My Favorite Angel Investor I Don’t Know

Apologies for having fallen off the blogging wagon in the last year. I’ve also slowed down the angel investing pace–a little bit because of valuations, but mostly because I’m running another startup, BuysideFX which takes up all my attention. (I’ll tell the story about how I decided to fund that later when we have something big to announce early next year.) Blogging, mentoring, investing, adding value has all dropped off the cliff, but offset by hopefully getting on another rocket ride as an entrepreneur.

But I’m back with a quickie post because I heard the best half hour of interviewing of an early-stage investor I’ve heard in a long-time: Jason Calacanis’s This Week In Startups interview with Chris Sacca of Lowercase Capital. There are actually two parts of the interview, which lasts a few interesting hours, but the money part comes at the end of Part II, when Chris talks about angels creating value first, not hype. This is the same theme he covered on his Foundation Interview with Kevin Rose before, which I also commented on in a blogpost a year ago. But it’s still a powerful theme of angels walking the walk, not just talking.

But now I have a story to tell. I invested in a startup that I found via AngelList, UpNext. Before I talked to the founder, Danny Moon, I had downloaded the great app, which I use every time I’m getting around in a major city, and immediately saw how useful and powerful his 3D mapping was. For due diligence, in addition to talking with Danny, I saw an interview on Untether.tv, and that sealed it for me.  There were a number of fine investors onboard–David Cohen and David Tisch from TechStars, Paul Sethi, Will Herman, etc. But Danny’s go-to guy in advising him how to negotiate his sale to Amazon was Chris Sacca.  I’ve never spoken to Chris, but I’ve got the distinct feeling that I owe him for helping Danny getting all of the shareholders such an excellent outcome.

There was almost no news on this transaction, and zero humble brags going around. Because it was a small round to start up, the absolute dollars weren’t something that was going to get Chris, who know manages metric tons of dollars, a meaningful difference in his life. But he dug in, helped, without fanfare. Pure value-add, giving back to an entrepreneur who hadn’t been in that position, from an experienced investor who has been in a lot of transactions.

Bill Walsh, former coach of the 49ers, said that if you sweat the details and work hard, “the score takes care of itself.” That’s why Chris Sacca is killing it with his investments, why smart entrepreneurs seek him out, and that’s what everyone of us in the startup community needs to do–just help out. Good karma results.

PS: Chris, if by any chance you read this, I’m down for a well, no swearing necessary.  And in the same vein as charity:water, check out this 2010 MassChallenge winner, Osmopure, for similar social impact. Tell Barack that an incredible use for American foreign aid is dropping 10,000 of these drinking straws wherever there are floods and other disasters screwing up water supplies.

Do like Chris Sacca: “Create Value Before Asking for Value Back”

I’m a full-time angel, plus I’m a procrastinator and an information consumer. So, I spend a LOT of time on the cruising the net, and find a lot of great content.  But a video from Foundation, Kevin Rose‘s new venture, was so insightful and full of entertaining stories that I had to stop in my tracks and immediately zip off this post saying just how great it is.  ”Create Value Before Asking for Value Back” is a theme brought up by superangel Chris Sacca around 15-16 minutes into his interview by Kevin, and it is at the heart of how Chris created his incredible and meteoric rise from nearly bankrupt, unemployed lawyer to Googler to one of the top superangels. Chris relays that “what really built a …business opportunity for me was just being helpful.”

Kevin too has his own story of how he got into Square, Jack Dorsey‘s incredibly hot follow-up to Twitter. Kevin loved the product, but the investment round was spoken for many times in advance–who wouldn’t want to back Jack? Nevertheless, as a fan, Kevin decided to “do a mitzvah” and help Square by producing a slick, professional HD video demonstrating how the product worked when the company had nothing of the sort available. While he was hoping perhaps to get noticed and have good karma come back to him, there were no strings attached to his efforts. Lo and behold, Jack then cleared some room for Kevin to invest in the seed round, and as we now know, those shares’ value has shot up a zillion-fold. Everybody wins. That is a classic example of how not just current angels, but anyone, can add value to a startup, shareholders, themselves and the world. When you look at Kevin’s track record, while Digg and TechTV made him famous, it’s those angel investments at Square, Twitter, Foursquare, Facebook, etc. that sets him apart from us mortal investors.  And the Square story is prima facie evidence that you can do very well by doing good.

