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Fear of Flying (500hats.com)
56 points by yoseph 1636 days ago | hide | past | web | 19 comments | favorite

Does it not strike people as somewhat ironic when something like this is written by an investor, a person whose MO is to basically spread risk across a portfolio of companies instead of an entrepreneur like Elon Musk who has actually done what is described in the post time and time again?

Don't get me wrong, I really like DMC, but it strikes me as somewhat contradictory for a piece like this to be written by anyone but a person who consistently/repeatedly spreads risks a lot of what they have on bigger ventures. Once you have an exceptional network and reputation, there are few positions, besides maybe being a lawyer, that come with less risk in Silicon Valley than that of an investor.

He wasn't always an investor, and setting up a new fund/accelerator/etc. is closer to being an entrepreneur than the investor role of a random principal at a big VC.

Definitely. A 5 minute conversation with Dave will sound remarkably similar to a 5 minute conversation with other founders - he's always spread too thin, trying to raise money, figuring out the hustle, helping wherever and however he can.

Agree, however I just don't see where the fear of flying motif comes into play when you don't have all your eggs in one basket. Once a fund is raised it's typically for 10 years. There's a lot of hard steady work to do in those 10 years, but you don't really have a milestone to meet every 12-18 months otherwise you've failed and your business is over.

Actually, the milestone you have to meet every 12-18 months, in 500's case, is raising a new fund. Given their speed of investment and quantity, this is an incredibly herculean task. Definitely not easy, and very easy to fail - the failure mode here, of course, being not raising another fund. Sure, the first fund might do well, but 10 years later 500 will have failed as a VC if it has only raised one fund.

Yes and no. Is it entrepreneurship? Yes. Is it a startup in the Steve Blank sense of the word? No. It's a proven business model that works for those individuals that have a solid reputation and professional network. Is it more risk than being a partner or principal as a big VC? Yes.

Risk-wise, setting up and running your own fund is somewhere between starting a new business with an unproven business model and opting for a career path. IMHO it's not the risk profile described in this post.

The business model isn't proven - 500's idea of investing in a lot of companies and looking for lots of singles and doubles, rather than a few home runs, is unusual, unproven, and some would argue impractical. Whether that's true or not remains to be proven, but they've had some (minor) successes so far - sounds a lot like "the first few business deals" to me.

I agree with you and in your point lies my biggest beef with most investors, they talk like entrepreneurs but work like bankers. (who knows what they think like)

But I've since learnt that a certain breed of entrepreneur-investors continue to disrupt (innovate) in other ways and in other arenas. One example is 500Startup's overseas initiatives like the one in India.

Where do you think investors get the money they invest?

This is definitely a cultural thing. In discussions with the folks I'm working with (in London), failure is still the big fear. In Europe it seems, one failure marks you for life. In fact I had this exact discussion, I (Bay Area based), have definitely felt much more the fear of success. My take is that when you are afraid of success, you are probably picturing a much different version of what success is than someone who is more afraid of failure.

At the end of the day, fear is fear, we all have it, you either keep going or you let it stop you.

While I don't like generalizations about Europe (there was some topic recently here), this one is certainly true. It's something I admire about the American way of thinking, that failure doesn't kill you, it makes you stronger. AFAIK in most European countries (if not all), failure is treated like a toxic disease, both socially and by law. I believe it discourages enterpreneurship on a bigger level we can even imagine.

Hmm...this is interesting, thanks for sharing.

If I take this article a bit more literally - I was afraid of flying too (with airplanes), then I decided to put an end to it and took skydiving lessons; Yeah the ones where not only you climb to the sky with a plane, but you jump out of it on about 13k feet (4km). Liberating is pretty much the word that describes it, and I'd also like to think about the same sensation (minus a bit of adrenaline) when you actually succeed (however you define success is up to you) in business.

Does it really has to be that way? Is it flying or crashing the only possibilites?

Maybe not. Maybe soft landings are possible, just don't put everything you got in just one shot.

Could you expand on soft landing? Flying high and crashing and burning are somewhat self explanatory from a fund manager's perspective, but I'm curious what you meant by soft landing.

Do you mean a 'life-style business', or trying a few smaller ideas simultaneously?

(Genuinely interested, not sniping or anything).

(This is pure opinion, really)

Most of fund managers shouldn't be called investors, they make bets in companies like some people do in horse racing. Which is ok, but they sell this image where the only path to succeed is by getting huge like instagram or crashing like a thousand other startups. They are distorting reality for profit. Making bets is part of speculative investment, doing this to startups is cruel - specially when you have direct influence in the whole 'community'.

How it works:

Let's say you have: a set of ideas I, which pretty much englobes all ideas that have a some chance of succeeding right now, some ideas slightly overlap others, but that's ok. Now, you take N startups which are willing to take one idea and blindly go full throttle, to fly or die. Your job as a VC is pretty much igniting them and (that's the cruel part) making sure they do never 'pivot' to something smaller with a more long-term approach/returns. You worth more dead tomorrow than evaluated at 'only' 2 million in 24 months.

My point is: for every airbnb there are hundreds of very successful companies that have million of users and also impact the world and didn't play russian roulette.

Almost forgot (explaining soft landing):

The idea is pretty simple, find some market that are willing to pay (read: if you ask the money before the product, they would pay and then you ASK) build the product without spending your savings. Get more similar users. If the first 50 users you got are the only ones that want the product (very unlikely) maybe it's time to shut down the product and take the losses which will not be huge. You might even keep your old job when doing that. Most of ideas I got from Amy Hoy and DHH/Jason (book 'Rework').

Presumably something that's profitable but does not have mass appeal

Exactly. But yet, some end up getting really big.

When your motivations take form as massive visions that could fuck the world twice over, the only landing in your mind is how to keep it going for the next 10 years.

Landings per se are constructs of the market, not the entrepreneur. IMO obviously.

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