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Re:7 Rejections by tptacek on Sunday July 12, 2015 @03:47PM (#9874665)
How did they get such clear "No" answers?

That list of rejections was very, very unlike my experience trying to raise VC, which was more like 7-10 VC firms giving meaningless "yes, soon!" responses until we gave up.

Re:7 Rejections by paul on Sunday July 12, 2015 @06:23PM (#9875259)
They said "no" because they didn't want to waste time meeting with such an obviously unpromising startup :)

I was one of the angels who simply didn't respond, in part because I was busy with my own startup, but also because the idea of a marketplace for renting out air mattresses just didn't sound very appealing...

Re:7 Rejections by tptacek on Sunday July 12, 2015 @07:23PM (#9875422)
Then let me reframe the question:

"How would I go about presenting my company in such a way that it'd seem so unpromising that only smart investors would give me the time of day?"

It feels like maybe there's an "uncanny valley" between "no plausible way this team is getting funded speculatively" and "no-brainer straight- to- partner- meeting".

Re:7 Rejections by ericabiz on Sunday July 12, 2015 @07:35PM (#9875455)
Simple answer: Only take meetings with VC firms and angels who have direct experience in the area where your product helps the most.

I mentioned to you in a reply, below, that my marketing software company got immediate YESes from angels who had been leaders of marketing teams and intuitively understood the need for our software. I think my record time to close an angel was under 2 minutes. For those who had never led or been part of a marketing team, it was an uphill battle the entire way.

Once I learned that filter, I was able to raise money more quickly, with much higher close ratio.

Re:7 Rejections by paul on Monday July 13, 2015 @08:22PM (#9882083)
I doubt it's possible. Keep in mind that nobody invested in AirBnb until YC, and as I understand it, they were mainly accepted based on the strength of the team.
Re:7 Rejections by mbesto on Sunday July 12, 2015 @07:49PM (#9875511)
I've pitched to 30+ investors and got rejected....a lot. Here's my generalized conclusion: VC funding is like dating. Easy money goes for the hot sexy blonde at the corner of the bar in the west village, but it doesn't mean the slightly less attractive brunette sitting in the corner isn't the best catch. No one would dare miss out hitting on the blonde, and no one is going to fault anyone for not hitting on the brunette "she's uninteresting". My only advice is to understand first what the investors' thesis is and play your pitch to those strengths. For example - what markets, what they look for in teams, and what their fund's goal is. I've had a fair share of VC's be brutally honest with me on the last point with an answer of "we need just one billion dollar business in order to return our fund, so we take as many bets as we can to ensure we get one".
Re:7 Rejections by learnstats2 on Monday July 13, 2015 @05:26AM (#9877102)
You could easily have made this point without degrading women.
Re:7 Rejections by IanDrake on Monday July 13, 2015 @10:00AM (#9878081)
Well, you got that completely wrong. What would have been correct is:

"You could easily have made this point without degrading men."

In his story he generalizes men as playing the fool and makes no generalization about women.

Re:7 Rejections by IanDrake on Tuesday July 14, 2015 @08:18AM (#9884260)
Yikes! To correct my straight bias:

There was no generalization made at all. He never made reference to gender of the person walking into the bar. It could have been a woman walking into a gay bar.

My apologies.

Re:7 Rejections by learnstats2 on Tuesday July 14, 2015 @11:13AM (#9885505)
If you wanted to tie yourself in knots, you are succeeding.

The degradation that I saw was that, in the analogy, women are sexually objectified. Women appear in the story exclusively in a sexual context, where there is no good reason for that. The context makes it clear that this is normal and expected within the (male) OP's world.

"No one would dare miss out hitting on the blonde". There is a clear generalization here, that everyone should find blonde women most attractive, or at least be socially required to act as though they do. Perhaps women are also expected to find the blonde woman most attractive, or perhaps women's opinions aren't really worth considering.

You might re-examine your own gender and sexuality biases in this context.

