My Armchair Quarterbacking of the Election

Last week Donald Trump upset Hillary Clinton to win the presidency.

I  think it’s important to realize that hindsight is 20-20, and it’s easy to criticize from my place of limited information. A loss causes a lot of armchair quarterbacking. Sometimes the people on the ground made the best choices possible with the resources or information they were given at the time. There are many people who put WAY more into this campaign than I did.

So please don’t interpret any of the following as overly judgmental “I could have done it better.” Probably not.

That said, the following is an analysis of what I think went wrong.



I think if Joe Biden had run the exact same campaign many of the blue collar workers that didn’t think Clinton was really resonating would have come around. I think they would have seen themselves in him.

I think sexism had a lot to do with how Hillary has been judged as this awful duplicitous bitch for much of her life and once it was said so many times, even liberal people inclined to like her thought it was true.

I think sexism meant that many men, insecure as they were no longer at the top of the totem pole, lashed out at the idea of being subservient to a woman. I think many men viewed it as the ultimate emasculation, in a society that they think has already become too effeminate, with legalization of gay marriage, the increase of white working class unemployment, to now be bossed around by a woman, and even maybe had some psychological holdups about “bitchy” women in their lives like their wives or mothers.

Product-Market Fit & Messaging

Let’s compare Hillary’s operation to a startup. They built this big product, but didn’t do adequate customer research. And when she got a wakeup call from Bernie that perhaps she didn’t really “understand her users” she didn’t really internalize it. Instead she continued trying to convince her customer that the CEO of the competing company was a shady sexual predator, and that his answers were racist.

The customer was sitting there going “ok yeah, I agree, he’s a racist creep, but he’s actually giving me answers to my problems, and you aren’t.” Hillary then would launch into a 75 slide powerpoint presentation that tried to address said problem and their eyes would gloss over.

I know that Hillary probably had great messaging people on board, but I think their messaging was focused on some wrong core assumptions: that people cared about Trump’s character and the character of a President more than these other economic anxieties, that they could make him so reprehensible as to make him not acceptable to anyone half-way decent. I know the polls supported that idea as well.

I’ve realized by pitching my own company how essential nailing the messaging is: are we addressing the actual problem a potential client has been trying to solve? Our pitch falls flat when we have misdiagnosed their problem.

Or more importantly, weren’t able to get the message through because we didn’t present the message in a short number of slides, with few words, mostly images.


This isn’t meant to be insulting to Trump voters: hell, Silicon Valley VCs have short attention spans. EVERYONE needs things presented in this way.

Hillary herself would often say to “campaign in poetry, govern in prose.” And then go and campaign in prose.

I don’t think our side gave them a good counter-narrative/message to replace his despicable one, and when we did, it didn’t break through. Instead much of the focus was on shaming the racist views Trump held, and that wasn’t a deal breaker to these people who were hurting.

Messaging beats Product. Trump basically had NO product, he ONLY had messaging. And he won.

Backlash to/Effects of PC Culture:


(Image Credit: South Park Safe Space Music Video)

There is a lot of talk about how “leftist-PC” culture was really what these Trump voters were rebelling against.

I always thought the idea that someone was going to vote for a candidate because they were sick and tired of us telling them not to be insensitive racists was a little ridiculous. We were never going to win those votes anyway.

But I draw a distinction between actual racist, sexist and bigoted people, and the many people who make honest mistakes, and PC culture jumps down their throat.

I had a conversation a couple years ago that still sticks with me.

I referred to a trans person as a he when she had transitioned to a female. I was corrected and apologized. I followed it up by asking a question to clarify how something worked in a trans relationship, etc. I was curious, I didn’t know. This person knew 100% that I was an ally.

I still remember the reaction: my friend got angry at me for even asking and being ignorant and I kept on saying “I’m sorry but I don’t know, I’m not passing judgement, I’m just curious, why are you getting mad at me?”

She kept on saying the question itself was inappropriate.

I see this a lot with self-righteous liberals who put an emphasis on words over intent, and take every opportunity to assume the worst instead of every opportunity to assume the best.

And it only alienates potential allies.

This has happened to me numerous times in other ways. I’m a big supporter of Hillary now but 8 years ago I supported Obama, and when I told people I didn’t like Hillary back then (origin: some misplaced liberal idealism that I’ve now gotten over) I was called sexist.

All sexists hate Hillary, but not all people who dislike Hillary are sexist. And it only pisses off people who have a legitimate reason to not like her when you equate them to sexists. 

They dig in. And you don’t reach them.

I certainly don’t think this was the deciding factor like many conservatives are all too eager to make it out to be. The people touting this are often people eager to normalize truly reprehensible speech. But I think the disdain for someone who would even consider voting for Trump, and the jumping to conclusions that they must be racist and sexist to even consider it, definitely contributed to people not sharing their opinions, and eliminated the opportunity to really engage them.

More reading, and the only time I will ever link to


Enthusiasm Gap Among Millenials, POC and Bernie Bros

Despite running a sociopath, racist, sexist former Democrat, Republicans still turned out for their candidate. We ran the most qualified nominee in the history of presidential races and she wasn’t “inspiring” enough for us.


