only when people’s basic needs are met – when they cease to worry about jobs, education, healthcare, transportation – can they truly be free

I was thinking about money today, mostly because I made a costly mistake. It made me remember a quote from a Chinese TV series that was along the lines of — if the problem is something that can be solved by money, consider yourself lucky; there are so many greater problems that money can’t solve, like the death of a loved one, illness, or lost time.

I think most of what people say about money is generically true but in the process of being both generic and true, these sayings are also easily forgettable. Hopefully in this post, I can put out something that is more specific and true and along the way we can figure out the edges of things, to better see the shapes of things.

Firstly, a quick aside on capitalism — what I value about capitalism is that it is currently the best way we can make human behavior easily predictable and in so doing, predictably changeable.

Specifically on money, I want to break down the dilemma of choosing between making a lot of money and then donating it to causes vs making less money but doing something that starts impacting a cause on day 1. The edges of the spectrum are, on one end, making a ton of money with no cause-related impact (in here, you can substitute in for “cause” whatever you want to achieve) or negative cause-related impact (say, selling drugs, if your cause is to lower homelessness), and, on the other end, volunteering for that cause for free. Of course, there are choices in between, and the decision will fall somewhere along the spectrum.

First, people say money is freedom. I think what money brings can be broken into two categories. The first part is security, which is what’s in the title of this post – a broad definition of security for yourself and your loved ones (which is its own sort of messed up in the US, but we can discuss that another day). To me personally, after security is fulfilled, money has no incremental value because most of my pride derives from intangible things. That is the second category – pride derived from money and what money buys. Therefore, one extreme of the spectrum is people who value money only up until the point that it fulfills security and the other extreme is people who value money for security and who also derive all of their pride from money and what money can buy.

With these building blocks, I therefore think the way to think about the dilemma is this: In the case of making money and then donating it — money itself doesn’t solve a big problem; the hard part is the time, the attention, the empathy, and the will. Instead, money buys others’ security (+ amount of money that is needed to satisfy their pride) so they can devote their full time / attention / empathy / etc.

The choice of starting on day 1 versus making money and then donating it to solve problems requires merely enough money to satisfy your own security + pride, and then you can go devote your time / attention / empathy / etc.

Thus, I think the questions to ask to determine which path to go down gets simpler and more targeted. In rough order of importance, they are:

1) what is the expected “units” of people’s security + pride that I think I can buy by going down the make money route?,

2) what is the cost of unhappiness to me to get to that expected value? (usually underestimated),

3) what is the cost of the passage of time for the cause(s) I’m interested in?,

4) do I think my time / attention / empathy / etc for some reason or other has more value for my cause than that of the average person’s?, and

5) do I think the average person requires more or less money for pride than me?

But as you might notice, really, it all rests on the first three questions, especially number 2, because the magnitude is so much bigger for those than can ever be the case for 4 and 5 (cases of extreme ability or extreme selflessness / greed).

I’m not positing that this is the best way to consider the decision, just something interesting to think about re the role of money in this decision.

only when people’s basic needs are met – when they cease to worry about jobs, education, healthcare, transportation – can they truly be free

if you only read the books that everyone else is reading, you can only think what everyone else is thinking

Quote a la Murakami via Norwegian Wood

Following up on impressions since Dropbox…I remain convinced that the class teaches us to be good venture capital investors…and potentially very cerebral entrepreneurs. Which is actually great if it’s being taught to an audience of lawless cowboys, but not as great when it’s being taught to an audience of ex consultants and bankers (myself included) already prone to analysis and being primed for it in every other class we’re in. Arguably, however, conveying the messy world of entrepreneurship isn’t the goal of the course (that’s the goal of our working to build businesses in 3 months) and I imagine being an entrepreneur within a larger organization is much more orderly and structured, allowing one the luxury of being this type of cerebral entrepreneur.

That said, that’s not the point of this post — I should’ve mentioned that despite some of the questions I had about the class, at no point was there any doubt in my mind that my professor was a master teacher. It’s really interesting to see across the spread of my classes this semester, the vast difference between a master vs a novice professor, especially in such a finicky teaching model as the case method, where even if you’re dying to just tell the class the answer, you’re actually supposed to elicit it out of the class. It truly is an art form, a type of quintessential influence without power situation.

