The Story Behind My Investment In Onfleet

Yes, the company name is Onfleet, not “On fleek,” though they are actually are “On fleek” when it comes to providing platform services and routing infrastructure to the on-demand economy. I could bore you with stats such as powering volume growth at a 30% month by month rate (40% scheduled, 60% on-demand), or how they’re growing B2B revenues by 35% per month, but that’s par for the course these days in SaaS.

The interesting part of the story is how I met Khaled, the CEO, and how I came to invest in the company. @Rafer, for those of you who know, is a friend and tireless supporter of the early-stage companies he fosters. Onfleet is one of those. Back then, in April 2014, the company was called “Trak,” and the founders had recently left Stanford and started their entrepreneurial journey.

At the time, I was writing about the on-demand economy and making a few investments in companies like Instacart and DoorDash. Rafer figured I should meet Khaled, and while I liked him initially as a person (we had a great first conversation), I wasn’t sure I wanted to invest because I didn’t feel a personal connection to the company. My first impression was Khaled was too reserved, but I came to learn letter, I misinterpreted that first meeting. We stayed in touch after I said “no,” and in fact, we discussed this very point. It’s not an easy conversation to have, and who I am to make such judgments.

To his credit, Khaled heard me out and, despite that, asked me very nicely for help in getting the story, pitch, and details together — and so I did, as a friend. He responded really well, and over the next few weeks, we traded a ton of emails, texts, calls. Three months in, Khaled was rolling in his round, and he called me up again — asking me to come on board. Now, looking back, I was lucky I got a second chance to invest, and I took it. Khaled has really grown and matured as a technology and operations CEO, building a team of 10 and providing critical platform services as part of the on-demand stack — right in the middle of one of the biggest trends in consumer behavior we’ve seen.

What Onfleet focuses on and where they’re going, you can read about that in all the news today as they launch into the public sphere. For me, what I’ll remember about this investment is that the frenetic pace of seed often doesn’t afford an investor the chance to get to know someone over a period of time. With Khaled, I had that luxury of time and no pressure other than our mutual respect for each other — and I had a second chance to learn that while he may be reserved in person, he’s relentless in his own quiet way. As I mature as an investor and begin to change my own style, I will look back on how I got to know Khaled over time as a potential model for how I operate as an investor in the future.

Sports Innovation Conference @ Stanford GSB (2015)

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Last week, I was invited to moderate an hourlong conversation at Stanford as part of the business school’s Sports Innovation Conference. You can link through and see all the great panels, speakers, and topics. While I wasn’t able to stay the whole day, what was clear to me from the energy around the event is that entertainment is a huge, huge business and the management of sports talent and rights within that is a major driver of it. Perhaps that’s obvious to some, but the angle to tech and Silicon Valley isn’t often discussed. (I’ve made one investment related to sports, but what attracted me to this company was their unique approach to mobile.)

My panel was titled “The Future of Sports Content,” and we had Karen Brodkin (WME/IMG), Marie Donoghue (ESPN/Disney) and Dan Reed, formerly of the NBA and now Head of Sports Partnerships at Facebook. Let me say up front that while some folks in the Valley “know the business of sports,” these three blew me away with their breadth of knowledge around the intersection of sports, media, and technology. Here are my high-level takeaways from the panel and Q&A:

