Career Archives

The Story Behind My Investment In DoorDash

After investing in Instacart, I started hearing about many other food-related startups. I will admit that I wasn’t interested in learning more about this category, and even when I first came across DoorDash (as they were starting to raise their seed round), I used the service (and was very happy with it), but didn’t think it would be a suitable investment for me. I kind of dismissed it.

But, that was quite short-sighted of me. There was something going on that I didn’t understand on the surface, and because I didn’t stop to think about just how they were doing this, I let my biases take over the rational part of my brain. Luckily, one of the company’s seed investors is a friend, and we hadn’t caught up in a while — about 9 months earlier, I had a kid, and then he had his second kid. During that conversation, he mentioned that there was some room for individuals in DoorDash (which he invested in), and that I should meet the team..

I met with Evan and Tony, two of DoorDash’s founders (the other two founders are Stanley Tang and Andy Fang), and told them what I’ve already written in this post. They then shared more about the genesis of the business, and how they set it up all the processes and operations. It was very impressive, and I felt like an idiot for not using my imagination earlier. The imaginative piece I was missing was how DoorDash was building three different types of software products (for delivery people, for consumers, and for the restaurants), and then tying them all to their own custom back-end systems. Or, I didn’t think about how they could actually use data to estimate demand and help restaurants get more business. I slept on it, and then asked for permission to invest. They said yes.

Since then, DoorDash has been growing like a weed from its Palo Alto HQ, expanding in a more southwardly direction and operating on all cylinders to keep up with demand. The team has definitely figured out an operational model which works well for lunches and dinners — and now the even harder work awaits about how and where the company will expand its model. Tony, Evan, Stanley, and Andy most certainly have the potential the guide the company to a huge outcome, and I’m lucky to get a little seat to watch it unfold.

Some other interesting notes about this deal. One of the lead seed investors who broached the idea of me investing did not have to invite me. As venture capital resources increase, it triggers competition and more pressure for firms to take as much as they can in certain rounds. In this case, the investor and founders kept a small piece open for someone like me. That is an opportunity and responsibility that I do not take for granted.

The Story Behind My Investment in BOND

This one is both personal and random, and also not neat and clean. Before I got involved in helping found a life sciences company in Boston (circa 2009), I had an idea around a startup in the gifting space. Mobile had just emerged, but we were thinking web. I didn’t know what I was doing, and after a while, it didn’t really go anywhere. Yet, I thought about the kernel of the idea for a long time. You could say I was passionate about it (and still am), but didn’t have the product sense to articulate how it would live in the real world.

Fast-forward five years later, and I got one of Eric Kuhn’s weekly emails about new products he’s seen, and there was BOND. I read the description. Damn! That was the idea, but this guy actually did it. I asked Eric for an intro, and found out that one of the early employees worked with a close friend of mine. I started a conversation with them while at the same time conducting some light “people diligence.” Many of these early-stage deals often require this as the most important piece of diligence.

Even though my gut wanted to invest, I held back a bit. Something wasn’t quite right. I wanted to make sure I was on the same page as the founder about a few things. But, it was kind of a hectic process, he was in NYC, and I was in the Bay Area. I almost decided not to do it, but then I got over the hump and joined the round. Since then, the company has had to go through one critical stage where the market forced it to focus in a way it hadn’t before.

Some people at the company had to go. The team got smaller. They had to turn away some business and focus on specific lines of business. There weren’t many email updates, so when I got one that kind of concerned me, I called him up. It wasn’t an easy phone call. Luckily, since formally working with the company, I had gotten to meet Sonny (the founder) and hang out. What impresses me most about him, as a person, is his willingness to have hard, frank conversations. I told him I wasn’t thrilled that he didn’t ping me sooner as he and the product were starting to feel pressure. But, I can understand. I wanted him to know that even short, weekly updates about vitals are helpful to maintain an environment of “no alarms, and no surprises.” That’s from a Radiohead song.

