Career Archives

The Chilly Freeze For On-Demand Startups

We will talk about this topic among others at The On Demand Conference in NYC on September 15, Register Here. We are also running our second contest for the best B2B on-demand startup, more details here!

My, how things can change. When we did the inaugural On-Demand Conference back in May 2015, everything was hot. Now, gearing up to the second installment in September in NYC, things are — shall we say — a wee bit chillier. And, rightfully so. In a few months, we’ve seen high-profile companies broadly in the sector nearly fold overnight, we have yet to see the big rollup consolidation strategies that people wish would happen, and the culture of copycat models is bringing more and more founders into red ocean markets like food delivery.

Investors are applying more scrutiny toward on-demand startups, asking flavors of the following questions: How frequent is the consumer use case? What is the payback period when opening a new geography? What do the unit economics look like, and can they modeled at scale? Does the team understand they should balance unit economics and growth by city to make sure they don’t run out of money? We haven’t seen much M&A in sector, so can this company go the distance? How can the team expand the product/service offering if the service grows? With UberEATS now in San Francisco, the backyard to many well-funded food delivery apps, could Uber crush the opportunity entirely? And, who might follow into the next round of funding should the team set out to do what they want to do?

These are MUCH harder questions than VCs were asking before. Welcome to the new world. Now, that’s not to say there won’t be some companies which continue to fetch large rounds, or that there won’t be on-demand concepts that attract funding in different parts of the world or in different product categories (like healthcare). The concept is bigger than food and transportation, though those two are clearly the consumer drivers.

Luckily for us, the purpose of these conferences isn’t to promote a sector, but rather to gather the most thoughtful minds among company builders and investors to tackle the most pressing issues of the day. So, in September in NYC, that will be no different. You can learn more about the NYC event on September 15 here, and on the VC panel in particular, friends Steve Schlafman (RRE), Kanyi Maqubela (Collaborative), Anu Duggal (Female Founders Fund), and David Tisch (BoxGroup) will debate these and other issues facing on-demand startups in the seed and Series A/B stages.

Register here for the September event in NYC. Unfortunately, I am unable to attend in September now, as I was very much looking forward to seeing everyone, meeting all the new founders with new concepts, and kicking off the day’s activities with a fireside chat with USV’s Albert Wenger, but I can’t make this trip. So, I will give away my ticket to one person who really wants to attend. What I ask for is this — tweet out a link to this event and mention me @Semil on twitter, and my co-organizers will pick one lucky winner to attend the event in my place!

Reimagining The Restaurant With Robotics

I grew up working in restaurants. I have been a dishwasher, host, bartender, waiter, line cook, and regular cook. I’ve delivered food to people, and then cleaned those tables. But, that was a long time ago. Then, last week, I went to YC Demo Day, and there were food-related robots, and it got me thinking about how the last few years has seen all sorts of innovation in modernizing or entirely replacing the concept of restaurant. This is important because restaurants provide a space and service that people can use many times a day, and critically because it employs many people, both full-time and for those looking for extra income to make ends meet.

Briefly, here are some ways entrepreneurs are reimagining the restaurant experience.

Mobile, web lead-gen: Companies like DoorDash, Postmates, OrderAhead, Caviar (inside Square) and others are funneling more orders to restaurants, and fulfilling delivery either with their own staff or via 3rd party logistics (3PL) providers (more on those below). Like Grub and Seamless, using mobile for call avoidance to order and schedule with a few taps on our phones. (Oh, and now UberEATS is in the game!)

Vertically-integrated: Companies like Sprig & Munchery make and deliver their own food, bypassing the restaurant experience entirely, but getting fresh food to customers. This allows them to control their COGS and potentially have better contribution margins, though it takes longer to rollout to new cities — that’s one big tradeoff.

3PLs: Companies like Homer, Deliv, and Sidecar offered delivery services to other businesses.

Decentralized, peer to peer: Companies like Josephine Meals envisions a future where people become home-cook entrepreneurs (a la Etsy) and sell directly to people in their neighborhood…and they may even use 3PLs to power delivery.

