Metastasized Assumptions

When folks ask “Hey, how’s it going?” I usually respond with “Can’t complain” or “Optimistically paranoid!” It is really how I feel. First off, how lucky are all of us — founders, investors, limited partners, journalists, early employees — to work in such a dynamic ecosystem. Second, paranoia feels like a necessary ingredient for not taking the former all for granted, yet we all (or, most of us) are hopelessly optimistic — we believe we will reach our next milestones. And, why not? The industry is made of so many folks who are in the business of betting on themselves over the next guy or gal. And, we all have plans. Many plans. And, in those plans, we make assumptions. Many assumptions. And, the more we repeat them, they begin to take a life of their own. And, in those repetitions, we start to Continue reading "Metastasized Assumptions"

Investing Notes From The Upfront Summit (2018)

It is probably my favorite “big” tech conference of the year. Every year, in late January, hundreds of VCs and LPs make the trek to Los Angeles for The Upfront Summit, hosted by the team at Upfront and their local sponsors. If Twitter is the best mechanism for measuring the pulse of the VC ecosystem online, then The Upfront Summit is the best mechanism for doing so in real life. Looking back on my notes from 2016 and 2017, it is clear the show for 2018 was notably different.

And with that framing, here are my quick notes from this year’s event. From my vantage point, both consuming the content on stage but also from the chattering outside in the hallways (and on the production lots at Warner Brothers), The Upfront Summit 2018 was marked by three “C’s”:

1/ Culture – Usually the first day of the event Continue reading "Investing Notes From The Upfront Summit (2018)"

The Story Behind My Investment In Wag

Back in early 2015, while I was a venture partner with Bullpen, the guys there remarked about one of their portfolio founders on a continuous pivot with his company and that while it seemed crazy, they admired the team’s craftiness in hunting for the next thing. Ultimately, that company ended, and the founders wanted to start a new company right after — Wag!. There wasn’t much time to reflect in between. There was no Medium post about the shutdown. The new idea wasn’t remotely related to the previous ideas. Bullpen was going to back the founders again, and I agreed to take the meeting after getting a few pings from my friend Jonathon at Ludlow.

I’m glad I did. In the meeting, Josh and I talked about how they started a dog walking service via mobile app. After investing in Instacart, DoorDash, and Managed By Q, I had studied

😉
Continue reading "The Story Behind My Investment In Wag"

The Story Behind My Investment In New Knowledge

If you can remember back nearly two years ago, the tech startup chatter was consumed by a fascination with bots. This was during a time when Facebook Messenger experimented with bots for brands, and when the ecosystem went a little overboard in its hopes for automation. Little did we know back then there was a very ripe use case for bots — but it wasn’t in the way we hoped it would be. From the days of Friendster and MySpace all the way to the 2016 American election, the penetration of social networks and social media were lauded as a welcomed frontier in how society shared and digested information.

Fast-forward to 2018, and the debate around the publishing power social networks — mainly Facebook and Twitter — have over the flow of information is at a fever pitch. Both the stakes and corresponding tension are high. Just this week, Twitter Continue reading "The Story Behind My Investment In New Knowledge"

The 2018 Seed Stage Reset

This post is about the Bay Area startup and venture ecosystem. I believe the local ecosystem just completed an entire “reset” with respect to the earliest stages of company formation. (I need to state upfront that this isn’t about the seed landscape nationwide — I’ll address that in a different post this year.)

When I began investing nearly five years ago in 2013, there were clear delineations between investment rounds — a founding team would raise from friends and family (and eventually, through scouts and Syndicates), progress to seed funds (established ones institutionalizing while new ones sprouted up), and then reach the promised land of the institutional Series A round, typically led by an established VC firm with a history of joining boards, maintaining ownership, and needing to drive large outcomes over many years to make their fund vehicles profitable. There was little cross-stage investing and many folks became Continue reading "The 2018 Seed Stage Reset"

The 2018 Seed Stage Reset

This post is about the Bay Area startup and venture ecosystem. I believe the local ecosystem just completed an entire “reset” with respect to the earliest stages of company formation. (I need to state upfront that this isn’t about the seed landscape nationwide — I’ll address that in a different post this year.)

When I began investing nearly five years ago in 2013, there were clear delineations between investment rounds — a founding team would raise from friends and family (and eventually, through scouts and Syndicates), progress to seed funds (established ones institutionalizing while new ones sprouted up), and then reach the promised land of the institutional Series A round, typically led by an established VC firm with a history of joining boards, maintaining ownership, and needing to drive large outcomes over many years to make their fund vehicles profitable. There was little cross-stage investing and many folks became Continue reading "The 2018 Seed Stage Reset"

Quickly Unpacking The Uber “Softbank IPO” Exit

Whenever there’s a big startup exit, I try to quickly unpack it here on the blog. There’s been so much news about Uber for the past year and more that, frankly, I have tuned most of it out. It’s almost laughable now three years ago, I actually thought about writing a book on this company and sector. Ultimately, I started a weekly newsletter around it and still couldn’t keep up on all the news forming around this company.

