Graeme Thickins on Tech

Reflections & analysis about innovation, technology, startups, investing, healthcare, and more .... with a focus on Minnesota, Land of 10,000 Lakes. Blogging continuously since 2005.

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New Face of Venture Investing: the ‘Small’ Guys

The world of venture investing has changed….in case you haven’t noticed. Yes indeed, "small" is very much in — as in smaller investments — especially for startups having anything to do with the Internet. [And that would include most everything to do with IT and software today, not to speak of consumer services.]  The reason is simply that startups don’t require as much capital in this age of…whatever you want to call it: "Web 2.0" or "the Internet as platform."

A great article in Saturday’s Wall Street Journal drove that point home again: VC’s New Math: Does Less = More?  The main subject of the article was Peter Thiel, the former CEO of PayPal, who now runs a small VC firm that’s become the talk of the Valley.  It invests "sometimes just a few hundred thousand dollars" in its deals, says the article, which also quotes him as saying that the venture-capital world "definitely needs to be shaken up." Thiel and his fellow founders and execs from his PayPal days have built quite a record of investing, including an early stake in Facebook. Last year, the NY Times also published an excellent article about Thiel and his "mafia": It Pays to Have Pals in Silicon Valley.

Newfaceofvc_2

But Peter Thiel and his gang are hardly the only ones leveraging this new model. I present here six more that have it figured out pretty well, too, with most already reaping rewards, as firms they have backed have either been acquired or achieved big paper valuations. [There are surely other "new VCs" I could feature here, but these six are the ones I know best, from reading and commenting on their blogs, hearing them speak at conferences, or actually meeting some of them in person.] Note that most of these guys began by investing their own money as angels, which they gained from successful careers as tech entrepreneurs or traditional VCs, but all those that did start that way have morphed into the new breed VC, because they’re now investing other people’s money as well. That is, they’ve raised traditional VC funds, but tend to focus those funds on smaller, Internet/Web 2.0 type investments. (Thiel’s new career even goes beyond this, however, as he also manages a hedge fund, as noted in the Journal article.)

Breeding Winners
Who are the others pictured above? Josh Kopelman of First Round Capital is based in the most unlikely of places, suburban Philadelphia, but calls himself the "Redeye VC" (which is the name of his blog) because he’s flying to the Valley so often. His entrepreneurial background includes Half.com, which was acquired by Ebay. Josh was the subject of a feature just published by Fortune on people to keep an eye on in 2008, as the traditional media continues to discover these guys we know, because it’s realizing how much wealth they’re helping create behind the scenes. Josh’s portfolio will impress you.

Fred Wilson is the reigning godfather of Web 2.0 investors from his perch in NYC at Union Square Ventures. And that’s largely on the strength of his blogging — he blogs on his firm’s site, and at his personal blog, AVC. Check out his firm’s portfolio of Internet investments. Fred is hands-down the most prolific of the VC bloggers (with more readers than only Guy Kawasaki). I actually don’t know how he has time for much else with all the blogging and Twittering he does. (He’s an investor in Twitter.) But then, he’ll tell you he actually learns about many of his deals through his blogging. He considers it an unfair advantage, and has caused many other VCs to catch on to the benefits of writing in the blogosphere. For more on Fred, who’s actually a pretty private and low-profile guy (for example, he doesn’t show up at too many conferences), see this profile that appeared on a Wired blog earlier this year. 

Jeff Clavier is one of only two of this group based in the Valley — Palo Alto in this case. [Note that two of the others are in SF, but three are elsewhere.] Jeff has an extremely interesting and eclectic background, starting in France, where he did an IT startup, acquired by Reuters, where he later served as a corporate VC. There, he managed early investments in such firms as Yahoo! and Verisign. He later migrated to the Valley and become one of the early investors in Web 2.0. His blog, Software Only, was an early and influential voice in this new world of venture capital. Just a few months ago, Jeff announced on his blog his new $12 million seed fund.

Brad Feld is based in Boulder, CO, and is one of five partners in The Foundry Group. He’s a prolific blogger, at both Feld Thoughts and Ask the VC. The latter is one of the best resources I know of for enterpreneurs seeking advice online. Brad is an amazing, high energy guy. A marathoner and an inveterate entrepreneur with a masters from MIT, he’s lived the entrepreneur’s life as founder of a
software firm that was acquired by AmeriData Technologies (later acquired by GE Capital), where he served as CTO. Brad was a driving force behind the launch this past summer of the TechStars competition in Boulder, and his firm has already funded some of the winners.