  • Live vs Virtual: I proposed whether VR could dampen the live-sports experience for spectators, especially those who pay through the nose for nose-bleed seating. We discussed how a few people will ever have a courtside NBA experience in their lives, but now with VR, they could. It’s early days, but everyone — the leagues/teams, the networks, and tech companies — are gearing up for this.
  • Snapchat & FB Mentions vs Instagram/Twitter: An audience member wondered how an athlete/celeb could manage discussions on Facebook (with Mentions) versus being able to easily reply 1:1 on Instagram or Twitter. I’ve got a friend in the NFL who says he only uses Twitter for broadcast but not interaction because, in his opinion, fantasy and trolling has ruined his experience. Instagram works a bit better, but there are still trolls. He hasn’t experimented much with Snapchat yet, but feels like this is where the world is moving for mobile broadcast. (Currently, ESPN produces their daily Snapchat Discover piece, but are looking for ways to create more and automate them over time.)
  • Talent Management in Sports: I did not wholly appreciate all the various rights associated with sports talent and content.
  • A New Sports Category? An audience member inquired about “Participatory Sports” as they relate to current sports networks. Clearly on Facebook, people share and organize around sports, but it was interesting to hear WME and ESPN discuss more recreational sports (like this, maybe?) and how they could become mainstream phenomena in the future — I mean, a while ago, it sounded silly to watch people play video games, right?

StrictlyVC Insider Series (May 13 in SF)

I’m excited for the StrictlyVC events that are rolling out this year. I’m proud to now be a member of StrictlyVC’s Advisory Board, and the next “Insider Series” event is just around the corner on May 13 in San Francisco. There are a few tickets left, so you can click here to register and get a ticket for the event: http://strictlyvcsinsiderseries.splashthat.com/

The agenda looks awesome for those of you who are venture-nerds like me. Connie Loizos (@cookie on Twitter) has done an incredible job to draw in great speakers who will be in conversation with the group, investors from Sequoia, Lightspeed, and Pantera — and Parker Conrad, the CEO of high-growth startup Zenefits. Specifically, Bryan Schreier from Sequoia will chat with Marco Zappocosta (co-founder of Thumbtack); Connie will have a chat with Lightspeed’s Jeremy Liew (who invested in Snapchat, Whisper, and a bunch of other cool companies; I will sit down with Dan Morehead from Pantera Capital to talk about the current state of Bitcoin, and Connie will end the content session with Parker from Zenefits.

All of that, plus some good beers and conversation before the show starts and after the show ends. I made great new friends at the previous event and ran into a bunch of old friends. For me, even though the content is great, that’s the best part — meeting other folks interested in investing. Get tickets while they’re still available.

A New Conference: The On-Demand Economy (May 19 in SF)

A year ago, I wasn’t sure if the “On-Demand Economy” (ODE) was the real thing or just a fad. I’d keep asking myself, “How can this persist?” and plenty of other people would ask me the same thing, given that out of 70 or so investments I’ve made, over 20 of them touch the on-demand stack in some way. Now as 2015 approaches the midway point, I have since gained more confidence this isn’t a fad, but the early stages of an on-demand world where we will summon goods and services via our watches, via single-purpose connected devices, and perhaps even without consciously thinking about it. Geographically, ODE services are tailor-made for the developing world and urban centers in Asia, especially as those consumers and labor suppliers go straight to mobile devices and skip the laptop and web generations entirely.

So, it was even more good fortune when one of my most frequent seed-stage coinvestors in ODE, Pascal, pinged me on IM to say he’s putting together a conference with my friend Misha @ Tradecraft. I jumped in and we are going to co-host this event on May 19 in San Francisco. Pascal had a good base committed, and so I called up Bastian, Max and Apoorva, Tony, Tri, Dan, Nick to participate — they all loved the idea, as did all the great tech writers who have cover the trend, like Ryan, Eric, Katie, Leena, and even Liz after her breakout series on the topic from 2014. I called up other friends who have also made core investments in ODE, and we are happy to have Satya, Steve, and Simon round out the event. As a bonus, I called up Shervin and convinced him to do a 1:1 Fireside Chat with me earlier in the day.

If you are a potential founder in ODE, work in the sector, want to learn more, cover the sector as a journalist, or invest in it, this is a can’t-miss conference. Here are more details:

Date: May 19, 2015 (all day)
Location: Broadway Studios, North Beach, SF (map)
Website: (link)
Tickets: (register)

Existential Risk In The Seed Stage

I just sent this out to Haystack companies which are at the seed stage. I tend to look at things through the lens of existential risk at this stage, which then inform the milestones (not all metrics-based) to reach as a guidepost. I wanted to share it with you all as its generic, but shows how I’m thinking about things today in mid-2015.

