Oct 26, 2015 ยท 7 minutes

The idea of Ron Conway as a machiavellian genius in SF politics rarely survives your first encounter with the slightly bumbling, shambling man himself.

Would an expert political operative really stand on stage at the Crunchies and genuinely believe he's paying tribute to a female CEO by telling a hilarious anecdote about a time when she tried to drive home drunk? Would Silicon Valley’s answer to Karl Rove really get his Facebook founders so confused that he once name-dropped “the Saverin Twins” to an audience of young entrepreneurs?

Closer to the truth is the image of Conway the connector: a man constantly trying to make new links between nodes in his sprawling personal network, to set up new deals and to maximise the value of those already in play.  [Disclosure: Conway is a Pando investor, through SV Angel]

Still -- whether through a lust for power, disdain for meddling civil servants, or just the love of the deal – there’s no denying that, thanks to his closeness with Mayor Ed Lee, and his role as investor in some of the city’s biggest startups, Conway has networked his way to significant political clout in San Francisco. And he has been willing to leverage that clout by lobbying – directly, and through his lobby group, Sf.citi, for all manner of political causes: from the liberalisation of laws impacting the sharing economy (the infamous "asking forgiveness" we're forever told is better), to environmental issues, to funding attack-ad campaigns against candidates who dare stand against his political friends.  

Such is politics, such is money.

And yet. Whatever your opinion of Conway’s political skills and motivation – Koch-brother-level evil genius or well-meaning meddler – a mass email he sent late last week to portfolio CEOs will likely confirm it. 

The email, sent to "San Francisco-based SV Angel Portfolio CEOs," was headed “SF Election Recommendations for November 3rd” and sets out Conway’s preferred positions for San Francisco’s upcoming municipal elections. Specifically, Conway asks the CEOs of companies in which he’s invested to “please share the list below and ask your team to Vote either on November 3 or by absentee ballot beforehand!” 

(Pando received the mass email as an SV angel portfolio company. Nothing indicated it was not for publication. I emailed Conway for comment yesterday evening, but haven’t heard back yet. I’ll update this post if he responds.)

There is no better illustration of Conway's political modus operandi than this...

From: Ron Conway 

Date: October 24, 2015 at 12:01:55 PM PDT

To: Ron Conway 

Subject: SF Election Recommendations for November 3rd

TO:  San Francisco-based SV Angel Portfolio CEOs

We have an important election in SF on November 3rd.

Can you please share the list below and ask your team to Vote either on November 3 or by absentee ballot beforehand  !

Candidate and proposition recommendations in the upcoming election in SF on November 3 :

Ed Lee  Mayor in all 3 choices (rank choice voting)

Vicki Hennessy  Sheriff  in all 3 choices (rank choice voting)

Alex Randolph  Member, Community College Board

If you live in District 3 in SF vote FOR Julie Christensen in all 3 choices (rank choice voting)

Not Voting for candidates for City Attorney, District Attorney or Treasurer


These recommendations match those of  sf.citi.

Measure A

General Obligation Bond Election - Affordable Housing - Not to Exceed $310,000,000


Measure B

Enhancement of Paid Parental Leave for City Employees


Measure C

Expenditure Lobbyists Ordinance


Measure D

Mission Rock


Measure E

Requirements For Public Meetings of Local Policy Bodies


Measure F

Short-Term Residential Rentals


Measure G

Disclosures Regarding Renewable Energy


Measure H

Clean Energy Right to Know Act


Measure I

Mission District Housing Moratorium


Measure J

Establishing the Legacy Business Historic Preservation Fund


Measure K

Surplus City Property Ordinance




Let’s get the obvious question out of the way: Yes, it’s perfectly legal for Ron Conway to send an email to the CEOs of companies in which he’s invested, asking them to tell their employees to vote a certain way in any local or national election. And, yes, it’s equally legal for those CEOs to take Conway’s advice and to strongly suggest – request, even – that their staff vote tgar certain way.

After Citizen United, there are very few limits on what an employer can say to his employees regarding voting for one candidate or another. Mitt Romney came under fire in the last presidential election for encouraging employers to nudge their staff to vote for him over Obama. Most commentators agreed that the practice was shady -- anti-democractic, even -- but none could cite a specific law that prevented the practice. In fact, in California, for many classes of employee, there’s nothing even to stop bosses warning workers they might be fired if they don’t vote along party lines.

So, Conway hasn’t broken any laws, and nor will any CEOs who acts on his email. Rest easy, Silicon Valley, you haven't disrupted any laws this time. I know that's a big concern.

And yet. And yet. It simply cannot be a good thing for local democracy that a single voter – Conway – by lieu of having invested in a lot of local companies has the clout to shape how thousands of voters cast their ballot on November 3rd. And I don't mean low thousands: At last count, Conway has invested in 546 companies, many in the Bay Area. We’re likely talking tens of thousands of employees who work for one or another of Conway’s portfolio CEOs. 

Worse than that, many of the employees are young tech workers who – generally speaking – are not usually too interested in local politics. Hell, I am interested in San Francisco politics, not least because of Dan Raile’s excellent coverage here on Pando, and I’d struggle to tell you how I’d vote on several of the ballot initiatives above.

Presented with a handy cut-out-and-keep guide to “tech friendly” ways to vote in the election, especially when it comes directly from your boss, with a note about the importance of keeping a key investor happy, it’s easy to see how tech workers might be happy to outsource their political thinking to Conway. Never mind that in at least one case, Conway’s suggestion – vote “no” on Prop F – will directly benefit Airbnb, the $25.5 billion startup in which Conway has invested since its Series A. In most others, the Conway Approved measures happen to be ones supported by his political friends.  

It hints at a certain contempt – intentional or otherwise – for the democratic process that Conway doesn’t even pretend to explain why recipients of his email should vote a certain way. He simply lists the initiative and how techies should vote. “Don’t trouble yourself with the details,” Conway seems to be saying. “I know what’s best for you.” In some cases – better paid leave for city employees, stricter disclosure requirements for lobbyists – perhaps no explanation is needed. Others are less obvious: Why, for example, does Conway oppose Measure E, which would require all public meetings and proceedings to be livestreamed to increase visibility? Does Conway have some reason to hide how the city’s sausage is made? Or is the proposed law just plain bad? (SF Examiner says the latter.)

It gets weirder. In some cases Conway suggests that his portfolio CEOs and their employees don’t vote on certain races. Thousands of potential voters, urged by their patron to not vote for City Attorney, District Attorney or Treasurer. Again: Why?

Like (probably) most Pando readers, I usually roll my eyes when I see posters around San Francisco, blaming Ron Conway for all the city’s ills. But crap like this just plays into the hands of those who believe – with more than a little justification – that the tech industry has city hall in its pocket, and that Ron Conway can basically pass any laws he likes, or kill those he doesn’t. In other words, that Conway is Rose Pak 2.0.

Conway is right on one thing: November 3rd’s election is an important one for tech workers in San Francisco. Thanks to Proposition F, it’s a referendum on the sharing economy and for how the city feels about the techies in its midst. But for the results of that referendum to actually matter a damn, voters need to cast their ballot having actually read and understood the issues at hand, not under orders from on high.