My favorite reading from the week of May 15

And the awards go to:

Rob Go of NextView Ventures for his post on considerations  for the ideal seed round composition; and also to Roger Ehrenberg of IA Ventures for his complementary piece on finding the right investors for the mission.  Startup guys raising their rounds now, read these two article pronto;

Fred Destin of Atlas as part of a really good angel panel, which among other things, talks about how the speed of AngelList threatens traditional (and slow) angel groups;

Fred Wilson of USV for his post on Sizing Option Pools in Connection with Financings;

From more than a week ago, but I just listened to (and can read here) a podcast by Mark Suster with Joel Spolsky of StackOverflow; and while we’re at it, his excellent article on building an entrepreneurial community (take note, Burlington…)

Delighted to read all articles about the terrific success of the LinkedIn IPO! Congrats CardMunchers! Here’s my favorite article, via Greg Gomer of BostInnovation.

Also happy to see this video interview and article about my latest investment, Saygent, here on TechCrunch. Congrats Guy and Mariya!

And last bit, which I’ll revisit when I continue my blog posts on MicroVCs, David Lerner’s interview with Jeff Clavier.

Enjoy!

Everything You Wanted to Know about Commingled Startup Funds…but were afraid to ask

We're talking EARLY stage

One of the smarter people I know, an engineer by training who has gone on to successfully manage $billions on both the “buy side” (i.e., institutional investors) and sell side, has asked me to write some posts aimed at educating people who want to invest in angel funds, rather than in individual investments. Seeing as we have more or less the same background (excepting the engineering degree), and I’ve done this exercise myself, I’m going to more or less reprise what I went about learning, skipping out all of the stuff which might be relevant to direct investing (e.g., term sheets, valuations, other legal stuff taken care of by the money managers.) Not sure when I’ll post all of these, but the topics I see myself covering are:

1)      How angel investments fit into both high net worth portfolios and institutional portfolios

2)      What is the right amount for an individual to be allocating to angel investing (See “How to Not Lose Your Shirt…”)

3)      Nomenclature (angel vs. super-angel vs microVC vs VC). (Just go to the link for Manu Kumar’s take on it.)

4)      Reasonable return expectations, holding periods, and the limitations of current research on the topic

5)      Nine questions to ask an early stage fund when interviewing them

6)      A review of what industry sectors are amenable to angel investing, under what conditions

7)      A review of my favorite 10 posts by other authors on angel investing strategy…even though I might disagree with them. (Funny, I’ve never seen anything written on angel fund investing that wasn’t by a fund principal.)

8)      Strategies for a beginning (or advanced) investor in  early stage funds, and how investments in incubators are different

9)      A list with links to all the larger super-angel and micro VC funds (hint—I will definitely need to crowdsource here for many of the funds on the West Coast).  Perhaps as I research this, I’ll try to get some of the bigger names to give us a quick podcast, although I’ve no idea yet how to set those up.

10)   Portfolio construction, diversification, etc.

I’ll also try to enlist a few pros from later stage funds to opine, edit, or if we really get our way, guest post.  In my previous lifetime as an LP of a two reasonable-sized foundations, I okayed some investments in fund-of-funds, and had a few consultants giving us their take on who is good or bad in the private equity world, with perhaps even some medium-sized VCs included. But there’s a lot of difference between VC land and angel world, as has been discussed ad nauseum in the blogosphere.

I’ve been totally neglecting this blog, but for good reason—I’ve written 6 checks to startups, made 5 other commitments, and I’ve given term sheets or am otherwise trying to get into 3 other deals…all since January. Plus invested in one fund and committed to another.  (Checks cashed: UpNext, Draker Labs, Noise Toys/Apptitude, Green Goose, Saygent, and Powerhouse Dynamics, with commitments to Crooster, Evertrue, MassiveDamage, and two stealth companies.)  That is just a frightening pace, basically double the rate of last year.  But given my (supposed) discipline backed up by a shrinking wallet, the investing pace will surely slow way, way down, as I mentioned in this earlier post.  Which leaves plenty of time to spend trying to help out the existing portfolio companies, should they want more attention. Since I’m guessing they all don’t want elderly back-seat drivers, that means plenty of time to write a course on commingled angel funds for my buddy.

But until then, here’s a link to Business Week’s online article, “SuperAngels Shake Up Venture Capital” which focuses on First Round Capital, along with WSJ’s review article last year, and a slightly more comprehensive survey by ChubbyBrain. They’re a bit dated, but they get you started. We’ll have similar background reading homework in each of the lessons.

