Jessica Livingston: What Goes Wrong | Hacker News Reader

Jessica Livingston: What Goes Wrong

foundersatwork.com

518 pointsnswanberg90 comments

The link assumes that you know who is speaking. But it doesn't give that critical piece of information.

Founders at Work was written by Jessica Livingston, who is a cofounder of ycombinator. She's married to Paul Graham. But do not think that she's in there just because of the personal connection. Her book is truly excellent. And in previous articles I've seen Paul say that the #1 thing that they want in a founder is determination, and the person that they rely on to spot it during the interview is Jessica.

She also contributed her financial and legal knowledge to YC. The others were "only" programmers.

The part about the "others" isn't really true. Paul and Robert had founded two companies together and Paul had been the CEO of a medium sized startup and taken it through the acquisition process.

Also, at least in the earlier YC batches before there were more folks helping out, Jessica definitely felt like the operations person; like she was the one that actually made things happen.

We are talking about the same thing. I meant operations as part of legal/financial -- the business side of things. As Paul put it in an interview at Mixergy.com, she brought the knowledge required to actually put YCombinator together. I certainly meant no knock on the other partners' experience other than what they claimed to lack themselves.

Two of the problems can be easily avoided: 'cofounder disputes' and 'investors' are not problems in case of single-founder bootstrapped startups. :)

One thing I would add to the topic of 'determination': Are we speaking about determination to make a startup successful or determination to try out as many ideas in our life as possible, learn as much as possible and try to make at least one startup successful in our life?

I mean first we have to analyze what we optimize for:

If we optimize for the success of a given startup then it is obvious that the optimal strategy is to never give up on the startup.

If we optimize for the success of a person in his lifetime then it is different. In this case we have to examine all kinds of opportunity costs. Could it be a better strategy to very quickly abandon a startup when it seems that people do not want the product, so that we can start much more startups in our life, to increase the chance of at least one becoming successful?

For me and my co-founder, especially during the dark days of 1) tech not working 2) clients stopping service with us or 3)someone yelling at us over Twitter, email or phone - it is Critical to have a team and more importantly to have a partner. I don't share all of my concerns with the whole team because that could shift the mood of the company and damage our internal resolve. But I need to be able to talk about the full reality of the situation with someone and depending on who is having an up day one of us can rally the other person around to being enthused again.

Without that, I know there would be days I would be lost, and if that lingered at all I could see weeks of inactivity at exactly those points where we needed to move fast.

I whole-heartedly agree with Jessica that having a co-founder that, above all, you can trust is huge (I'm lucky that I do), but I agree with the other reply here that a single founder, in almost all situations is more trouble than any sort of cofounder disputes.

I fully agree, but the partner doesn't have to be cofounder. It could be the wife (or husband), a very good friend or anything equivalent.

From what I have read so far the main difficulties of a single founder is lacking an alternate view and help to restore drive when in doubt or exhausted.

Of course other kind of problems may show up if the business is a startup of the dropbox kind. But this is a mazzerati problem. My feeling is that more than one founders expose to much more difficult and nasty problems than a single founder will met. A single founder can find paliatives for his weakness which do exist and shouldn't be ignored.

I can see what you mean here - my wife is my life partner, and she is a fantastic balance outside the support my business partner and I provide each other. But she has other things going on - her life is more than just waiting to hear about how Perfect Audience is going and having someone as focused as you are on your work baby, but in different ways, is useful.

You're conflating two distinct ideas: optimizing for the success of an idea, and optimizing for the success of a startup. They're not the same thing, because a startup can switch ideas. In her talk Jessica mentioned OrderAhead, which went through 5 ideas before the current one.

And what do you think about concept "Do fast and fail fast" meaning in general that you should give up idea (and startup that was based on this idea) as fast as you can if you find out that idea doesn't work?

I agree with "smart pivots" idea but "fail fast" is one thing that I don't understand in "Lean startup" concept as I'm quite persistent and I understand that in general it takes several years for startup to succeed.