Dave Hornik is a very well known member of this new breed of VC, for two reasons — he was an early player, and he’s based in the Valley. His firm, from its cool digs on Sand Hill Road in Menlo Park, invests in more than just Internet services, however. Some of the names you would know in its Internet portfolio are Six Apart, Technorati, Evite (acquired), Shopping.com/Epinions (acquired), Postini (acquired), and Tumbleweed. Dave’s VentureBlog was one of the earliest VC blogs, which certainly contributed to his popularity, though he’s posting much less frequently there of late.

Aydin Senkut, by contrast, is probably the newest and least known of the group. An early Google manager, he left in 2005 and now runs Felicis Ventures in SF. You say you’ve never heard of it?  Well, check out his portfolio. He was one of the subjects of a NY Times article a few days ago entitled A Post-Google Fraternity of Investors. While the ex-Googlers now investing in startups (most as angels, some as VCs) are not as tight-knit a group as the ex-PayPal founders and execs, there are potentially many more of them.

What do you think of this new breed of venture investor?  Are they really changing the game, or are they simply more of the same-old Vulture Capitalists, just dressed in tee-shirts and jeans?  🙂  And, how early do you think entrepreneurs with new ideas should approach these guys?  Will you?

UPDATE (1/7/08): For more on this trend in venture capital, no one says it better than Chris Shipley, Executive Producer of the DEMO Conferences. Check this out, from a series of recent DEMOblog posts on 2008 predictions: Venture Capital Feels a Pinch[And, by the way, look for me at DEMO ’08 in Palm Desert, CA, January 28-30.]

Kayak Eats Sidestep – Thanks, ‘Santa Sequoia’

Some of you may recall I’ve posted a lot in the past on the topic of "Travel 2.0."  Here are my twelve posts, which must total something like 20,000 words. I still get a fair amount of traffic to those, even though most are at least a year old.  The subject of many of them was one travel company in particular…a Minnesota startup.  More on that in a bit.

Back to the main impetus for this post today: a big announcement that many of you may have missed, since it occurred over a holiday weekend — when, hopefully, most you are not online. [Sadly, your trusty blogmeister here has to be…one of the occupational hazards of being a blogger!]  Here’s the latest big Travel 2.0 announcement: Kayak.com Secures $196M in Financing Round.

Kayakeatssidestep_2 That’s right — close to two hundred big ones, enabling Kayak to acquire ("merge with") fellow travel metasearch site Sidestep. Sequoia Capital led the round, which included many other existing investors in both firms, and VC superstar Mike Moritz gets a board seat. This is the largest amount of dough in one Travel 2.0 deal that I can ever remember seeing.  I thought ITA Software raising $100M in VC last year was a big deal, but this dwarfs that, all in one big, fat round.  [Interestingly, that ITA deal shares one big investor with the Kayak deal: yes, our Santa Claus friend, Sequoia. Do you get the idea they like Travel 2.0?]

It’s a bold move to elevate the combined entity into what the release labels as one the five top travel brands (by which they mean the amount of Internet traffic).  Moritz is quoted in the release as saying the deal "reshapes the largest sector in online commerce."  He’s right about the size — I’ve seen numbers saying it’s approaching $100 billion. And I was actually quite surprised to hear experts at last year’s "Travel 2.0 conference" call travel, overall, the world’s single largest industry.  So, this is big stuff — I think we have that established now…  🙂

What was the Minnesota startup I mentioned I was writing about last year?  That would be Flyspy.com, a third-generation airfare search engine — still in alpha as we speak (but be patient). Flyspylogo2_2
Keep you eyes open for some news from this startup. I’ve continued to stay in touch with the founder, Rob Metcalf.  No, it’s not about huge amounts of money — the business doesn’t require that now.  But it’s a significant development for a startup that’s been working on its idea for close to five years now. Let’s just say Flyspy is having a very nice Christmas.  Cheers to you. Rob!  (More on this later.)

UPDATE (12/28/07): You say you hunger for more data on this deal? And you just love charts? Boy, do I have a deal for you. You’ll get your fill here: Compete.com’s Analysis of Kayak and Sidestep Merger.

Bootstrapping: Why Do Entrepreneurs Do It, and How?