New Disruptors: There are too many list to here, but just when you think food is saturated, companies like Tapingo, EnvoyNow, and Fooze (among many others – and please don’t ping me about them!) are finding markets to attack.

Franchise Model: Like Domino’s Pizza, a franchise network perhaps isn’t a terrible idea to get around the cost of expansion. A company in this recently YC batch (Wheely’s) wants to help others create mobile coffee shops.

Robots and Automation: Now, this is why I wrote the post. Restaurants and the food service industry employs LOTS of people. But, now, Robots are coming! TeaBot, coffee bots, sandwich robots, and other robots or automated devices (like e la Carte). KQED had a feature on Eatsa in San Francisco, an automated restaurant. Next time you’re in the coffee shop, count how many employees are there. Probably 7-10 per 500 square feet. Why? We are used to it, but it’s entirely possible for the next Blue Bottle to just be a station of iPads and robots making your stuff. Zero human interaction. The only question is — how long will it take to come? Based on what I’ve seen this year, perhaps sooner than we all think.


Seed Founders, Beware The Syndicate Shenanigans

As any reader of this blog would know, I am a huge AngelList fan. I have run a few Syndicates now over the past two years. Most of them have cleared, but a few haven’t. I could’ve run a lot more, but I intentionally elected to be very careful about how and when I bring syndicate opportunities to the platform (1) because I’m simply new to investing overall, and I didn’t want to bring people into the fold with me too early; and (2) because I needed to learn AngelList’s platform myself, over time, and learn in between each syndicate to get better.

When I present the AngelList option to a founder, I always educate them first on all of their options for their fundraise. I like to lay out the options and let the CEO decide. Many times, the CEO has elected to forego the AngelList option, citing either privacy concerns, or signaling concerns, or wanting to wait; at other times, they dive right in, want to learn the process, and have so far been very happy.

Lately however, and why I’m writing this post, I’m encountering investors in the angel and seed stages who are up to some tricks, what I like to call “The Syndicate Shenanigans.” The classic move goes something like this, with the investor offering to the founder: “I would like to invest X, but conditional upon me taking this to AngelList and putting it in my Syndicate for 4-6x.” The founder in this case is faced with a dilemma, and this post is targeted both at the founder and also those who participate and follow Syndicates on AngelList. To be clear, these can work well if done right, but it’s smart to understand the risks before jumping into the fray:

To Those Who Follow Syndicates: First, determine if you want to automatically follow any deal of a Syndicate leader, or whether you want to pick deal by deal. If you blindly follow, your money gets priority, so just know you’re along for the ride; if you go deal-by-deal, try to understand why the Syndicate lead or founder wasn’t able to fill up the round privately. Second, generally speaking, you may want to monitor the deal pace at which the Syndicate lead is bringing opportunities to the platform.

To Founders Offered Such Terms: This may put you in a tough spot. You want the money, but the conditions attached to it could be confusing. Sometimes investors will say they have a “minimum check size” to make the math work in their own fund model, so when an investor offers to commit with the condition of bolting on a Syndicate, this is another flavor of the line: “We have a minimum check.” In this case, they likely have an economic arrangement on AngelList that gives them a percentage of carried interest on top of the money they collect for you. You have some options here. First, learn about AngelList and Syndicates, and make sure you know whether the particular Syndicate offered to you would be private or public; understand the process and how long it could take (2-4 weeks to clear); and understand how the Syndicate lead (who will be named on your cap table directly) will market your company to those other investors that you’ll never meet.

I want to be clear that (1) I love AngelList and (2) have done this myself, but (3) that making AngelList a condition of an early-stage check isn’t bad behavior, but should be done so in a way that educates the founder about his or her option, and less about throwing down a conditional on the team. Happy to answer any questions you may have and/or refer you to CEOs I’ve worked with who’ve gone through the platform for a Syndicate.

