AngelList’s Big Four Benefits for Investors

Anyone who regularly reads this column knows I love AngelList. It’s the matchmaker service between promising startups and early stage investors which has revolutionized angel and maybe even VC investing.  There has been a slew of recent articles on AL, including good ones from Venture Hacks, Venture Beat, and BostInnovation.  But while there are a few guides on how to hack AngelList from a startup’s point of view, almost nothing exists for angels looking to get started. Which is where this blog post comes in.

I’ve put down a few the best strategies for angels to get the most out of AngelList—how to broaden your network, improve your deal flow, turbocharge your due diligence, and strengthen your existing angel investments.

I.                 You’ve Got to Be In It to Win It—Improving Your Deal Flow

Trust me on this, just open an account. It’s an unbelievable gift: there are no fees and no requirements for participation once you get in. Even if you only lurk on AL, being connected will make you a better investor—you’ll be more in tune with what is going on. But first you need to get on: you can register here.

Assuming that you are an accredited angel and you have participated in some deals (if not, you’re better off joining a local angel group to get started), the process is straightforward.  Our first hack: get 4 members to endorse you, and you go straight to the head of the line.  How do you find out who’s already on? The website is dead simple to explore, and you can search for angels by geography, name, activity level, followers, etc.

Setting up your Profile

Once you get accepted as a member, you’ll be asked to set up a profile including representative angel investments, the sectors and geography you’re interested in. How complete you do this is up to you; I haven’t noticed people listing their losers.  I prefer to list most of my angel investments over the past 2 years, as well as displaying my linkedin profile and website. Consider this how you want to introduce yourself, because it is all public.  Here’s my profile as an example.

Your Follows Determine the Quantity of Deals You See in Your Private Stream

Now the fun begins.  Just like Facebook or Twitter, what you see is determined by who you follow. Any activity done by an angel you follow is sent into your activity stream, and it’s easy to be overwhelmed by the thousands of investors and companies represented on the site, especially if you opt into the public site instead of setting up a personalized, filtered site.  If you were to follow me, you would get notified every time I follow a company, request an introduction, make an endorsement or comment, invest, etc.  So you don’t necessarily want to follow too broadly at first. Rather than get swept away by the full force of the firehose, you might wish to start by just following 25 or so semi-active angels. There are a number of ways you can decide which angels to follow: you could just import your list of contacts from LinkedIn, Facebook or Twitter, and AngelList can cross-reference to see who of those is on AngelList. Or you can look up the most followed investors here. Note that oftentimes the most respected VCs on the list with big followings might not necessarily be the best people to follow on AngelList. Why? It is unlikely Fred Wilson, Reid Hoffman or Mark Suster (all of whom are on AngelList) are going to tip their hand concerning which startups they are interested in.  Junior analyst VCs are just the opposite: they will take dozens of intros before even doing any hard diligence, as that’s their job–finding and then doing light scouting on hundreds of companies before bringing a handful of vetted leads up to their partners. Either way, I often find following either senior or beginning VCs creates too low a signal to noise ratio, so I concentrate mostly on active angels I respect. There are exceptions: some micro-VCs associated with incubators (e.g., Dave McClure) work AngelList hard to promote their companies…but you need to recognize that that is part of the brand strategy for their companies and their incubators.  One of my first investments via AngelList was CardMunch, in which I co-invested with Manu Kumar, Mitch Kapor, and Dave. And while I wrote about all the reasons I loved investing in CardMunch here, I never would have known about the opportunity if I hadn’t followed those investors.

Consider AngelList more like Twitter and less like Facebook: you can add people or drop them, there is no shame of “unfriending”.  For me, before I add someone, I check out what they show on their activity list to date.  If it is in areas I want to invest in or learn more about, great. If not…unfollow.  I may temporarily follow an investor whose portfolio I want to check out, but my follow list is fluid until I actually co-invest with someone, when I lock it in.

