry leaders, Phil Asmundson and Craig Wigginton arrive to the first Deloitte event I organized in Brooklyn with Digital Dumbo. It’s incredible how the perception of Brooklyn as not just a place to do business, but also as a place where innovation happens and new companies emerge, has changed in seven years. There is perhaps no better place for a dinner like this.

Over the course of the three dinners to date a core of regulars have emerged, including the technologist and philanthropist Paul Walker, filmmaker Steve Shainberg, and media entrepreneur Gregg Schoenberg, who help me organize the dinners and, especially, curate the guest lists. Each has been incredibly helpful in providing me candid feedback and concrete ideas.

I am excited about tonight’s dinner and the amazing people with whom I’ll break bread in a few hours. The next dinner will likely be in April or May. If you’d like to join, please let me know by sending me an email at rob(at)