With that backdrop as context, it almost slipped my mind that the tech startup world and the SF Bay Area, in particular, experienced a huge “exit” with the Uber-Softbank deal. I write “exit” in quotes, however, because it is not the type we are used to waiting for or dissecting or even the type we get to see up close. As Fred Wilson noted this morning, USV and other firms can Continue reading "Quickly Unpacking The Uber “Softbank IPO” Exit"

Quickly Unpacking The Uber “Softbank IPO” Exit

Whenever there’s a big startup exit, I try to quickly unpack it here on the blog. There’s been so much news about Uber for the past year and more that, frankly, I have tuned most of it out. It’s almost laughable now three years ago, I actually thought about writing a book on this company and sector. Ultimately, I started a weekly newsletter around it and still couldn’t keep up on all the news forming around this company.

With that backdrop as context, it almost slipped my mind that the tech startup world and the SF Bay Area, in particular, experienced a huge “exit” with the Uber-Softbank deal. I write “exit” in quotes, however, because it is not the type we are used to waiting for or dissecting or even the type we get to see up close. As Fred Wilson noted this morning, USV and other firms can Continue reading "Quickly Unpacking The Uber “Softbank IPO” Exit"

Looking Ahead, Predictions For 2018

Turning the page on 2017, here’s what I’m looking ahead to in 2018:

I want to keep this post brief as possible. Below is a set of predictions for 2018 in tech startups and VC. This is also a window into the principles and beliefs I hold and which, in turn, form my behavior and actions in the ecosystem. So, some of this is tipping my hand, but I would welcome being challenged on any and all of these claims ;-)

Before I begin, a brief review of my four 2017 predictions, located in full here. For the first three, I give myself a C, F, and F, mainly because they’re boring and too broad. However, for the last one, #4, man… I hit that out of the park: “Digital currencies will be offered as part of a sophisticated investor’s portfolio.”. A+ and if I only acted more on Continue reading "Looking Ahead, Predictions For 2018"

Looking Ahead, Predictions For 2018

Turning the page on 2017, here’s what I’m looking ahead to in 2018:

I want to keep this post brief as possible. Below is a set of predictions for 2018 in tech startups and VC. This is also a window into the principles and beliefs I hold and which, in turn, form my behavior and actions in the ecosystem. So, some of this is tipping my hand, but I would welcome being challenged on any and all of these claims 😉

Before I begin, a brief review of my four 2017 predictions, located in full here. For the first three, I give myself a C, F, and F, mainly because they’re boring and too broad. However, for the last one, #4, man… I hit that out of the park: “Digital currencies will be offered as part of a sophisticated investor’s portfolio.”. A+ and if I only acted more on that Continue reading "Looking Ahead, Predictions For 2018"

An Imperfect Glance At Tech’s Notable Exits In 2017

This will be a brief post looking back at some of the notable tech exits of 2017. Before we begin, there are many disclaimers that must be made…

First, this is not complete and perfectly accurate data; this data is difficult to obtain, so we did our best with publicly available sources to find the most notable exits (read: not every single exit). Second, this data will not reflect a potentially decent number of acquisitions that are below $100M in sale price, as in many of those cases, the acquiring company (if public itself) isn’t required to publicly disclose such transactions. Third, without seeing the actual cap tables at time of sale, it’s difficult to know the specific ownership holdings for investors. Fourth, for the year’s tech IPOs, we looked at the work published by CNBC’s Ari Levy; as such, it is difficult to know Continue reading "An Imperfect Glance At Tech’s Notable Exits In 2017"

An Imperfect Glance At Tech’s Notable Exits In 2017

This will be a brief post looking back at some of the notable tech exits of 2017. Before we begin, there are many disclaimers that must be made… [note: if we missed a “notable” exit, please let me know & I’ll update the sheet…]

First, this is not complete and perfectly accurate data; this data is difficult to obtain, so we did our best with publicly available sources to find the most notable exits (read: not every single exit). Second, this data will not reflect a potentially decent number of acquisitions that are below $100M in sale price, as in many of those cases, the acquiring company (if public itself) isn’t required to publicly disclose such transactions. Third, without seeing the actual cap tables at time of sale, it’s difficult to know the specific ownership holdings for investors. Fourth, for the year’s tech IPOs, Continue reading "An Imperfect Glance At Tech’s Notable Exits In 2017"

Brief FAQ From Haystack IV Fundraising Experience

Earlier this year, I wrote a post detailing how I was able to transform Haystack into an institutional fund. As there continue to be more and more smaller and newer funds created per year, that post triggered a bunch of emails and follow-up questions, so I collected them to put together a short FAQ with some more detail that will hopefully help someone else out there. What I’ve found is some folks want to budget for time or meetings, and the like, and then when I share with them the actual stats, it’s both painful (see below) but also helpful to see it how it went down. It is mostly a random process, and now looking back, I was extremely fortunate this all happened relatively quickly.