You’ll also be asked in your profile to define the areas in which you’ll want to see deals. You can define that geographically and/or by investment sector.  There are no limits other than your ability to process information on how many sectors to look at. However, if you choose “World” as your geographic area, there are literally no filters, and filters are your friend.  I have no interest in fashion, food, biotech, etc., and so I block those fields. But I want to see deals in mobile, location-based-services, fintech, and a few other areas of interest. So that’s what I include and what I see on my private stream.  The breadth or focus of anyone’s private stream can be discerned in their profile. I don’t know for sure, but I’ll guess the narrower the stream, the more disciplined and the more insightful the investor, although undoubtedly there are some hardworking people who are the exception that prove the rule.

II.               Turbocharging Your Due Diligence 

So, after seeing a few dozen deals (including archives of deals you wish you’d seen when they were live), you get the hang of AngelList.  But it may be a little scary being outside of the comfort of an angel group. The beauty of being in a group is less about gathering deal flow and more about learning via the insights of others. While AngelList may be decentralized, the ability to lean on others’ knowledge is at least as great. This can be done both within your current network and outside of it. Here’s how I approach due diligence on AngelList.

Before the Intro

Before I request an introduction to a company, I first check out what’s publicly available. Typically there is a slide deck, perhaps a video, links to a website, LinkedIn profiles of the key players, and a list of existing investors and advisors. I’ll click through everything that’s easily available, and more than half of the time I don’t go further, whether that be from some perceived flaw, too high a valuation demanded, or whatever. If things seem promising, I’ll then follow the company. In that way, I’ll stay abreast of all changes in status. (Don’t get carried away, however, if all of a sudden everyone is requesting an introduction.  If you follow the herd, you’ll most likely get trampled.) If I still like something a few hours later, I’ll request an introduction. Thomas Korte, ex-Googler and founder of the San Francisco-based incubator AngelPad, says that while he’s a big fan of his companies putting themselves up on AngelList, some of the companies have found themselves distracted by non-serious angel window-shoppers piling onto whatever companies are receiving the most introduction requests.  (There may be a solution for this coming up, as AngelList is beginning to post reviews of investors as well as companies.) If you see tons of other investors all requesting intros to the same company you want to talk to, take the opportunity at the introduction to give a little snippet about yourself to help persuade the company to take you seriously. But don’t sell yourself too hard—later on you’ll want to see if they gave as much effort to checking out you as you did to research them.

The Skype Call

Next comes a call to the CEO via Skype or some other video chat. (Phone is OK, but video is so much better.) Some angels have had success just riding on the coattails of others,  but I can’t imagine making an early stage investment without doing my own due diligence.

The interview is the time to read the CEO and find out more about the company. In other words, no different than at any other angel pitch.  And more often than not, companies flunk the interview. See “Why I Passed on Investing in a Hot Startup” and “5 Reasons an Angel Will Walk From Your Deal”. There’s nothing new to tell here.

There is, however,  one aspect of due diligence that is almost unique to AngelList: checking how thoroughly the companies do their due diligence on YOU. If they take your call without having done any preparation, that implies they are just looking for a check and are wasting their chance to see what other strengths the investor can bring.  But if they have taken the time to look at my list of portfolio companies, thought of what connections I might be able to bring, checked out my LinkedIn account, know where I’m from, etc., then I know that that the CEO is prepared and hungry.  A simple question like “How do you think I specifically might be able to add value to your company?” will often quickly tell you whether someone has taken the time to prepare for your interview.

Leaning on Others Inside Your Network

Assuming the CEO has passed muster, then it is time to compare notes with your fellow investors. When I don’t have specific domain expertise, which is true more often than not, I like to call in the reinforcements. MomentFeed, for instance, had some great traction, persuasive management, well-regarded investors and was involved in a sector I liked, but I was (and still am) lacking sufficient understanding of their approach to mobile marketing. I asked Jennifer Lum (ex-Quattro Wireless, ex-iAd, investor in Peekaboo Mobile) of Apricot Capital to check them out, and Momentfeed passed her more sophisticated review with flying colors. Both of us ended up investing.

