Why Every Angel Should Beg to Mentor at an Accelerator

The Original Mentor

Most angels who volunteer as mentors cite noble reasons to do so: “paying it forward”, “giving back”, educating the next generation of entrepreneurs, and so on.  I love people who help others purely for altruistic reasons, and I hope such motives stay foremost in mentors’ minds.  The more favors you do, the more come back your way. At AngelBootCamp on 6/14 in Boston, there’s a great session with Katie Rae (TechStars, Project 11) , David Skok (Matrix), Roy Rodenstein (HackerAngels, just back from mentoring in Russia) and Sean Lindsay (Founder Mentors) entitled “Preaching Words of Wisdom: The Art of Mentoring”. Every panelist is a terrific, experienced mentor.

But besides creating good karma, there is one other big benefit of mentoring at an Accelerator: it’s SMART BUSINESS for an angel investor. One of my first pieces of advice on the opening panel at Angel Boot Camp in Boston this Tuesday will be for any angel, new or old, to affiliate themselves with MassChallenge or any of the other great accelerators now recruiting mentors.

#1 Inside Track to Great Investments in Accelerator’s Startup Cohort

Last year, I remember attending my first TechStars Demo Day and being part of a feeding frenzy of investors looking to be able to get into the oversubscribed round at one of the standout companies. A number of angels—Joe Caruso, Jean Hammond, Will Herman—were already invested, and another, Dharmesh Shah, announced his investment by tweeting (OK, “Marginizing”) live during the demo. All that social proof created a ton of well-deserved excitement, and for most, if you were late, you were out. Then and there I realized that there was a demonstrable financial benefit to getting in at the ground floor with the startups at the best incubators.  I was totally smitten with the event, but I also realized that a smooth, well-rehearsed 6 minute pitch was too seductive and too quick to prod for holes. (BTW—the good companies don’t always sell out fast: take the case of Occipital/Red Laser.) Being on the inside as a mentor means that you also can discern when to stay away from what might generally be acclaimed as a hot investment: I can promise you that you’ll never be able to do better due diligence on a startup or gain better insight into the founders than by working side-by-side with them during an accelerator program.

#2 Inside Track to Investments In Other Mentors’ Companies

I’m probably one of the more risk-averse angels, with a strong predilection for backing repeat entrepreneurs. And who better to back than fellow mentors, almost all of whom have started and ran successful startups prior to becoming angels and mentors. Last year at MassChallenge, I backed one of the startups (Pixability) run by an MC judge, and this year I plan to be backing a stealth startup being quietly put together by one of the TechStars mentors. That deal will never see the light of an angel group pitch, and it will be done totally with those angels who the founders know intimately.

#3: Community and Networking with other Mentors

I’m currently finishing up mentoring the Summer 2011 crop of companies at TechStars Boston. When you check out the list of mentors, you can tell that there are fantastic connections to be made. These connections aren’t necessarily mean just local—you might find Brad Feld or David Cohen in from Boulder, several prolific and experienced VCs checking in, or several of the NY mentors stopping by as well. Who better to help evaluate and discuss various investment issues than with your peers (or more often in my case, my superiors?) Just keep a lot of free meal slots available, and bring business cards. For instance, I ended up having dinner with Sean Lindsay (Viximo, Founder Mentors, etc.,) Fred Destin of Atlas Venture, and Harry Briggs from Balderton Capital, one of the leading VCs in Europe. Sean knows web engagement like the back of his hand, I found a slew of Wall St connections with Fred (yes, he used to be on the really Dark Side) and Harry brought a whole different global perspective on internet startups, in addition to stories about cricket, which we don’t normally hear around these parts. It was a great evening. Currently I’m looking to become more integrated into the Montreal startup community, so helping out as a mentor with Founder Fuel will give me an up-close view not just of the local startups, but also the regional angels and VCs. I can’t think of a better way than getting down and dirty with founders to find out from them who in the community is most knowledgeable and helpful to entrepreneurs.

