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By: Mark Glennon*


A firestorm broke out today in the national media over an email by the Founder/CEO of Chicago-based GrubHub, Matt Maloney, to all employees, essentially telling Donald Trump supporters to resign. There’s a major learning experience to be had in this affair. It’s not just the usual story about intolerance on the left. It’s about how an exceptionally bright person can be exceptionally blind to the certainty of self-inflicted harm. It’s about why the phrase “just don’t get it” isn’t just some platitude in the Donald Trump saga. It’s deeper than we knew.


I know Matt and worked with him quite closely. That background is relevant, as you will see. The background also contains another lesson everybody should remember.


Seven years ago I was with a venture capital firm and we were trying to negotiate an investment in GrubHub. It was then a very small company operating in two cities with maybe 30 or 40 employees. Matt and his co-founder were unusually talented — gifted in many ways — and I really liked the opportunity. However, they were then both very young, brash and difficult — two other VC firms I knew had turned them down for just that reason.


As a final decision time approached I had a heated impasse with Matt about a few of the deal terms. He was being so obnoxious that I pulled the phone away from my ear and started to hang up on him. I truly and literally had a count to ten moment. “Wait,” I told myself, “this is a great opportunity and Matt doesn’t know any better. Don’t act on emotion.”


I kept talking. We completed the investment and I later served on GrubHub’s board. They went on to do wonderfully — though I take no credit for that, much of which goes to Matt. The company now operates in over 500 cities, is publicly traded and is worth over $3 billion (at least it was earlier today). Matt turned out to be a fantastic steward of shareholder money, and I am very grateful for that. (I no longer have an interest in the VC investments we made in GrubHub, which I disposed of after its IPO.)


But this isn’t about the obvious first lesson, which is not to speak or act when you’re angry. Always count to ten first. This is about Matt’s email to his employees and why somebody so smart would do something so knuckleheaded, insulting to many customers and against the interests of his shareholders.


The full text of the letter is linked here. If you agree with Trump you should resign. I think that’s a fair summary any employee would take away from the email. It says,


I absolutely reject the nationalist, anti-immigrant and hateful politics of Donald Trump and will work to shield our community from this movement as best as I can. As we all try to understand what this vote means to us, I want to affirm to anyone on our team that is scared or feels personally exposed, that I and everyone else here at Grubhub will fight for your dignity and your right to make a better life for yourself and your family here in the United States.  If you do not agree with this statement then please reply to this email with your resignation because you have no place here.


I immediately shot off a profane email to Matt when I saw this in the press today. His response indicated to me that he actually may have thought his email was harmless. I’m reading between the lines on that but I think he might really believe he was just preaching togetherness in the letter. He subsequently released a clarification, linked here, which indeed tries to claim that the “email that was intended to advocate for inclusion and tolerance.”


Even with that clarification, I’d say GrubHub employees now know damn well they better not say anything nice about Trump around the water cooler, have his sign in their yard, his sticker on their car or their name on his list of contributors, which is public.


It’s tempting to say Matt’s explanation is just dishonest, but what about the predictable impact on customers and shareholders? A boycott against GrubHub is now organized which is on Twitter’s trending list at #boycottgrubhub. Upon regaining composure after reading the email today, I tried to short the stock. Too late. It had already dropped by over 4% — $120 million of shareholder value already incinerated.


Didn’t he see the firestorm coming?  Like I said from my experience, Matt has been a good steward of shareholder money. How could he do something this stupid? I don’t think Matt would have knowingly risked the damage done for political principle.


The answer, I think, is blindness more severe than the usual charge of hypocrisy and intolerance by the left. The righteous can’t possibly be intolerant, think the anointed. We know that, but it goes beyond feeling no need for introspection of their own values. It’s so deep that it also never even occurs to them to worry whether others might perceive them to be intolerant — even when millions of dollars are on the line.


That’s what happened here and we’re seeing it frequently, especially in the press. Most Americans now say they know the media have exaggerated Trump’s rhetoric and flaws (though I’m not defending him here). For the press, it’s the same question as for Matt: How can they be so stupid as to insult so many of their own readers?


You’d think this would have ended with the election. “Hey, wait a minute, maybe it’s possible almost half of Americans aren’t bigoted, uneducated hayseeds from the Midwest”  — you’d think that would have occurred to them.


Nope, not yet.


