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What I learned from raising venture capital (gabrielweinberg.com)
211 points by danthompson on Oct 24, 2011 | hide | past | web | favorite | 30 comments

This is good. As someone who's watched this process many times, I can tell you he learned pretty much everything there is to learn about raising VC the first time through.

The only thing that could make his advice inaccurate is that he was raising money for such a good startup. And in particular, one with traction. As he points out, traction trumps everything. So this is essentially a report on what it was like to travel through VC land in the express lane. The scary thing is, even then it took 4 months. It might have gone faster if he'd been on the west coast, but it still would have been a big time suck.

What are the biggest factors that increase the time suck? Amount of money you are raising, inexperience?

Conversely, what consistently decreases the amount of time spent closing a round?

The two biggest factors in the time it takes to close a VC round are how obviously good the idea is, and how much competition there is for the deal. The two are not entirely independent of course.

By "obviously good" I mean obviously good to VCs, who as a rule tend to overlook the very best ideas because they seem crazy. So for example it may have slowed things down for Gabriel that he was working on a new search engine, because to many VCs it would seem crazy to try to compete with Google.

It is crazy to compete with google

But crazy is good when combined with a good entrepreneur and some traction

I am always extremely impressed by Gabriel Weinberg's honesty and transparency. He's literally not "selling anything" here. This is just a gift to his fellow entrepreneurs.

Well, he is advertising his company. Like HN, it's a marketing activity, but one that also has a value-creation component, not merely an attention-grab.

That doesn't look or fell like advertisement. An ad would be something like "How we bootstrap our way to 7M searches per month"

That's part of the beauty.

RE: Congratulations. My wife is a musician, and back in the day,when record labels mattered, many musicians would focus almost entirely on getting the record deal. That was the thing, to get the deal. Sure, there would be stories about artist X or Y who's album had been shelved by the label or the signed artist losing of control over who would be the producer etc. but primarily it was considered a sign that you had made it, you were legit. You just didn't really consider the loss of control that went along with the 'deal'. I think the same is true with funding. Yes, you are making an exchange - money for equity. However, you are also signaling that you are legit, to outsiders and to yourself. Of course, there is a cost to everything, and if entrepreneurs are not treating the funding as a sub-goal, but rather as the goal,then you wind up with organizations that are optimized to get funding rather building customers/long term profits.

I hope you guys are working on a pro-privacy email service

How much did he raise again? He says he didn't get meetings until after the August vacation period. And announced the funding October 13th. Does it really only take 6 weeks to put together a multi-million (?) dollar round?

I didn't say, but it was 3M.

As for August, I did get meetings before, it just caused trouble because some meetings I couldn't get before, or there would be large period between meetings, which hurts momentum. And that all adds up to it being harder to align the time-line across multiple firms.

No, it takes all the work before you ever talk to an investor plus a certain amount of time which for him could have between six weeks given the traction of DDG.

Not really the point I was trying to make, but thanks?

Hi epi0Bauqu! Congrats!

That being said, is it possible to see the actual six slides deck ?


Thx! I thought about that a bit, but am not comfortable with sharing it yet.

Thanks for your article, for someone outside of Europe it helps a lot to get insight on the process in the US. Ironically, albeit a super interesting write, it's your link to why it doesn't feel right that got my attention! Good luck for the rest :-) good things come to those who work hard !

IF Gabriel is reading this: How did you meet the VCs/Angels you already knew?

--Angels mainly through angel investing myself, which I realize most people cannot do.

--Entrepreneurs who have been funded before from going to events and getting intros through other people over the years.

--I really didn't know many VCs. I met a few through entrepreneurship events in Philly. One through an angel friend a while back. And one I worked for 10 years ago.

Would you say that doing an angel investment (with no prior experience and no ties into the angel community) is a hard or risky thing to do? I've been considering trying it, but basically don't know where to start...

Assuming you know what you're doing or have a sense for what you believe the payout profile to be like, here's some metrics of the payout for N deals.

If you're at all risk averse, you probably want a percentile more like the 10th percentile payout, but this shows 50th percentile.


This is a detailed topic, but basically you have to expect to lose all your money, and if you want to be serious about it (with a better expected value) you have to do a lot of deals over a long period of time.

That being said, you have to start somewhere, and the best way to do that is to co-invest with people. I would meet local angels and hook up with them.

OK, co-investing makes sense. And by "risky" I meant more of losing time and nerve cells rather than money (which is an inherent risk), but I guess these are connected.

Well not necessarily. A lot of people are completely passive. They write checks and never look back. I'm way more high touch and like to be involved, and so the time constraints are more significant.

dontbubble.us link is broken - it sends you to donbubble.us

Thank you -- fixed.

if Gabriel had so much trouble, I can just imagine how tough the process is for everyone else.

Thanks Gabriel, this is great.

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