“It’s X for Y”

“It’s X for Y”

Every angel has heard a pitch like the above. I recently saw a pitch on “LinkedIn for Pets”. Huh???  This means of comparison has become so cliché, and so laughable, that there’s a random startup generator to do this—click here and refresh a few times, you’ll see what I mean. (Thanks to Alex at Biff Labs, one of the many cool DogPatchLabs Cambridgecompanies, for the link.)

But it’s with good reason—people tend to, maybe even NEED to, compartmentalize ideas, and investors who only hear a quick elevator pitch need a memorable tag line in order to remember the concept. Localmind, one of my favorite phone apps and startups, is “Quora meets Foursquare.” I’ve got no complaints with short, sweet and clear. Synthesis is beautiful.

Or so I was reflecting when I came across this article by Don Ross of HealthTech Capital, talking about a change in the risk/reward in healthcare. (Quick sidelight—his partner, Anne DeGheest, did a wonderful podcast with Frank Peters on “mentor capital”.) One of Don’s theses, which I oversimplify but agree with, is that it is safer for angels to invest in simple, cross-sector areas in healthcare not requiring large capital or complicated approvals.  In other words, bring x to y.

How often is an advance nothing more than bringing something pedestrian from one sector and applying it to another? It works for everything from complicated math proofs, to securities lending (my old firm, eSecLending, changed an industry by bringing simple tricks from the fixed income world into the old, stodgy ways of custodial bank back offices,) to mixed martial arts, to healthcare. Or as Don Ross puts it, “health tech”.

There is no more important force in healthcare than IT, but the state of the art at least for patients and recordkeeping is appalling. Institutionally, there have been advances;  think how computers use brute force to help model drugs (note Google Ventures’involvement with AdiMab, where Google can add more value than just money), then compare how little progress has been made in standardizing consumer health records. How many readers can access their records online as easily as they can access their brokerage statements? According to my view, the best opportunities to both advance healthcare and make money as an investor are as prosaic, but necessary, as creating middleware to connect various medical records, reimbursement codes, and insurance companies.

And just as these new companies require bringing different skills to bear to solve old problems, I’m hoping that good opportunities exist to translate from one area to another. This, I think, is why I was invited to be a panelist at CareInnovators’ HealthTech 2011 conference on Friday May 13th in Boston. While I’ve invested in half a dozen healthcare companies (never without availing myself of some due diligence of my MD/researcher wife,) I’m basically a guy who never took science after junior year of high school.  Still, I recognize the similarities between, say, scaling systems and creating middleware between different vendors to be used in securities lending, versus the same technology opportunity in electronic health records. So I can see the value of assembling a few of us “healthcare outsiders” to compare sectors, wonder “what if…” and “why don’t…”

I’m really excited to be on the panel with Esther Dyson, who has gone from being the doyenne of tech gurus to an involved healthcare investor. (We both are investors in GreenGoose, which is pairing inexpensive sensors with rewards and games to create healthy behaviors. Mixing X with Y and Z.) Esther, I’m sure, has thought longer and harder about these confluences than I have, and I hope to learn a lot from her and the other mix of health & technology aficionados at the event .  It’s also interesting to see that the chairman of the conference is Charles Huang, who is at Spark Capital (known for its savvy bets in the confluence of tech, media, and entertainment sectors) to help explore and identify opportunities in the $2.6 trillion healthcare space that leverage technology in a meaningful way. When you have a translator who can speak two languages, well, good things are likely to result.

To me, the most exciting intersecting space is the use of mobile phone technologies to change healthcare. One entire panel is devoted to this topic (innovations in mobile health) at the HealthTech conference, with companies ranging from big data collector and analyzerGinger.io, to a consumer product like Runkeeper (which I’m using to track my jogs.)

There are many prominent angel and VC investors (like Don Dodge here and Mark Suster here) who posit that one needs deep domain knowledge to make money via startup investing. I’m betting the opposite—depth is great, but breadth may be even greater: what you need enough of a broad, “liberal arts”-style understanding so as to identify when one can transfer what’s proven useful in one area to apply it in another area. It doesn’t always make sense (like “rock opera”). But certain people can put together disparate and non-obvious combinations. Harry Markowitz won a Nobel Prize for being the first to bring mathematical and statistical rigor to portfolio management. Other genius can be found in combinations as simple as Reese’s Peanut Butter cups or as complex and subtle as fusion cuisine. So I welcome all the inventors, technologists and investors who are crossing over from healthcare to IT, or vice versa. I’m betting the next big wins are not new discoveries, but new combinations. Like X and Y.

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