The term “bootstrapping” has applicability to many things, according to Wikipedia. But, at least in business, it means “to start a business without external help (capital).” You can read more about that specific meaning, also called  “bootstrap funding,” on this Wikipedia page — lots of helpful information there.

bootstrappingBut what got me thinking about bootstrapping was a few things: first, I posted recently on the topic Raising Startup Money? Here’s 20 Ways — and a large number of those ways qualify as bootstrapping. Yes, the money you save by bootstrapping is real money! But, after that, I saw a blog post by Jeff Cornwall, who heads the entrepreneurial studies program at Belmont University (and used to teach here in the Twin Cities at the University of St. Thomas). In his blog post, which was called “Why Do We Bootstrap?”, he said he’d just begun working on a new book on this topic. The interesting thing Jeff has found in his work is that entrepreneurs bootstrap for a wide variety of reasons, and only some of them relate to necessity.

The other reasons I find the topic of bootstrapping interesting are (1) I’ve practiced this religion myself for many years, and (2) I think there’s especially a need here in Minnesota for startups to get more educated on this topic. Why?  Because, try as we might, startup venture funding is never going to flow as freely here as it does in Silicon Valley, or Boston, or Austin, or you name it. Entrepreneurs in these parts, and in so many areas of the country away from the major VC hubs, have to be one thing above all else: clever. And there’s a lot they can learn from people who study this phenomenon (like Jeff), and people who’ve practiced it for a long time. We have tons of those here in Minnesota (and all over, really), including serial entrepreneurs who’ve proved bootstrapping works, over and over again. Many of these guys (and girls) are friends of mine, and they have accumulated a large amount of knowledge on bootstrapping based on hard experience. The key, of course, if you’re a budding entrepreneur, is to learn how to tap into the expertise of those folks.

There’s an easier way to begin getting educated, though. In addition to Jeff Cornwall’s book, when it comes out (UPDATE: it was published in January 2009), you might want to start with a book Jeff recommends by Seth Godin, called the “Bootstrapper’s Bible.”  It’s not new, but it is definitely a classic — here’s some background on it from Seth’s blog.bootstrappersbible

But here’s the big tip: DON’T BUY IT! That’s right, you can download the FREE ebook version — a “manifesto” as Seth calls it — as a PDF file, right here.

Is that cheap enough for ya??  Better go grab it while you can, before he changes his mind. Then, read up, go forth, and continue bootstrapping!

Raising Startup Money? Here’s 20 Ways

This is not the first post I’ve done that mentions Tech Coast Angels, one of the largest and oldest angel investing organizations in the country, which is of course in Southern California. (Here’s another good one from about 10 months ago.) Interesting that the term “angel” originated in the techcoastangelsentertainment business, but TCA has little to do with Hollywood. It sure has a whole lot to do with funding technology startups in that part of the country, though! (I also had the good fortune to do an extensive interview in early 2007 with the founder of Tech Coast Angels, the late Louis Villalobos, which was later published in The Angel Journal.)

This organization is actually comprised of four networks of angels covering a large part of the SoCal geography, from Santa Barbara down to San Diego. One of my favorite places, Orange County, is where the largest and oldest of these networks is situated.  And that’s where the subject of this post hails from.

Frank Peters, a successful, now semi-retired software entrepreneur (he marketed his product to Wall Street firms starting back in the ’80s), has been active as an angel investor for 10 years, and at the time of this post he’d been with Tech Coast Angels for five years. On the side, he produced a great podcast for a few years called “The Frank Peters Show” — subtitled “Startup Stories in Angel Investing and Venture Capital.” He was prolific — averaging about 60 podcasts per year for a while. Pretty amazing! These episodes provided some great listening for both entrepreneurs and angel investors. He had some excellent interviews with really interesting subjects. It was a podcast that definitely helped people better understand angel investing.