Similarly, I recently saw a company with an intriguing product in data storage using a novel type of architecture. They have an excellent advisor, a tested prototype, and might be a big winner with a differentiated and cheaper product. In this case, however, my friend Wayne, the expert I asked to check it out, brought out a number of potential problems which I hadn’t thought of. While it’s still an open question if I go in, my decision undoubtedly will be more considered due to my friend’s involvement.

I’ve co-invested with both of the angel experts I mentioned above, and I really value their judgment. The funny thing is that I’m not in an angel group with either of them, and it would have been hard to get their input on a similar deal if it hadn’t been on AL. But as a result of the instant networking available with AngelList, where colleagues can get up to speed on a company almost instantly, due diligence can zip along at higher levels than usual.  One knock on AngelList is that many investors may get lazy and depend on someone else to do the due diligence, to the extent that no one does any. But I feel that’s more a critique of the investors involved rather than the software making it possible. 

Going Outside: Looking Up Investors and Advisors

Sometimes, I need to go outside of my network. While I went into ScriptPad, GreenGoose, Saygent and UpNext after talking to folks I knew who were involved, sometimes you need to go outside to a new source.  I invested in NoiseToys, for instance, after introducing myself to not one but to two Charles Huangs.

Checking in with investors is especially important in the 2nd round of a deal. AngelList will list not just current investors but also previous investors, which allows you to explore “signaling”, which can happen when an earlier investor chooses not to follow a round. If you see, for instance, Dharmesh Shah as a first round investor but not in the 2nd round, that doesn’t signal anything, as Dharmesh explicitly tells everyone that he’s a seed stage investor only and doesn’t follow in subsequent rounds.  However, I’ve found more than once a company that has great name investors in the early rounds who have chosen not to follow in subsequent rounds even though following is their normal modus operandi. How did I find this out? They told me when I contacted them. For these investors, their reputation is worth more than any single investment, so generally they’ll be straight up about their reasons. It may be that key management doesn’t work well together, that customers hate the product, or some other flaw that you should be aware of. AngelList makes it easier to find the skeletons in the closet due to the ease of referencing within the network.

Handicapping the Endorsers—How sincere is the praise?

It’s difficult to determine the difference between who is good vs. who is merely active, but there are hints. I’m a believer in the “Where there’s smoke there is fire”, and so generally those investors with large followings probably deserve them, and I will give them good weight, especially if they’ve had any recent successes. I tend to do an informal signal-to-noise ratio. If someone has 1000 followers, I first look at their investments to try to understand why. But when there are 2 people with 1000 followers, and you can determine through someone’s profile page that person A has made 50 recommendations and endorsements, and person B has only made 5, I give more weight to person B’s comments if only for scarcity value. The more you dig in and research, the better you understand where they are coming from. Brad Feld recently blogged “Why I Won’t Game AngelList.” While I think his policy of not following is perhaps too strong, I applaud the big picture. If you discover endorsements where the angel ISN’T putting his own money to work, discount appropriately.

III.              Expanding Your Own Network

The best leads come from your own portfolio companies. They are the folks on the ground closest to new technology, the customers, and their fellow startups. But a close second are co-investors from earlier deals. A particular beauty of AngelList is the ability to send private messages between those who follow each other. I first talked to Thomas Korte of AngelPad via private messaging on AngelList. He uses it often, and says that people tend to respond far quicker via AngelList than via normal emails or voicemail.

Follow Your Co-Investors so You Can Private Message

I’ve found this as well. Last week, I visited New York to see the current class at TechStars.  Before leaving home, I remembered that Localmind had been delighted to add Peter Bordes to the investor group via AngelList. Via the AngelList/Localmind connection, we were able to connect at TechStars (Peter is a TS mentor as well,) where we compared opinions on the new vintage of TS companies, shared ideas and leads, and got to know each other better. I absolutely know that I’ll want to seek out Peter’s opinion on media companies going forward, and hopefully I’ll be able to return the favor to him whenever I have something to add.