One of the key things the professor must get right is how to ask the right questions, which our entrepreneurial manager professor demonstrated beautifully today. In the last class, as is often our privilege, we had the protagonist come and wrap up the case. As is customary, the screen comes down (s/he’s simulcasted) and the speaker speaks for about 10 minutes before opening the last 10 minutes up to questions, during which, of course, only the classroom in which the speaker is in gets to ask questions. Our professor made it abundantly clear beforehand that we could indicate when we’re bored with the discussion and he would turn off the feed. This isn’t unusual.

In this particular case, the speaker wasn’t great, and the class voted him off the stage about halfway through his Q&A. Again, this isn’t unusual. And oftentimes, there would be nothing else to it.

Instead, opening up class today, our professor asked us why we voted to turn the speaker off, essentially where did he fail as a communicator. This question had never been posed and I doubt it ever will again in my remaining time at HBS. It’s a very thoughtful question that makes us reason out a reaction that is typically just written off as boredom or irrelevance. Without this question, we wouldn’t have even dissected the ways in which this clearly competent and passionate individual failed to convey both of those qualities to an audience probably similar in DNA to his investors.

This reminded me of a concept I had read about approximately a year ago. That is this question of what we should talk about. The point is that there are two reasons for most conversations (barring specific reasons like comfort, advice, etc.) — 1) to socialize and 2) to gain and spread useful insight.

If we want merely to socialize, we would talk about whatever everybody else is talking about — ISIS, Jeb Bush, Oscars. But instead if the goal is to gain and spread useful insight, we would want to look at relatively neglected topics — ones that are important yet not very often discussed, where it seems like discussion can result in the most progress, and where the participants in the conversation have some sort of expertise. Robin Hanson pointed out that this is a clue to help infer the conversation motives of the people you talk with — and of yourself. “I expect you’ll find that almost everyone mainly cares more about talking to socialize, relative to gaining insight.”

One level deeper on this subject is how to think about these neglected topics. True, a very classic way to incite interesting conversation is to pose contrarian points of view. The difficulty with being a generally contrarian person is that oftentimes we get carried away and insist in being contrarian for the pure sake of it. This creates a situation in which bias and inaccuracy easily creeps in, especially since to have a truly contrarian assertion, one actually needs a substantial amount of expertise or depth of insight…on the whole, the crowd is right and honestly, there are more people interested in being contrarians than there are with the right amount of insight (Americans are particularly notorious for this…as covered in a This American Life episode called The American Jackass).

Instead, arguably, we should all be objective in our facts, answers, and conclusions and instead be contrarian in our questions. Instead of posing the conclusion that nobody is thinking, we should be posing the questions nobody is asking to get to interesting conclusions that nobody is thinking.

So elegant. Now the question is how to actually get good at asking questions…more thoughts on this later.

if you only read the books that everyone else is reading, you can only think what everyone else is thinking

death does not concern us, because as long as we exist, death is not here. and when it does come, we no longer exist

Quote a la Epicurus, from this wonderful answer on Quora.

I was at Hack@Brown this weekend, which I can’t recommend enough (we also won best mobile app! stay tuned for whether or not this becomes a full project :)). I haven’t been to as many hackathons as I’d like, but from my limited sample, I think this one was really unique and intelligent in its design (as well as just general good attention to detail in the form of branded napkins, quality of volunteers, sleeping rooms, toiletries in bathrooms, tea bag sleeves with tea puns like “chai-fi”, “t++”, and “<h-tee-ml>”).

The hackathon’s philosophy is captured in a recent tweet of theirs — “everyone at a hackathon is a winner, simply because they’re either learning or teaching.”

With this philosophy, they set out to design a competition focused on the process rather than the winnings. The resulting environment meant that people were more willing to build on unfamiliar technologies such as the Oculus Rift, Microsoft’s Kinect, the Myo armband, Spark Core, Unity, etc. The amount of learning was thus made even more immense in a mere 23 hours of work.

One of the key things Hack@Brown did to propel this ethos is in how they allocated their spending. The team reportedly brought in a total of $90K of funding, of which the vast majority went to running the hackathon — basically, making the process amazing for every participant. A very, very small amount (if any!) went to the final prizes for winners.

