My wacky idea:  Put stuff on Ebay and use the money to fund the progressive blogosphere.  All of us have tons of things that we could do without.  Looking around my house, I've got at least $1000 worth of stuff I wouldn't miss if it disappeared tomorrow morning.   If we could figure out the mechanics and logistics of this scheme, I think we could generate serious $$.

Whenever a blog asks for donations, I always wish they'd just sell stock in their operations.

They'd get more money (to buy new equipment, hire sales and marketing staff, expand into other mediums, etc.) and all the visitors who buy stock would have a stake in the blog's success.

It would also be more transparent than the current system.

However, that seems unlikely.

Perhaps you can set up something similar to a mutual fund for progressive businesses. The stockholders would vote on board members who would decide which businesses to invest in.

I guess it would be similar to current "socially conscious" mutual funds, but would provide start up money versus making stock purchases.

Not sure you'd have to train entreprenuers. They're probably already there, but just can't get funding.

This is a very important discussion to have.  I want to dive in.  I don't think your bullet points are correct, however.  I think they profoundly misunderstand what the problem is.  Allow me to offer a blunt assessment from the perspective of a 25 year old outsider.  The kind of asshole you might want to have as one of your progressive entrepreneurs.  

The number one problem that faces your movement is that most of the people who are sympathetic to your ideas could give a shit about reading blogs or participating in your discussions or really, anything that has anything to do with you guys.  People my age are much more likely to support progressive ideals then people in any other age group.  We know this from many polls and studies.  We also know that people my age aren't the ones connecting with the best progressives have to offer.  For example, even though TPM media is, in tone and politics, very much in sync with young peoples beliefs and values, most readers of TPM are older.  Josh had a post today talking about how most of his readers are about his age (38).  The progressive movement is failing to connect with it's most sympathetic constituency.   The problem isn't creation of new stuff, but connecting that new stuff to the people who will be influenced by it.

The problem, therefore, isn't a lack of ideas or entrepreneurial spirit.  On the contrary, many websites, like Kos, demonstrate such a spirit.  AmericaBlog just raised 20,000$ to give it a go.  These guys are laying the groundwork for the next 20 or 30 years.  TPM Media is doing quite well.  Encouraging too much entrepreneurial energy might divide the pie into too many slices, so that no one visionary can get enough to get off the ground.  We'd be much better off with a Josh Marshall and a Kos going full gear then we would be with 20 Josh Marshall's and 20 Kos's going in 2nd gear.  It very quickly becomes a problem of economies of scale.  Larger organizations can get things done that smaller ones can't.  The converse is also true, but we're at a point where the biggest problem isn't a lack of entrepreneurial energy, but that economies of scale aren't being captured, and that other parts of a business model aren't being addressed.

A couple examples of that.  Of the blogs I've read, I've had to sign up to post comments at least 20 times.  This quickly becomes incredibly annoying, and who wants to grind out 20 registrations when they could be watching skateboarding dogs on YouTube or having cybersex with 55 year old men posting as 19 year old porn stars on MySpace?  It would be much better for the movement to design and create a method for eliminating this annoyance, and other similar annoyances (I can think of several off the top of my head) like it, than it would be to create 3 or 4 Kos clones.  Even better would be the design and implementation of a method to artfully and seamlessly integrate progressive content into the sources people already use.  This, however, wouldn't be progressive entrepreneurship, but technological and design entrepreneurship, and would have many implications beyond politics.

Another example of progressive failure in capturing economies of scale is in regards to advertising.  Both candidates and the blogosphere do a horrible horrible job marketing.  Really awful.  I'm talking an F in marketing 301 bad.  I'm talking I'm Big Fat Crazy Jim and I'm going to save you money on carpeting because I'm crrraazzyyy! obviously shot in one take bad.  I'm glad progressive people reject most values that go into advertising and marketing, but they really shoot themselves in the foot over and over on this.  For example, the terms blogosphere, blogs, and bloggers are incredibly off-putting to anyone with any aesthetic sense at all, or anyone who's the least bit technophobic.  Even the idiots who marketed the zune could come up with better.  Speaking of idiots, the same people also get all the contracts for political ads, regardless of success, which involve almost no creativity at all, and mostly depend on an incestuous network of backscratching also contribute to progressive problems.  They would be fired from the business world for their lack of results.  A marketing genius who could re-brand and devise an effective marketing framework for the existing progressive entrepreneurs, targeted towards long term growth among sympathetic constituencies, is going to do a lost more for progressive politics and to address progressive deficiencies, then another young progressive entrepreneur.  In this case, a young entrepreneur isn't who you want.  You want a marketing genius, like the people who did the iPhone launch, for example.  Trying to replicate this kind of success from the ground up is not as cost effective as simply hiring the people who know what they are doing already and empowering them.