In about a week, Sonny turned it all around. He had a new plan. It wasn’t a pretty plan, and he was patient with me, and now looking back on it, he made the right move given the circumstances. And, the plan is constantly getting better, as if he’s hit his second wind, though we’re not out of the danger zone quite yet.

When I originally invested in BOND, it was selling a product to both consumers and companies. Now, it has to focus on the company and API side, and it is, and I think Sonny has the right disposition and passion to guide the product and business in creative ways.

It’s been a great learning experience for me, and I hope, for him. The root of the product — to help make gift-giving easier — will always be the driver, and I believe it is a both a B2B and mobile commerce opportunity that has huge, mass consumer appeal. The root is to build technology that helps people make their relationships better-strengthen their bonds.

Just like individuals want to tap an app and get a car or taxi, we believe they’ll want to send gifts to clients, coworkers, and loved ones in this manner, too. That’s the goal. It’s early for Bond. The road has already been bumpy, and in the seed stage, there is no lead investor. Sonny is a single founder, a husband, a dad. It’s a lonely world out there for a solo founder, but I believe Bond will make it less so, and that’s a worthy enough mission to aim for in my book

The Story Behind My Investment In Sidebar

In 2013, a particular twitter account started popping up in my feed more. This user was crafting tweets and linking to blog posts about mobile, and they were really good. As someone who thinks about mobile every day, in work and for writing and investing, I was intrigued. And, it turns out he was in Palo Alto. Interesting.

He wrote a short post on push notifications that motivated me to write an entire weekend column on the topic. I think he started reading my blog, and we started going back and forth on twitter about mobile. (Now as I’m writing this, it sounds like we were courting each other! LOL.)

Anyway, we met up a few times and I told him my interests, and he started talking about his new company. As a second-time founder and someone maniacally focused on mobile, he shared a great vision for his next company, but he didn’t have a product yet, and it was really early. I didn’t care. I wanted to invest.

The reason I was comfortable making a bet on a person and an idea is that Ariel Seidman, the founder of Sidebar, appeared to know a lot about something that most other people didn’t know. First, everyone was trying to go after consumer mobile. Ariel wasn’t. Those who weren’t focused on consumer focused on enterprise, in the traditional sense. Ariel didn’t. Instead, he wanted to leverage an insight he had from his first company to guide him as he built a product for the second. The result is a focus area that I have yet to see in mobile, and I’m damn excited about that!

Ariel and the team are working quietly with customers and building. I know he’s intensely focused on this company and his family. That’s it. He’s so particular about every decision he makes, I always know that any decision is thought through, fully — including this draconian decision to unfollow everyone on Twitter (including me!) and instead following only 4 or 5 accounts, like Duke basketball coach Mike Krzyzewski.

Back in the fall, we were both invited to speak on a panel at a small mobile event in SF, so we drove up together (my car was in the shop), and we just started talking about our paths through the Valley. He’d been here for a long time, and I, pretty new. He told me all about this first company, and how he selects investors. I told him about my interest in investing, in quite a bit of detail. He listened closely. I’d describe it as mutual trust and respect, not built over years, but pretty quickly given our interests and goals, forged over Twitter and blogs.

One Tactical Path Into Working On Product

I don’t know why, but I get this question a lot: “How do you get into a product role?” Well…

I am not the most-qualified person to answer this, yet I’m receiving this inquiry now about 4-5x per week, so I’ll offer my two cents on what I’d do:

  1. First, find a product, or few products, that you truly love. True love means that you use them daily, or at least 3-4x per week.
  2. Start taking notes on each product, especially the elements you love and the elements that frustrate you and/or you’d change.
  3. Start collecting feedback from other people outside the company that makes the product, and try to record it in some structured fashion. For instance, this means going through how others onboard in the app, what pieces may be broken, or confusing, and so forth.
  4. Unify this information and take it to the company, so that you can structure your conversation (or interview) with them around the product. This is critical because it will help differentiate you from others who just want a job, it will help filter out companies or people that don’t value this kind of engagement, and you’ll learn through the process, even if you don’t get the first or second gig.