Having run a few college competitions, I know this is not the norm. A majority of the sponsorship usually goes to the winnings in hopes of attracting really talented teams to compete.

Instead, Hack@Brown viewed every competitor as a talented individual and gave them the safe space and the countless chocolate-covered strawberries and customized Build-a-Bears to enjoy the process. Many times through the night, I heard teams say things like “man, we already won with all this free stuff we’re getting.”

They also made sure there was a 1:7 mentor:participant ratio — and it was a pretty stacked set of 50+ mentors, many of whom were also actively recruiting talent. Knowing there’s a readily accessible safety net also made the participants push themselves out of their comfort zones.

This is really interesting from an organizational design standpoint. The second point is already very often discussed — how do you create a safe environment for employees to take risks — so I won’t belabor it. But the first point is a bit more nuanced and interesting — how do you make the process of working at your company more enjoyable than the rewards of working at your company? How do you create an environment where people aren’t just there to win the next promotion or raise?

It reminds me of a lunch we had with our LEAD class professor from last semester where he breaks down how companies attract and retain talent. There are 3 things that attract talent — the prestige of the company, the inspiration of the vision, and the compensation (graded on fairness rather than absolute quantity). Then, there are 3 things that keep talent — the quality of their peers, their ability to develop personally and professionally in the company, and the work/life balance. And what sits at the middle of these two sets of qualities and helps both attract and retain employees? The manager.

So what levers do we pull to make the process more enjoyable? Making sure the quality of employees’ peers remain high (popularized by the famous Reed Hastings deck on culture and responsibility at Netflix), making sure there’s work/life balance, and making sure employees get to develop. Oh and small niceties do matter — of the free meals, snacks, unlimited office supplies variety…but they really do pale in comparison to the three above.

And I guess at the center of everything, you, the CEO, are a manager of managers.

death does not concern us, because as long as we exist, death is not here. and when it does come, we no longer exist

whatever you do, DON’T look away

Somehow the world recently got notice that design thinking is a BIG DEAL and now, I see at least one event a week that brings it up. One of the pillars that is repeated ad nauseum is how important it is to be observant and empathic. How it is already difficult enough for us to notice many of our own problems because we’ve hacked together good-enough solutions and even more difficult to notice others’ problems when they no longer notice.

David Rose, author if Enchanted Objects, recently gave a talk in which he shared a number of ordinary objects he “enchanted” by connecting them to the internet and allowing them to have some interactive component, like a pill bottle that beeps and calls you to improve your adherence to taking your medicine based on when you take off the lid; or like an umbrella that changes color based on whether or not it is likely to rain.

At the end of his talk, a question came up — how do we keep this from becoming a sector that just builds toys for the top 10%? Toys.

The thing is, oftentimes the people who have the privilege of time and knowledge to build are not the ones who have the most need. So if we, in this privileged group of people, continue to build to solve our own problems (a common piece of startup advice), we will increase this divide. Our lives will keep improving, even in trivial ways, and we will be further and further removed from those whose lives do not.

So the bridge here is that supernatural ability to be able to notice others’ problems when they don’t even notice them anymore. This means when we see something that is painful to see, difficult to accept, we must not turn away. This includes the homeless person on the street in sub 20 degree weather or the disfigured teen who gets bullied in the parking lot.

Instead, we should look closer. Observe. And find a solution.

whatever you do, DON’T look away

what does it look like if we win? what are the risks? now go and get on with it

The title is a line Colin Angle @ iRobot shared in a talk last Friday.

As I enter my second semester in business school, with fewer misgivings than in my first, I am just starting to attend my first purely entrepreneurship-related class, which HBS calls The Entrepreneurial Manager or TEM. So far we’ve had one class, focused on Dr. John’s foray into manual+electric toothbrushes, and I just finished reading the case we have for tomorrow’s class on Dropbox. Though I am not a true insider at Dropbox, I feel like I have a more intimate than normal relationship with the company given my observation of its growth, of an investment in its Series B, my relationships with some people who work there, and my personal experience recruiting for the company in early 2012.

It’s odd to sit in a class about a topic that is usually really interesting to me, observing a professor who is clearly very skilled at his craft and feel completely disengaged. I felt the same way reading the Dropbox case, despite that there were a few insights a la Drew Houston that I thought were worth jotting down (1 – no startup has been built successfully through distribution deals without a strong brand of its own, 2 – look for users requesting features that already exist on forums because that means they can’t find it, 3 – if you’re building freemium, you have to view your free users as your marketing cost — only then does it make sense; the product has to grow organically).