#4 Education—YOURS

It’s assumed that mentors are the ones dispensing wisdom to mentees. But it’s a two-way street. While one-on-ones are the standard means of mentorship, accelerators also provide terrific opportunities to learn via participation in groups.  For instance, last month I sat in as a hot, VC-backed entrepreneur disrupting a big business gave a master class at an accelerator privately showing off the slide deck which he had just used to close a major B round of funding. The speaker fielded questions on what the objections were, what he handled well and where he might have lost points, gave tips on how he successfully managed old investors while bringing in new ones, etc. This was a fabulous, closed-door event where I was able to be the proverbial fly on the wall, just watching, all due to my involvement as a fellow mentor.

Equally important can be the small group meetings, where instead of one-on-ones, a handful of companies within a broad sector will meet. Last year I participated in the life science/healthtech group events, and was amazed at the amount I picked up from the companies. All of the entrepreneurs came with different perspectives into the industry, relevant resources such as lists of the best blogs, and insights as to what is coming down the pike in terms of new developments that hadn’t crossed my radar screen.

So, how to get involved?  Contact your local incubators—at this time last year there were more than 100 and the number (and quality) continues to grow. Mass Challenge is about to start, and there are several ways to get involved. Your local incubator probably has something similar.

Here’s an excerpt from a letter I sent out to Massachusetts angel groups looking for angels to volunteer at MassChallenge. (I’m coordinating some of the angel sessions.) With 125 Finalists participating over the next 3 months (or you also can follow them via MassChallenge on AngelList), there’s plenty of opportunities to get involved.

There are four basic ways for angels to participate in MassChallenge:

1. “Open Office Hours”
Entrepreneurs will sign up for sessions to talk about issues facing their companies.
This is a great way to get to know a lot of companies and entrepreneurs in a short period of time.
Contact:  ty@tydanco.com, (or just reply to this email) and we can start assigning time slots on a first-come, first-served basis.

2. Mentor
Angels who want to take a relationship with one or more companies more deeply can apply to be a mentor.
The Chief Mentorship Officer is Karl Buttner
Contact: mentor@masschallenge.org

3. Group Meeting/ Event
These will either be arranged either via a business theme or in a 
pitch setting.  Should the angel have some specific business expertise he would like to share e.g. cloud computing or financial technology, we would look to gather companies with an interest in this area to be led by the angel–perhaps a case study of a company you feel would be instructive, straight Q&A, etc.
Contact :  ty@tydanco.com,

4. Investor Pitch “Master Classes”
This would be a public event open to all companies – to see 3-5 companies pitch to angels and receive feedback. This was done last year by about 40 companies, and was considered one of the most valuable learning experiences of the program.
Contact:  ty@tydanco.com

Again, I’ll be at the Angel Boot Camp on June 14. If any of you want to get involved in MassChallenge, find me or John Harthorne, Akhil Nigam or Karl Buttner of MassChallenge.

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Next week I’ll write about my latest angel investment, EverTrue.  EverTrue is the TechStars company I have been mentoring, and they are raising a $1mm round. Most of that $1mm is already spoken before DemoDay, much of it by mentors. I don’t want to steal any of their fire, but Evertrue is a story of a classic lean startup blessed with brilliant execution. I’ve worked with them, talked to their customers, sat in on a sales call, and seen them successfully recruit talented developers in a tight market. The Evertrue story is due for a good long telling, and I’ll talk about it in the very near future.

9 Point Checklist Before Investing in an Angel (or VC) Fund


In the last post, I discussed how commingled funds, whether they be managed by micro-VCs, leading angels, or traditional venture capital funds, can be an important component in an early stage investor’s overall strategy. This is especially for those who otherwise can’t assemble a diversified portfolio. In this post, I’m going to talk about 9 areas I think are most relevant to look at before investing in a startup fund. They are:

1)     The Manager’s Background /Reputation

2)     Prior and Current Investments

3)     Focus:  Sector, Geography, Stage

4)     Philosophy: Size, Due Diligence, Participation

5)     “Edge”

6)     Co-Investors

7)     Decision Process

8)     Professionalism

9)     Rapport

This isn’t just academic: Except for my individual angel investments, everything I’ve got, from index funds at Vanguard to the more exotic, is managed by external managers.  I’ve invested in several angel funds before, and I’m looking at some different angel funds right now.