Ultimately, the reason #4 is important is because it sets the tone for a conversation that is not about you or what you want, or about the company or the person you’re talking — it’s about the product. In that discussion, if you can’t show a mix of enthusiasm and depth about digging into the specifics (even just from a user’s perspective), it means you need to do more investigation. I was able to shortcut this because I had the fortune of being at a venture firm for six months and invited mobile founders to come in and pitch all day, nearly every day. Without that, there’s no way I would’ve been able to talk to the Swell folks about radio and podcasts, and to start building a relationship with them around product feedback. That’s how I’d answer the question, but take this with a grain of salt. Good luck!

Thank You, NYC, From 35k Feet

I’m on the plane early headed back to SFO, and now that I’ve shifted my airline loyalty from United to Virgin America, treating myself to some WiFi while the seat next to me is unoccupied. This was a very quick trip to NYC. I wish it was longer but it’s hard to be away from a certain little critter at home. As I’m half awake and preparing to dig back into email on this flight, I can’t help but reflect on how much fun I had on this trip to NYC. For the past few years when I visited NYC, it was always around a holiday or during some rushed event. This time, my goal was just to hang out with a few people and enjoy myself, hang out with family, and have a bit of time to myself. What I can’t get over is just how open and inviting everyone was in NYC. I used to live in NYC years ago, but was in a different world. So, I’m always comfortable in NYC and on the subways (but not super-crowded areas), but on this trip, all of my friends went out of their way to accommodate me and make me feel welcomed, almost as if I was going home again.

In no particular order, thanks to David and all the entrepreneurs from the Columbia network for our breakfast meeting earlier this week; a big thanks to Shai for putting together a big interactive mobile meetup with Steve, Sarah, and Jordan, and thanks to Ryan, Chris, and many more for attending and participating (aside: here’s a terrific, detailed summary post on the event by Cezary Pietrzak, good details for mobile founders in here); was great to just hang out with Zach, Albert, Andy, and Brian, and to Steve for bringing even more great people into the fold last night for drinks — I had a blast, and I’m already planning my next trip to NYC in my head. Thanks for making me feel like it was home.

Language And Leverage On Twitter

If you’re reading this, you know I tweet often…a lot. I’m approaching 60,000 tweets, after opening my twitter account in mid-2008. Despite the noise I create, twitter has been critically important for me to shape and test my ideas, to share my ideas with others, and to meet other people across networks interested in technology, startups, and investing. Recently, I found that I made a list — I know what you’re thinking, “Lists are silly.” They usually are, but this one seemed different. It was created by a startup called PeerIndex. They picked about 75,000 accounts in the space of technology, startups, and venture capital, and then monitored how all 75K accounts shared content and interacted with each other in order to find which accounts drove the most attention and influence. [Click here to see the full PeerIndex list and methodology.]

The list is below, and while I did come up on the list, I thought it was a better exercise to show how the top accounts stack up in terms of number of tweets and number of followers — note, the study did not take into account the number of followers a person has, so that anyone can move up (or down) on the list over time.

For me, that was the insight, that despite the noise I create on twitter, it is an important medium to participate in — it is through twitter that someone like me, with very limited experience, was able to learn, interact, and be a small part of the conversation with some of the most-respected minds in technology and investing on the medium that commands everyone’s attention today.

And, as someone who loves language and words, I wanted to list out the Top 10 accounts and briefly unpack the style in which each person uses this medium to their advantage. Naturally, nearly everyone on here is a current investor, analyst, writer (some all of the above), as most operators wouldn’t have the time to do this — Levie being the exception. As you’ll see, the styles are very different — of course, this isn’t a list of real “influence,” it’s only looking within twitter so it’s imperfect but fun nonetheless:

Aaron Levie (~2,700 tweets, 94,000 followers)
Levie has won twitter through humor, mixing the timeliness of pop culture news with a smart brand of nerd swagger. His tweets are so funny and/or insightful that they’re retweeted and favorited at a high rate each time. He focuses on broadcasting, using interesting images, and doesn’t engage in @replies or conversations.