There is something that is too rational about this approach to entrepreneurship. The case was too rational, the path was too clear cut, there’s no way somebody without entrepreneurial experience before this case and some insider knowledge of what actually went down at Dropbox can get a sense of the utter chaos of entrepreneurship from this case. They can’t even get a hint of it.

So that leaves me wondering…why? Why did it have to be written this way, in this neat little package? The case is a relatively flexible format; we’ve even had full multimedia cases before. Why did the writers choose to create such a cool-headed, logical story out of something that clearly isn’t? If HBS really wants to be competitive in entrepreneurship, why is it misleading its students about what building a successful company looks like?

I’m both baffled and disenchanted.

what does it look like if we win? what are the risks? now go and get on with it

the world stands aside to let anyone pass who knows where (s)he is going

I haven’t blogged in forever, partly because I haven’t had time for the blogging itself (or really the mental energy…as I’d mentioned in a previous post, it’s really all about energy management rather than time management) but mostly because I haven’t had the time to really process the experiences I’ve been going through.

I won’t go into detail about these experiences in this post since there’s really just one point I want to hit hard — when starting a company (or really doing anything hard perhaps), if you are decently smart, persistent, resourceful, ambitious, and hard working, you can make anything work. Up until a point. That point might be measured by time, growth, revenue/profitability, number of users … point is (heh, pun), if you have the above characteristics, you can find an area to consult in.

A consulting company is not a startup. Or at least in our colloquial definition of a startup, which is generally a company capable, eventually, of exponential growth at relatively little incremental labor.

The scary part is that you might be able to build a several million $ company that actually is not a startup and not realize it until a few, labor-intensive years in.

This makes me recall 2 things from my college/intern days that I now understand with more nuance/depth:

1. There are countless $1 million checks lying on the ground just waiting for you to pick them up – true but you have to work your butt off. You can earn several million with a lot of hustling and hard work and risk taking…that never ends. Or you can just get a job that pays you a good fraction of that but gives you nights and weekends and significantly reduces your risk. There’s a reason why most people choose the latter.

2. I’ve been told multiple times that the most important quality VCs look for in founders is self awareness / honesty. Basically the ability to see it as it is and act accordingly, with as little bias from ego and other non-reality-based influences as possible. This is hard. It’s hard to look at something you’ve built and say hey, this isn’t going to turn into a startup, so I’m just going to walk away now. The easier route (surprisingly) is to say hey, I’m going to work a little harder for just a little longer…isn’t popular lore all about “the dip” before success and persisting through failure?

Ever since the Lean Startup craze, people have gotten pretty pivot-happy. I don’t have a lot of anecdotal evidence from people other than myself, but, man, after the first pivot, you realize that it’s no walk in the park. Individuals shouldn’t treat themselves as lottery tickets and neither should startups. After more than one pivot, I really think one should really take a good look at either one’s understanding of the space or ability to aim before firing.

To persist through all this and make it, I think you really have to

1. View this as something you’re fully committed to – if you’re going to build a company, at some point, you have to commit to it for life. You have to at least have the confidence to believe it’ll last that long and that you would want to stay at the helm. The amount of work and persistence through failure necessary to grow something from nothing is hard to surmount otherwise.

2. Be a little crazy. :)

the world stands aside to let anyone pass who knows where (s)he is going

don’t pray for easy lives, pray to be stronger…

More of an internal pep talk than a public blog post:

Maybe it was the coffee, but I found myself resolving to be stronger on the bus ride home from an event for work. What made me so frustrated with myself recently is that I know I am stronger than this. Do you ever feel…that if you let yourself get too coddled by those around you, you will grow to think that maybe you can only survive when swathed with care? And you become fearful of the day when that cocoon disappears. And slowly, though you see it coming the whole time, that fear envelopes you more intimately than the care.

This insecurity only exists when you think there’s something to lose, and it grows proportionately to the likelihood you think of losing it, how much control you think you exert over whether or not you lose it, and how miserable you think you’d be if you did. But note that all rest on perception.