Failing fast means that if an idea has a fatal flaw, you want to discover it as early as possible. When you phrase it that way, it's hard to see how anyone could be against it. This is for example why I encourage startups to launch quickly.

Oh, that makes sence when talking about ideas - not startups. Thanks.

In terms of outcomes I am convinced that co-founder disputes (been there done that) are still a lesser risk to success than the banal reality of simply losing motivation as a single founder. I am a rather determined person but would I have gone through all the way with my first startup while going experiencing the roller coaster? Almost certainly not.

Another thing to consider: In a dispute you may actually be the wrong one, and even if you end up leaving when you would have been right, your remaining co-founders may lead the company to some success while you retain your vested shares and can recharge for/ start the next thing.

In fact, it's much harder to be determined if you work without co-founder (i.e. at least 1 person who supports what you're working on).

> In fact, it's much harder (...)

It's not a fact, just an opinion or anecdotal observation. And I submit it depends on the person in question. Some folks may find it easier to have a co-founder, some may find that to be more of an obstacle. Both cases have merit. Agreed it helps to have other people support you, be a cheerleader, be a listener, etc., but that doesn't have to be a cofounder. Since cofounder implies equity stake, all kinds of painful problems become possible when a newborn business venture has ownership split between multiple people, with different vision, different motivations, different life circumstances, and often (but not always) different equity stakes. In an ideal world, having co-founders/co-owners can be great. But it can also be a path to hell. Depending on the situation.

Yeah, you're right that there's no 1 law that fits everyone. Still we can say that in general it's easier to work together than alone with a note that there are some exclusions, of course.

Here's a link to the video version of Jessica Livingston's talk from Startup School: http://startupschool.org/2012/livingston/

It really is great! I encourage everyone on HN to read or watch it if they have not already. As a not-yet founder, it has a lot of interesting advice that I don't think is documented anywhere as concisely and practically as it is here.

As a founder (2x) she has some absolutely fantastic advice. Though I haven't seen every problem/monster, many of them apply to my experience. In addition, the examples she gives are fantastic.

Any YouTube version available? (This player doesn't work good for me, keep resetting)

Worth the read just for this:

The pizza place was very confused by this, but they send the pizza guy without a pizza, Kyle answers the door, and the pizza guy says, "The site is down."

Indeed. I plan on using this as an example of what a clever hack is from now on when it comes up in conversation. It is adorable, clever, and just...great.

The Mixergy interview with PG (Feb 2010)[1] mentions Jessica working on a second edition of Founders at Work.

PG: "You know, that is her deepest wish. If she is watching this, she’ll be laughing so much at this point because that’s what she would like the most too to be able to spend more time on the new version of Founders at Work. There’s a new, she’s working on a new edition, with a bunch of new interviews."

Any updates on this?

[1]: http://mixergy.com/y-combinator-paul-graham/

This is extraordinarily accurate, based on my experience.

This is excellent -- and very much in the spirit of Charlie Munger's often-repeated saying: "All I want to know is where I'm going to die, so I'll never go there."[1]

[1] http://www.pbs.org/wsw/news/fortunearticle_20031026_03.html

Death is inevitable, these mistakes aren't.

Having started riding this roller coaster I particularly enjoyed a view of what pitfalls to be aware of in the future.

Also, since I just survived a dual-founder breakup (company intact), it was encouraging to know that this was probably a bigger bullet to have dodged. (For those curious, post-breakup I reached out to an old friend with whom I've shared some tenuous situations and we have applied to YC for the next batch)

Edit: I forgot about the pizza comment! When she asked how to contact someone in Lake Tahoe, I audibly said pizza (in my empty apartment). When the solution was pizza, I had a celebratory moment.

Very interesting. Statistically speaking, women are better than men in reading non-verbal information. I wonder if this is a part of YC success.