Marc Andreessen (~12,000 tweets in less than 4 months, 96,000 followers)
Out of nowhere this year, Andreessen decided it was time to tweet. And, wow, he’s extremely active and engaged. He also replies to many and favorites tweets all the time, each time firing a signal to the creator as if to say “Marc Andreessen is listening.” He’s almost branded his signature “1/…, 2/….” tweetstorms (which are mini blog posts), and naturally, everyone pays attention to him because of his extremely high influence based on outstanding career contributions (Netscape, a16z, etc.).

Hunter Walk (~20,000 tweets, 61,000 followers)
Walk smartly mixes links to his site and firm (which contains his original content) with fast-paced, news-driven @replies with nearly everyone in the community. As Levie uses humor to cut through the noise, Walk uses transparency.

David McClure (~49,000 tweets, 207,000 followers)
McClure is high-volume, with brash tone, and lots of conversation. Oftentimes, it can feel as if he’s sharing his inner-most thoughts, fuck-ups, controversies, and all highs and lows with everyone. He’s also cultivated a truly global audience through his global firm, 500 Startups, which helps him have a broader network (geographically speaking), which help him spread his ideas. You could say McClure wears his heart on his tweets.

Benedict Evans (45,000 tweets, 31,000 followers)
Evans is a long–time mobile thinker, consultant, strategist. He’s expert at thinking about the mobile technology landscape, so good that he was discovered by Andy Weissman, and investor at USV in NYC. In turn, Fred Wilson wrote about Evans regularly, and Evans grew his tech readership, and has now been hired by a16z. Evans uses twitter to think out loud, as if he’s forming his next blog post in his head, a deeply analytical feed which engages selectively.

Om Malik (~37,000 tweets, 1.38M followers)
Malik is the experienced, old-school journalist, gumshoe, reporter, and now investor, a long-time tweeter with a big audience, the former head of an influential blog and series of conferences around the world. His feed is mainly about curation, about using his experience to signal what is actually important in a noisy world.

Paul Graham (~1,400 tweets, 161,000 followers)
Perhaps one of the truly most influential people in the space, online and everywhere else. Anything PG tweets or links to is analyzed. He has generated a movement and uses twitter to curate a few things, share notes about companies in YC that are doing well, or use his influence to share thoughts about the ecosystem, especially through his blog.

Brad Feld (~25,400 tweets, 168,000 followers)
Feld is an OG entrepreneur and investor, and is very active on twitter, sharing links to his ideas, books, blogs, and more. He’s built up an engaged audience online, but also offline through his evangelism of the power of offline community building, which in turn translates into more attention online.

Fred Wilson (10,300 tweets, 327,000 followers)
Again, OG investor and tweeter, one of the original investors in twitter and a board member there. Like Paul Graham, a must read for everyone in the industry, though he doesn’t tweet often, choosing instead to link to his posts daily — and less of a broadcaster.

[no title]

I don’t know why, but two unrelated ideas/themes have been on my mind…no title to this post, because I can’t think of a good one…

The first is about “entrepreneurial journeys.” I know, that is a cheesy term. Believe me, I cringe writing it. Anyway, semantics aside, this term came up in an interesting conversation I had with a close friend. We were discussing how we both haven’t seen a close mutual friend recently. This friend is building his own company, his first time in a founding/CEO role. The conversation ended with something like this: “Well, Semil, I guess he’s on an entrepreneurial journey.” I don’t know why, but that phrase has stuck in my head. It’s slightly different than saying “he’s building a company,” or “he’s really busy,” or “entrepreneurship is all-consuming.” As I’ve been thinking on this, it struck me that everyone in and around technology startups are on journeys of different speeds, directions, and arcs. Even though so many of the people we know best who are all crammed living in proximity to each other can actually drift apart because the trajectory of the journeys each person can be very different. It’s like a diaspora, of sorts, excepts the physical distances traveled aren’t great — but in the mind, those distances can feel vast.

