Dave McClure, 500 Startups, & Founders: Taking Advantage & Arbitrage of Other Investors

Dave McClure is a greedy venture capitalist & founding partner at 500 Startups, an internet startup seed fund and incubator program in Mountain View, CA. He likes to hang out with entrepreneurs, and occasionally help or invest in their startups if they are foolish enough to let him.  Dave has been geeking out in Silicon Valley for over twenty years, and has worked with companies such as PayPal, Mint, Founders Fund, Facebook, LinkedIn, SlideShare, Twilio, Simply Hired, O'Reilly Media, Intel, & Microsoft. Years ago he used to do real work like coding or marketing or running conferences, but these days he mostly does useless stuff like sending lots of email, blogging, and hanging out on Facebook and Twitter. Dave also likes to play ultimate frisbee when his knees don't hurt.  You can find Dave @his blog Master of 500 Hats & on Twitter @davemcclure.

Jennifer Chin & Elizabeth Yin are CoFounders of Launchbit.

Jennifer is a graphic and web designer, who in the last 15 years has developed graphics and frontend user interfaces for startups, athletes, universities, orchestras, and of course for her own sites. She holds a B.A. in Chemistry and Physics from Harvard and a Ph.D from MIT in Materials Science.

Elizabeth is an internet marketer and backend programmer, who has done marketing for startups and was a marketing manager at Google. Prior to becoming a marketer, she wrote code for startups during the dot com era and holds a B.S. in Electrical Engineering from Stanford and an MBA from MIT Sloan.

You can find them on their blog & on Twitter

As Chief Executive Officer of khu.sh, Prerna Gupta brings extensive experience in social media product management and viral marketing to the Khush team. She previously founded Yaari, an Indian dating site which grew to over 2 million members. Prerna studied Economics and Computer Science at Stanford University and worked on marketing strategy at Monitor Group and early-stage deal sourcing at Summit Partners before making the move to entrepreneurship. Her favorite instrument is her voice. You can find Prerna on her blog & on Twitter @prernagupta

Don't forget to read Part II of the interview here.

Pemo: Thank you all for coming today & really appreciate speaking to you. I just wondered Dave particularly, you're sort of the center of the universe here @500Startups.

Dave: That really is exactly the opposite of the goal!

Pemo: OK but you do have a great number of female founders.  I've much admired that & I know there's a lot of female entrepreneurs out there that do think that's fantastic!  So just wondered what your goal & motivation is around women startups.  Do you specifically look for them.  What is it that makes you want to invest in a woman founder?

Dave: Do I specifically look for women or women startups? (Is my wife watching this?) We don't have an explicit goal. I think it's still a minority in the portfolio. It's probably around somewhere between 12 & 15% of the overall portfolio. Sorry women CEOs is probably 12 to 15% out of the portfolio.  Women Founders or CoFounders is probably 20 to 25% of the portfolio maybe?

Pemo: So that's a little bit higher than most people that I've interviewed.

Dave: Yes I think that's substantially higher than most.

Pemo: So why do you think that you've managed to attract so many female founders or female teams? Is it just your natural charisma? (Laughter...)

Dave: Yes well really they should be aiming a lot higher!  I think it's probably the other way around.  Why do we invest in women?  I think it's just the case that we don't not invest in women which I think is the operative thing that's going on with the rest of the industry. My Mom was a single woman entrepreneur.  A lot of my friends are women entrepreneurs so it sorta has not been an unusual thing in my life for work experience. I don't know that there's a huge amount of bias in the industry.  I think there's probably some.  I don't think that it's so tremendous. 

In Silicon Valley at least there's not so much gender bias that I think it's an insurmountable issue. In other countries or other regions it may be more of an issue. Or for people from other types of economic backgrounds maybe?  I don't think we face that on a daily basis in Silicon Valley, at least not these days.  That's my read on it! 

But I think that there's probably still some bias in investing in what you know.  A lot of vcs tend to be white males from finance & MBA backgrounds & they invest in other males from finance & MBA backgrounds.  Or they invest in nerds with glasses who come from MIT. There's nothing really biased about that than just you kind of invest in the things that you know. So for me I grew up around my Mom who was an entrepreneur, other people who were from India or from Asia or from wherever.  We have a lot of other international folks in the portfolio not just women minorities but a lot of other connections.  And it's still a minority!  We're probably still 50% white male founders & that's somewhat based on the market. But I think as we've sort of got experience with women as founders & CEOs we've gotten more comfortable with that.  Now I would say I do look for it because it's an advantage!

I think I've probably said this to a couple of people: my intent is to corner the market on awesome, smart women founders. Because there are plenty of them out there.  Right now if there is any bias whatsoever we'd like to selfishly take advantage of that. 