I think so. Within YC Jessica's nickname is The Social Radar. One nickname at least; the other is Panic.

PG, mind sharing some insight on the "Panic" nickname? I'm curious about how/if the two are related.

We call her Panic because she's the office worrier. I never considered her two sides might be related. Interesting idea, but I don't think so.

I wonder if her strength in picking up social cues also causes people to panic because shes the office warrior, detecting problems/issues and cutting through to their core.

My thoughts as well. Empathy has its costs. I was wondering if exposure to swings was one of them.

Gender differences are across entire populations, but individual variance absolutely swamps them. If you want to fill a single position, you're better off looking at the individual applicant's skills, not their genitals.

If you want to hire anyone probably best not to look at their genitals.

Fat fingered. That was a reply to btilly's comment

Funny. Larry Summers was fired from Harvard for saying something very similar.

Arguing anything other than differences in levels of persistent hard work and skill in your particular field has a large mountain of evidence to overcome.

The effects of those two are very large, the effects of everything else comparatively small per decades of startup and longitudinal entrepreneurial studies.

Nonsense about hustle is exactly that: nonsense. The weight of evidence suggests that, if anything, hustling and creativity have a net negative effect on long term health of a startup.

But there's money to be made keeping up the lie.

Lastly, beware of pseudo-pop-science that opens with only a few people's stories. People manage to succeed as founders all over the world; these stories are not remarkable and tell us nothing.

In general the whole "determination" thing has little to no value in any serious consideration of startup success: it's about on the same level of credibility as diet fads.

Well, played. For a couple of seconds I was wondering why I had this impression of deja vu then I found this (http://hackerne.ws/item?id=4692794). I burst out laughing.

Haha you got me. PG can rest assured that middlebrow dismissal apparently only gets a disproportionate share of upvotes when it's about health or nutrition :P

Success is always the result of hard work and skill, but failure is usually bad luck ;-)

I think you have the right internal Locus of Control (http://en.wikipedia.org/wiki/Locus_of_control) theory needed to succeed. But personally I believe the truth is a more nuanced (i.e, my Locus of Contol theory is a more external than yours :)

Environment is important too; generally, when people of modest background and means rise to found successful businesses, this is invariably mentioned in their biography precisely because it's unusual.

The influence of social environment, peers, connections, location, opportunities and just plain old timing do matter, in my view. Even Warren Buffett acknowledges that he won the "Ovarian Lottery".

Yep, I even believe in "luck" too (unpredictable external factors outside one's control). You can found a perfectly viable business, work hard, be skilled - and then become sick at a critical time. These things happen. Likewise, making the right connection or deal at just the right time can make all the difference to one's success.

Of course, as others have pointed out -your view is the most useful. You can only control what you can control. But do I advocate kindness to others, because persistent hard work and skill are no guarantee of success.

Keep telling yourself that :-).

This is another great piece of writing by Jessica Livingston (I was at Startup School for the talk as well).

Is she ever going to pursue writing a sequel to Founders at Work?

Jessica's speech follows one of the themes she established in "Founders," - overcoming emotional responses being a key to success in startups (and life). Her skill in communicating complex ideas is subtle, but more impressive because it lacks the usual dose of ego and/or one-upmanship. The sole intent being to help people who can listen well enough to use the information to help themselves.

Are people really having such trouble with the context of this article? The author's name is in the headline (maybe it was modded in later, to be fair), but also there's an "author" link[0] in plain sight. PG's essay's don't have a "who am I" introduction, and if you didn't know who he was then you'd simply click on the obvious "bio" link.

[0] http://www.foundersatwork.com/author.html

At the point where I replied, the name was NOT in the headline. It was definitely modded in later.

I know this is a minor issue. But when I publish something I want people to inform me of problems. Please note that I don't mean to be disrespectful and just want to help. So here goes:

3rd sentence: "There's a talk I've always want to give at the beginning of each batch...". I think this should be either "I've always wanted to..." or "I always want to..." right?