Now, next, unrelated…

The second thing that’s been on my mind is about the word “empathy,” particularly in the context of what I hear (and read)  founders discuss they want in their investors. Disclaimer, I’m no expert here and have limited experience. Caveat out of the way, it seems most people equate empathy with having been a founder/CEO of a startup before. Unfortunately, I’m not sure that’s true in practice. In the dictionary (Merriam-Webster), “empathy” is defined as the feeling that one can “understand and share another person’s experiences and emotions.” The ability to share understanding is important, but longer-term investments seem more like business partnership, and the good ones seem to be more driven by an honest alignment of interests among both parties versus whether one side is empathetic or not. Empathy may help in the sales process of investing, when an investor courts a founder. And if empathy is important (to a point, right?), it can be gained in different ways in and around startups. Some investors with deep operating experience (but no founding experience) can breed their own style of empathy; some investors without any real experience whatsoever can build empathy as they continue to invest; some people pick up empathy by doing something hard and getting their butts kicked, repeatedly, and surviving; and some investors who have been founders even more than once may not be empathetic as investors. On a different plane, empathy can also be gleaned from trying, difficult experiences.

And while empathy may work up to a certain stage or maturation of a company, after a while it may diminish in utility — think, for instance, of entrepreneurs who have shepherded their company through a Series A round only to be stuck without Series B offers — at that point, “empathy” doesn’t really creep into those conversations. Of course, people are human about those discussions, and some of those discussions can be hard, but empathy only goes so far. Empathy is something folks to should ideally show to everyone — not just investors in a sales process with founders, or founders managing their key employees. Empathy is cheap to deploy. It’s quite cost-effective. What isn’t cheap is a partnership where parties’ interests are aligned. Sometimes that means difficult conversations. Sometimes empathy may take a back seat to the truth — even a harsher truth the investor may need to hear from a founder. Anyway, I know everyone talks about “empathy” and I know it’s generally important on an interpersonal level (way beyond startups), but it has lately struck me as an abstract word people think they want or need, perhaps distorting reality — a reality we all need — as a cost.


Screenshot 2014-03-19 16.02.39

For some reason, people approach me about something I’ve written — recently or in the past — and often assume whatever I write is “widely-read.” They assume what I write here is influential, by some measure. I respond by dispelling these beliefs. Usually, the other person doesn’t believe me, but it’s happened so often recently, I wanted to look at the data and see for myself. And, it’s true…not even 1,000 people, on average, visit my site (and about 450 subscribe via email). That’s kind of pathetic when one considers how many tens of thousands of people visit Hacker News or AVC on a daily basis. (I also write a weekly column on TechCrunch, every Sunday morning. Usually those don’t generate much traffic, either.)

Look at the chart above. I redesigned my blog to start on July 1, 2012. A few things are apparent. One, traffic is pretty low! Two, the first spikes are only the result of a very famous investor who linked to one of my posts and it went viral on his recommendation. Three, what I write isn’t evergreen stuff — it may be relevant for a day or two, and then decreases in value — some of it may not have value to begin with. For the amount of time I do put into it, the ROI is pretty bad.

That’s OK though. Despite what others may perceive, I have never written blog posts here “to build an audience.” I write because I have to, because if I don’t, my brain will go into a frenzy and eventually rot. And, when I write, I try to think of just one person who’d want to read it. That’s all that matters to me. A friend told me this was “narrowcasting” — kind of like broadcasting, but to an extremely narrow segment. I’m cool with that. In fact, I prefer it. Thanks for reading!