And there’s a ton of funds to look at.  As First Round Capital notes on its site:

And never in history have entrepreneurs had more choices for seed-stage funding. Early-stage capital has exploded, with new funds entering the ecosystem and late-stage funds playing earlier in the funding cycle.  Indeed – in the last few years we’ve seen strong seed-stage investment activity from funds like Felicis Ventures, FirstMark Capital,FlyBridge Capital Partners, Flywheel Ventures, Formative Ventures, Foundation Capital,Founders Collective, Founders Fund, Foundry Group, Floodgate Fund and fBFund And those are just some great funds that start with the letter F.

Much is written about how to select an institutional investment manager. There’s an entire industry of investor manager consultants (Frank Russell Company, Cambridge Associates, etc.) dedicated to the task. I’ve been on both sides of the fence on this one, having managed institutional fixed income for years, and having been on the investment committees of a few large foundations that chose managers.  While many of the principles carry through to selecting a commingled seed fund, the number one tool of all limited partners, i.e., starting searches by reviewing “top quartile” managers based on past investment returns, simply is unavailable in early stage managers.  Why? There is a paucity of good data, and it’s a relatively new field.

So what to do? Well, here’s my checklist. Your mileage may vary.

I.                 Background of the Manager

Just as there are the big kahunas of traditional Venture Capital (the Sequoias, Kleiner Perkins, etc.) and the old pros starting feisty newer firms (Union Square Ventures, Andreesen Horowitz), there is a known pecking order in Angel World. There are big kahunas (Ron Conway of SV Angels) and feisty upstarts (Dave McClure of 500 Startups) in angel land as well.  While having a big rep makes it easy to attract money for your fund as well as deal flow, in my mind that’s not the big thing. It’s experience, whether that experience comes only from investing in the sector for a long time, or even better, investing combined with a successful career as a founder/entrepreneur yourself.  Just as focus, flexibility, drive, work ethic and humility are important in a founder, they are just as important in a manager. And that background goes a long way towards understanding how that manager will be able to source quality deal flow, which is the life blood for an early stage manager.

Example: NextView Ventures, Boston MA

NextView is less than a year old, which might lead people to the wrong conclusion that the managers are just starting out. Each of three partners, Lee HowerDavid Beisel and Rob Go has a great background as entrepreneurs (LinkedIn, PayPal, Ebay, BzzAgent, Sombasa, About); and as VCs (Spark Capital, VenRock, Masthead, Point Judith). While they have bi-coastal connections and are beginning to gain a larger reputation (e.g., via Lee’s recent article in Fortune, Rob’s highly-regarded blog), they also are totally hooked into the regional scene (David founded and runs theWebInno events in Boston) As in virtually any endeavor, the team is paramount. Make sure your team is marked by having not just experience, but success.

II.              Prior and Current Investments

There is no better indication of what types of investments someone will make going forward than by dissecting past investments.  Study the portfolio: are these the types of investments you would want to have made yourself if you had had access to them?

Example: Felicis Ventures, Palo Alto, CA. Who wouldn’t want to invest with someone who has found places in such hot companies as Groupon, LinkedIn, Twitter, etc.  Scouring some of the other names in their portfolio, you can see that the manager, ex-Googler Aydin Senkut, also backs Tasty Labs (Joshua Schachter’s (of Del.icio.us fame) latest company), Room 77 (which wowed everyone at the Launch Conference), or RovioMobile (Angry Birds). These are overallocated, highly-sought companies that you can’t simply invest in by handing over a check; instead, you have to be hand-picked in advance.  If, on the other hand, you see companies you don’t know, and worse, know and dislike, ask the manager why they invested in them, and see if you like their logic.

An interesting flip side is to ask about a manager’s “anti-portfolio”, i.e., the good companies that they passed on.  There are plenty of good reasons to pass on a company, such as they don’t fit within your stated investment thesis or mandate, you didn’t buy the premise and didn’t see the pivot coming, etc. Fred Wilson of Union Square Ventures, perhaps the hottest VC firm today, wrote about why he passed on AirBnB; one of the longest-lived VC firms, Bessemer Ventures, talks about decades of greatest misses here. To me, though, I’m less interested in why they missed—just that they were able to be in a big time game and at least have a chance to see the winners.  If the biggest success someone has had access to was some mere 4x small win, don’t linger—you can find better.