This meme, which has a dark side corollary as well (“what goes around, comes around”), shows that it is just good business to be decent. It’s very apparent to me that the best deals that I see are the ones not that show up via the angel group circuit, but opportunities that come across my door specifically in return for past friendship or favors, be the source mentees, fellow investors, attorneys, or some other connection. The good karma reward is equally true for folks looking for jobs, investors, or customers (with the last case being proven by the success of Zappos.) Angels–when someone comes to you with a deal that doesn’t work for you, gain some karma points: even if you’re not going to write a check, try to at least respond to the emails, offer some constructive criticism, suggest a lead, or at the least leave the entrepreneur with a smile and encouragement.

Back to Foundat.io/n (Great show, why such pretentious spelling!? I blame del.icio.us): I haven’t seen the 6 other previous shows in the series, but I can’t wait. Kevin, like Jason Calacanis, Sequoia’s Mike Moritz, the brilliant Esther Dyson, and several successful hedge fund managers, started out covering tech or startups as a journalist or analyst well before becoming an investor. It turns out that the combination of networking, sector knowledge, and comparative analysis is pretty much an ideal background for angel investing. Add to this mix the ability to gracefully do favors for others, and you’ve got an ideal recipe for successful early stage investing. And when you, like Chris Sacca, can create value before asking for value back, it turns out you’re on the way to universal love, wealth, and the ability to do good–sounds like heaven to me. Pay it forward.

But first, check out that Foundat.io/n interview with Chris Sacca.

Four Weddings and a Funeral for an Angel Investor

Angel Investment commentary

Well, March has come in like a lion. Not only did we get 26” of snow two weeks ago in Burlington, but also I’ve been experiencing a blizzard of activity with my angel investments—4 good events, and 1 bad. Which is a great ratio, but then again, these are only midterms, and most final grades aren’t in.

So, what’s to celebrate? The best news came first: an exit on one of my investments.  The good news was accompanied by the first breaking of my Angel Investing New Year’s Resolutions: rather than wade through the reams of paper related to the sale, I just signed the consent agreements and am now waiting for the incoming wire.  If it doesn’t come in, I guess that means I should have continued to pledge to read all the fine print.

Next good news is an investment in NoiseToys, a startup out of Dogpatch Labs San Francisco. The current NoiseToys website displays an existing app, which has had a fair amount of success. However,  I’m more excited about a stealth app in beta now, called “Apptitude”, which allows people to share which apps they use—like merging social search with the App Store. I’ve always loved to just swap phones with people to see what gadgets they are using, and Apptitude allows this to be done among friends virtually rather than in-person. The app is clever and useful, and as always, I love the team. Here’s the AngelList writeup on NoiseToys. This is a West Coast company, and I can thank AngelList and the power of Skype video for making this investment both available and “diligenceable” for me.  Quick story on diligence: I saw that one of their investors was Charles Huang…who I assumed was the Charles Huang at Spark Capital in Boston. Charles and I talked for 10 minutes—we hadn’t met, but had 50 people in common on LinkedIn–when I finally asked him about what he liked about NoiseToys. Charles had no idea what I was talking about, and it turns out that the Charles Huang who invested is not Charles Huang of Spark, but rather the co-inventor of GuitarHero, out of the Bay Area.  So I got to meet two great guys out of one Huang number. (Sorry about that one.) So that much more of a bonus, regardless of what happens with NoiseToys. Just as with my investment in CardMunch, this is not a first time app for the founders—they’ve already honed their chops on previous products and are well-positioned to move the company forward on a ramen noodle budget.

