What should a veteran entrepreneur and investor with nearly 20 years of Valley experience do with his hard-won success?
Easy: give it away for free.
At least, that’s what Silicon Valley entrepreneur Kris Duggan is doing this year with his ‘100 conversations’ campaign. Duggan has committed to giving away many hours of his valuable time to provide less experienced founders with the sort of advice they’d normally pay dearly (or say goodbye to a healthy chunk of equity) for.
We’ll save probing questions about why more of Duggan’s fellow founders and investors aren’t champing at the bit to follow his lead. There’s enough to discuss about ‘100 conversations’ itself, and what it means for the founders with whom Duggan has already spoken.
‘100 conversations’ by the number
By Duggan’s rough count, he’d spoken with about 70 entrepreneurs with six weeks to go in the fourth quarter of 2018. Most of his interlocutors ran B2B firms targeting midmarket and Fortune 1000 companies with subscription-based service packages. Each conversation lasted 45 minutes, with no follow-up expected or required. No consideration changed hands, and Duggan has made clear he doesn’t want anything for his advice — save for a blog comment from each of his new friends.
Duggan is more qualified than your typical Valley founder to advise B2B entrepreneurs. He’s founded and exited two successfully venture-backed firms that raised about $100 million combined; advised blue-chip firms like Palantir Technologies and RelateIQ (now part of Salesforce); personally met reps from about 50 percent of the Fortune 1000; hired at least 1,000 sales professionals over 20 years; and hired at least 15 senior execs in the past 10.
What’s on your mind
If it’s of concern to a first-time founder, Duggan and at least one of his interlocutors have probably discussed it by now.
Duggan routinely advises founders to worry less about their pitch decks than about acquiring new customers, however they want to do that. He also counsels early-stage firms to avoid enterprise behemoths like IBM, whose approval bureaucracies move at glacial speed.
In recent conversations, Duggan has delivered company-specific advice about board and investor management; preparing for a Series A; and choosing the best-fit vertical for a particular solution.
A model for other entrepreneurs
Duggan isn’t the first to embark on this type of initiative. That it seems novel at all is less a validation of its disruptive potential than an indictment of the Valley’s “fail fast, but always look after number one” groupthink.
Still, ‘100 conversations’ should be an inspiration to any veteran entrepreneur or investor thinking seriously about giving back. Yes, there are plenty of worthy causes competing for their time and dollars, but self-directed projects like Duggan’s have real potential to stimulate serendipity — to forge interpersonal connections and catalyze ideas that might otherwise never have seen the light of day.
It’ll be exciting to see what comes of Duggan’s initiative in the months ahead, and what his entrepreneurial interlocutors do with the gift they’ve been given — if such a tableau were even possible to capture in toto.
For now, Duggan is turning his attention back to another pet project: a disruptive healthtech startup he’s been quietly championing these past months. Even the most magnanimous investors deserve star turns of their own, after all.