Re:7 Rejections by IanDrake on Tuesday July 14, 2015 @01:04PM (#9886369)
>If you wanted to tie yourself in knots, you are succeeding.

I'm actually being sardonic. The political correctness police are a bit tiresome. My point is that, if one wishes, they can analyze any statement to be as sexist, racist, homophobic, etc... Including yours.

>The degradation that I saw was that, in the analogy, women are sexually objectified

If women are 'sexually objectified' by other women is it a problem?

Why did you overlook the completely racist message in his analogy? Assuming most men prefer blonds assumes white culture, which is racist since I doubt black and asian men feel the same. I don't know, maybe I'm racist for doubting that assumption?

Also if a character's gender isn't identified in a story, is it sexist to assume that character's gender is the same as the storyteller? I was guilty of that one too.

This where the P.C. police trip over their own logic and fall into the pile of B.S. they've created.

Re:7 Rejections by tptacek on Monday July 13, 2015 @01:59PM (#9879798)
This really seems like a case where the downvote button could have done a better job than angry discussion.
[dead]
Re:7 Rejections by wglb on Sunday July 12, 2015 @11:08PM (#9876159)
Not an appropriate comment for HN.
Re:7 Rejections by sitkack on Monday July 13, 2015 @12:22AM (#9876377)
Are you addressing me or the OP? Apparently sexiest brogrammer comments are ok. What isn't ok is a silent tacit approval.

"Yeah, sexy blonde, totally makes it clear for me. Thanks for putting it into terms I can understand."

Re:7 Rejections by tptacek on Monday July 13, 2015 @12:26AM (#9876395)
If you had said that, he wouldn't have remarked about your comment. But that's not what you said.
Re:7 Rejections by sitkack on Monday July 13, 2015 @12:41AM (#9876451)
Complaints of color over content, sometimes color is part of the content. Sometimes civility of the response downplays the visceral nature of the reaction. I revile at it, the revulsion needs to be expressed. My four words expressed my sentiments in the most correct and compact manner.
Re:7 Rejections by thaumaturgy on Monday July 13, 2015 @01:36AM (#9876598)
It didn't work.
Re:7 Rejections by lubesGordi on Monday July 13, 2015 @12:38PM (#9879198)
It's interesting to me that VC's would look at this and not immediately think of an easier to monetize version of couchsurfing, which was already very popular at the time.
Re:7 Rejections by applecore on Sunday July 12, 2015 @06:40PM (#9875307)
Note that one firm smartly left their free option open to invest in the company post-Series A.
Re:7 Rejections by teej on Sunday July 12, 2015 @06:50PM (#9875339)
This is a very standard "No" response from a VC. There isn't anything exceptional or strategic about it.
Re:7 Rejections by staunch on Sunday July 12, 2015 @05:35PM (#9875069)
It's likely that Paul Graham directly and enthusiastically introduced them to the VCs, which obliged them to respond with a semi-coherent rejection. That's what the Fred Wilson rejection was like anyway: http://www.paulgraham.com/airbnb.html
Re:7 Rejections by dang on Sunday July 12, 2015 @05:55PM (#9875137)
This was before that. Interviews for W09 were in November 2008 IIRC.
Re:7 Rejections by staunch on Sunday July 12, 2015 @06:04PM (#9875174)
You're right. That makes a lot more sense, especially the $1.5M valuation. I missed the first line about Michael Siebel introducing them. Given his YC affiliation, it probably had a similar effect.
Re:7 Rejections by vlad on Sunday July 12, 2015 @06:44PM (#9875319)
I think that's also wrong. Michael wasn't a YC partner at the time; he joined Justin.tv as CEO after Justin and Emmett got into YC again after selling their calendar app to Tucows or similar on eBay.
Re:7 Rejections by staunch on Sunday July 12, 2015 @06:54PM (#9875345)
I did not say partner. He was a YC founder for years prior. He got Airbnb their YC interview. Let's drop this really boring thread ;-P
Re:7 Rejections by tekacs on Sunday July 12, 2015 @03:54PM (#9874691)
Perhaps because their rejections were seemingly policy-driven ('we don't handle/haven't had luck with this category') rather than qualitative?

