Slideshow: Who’s Investing Faster — DST or Andreessen Horowitz?

If this year already seems like a blur to you, imagine how the LPs of Andreessen Horowitz and Digital Sky Technologies (DST) must feel. Both venture capital firms are known for aggressively placing outsize bets on companies whose full potential they see as unfulfilled.

Still, when on Sunday night, they reported investing a combined $112 million in a 3-year-old company like Airbnb at a billion-dollar-plus valuation, even their staunchest supporters may have found themselves wondering exactly how much cash has flowed out their doors so far this year.

Or maybe it’s just us who are curious. Either way, follow along as we tour past the massive investments that both firms have participated in since January — deals that underscore the biggest difference between the two, as well as suggest which firm has put more money to work. Note that we have made some educated guesses in some of the dollar amounts below.

[slideshow]

[slide title=”JANUARY”]
One word: Groupon

Both DST and Andreessen Horowitz participated in the round that was like, a billion dollars, which, like, went mostly into the pockets of the company’s earliest investors and employees, and that is now giving everyone, like, the willies about the pre-IPO company’s long-term prospects.

Lots of firms participated in the round, including Battery Ventures, Greylock Partners, Kleiner Perkins, Maverick Capital, Silver Lake, and Technology Crossover Ventures (with previous funding rounds led by NEA, Accel, and DST).  Left to imagine who put in how much, let’s say DST and AH both contributed $100 million. (We know that’s not an oversize gamble in DST’s view. Meanwhile, Marc Andreessen told me back in December that AH would put up to $100 million in a deal. My guess is that he wasn’t speaking theoretically.)

Best Guess Total for January:
AH: $100M
DST: $100M

[slide title=”FEBRUARY”]

February was a slow month for both firms. (Phew.)

DST didn’t report a thing. Meanwhile, it looks as if the only investment to be reported for Andreessen Horowitz was TinyCo, a San Francisco-based mobile game startup that raised $18 million in Series A funding led by — who else — AH. (Marc Andreessen himself joined the board.) No other venture investors were announced, so I’m going to assume that aside from some individual investors, “led” in this case means “funded the company almost entirely.”

Best Guess Total for February:
AH: $18M
DST: $0

[slide title=”MARCH”]

Ah, March. Here we have another of DST’s characteristically rare but massive investments. Near the end of the month, DST reportedly participated in a $1.5 billion round for 360buy.com, one of China’s fastest-growing e-commerce companies. And when DST participates, it goes full out, committing to $500 million of the round. (Tiger Fund and Walmart were among others to fill out the giant financing.)

Do you think Andreessen Horowitz was taking a breather at the time? Oh, no. Along with Lightspeed Venture Partners and Ignition Partners, AH participated in the $9.2 million Series A round of Bromium, a virtualization and cloud security company.

More, AH stunned much of the industry in March by investing, gulp, $49 million into the wireless headset maker Jawbone, which also now makes an electronic bracelet called the UP that tracks users’ movements, sleep patterns, and eating habits, and relays the information to a phone app.

(More shocking: two weeks ago, Jawbone raised another $70 million from investors advised by J.P. Morgan Asset Management.)

Best Guess Total for March:
AH: $52M
DST: $500M

[slide title=”APRIL”]

There were no big deals for DST in April, but Andreessen Horowitz went on a tear. It participated in the crowded $1.75 million funding round of Listia, a sort of eBay for free stuff that was spun out of Y Combinator.

It participated in the $5.45 million round for the still-stealth mode startup Clover Networks, led by well-known Silicon Valley executive Mike Speiser. (Sutter Hill Ventures and Morado Venture Partners also participated.)

AH, along with Accel Partners, also gave the online games maker Tiny Speck $10.7 in Series B funding.

But that’s not all. AH led a $12.6 million Series A round for the four-year-old, social, enterprise-focused startup Magnet Systems, a financing that was rounded out by individuals, including Alfred Chuang, the company’s CEO.

And AH participated in the newest, $30 million round of Kno, a textbook tablet maker that recently dropped the tablet part of its business to focus on software. The company has already raised $89 million since its founding in May 2009, much of it from AH. (Kno’s new round was led by Intel Capital and Advance Publications, with participation from earlier investors, including AH, Floodgate, First Round Capital, and SV Angel.)

Best Guess Total for April:
AH: $25M
DST: $0

[slide title=”MAY”]

If DST funded anything in May, the media didn’t hear about it. Meanwhile, Andreessen Horowitz had, as always, a few things cooking.

AH participated in a $7.6 million Series A for BlueStacks, a startup whose technology should allow users to run Android and Windows applications on x86-based devices. Redpoint Ventures and Ignition were also in the round, along with a couple of other firms.

AH also participated in a crowded, $1.6 million round for Grubwithus,a company launched out of Y Combinator last year. (DST’s Yuri Milner is also an investor in Grubwithus.)