The Confluence Of Trends Making esports Go Mainstream

Like many others nowadays, I’m fascinated by the phenomena around “esports,” which can mean watching other people play video games or code or do both, either in person, or online, or on one’s phone. I had to laugh when Startup L Jackson tweeted “If one more VC discovers eSports this week & starts tweeting about it, I am going to come up with an ultimatum. And it will not be pleasant,” because it’s true…but there is good reason. I was catching up on some reading today and realized there are actually a confluence of non-connected trends which form to make the present day fascination quite logical:

One, the youngest millennials are now right in the middle of their teenage years, right around when they can almost drive a car. This generation entered the world when mainstream gaming consoles hit the market and started to invade the home, with the Nintendo Entertainment Systems coming to the U.S. in 1986, the Sega Genesis in 1989, Sony’s Playstation in 1994, and the XBox in 2001. Like I did, many folks owned or tried every system, and they popularized casual video game play.

Two, the culture around these home gaming systems is that only 2-4 people could play at a time. If you grew up around these consoles, you would clearly remember waiting your turn, and while you waited, you would watch other people play the same game you wanted to play. You’d just sit there. You didn’t have a phone to distract you or the Internet at home to jump on. Turns out “watching other people play video games” is randomly engrained in millennial muscle memory because everyone exhibited the behavior. This turned out to be inherently social behavior, waiting in tournaments to play the next round of EA Sports Madden or NHL, or trying to win Zelda or Metroid.

Three, over half of millennials grew up in an age where network TV was on the decline. Today, for many of them, network TV is wholly irrelevant. Instead, they stream content online, pay for subscriptions, buy individual shows, and watch shows on-demand. While mobile phones and networks take the place (in terms of attention) of TV, there are hours in the day folks can devote to this and they certainly do.

Four, the infrastructure required to support a range of esports activities has become robust enough to handle the traffic. People can now broadcast and/or consume esports media from home, networks like and others have cropped up and amassed large audiences. Mobile phones, data networks, and video channels are also more robust, of course. MLB recently announced it was spinning out its quietly robust digital streaming and hosting business, a unit which could be worth many billions of dollars more than it is today. As livestreaming technologies have demonstrated this year alone, social networks like Twitter are ready to provide users with live content (a la Periscope) and to support those streams as a piece of audience development and engagement.

Five, the cultural interconnectedness from a tech point of view between Asia and the U.S. is also responsible for the trend hitting the west. The culture of watching others play video games in larger audiences began in parts of Asia, which made sense because that’s where the home consoles were originally developed and released, before shipping to the west. Like messaging platforms today, the esports behavior is older and just took a bit longer to incubate here in the west, but now these micro-cultures have converged.

Sixth, the global rise in the importance of and celebrity around computer literacy is timed in such a way that it doesn’t make the act of participating in esports seem like a waste of time. Rather, it can be seen as both educational and social, as both entertainment and interactive.

And, there you have it, all of these forces put into a blender, and it all explains why esports is so popular, why sports and media networks are not only allocating mindshare and budgets to it, but also doing this for derivate products, such as gaming networks which let fans bet on esports participants, among other parlays. It’s been almost a year since Microsoft acquired Minecraft and when Amazon acquired Twitch, and with most technology investors being a bit older than the millennial generation, most of them have enough nostalgia to understand the behavior and recognize the power in the mass audience aggregation when they see events like this one. Like Facebook and Instagram and Snapchat aggregate audience attention on the web and on phones, esports is starting to do the same thing in the same channels, but also in real life, where kids of all ages collide, compete, and make new friends. It’s almost like an entirely new social network, and that’s what gets people excited — and rightfully so.

Quick Takeaways From NYT Story On Amazon Culture

On the morning of August 15, The New York Times published a long, investigative report on the culture at Amazon, one of the country’s (and world’s) largest technology companies. It’s late into Sunday morning the following day, and I’ve just finished the article. It took me so long to read it because I was intrigued by all the chatter and commentary on Twitter in reaction to the piece. Now, having read the original piece, here is what I take away from it:

Women – By far, the most damning part of the piece. The rest of the piece wasn’t that interesting. I can imagine many big, fast-moving companies having lots of drama and dysfunction. It doesn’t excuse unethical behavior, but there are choices parents can make, and oftentimes women (and moms) don’t have much say in the matter. An organization that doesn’t care for those it employs who are so vulnerable at a time around childbirth likely sets itself up for a rude awakening down the road. I can’t imagine a Bay Area company getting away with such ploys in today’s age.