Fixed - thanks!

Wow! Thanks for replying. I have already been down-voted once for what I posted and was beginning to think my comment was a huge mistake.

As hackers we get trained to look at details. So I was hoping others on "Hacker News" would understand where I was coming from. It's not about right or wrong. It's not about ego. I just thought I could help.

I love this! It's one of the best pieces of startup advice I've read in a long while; I've sent it to my startup friends. New fave quote: "Determination is really two separate things: resilience and drive. Resilience keeps you from being pushed backwards. Drive moves you forwards".

If you are interested in a take on this topic that is based on data, check out Noam Wasserman at BoS 2009 (his talk at BoS 2012 was very similar)

http://businessofsoftware.org/2009/05/professor-noam-wasserm...

He has been collecting data on start-ups and then looking at survival lengths and outcomes. He wrote a book on the topic

http://www.amazon.com/Founders-Dilemmas-Anticipating-Foundat...

In order to make something people want, being brilliant and determined is not enough. You have to be able to talk to your users and adjust your idea accordingly. Ordinarily you have to change your idea quite a lot even if you start out with a reasonably good one.

-- This is a great point. Even outside of startups.

I saw this talk at Startup School. Honestly, as someone working in industry who tried doing a startup during school, there's a huge thing missing.

CMD+F for "luck" = 0 results.

Luck is a huge factor and sometimes you just need to move on to either something new, or working for a company to fill in the gaps, and trying again soon.

Talking about "luck" in a presentation like this is like talking about the life benefits of physical attractiveness.

Precious little of it is in your control, so what's the point? Address what you can control, and hope for the best.

This is an interesting point, at least the initial first premise. The conclusion seems off though. In order to leverage your own assets, you need to be able to size up not only your own strengths and weakenesses, but also those of others. PA, like social status, and others of the same ilk is a real (if not always 'earned' asset). As such, you should never ignore it or be oblivious too it. It falls in a spectrum of intermediary assets -- like connections -- that you just cannot be aloof to. Understanding the odds matters -- This is just "Luck" considered as an proxy for stochastic variation. Understanding the odds is critical to strategy/rational decisionmaking under uncertainty (such as making an NPV>0 wager). There are few examples where the ability to make rational decisions under pervasive uncertainty is more important than in a startup. This (just throwing it out there) might be one reason startups fail. Or it might be one reason that contrubutes to something that was in fact mentioned (founder breakups, having a deal blow up, etc).

There is one big difference between luck and attractiveness, though. Luck is a big unknown except in hindsight. If you knew you were going to be unlucky, there's very little you could do (I hesitate to say nothing but I can't think of anything).

Luck is a big unknown except in hindsight

Tools, techniques, and strategies for dealing with "the unknown" are a fundamental part of intelligence. As a corralary, the denial of uncertainty is the most un-intelligent of strategies.

It follows that your statement has within it a bit of insight: just knowing that risk matters. So even if you can't know (with precision) your exact 'luck' at every moment, you can build upon the fact that X,Y,Z observed variable could have gone another way had P, Q, R not happened by chance. Just being aware of the magnitude of the potential variation is a useful piece of information. For example, this can guide you to more rationally hedge your bets. Or to "make luck" by managing variables to not happen by chance. Or to just know when it makes sense to keep rolling the dice -- persistence & resiliency. Etc. In this sense, Jessica did touch on something that seems to come in handy here -- resourcefullness -- just in general but in particular when the "enexpected" happens.

Luck is like time travel. Once you've done such an analysis, luck moves on to represent all those factors that you didn't take into account. That's what the word means.

PG has a good quote, how ignorance can be useful when it keeps you from making other, bigger mistakes.[1] I think this is worth keeping in mind. Does ignoring luck [2] make you better off? Its not clear ignorance is the only strategy.

