1. Right now I have an advisor to Do who has been tremendously helpful in an extremely short amount of time. Regardless of our future, and especially if we are successful, I will be extremely indebted to him.

    About a year ago, my friend Sujay, introduced me to the SherpaVentures/SherpaFoundry team. Nearly a year later, Do.com is launched, growing fast, teaching me a lot, and I couldn’t be more grateful for that introduction. I knew Sujay through college, and we became better friends when he was out in SF, but for the amount of time we have spent together, and perhaps even known each other, the value that this connection created in my life is disproportionately high.

    It’s funny. Not all relationships should be measured by the value provided to either party. Certainly not. But it’s interesting how a few people, a few moments, make a disproportionate effect on one’s life, and sometimes can be traced to the newest, or least expected, or briefest, or who knows what type of relationships.

    It’s funny.

  2. At 9:15pm PT (12:15am ET) tonight I got a couple of nice texts from my parents.

    At 9:30pm PT (12:30am ET) I arrived home at my apartment and checked my mail.

    To my delight, the mailbox had a sole item. A blue envelope from my parents, assuredly containing a card for tomorrow, my 25th birthday.

    There is nothing like family.

    So cliche, yet so textured for those patient, humble, and self-aware enough to appreciate the nuance.

    Every year, my parents make a point to send a card. And it’s always on time. Indeed, if I don’t confirm that I received it, they ask to make sure.

    In a world where professional ambition can blind us, our latest app idea can distract us from meaning, our personal lives can seem like the most important thing, it always comes back to family that is there for us.

    It’s the text wishing happy birthday even though it’s past midnight, and the call that would normally happen instead if they weren’t afraid to interrupt my work, and the call that happened right after once we both knew we could talk. It’s the card, reliably there at 9:15pm the night before my birthday.

    This reliability is rare and sacred. Only a fool would dismiss its value. Yet we all forget until we’re reminded.

  3. We are a fan of Slack at Do.

    (People can debate how different it is from Hipchat, or IRC in general, or Yammer, or anything else. That’s fine. The main differentiation, I think, is a smooth, intuitive user experience. People are still getting used to understanding design as a competitive advantage and perfectly dominant point of differentiation. They will eventually get there. Reference: Apple. But that’s a longer, different conversation.)

    For now, I want to focus on this concept of embracing laziness. Slack has made it SO easy to share screenshots, but there’s a tension that holds them back in this particular use case.

    1. Take a screenshot.

    2. Paste it into Slack

    3. Hit enter on this screen

    (Compare how easy this is compared to Tumblr, where I’m writing this post…where you have to save the screen shot (vs. an unsaved version via Mac OS X being copy/pasted…a subtle nuance because it’s so nice to not clutter my computer with screenshots I don’t need to save…then select it from a file picker you can only trigger by hitting the camera icon like so…

    and then it inserts….)

    But, back to the point…

    Slack highlights the text of the file, so you can rename it to something useful. Hitting enter instantly posts the file for you.

    They want you to provide a descriptive title, because it will be significantly more useful in the future. ‘Screenshot XYZ’ is useless for archiving, search, etc. This has always been true on Mac OS with screenshotting (and I suppose Windows when you could have done the same with PRT/SCREEN). Slack can provide unique value if they get people to name their screenshots. But that is a big if.

    However, when we are in the mode of just sharing an image, it’s “friction” or “cognitive burden” or “thinking” to add a descriptive title. Even though they want you to be descriptive, it’s more work. So I’d wager most people don’t do it.

    Note… that I usually am writing a comment (not a title) actually when I post, e.g, “Nice!” or “Check this out” …but NOT the title, and I suspect the same is true for other people, but the title field is selected…so then I end up associating NOTHING with the file (I type my comment in first, and then I add the image separately with no user-input metadata), as opposed to at least getting my comment out of me tied to the image. Defaulting to title input seems like forcing an aspirational behavior vs. embracing laziness. That would be better than nothing (to capture my comment at least), but as it stands, Slack is trying to force a file name and sacrificing associating my comment with the file in the process. Might be for the best, and I don’t have all the data, but who knows.

    The bigger idea here is that as product people, we make decisions for people. We debate how opinionated a product should be. What should we force on people? How do we move people to do a certain behavior? Do we bridge them or do we radically force behavior change? I thought Slack’s decision here was an interesting case study of choosing to push people to a certain behavior. It’s generally elegant but warrants discussion.