But AH’s biggest deal of the month was ShoeDazzle, a subscription-based fashion deals Website founded by Kim Kardashian and LegalZoom co-founder Brian Lee. ShoeDazzle raised $40 million, $30 million of which reportedly came from Andreessen Horowitz. (Polaris Venture Partners and Lightspeed Ventures — previous investors in ShoeDazzle, which has now raised $60 million in its two years — pitched in the rest.)

Best Guess Total for May:
AH: $32M
DST: $0

[slide title=”JUNE”]

Whoa, Nelly. June was a big month for both venture firms from a financial standpoint, although DST made one investment, while Andreessen Horowitz made a handful.

In June, DST, along with Kleiner Perkins and Accel Partners, reportedly participated in a $100 million round for the streaming music company Spotify that valued the company at $1 billion.

Meanwhile, Andreessen Horowitz led a Series A round for LikeALittle, a location-based social network based in Palo Alto that raised $5 million, presumably mostly from Andreessen Horowitz. (No other venture firm was announced as part of the deal, though some angel investors participated.)

The firm also took part in a $30 million Series B round for browser company Rockmelt. The round was led by Accel Partners and Khosla Ventures, with Andreessen Horowitz and individual investors rounding things out. Wild guess here, but given that AH is one of three actual venture firms in this Series B, let’s say it invested $6 million or $7 million.

And Andreessen Horowitz backed Silver Tail Systems, Inc., which sells fraud and abuse detection and prevention software. AH led its $20 million Series B funding. No other venture firm was announced as a co-investor, and Silver Tail’s Series A backers are tiny (Leapfrog Ventures, Seraph Group, and Startup Capital Ventures), so likely it was responsible for most of the round.

Last but certainly not least, there was that $50 million round for the location-based social network Foursquare, which was led by Andreessen Horowitz and included participation from O’Reilly Alpha Tech Ventures, Union Square Ventures and Spark Capital. Notably, AH also led a $20 million B round for the company, whose newest funding reportedly values it at $600 million. (Seems a little strange for a firm to lead two consecutive rounds, though I suppose it could be interpreted as an enormous vote of confidence.)

Again, I don’t know exactly how much each investor chipped in, but I’d guess Andreessen Horowitz contributed (conservatively) at least $20 million. Here’s why: O’Reilly Alpha Tech Ventures’ newest fund, closed last December, is a $59 million vehicle. Meanwhile, Union Square Ventures’ newest fund is a $165 million vehicle that it closed in January of this year.  Neither are big funds, they’ve both invested in Foursquare in previous financing rounds, and it’s generally bad form for any firm to invest more than 10 percent of a fund in any one deal, including follow-on rounds. The biggest question is how much Spark Capital contributed to the deal. Spark closed on a $360 million fund last fall, so it likely contributed the second biggest of capital to the round.

Worth noting: In June, Andreessen Horowitz also participated in a seed deal for the stealth motion control startup OcuSpec. But since that round totaled $1.3 million, it’s not worth factoring in here.

Best Guess Total for June:
AH: $55M
DST: $33M

[slide title=”JULY”]

On Sunday, Airbnb, the travel-rental startup, announced it has raised $112 million from Andreessen Horowitz, Digital Sky Technologies, and General Catalyst, along with previous investors.

TechCrunch further reported hearing that AH invested $60 million, DST invested $40 million, General Catalyst invested $5, and Series A investors like Sequoia Capital chipped in the rest, along with Jeff Bezos.  We’ll assume those whispers aren’t far off, given that TechCrunch learned of the round two months ago.

So far this month, Andreessen Horowitz has also funded Capriza, a months-old, Israeli-based mobile startup that’s focused on enterprise customers but remains in stealth mode. At least, it’s in the process of raising a $10.5 million round, and roughly $8 million of that round has come from Andreessen Horowitz, according to a local paper called The Marker.

Best Guess Total for July:
AH: $68M
DST: $40M

[slide title=”SO YOUR POINT IS?”]

What does it all mean, aside from the fact that Andreessen Horowitz has probably invested roughly $350 million into startups this year, and that DST has invested around $675 million? Well, most obviously, it means that DST is still making fewer and bigger bets than Andreessen Horowitz. (Indeed, rumors suggest DST may also be plunging $400 million into the next financing round for Twitter, which would put it well past AH in terms of dollars invested since January.)

It’s also plain that these guys better have as hot a hand as they seem to have. It’s exciting to watch, but hard not to think there’s good reason that VCs haven’t traditionally invested hundreds of millions of dollars in such a short amount of time.

Says one prominent Sand Hill Road VC: “I haven’t seen checks fly around that are this size, ever. To the extent that [2011] is [the rough equivalent of ] 1996, they’ll do just fine. If it’s 1999, they’re in trouble.”

[/slideshow]