______________

[1] http://www.paulgraham.com/mit.html; see also

[2] http://en.wikipedia.org/wiki/Luck

http://en.wikipedia.org/wiki/Knightian_uncertainty

http://en.wikipedia.org/wiki/Risk

http://en.wikipedia.org/wiki/Stochastic_process

> If you knew you were going to be unlucky, there's very little you could do

I believe the startupland term is "pivot."

Actually you control luck with determination.

By increasing determination, you decrease the effect luck has on anything you do.

And for that matter, you can control physical attractiveness. There's always something you could do if you really had to, right? Lose a little weight, gain a little weight, hide your flaws, accentuate your good points, dress a certain way. You know how sometimes on tabloid covers in the supermarket they have pictures of celebrities wearing sweats and no makeup? It's a petty thing to fixate on, but it illustrates a valuable point.

The initial analogy with physical attractiveness is broken. Physical attractiveness is akin to the intelligence you're born with. You may not be able to boost your intelligence much, but you CAN minimize the factor luck plays in you realizing your potential afforded to you by your intelligence.

Agreed, but I would put it slightly differently.

Every goal has a percentage likelihood of success, your job (as the goal-reacher) is to increase the likelihood of desired outcomes.

Ex: Moving to SF increases your luck-factor/success-percentage of meeting a VC at a coffee shop. (Assuming there are a lot of VCs at coffee shops in SF) Therefore you have become more "lucky". You have probably also reduced your luck-factor for seeing a cow in the morning.

Consider a rigged die with the probabilities for hitting any one of each of the six numbers skewed in some way. You won't be able to tell that it is the case until you roll it many times.

Consider an entrepreneur. She has the ability to build a great product. Given one day at it success may not be evident, but after months, or years of persistence, she'd (eventually) achieve the result her potential affords her.

There is nothing wrong with your examples, but it's a more narrow example.

"Luck" is showing up consistently so that you're present whenever opportunity decides to show up. Thus, you make your luck. And I believe this is where the resilience mentioned in the essay comes in; to ensure you always show up.

One of the most interesting investigations into luck was last year's show The Experiments: The Secret of Luck, by Derren Brown. The entire episode is avaiable on YouTube here: http://www.youtube.com/watch?v=O4mN33w5Ftw

I would heartily recommend anyone watch it, it certainly enhanced my own understanding of the concept.

The whole resilience thing is about pushing through all the bad luck that can be expected to come along. So that you're there when the good luck comes through.

Sure, not everyone is going to make it, and the bad luck is going to finish them. But doing a presentation about waiting around for luck to strike would be extremely bad advice.

While there is variation in outcomes, people who have posted consistent results show that luck isn't the major determining factor in long-term success. Luck will change the amplitude, but it's up the skills of the founder to make sure they are always pushing through the bad times to reach the chance to succeed.

Awesome read!

Jessica mentions the Codecademy team launched 2 days before Demo Day and managed to signup 200k users. If I remember correctly, they launched on HN through a Show HN thread.. and so on..

What I really want to know is, how many of those initial 200k users stuck around? I was one of them and I have only signed in maybe twice since their launch.

So what does that mean? they leveraged the curious users to get VC interest? Did they really engage me, us, the 200k? is that a false positive?

I guess if the net result is a positive one Today, none of this really matters.

Really I would think it doesn't matter. With that kind of interest (even if it just of the curiosity kind, rather than the stickiness kind), then it's a definite flag that you're onto something.

So, even if the 200k users never came back, there was clearly something interesting about the concept to get that much attention. And with the right development, the next 200k people can be convinced to stay around.

It's a lot easier to convince 200k people for a second look than it is to find 200k in the first place.

This is one of the best articles I have read in a while. Obviously you see a lot over 7 years/ 500 startups.

Wow. Great advices. I especially like the resilience part. Those rejection stories really hit home, as I have gone through similar experience recently. When reading them, the line "when life deals you a lemon, make lemonade" kept flashing through my mind.

