An Awkward Twitter Exchange With A Former Employer

edit: apparently, this article has gotten a fair bit of attention from Hacker News. There’s a link here.

edit 2: the HN link was flagged and removed.

edit 3: like adults, Kevin and I talked out our differences. I still think he came off as exceedingly callous, and we still fundamentally disagree on several core issues here. But we both have a fair bit of common ground. While I still feel justified in initially writing this little post, know that I feel comfortable discussing these issues with him and anyone else on reasonably civil terms.


Unless you’ve been living under a rock, you’ve probably heard that the American Health Care Act, known by many as Trumpcare, died a somewhat ignominious death on the floor of the US House last week.

I say good riddance to the bill. And, moreover, I tweeted out “Next stop: Single Payer” because I’m a fan of the idea of single payer healthcare. (I’m no policy expert in much of anything, much less healthcare, so I openly admit that my affinity for single payer is purely based on feelings.)

So anyways, who parades into the @-replies like the little kid in the Robert Kelly BBC video but the CTO of the company I used to research and write for… Continue reading “An Awkward Twitter Exchange With A Former Employer”

Rothenberg’s Wake: Does One Fallen Domino Signal Future Failures in Micro VC?

Earlier this week, Backchannel published a piece chronicling the “Trouble In The House of Rothenberg”.

For those unfamiliar with the story, Mike Rothenberg is – or, was – an uber-connected 31 year-old solo general partner of Rothenberg Ventures (which changed its name to “Frontier Tech Ventures” this week). He was known for being one of the best-connected “millennials” in Silicon Valley, his rapid turnaround on deals, throwing raucous and very expensive parties, unorthodox management fee structuring and carried interest distributions, and funding his (failing) startup project with $5 million of Rothenberg Ventures’s capital. (~10% of the entire firm’s AUM.)

TLDR is: His fund ran out of operating capital, his investors are Royally Pissed, and he’s facing possible scrutiny from the FBI and SEC.

The question is, is this a one-off event or a signal of more failures to come in the micro VC space. As I’ve previously written about there is a real explosion in the number of funds with less than $100 million in assets under management, many of which are raised by first-time fund managers.

How many of them are spending too much of their small management fees on marketing, events and providing services to their portfolio companies? Rothenberg is the apotheosis of “young VCs go wild” stereotypes. I mean, the guy inscribed his VC fund’s logo into his bathroom tile.

But there are surely many like him. Excess and irresponsibility exist on a gradient, and it’s worth identifying the funds on the darker grey side of the spectrum sooner rather than later.

There is a lot of good that small funds can do, but the VC community might want to proactively prevent stuff like this from happening again. In the meantime, those looking to raise should hope that one very public bad apple doesn’t sour LPs to the prospect of investing in smaller funds.

Notes on Twilio, Line And The Open (?) Window

After several quarters of disappointing news from public tech companies (primarily those affiliated with Jack Dorsey, but I digress) and story after story about private tech companies’ reluctance to go public, Twilio may have blown open the tech IPO window on Thursday. Making its debut on the NYSE under symbol TWLO, at the price of $15/share, shares in the cloud communications company opened at $23.99, 60% higher than its initial offering. Shares hit an intra-day high of $29.61 and closed at $28.79, up over 90% for the day. (Shares in Twilio, like most other companies, experienced significant declines in Friday trading thanks to Brexit news.)

For more information and context on the Twilio IPO, check out some of these resources:

  • My friend Alex Wilhelm’s note on the IPO for Mattermark. (Also, thanks to Alex for linking to the EquityZen report mentioned below.)
  • This analysis from EquityZen shows that Bessemer Venture Partners owns 28.5% of Twilio. Bessemer generated a 27.4x multiple on invested capital on its Series B investment and 9.6x MOIC its Series C follow on.
  • That same report finds that Union Square Ventures generated an 82.3x MOIC on its Series A investment.
  • Fred Wilson, general partner at Union Square Ventures, says that Twilio’s was the best seed pitch ever. Proof positive that a live working demo trumps even the best pitch decks.

Whether or not Twilio’s public offering is a one-off success or the beginning of a trend is impossible to say, because it was the first major tech IPO this year. (One data point does not a trend make.)

