Archive

The Side-Hustle Into Venture

Last weekend, a number of people shared the first-person account of millennial “side-hustling” that was published in Quartz. You can read the article here. It’s not that great of a piece, nothing new or earth-shattering is revealed, but I’d wager it was shared so widely because people have […]

The Story Behind My Investment In Tempo Automation

About a year ago, my friend in NYC Joel pinged me about a company he had invested in. It was a short description, but I took the intro and met Jeff, the CEO of Tempo Automation, for coffee. We had a great discussion, and he had the right […]

Reflections On The Startup Funding Climate As We Slip Into Summertime

Disclaimers: This isn’t a doom and gloom speech. There’s tons of opportunity out there. And, this is mainly focused on consumer markets. Also, this post is a little long in the tooth. Please forgive me. I haven’t had time to write with all the little kids running around […]

Unpacking Microsoft’s Acquisition Of LinkedIn

The first notification which caught my bleary eyes Monday morning — Microsoft to acquire LinkedIn for $26 billion. Much has been written about why this may make sense for Microsoft. What’s less clear is: What motivated LinkedIn to take this path? I’ll attempt to answer this at the […]

Dissecting This Week’s Media Fissure

(Disclaimer: Before a writer rips me apart or tweets this post without reading it fully, I used to be a long-time columnist for TechCrunch (the most frequent contributor they’ve ever had, over 100 posts and nearly 100 videos over a three period. I’m also a small, early-stage investor […]

In Fundraising, As In Politics, “It’s The People, Stupid!”

People will sometimes stop and ask me, “How did you become an investor?” To which I usually reply, “I’m not a real investor — I just play one online.” It’s partly a joke, but there’s some truth to it — it’s easy to write a few small checks […]

What The Money Folks Are Saying

There’s a lot of noise about what’s happening the private startup market. It’s easy to just say X and Y are happening and read the headlines. Today, I got an email from Industry Ventures (IV), which acts as an LP into various VC funds and invests in “special […]

When Inbound And Outbound Get Turned Upside Down

In the world between founders and investors, both sides should always be mindful of their interpersonal behaviors — especially being aware if the origin of each relationship is outbound, inbound, or mutually developed. In a situation where one experiences inbound interest, that person is often at an advantage […]

Medium Rare

I love Medium, the product. I wish I had the opportunity to invest. When Greylock became their first institutional investor, I knew Medium would be a billion dollar exit and wrote about it here. Since then, other great investors and firms have backed up their trucks to ride […]

Shift To Consumer Investing

I intend to shift most (not all) of my focus back over to consumer investing in Haystack 3. In my first fund, it was dominated by consumer. That wasn’t intentional. I was just starting out, I was a dog chasing cars. In my second fund, most of it […]

The Chocolate Chip Cookie Company

Nearly a decade ago, I met an investor while I was in Boston who was trying to explain to me how some very rich people like to invest. This is many years before I become interested in investing myself. He called it “The Chocolate Chip Cookie Company” syndrome. […]

Minimum Wage, Maximum Automation

The State of California recently unveiled a plan to increase minimum wage in the state to $15/hour by 2023. Currently, America’s national minimum wage is $7.25/hour, which hasn’t increased since 2009. The concept of minimum wage is complicated, and I don’t want this post to be focused what […]

Investors Are Going Botsh*t Crazy

Bots. They are everywhere in startup land. It feels like a gold rush — a bot rush. And, there is a backlash, as well — a botlash. Whether it’s more and more people using Slack and other messaging apps and come across these new bots and features, the […]

Human Memory, Connected Storage, and Digital Nostalgia

I caught up on Lefsetz’s blogs from the past two weeks yesterday. A few stuck out, like always. In particular, he wrote something about his history of Springsteen concerts, which you can read here. His recounting touches on all sorts of nostalgia triggered by following The Boss over […]

Picking, Riding, And Investing In The Next Great Technology Wave

The last big wave which helped generate huge returns for technology investors was largely driven by phones. Building apps and services on top of phone sensors, connected to the network, gave us new media apps like Instagram and Snapchat, new communication tools like Whatsapp and Messenger, and new […]

Early-Stage Investing: Notes From The Field, Mid-March 2016

Where is the early-stage financing market for startups today, mid-March 2016? In my opinion, and depending on where specifically you sit, right back where it left off. After a few bumps over the last 9 months, with little shocks in July 2015, a bigger shock in August 2015, […]

Black Swan Politics

This post is not about taking a side on a political issue or for a particular candidate, or drawing a line between what’s right or wrong. Before this could be twisted by others, let me say I do not condone the messages being used in the campaigns in question […]

Thank You, Surge, May I Have Another?