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My Job
I view my job as a small investor with a small fund is to identify and help great founders & companies. If I had to boil down where I help most, it’s around getting ready for a proper seed or Series A round, depending on stage. I am here to help and plan out these things with you way ahead of time, so please consider me as a resource.

(For those of you who’ve already raised rounds with lead investors, please disregard — they will now focus on this for you, hopefully.)

However…I have noticed I’ve fallen out of communication with many of you at the seed stage, email is hard, folks are heads down building, etc. To me, one of the Top 3 functions as CEO is to make sure there’s enough money in the bank. In this scenario, it means the next round, and investment rounds usually come together because of (a) breakout growth or more likely (b) reaching fundamental PM fit, key metrics, and other foundational milestones. In my experience, this stuff takes many months to set up and get right, and it takes many months to develop a relationship with the next lead investor.

These are all places where I can help, and I’m writing to offer this to you all again. Ultimately, it won’t work for everyone, and that is OK, but please do keep in mind that if you’re in a position where your cash balance is going down and things need to happen faster, it’s usually hard for me to come up with a palatable solution in a short period of time.

Other Notes
We are in a frothy seed market. It is good to be a founder during a seed round, but the number of institutional Series A deals are about the same. That means, the bar is higher for everyone, and everyone (you and me) should be constantly concerned about future financing risk — even moreso given how easy it is to raise seed. The drop off is severe.

The Month Of May
I will be gone for a lot of May. I have two work trips and taking a family trip. I will be on email, but slow to respond around Memorial Day. Text/FB message me for emergencies during the month, please. I’ll do my best to get back to you quickly.

Talking VC With Kate Kendall And CloudPeeps At Women 2.0

Last week, Kate Kendall of CloudPeeps invited me to speak with her at Galvanize in SF for a Women 2.0 event. I met Kate about a year ago and was happy to become a small investor in CloudPeeps about six months ago. She wanted to have a discussion with the Women 2.0 crowd about her experience as a female founder and CEO, about how she met and interacted with me, and to field questions from the crowd — which looked to be about 100+ people.

The talk went by really fast. Kate talked about how she raised her seed round (just under $1m) and all the tactics she used. It was fun for me because I didn’t see those, but she is a crafty one! We also broke down how I was intro’d to her, how we communicated while she was in NYC (heavy email). and how she finagled an invite to an event I was speaking at, engaged me in conversation, and a few weeks later — I became an investor in CloudPeeps. (The rest of the Women 2.0 talk was very fast, and most of the questions and answers were pretty generic, so I’ll keep this post brief.)

What occurred to me only in retrospect is that after two years of investing at the angel/seed level, Kate was the 1st female founder I’ve invested in via Haystack. Since then there are two more companies with females on the founding team. In my chat with Kate last week, the topic of “how was it different with Kate being a woman?” never came up in discussion. Reflecting back, it never really did come up in my chats, phone calls, and emails with her. In fact, I never thought about it. And, that’s the hard part to convey — the overwhelming majority of investors I know, even those who invest very, very early, wouldn’t discriminate against a woman as founder or CEO. In fact, I have seen many female startup CEOs be at the center of very competitive financing rounds, fielding multiple offers, and in total control of the situation. One company I’ve been dying to invest in for over eight months has a female CEO, and she has told me “no” at least 10 times.