    1. Laziness isn’t the right word. Negative connotation. I need to think a bit more on this one.

  4. Unique. Meaningful.

    These 2 words have been guiding lights for me in recent years. As I grow up, I find myself returning to these qualities when I am evaluating, reflecting, understanding, and planning aspects of my life.

    Primarily, these words guide my work. Indeed, it applies to family, hobbies, writing, vacations, charity, romance, and more. But since i tend to jump from topic to topic…let’s focus on how it applies to work.


    Early on in life, I decided I never wanted to be a cog in the machine. Maybe it was Youngest Child Syndrome that drove my need to be different. Indeed, I recall going to dinner with my family when I was younger and deliberately changing my order if someone before me ordered what I had planned to order. Indeed, this seems foolish! Why degrade your choice to something worse, or budge from your plan, just to be unique? This is a different conversation for another time, but I just felt like I needed to be different. Plain and simple. Maybe it was working a summer job (like my management consulting internship) that sucked the life out of me and affirmed my commitment to not being a cog. “Never do the work that someone else could just as well be doing if you weren’t there.” is what I thought at the time and what motivates me to this day. Indeed, that only carries you so far, since after all, being a truly special snowflake is hard, and frankly, if I weren’t say, building the company I am building today, it’s indeed very possible that someone else would be. Definitely? Not necessarily. Build it in the same way? Unlikely. So, I proceed.


    I like to spend my time well. I believe we are entitled to a limited amount of time on earth to make an impact. Why waste that time doing meaningless work? This is why I couldn’t work most jobs. I personally couldn’t derive meaning from most jobs. What is meaning? Who knows. Sometimes it’s just helping people, sometimes it’s changing how people think, sometimes it’s saving lives, sometimes it’s solving a challenging problem…everyone defines meaning differently, and I think it’s how a lot of people get by. We rationalize meaning, so that no matter how meaningless our work truly is, we find value and meaning it. After all, a life without a purpose is quite depressing, no? Anyways, I like my work to be meaningful.

    Putting It Together

    Work that is just unique doesn’t get you far. I could dress up like a clown every day and run around - that would be somewhat unique. Meaningful work also has its limits - I could be a doctor and help people every day, deriving meaning from saving lives. But for me personally, I need both. I need the unique, and the meaningful. And hey, it’s all in the eyes of the beholder. To be skeptical, I would look at my life derisively and say “A tech company founder in San Francisco…” ha! The furthest thing from either unique or meaningful. I don’t see it that way. To me, that’s an uninformed dismissal based on a stereotype perpetuated in the media and fueled by ignorance. But hey, everyone is entitled to their opinion, truly.

    The Guiding Lights

    It frustrates me that most of my peers don’t have a perspective on what they want out of life. Maybe it’s none of my business. But you have one life (barring reincarnation!) and how can you be decades into it with no insight on what you want? You know you want a burrito for dinner tonight but not what you want to accomplish in life? Of course, defining what one wants in life is complex, and ever-evolving, and it shakes one’s foundation to lack a clear answer. But it’s not about final answers and narrow definitions of what one should be doing when he or she is 50. But rather guiding lights. For me, those are “unique and meaningful”, driving me towards a place of intellectual and professional freedom and personal and social impact. More on “Freedom and Impact” another time…

    PS - I intentionally am avoiding formatting this beyond headers and paragraphs. This post is not meant to be scanned :)

  5. Today I was gazing out of my office window.

    What I thought:

    Police car. Lights on top of police car. Wow, those look old. Why haven’t those been replaced? Oh, well, I guess those lights are…

    Good. Enough.


    Why replace them? Oh, yours have GPS on them? That’s cool. Not replacing them. Oh, yours are integrated with crime reporting? Cool. Not good enough. Oh your lights last 10x longer? Cool, mine aren’t broken yet.

    Innovators often focus on their solution, convinced that their solution is better, rationalizing the entire feature set around the premise that it’s better than the competition. It might be, but see it from the other side.

    And yes, startup folks love to talk about a solution needing to be 10x better than the incumbent to justify switching costs. But that cliche loses meaning without truly, deeply understanding a person’s psychology, naturally.