Basic Stats…

Time for materials/strategy prep? 4 months
Time “in market”: 6 months
Time to close: 2 months
Number of LPs interacted with: 200+
Continue reading "Brief FAQ From Haystack IV Fundraising Experience"

Brief FAQ From Haystack IV Fundraising Experience

Earlier this year, I wrote a post detailing how I was able to transform Haystack into an institutional fund. As there continue to be more and more smaller and newer funds created per year, that post triggered a bunch of emails and follow-up questions, so I collected them to put together a short FAQ with some more detail that will hopefully help someone else out there. What I’ve found is some folks want to budget for time or meetings, and the like, and then when I share with them the actual stats, it’s both painful (see below) but also helpful to see it how it went down. It is mostly a random process, and now looking back, I was extremely fortunate this all happened relatively quickly.

Basic Stats…

Time for materials/strategy prep? 4 months
Time “in market”: 6 months
Time to close: 2 months
Number of LPs interacted with: 200+
Continue reading "Brief FAQ From Haystack IV Fundraising Experience"

Looking Back On Tech Startups And VC In 2017

Here’s my “Year In Review For Tech VC & Startups, 2017 edition.” For the past few weeks, I’ve jotted down notes on my iPad w/ Pencil, and sort of dreaded the act of writing this given the overall stench of 2017. Yes, there were some bright spots. Focusing now only \in the world of tech startups and the investment firms which fund them, most of the major stories and developments are hard stories, but you’ll also see below many are thankfully moving (even if slowly) in a better, more equitable direction — though the process of getting there is a bumpy road.

The key thread running through the big stories in tech startups and investing in 2017 centers around the increase in three characteristics: 1/ the distribution power conferred to incumbents; 2/ increased global money supply seeking alpha in tech; and 3/ significantly more transparency in the information market.

Continue reading "Looking Back On Tech Startups And VC In 2017"

Looking Back On Tech Startups And VC In 2017

Here’s my “Year In Review For Tech VC & Startups, 2017 edition.” For the past few weeks, I’ve jotted down notes on my iPad w/ Pencil, and sort of dreaded the act of writing this given the overall stench of 2017. Yes, there were some bright spots. Focusing now only \in the world of tech startups and the investment firms which fund them, most of the major stories and developments are hard stories, but you’ll also see below many are thankfully moving (even if slowly) in a better, more equitable direction — though the process of getting there is a bumpy road.

The key thread running through the big stories in tech startups and investing in 2017 centers around the increase in three characteristics: 1/ the distribution power conferred to incumbents; 2/ increased global money supply seeking alpha in tech; and 3/ significantly more transparency in the information market.

Continue reading "Looking Back On Tech Startups And VC In 2017"

Podcast Holiday Listening 2017

This fall, I wanted to go on a “Podcast Tour” to talk about the new Haystack Fund and also re-engage with one of my favorite mediums, audio. Here’s a quick holiday round-up of all the shows from this fall, with two more set to be released (Origins, by Notation Capital; and Reboot v2, with Jerry Colonna) some time in January. It’s hard to share podcasts socially and people listen in different formats and on different players — I use Overcast for iPhone at 1.5x speed and love it — so here’s a rundown of all the links. If you’re stuck commuting over the holidays and/or need extra help falling asleep for a post-meal nap, listen to one of my interviews at 1.5x speed!

20 Minute VC (released 10/23/17)

The Continue reading "Podcast Holiday Listening 2017"

Podcast Holiday Listening 2017

This fall, I wanted to go on a “Podcast Tour” to talk about the new Haystack Fund and also re-engage with one of my favorite mediums, audio. Here’s a quick holiday round-up of all the shows from this fall, with two more set to be released (Origins, by Notation Capital; and Reboot v2, with Jerry Colonna) some time in January. It’s hard to share podcasts socially and people listen in different formats and on different players — I use Overcast for iPhone at 1.5x speed and love it — so here’s a rundown of all the links. If you’re stuck commuting over the holidays and/or need extra help falling asleep for a post-meal nap, listen to one of my interviews at 1.5x speed!

20 Minute VC (released 10/23/17)

The Continue reading "Podcast Holiday Listening 2017"

The Breakout Tech Company Of 2017

For a while, on this blog, I attempted to pick one startup for that year which truly “broke out” of its shell. Dialing back the clock, one could say 2011 was Uber and Airbnb; in 2012, I wrote about Stripe; in 2013, I wrote about Snap; in 2014, I prematurely said there were none but then backtracked when Slack exploded; in 2015, I didn’t write one, and in 2016, my thesis was the big tech incumbents would grow even more powerful from the web’s and mobile’s network effects that startups wouldn’t even have the chance.

Now with 2017 nearing the end, I’m back to the point where I can point to this year’s tech breakout company: Coinbase. I know, it’s likely an obvious pick, but I unpacking “why” is a fun exercise I’ll attempt below.

Right Person(s): Founded by Brian Armstrong and Fred Ehrsam, blending backgrounds in Continue reading "The Breakout Tech Company Of 2017"