I've heard the same happen to friends attempting to seek investment in 'music' and 'gaming' businesses - clear rejections based upon their 'category'.

Re:7 Rejections by paul on Sunday July 12, 2015 @06:17PM (#9875230)
It's mainly an easy/polite way of saying no. If they knew it was going to be huge, all would have invested.
Re:7 Rejections by lmm on Monday July 13, 2015 @06:42AM (#9877286)
Sure, but the point is that as a startup I'd like to get a clear, unambiguous no when they're not going to invest, rather than a "yes, maybe, soon..."
Re:7 Rejections by curiousjorge on Sunday July 12, 2015 @04:12PM (#9874771)
This is probably the safest way to reject someone seeing that 4 of them used the exact same response as well as your music business investors. I hear this line all the time.

To be fair, I guess making huge returns is not their prime policy or maybe their investors have a policy against certain investments due to moral or some esoteric reasons.

Re:7 Rejections by tptacek on Sunday July 12, 2015 @04:24PM (#9874823)
The VCs we talked to weren't not rejecting us so they could save our feelings. They were doing it because we were offering them a free option on our business.
Re:7 Rejections by tekacs on Sunday July 12, 2015 @04:21PM (#9874814)
A common-enough rhetoric in discussion with folks from VCs does definitely seem to involve the 'areas they are currently interested in'. A sibling comment to mine bears this out slightly with the 'security is not our sweet spot' response.

You cite esoterica, but perhaps investors just feel more comfortable with certain areas - or ones they have the in-house experience to evaluate properly - or that are easier for junior partners to sell to the folks higher-up?

Re:7 Rejections by curiousjorge on Sunday July 12, 2015 @04:36PM (#9874870)
I don't know much about VC but I thought taking risks was the name of the game? Isn't that what "venture" in VC mean?

I'd understand if this was Ontario Teachers Pension Fund or something like that where a large amount of capital had to move around to generate some sizable returns. Even these money managers are scrutinized for bad decisions.

The whole 'not our area of focus' seems to be the same line mutual fund managers use during report card season by writing off bad picks and claiming they beat the market.

Re:7 Rejections by bigtunacan on Sunday July 12, 2015 @05:11PM (#9874988)
It's about taking educated risks to the best of their ability. Otherwise there are a lot of people selling bridges...

This advice comes straight from the oracle of Omaha himself, "Never invest in a business you can't understand."

Re:7 Rejections by tekacs on Sunday July 12, 2015 @04:59PM (#9874947)
I'm passing on rather than defending their behaviour.

Having said that, there's perhaps something to be said for picking one's battles?

Indiscriminately attempting to capitalise on any lucrative opportunity seems like a common road to ruin (feature creep, startups that put everything in scope, https://xkcd.com/793/).

Re:7 Rejections by curiousjorge on Sunday July 12, 2015 @05:19PM (#9875011)
While that makes sense for established markets like the stock market, I don't think the same can be applied to the early stage tech market or reading into fundamentals. Certainly trying to capture all opportunity in the stock market can lead to mediocrity (over diversification) but when one bet can produce returns that more than makes up for all the other tiny bets, hard to fathom why that isn't a much more attractive strategy.

For example, make 1% stake bets stretched across 100 startups vs 20% stake bets stretched across only 5 startups I "understand" or feel comfortable with. Isn't the risk inherently bigger if you chose the latter? If one of those 100 startups end up producing low to mid 5 digit ROI, shouldn't that cover for the 99 other bad bets? The probability increases since you are not introducing any personal biases and exposed to more upside potentials.