In my chat with Kate, I did mention to the crowd that the life of an investor comes with saying “no” all the time, all day long. I think about my time and attention so much, I often say “no” to social events or running errands during the holidays with family. So, ultimately, investors are going to say “no” to all sorts of people, regardless of color or race or gender. The position calls for discrimination in the sense that most opportunities are passed on, even if they’re qualified or even exemplary as companies and teams. I myself have made a big $100M-run rate mistake as an investment I passed on for a silly reason. This isn’t to say that things couldn’t be improved or that there are unsavory stories and experiences people experience in the game to get investment, but two years in, for at least what I’ve observed, both first- and second-hand, the overwhelming majority of investors I see are busy chasing anything that’s growing or has evidence of promise and with disregard to “who” is helping make that growth or promise happen.

That Was Easy: Amazon Dash Button In An On-Demand World

The On-Demand Stack gets even more interesting every week. The latest installment, courtesy of Amazon, involves little WiFi-connected dongles with buttons for Amazon customers to summon — with the ease of a finger push — more of the item which corresponds with each dongle. Running low on toilet paper? Just tap the Charmin button provided by Amazon (while your phone is nearby) and Amazon will take care of the rest.

Amazon and Google are competitive along the fault lines of search and intent. Both live on input/output. This creative innovation around input from Amazon makes it theoretically easier to order more toilet paper vs pulling out your phone, finding the Amazon app, then inputting the search term, putting the item in your cart, and you may continue shopping, maybe — and then you have to check out. That said, setting up these dongles won’t be a piece of cake for the average user, either. I’m of the belief that even setting up basic bluetooth devices to the phone will be hard for people, but I believe Amazon will make it easier. And, they can distribute anything.

So, if this works, this is a huge leap forward for input — what about output, i.e. how soon you need the toilet paper? That’s where things have been harder for Amazon.

Back in 2013, I wrote a post titled, “From Amazon Prime To Amazon Pronto, The Future Of Physical Delivery.” Amazon figured out how to get us anything in that 48 hour window. Now, for the past few years, with the combination of mobile devices and a shift in the labor economy, new companies have emerged with new models to add gusto to the “pronto.” Some services are set up to deliver you things on demand, such as Uber and Postmates and Sprig — some things are set up to deliver things in a more scheduled manner, like Instacart, DoorDash, Boxed, and Luxe. Amazon has been trying to chip away at better delivery on the same day — they’ve dabbled in groceries for years, they just announced home assembly services for big orders, and they clearly want to deliver more things faster to our homes and offices.

The output function here is trickier for Amazon to execute on within this 48 hour window. Additionally, my observation of how confusing Prime Pantry is for the average user (as many of those household items are costly to ship, so they devised a confusing tax around them) could make Dash a hit because people may not order things at the point of depletion, but rather when the supply is about to be depleted.

Ultimately, the craftiness with this move around Dash Button is something I’d frankly expect from a startup — in this case, it’s Amazon, the somewhat lumbering incumbent, fresh off the heals of that Fire Phone debacle and stock massacre. It is a terrific concept, assuming consumers can wire them up and they work. Let’s see how consumers behave as these rollout. App installs for these nonviral apps is hard and costly, and Amazon can just shove these into corresponding boxes or send them to us based on our order histories.

The other angle is that Dash Button is likely built to be a broader platform, extending from the regular household inventory systems into specific verticals — think basic stores, or small businesses, or to order dinner, or groceries. It all comes down to SKUs. Every button — like every app — can empower the customer to access a SKU from a variety of sources, and Amazon (or a startup eventually) can help get it to the destination fast. End of the day, I’m impressed. Assuming Dash Button is spread to customers properly and they can onboard, it could be 1,000x easier to order versus a mobile app, no question. So if you’re scoring at home: Output is still a knife fight between Amazon, Google, Uber, and a bunch of startups; but on Input, Amazon’s ingenuity scores very, very high, reminding me of the classic Staples ad campaign with the “Easy” button (pictured above).

The Story Behind My Investment In HourlyNerd

Toward the end of college, and again toward the end of graduate school, there was a predictable recruiting campaign from all sorts of consulting agencies looking to scoop up and hire labor. In exchange for brand, a high salary, and a bit of prestige, graduates would sign up early in the final year, start a plan to payoff their student debt, and sign-up for intellectually challenging work filtered down through various organizational levels.