Good news #3. Just last week, I visited the new Cambridge office of Incentive Targeting, which is doing a follow-on round. Incentive Targeting uses loyalty card information to more effectively target ads for grocery shoppers, and it does so in a Google AdWords-type way that makes it easier and more effective for the advertisers (the consumer packaged goods people like a yogurt manufacturer) to communicate and run promotions with grocery chains.  This was a pretty easy decision to follow-on: the round comes just on the heels of the announcement of a major new customer and another new pilot program, the combined extent of which will double their reach in terms of registered shoppers. Just as good, they have developed a novel (for grocery stores) new product along the lines of Groupon for groceries.  The two new client wins make it far less risky than at the time of investment last year when they had just one beta client, and I am delighted to follow on.  My visit also had had some serendipity to it: I had run into Rich Tarrant Jr. of MyWebGrocer at a Champlain College’s “Speaking from Experience” series. Besides running one of Vermont’s hottest internet companies, Rich is also a trustee at Champlain College, which has emerged as a key player in bringing together Vermont’s entrepreneurs. When Rich asked me what was up with Incentive Targeting, which is in the same Grocery/Internet/Ad space, it made me realize that I had been negligent on keeping abreast with the company. Which led to my meeting, and subsequent re-investment. And come to think about it, these two firms could work perfectly together—nudging me for some behind-the-scenes schmoozing to add value to my portfolio and to Vermont. Rich and Win Burke—call each other!

The fourth “wedding”—all in the space of 6 weeks, which is a bit scary—is an investment in Green Goose, a startup which recently rocked the house at Jason Calacanis’s Launch Conference. Green Goose is a combined hardware-software play (which always gives pause) combining inexpensive sensors you can put on anything from toothbrushes to barbells with a gaming layer to help promote good behaviors. Rather than describe it further, you can see links here and here, and read more about it here.  While I saw the live feed from Launch, this was a company where social proof was important. Bill Warner was the first backer, soon followed by Katie and Reed from Project 11, Jason Calacanis from OpenAngelForum and Launch, (not to mention Shervin Pishevar, Jay Levy, and other angels I don’t know)

I saw Boston investor Bill Warner last Wednesday, and when I mentioned my regret that I wasn’t able to be at the Launch Conference to see GreenGoose, Bill clued me in that the company was thinking about expanding the round. A few emails later, and now I’m in. I’m a little wary about the jumping onto the bandwagon, following the herd, being a lemming, what have you, but this is an extremely interesting company, and one that jives nicely with both my healthcare and mobile theses. With a CEO who can make a killer presentation. Expect lots of press on this firm as it expands.

And now for something completely different. I also had the not-pleasant task of saying no to a portfolio company who was looking to get another round. I’d already followed on once, albeit with a tiny commitment, before, but now was the time to give the bad news. Why the no? On the outset, the company is in a big space, has a potentially huge product, and is led by an experienced entrepreneur with a terrific advisory board. They had announced some pivots (which in itself is not bad—Incentive Targeting has changed their pricing model, so I’m not against those who change their minds), had missed some numbers (don’t we all—hard to remember any company which actually makes their initial projections,) but the killer problem was personnel: the company has lost several team members, and one of the replacements hired had already been found lacking.  Back to my 60% jockey, 40% horse theory, I was disappointed at a company which has a bankable CEO and advisory board seems unable to attract and retain the key technical co-founders or successors.  I’m still invested in the company, but I’m unwilling to put more into it.  While not yet a funeral, this is one of those times I’ve got buyer’s regret. There are a couple of other companies I now regret having put money into, but I’ll try to do my best to give counsel to all of those companies in the hope that they can turn it around. But the stark reality of startups is a high failure rate.  If and when (and there will certainly be a when for many) the firms end up DOA, I’ll do my best to figure it out and write about it.

I’m eager to learn more about the lessons of failures. I applaud those angels like Joe Caruso who list their loser investments as well as their winners. (And I’d happily take all of Joe’s losers if I could also get his winners.) Readers, I’d welcome any links to articles referring to “lessons learned” from bad startups, and especially bad angel investments. Know of any good blog entries? There must be several–let me know.