    I reached the conclusion that the police lights didn’t need replacing on my own. This was easier because I am not selling anyone police car lights. But if I were, I’d have a much harder time being rigorous about what’s worth replacing and what’s not. Keep this in mind with your own product.

    Understand this point of view. It’s the only way you can be honest about the value your product can deliver.

  6. I saw this tweet and it bugged me.

    Big companies say “We missed mobile.” …”We missed the Internet.”

    OK, everyone, and all organizations as a collection of people, are fallible.

    But saying one MISSED something fails to take responsibility for the role one could have played in shaping history. It’s a passive response.

    Trends don’t appear out of nowhere. It’s not like a surprise shooting star you didn’t run fast enough outside to see. Trends, sure, pop up some times. But mobile. The Internet before that. The PC before that. These are not overnight quirks that arise. Wrinkles you can iron out. These were important technologies that people were working on for years and years before they went mainstream. Reputable companies can participate in those processes. Indeed, they could be at the heart of them the way Bell Labs was in its day.

    Sure, one can rationalize this as classic Innovator’s Dilemma. But until companies and leadership stop saying and acting like they just missed trends, and start realizing that they should be more mindful of shifts occurring long before the shifts go mainstream…then big companies are going to continue to miss huge industry shifts.

    Maybe that’s fine. Makes room for new entrants. And if you can’t be constantly getting better and defining the future, you don’t deserve the lead your industry. But it begins with attitude and big companies could probably benefit from a more anticipatory than passive stance.

  7. As I may have mentioned, I’m reading the book Thinking, Fast and Slow right now. One main premise is that there we act based on 2 systems: fast, intuitive thinking (System 1) and slow, deliberate thinking (System 2).

    The author, nobel prize winner in economics Daniel Kahneman, also briefly covers the idea of strolling early on the book. I am a fan of strolling. Walking quickly has never suited me, because I just enjoy strolling. I haven’t articulated why exactly I favor strolling in the past or understood it. I never thought too deeply about it, but I also don’t know if I would have had the words for what Kahneman explained.

    My interpretation of what Kahneman says is that strolling is better for thinking. Your mind and body share some resources. So, when there is less strain on your body, you’re more able to think. And by think it’s not about how your mind wanders when you’re running 10 mph on the treadmill and you clear your head.

    But concentrated, focused thinking. He argues that System 2 needs resources to do what it needs to do. If it’s distracted, it defers to System 1, which is arguably less sophisticated in the realm of critical thinking.

    Anyway, I love it when I read or hear or see something that helps me understand myself or the world around me better. I think I understand now why I enjoy strolling.

  8. I’m currently reading Thinking, Fast and Slow. Among other ideas, it’s made me wonder why people are drawn to contrarian ideas. I’m not certain that this premise is true (“people are drawn to contrarian ideas”), but I have observed this to be anecdotally true. (This is an advantage of writing a personal blog vs. an academic paper. I don’t want to spew misinformation, but I like spending more of my time jotting down ideas and us riffing than finding 10 citations just so I can say what I want to say).

    When someone says, “You know, buying a house isn’t all it’s cracked up to be.” anyone who was thinking about buying a house, or believes buying a house is a good investment, is listening. Indeed, pro-renters may listen as well given confirmation bias. Or when someone says “Tech stocks are surging now, but next week things may turn downward.” Or “Drinking water is actually bad for you.” This makes people’s ears perk up.

    Some reasons to listen include:

    • Relevance - if you’re a home buyer, of course you want to consume information relevant to an important part of your life. Whether you agree or disagree is moot.
    • Intrigue - I believe there’s a tendency to be drawn to things different than what we know, or things we don’t understand. Contrarian thinking embodies this property. Indeed, we also fear it because of cognitive stress it burdens us with. So there’s 2 sides.
    • Fear of Missing Out - If water really IS bad for us, then we don’t want to miss out on knowing so.

    This last piece is what prompted me to write this post. I’m of the belief that most people ascribe to herd thinking. We follow crowdsourced star ratings of venues and media (Yelp, Netflix), we read articles an algorithm suggests are most popular (Facebook), we vacation where friends, family, and the media suggest (How did The Bahamas get so popular?)…this is probably a facet of human condition that various technology and media have simply acknowledged.