Global Competition – What struck me most about the piece overall is how intense global pressure is on all western countries, America included. American citizens want their iPhones, but they don’t want to read about Foxconn; I want my toothpaste delivered tomorrow, but I don’t want to read about how Amazon makes it happen, right? Think of all the startups rushing to nip at the heels of Amazon. It’s a brutal game and they have big international competition (like Alibaba) and pressure from upstarts (like Wish, and potentially more).

Software vs. Software-enabled – Facebook and Google, for example, have a ton of leverage in their business model. Their software scales in a way that is so elegant, it empowers them to go over-the-top to recruit, hire, and retain employees. These are software-driven companies. By contrast, while Amazon certainly has amazing software, it is more defined by operations, logistics, and a characteristically low-margin threshold to ensures I can get my tube of toothpaste tomorrow. It doesn’t enjoy the elegance of a Facebook web and mobile ad model, and therefore is under all sorts of insane volume pressures the outside world cannot comprehend.

Ad-Homimem Attacks – I’ve noticed an uptick in this behavior, that when information comes out that is controversial and places a tech company or someone in tech in the klieg lights of the press, many (not all) will rush to discredit the source. It happens in politics, too. People don’t like to see stones being thrown at glass houses because in tech, there’s a row of glass houses that make for great fodder for the press who is hungry for more expose-type journalism and want to experiment with new types of media. The reality is that tech is driving the global economy, it is touching peoples’ lives in more and more ways, and the press will increasingly be on the lookout for targets to sink its teeth into. For instance, I can’t imagine Amazon not addressing the women/expectant-moms portion of the article, though I don’t think they’ll care about the rest of it. As I like to say, everyone in tech now plays for the Yankees and should expect scrutiny moving forward.

Power Of The New York Times – I am not sure if this piece, were it published in any other outlet (except The New Yorker) would’ve generated this much of a reaction. There’s something still about the power of the NYT brand, the fear that it will be read across not just the country, but the world; that it will itself drive other outlets and blogs (like this one) to chime in and drive derivative coverage. This piece likely did so well for them, we should expect both the NYT and other outlets to commission and look for stories like this — to examine the bigger targets like Facebook, Google, Apple, Uber, and beyond, and unearth information that wants to come out and will enrapt a mainstream audience.

We live in a new world where some elite corporations have more power than many governments, a world with much less job security, much less influence of those who aren’t fluent in some bit of technology, much more technology that is impacting operations in the real world, much more competition from global conglomerates as well as young upstarts, and many more press outlets who need to figure out a way for a global audience to refer to their work and click on their headlines. I am in favor of the NYT and others writing stories like these. The press is free, and we are all entitled to our opinions on the matters exposed. This weekend’s Amazon piece was likely a test-run for a broader strategy. The world is interested to learn more, and on many things, they have the right to have this and other similar stories aired for everyone to read.

Wrapping Up Another Summer Of StrictlyVC Posts

Well, I wrapped up another summer tour with StrictlyVC, and it was a blast. To quickly recap, there are range of Q&As over the three week, capped off by three columns on my experiences administering and raising small funds.

For interested in venture in China, make sure to read more about DCM’s Jeff Lee and GGV’s Jenny Lee (no relation); for those who want to hear from former Twitter execs who are now VCs, tune into what Homebrew’s Satya Patel and Foundation Capital’s Anamitra Banerjee have to say; the early-stage investors weigh in on today’s environment, including NYC’s Notation Capital (one of the smallest and earliest microVCs); Javelin’s Jed Katz, who isn’t shy about warning of the excesses in seed funding; Susa’s Leo Polovets who talks about why brand is so critical; Kristen Koh Goldstein chimes in about her role in the ecosystem as an investor and founder; and startup personalities Ryan Hoover (of Product Hunt) and Startup L. Jackson (of Twitter fame) take the opportunity to share their views on today’s startup ecosystem.

