Win the Future is a new group to "rethink" and "hack" the Democratic Party [1]. Those involved are at [2]. I'll describe how they'll fail and what they should do instead.

From the link:

Its new website will put political topics up for a vote - and the most resonant ideas will form the basis of the organization’s orthodoxy. To start, the group will query supporters on two campaigns: Whether or not they believe engineering degrees should be free to all Americans, and if they oppose lawmakers who don’t call for Trump's immediate impeachment... Participants can submit their own proposals for platform planks - and if they win enough support, primarily through likes and retweets on Twitter, they'll become part of WTF’s political DNA, too. Meanwhile, WTF plans to raise money in a bid to turn its most popular policy positions into billboard ads that will appear near airports serving Washington, D.C., ensuring that “members of Congress see it,” Pincus said... ...Adam Werbach [ex-Sierra Club president] wrote to potential WTF allies on Jan. 29. “This list is long: banning Muslims from 7 countries, green lighting the keystone and Dakota access pipeline, defunding affordable healthcare, removing all mention of climate change from the White House website. He’s moving quickly, and we need to move quickly as well.”

At least on the surface, they're engaging in a form of direct democracy, and the problems with direct democracy have been known for thousands of years. That's why we have Representatives and Senators rather than voting on bills directly. But, theirs isn't even direct democracy: it's something that only those with Twitter accounts can get involved in, that could be easily gamed, that overweights those who are popular (such as celebrities) vs those who might be less popular but better able to develop plans.

If @KatyPerry, @Cristiano, or @RealDonaldTrump tweeted an idea it'd get tens of thousands of retweets, even if were a completely stupid idea. Breitbart and AltRight leaders could easily prank the results. Howard Stern got his fans to vote for Hank the Angry Drunken Dwarf in a People Magazine poll almost twenty years ago.

In a popular vote, smart ideas tend not to do very well: they aren't as popular as quick fixes, many people can't understand them or aren't familiar with them, they can be easily undercut by those who don't want those smart ideas to succeed, and so on. That's why we have leaders: they have to come up with the best ideas and then convince others to follow their lead.

See popular voting systems for many past examples of how the Win The Future core concept has failed.

As for both of their initial ideas, both have huge problems. Why just engineering degrees? Why not medical degrees, or art history, or teaching, or mathematics? Every professional organization would pressure politicians for their own free degrees, presenting valid arguments as for why we need both art historians and engineers. A politician who sided with just giving a cutout to engineers could alienate a good part of his base, and few politicians are going to do that.

Eventually, their proposal would be to give free degrees in all fields, and then the question becomes who's going to pay for all of that. If the public is going to pay for it, then how do we determine that a university's prices are fair? How would we determine that Harvard University should get more than Kansas State University?

It's also bad public policy to favor engineering over other fields that the USA also needs. And, of course, it's self-serving for those in Silicon Valley to promote this. From their very first day, Win The Future has a vulnerability that their opponents can use against them.

The impeachment proposal isn't much better. Of course leftwing activists are going to support that, even if most Americans wouldn't. If impeachment causes Trump to leave office, then Mike Pence would take over and he'd push policies that were even more favorable to the Koch family. Whether Trump leaves office or not, not just his base but anyone who voted for him or considered voting for him would be very angry. That would result in a huge backlash against the Democratic Party. Impeachment also never means having to make valid arguments: it's a thuggish way to force your agenda and overturn the will of the voters. More on why it's a bad idea at a later date.

As for the billboards, politicians already know leftwing activists support impeachment and want free college tuition. They don't need a billboard to remind them, especially when the billboard is making threats that, except in very leftwing districts, are toothless. A billboard is also no substitute for valid arguments, and those won't fit on a billboard. It's also begging politicians to do something, and most will just ignore it.

Add all that together and the most they do is become a less popular MoveOn or join No Labels in the list of failed alternative parties.

So, what should Win The Future do instead? In brief, promote real debate about real issues. Impeachment would seek to avoid debate and would seek to silence tens of millions of people. They should move in the opposite direction and make valid arguments based on their own ideas, not the ideas of the crowd.

For a tangible example, Werbach raises the issue of Trump's Muslims ban. I accurately described how that ban would fail right after Trump released it and I offered a smart alternative. I sought help with that but, lacking the social media presence of @Cristiano, I didn't get any help. No one else made the same arguments, even though pointing out how Trump's ban would fail would have undercut him to his base and might have cost him the election. And, even though - as Trump admits - his actions regarding the ban have made the USA less safe.

Instead of making valid arguments against the ban, presenting an alternative, and using how the ban would fail to undercut Trump, anti-Trump leaders engaged in a series of less-than-useless actions such as calling Trump supporters names, thereby solidifying his base.

What those leaders should have done was tried to engage Trump in debate, asking him tough, Socratic questions designed to reveal that he hadn't thought through the impacts of his plans. For instance, several years ago I asked a low-level leader a question designed to show that she hadn't thought through the impacts of her proposals.. Those leaders could have easily done that with Trump or at least one of his proxies. They could still do that now. Even if they can't get access to Trump, they can easily get access to a Cabinet Secretary, a spokesman, a proxy, or a leading defender (e.g., @RealJeffreyLord, @ScottAdamsSays, etc.) Even if they can't get access to those people, then they can push those who do have access to ask them real questions.

A billboard against the Muslim/travel ban would have had limited impact, but discrediting someone Trump knows of over it would have sent a message directly to Trump and would have forced a change in his policies.

See the Question Authority plan for a more general discussion and dozens of sample tough questions. That also defines "tough", which probably isn't what most people are used to. See [site coming soon] for questions specifically tailored to Trump's plans. That site uses software designed to find the best questions which, as you might assume, isn't based on a popular vote.

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[1] recode · net/2017/7/3/15904484/pincus-hoffman-linkedin-zynga-clinton-win-the-future-democrats-dnc-trump
[2] Those involved include Reid Hoffman (LinkedIn), Mark Pincus (Zynga), Jeffrey Katzenberg (ex-Disney chairman), Werbach, Fred Wilson (venture capitalist) and Sunil Paul (ditto). Their Twitter: @WTFAgenda