Re:7 Rejections by scardine on Sunday July 12, 2015 @06:57PM (#9875350)
Last time I checked the name of the game was making more than 100 times the amount invested in less than 5 years - taking risks is a unavoidable side effect.
Re:7 Rejections by serve_yay on Sunday July 12, 2015 @06:04PM (#9875172)
Sounds like the old searching for your keys under the street-lamp because that's where the light is.
Re:7 Rejections by kevinmobrien on Sunday July 12, 2015 @04:17PM (#9874793)
One of the frustrating things about early-stage in my experience is that there is little correlation between VC and market interest; our experience (also cybersecurity) has been that we're generating a significant amount of interest from (now) customers and prospects, but VCs tend to say either "we just can't get to conviction, not sure why" or "you're amazing, everything makes sense, but security isn't our sweet spot".

So far, angel investors have been much easier to work with, although admittedly we chose to focus on customer growth once we had that first round of disappointing VC results.

I think, per the other comments, your background makes a difference (assuming you're talking post-Matasano) in how the message was delivered.

Re:7 Rejections by lpolovets on Sunday July 12, 2015 @04:38PM (#9874876)
(I'm a VC.)

I think a lot of VCs explicitly (or at least implicitly) prescribe to Warren Buffet's advice of only investing in things they understand. So if you talk to a VC focused on security, they're much more likely to invest than a VC who is kind of interested in security but has never invested in it. That VC, in turn, is more likely to invest than someone who is not particularly interested in security. If an investor really likes marketplaces or security companies or B2B SaaS or whatever, there are enough great companies in each of those segments to make it okay to ignore the other segments.

It's also valuable to remember that partners at larger VC firms often lead 1-2 investments per year. Their performance is determined by the 3-5 decisions they make during a VC fund's life. It's hard to stake 20% of your performance on something you feel like you don't fully understand.

Angels and smaller seed funds are sometimes easier to work with because the former are motivated by more than financial returns and don't have their salaries/jobs at stake with each decision, while the latter make a lot more investments per partner.

Re:7 Rejections by tlogan on Sunday July 12, 2015 @05:53PM (#9875128)
> I think a lot of VCs explicitly (or at least implicitly) prescribe

> to Warren Buffet's advice of only investing in things they

> understand.

This is very very true.

And entrepreneurs MUST not take money from VCs who do not understand the market. Sadly sometimes VCs think they do know but they actually don't know what they don't know.

The worst marriage is when both entrepreneur and investor don't know what they don't know.

Re:7 Rejections by brobdingnagian on Sunday July 12, 2015 @06:33PM (#9875295)
This sounds like unsubstantiated BS. This whole thread is full of hubris.
Re:7 Rejections by kevinmobrien on Sunday July 12, 2015 @05:12PM (#9874993)
Agreed on all points, and thanks for weighing in from the VC side of the table.

For clarity's sake, I've sat on tremendously effective boards at the companies I have either run or had a senior role at, and I think there's incredible value to be had from a good VC relationship. The economic realities of raising can be frustrating, but it's a reflection on the industry rather than the individuals, I believe.

Early stage investment is just plain hard, and I think your point about the quantity of deals led is key.

Re:7 Rejections by curiousjorge on Sunday July 12, 2015 @05:09PM (#9874977)
Just from an investor/trader point of view, it's shocking that they would even subscribe to Buffet's style of investing which is suitable for non-tech stocks. There is a great deal of false confidence in an unusually high risk high rewards investment. Rather, wouldn't it make more sense to make optimize tiny bets on as much startups regardless of the industry? At the end of the day, it's not much different than investing in penny stocks or early stage mining companies, I'd find it hard to justify investing so few.

I'd subscribe to Taleb's black swan model, except the complete opposite of what he did which was making small bets that market would crash.

Capture unexpected, phenomenal returns without introducing any personal beliefs or bias and making equally sized small bets across as many startups as possible. If you can get like 60,000% ROI then the model becomes sustainable, unlimited upward potential with a limited and tiny risk.