On Friday’s, I wrote a few posts about recent happenings in the world of venture, first touching on the benefits and costs of LPs who want to invest directly into startups; second, I examine tension between the inefficient costs of a small venture fund versus the importance of being able to invest early into new companies; and finally, I explored the decisions small funds face as they grow, or try to grow, as I am doing now.

It will great to have Connie back as everyone gears up for the fall rush. Thanks again for the opportunity!

When Someone Asks Me About Series A, Now I’ll Just Share This Post

With the explosion of seed investors and seed financings, it’s been fascinating to see the psychology form around “Getting To The Series A.” It’s as if it is a huge marker everyone wants to achieve, and it makes sense. Yet, I’ve found I keep having the same conversation over and over again with seed founders who “think” they’re preparing for A when, in reality, they should be preparing very basic M&A discussions (if they’re lucky).

To that end, I wrote a series of posts about (1) some universal ground rules for preparing for the Series A and (2) exploring alternatives to financing when the Series A doesn’t arrive. The tweets and posts around this led to a vibrant online discussion, which led to a live event organized by Bloomberg BETA last week.

Roy Bahat from BETA took the lead and I moderated the second discussion. We jointly invited Rebecca Lynn from Canvas, Brian O’Malley from Accel, Josh Elman from Greylock, Maha Ibrahim from Canaan, and Hunter Walk from Homebrew. It’s a two-part discussion, each part about 60 minutes. I am not going to have the audio transcribed because I want folks to listen to all 120 minutes of this. No shortcuts on this one. Part of the reason I was glad this came together is because it comes up so much in conversation, I grew tired of explaining it or writing about it. Now, thanks to everyone who participated, I can just share a link to this post and the audio instead!

Seed to Series A: Myths of Raising an A from BLOOMBERG BETA on Vimeo.

Seed to Series A: New Realities of Raising an A from BLOOMBERG BETA on Vimeo.

Put Your Head Down For Five Years, And Then Look Up

Back on August 15, 2011, I emailed my friend Joel with an idea, part out of excitement, part out of frustration. I think about it every August. Last year, I wrote about it here. For me, mid-August is like the beginning of the year, because I can point back to it as when it began for me. In 2014, some things were changing, but most of them were the same. A year later, almost everything has changed. I am in a new place in the Valley. I have much fewer work arrangements, but those now are much deeper. I will be making fewer investments, but will put more wood behind those arrows. I will have less free time, so I will have to be more protective over how I spend my time.

That summer and leading into August 2011 was rock-bottom for me. Now, four years later, nothing is settled yet, but I am in a better place and with each passing day, I gain more clarity over what I want to do next. Maybe it is just one elongated refinement of an idea that will eventually sharpen into one that makes sense and, more importantly, fits — not by being an interlocking part — but by slicing in.

I grew up working in and around restaurants. I had many jobs as a busy boy, dishwasher, line cook. I remember in one of my roles, the sous chef was a great guy but also a hard ass, he drove everyone really hard. One day after work, as we would often all go get a drink, I recall him telling me about when he started out as a cook and how hard it was for him (without formal training) to go from a dishwasher all the way up to sous chef. He worked in very competitive kitchens. He said that he used to have a boss in the kitchen who would tell everyone during their first days on the job: “Put your head down for five years, and then look up to see where you are.”

I haven’t put my head down over the past four years, as I’ve used my blog and online networks to share ideas and learn about industries I have no former experience with, but in figurative terms, I have put my head down, worked at startups, help run deals, helped hire people, helped others raise money, helped others guide to exit, and so on and on. It feels good to just be helpful, if even an ounce helpful, and it’s a great way to bootstrap learning. I’ll likely put my head down more this next year. And, then, I will hit five years, and then, I will really look up and see what is all around me. The magical part of about the Bay Area is that fortunes can change quickly. A lot can happen in a year. And sometimes, there’s only one direction to go.

The On-Demand Conference Expands To New York City

Friends in and around New York City — please mark your calendars for September 15 in downtown in NYC: The On-Demand Conference hits the Big Apple: My co-conspirators in this effort — Pascal from Checkr and the entire crew from Tradecraft (including Misha) — digested feedback from Version 1 and gained the conviction to go for V2.