III.           Focus: Sector, Geography, Stage

I’m not going to argue that anyone should be looking at, or limited to, any single sector.  As an angel, I dabble in several: it’s my money, it’s my responsibility.  But for outside managers, I want there to be a focus. Most early stage funds focus on some aspect of tech, for the same reasons most angels do—it’s capital efficient. But there is plenty of room for you, should you so desire, to think about hiring a manager to give you diversification on either a sector basis (e.g., healthtech), geography (especially important if, like me, you’re living outside of major entrepreneurial regions), and stage (which is why large pension plans typically dedicate slices of their PE allocation to both growth funds and LBO funds, representing different market characteristics and risk.) There has to be a hook that will allow the manager to specialize in something so that they know everything going on in that space.  A micro-VC can have multiple foci, but only if they have multiple principals. As far as stage goes—do they strive to be the first institutional money in, investing in lower valuations, managing relatively small amounts of money, and then handing off to later stage investors? (First Round Capital, profiled here.) Do they wait to invest at the A round, looking to invest $millions per company, through to B and beyond? (Most traditional big VC funds.) Or do they try to do the whole gamut, including tiny investments to $50 million slugs (Andreesen Horowitz; Yuri Milner of DST). Again, no necessarily right way, but there are some wrong ways. See if you buy their approach and reasoning.

Example: IA Ventures, New York, NY    Roger Ehrenberg, founder of IA Ventures, is an “Investor without Borders,” as likely to be looking for deals in Israel as he is in the U.S.  But while he has no geographic bounds, his firm focuses like a laser on “Big Data”; he’s earned a reputation as one of the must-see guys for companies in that arena. Just like it’s best to be own a small market, it far better to be the big fish in a carefully selected small pool than to be roaming all over the tech market.

IV.            Philosophy:  Size, Numbers, Due Diligence, Participation

At the core, you can divide angel funds, micro-VCs and VCs in a graph with two axes: the first is size of fund, and the second is number of investments. Let’s start with numbers: the larger the fund, the more the pressure seems to be to hang on for home runs. That’s a function of VC math, and the reason why many proclaim the “VC model is broken”: the more money the VC draws in, the larger their 2% carry, and they can live fat off the land, eschewing singles and doubles and holding out for home runs. Personally, I buy Basil Peters’ “Early Exits” strategy for most angel investments—there’s nothing wrong with a few doubles, and I probably would never consider a fund with more than $100mm dollars in it.  Small is good. However, being small doesn’t necessarily mean you can’t be swinging for the fences—Mike Maples Jr. of Floodgate bluntly states that Floodgate is going after “thunder lizards”, companies that will blast through their markets like Godzilla.  Higher risk, higher return. Something for everyone, so know your manager.

While size generally is a good indicator of philosophy, most telling is “numbers”—how many investments does a fund anticipate making? With that information, you can figure out two important ratios: average $s invested per company (which can tell you how many rounds are going to be invested along the way), and average # of companies per partner, which tells you how much attention each investment is going to receive.

The latter is the biggest style item, as it goes to the heart of a manager’s philosophy. There is a strong case to be made for index-style investing, which in startup land is often derided as “spray and pray”. While normally index investing is meant to give rock-bottom costs on efficient markets such as large cap  domestic equities where it is really difficult to justify active management, in inefficient markets like startups, the argument is two-fold: when one is investing so early, especially when before product-market fit is found, it’s a numbers game: it can be hard to judge between the top 20% of companies you see, and the hope of landing that 100x or even 1000x return company can justify a portfolio with literally hundreds of companies. (Revisit Sim Simeonov’s analysis on diversification.)

Examples: SV Angel/Yuri Milner’s Start Fund;  Dave McClure’s 500 Startups.  While the Ron Conway of SV Angel and Dave McClure of 500 Startups could not be more different, their investing styles are essentially alike: Invest broadly in areas you know, and then work your butt off for your companies, realizing that there is only so much of you to go around.  The Start Fund, which invests $150k in every Y-Combinator company at to-be-determined market rates, is the closest approximation right now we can find to a broad, high quality index fund. The first batch through was 40 companies at a time, and the next batch this summer is around 60. It’s provocative, but I think effectively investing across the board at an incubator as selective as Y-Combinator has many things going for it.  SV Angels also has managed other funds, but I’m not yet familiar with them other than this video.  500 Startups focuses on data, design, and distribution, in a quasi-accelerator fashion making use of terrific external mentors, as there is only so much McClure to spread around. When I asked him what his due diligence was, he glibly joked “writing the check”—in other words, he makes very quick decisions from the gut informed by his background at some seminal startups as well as manager of the Facebook Fund.