Well Done Versus Well Said

Do you ever hear a phrase, unattributable to anyone specific, and then it just rattles around your brain over and over again? Well, it happens to me all the time (unfortunately). And, when something rattles around my brain too long, I need to write it out. Until it’s written, the thought isn’t crystalized. A few days ago — I can’t remember where or whom — but I either heard or saw this line: “Well done is better than well said.” It didn’t register at first, but then it took root.

“Well done is better than well said.” In today’s culture, “well said” gets most of the attention. We judge potential political leaders on how they debate, their stump speeches. We listen to talk radio, television news shows, and more, judging people on what they say. In the startup world, the competition among investors to differentiate capital and gain mindshare with founders is so intense, some investors are turning into little media brands, full with books, conferences, and other media assets.

In today’s startup world, many things are “well said.” But, what is “well done”?

As someone who keeps an active blog, engages often on Twitter, and speaks at events, I too am a small part of the “well said” crowd. “Well said” has its advantages. It is not a bad thing. For instance, it opens doors that once may have been closed. However, “well said” does not directly generate or accrue market value. In order to generate market value — or, put another way: what does the market truly value? — something has to be “well done.” I don’t mean this in the sense of being fully-baked, or cooked through, or over-cooked. I mean, it has to not only be done, but done well.

Done well.

What is done well? Uber, which started in one location, now seems to operate in nearly 100 cities worldwide. Dropbox has made, at scale, a seamless cloud-based storage service that could power the world’s next killer applications. Snapchat handles close to 500 billion images shared across various networks per day. Those are jobs done well. Investment firms like Sequoia and Benchmark, who have resisted today’s era of VC marketing/blogging, deliver some of the best returns in their investment classes. And, the market responds to it. When something is “done well,” it usually has nothing to do with that thing being “said well.” Yes, using clear language to communicate within, across, and outside of a company is very important. No doubt. The distinction I’m trying to make here — as someone who may say things “well” — is that things that are well-said are nice and have value to some degrees, but things that are “done well” are, at the end of the day, where value rests. It’s something I’m reminded of every day as I slog through the Valley.

The WhatsApp Story Challenges Some Of The Valley’s Conventional Wisdom

It’s rare for one of my weekly columns to go viral, but this one did. Would love to hear your reactions…

Silicon Valley and the tech world at large are filled with a variety of conventions. These conventions are now created, captured, and shared ad nauseam disguised as blog posts, tweets with links, and countless message boards. The benefit of such a canon is we all have access to a rich repository of knowledge — the cost, however, is we all, perhaps unwittingly, are exposed to the same suite of playbooks, which contain the same conventions, which could, if we’re not paying close attention, and especially when amplified in an echo chamber, trick us into believing a certain reality which, in turn, script our actions and lives down a path of predictability, or worse, mediocrity.

Like many of you, the entire story around WhatsApp’s acquisition this week has captivated my attention. It might be easy to quickly dismiss this whole event as an extreme outlier (which it is). Of course, this is a big outlier event, but that doesn’t mean it shouldn’t be examined. The reality is that this week’s news was like Haley’s Comet, a once-in-a-lifetime event where everyone who works in and around startups stopped what they were doing, went outside, and looked up at the sky to catch a glimpse of something they’d only read about online. In situations such as these, my mind scans back over all the “lessons” or conventional wisdom that swirls around the atmosphere, and the story of WhatsApp does call on us to examine and challenge (yet again) some of those conventions:

“Yahoo! doesn’t have talent.” For a variety of reasons, Yahoo! gets beaten up by the press and in social media. The company has problems and is working through them, but as a result, employees and alumni have kind of been a soft target. The two WhatsApp founders worked at Yahoo! They built a native mobile product at scale, across many mobile platforms, and assembled a team to build a complex, global telephony system.