Re:7 Rejections by blahblah3 on Sunday July 12, 2015 @08:36PM (#9875694)
if you make too many bets you'll dilute your edge. if you make too few bets then you are exposed to too much idiosyncratic risk. so people have to find the right balance
Re:7 Rejections by curiousjorge on Sunday July 12, 2015 @09:11PM (#9875809)
In a market where you just need one winner, being overdiversified argument is invalid be cause you are not optimizing for total portfolio return, you want to maximize opportunity and upwards exposure while keeping each downside risk limited. If you make too few bets the numbers are against you. Now this is nothing like spray and pray, you are still dealing with people, at the minimum you need to deal with founders who can be trusted.
Re:7 Rejections by blahblah3 on Sunday July 12, 2015 @10:21PM (#9876013)
okay but the less you allocate to your "one winner" the less your portfolio return will benefit from that winner.
Re:7 Rejections by curiousjorge on Sunday July 12, 2015 @10:31PM (#9876048)
It couldn't be worse than allocating a quarter into one company that goes under at such an early stage. the tremendous return comes when others begin buying into it, at worst case, the founder doesn't generate more money than you put in which in this case is very tiny but the equity is still sizable that the next guy paying 10x what you paid and even ipo would have exponential yield. You don't even need to focus on the startup doing well if enough series of investors are willing to buy your shares out. I reminds me of pump and dump which is why I think the latter is unethical but it's unregulated and private market, not exactly the type of people that would go homeless if the start up did go under like when Enron wiped a lot of working ordinary people's pensions.
Re:7 Rejections by ScottBurson on Monday July 13, 2015 @09:50PM (#9882372)
> Rather, wouldn't it make more sense to make optimize tiny bets on as much startups regardless of the industry?

I think I've heard of a VC firm that does that. Trying to remember the name... wait... Y-Calculator, something like that, maybe?

Re:7 Rejections by marcosdumay on Sunday July 12, 2015 @10:23PM (#9876021)
Just a question: How do you expect to create new markets or any kind of real innovation if you only invest in companies whose products are similar to something you already worked with?

Maybe it's a goof thing angels are doing bigger rounds taking your place.

Re:7 Rejections by lpolovets on Sunday July 12, 2015 @10:41PM (#9876081)
I'm an early stage VC, so I often invest at the same time as angel investors. I think there are shortcuts to getting an investment even if you are approaching a new market. Sometimes that means showing enough promise with an MVP (which often doesn't require much capital). Sometimes it's having an amazing team -- for example, a lot of early PayPal folks could probably raise money with just about any reasonable-sounding idea.

Also, investors typically invest in areas that they're familiar with, but that can be a pretty inclusive criterion. For example, I've personally worked on payment fraud detection before (as an engineer), so that makes me feel comfortable investing in fraud detection, but also credit assessment (similar algorithms), a large number of startups that involve lending or payments, and so on. For another example, my fund invested in Flexport (a recent YC company that handles shipping logistics for companies). My partners and I didn't have any personal logistics experience, BUT one of my partners worked at a company that struggled with imports and shipping, so he appreciated the pain point. Also, Flexport's CEO, Ryan, is a force of nature and had been working in the import/export space for 15 years, so he was very credible. That was enough for us to invest despite not having logistics experiences ourselves.

In the Airbnb example -- and I wasn't an investor 6 years ago so I don't know what their pitch was like -- I'm guessing if the founders had a bunch of lodging-related experience, or if they had previously built great companies, or if they had a few more data points that showed the viability of their model, that could've helped.

Finally, here's the challenge from an investor's point of view: you see 1500 pitches per year. The majority of the pitches mention something like "we're going to be a billion dollar company" or "we're going to create an entire new market." One or two of those 1500 companies will do just that, ten or twenty companies will get kind of close, and the other 99% won't be close at all. In hindsight, it's easy to look at Airbnb or Uber and think that investors were short-sighted. Maybe they were. But a lot of early stage companies look simultaneously promising and risky in their early days, and most of them fail, so investors understandable err on the side of pessimism.

Re:7 Rejections by Fede_V on Monday July 13, 2015 @04:42AM (#9877006)
Thanks for your point of view - that actually makes a lot of sense.