UPDATE 11/12/16: Matt appears to be doubling down on his claim that his original statement, and his subsequent one, are just about tolerance. He has tweeted, “I ask anyone who is inspired by my message to RT this and counter the headlines compounding hate” and “The headlines are not in line with my words.” Good luck with that. The statements are linked here. Read them yourselves and decide.

Also, there has been plenty of comment on the internet about his sale of stock on Nov. 7, prior to sending the email. This does not appear to be a big deal to me. The sale was for about 15,000 shares but he retained about a million, according to the SEC form filed.


*Mark Glennon is founder of WirePoints. Opinions expressed are his own.



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So…too bad you didn’t know about the letter before the CEO wrote it so
you could short the stock. You know who did know? Matt Maloney. He sold
almost all the stock he owned in the company the Monday before the election.

Here is the SEC form 4 he filed…

So I wonder when he is going to buy it back.


Regardless of his intentions or blindness regarding the email to employees, here is his public Tweet from September: “@grubhub diners skew urban, female, and intelligent…all characteristics trump supporters lack.” Hard to imagine a worse idea than a CEO of a consumer-facing company saying this publicly about 60M consumers. Where is the Board? How have they not acted?

Karl Kolchak

I just deleted the GrubHub icon from my phone and will never use this awful company again–and I was a Sanders supporter. This guy represents everything that is wrong with America–big money in the hands of arrogant, intolerant nitwits.


“It’s about how an exceptionally bright person can be exceptionally blind to the certainty of self-inflicted harm.”

Exceptionally bright?

This Maloney guy reminds me of my Irish-born grandfather’s oft-repeated observation; “There’s nothing thicker than a thick mick.”


Whenever I see anyone make blanket generalizations about “the right” or “the left” in any context, it tells me they have abandoned discourse and only seek to prosthelytize to an echo chamber. It disturbs me when any individual, either the author of this post or the author of that email, can engage themselves in such incredible petulance.


I couldn’t disagree with you more Mark. There are many, many people of color in America who are feelilng scared right now, and rightfully so. Matt’s statement is an example I hope to see more leaders following, especially in the technology sector where immigrants make up a large portion of the employees. I especially found this powerful: “I want to affirm to anyone on our team that is scared or feels personally exposed, that I and everyone else here at Grubhub will fight for your dignity and your right to make a better life for yourself and your family here in the United States”, is

Hey Nick, I’m one of only 25k Trump voters in San Francisco. Right now my city (and the neighboring city of Oakland, and, ironically, Chicago!) is targeting people who voted Trump – and people who, to them, look like Trump voters (that is, white and male) with abuse, vitriol, and violence. I’m currently in a coffee shop in Russian Hill where two women are loudly proclaiming they would kill people like me. What have I done to deserve this opprobrium besides exercising my right to vote for the candidate I feel is better / least bad? Why should people of color have a monopoly on the right… Read more »

I did not put a Trump sign in my yard
Because I am a deplorable
That lives in Chicago
Such a sign
would put me and my family at risk .


You should not have to feel afraid. Those people, many people, are misbehaving. Trump, however, represents canonized hatred at the highest level of our government. There is a big difference in the narrative threads here.


Does he? I have yet to see what I would describe as “hatred” coming from anyone but the folks out here threatening (with arguable plausibility, to be sure) to kill me.

John C.

This pr1ck is going to jail one way or another. He shorted his own stock a few days before sending this email.


“Most Americans now say they know the media have exaggerated Trump’s rhetoric and flaws (though I’m not defending him here).”

The fact that you felt compelled to add this parenthetical, which has absolutely nothing to do with your article, speaks volumes about the problem that the left still doesn’t understand.


I am boycotting grub hub
This deplorable is still boycotting target …. And now grub hub,,,,
Silent majority no more, piss on grub hub

Never Trump

So what, I support it.


Great inside baseball article. Keep it coming.


It apparently has not occurred to Mr. Maloney, as a Hillary supporter, that Hillary’s conduct and views were so offensive to some people, they viewed Trump, with all his flaws, as the better choice.
He listed many of Trumps flaws in his letter.
No Clinton flaws.
So his view is ones sided.
And, that is a powerful indictment against the candidate he supports.


What if you’re a Grubhub employee and disagree with Rahm’s “hateful politics” in the Laquan McDonald shooting? Shouldn’t you also hand in your resignation? Because Maloney contributed $50,000 towards Rahm’s campaign after the incident. So using his same trumpified logic, Maloney supports police brutality of young black men.