In other words, I think that the conversation in bullet point 1 is going to lead us away from the types of set ups in the other bullet points (with a few exceptions).  You can't really decide what needs to get done as far as efficiently distributing money and resources until you have the discussion in your first bullet point.  What you write is like me saying "I need to have a discussion about what's wrong with my house and get an electrician in here right away and figure out what the best way for him to get into a wall is."  Well, you don't know that the electrician is what you need until you've had that discussion.  I think the discussion will show that the problem isn't a lack of entrepreneurial spirit or support for said.

This doesn't mean there isn't a lot of frustrated would be liberal entrepreneurs who would like your support.  It just means that supporting them isn't what gets the job done in the long run.  Let them fight it out in the wild, and when the best of them succeed, let's have other stuff in place to support them.  Much better then coddling a few of em and neglecting the other stuff.

I think the best way to start this discussion is to figure out what questions we should discuss.  We should open with a meta-discussion of the discussion, about what the problems facing our movement are.  Once we've established what our problems are, we should look for commonalities, and places where we can kill more then 1 bird with 1 stone, and ask experts in the fields related to where we think we have problems for advice, and incorporate that into our discussions on how to grow and push around resources.  At this point in time, I think we should regard your objectives about increasing entrepreneurship as an open question, rather then as settled.  If promoting progressive goals and promoting progressive entrepreneurship are contradictory, or if promoting entrepreneurship isn't the most cost effective way to promote our goals, we gotta choose to promote the goals.

You're getting the cart in front of the horse a bit in setting up the discussion, I fear.

I read it all.  Very very very nice.  You have indeed thought about all the issues I wrote.  Great work.  In particular, you are right about building infrastructure as being a much better use of political $ then donating to candidates.

Personally, I have decided to donate 20$ to infrastructure building causes (which I agree is a much better use of money) every pay period.  This month, I gave the AmericaBlogs drive, and next I have already decided to give $ to TPM, but I'm putting you guys on my list for sure.  It's not much, but I'm not rich.

Now I will pitch an idea or two.

In order to have these discussions be most in line with reality, we are going to need to do some fact finding, gathering, and organizing, to make the discussions reflective of the latest knowledge available to us.  For example, if we are going to talk about conservative media, we should have demographic information in hand, like what is the demographic of the viewers, what is their religiosity, income, etc.  What other media do they consume?  In what other historical contexts have similar obstacles been overcome?  Etc.  This might suggest a roadmap would be helpful.  For example, if we knew that in 2 weeks we were planning to discuss conservative media, we could get a couple people on some research to inform that discussion before it starts.  Then, that information could be laid out along with the discussion post.  In addition, you could invite members of academia, politics, and, most importantly, business, to participate in helping analyze the data relevant to the questions.  Announce a discussion topic, and create a post as a research dump, and recruit the A-class professionals to pitch in with the analysis.  Then, when it rolls around to discussion time, the research and some analysis is already done.  We could then invite high ranking people in blogs (grr) relevant to the topic to contribute their thoughts, so that the expertise of the, um, experts connects with the movers and shakers in the, um, blogosphere (grr).  For example, if we are having a discussion about framing security issues for progressive politicians, we could have a bunch of quotes, facts, speeches and poll results rounded up, and then consult with Bruce Schneier (tech security guru) and some Lakoffian scholar good at framing issues.  Then, with our research and experts ready for our discussion, we could invite the progressive bloggers who talk about foreign policy as well.  For example, Kevin Drum is a well known blogger who talks a lot about foreign policy and security from a progressive position.  He is also somewhat stupid about both framing and security.  His writing would be improved by connecting with the data and the experts opinions.