The next scheduled IPO is for Japanese mobile messaging app Line, which is slated to go public on the NASDAQ on July 12. (More info on Line’s impending IPO can be found on the NASDAQ site.) Although all eyes will be on Line and the market’s reaction to its debut, there are some things to keep in mind (notes cribbed from Bloomberg):

  • Line filed for an IPO almost two years ago on the Japanese market at a valuation of 1 trillion yen. July’s IPO valuation, which will make shares publicly tradable on US and Japanese markets, is expected to be 588 billion yen, or 40% lower.
  • Facebook has steadily encroached on Line’s key product areas with the launch and continued expansion of Messenger, and its acquisition of Whatsapp.
  • Line’s average user is valued at $25 per user, less than half of the $55/user Facebook paid for Whatsapp.

Line is also unlike Twilio in that it’s not an infrastructure play. Remember that during a gold rush it’s best to invest in the people making the shovels, which is ostensibly why Twilio has performed so well… they built the platform that helped to catalyze the mobile app boom. Line has stiff competition from WeChat to the west and Snapchat, Messenger and Whatsapp to the east. And, unfortunately for Line, it’s one where the customers are more fickle.

Investors interested in this IPO should proceed with all the expected caution and due diligence, remember that one tech unicorn is not necessarily like another, and remember that past performance is not necessarily indicative of future results. There’s always room for an upside surprise.

SF Was Killing Me

Reading Larry Finn’s blog post on the San Francisco Bubble prompted me to resurrect this ~1640-word stream of consciousness from the Drafts folder of my WordPress installation. I wrote this approximately 4 months ago.

In lieu of tying up its ending into some nice concluding thoughts, I’ll just publish it here as is.


Almost exactly two months in The City, and I was through. I was on my way back to the city of big shoulders. “I like Chicago,” said someone at the other fund, “everything is bigger there.”

In my time I have seen real estate fliers earnestly touting the features of a $1.9 Million two-bedroom loft space smaller than the upstairs of my mom’s house. I’ve met people who pay the equivalent of a payment on a $1M mortgage per month to live in one-bedroom apartments with hardwood cabinets, granite countertops and low-flow toilets which cannot seem to get the job quite done. I’ve consumed a shameful number of $15 cocktails at twee bars and backroom speakeasies while speaking glibly about investing and sans serif typeface design. I have not, however, consumed a sufficient number of $15 cocktails –  replete with artisinal cherries, obscure spirits, some of which were mixed and barrel aged, as one SaaS-y CEO mentioned, “onPrem” – to forget that the air in the bubble is rarified. Continue reading “SF Was Killing Me”

This One Weird iOS9 Bug Made Me Briefly Speculate About TouchID’s Potential for My Laptop

For the life of me I cannot seem to reproduce the bug, but I swear to the deity of your choosing that this morning, my iPhone 6 (currently running iOS 9.0 build 13A344) entered Apple Pay mode while it was plugged into my rMBP.

I have no card readers on my couch, but it got me thinking about something. Continue reading “This One Weird iOS9 Bug Made Me Briefly Speculate About TouchID’s Potential for My Laptop”

Best of The Halcyon Days

It’s been over two years since I published something to this blog, to which I published assiduously when I was in college at The University of Chicago, but began to neglect when I left to work on Mergenote, a startup of mine.

As I figure out what I want to do with my personal homepage, jasondrowley.com, and contemplate archiving this blog, I figured that it behooves me to have something other than a post on Overcoming Writers Block from two years ago (the irony of which does not escape me) to be the first thing you see.

Here is a list of some of my favorite posts from The Halcyon Days (in no particular order):

So, that’s that, then. I hope you enjoy the reading.

If you have any suggestions of what I might do next with my website, I’m all ears.

JDR Gets Down to Business, & HD Takes a Week Off

I will be taking a week off from writing effective today. I’m in the midst of tidying up a business plan for a venture I’m launching with two friends; between finishing that and getting in touch with lawyers and finding developers, a decent marketing/design guy/girl, and getting content for a website together, I’m kind of coming loose at the seams. Like a well-loved stuffed animal.

I’ll continue to update JDR Found, my Tumblr-powered scrapbook of things I find online.

I’ll be back a week from today!