Back in May, just three months ago, the inaugural “On-Demand Conference” was a hit in San Francisco. That conference concluded with a lively ending where a debate among investors brewed over the issues facing contract workers in the gig economy. [video archive]

Now, just three months later, it’s as if we live in a new world. Some state governments across the country have issues preliminary rulings about worker classification; a parade of well-funded on-demand startups have made headlines by proactively converting some or all of their contractors to W-2′s; presidential candidates running for office in 2016 have brought the topic into debates and headlines; and all of it has come together as a bonafide mainstream news topic.

While things are changing quickly, some of the world’s best venture capitalists have grown wary of the sector. Some have warned that on-demand consumer solutions are saturated, and that not everything needs to be on-demand, and that the high capital intensity in scaling (often without technology moats) all make for a dubious investment climate.

These are are, indeed, valid concerns. Just as the last conference generated substantive debate and featured an entire day of highly-focused content from the startups and operators building these companies, our aim with Act 2 is to double-down on our organizational efforts and create the space where the most pressing issues can be surfaced and debated.

To that end, we have a All-Star East Coast lineup for the event. Click here to see the agenda and browse through the names. We will have managers and GMs from companies like Uber, Instacart, Postmates and many more; we will have some of NYC’s best investor minds on stage; and we will have tech media representing The New York Times, VentureBeat, Scientific American, Forbes, and more.

Finally, and a bit selfishly, I”m excited to share that I will open up the day’s events in a fireside chat with Albert Wenger from Union Square Ventures. For those of you who read Continuations, Albert’s blog, you’ll know he’s written extensively about Uber and ridesharing technologies, about how workers are classified and treated, and his argument to call for Universal Basic Income as a policy in anticipation of a world that may be automated by advancements in technology.

It all has the makings for a fantastic event. I’m looking forward to it. For more information and to register, click here.

The Ingredients For Greatness, By Jerome Bettis

I’m a sucker for speeches. I like to hear people in their own words. Some of the best are Hall of Fame induction speeches. For instance, I remember Michael Jordan’s speech in Springfield, MA (he still had a huge, competitive chip on his shoulder). And, this year for the NFL, like millions of others, I was moved by the words and grace of inductee Junior Seau’s daughter. If you haven’t read her speech, please do — the NFL wouldn’t allow her to accept her father’s induction on stage, so she published it in The New York Times instead.

With a few minutes to spare this evening, I wanted to see what “The Bus” had to say. I always liked Jerome Bettis, but I wasn’t sure what to expect, though I clearly remember he was a dominant and colorful player. His speech (see below) was one of my favorites of all-time, and it only has 366 views on YouTube (at the time I’m writing this). He goes through his entire family, set of coaches from high school, through college, and into the pros, and talks about the fluidity of his life from football, family, and friends, and back again, over and over. (N.B. He called out his mom, specifically thanking her for going to every single one of his professional NFL games — when I looked it up, it’s well over 200 games she showed up, in person. Incredible.)

I wanted to post this because loved the ending of Bettis’ speech. I don’t need to interpret it further, so I listened and scribed down what he said, so you can read it (and if you’d like to listen, it’s at the 32-min mark on the video):

Greatness is not a sports term — it’s a life term. I believe there are four things that get you to greatness. One, you gotta have the ability to sacrifice. A lot of times that means sacrificing the relationships that mean the most to you. The second thing is pain. You’re gonna have to go through some type of pain in your life — either physical or mental — and you’ve got to find a way to endure. The third one is failure. You’ve got to have the ability to understand that you’re going to fail, but it’s how you recover that makes you a better person. And the last, the fourth one, is love, because if you love it, then, it’s not a job — it’s a passion. And if you love it, you’re willing to sacrifice for it, you’re willing to go through all types of pain for it, and you are willing to go through that failure and understand that ‘I will be successful.’ If you go through those four things and understand [them],…then success is in your path. Greatness is available to you.

Haywire is written by Semil Shah, and is published under a Creative Commons BY-NC-SA license. Copyright © 2015 Semil Shah.

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