I know all of this because I almost lived it. Worse, I wanted to live it. As I saw it all go before my eyes, I also jumped into the fray, practiced case questions, riding off the competitive juices of the process of staged interviews. That process exposed me to the partnership model of consulting shops. The hierarchy could be loosely described as “finders, minders, and grinders.” New graduates were “grinders,” grinding out the work with long hours; “finders” were the partners, who found new clients and managed existing ones; and “minders” sat in between the two, minding up and minding up.

Now, what if online networks could put the clients directly in touch with labor? Could that create more efficient flow of information, better working conditions, and better output?

I think so. A few years ago, I used HourlyNerd for a few projects and was surprised by the output. They used a vetted network of current and recent grad MBA students, matched by background and interest, to create slide decks, conduct research, and so forth. So long as I (the client) was able to scope out what I needed, the workers (students here) were more than capable of producing the work with the added benefit that we never had to meet, we were able to email and chat online, and they could keep their hours and location flexible.

Then, out of the blue, the founders pinged me about their latest round. This is a bit later stage from when I invest, but I asked the founders a ton of questions about their plans to scale, about how their marketplace could propel them beyond a services network. Even though my check was small for them at stage, they made a concerted effort to engage with me around all of my nitpicking questions. Through that process, I learned some interesting facts: Over a yearlong period, the company had nearly tripled its average project size, that most customers repeat purchases frequently, that the marketplace had very good liquidity, and an average sale price that would make an investor pretty happy.

So, I am breaking my own model for Haystack and investing “late” into HourlyNerd, partly because they’re empowering the folks who, like me, could’ve also taken that traditional path into consulting. With a company like this, now those workers are free to interact directly with clients, to build their own reputations around topics, to travel and live where they want to, and much more. It’s a mission I can support — not only with an investment, but also my time. Sign up here and give it a try, they offer a great discount to start.

The Story Behind My Investment In Gyroscope

Gyroscope

In the middle of 2014, one of my friends on Twitter (@Stammy) kept retweeting an account into my feed, usually with a screenshot. Turns out, it was his friend and roommate, and that friend and roommate had created software which just looked different than other products.

I conducted a bit of Internet sleuthing and discovered my friend’s roommate used to work for a company I was dying to invest in earlier but couldn’t convince them. That company creates great web and mobile products, too, so my interest piqued. I asked my friend for an intro, and after a few months, it came through. I rushed to meet the entrepreneur a few days later.

Turns out, my timing was good.

Anand had built the v1 of Gyroscope, currently web-based software which served as a hub for all of a person’s connected device and monitoring/tracking data. By connecting various accounts to your Gyroscope, the products gives you a kaleidoscopic view of where you’ve been, the pictures from those places, how many steps or calories you’ve collected and more. But more than just aggregating data, there’s something about the product, the design and animation, which makes it compelling.

I wasn’t sure where Anand was in his thinking. I wasn’t sure if he wanted to join a company, or still travel. We talked broadly about his options and I didn’t share any of my own views on what he should do, except that if he thought about it and wanted to start a company, I would be his first check and help him close the round.

A few days passed and he got back in touch. He was ready to start. I didn’t expect that, but was psyched about it, no doubt. We put our minds together, came up with a plan, started engaging lawyers, and all those details — we priced the round, I wired my funds, and started making introductions for Anand. We also opened up a small AngelList Syndicate, which has been closed for a while. At the end of it all, a larger fund also came in to give Anand and Eric a good solid cushion to build out v2 of the product.

As 2015 unfolds, the landscape has changed. Apple has committed some of its attention with Apple Watch to digital tracking, fitness, and health sensors. We are accumulating more connected devices which collect more and more data about us or our surroundings. What will do with all of it? Who owns that data? These are big questions, and while I don’t know the answers, I have a good feeling Gyroscope will be in that conversation.

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