Who’s best to do this type of investing? Someone with massive dealflow and a lot of experience. I myself am waiting for the day that Naval and Nivi bring out their “Best of AngelList” Fund. Since they spend time interacting and interviewing all of the people who get to post to AngelList, I imagine they know a thing or two about spotting winners, and their deal flow would be global and second to none.

On the other side of the coin, there is the hand-crafted style of investment manager who makes few bets, but lavish portfolio companies with their time and attention. The idea here is that better coaching and selectivity leads to fewer write-offs leads to better ROIs.  Jeff Bussgang’s terrific book “Mastering the VC Game” makes the good point—calculate the number of companies being handled by each partner. How many boards can a person sit on effectively? Not many. But that’s the point—500 Startups and SV Angel don’t want board seats—they want quality, but they want breadth.

Example: Manu Kumar’s K9 Ventures, Palo Alto, CA  K9 only invests in local companies where they can add value.  How hands on? He actually funds companies at concept stage—for those of you who remember CardMunch, Manu was so integrally involved that he’s a co-founder of the company.  That’s the furthest thing from “spray and pray”—more like “invest in and dig in”. In that way, he’s more like a typical VC.

V.            Edge

There’s more early stage funds around then I can count. How can a firm differentiate themselves…not to their LPs, although that’s important, but to the startup companies they need to court? Reputation is important, as is focus, but what can give it an edge?

Example: Borealis Ventures, Hanover NH    Borealis is a small shop out in the boonies. While its three partners have the classic background I mentioned earlier (including stints as early employees at Yahoo, SoftDesk, etc.), Borealis’s unique edge is its intimate connection with Dartmouth College. Those ties, from involvement with the Dartmouth Entrepreneurial Network of alums to faculty/founders and the Tech Transfer Office, got it in to megahits like life science companies Adimab and Glycofi.  While there are hundreds of VCs circling Stanford, Borealis is the only game in town in Hanover, and that town houses Dartmouth College, its Business School, its Med School, its Engineering School, and a surprising amount of entrepreneurial mojo.

Example: Project 11, Cambridge MA.   OK, I know this firm is just getting started—I blogged about it as The Future of Seed Capital. Most of their investments stem from having a personal relationship. Their edge: their access (and role within) the TechStars Network. Katie is the director of TechStars Boston and sits in on the selection process in TechStars NY. Accordingly, she sees not just thousands of applications, but also is tight with the entrepreneurial plans of the TechStars Boston mentors—that’s leverage and reach! Additionally, Katie and her Project 11 partner Reed Sturtevant (they worked together before at Microsoft and at Eons) put on working sessions all over various incubators, and are co-located in the space at Dogpatch Labs Cambridge. Accordingly, they see hot companies like GreenGoose (originally out of Betaspring in Providence, RI), peerTransfer (MassChallenge, Boston, MA) in a far more intimate way than just attending a demo day, increasing the certainty of attracting winners and avoiding flashy but flawed startups.  That kind of intimate contact with promising, vetted companies at the pre-seed stage? That’s a real edge.

VI.          Co-investors

If “a man is known by a company he keeps”, it also holds true for VC firms of any stage. The best sign of respect for someone’s judgment is co-investing alongside. That’s the basis of Chris Farmer’s work on “Investor Rank”, which is akin to Google Page Rank. It’s a simple matter to cross-reference deals on CrunchBase to see who else is finding and valuing the same startups as the fund on which you’re doing your due diligence, and who’s in how early.

VII.         Decision Process

OK—I’ve been noticeably absent on talking about sidecar funds of angel groups. Why? Lots of reasons, but a major one is that angel groups act so slowly, and therefore second-time entrepreneurs often pass them by in favor of their existing connections. How slow? Well, it might take a few months to get from a selection meeting onto the next opening in a monthly meeting, and then again another 2 months to get due diligence together and actually execute. Who would you rather call on, someone who can give you a quick answer, or someone who takes 4 months from start to finish?  There are reasons beyond financial in order to invest in some angel groups’ funds—see my last post on that. But if more than one person is needed to pull the trigger (which generally I prefer), I want to know how the decision is made.