“Companies like Facebook have the best talent.” One of the WhatsApp founders applied for a job at Facebook and was rejected. I’ve seen countless startups get star-eyed trying to recruit “so-and-so” from a big name company, but all that glitters isn’t always gold.

“The center of gravity for consumer products has moved north from the Valley to San Francisco.” Well, that’s largely true, but WhatsApp remained headquartered deep in Silicon Valley. They didn’t even have an office sign. Hidden from the city’s bright lights, the company didn’t seek out PR coverage or any of the other trappings in today’s startup lifestyle culture.

“The best founders are relatively young.” The WhatsApp founders were in their mid to late thirties.

“Mobile products should be delightful, beautiful.” I often shudder when I hear this refrain. Of course, apps should look nice, but at minimum, they should work to solve some problem or provide some service or entertainment. WhatsApp simply worked for people. It didn’t have fancy features. It solved a problem at scale, building products for the following platforms: iOS, Android, Blackberry, Windows Phone 7, Nokia, S40, Symbian S60, and others.

“Be mobile-first, build for iOS and Android.” The Whatsapp team took on the challenge of building products for all sorts of phones, many of which readers of this blog wouldn’t ever touch, even those running J2ME on older Nokia and Samsung handsets.

“Personal branding is important.” The WhatsApp founders did not have any personal brand. I would guess if 1,000 tech insiders were polled, less than 5% could’ve named the founders or anyone at the company.

“Preserve your startup’s equity.” In my opinion, many early-stage founders over-value the equity in their startups. Yes, a lot of sweat, blood, and tears go into starting even the smallest outfit, but an environment so competitive for products and so fragmented for talent, what was once conventional in terms of equity for early or key hires may now be outdated. Given this, I respect Zuckerberg’s aggressiveness to give up a really large chunk of Facebook to partner with WhatsApp, and to add one of WhatsApp’s founders to his Board of Directors. Instead of hoarding this equity, Zuckerberg realizes he must partner for the battles ahead.

“Don’t worry about making money, just grow big.” WhatsApp did both. Depending on what platform a user downloaded the app on, WhatsApp would charge them about $1 or, at times it was free — they also charged a $1/year subscription fee after the first year. WhatsApp was expensive to run, so it wasn’t breaking the bank in revenue, but they at least had cash flows, and one might conclude from this that such inflows helped them pace their operations and not get enamored, enveloped, and distracted by the pomp and circumstance of a modern-day fundraising process.

There are more conventions that were broken here. How about the fact that WhatsApp was a tiny company compared to their footprint, at only about 50 employees, mostly split between engineering and support? Or, how one of the Valley’s most successful venture firms — Sequoia — was quietly the major outside investor across a few funding rounds at the company, electing to not use their networks and celebrity to announce such deals or trumpet the company’s growth trajectories? Or, speaking of venture, how this particular VC firm missed the first wave of social networks, invested a large sum in the debacle known as Color, and then, in about three years’ time, turned their investment in WhatsApp into one of the great IRRs in the history of venture capital?

There are countless angles to examine, but the meta-point of this exercise is to use this rare, brilliant event to briefly hit the “pause” button and reexamine if we ourselves or our products or our companies are following a conventional path, one we’ve been told, or exposed to, or read somewhere.

I’m not suggesting we throw out all the rules and engage in chaos. But, it is a good time to reexamine them. Do we take these conventional biases into our work, into our lives? Do these conventions inform our recruiting strategies, our paths for monetization and/or growth, how we think about product design? It’s easy to start to believe something once you’ve heard it enough, or if it shows up in your Twitter feed often. It has to be true! Or, perhaps not…perhaps WhatsApp became a mega-outlier because it either consciously bucked or unwittingly ignored so many of the popular conventions we hear of today.

Haywire is written by Semil Shah, and is published under a Creative Commons BY-NC-SA license. Copyright © 2014 Semil Shah.

“I write this not for the many, but for you; each of us is enough of an audience for the other.”— Epicurus