    But stronger than the ease that comes with joining the herd, is often the anxiety associated with the fear of missing out. And thus, when someone posits a contrarian idea, we don’t want to miss out on the insight or knowledge they’re sharing. Or the benefit that can come from following what they say. And after all, we’re still able to follow and not have the burden of being the decision maker on us, so the onus of original thinking remains elsewhere (the contrarian), but people still get to be sheep — just running with a different, perhaps smaller herd.

    Anyway, maybe this is rambling. But I have long found contrarian thinking seductive. Someone contradicts the reality that I know, and I want to know more. I think it has to do with a fear of missing out. What do you think?

  9. I’m somewhat OCD. The whole ‘hanging off the top right corner’ and the glaring red discomfort me on a subconscious level. 


    It’s unnecessarily complex and obtuse. Right?

    Here’s a slightly more stressful example:image

    So, what if the count was contained but the icon could still seem differentiated? And the brand identity of the icon could be preserved?


    This was a 4 minute Sketch mockup. But what do you think of it conceptually? If I spent more time on this, only the icon itself would have the opacity (not this weird rounded rectangle around it), and I would play with the weight, color, and general treatment of the count. What’s good and bad about this approach? Maybe I’m crazy.

    Or maybe this (because the pro of all the differentiation breeds the con of all the noise): 

    Who knows? Happy Memorial Day!

  10. In San Francisco these days, it feels like class warfare. Techies vs. everyone else. Specifically, there is a growing resentment towards technology, entrepreneurs, and venture capital.

    Rather than getting distracted but the many facets associated with that conversation, I want to focus on a specific scenario. Anti-tech people (I’m being lazy and avoiding a better, nuanced term) protest symbols like the Google bus and others and decry the effect of technology on the Bay Area, etc.  - rising rents, an increasingly homogenous and exclusive culture, etc. 

    (Disclaimer: I use anti technology and pro technology as really lazy, oversimplified terms throughout this post. Please forgive me; I choose to allocate my time to other things right now than nailing the identities of those populations in some more articulate fashion.)

    In response to this, many technology people point to the irony of such people who organize via Facebook and snap photos of their dismay through their iPhones. “Look! You’re using the very thing you decry! Hypocrite! Let’s not listen to you.”

    This brings up a theme I have long thought about - hypocrites aren’t necessarily wrong, they’re just hypocrites. When I call a friend, family member, or anyone else in my life stubborn, a fair reaction for them to have is “Look who’s talking.” I am indeed stubborn. But that has zero material effect in the accuracy of my original statement, when I call someone else stubborn.

    So back to the original point. “Anti-tech people” are not wrong about their dismay about the state of things in San Francisco just because they use technology. What do we expect? Are luddites the only people we’re willing to listen to / who have a valid point? That’s absurd. Not only is it absurd, but luddites are likely less able to relate to anything a “pro-technology” person says because they’re less aware of technology and its benefits. Thus it’s damaging to only listen to anti technology arguments from people who are anti technology. So then if we agree that luddites aren’t the only people entitled to anything less than a positive view of technology, we can’t hold it against people when they use smartphones and Facebook to communicate. Technology has indeed become, as it always has been, a fabric of how people do things.

    So, point #1 - hypocrisy doesn’t invalidate the accuracy of someone’s point. (It just makes them less credible. But relying on credibility to be any more than a proxy for accuracy is a misappropriation of what credibility is intended for. e.g. You generally trust what a source like the BBC publishes. This is because they’re credible. But that doesn’t dictate truth in 100% of what the BBC prints.)

    Then point #2, antagonism stifles understanding. When “anti-tech people” and “pro-tech people” antagonize one another, it shifts the other party into defensive mode. In this mode, people can proactively reach understanding. They disparage each other. This doesn’t help us reach a place of understanding. This doesn’t fix the problem. This is true of political conflicts, such as the Israeli - Palestinian conflict. This is true of social conflicts, such as gender equality. This is true of socioeconomic conflicts, such as the current class warfare we see in the Bay Area.

    So how do we avoid antagonism? I’m not bullish on this happening. People are people. A stone is thrown, someone’s feelings get hurt, they get defensive, they attack the other party, the other party defends, then they attack, and so on. Only when a third party mediator, or a celestial meteor, intervenes, or the parties are exhausted (or some other event occurs I’m unaware of), do things calm down. But if we could figure out how to be more conciliatory, I imagine things would be better and we’d reach a place of understanding much faster. And we need to. Because otherwise the Bay Area is going to change for the worse over time.


Jason Shah

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