The only sustainable antidote is self reliance. Not of the categorical variety where you trust no one but of the quiet confidence that arises from knowing that you bring value to each relationship and that value is independent of the other person; that is, it will stay with you regardless of the other person. Accepting the cocoon as a nice to have but not a must have. Making sure that you have resting posts, not crutches. Dependence is self-esteem destroying, dangerous.

One of the best builders of self worth is helping others. This spans from helping strangers to being there to support those closest to you. Helping others generates the perception of capacity because it requires strength. The debilitating thing is that we actually expend a lot of this valuable strength fighting ourselves. I find myself here right now. I expend so much at civil war that it’s hard to build up enough strength to use externally, which leads, in turn, to more doubts and more civil war. This will change.

don’t pray for easy lives, pray to be stronger…

variation upon a theme

She had slipped into the party unnoticed, trying hard to pretend as if she’d been there since the very beginning. He had spotted her first and his eyes had crinkled in cheerful, conspiratorial recognition. She felt sick at the sight of them but grimaced a smile back.

He turned back to Jess and murmured something in her ear; her sister straightened and turned to look in her direction.

“I’m so glad you were able to make it, Liz,” she dimpled prettily. “Jonathan was beginning to tease me about making bets.”

“And I would’ve won, too,” Jonathan rejoined with a good natured grin.

Liz blushed. “Sorry, I had work and-”

Jess waved her excuse away. “Tonight’s not the time to worry about apologies. We’ll settle accounts later.”

“That’s what she says when she hasn’t thought of the perfect punishment to suit the crime yet.” Jess laughed it off, but Jonathan shot her a I kid you not look.

Suddenly Liz felt a surge of rage. Who is this stranger, this outsider, who presumed to know her sister so well? What has he done to earn it other than share her bed and give her gifts on Valentine’s Day?

The anger started a slow burn at the back of her throat. The quiet, persistent rage left her mouth dry.

“Liz? Liz!” She refocused on Jess’s exasperated face. “Have you been listening to a thing I’ve said?” At her dumbfounded expression, Jess rolled her eyes. “You’re supposed to go on stage in fifteen and say a few words about Jonathan and my engagement. I thought it’d be better to have you open than dad and…”

Jess’s words faded into the background again. Suddenly all Liz could think of was the hopeful yet hopeless feeling she had had earlier that day. Who was that woman? That woman that had hugged and then kissed and then led into the hotel room the man whose silhouette she didn’t dare to recognize? She wanted, desperately, for this to be some man she had never met, some tryst six degrees removed from the cocoon that she had carefully woven around Jess since their mother had passed away two decades ago.

“Liz, are you ok-” He pulled back sharply at the sight of her face before she quickly herded all her wayward emotions behind the glass mask of social niceties. Jonathan took a moment to recover; his face showed the aftershock of seeing a wolf beneath sheep’s clothing and realizing that it was already too late; he had already let the wolf pass the gate. For the first time that evening, Liz felt Jonathan eye her warily, questions undoubtedly going off rapid fire in his mind – what was that? did I imagine it? does she know?

But they both knew he was now merely a player on the sidelines, an accessory, helpless as he watched the action unfold.

Somehow, someone, from somewhere, handed her a mike. She blew into it, made a few ice breaking jokes, and walked towards the stage. She could feel his eyes – and those of all their friends and family – follow her.

When she turned to face their expectant faces she hesitated. Her eyes found Jess’s and she felt an inflow of poignant reassurance. Here was the beautiful girl – woman – that she had raised, that she had protected all of her life, that she would give anything to see happy. That meant working three jobs sometimes, that meant not having a social life for the majority of her adult life, that meant having her personal happiness take a back seat to Jess’s.

But the world is a big place, much bigger than the roomy bird cage that she had constructed around Jess. Like a dutiful parent, she had shown Jess that world and warned her of its dangers. Like a protective parent, she had kept Jess satisfied in that cage for as long as she could. Like any parent, she knew there were certain pitfalls Jess had to experience herself to learn to avoid.

But maybe she could keep her here a little longer. Just a few more years. Maybe she could make the cage a bit bigger, stretch herself a bit thinner to envelop it under her aegis. Maybe if she were just a bit stronger or smarter or faster…

Liz cleared her throat and brought mike to her lips.

variation upon a theme