February 5, 2021
One of the richest learning resources of the Tuck School is our engaged alumni network. I yet again benefited from this a couple days ago, when I had the pleasure of interviewing David Grain T’89 for one of the keynote conversations at this week’s 16th Annual Tuck Private Equity and Venture Capital Conference. The founder and CEO of Grain Management, David shared a number of insights about the global communications industry. But he also shared a number of insights about leadership and about life more generally, two of which struck me as especially powerful for all of us on campus today.
One of David’s leadership and life insights was about the power of what he called “anti-fragility.” By this, he means the ability to grow stronger through adversity. As the pandemic was taking hold early in 2020, David assembled his firm and exhorted them to be ready to work harder, to dig deeper, and to be more creatively resilient than ever before. I was astounded by one measure of this success of anti-fragility: by year-end the firm had raised approximately $3.75 billion in new capital commitments – all on Zoom, whereas all previous fundraising had been done in person.
But this was far from David’s first success borne out of anti-fragility. When he founded Grain Management, raising his first fund of approximately $100 million took nearly two years in two phases. The first phase involved 185 one-on-one meetings across 10 months that yielded just three commitments. When two of those three commitments pulled out at the last minute, David had to restart in a phase two that ran nearly another year. And back when David was at Tuck, he landed his eventual summer internship and first post-graduation position only after being passed over by multiple other companies. Who hired him? The investment bank Drexel-Burnham Lambert, which collapsed into bankruptcy about seven months after he joined.
Yes, David has built a remarkably successful career. But time and again, he succeeded because of his ability to overcome setbacks – such as not getting the job offer or getting buffeted by world forces beyond his control.
The other striking insight that David shared was the power of planning. Toward the end of interview, a Dartmouth undergraduate asked a great question about what habits he should start cultivating now to build a fulfilling life. David’s immediate response was, “start planning.”
Every year, beginning around Thanksgiving and often extending to New Year’s Day, David writes down reflections on the year past and aspirations for the year to come. This work is organized around setting new goals – what does he hope to accomplish in the new year professionally, personally, spiritually – and then laying out new plans for achieving those goals. As he writes and rewrites, he distills the new goals down to a single page. But the plans for achieving these goals can be as detailed as needed, which many years he says has run to 50 pages or more.
“My goodness,” I thought to myself on camera, “what discipline: six structured weeks every year, dozens of pages of plans!” My Outlook calendar now has a new appointment on the evening of Thanksgiving 2021. “Begin David Grain Planning.”
Great leaders are great teachers. A highlight of my week was spending an hour learning from David about anti-fragility and about planning. If you didn’t get a chance to join him live, you can watch the conversation here.
Enjoy a safe and restful weekend.
Dartmouth has formed a high-level task force to plan for and manage possible disruptions related to the COVID-19 coronavirus outbreak, monitor federal and state recommendations, implement guidance, and communicate with our community.