My 5 Step Program to Regain My Investing Chops


A few years ago, I pretty much dropped out of everything but running my startup, BuysideFX. That’s now over ;^(    and now I’m itching to get back to investing in early stage companies. But I’m rusty. Real rusty. When I was running BuysideFX, I felt a duty to my investors not to be wasting braincycles on any other startups, and so now I feel out of it: I’m outside of the latest thinking, out of the good deal flow, out of touch in general. It’s like me trying to ride a luge sled again—intellectually, I know how, but my body, reflexes and muscle memory are so out of shape that I would crash hard if I tried to take off from the top. Not recommended.

So I’m taking some time to plot out my return to angeldom. I think it will take me a few months to get back into the swing of things, and here’s my workout schedule

I.   Catch up with my existing portfolio companies

Since I checked out 30 months ago, I’ve been a bad angel. Very little contact with my companies. Before I make new investments, I want to see how I can help improve the old ones. And of course, the best leads for great new investments (like Drizly from Brent Grinna at Evertrue, or Robin or CommandIQ from Phil Beauregard at Objective Logistics) come from entrepreneurs on the ground.

  • First, figure out who’s still around. My accounting is abysmal. That changes now. I’m setting up new gmail folders, transferring over from spreadsheets into cool cloud based angel accounting software from Seraf,
  • Reconnect with everyone to make sure I have the right contacts. I know at least 2 CEOs have been swapped out.
  • Enter everything into Mattermark to get a broad-brush idea of who’s hot and who’s not. (More on my very positive reactions to Mattermark in future blogs.)
  • And not to forget the ex-portfolio companies, like Crashlytics=>Twitter. I owe you forever, @wayne!

II.   Check out what’s been going on in my AngelList Syndicates

When AngelList syndicates came out, I knew that it was right for me. See my previous posts

So, now I actually have to figure out how they’ve done, and how syndicates have evolved.

  • I am entering each backed syndicate’s portfolio into Mattermark to get some portfolio level and individual company stats. Like Seraf, this wasn’t around in early 2012 when I started slowing down.
  • After trying to figure out the logic behind each underlying investment, I’m going to attempt to grade the syndicates. I’m going to cut back on some of them, as I’ll want to have access to that cash for my own direct investments. I’ll write up my favorites in a future post—sort of like a VC teardown.
  • Time to prune some of the syndicates. For instance, the syndicates which ballooned up far too big—with $mms dedicated to each deal, like Kevin Rose’s syndicate—I’ll just drop. The best deals probably won’t likely give up big tranches for nameless syndicates, and I’ll be cut down to next to no participation. (Request: @Nivi and @Naval, can all of the syndicate holdings be made public so we can study from the masters?)

III.   Get busy in Boston-Montreal corridor again.

  • With face time visiting companies at the co-working spaces, accelerators, etc. I’ve already re-engaged with the new TechStars Boston Fall2014 class, but know almost no one at MassChallenge, Founder Fuel and Tandem Launch in Montreal, Bolt, Blade, Harvard Innovation Center, MIT Media Lab, etc. That alone will take some time.
  • Re-establish connections with my angel buddies going to some of my favorite groups. Groups like Walnut, CommonAngels, LaunchPad, a few others.
  • Get reacquainted with VCs and Seed Funds. Every year Rob Go of NextView Ventures publishes his “Hitchhikers Guide” to the Boston Startup Scene. (Hey Rob, we’re waiting on the new one!) I’m a few editions out of date. First person I want to meet: Bill Aulet of MIT.
  • And while I’m getting reacquainted with the East Coast, I need to re-engage with my West Coast buddies as well. You know who you are.

IV. Start reading again. Need to improve the inbound flow of ideas, although I never really stopped reading some of the top bloggers. First book on my bedside table: Traction by Gabriel Weinberg. Then, I actually have to slow down and study Lean Analytics by Ben Yoskovitz and Alastair Croll.

V.  Paying it forward

  • Need to get the karma wagon back in gear. While I’m making contact again with the folks in #3, it’s time to start seeing how I can, to quote Sir Topham Hat, become a Really Useful Engine. Doing stuff like mentoring again—you always get back multiples of what you put in. And investors love 10x.
  • Creating and sharing content. In addition to highlighting some of the companies I know and getting them some exposure, (hi there, WooSports!) I want to take my new iMovie talents to start some interview series, hearing what entrepreneurs, service providers, angels and VCs are thinking about how to create more killer companies.
  • That means I’m going to be a lot more active on my blog and on Twitter. We’ll save the post-mortems on BuysideFX a few months so I can get a little perspective.

OK. less yakking, more hacking, I gotta get back to work.

But  I’m Baaaaaaaaaaack!

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