Late last night, around 10:30pm (“late” for parents), my brother (who is visiting from the NYC area) and I were standing in my kitchen as he was getting an UberX to head back to the city. There’s never really surge at that time. He started with 1.7x. Waited […]

Quickly Dissecting GM’s Acquisition Of Cruise Automation

I haven’t written here in a while (for my usual pace). Lots going on. So, I need to get back into it. The world isn’t quite right when I’m not able to collect and organize my thoughts here. And, luckily, I woke up before everyone today and, from […]

Twitter: While You Were Away, Episode 3

Third installment of our new podcast, “While You Were Away,” a sort of Rap Genius for tech Twitter conversations. Joel Andren (who hosts this podcast) does a terrific job stalking Twitter to see conversations unfold and learning from them. 1/ Startup in SF – Worth It?, relating early […]

Twitter: While You Were Away, Episode 2

Second installment of the new podcast, “While You Were Away,” a sort of Rap Genius for tech Twitter conversations. Joel Andren (who hosts this podcast) does a terrific job stalking Twitter to see conversations unfold and learning from them. 1/ Startups vs Regulation, relating to changes at Zenefits. […]

The Story Behind My Investments In Booster Fuels and AquaCloud

Oil and water do not mix. When one attempts to mix them, they separate. Despite the laws of basic chemistry, it turns out oil and water do, in fact, mix in the Haystack portfolio. Oil and water have been in the news lately. Regarding oil, where the price […]

New Podcast: “Twitter: While You Were Away”

For years, I’ve been wanting to do a simple podcast. However, while I always used to organize them, I didn’t want to do that this time around. I planted a few seeds with friends but nothing clicked. Then, my friend Joel Andren tweeted he wanted to start one, […]

Investing Notes From The Upfront Summit (2016)

At the start of 2015, I was lucky to head down to LA for The Upfront Summit. It was a blast, so I was excited for this year’s event, and 2016 was even better. I just got back to The Valley last night after two days in Hollywood, […]

Challenges And Opportunities For Seed Funds (2016 version)

A while back, I wrote a post here on the “5 Challenges Facing The MicroVC Model.” Since then, I’ve added more and more, and now we’re up to nine. Some LPs I talk to frequently have joked “if there are so many challenges, why do it?” It’s a […]

Navigating The Gap Between Seed And Series A (2016 Version)

I try to help anyone coming through the network gear up for financings. Lately, the famous “gap” between seed and larger VCs for Series A has been exposed again. This “gap” has been written about ad nauseam, so I won’t do that here. Instead, let’s discuss how a […]

Investment Criteria, Focus, and Process For Haystack Fund 3

Investment Criteria For Haystack #3 For my third fund, Haystack III, which is still a small fund (but larger relative to my previous funds), I wanted to share a simple and straightforward guidepost for founders, seed syndicate partners, angels, and larger VC firms as to what I’m looking […]

Quick Reaction To PG’s Essay, “Refragmentation”

As Paul Graham usually does with his essays, he makes a deep point with relative ease. Today’s essay, which many of you have read (and if you haven’t, please read it here) is even more intense. I had a sense he would be writing about the relationship between […]

Quick Follow-Up On Facebook, FreeBasics, And India

A few days ago, I wrote an opinion post on my blog, based on my point of view on what I’ve read and my experiences working in India, about the debate going on India currently between’s Facebook’s desire to push FreeBasics and the impassioned response (among many of […]

Looking Ahead To 2016

Earlier this week, I tried to boil down the top trends that defined the startup and investing landscape for 2015. Next up, I want to think about what will shape our experiences in 2016. This isn’t going to be a post about pontificated predictions like “Digital Healthcare is […]

Facebook Meets The License Raj Of India

It’s easy to think of Facebook as the world’s largest social network. It takes a bit more imagination to envision Facebook as the world’s dominant global nation-state, a new type state where citizens can connect and communicate across political borders and where the network’s CEO, who is only […]

The Force Awakened In 2015 Startup Tech

Star Wars is all the rage now, as it should be. As I was reflecting on 2015, indeed, the Force (of the market) awakened. Turns out there are a lot of problems in the world to solve and lots of money to fuel those experiments, but there aren’t […]

Investment Lessons From Howard Lindzon

I love reading Howard Lindzon’s blog. I subscribe to the raw RSS feed to bring the text right to my email, so I never miss a post. It is almost always straight and the point, with Howard’s biases shining through. Truth be told, I ignore about half of […]

Investing In Mobile 2016

As someone who worked in mobile, wrote about it all the time, lived and breathed iOS platform, and discussed widely my reservations for investing in the space, I’ve been thinking again lately how I’ll invest in mobile in 2016 — or even at all. I’m a broken record […]