I really dislike the escalation of pitches. As you said, almost everyone says that 'we will become a billion dollar company' or similar claptrap - but that just means that people have to make more and more extraordinary claims to pierce the cynicism (fully justified!) of investors.

Re:7 Rejections by marcosdumay on Monday July 13, 2015 @03:02PM (#9880255)
My post turned up to be too confrontational, sorry for that.

I'm not opposed to VCs on abstract, and I'm happy to see people trying to do good work on the area. Your area is hard, and if you can improve it, everybody wins.

I also got widely off-topic, because I was complaining that todays VC wouldn't have created the Silicon Valley, not that they couldn't see Air B&B. That said, I'm still not convinced you are liberal enough to do this. (Not that you should.)

Re:7 Rejections by larrys on Sunday July 12, 2015 @05:01PM (#9874952)
"which was more like 7-10 VC firms giving meaningless "yes, soon!""

In theory by doing that they were raising the potential price for those that would end up investing. Their competitors. If you felt you had "plan b's" you'd be less likely to lower your expectations on value than you would be if you had 7 firm rejections. 7 firm rejection might mean "take what we can get".

Here is an example using car buying.

If a car is sitting on the lot and has nobody expressing any interest the dealer may possibly want to unload the car and take whatever he can get. Otoh if the dealer feels that he has 2 or 3 people interested in the same car he will then be less likely to take a "short" deal from the 4th person who walks into the dealership. He will feel there is potential and it is worth the gamble to wait feeling he has a few plan b's.

(Forget for a second whether this actually happens with car dealers I am only trying to illustrate the theory of what I call "feeling fat" which I have seen many times in business).

Of course as a group it's hard to explain why all participants would act this way or that this even happens. However I don't feel individually they are disadvantaged by this behavior at all. While there might be a reputation disadvantage to stringing someone along unless they are absolutely sure they will not invest why not string someone along?

Re:7 Rejections by lemevi on Sunday July 12, 2015 @04:04PM (#9874733)
You're kind of famous and people aren't going to want to say no to you but at the same time probably fail to execute. There's zero hesitation when it comes to shooting down small fries from my experience (I'm an employee at my 3rd ycombinator startup now). I remember Airbnb when it was tiny, back in 2009/2010, they were small like the rest of us once.
Re:7 Rejections by tptacek on Sunday July 12, 2015 @04:09PM (#9874756)
I don't think my reputation --- which is close to nonexistent among investors, who do not as a rule read HN --- had much to do with it.
Re:7 Rejections by ericabiz on Sunday July 12, 2015 @07:28PM (#9875434)
You might be surprised on that. I got many of the same style of rejections you did. I got very few clear-cut "No"s and lots of "We like what you're doing and it makes sense, but we need a bit more time." Which is the most frustrating form of "No", as I suspect you know.

My guess as to what made us different than Airbnb circa 2008--maybe some of these apply to you, too:

1) Founder with previous exit/acquisition in the tech space

2) Product had some traction (paying customers, including a F500 company)

3) Product was in a domain that most VC's/angels didn't have experience with (in my case, software designed for marketing teams) -- some were nice enough to outright reject us based on the fact that they had never been in marketing; the people who had previously been in marketing almost immediately saw the need and said "YES" right away; many of them saw that we had traction but felt like they needed to understand the market better to see what we were seeing, so to speak.

Re:7 Rejections by pyb on Sunday July 12, 2015 @04:48PM (#9874903)
Maybe because the investors were 100% sure they wouldn't invest. In other words they find it easier to send out a response when a dossier is the "definite pass" pile ?
Re:7 Rejections by prostoalex on Sunday July 12, 2015 @09:59PM (#9875953)
He didn't publish the other 93 "yes, soon!" emails.
Re:7 Rejections by shin_lao on Monday July 13, 2015 @02:10AM (#9876689)
When we raised money, I most of the time had a clear "no" as well. We also had a couple of "no answer", but that was rather the exception.