Ranking my Favorite Angel Groups

The last post on The Perfect Angel Group created an idealized composite group that unfortunately doesn’t exist. The post did beg the question of which is my favorite group, which I’ll answer here.  Quick disclaimer—I have visited less than half of the groups in New England, and none South of Boston.  So while this is a limited and regional list, I think it’s still instructive to look at a few of the groups in a little more depth.

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The Bronze Medal goes to Mass Medical Angels (“MA2”). There are several exemplary features of this group, not the least of which is that it is put on by thorough professionals at zero cost to participants. While zero dues can’t be sustainable in the long run, it is nonetheless a testament of the love and tireless volunteer work put in by its Board. The principals are Richard Anders (a successful serial entrepreneur), Carl Berke and Roger Kitterman, both VCs with the Innovation Fund at Partners HealthCare, and Pushwaz Virk from Dimagi.

What strikes me each time I attend MA2 is the incredible credentials and domain expertise of its members. As the name suggests, it focuses exclusively on medical investments, primarily in medical devices, and its members include department heads of some of the finest hospitals in the world, MD/PhDs, technologists, lawyers, engineers, regulatory experts, biz dev people, etc.  Every corner of the medical ecosystem is represented and represented well. Not only does this make for an exceptional screening committee, with the end benefit of uniformly solid, vetted deals making it through to the membership, but it reaches another level entirely on due diligence. While all angel investing is necessarily risky, I’m comfortable guessing that MA2, as it is known, will come up with a higher success rate than any other group I’ve met.

Let’s take Castlewood Surgical as an example of MA2′s due diligence. I invested in Castlewood (via North Country Angels) primarily due to my faith in its new CEO, Wolfgang Daum, who had done an exceptional job for investors at his previous job at Boston Heart Lab. Having tried to recruit Wolfgang to an attractive opportunity in Vermont, I was confident that wherever he chose to go would likely be a great story. So, I invested without deep due diligence. Fortunately, I was able to sit in later on DD with the group from MA2, and I was floored by the thoroughness of the effort. First, MA2 has a standing head of DD, Dave Tischler, whose presence adds for a consistency and professionalism to its process. Then, as at most groups, interested members join in on the discovery process. There have been  at least 3 due diligence meetings so far—the first with Castlewood’s founder (a physician/entrepreneur), another with the full management team, including the inventor of their device, and most recently without the company, but with the DD group interviewing with a heart surgeon from Cleveland Clinic, questioning him as a prospective device user acccompanied with an insider’s view of that corner of the surgical market, what hurdles of proof the new company had to pass for fellow surgeons to want to adopt it, the procedures at Cleveland Clinic and elsewhere to get a device through the purchasing and accounting departments, etc. Now THAT is due diligence.  And this is all after the original presentation made it through a knowledgeable crowd at both screening and group presentations, both of which were textbook examples of careful investing.

The downside is that such diligence takes time, and long decision times are anathema to entrepreneurs looking for funding. Given, however, the slow state of med devices getting through FDA approval, trial studies, etc., this approach is justified for the medtech sector. And as the best specialist in town, MA2 gets to look at a lot of good flow that doesn’t go to all of the tech-oriented groups.

The Silver Medal goes to Walnut Venture Associates out of Wellesley, MA. Like MA2, Walnut also specializes, but this time in IT sector, although that definition occasionally gets stretched.  Many of the members are MIT graduates (albeit from the ‘70s and ‘80s), and they are uniformly experienced investors. Being old pros, things are done a little more loosely. Members rotate chairing the meetings, and there exists a solid camaraderie and respect between members. Not unimportantly for me, meetings are held in the evenings on the campus at Babson College, one of the few angel groups that has evening hours. This leads to a more unhurried pace, and allows for a higher, more consistent turnout.  This in turn allows for a lot of shared history and reference. I’ve learned more sitting in on their meetings and talking with their members than at any angel group. While I came to angel investing with the background of 25 years of investing Other People’s Money in public securities, as well as an operational experience of running a successful startup from launch to exit, there was still a huge learning curve for me in angel investing. 18 months later,  I still learn from the Walnut members’ understanding of the nuances of angel investing.  In summary—interesting deals in capital efficient sectors, domain expertise, experienced professional angels, and a relaxed evening setting that allows for longer discussions with the presenting companies—what’s not to love? Well worth the long drive from Burlington.