Example: CommonAngels III.

I’m in this fund for a few reasons, but mostly because of my experience sitting in on the group’s meetings. The membership is deeply talented and experienced in tech, and that network constitutes this fund’s advantage providing significant deal flow, vetting capability, and value add.  Large buy decisions for this fund occur in those deals for which there is substantial amount of investment and/or involvement by member angels. In addition, CA’s two professional managers of the fund run an active seed program, making seed investments in those deals which will close too quickly for the usual consideration by membership. The quickness with which they can execute these seed investments also gets the fund and the group in the door for further follow-ons.

VIII.        Professionalism

This goes without saying—you don’t want to entrust your funds to people who are cavalier about paperwork, reporting, etc.  You should get examples of the fund’s communications back to the LPs. Should you wish to back a new firm who otherwise passes the above tests with flying colors from their past lives, first make sure that they have this in place. Some entitities entrust their back-office matters to Village Ventures, which oversees the activities of many venture funds. That’s fine as well—but find out in advance how you’re going to receive tax accounting, statements, etc., from all of your big winnings. Remember, these are long term commitments—avoid long term headaches.

IX.             Rapport

I’m not talking about the personal rapport between you and someone within the Fund’s management. I have no idea who manages my small cap index fund at Vanguard, for example. But I’m talking about the rapport between the partners, and between the partners and their companies.  Again, this is going to be a long-term arrangement between you and the firm, and you don’t want the partners of that firm to be undergoing a company divorce.

Example: The Foundry Group, Boulder, CO  Consider what Brad Feld of the Foundry Group said in his post about Deeply Held Beliefs:   We will never add anyone to the team.  I have three partners (Seth LevineJason Mendelson, and Ryan McIntyre). We’ve worked together for a decade.  We’ve committed to each other to work together as partners “until we are done investing as VCs.”  We work extraordinarily well together and have no interest in ever introducing someone new into the mix.

I believe the best funds are those where everyone works together in the same office, and everyone is on the same page on any investment. Those of you who have worked in a distributed workplace where there are clashes of personalities with geographical lines know what I mean.

I especially like those teams who have worked together before in good times and bad, and who are equal partners. If you can visit the fund in person and see the interaction of people, all the better. My time at Year One Labs in Montreal is one reason why I hope to be involved backing their next vintage fund.

As for checking up on the relationships between Fund and their portfolio companies, that’s easy to do nowadays. Peruse their list of companies, figure out a connection to one of them via LinkedIn, and make a few calls.  Maybe peruse The Funded, although I wouldn’t take any single comment as truth. But it doesn’t take long to get a sense of the general drift.

OK, that’s my checklist of points to investigate. Below I’ve started a further list of some of the well-known firms I didn’t squeeze into the article above. A crowd-sourcing request—if you know of big names I’m leaving off (though let’s stick it to folks managing fund sizes below $250mm, please let me know in the comments area, and I’ll add them in.

Some other well-known names not mentioned above:

SoftTech VC

Lowercase Capital

Founder Collective

O’Reilly AlphaTech Ventures

Harrison Metal

Real Ventures

True Ventures

Who do you like that I’ve missed?

The Future of Seed Capital

I’ve seen the future of Seed Capital…and it’s Project 11.

Project 11: Mentor Capitalists

I spent an afternoon last week at DogPatch Labs in Cambridge, an incubator backed by Polaris Ventures. Like many incubators, there are a lot of promising startups there, like Play140 (which I’ve invested in); MassChallenge finalists Neuroscouting and Energesis Pharmaceuticals; TechStars Boston alumni like Social Sci, Localytics, etc.  But the most interesting people I talked with are the people behind Project 11, a seed capital fund run by Katie Rae and Reed Sturtevant. They are successful tech startup veterans, and Scott Kirsner did a good piece about their philosophy, and he writes about them better than I can. Full disclosure—I’m happy, like other angels such as Bill Warner, to commit to investing in Project 11’s first fund. (more…)

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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