Blocking On Twitter

Lately on Twitter, there have been some interesting threads (and posts written about those threads) on the topic of blocking people on Twitter. It’s a timeless debate with no morally correct answer. Some believe any user has the right to block others, while others believe Twitter is about […]

The Cost Of Lengthy Fundraising Processes

Disclaimer: I myself have made countless “process” mistakes, have gotten worse at replying to all emails, and sometimes take longer to close loops. I also don’t intend this post to sound like it’s an easy fix and everyone should do it. I’m sure most want to, but it […]

Jamie Foxx Interview by Tim Ferriss

This is a very long podcast, but I loved it, so more than just link to it on Twitter, I wanted to post it here and give a bit more color on it and why I’d recommend it. It’s over two hours long, as a disclaimer. I listened […]

The Tension Between Governance and Deal Flow

One subtle facet of venture I’ve observed lately is the inherent tension between corporate governance of a startup by an investor and that investor’s deal flow. LPs, the entities which invest in VC funds, obviously want their GPs to have meaningful ownership in the companies they invest in, […]

Spray and Pray (and Pounce)

“Nobody panics when things go according to plan, even if the plan is horrifying…Introduce a little anarchy, you upset the established order and everything becomes chaos.” – The Joker, The Dark Knight Entrepreneurs are the souls who see and build the future. The investors who invest in those […]

Computer Sapiens

In anticipation of the ethical challenges that would present themselves as a result of advancements in medicine, biology, and technology, the field of bioethics was born, an interdisciplinary field of study whose aim is to provide frameworks for making decisions in a world defined by increasingly advanced, complex […]

Post-Seed Fireside Chats 2015

At the end of year, the investors from Bullpen Capital, Venture51, Vator, and yours truly get together to host the “Post-Seed Conference.” This year, its second year, proved to be a terrific event, and the main themes were so central to what’s happening in tech/investing in the Valley, […]

The Full Ratchet Interview: The Path To Series A

Earlier this year, I started tweeting and writing more about seed startups getting on a path to Series A funding. That topic kind of took a life of its own, even considering options for companies when the Series A doesn’t arrive. A few of us even got together […]

The Story Behind My Investment In Figma

Back in 2012, my friend Pete (who was working at LinkedIn at the time) mentioned one of his former interns was a superstar. “I’d love to meet him,” I said. At this time, I didn’t yet have a fund. A few weeks later, we met for coffee, and […]

The Makings Of A Third Haystack Fund

When I started my first fund, a long-time VC I respect asked me a question which still remains unanswered: “What’s your view of the world?” Damnit. That question really stumped me. Still does. Partly, I wanted to have a good answer to respond to this person’s question. Mostly, […]

The Post-Seed Conference, The Sequel

A year ago, the folks at Vator, Venture51, and Bullpen kicked off the inaugural “Post-Seed Conference” in San Francisco. The event was a hit. You can read about the 2014 version here. Over the last year, we’ve seen a few big, public market corrections; we’ve seen increased tech […]

Climate Change And Antifragile Investing In The American Retail Sector

A few years ago, Albert Wenger wrote about the concept of “Antifragile Investing,” based on the book “Antifragile” by Nassim Taleb. Wenger, who has occasionally written about the forthcoming dangers from climate change, suggested that as trends form (like a storm), it presents both chaos and also an […]

The Super Pro-Rata Signal

Here’s something I believe will become more prevalent as angel and seed funds which lead deals scale up and try to help their portfolio go to the next level: The increasing importance of a signal created by an existing investor who wants and/or takes a “super pro-rata” position in […]

Stopping At The Drive-Thru On The Road To An Uber IPO

After thinking about writing a book and then ditching that idea in favor of a much simpler and more rewarding weekly newsletter (signup here), I have used so many different sources and tools to keep track of all the news worldwide about Uber. Like Apple is a boon […]

AngelList and Y Combinator Continue To Shake The Trees

They say that “bad things come in threes.” For those working in and/or observing the world of venture capital, this week provided some good fireworks, with two early stage powerhouses announcing power moves. It also happened to coincide with a week where investors in the Bay Area congregated […]

Reflecting On The First 100 Investments

As I begin Haystack III, I wanted to write down and share the reflections I’ve had on seed investing to date. However, please note (1) I’m still learning; (2) I’ll make new mistakes; and (3) these reflections are for me, and not generally applicable to others — there […]

Haystack is written by Semil Shah, and is published under a Creative Commons BY-NC-SA license. Copyright © 2017 Semil Shah.

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