Loved it. Very informative. Being an entrepreneur is a tough road, but with preparation, belief, and determination things will eventually take its course.

Are those Pokemon in the first figure? If so, I have severely underestimated the coolness of next-generation Pokemon.

Jessica got those monsters from Mino Monsters (http://minomonsters.com/).

(When you've funded 467 startups, you can find one to supply you with practically anything.)

A byline would be helpful, here...

There's an "author" link: http://www.foundersatwork.com/author.html

I read this yesterday thinking it was from pg, strange feeling.

"Investors tend to have a herd mentality."

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I don't mean to be impolite, but do you honestly not know that "Founders" is one of (if not THE) seminal work on the culture of startups and their founders?

I guarantee you cannot name three books that have done a better job capturing this topic, because they don't exist.

Claiming that Livingston's relationship with YCombinator/Graham is the reason why the book is so wonderful, is like claiming David Pogues relationship with the NYT is why he's such a popular tech reviewer, or Manohla Dargis is such an amazing movie reviewer

It misses the point of both their contribution, and talent and is frankly, quite rude.

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The point I was trying to make is that they take other people's work, and present it to the world in a different form.

Compare 'Founders', to something like Walter Isaacson "Jobs" - both of them had lots of interviews, with transcribing, and edits - but I got a lot more out of 'Founders' (as did everyone I know) than Issacon's book. Issacson supposedly had 100% access with his relationship to Steve Jobs, but I don't know if Issacson didn't know what questions to ask, how to ask them, how to make his subject comfortable, what the important parts were to capture, or (my opinion) - just didn't really care about his subject that much. It was a huge disappointment for me.

Founders is a delight, and I attribute that pretty much 60% to the author, 40% to the interview subjects, and 0% to Paul Graham.

If Livingston had been assigned to write Jobs's Biography it would have blown our minds. And, of course, you would have said it was good because she was related to Paul Graham.

My reading is that Isaacson cared more about Steve Jobs as a human being than as a living case study for entrepreneurs and wantrepreneurs. Steve Jobs commissioned the biography so his kids would have a better idea of who he was as a human being, not so you and I could learn his secrets for building a startup and being a CEO. (That project was internal to Apple: http://articles.latimes.com/2011/oct/06/business/la-fi-apple...)

It would have been entirely possible to accomplish both missions. Tell the story of unblinking-dropout-denying-father-commune-living-india-visiting-fruit-eating-acid-dropping steve, at the same time that you tell the story of how he built Apple, Next, Pixar, and Apple 2.0, and what it meant to him.

I don't think there was a single follower of Steve Jobs that was very satisfied with Issacson's Biography. I didn't even really feel like it told me about Steve Jobs the person.

"Let's be serious here - Founders at Work was a list of wonderful interviews with startup founders and its creation was tied directly to her personal relationship with pg.

Sigh To all downvoters - indicate why this is a) demonstrably wrong or b) demonstrably unfair. It is both true and verifiable - don't just downvote me because this disagrees with your world view."

It is ridiculously rude because it implies that she could not possibly be a YC cofounder based on her professional skills and that her book was not a product of any work/insight, just a side benefit of her personal relationship with PG.

I don't think he implies that. Those two things are not contradictory. She could be an outstanding professional AND be there because of her connection. There is nothing wrong with that. It happens all the time, everywhere.

He does. Her personal connection is not relevant unless her professional one depends on it. To point it out as a relevant piece of information implies that the dependency exists.

It's true, verifiable, basically uninteresting, and unusually rude.

From the grandparent post:

> Her book is truly excellent. And in previous articles I've seen Paul say that the #1 thing that they want in a founder is determination, and the person that they rely on to spot it during the interview is Jessica.

So which part of that are you trying to contradict?

The way I read it, your description of her book supports the grandparent's claim. If you are able to create a collection of wonderful interviews, what's the common denominator there?

So what? Steve Jobs biography arose from his personal relationship with Walter Isaacson.

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