And for the Gold Medal position…Open Angel Forum (“OAF”) Boston. Man, even their logo looks like a gold medal.  There have only been two meetings in Boston to date, and I haven’t pulled the trigger on a deal that I’ve seen there yet, but Jason Calacanis has come up with a different format that instantly makes this my favorite angel group. Like AngelList, OAF is an experiment in shortening the distance between entrepreneurs and angel investors. Both are global in outreach, but while AngelList is virtual, OAF is creating chapters in big financial or startup centers: Silicon Valley, San Francisco, LA, Seattle, New York, Boston, London, Colorado Springs, and Philadelphia, with management split between the founder, Jason Calacanis, and his associate Jason Krute. The two coordinate with local point people at each chapter.  In Boston, that means Bill Warner, the force behind the Unconference as well as bringing TechStars to Boston.  Mark Suster’s writeup is here for OAF LA–the format looks consistent across all of the chapters.

In my “Perfect Angel Group” post, I talked about my desire for several things which don’t even exist at OAF, and probably won’t happen in the short term.  There is no good recordkeeping, little advance notice if any on companies presenting, no archiving on the website, no due diligence process, and no formal affiliations with other groups. So how can it succeed?  It brings a stunning group of people together in the right way, and then gets out of the way.  While I’m going to guess that the average angel invests in perhaps just 2 deals a year, the average investor at OAF is far more promiscuous, and that’s a good thing…at least in angel investing. Meetings are in the evening, with plenty of food and drink, and unlike at other groups, the angels and all companies are together in the same room the whole time. No secret discussions, no closeting off of the entrepreneurs. Then, all of the angels introduce themselves, mentioning their most recent deals.  (That alone provided a lot of good conversation later on.) Presenters go for 5 minutes, with just 5 minutes for questioning, keeping the format moving, but that’s just the beginning. After the presentations are over, there is all the time in the world to move around in groups, getting the right people together. No one was forced to spend time (other than the 10 earlier minutes) on a deal that wasn’t for them, yet you had all the time you wanted to talk to the entrepreneur you wanted to, while still having the ability to corner a fellow angel for an off-the-record reality check.

From the entrepreneur’s point of view, it’s equally valuable. 20 super-qualified angels (well, some seed capital VCs sneak in), all able and willing to pull the trigger and make a decision, and all with broader connections to other angels should they want to help promote a company and raise a round.  While there is a danger that the locals will have already seen some of the presenters before, attention is paid to make sure that a few of the companies are essentially debuting for that crowd. So far, this has been ensured by having at least one of the companies come from out of town.  At OAF Boston #1, companies came from Montreal and DC in addition to MA, and at the 2nd meeting one presenting company came in from Ohio. Katie Rae (of Project 11 in Boston, and a MassChallenge mentor) now is selecting the companies to present, but I’m sure she benefits from Jason’s high visibility and his years of experience recruiting the companies presenting at TechCrunch50.

If there is a weakness in the OAF format, I don’t know it. Should an angel like a deal but require more time (or perhaps the ability to bring in some other domain experience), there’s nothing stopping them from making it happen.  And with most all of the crowd being professional investors (there were still a few with day jobs as entrepreneurs of their own companies), no lack of resources or knowledge that would keep them from a decision.

So, Open Angel Forum has positioned itself between the old (slower moving, less active) angel group model and the new internet speed dating (or bandwagon or “party round”) via social proof offered by AngelList. It still captures a physical meeting, which I believe is essential, but the flow and participants are qualified in such a way that the signal to noise ratio for all involved is incredibly high.  For angels, even if no company is right for you, it still is a focused and worthwhile time to get together with your peers. Without the silly allegations of “AngelGate”, if you’ve had to suffer through the coverage of that.

Congrats to the two Jasons for pulling off a better mousetrap. It is my giri to thank you. May you launch 1000 ships and 1000 companies via your new creation.

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