It used to be that the rule was to stick to your geographical area when investing…but now as my list of co-investors/scouts has branched out to San Francisco, New York, Toronto and the like, I know that my opportunities to invest profitably has only expanded along with my network. I make it a rule to follow the investors who I co-invest with via AngelList. While I might not know them now, following them and keeping track makes it much more likely we’ll meet up going forward.

IV.             Refer Your Own Deals

How can you not want your portfolio companies to attract investors with deep pockets, domain expertise, geographical diversity and broader connections? That’s the potential with AngelList.

I recently met 4 companies at MassChallenge who had put themselves up on AngelList, including founders of Fig, BrassMonkey, and Rentabilities, who all had success, and one other company that came up blank.  Some of their stories made the Boston Globe. As you might expect, the three companies that raised money all were very positive on their experience, whereas the unsuccessful company only received one lowball offer.

One difference is that the three successful companies all had already landed a strong lead angel and had refined their pitch through the process. And those backers endorsed them on AngelList–just as you should promote your own portfolio companies when they need new money. (Nivi of AngelList disagrees strongly that a champion is necessary, but I’ll take the traditional view. See Seed Stage Capital’s terrific article for more on this one.)  If you have found a company that has already landed you and perhaps others, think about sponsoring them on AngelList.  Being listed doesn’t mean that they necessarily have to take the meetings or commit to anything, and there are no fees to pay. The companies can and should use the process to pinpoint the investors that would be the best fit, avail themselves of the help that Nivi, Naval and the AngelList team can give in terms of strengthening their pitch. And you as an angel have just made it that much more likely that your company will succeed. Even if a fund raise is almost over, having the company list on AL means that they will establish more data points for future investors—and as Mark Suster says, smart VCs invest in lines and not dots. It’s a no-lose proposition to list: encourage your portfolio companies to do so, and even if it doesn’t bear immediate fruit, it may lay the groundwork for success in later rounds.

A Few Final Thoughts

AngelList’s biggest problem may be that it becomes a victim of its own success. It’s like the old Yogi Berra complaint, “No one goes to that restaurant any more, it’s too crowded.” Some of the site’s success has been due to the high level of curation to date. Inevitably, as the site’s popularity grows, it will have to scale via use of algorithms and crowd-sourcing, and undoubtedly average quality, which to date has been great, will suffer. But there’s no turning back now.  So, as is increasingly the case, we all have to learn how to process and boil down ever-increasing information.  At least AngelList makes it super-easy.

The basic game of investing is the same, but tactics keep changing.  AngelList is distributing information away from an exclusive “inside” crowd in much the same way that Bloomberg terminals revolutionized the institutional investing landscape by making the buy-side as informed as the sell-side. And that’s good for companies, and very good for folks like me in Vermont who don’t bump into startups every day the way you do in Palo Alto, Boston, Seattle, New York or Austin.  I’m not sure where AngelList goes, but it continues to add value in different ways—not just the end of a seed round, but in B rounds, as a way to test pitches, etc.  What I do know is that early stage investors who don’t spend time and master it don’t know what they are missing. I don’t know if my investment returns will go up because I study AngelList, but I know the odds of success have improved and I am a smarter investor.

Have you used it? Let me know what you think.

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?

Why I’m Investing in CardMunch

This post will replay some of my thought process prior to investing in CardMunch. I’ll attempt to discuss not just the standard checklist features (“Is beta built?” “How much revenue?”) but also the intangibles that led me to jump in.

At startup presentations, I initially have interest in probably 1 in 4 deals, but in most cases any infatuation goes away after a little due diligence on the team and market. In the end, the actual hit ratio ends up much lower—in 2010, I’ve invested in 12 deals out of 237 seen, i.e., 5% of the deals I’ve seen, and I’m only counting the ones that came to me via a filter, such as angel group presentations, incubator demo days, and recommendations from angel friends. So, 95% of the time, fear/apathy/conservatism trumps excitement/greed for me. (more…)

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