Onwards, to a world of painless meeting scheduling!

Why DCM Ventures is investing in x.ai

What’s the most you’ve ever done to schedule a meeting? Well for me, it took 43 e-mails, 2 months, and 20 apologies on each side. When I first joined DCM Ventures, I connected with an associate at another firm over e-mail, and we were all set for lunch in downtown Palo Alto on a Monday. On Sunday night, I get an e-mail from him, “Sorry, dude. Can we reschedule?” No problem. We go back and forth some more, and settle on Wednesday afternoon that week for coffee. My turn. It’s Tuesday afternoon, and now I have to reschedule — I’m in San Francisco all day as opposed to the South Bay (one of the many nuances of working the Bay Area). We decide to raincheck and reconvene once we both have a better grasp of our upcoming schedules. Two weeks go by, and I shoot him a note, “How are things looking? Want to do that lunch?” Blank rectangles as far as the eye can see on both of our calendars, so we put something down for lunch. The meeting lives in e-mail, but neither one of us had bothered to send a calendar invite. On the day that we’re scheduled to meet, I end up being in Menlo Park, but he’s in the San Francisco. Both of us had forgotten about the meeting since there was no invite. So there we were, back to square one. Living the dream. Fortunately, we did end up meeting. Coffee was great, getting there was a pain.

E-mail ping pong

I’ve gotten better at scheduling meetings, and I’m sure there’s a world of expert meeting schedulers that make my skills look amateur in comparison; however, at the end of the day we’re all just humans.

Venture capitalists like to tell people that our world is driven by relationships. Our relationship graphs drive everything in this business -market research, deal sourcing, due diligence, deal closing, and exit creation. We create and nurture those relationships through an endless slew of coffee chats, lunches, and phone calls. Needless to say, a large part of our day is spent scheduling and re-scheduling those aforementioned meetings. We cancel and raincheck. Then, we try and schedule again. Sometimes, if we’re lucky, we meet and promise to put something more substantial on the calendar for the future.

Scheduling meetings is a lot of work, and sometimes, I screw it up. I’m human after all.

Enter x.ai, which makes an Artificially Intelligent personal assistant who schedules meetings for you. All you have to do is cc’ Amy Ingram (or her brother Andrew), and she’ll take over the job of scheduling your meeting, start to finish. The company is founded by Dennis R. Mortensen, a serial entrepreneur who had counted that he had, in one year, set 1,019 meetings with 670 reschedules. In his mind, going through one’s inbox and scheduling meetings was a task best left for the machines.

November was a good month

In 2015, as a VC Associate, I did an average of 53 meetings per month based on the number of Outlook invites on my calendar. That’s around 630 meetings in 2015 (you win Dennis, clearly you’re meeting with more VCs than I am entrepreneurs). If I conservatively estimate that it took me on average 15 minutes to schedule each meeting, then that’s 9540 minutes or 159 hours. That’s a lot of time that I could have spent doing something else (like reading Medium posts about habits of highly successful people).

Are Dennis and I outliers because our jobs are more meeting-centric than others? Probably not. Every knowledge worker takes part in meetings, even if they’re not necessarily called meetings:
— Engineers have daily scrum meetings and code reviews
— Sales/BD folks have sales forecasting, pipeline reviews, and client meetings
— Finance/BizOps teams meet constantly to go over company metrics and quarterly reports
— Product Managers/Product Marketing Managers meet with all of the above folks constantly

Outside of the tech industry, almost every office in corporate America is filled with meeting rooms. From big board rooms to small phone conferencing booths, the offices of the world are filled with rooms designated for some form of meeting. If you are a knowledge worker, then you are either constantly pushing meetings or being pulled into them.

We are extremely excited to be partnering with x.ai and investing in their $23M Series B along with the amazing folks at Two Sigma Ventures, Work-Bench Ventures, IA Ventures, Firstmark Capital, Softbank Capital, Lerer Hippeau Ventures, Crunchfund, and Pritzker Group Venture Capital.

Here’s why:

We could not be more excited to start the journey towards democratizing personal assistants with the x.ai team.

If you want to bring Amy or Andrew into your life, you can join the waitlist here!

Thanks for taking the time to read!

-The DCM Ventures team

VC @DCM Ventures. Lifelong Warriors fan and my favorite type of dog is Shiba Inu. Will respond to most to e-mails sent to dcheng@dcm.com.

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