I keep on hearing people say that it’s the candidates responsibility to convince voters. Yes, true. I addressed that above. It’s also our civic duty to educate ourselves and do research on who is the best candidate, warts and all.

Until you yourself run for president, you are never going to agree 100% with everything a candidate stands for. So it’s ALWAYS a lesser of two evils choice.

It’s our responsibility to not be such morons and cut off our nose to spite our face. Where were the 20M people who got healthcare through Obamacare? Where were all the LGBTQ allies? Where were all the liberals who supposedly cared about the poor? Where were the African Americans who wanted to defend President Obama’s legacy?

It’s everyone’s responsibility to make the best choice possible, not just Hillary’s to inspire you to.

Bad Campaign Infrastructure

While canvassing in Nevada we were given paper and pen and lists of voters. A friend of mine went to check out the Trump campaign and just chat with them, and they had an app. The guys who raised maybe half as much money as us had an app and we didn’t. And it’s not like these things aren’t easily available, Organizer is a Democratic Party aligned company that provides canvassing software. We actually had WAY more volunteers than the Trump campaign, something that really excited us at the time. But no tech. There were local congressional and state senate races using better tech in the field than the Hillary campaign. At one point I spoke to a spurned Bernie supporter that had been contacted by 8 different Hillary volunteers by the time I got to him the Sunday before the election, and I had nothing new to say because I hadn’t prepared to have that conversation. I was blindsided. With preparation and notes properly logged I would have been able to plan how I engaged with him.


(Image Credit: Organizer: much better than pen and paper)

I saw this repeated throughout my limited involvement in the campaign. I planned a fundraiser for Hillary with Mark Cuban and Chris Sacca. That was 2 months of work, 90+ emails back and forth. But we were informed that the event was actually happening 4 days before and most of the money we had committed dropped out because our cohosts couldn’t raise the 5-10k they had each committed from their networks in 4 days.

Our original intention was to throw a smaller event where people more in my demographic (startup founders with maybe the ability to write a $500-1000 check, but not much more) were the VIPs. We had 15 cohosts, a venue, around 80k committed and we just wanted one mid-level surrogate.

From what I understand this is basically what Obama did with his network of house parties in 2008, he empowered grassroots organizers. People who wanted to get more involved than donating $27 online, but couldn’t attend a 10k a plate fundraiser, still had a place to organize and mine their networks and get people excited.

We spent 2 months coordinating with the campaign, and finally after numerous attempts we gave up when we were offered to blow the event up into a much bigger event with Mark Cuban. It wasn’t the type of event I wanted to throw, and we lost most of our cohosts. Several Republicans who I had convinced to switch over, and who had committed 1-2k just dropped out entirely and I’m pretty sure never contributed.


Backstage at the event I was chatting with one of the major donors, who told me he had given millions to Obama. He said the Clinton campaign only called him up a few weeks ago for the first time, ~8 weeks before election time. He said he had tried to give the campaign a call. When he got on the phone with someone told them he wanted to write a check for $1M.

The guy told him he was not the right person to speak to.

If someone called up my company and told me they wanted to give me a million dollars I hope my team would be trained to know where to escalate that to . . .



Extending the startup analogy, one of the reasons I heard Obama’s campaign was so nimble was because it was a real startup. Clinton hired many of those people. But I felt like it was an acquihire: it was like General Electric’s board got together and said “we have to inject some startup culture into our behemoth of an organization.”

As anyone who operates in the startup/business world knows, that rarely works. Changing 10%, or usually much less, of the workforce doesn’t change the fundamental culture that led to the organization being big and clunky in the first place.

My observation, again from the outside and very limited and anecdotal, is that a lot was still done in an old school fashion.


I’m Guilty

I definitely chose Clinton over Sanders despite knowing that Sanders had the better message. I thought the boring, traditional, moderate, more hawkish ground breaking candidacy that had been tested over 25 years was a better bet than the Jewish Atheist Socialist Dove. I thought women would turn out in droves for the first woman candidate, I thought we were ready to elect a woman, and I thought our country was significantly more moderate politically, and nowhere near as sexist or racist, than it turns out it is. I can’t blame the Hillary campaign for thinking the same, in the end that was an error of assuming the best about our country’s fundamental decency . . .

I looked at history and saw numerous instances where we were told we could run our dream liberal candidate, Dukakis, etc. and we lost in a landslide, and I thought Bernie supporters and Bernie himself underestimated our older generation’s visceral reaction to anything even slightly similar to communism, feelings that drove people like my Estonian immigrant grandparents to be lifelong Republicans, in his unabashed needling of capitalism.

The counterfactual is hard to prove, but obviously some of those assumptions were wrong. I’m not sure Bernie would have done better, I think there was a lot of healthy oppo research that never came out that could have doomed him, so I don’t agree when people say “if only we had run Bernie it all would have been swell” but I definitely underestimated a lot of Clinton’s downsides in retrospect.

In the future I will be prioritizing the message that resonates the most when I choose a candidate to support.

I also definitely chose to shame people instead of listen at times. I think there are a large chunk of Trump supporters who are racist or sexist. But there is a large chunk who are genuinely hurting, and were just voting in their own self-interest as nothing has worked for them in the past.

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