It would be much better for these discussions to have low but influential readership and participation.  I recently said to the guy who runs ornicus that his blog was like the velvet underground, in that there weren't to many fans, but the fans he did have were very influential.  That might also be a model for these discussions.

Also, I would suggest a re-branding effort before undertaking this.  "Planting Liberally" is all well and good, but it would fail you out of advertising school.  There is a reason people spend hundreds of thousands of dollars on website names and naming pharmaceuticals, since it has such a huge effect.  Being liberal about where we want to plant resources is the last thing we want to do.  What you have is kind of like a burger joint called "The Mad Cow"

My outline, as one idea, would go like this:

1.)  Rebrand based on the latest advertising science.
2.)  Roadmap discussions, delegate research duties, and recruit experts to participate in the discusssions ahead of time
3.)  Then discuss, with prominent members of the blogosphere invited
4.)  Then, once a series of these discussions have taken place, look for common problems, or places where one solution would solve more then one problem
5.)  Roadmap, delegate, and recruit for discussions of these potentialities.
6.)  Then work on the business issues.

Great work, this is going to be great.

I talked about "giving" in the sense not just of donating, but of giving one's talents to the progressive movement.

This bit of your post shows the major problem with your concept of "liberal entrepreneurship".

Entrepreneurs are not in the business of "giving", they are in the business of making money. So the fundamental problem is simply this .... and this is the problem I am facing with my own business ... I can't run a business, pay my bills, employees and yes get rich if I am expected to give everything for free because the requester is pure of heart. This is not a business, this is not entrepreneurship, this is a charity, a non-profit foundation.

If we want "liberal entrepreneurs" then we need to  be willing to pay them and allow them to do well. And here is the hard and dirty fact -- investors will not and do not invest in business unless they can make 20x their investment. This doesn't happen unless the business can charge and make money. They depend this kind of potential return because so many business fail. Starting a business is a high-risk business.

Many progressives have the concept that doing well is somehow evil. Unless this changes, quite simply, the blogosphere and liberals in general will always be dependent on the mercy and the hand-outs of others.

Lets stop glorifying poverty as a sign of purity. As someone who has been poor, I can tell you there is nothing glorious or noble about poverty. Poverty means that your kids don't go to college. Poverty means that you don't have health care. Poverty is stress. Poverty is an early death.

What I was actually talking about is the hope that successful entrepreneurs would have both enough surplus money, and sufficient personal investment in the movement, to donate back to the movement on a regular basis.  Essentially, my argument is that entrepreneurship can create a class of relatively wealthy individuals who are personally invested in the movement, and that class would be a major boon to the movement in terms of being a base of reliable donors.

This means that in order for an liberal entrepreneur to be successful, they first have to tailor their product/service to help conservative organizations and companies be successful -- because progressive/liberal organizations are going to ask for charity. Lets stop thinking this! Because as someone who doews consider themselves a liberal entrepreneur I rather not be doing that! I didn't quit my day job a year ago to help out ExxonMobil!

... But I am not willing to take a vow of poverty. If progressive organizations cannot or will not pay a reasonable amount, then I will be forced to tailor the features and product in a way that is appealing to big companies not progressive organizations. This means features that only appeal to progressive organizations (not companies) will never get built.

There is a price for demanding that everything be discounted or free - the ecosystem is starved and what investment does flow in is not consistent and controlled by companies and those "evil" rich.

a consultant who helps large companies cooperate with unions

This example is also problematic -- such a consultant is likely to be asked how to bust a union organizing effort as well. And the consultant is looking at 2 college bills and a mortgage and weighing the money they would make vs. the opposing (progressive) side which asks for charity and results in no college education for the kids and a foreclosure.

So instead of being able to make this decision based on moral grounds - the consultant is forced to make the decision on economic grounds.

Lets take the "giving" out of the conversation and start asking people to pay. Maybe not a lot at first, but lets get money flowing through the system so people can make a decent salary.