Frank did one great episode that was an interview with two experienced fellow TCA angels: Dave Berkus (how many angels do you know who’ve done 60 deals?), and Sid Mohasseb, who runs Venture Farm, which he described as “an equity funding source that adds hands-on experience to the execution process.” The topic of the podcast was “20 Ways to Fund Your Startup” — a list that Dave Berkus developed, but which all three guys discussed in this one-hour+ episode.  Here’s a quick rundown of the gist of that discussion:

THE BIG LIST: 20 Way$$ to Feed Your Startup Habit
Of the various ways to raise startup capital, angel financing is about in the middle of the continuum, Dave said. Some founders, however, try it too early — they don’t bootstrap enough first.  If you do, say the panelists, you’ll have a better chance of getting an audience in the first place to be considered to receive funding. So, here’s the rundown, courtesy of Dave, with some points noted by him and the others as he went through the list:

1) Credit cards – this can be $20-30k, even $50k in some cases, which will require a personal guarantee (but not mortgaging your house).
2) Securing arrangements with suppliers to slow down payments – assuming the business is started – or seeking deferred payment – lawyers typically do that – many even do pro bono work as a way to give back to the community.
3) Take out another mortgage – scary for many, perhaps, but rates remain quite low; it shows the founder has significant belief in what he or she is doing.
4) Wealthy relatives – “if you were born lucky” – they’re more likely than others to invest.
5) Friends – “means you’re getting lucky, if you have good ones!”  – can be on your board of advisors, too, which costs you nothing.
6) Take on consulting work – even let your company be both a consulting and product development business at first.
7) Affiliate with an incubator – whether physical or virtual – they can help build your management team and more.
8) Well-connected attorney – angels listen to their recommendations.
9) A “Rented” CFO – they don’t get paid for just getting the money, but for the financial systems they set up – the analysis of the data is what they deliver, and credibility.
10) Recruit a professional CFO – angels feel much more comfortable then.
11) Get prepaid licenses for your technology – a combination of selling service as well as product – maintenance agreements can be part of this (16-20% of list price of software) – recurring revenue –  customers are essentially paying for the engineering and product development – helps refine the value proposition – you don’t need to give it away for free.
12) Accelerated payments – of course, you have to have a revenue stream first.
13) Royalties for very specific projects – let those fund your product development – seek out anyone that can benefit from the technology (not just your main target customers).
14) Angel financing – “later the better” to approach them, because you’re then more likely to get funded – however, can be anywhere on the continuum – the later it is, the more likely you’ll get funded (angels will look at what you’ve done so far – how many of the above you’ve taken advantage of) – if you go to angels earlier, your valuation will be lower.
15) Bank line of credit – $50k is available to almost anybody with good credit (with personal guarantee).
16) Strategic partnerships – customer or supplier, helping to develop, promising to distribute, etc – helps to define channels for later sales and distribution.
17) Venture capital, pension funds
18) Private placements
19) Professional restructurers
20) Investment bank, public offering

Dave pointed out again that angels are more in the middle of this continuum — they aren’t where you start.  “They’re an avenue for the sophisticated entrepreneur that understands all the other sources and where the risk is, and how fast they need the money.”

In the closing discussion, Frank commented that TCA was ten years old at that point, and was getting more sophisticated.  Yes, the others agreed — and “more prudent, cautious, and jaded.”  But Dave added that it was certain they were much more powerful as a group than as individuals. Frank noted that the angel financing business, at least for TCA, things slow down towards the end of the year — until around mid-January.

Then, the three discussed a recent university study, in which certain TCA members participated, called “Angels in Groups,” for which a large amount of data on angel investments was gathered.  One of the biggest surprises of the study, they agreed, was the average length of time to a liquidity event. Many angels think of it as generally 3 to 5 years, but they noted that was not happening for those deals studied.  Dave said the study found that 61% of the angels surveyed had returns greater than the amount they invested, “meaning 39% didn’t!”  The conclusion is that angel investing is more risky than most people think. A diversity of investments is important “before you can count your chickens,” said Dave. Luis Villalobos, the founder of TCA, thought a portfolio of 25 or more investments was a minimum to expect good returns. The study showed that success happens when the angel is involved in the business. The entrepreneur benefits from the sharing of the experience of angels. Finally, the study found that it doesn’t tend to pay for angels to reinvest, which is somewhat worrisome, the panelists noted. “TCA traditionally funds 2-3% of deals they see,” said Dave. “But when we’re ready to take deals to VCs, those firms only invest in 1% of what they see, on average.”  Therein lies a problem, because angels often to have to invest a second or third time to keep the business going before it’s ready for the VCs. ‘”It’s a game of patience,” Dave said.

Frank Peters concluded this particular podcast by saying he thinks there’s a need to “start testifying more about angel investing, more education, chewing over issues.”

I like the list of 20 sources of startup money, though — it’s a list that all new and aspiring entrepreneurs need to know. There really are a ton of ways, and most of them do qualify as bootstrapping… or just plain being clever!