The other thing that's a little odd is (you can cut this out if you're not comfortable with this) I think we have 7 or 8 couples that we've invested in.

Pemo: Ahh & that's unusual too!

Dave: Very unusual! I think at least half of them are women CEO & husband CTO. Some of our more successful companies actually! You can draw all sorts of conclusions from that if you want but I'll leave it there?  Again it's something that we've not shied away from.

Pemo: And you're taking advantage of the reticence on other investor's parts?

Dave: Definitely other investors don't want to invest in couples, married or not!

I think our general perspective on anything that other people are afraid of, is an opportunity for arbitrage for us!

Pemo: And great for the entrepreneurs!

Dave: Ah well it's not always great for the entrepreneurs!  (Laughter)

Pemo: So now let's hear a bit from you guys (Prerna, khu.sh).  Do you want to tell us your story?

Prerna: Yeah I will.  I think I fall under both those categories.  I'm a female CEO & also a couple in business.  My husband is the CTO. Actually I've never heard Dave say that he sees it as an arbitrage opportunity. (Laughter) But I had that hunch!  My company actually probably has 4 red flags. I think a lot of vcs operate with red flags. 

Dave: Four? what are the others?

Prerna: They see some things that are wrong with your company.

Dave: Wait woman founder, husband & wife, music startup?

Prerna: Yes music startup & we're not local, we're based in Atlanta! He doesn't seem to operate as much on red flags.

Dave: Or I operate because of red flags? (Laughter)

Pemo: He's just a revolutionary waiting to happen!

Prerna: Well yes, he sees a lot of opportunities that I think a lot of other investors don't! It makes a lot of sense to me!

Pemo: So that's a win:win for him & win:win for you guys!  Fantastic & could you tell us briefly about your startup?

Prerna: Yeah. My startup is a music startup.  We develop intelligent music apps.  The company is called khu.sh.  Basically what intelligent music apps means is we use our official intelligence to help people make music.

We believe that everybody has the ability to express themselves creatively through music but a lot of people don't know that & a lot of people are intimidated by it. So our goal is to use technology to make that easier. 

Pemo: Fantastic.

Dave: Will we show them the app?

Prerna: Yeah

Dave: This is a song that my 4 year old recorded. It's one of my favorites.  Basically you sing into their app & it makes you sound great & also matches some music to it!  This is my daughter singing Twinkle, Twinkle Little Star unaccompanied!  So here's how it sounds accompanied.

Pemo: Oh we love it!

(Dave plays khu.sh app from his iphone)

Pemo: Wow so cute!

Dave: Pretty cool app!

Pemo: Really cool app! 

Dave: When you hear something like that, that's why I invest!

Pemo: No that's brilliant.  So tell me a bit about your startup, you guys (Jennifer & Elizabeth,Launchbit).

Elizabeth: Well our story actually goes quite a way back.  Jennifer & I are best friends from middle school & high school. We met the day before 6th grade here in the valley. We got introduced to the whole startup world through Jennifer's cousin when we went to help him out in his startup during the '90s for a few days. We didn't do anything earth shattering.  We built chairs but we were both hooked. Fast forward several, several, several years later.

Last year I had just come out of doing a startup that failed with a different friend of mine. Actually we had pitched to Dave & he did not invest.

(Laughter) For the better actually because one of the things that I learnt from that was that we didn't have any users, we didn't have a market at all. 

Pemo: So you were able to fail quickly, which apparently is a good thing!

Elizabeth: Well we were able to fail but it wasn't as quick as it should have been. (Laughter) And so after the failed startup, when Jennifer & I teamed up for me to give it a second shot.  We thought that the way I did it the first time around was wrong. Why don't we go at it from a different approach which was make sure you have a market first. So we started doing these quick web experiments in different interesting areas & betting on ones that were showing promise.  And folding our hands effectively if you will on the web experiments that were not doing well, we just canned altogether.  From that we built out a couple of profitable niche websites in a couple of different areas. But from that experience we were also talking with new web entrepreneurs about how we were doing this. Then one thing led to the next & people were asking us all these questions about how we did this.

So we said, maybe we can build out tools to help new web entrepreneurs make sure that they have a market, validate their market.  So that's what we did with LaunchBit.

Pemo: How amazing! So you've sort of used your failure as a start of a new business.

Elizabeth: It's helped us figure out how do you find out if you have a market quickly!

Pemo: Yeah, yeah fantastic!  What's the name of your startup?

Elizabeth: It's called LaunchBit: launching bit by bit!

Thanks to Alexander Blu for music 'Concert'

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