It Was Another Great ‘Minnedemo’ on Thursday Night

On a brisk Minnesota evening in early December, what better to do than get together to drink beer and watch demos with 200+ of your closest tech friends and talk code, startups, business models, and all that good stuff?
Minnedemo1207crowd Thursday night, the scene for Minnedemo again was O’Gara’s Garage in St.Paul, and the joint was a-jumpin’! We didn’t need a band — we were all our own entertainment!
Minnedemo1207ogaras

Thanks to our sponsors, we not only got two free beers (or sodas) each, but we also could trade canned food donations for even more beer tickets, so we could then play big shot and buy beer for our friends. Trading canned food for beer….does_it_get_any_better_’n_that? It was a hoot….lots of great conversation and new friends made. You have to be at one of these things to really appreciate the energy of the Minnesota tech community! If you haven’t caught one yet, make sure you get to the next one in April (date to be announced). Hey, it’s FREE — whadya want?!? 🙂 That one will be the full-day-Saturday version we call “Minnebar.” It all part of Minnesota’s answer to the worldwide phenomenon called Barcamp — and we are definitely one of the most active locales outside the Valley.

Here’s a rundown on Thursday night’s great presenters, including some detail about the very cool new products they were demoing:

Ntractive LLC (Dale Jensen, Cofounder/CEO) – This startup, based in Grand Forks, is a winner of the “InnovateND” award, and is receiving its first-round funding from St. Paul-based RAIN Source Capital. Ntractive has developed a “hybrid” app for small business management called “Elements SBM.” This app, initially for the MacOS, provides web application flexibility with unprecedented ease of use not generally found outside of the traditional desktop application. The result is a visually elegant and technically innovative solution that allows small business users to quickly become more productive. Minnedemo1207dalejensen The company officially launches at MacWorld in San Francisco in mid-January, but chose Minnedemo (yay!) as the venue its first public demonstration. Till now, small businesses had to choose a desktop app or a web app, but, said Jensen, “With our hybrid app, we’ve made it possible for the first time to really have the best of both of those worlds.”

Zencoder Video Transcoding System (Jon Dahl, cofounder of Slantwise Design) – Zencoder provides “bulletproof video transcoding.” Minnedemo1207jondahl It’s described as a full-featured video transcoding platform that handles every aspect of video processing, from queuing to transcoding to storage. Video transcoding systems are complex and difficult to get right, Dahl said. Zencoder claims its platform is reliable and scalable, costs far less than a custom-built solution, and yet is highly customizable. To be notified when it’s released, enter your email address at the site.

Valtira (Morgan Catlin, Product Director) – The Valtira Online Marketing Platform is a complete online solution for marketing professionals. It’s “software as a service” — all you need is a web browser. Valtira manages the IT infrastructure, operations, and upgrades from its Tier 1 data center. The platform empowers the marketing team to manage online initiatives without the need for IT support. Components include Content Management, Campaign Management, Blogging and Forums, Prospect Management, Email Marketing, Sales Portals, Social Networking, Online Surveys, Real-time Analytics, and Support & Training. Valtira just announced a new, free campaign tracking solution that lets you track up to 15 marketing campaigns.

JRuby (Charles Nutter) – JRuby is a 100% pure-Java implementation of the Ruby programming language. The JRuby community recently announced the release of JRuby 1.1 beta 1, the first release toward their goal of JRuby 1.1. JRuby 1.1 represents a concerted focus on speed and refinement. Ruby code can completely compile in an Ahead Of Time (AOT) or Just In Time (JIT) mode, yielding a faster Ruby! It uses less memory than previous releases. The community wants people to download JRuby 1.1b1 and provide feedback: “test your applications and help us make JRuby 1.1 a great release.”

Grapheety (Gavin Quinn) – A map-based social exploration site. All stories and pictures are tagged onto the map by users. For a part-time effort by a bunch of fulltime employed guys, it’s quite an effort. Read more about the latest release here on the Grapheety blog.

All in all, it was another super Minnedemo, and I’m very glad I was there! If you missed it and want more info on the presenting firms, please visit their sites and make contact with them directly. They’ve love to hear from you! Once again, many thanks to co-organizers Dan Grigsby and Luke Francl for another great job, and also to our illustrious sponsors. They’re awesome.

Rock on, Minnesota tech!

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