Free Trade at High Speed

When I saw this news story tweeted by Bill Gurley something jumped out at me that was different than Bill took away:

Rocket Internet feeling pressure from street towards portfolio profitability. Perhaps we are tuning a new page. https://t.co/yjwksOVH5A

— Bill Gurley (@bgurley) October 22, 2015

Inside the story it describes Rocket Internet’s standing in the European startup hierarchy as such:

The Berlin-based group [is] Europe’s largest Internet company

I am not 100% sure this is true, and it obviously depends on how you measure it, or account for the fact that there are a couple billion in cash on Rocket’s balance sheet. But it’s a close enough approximation to make you wonder: how did Europe … Read More »

The Fax Machine Died When I Wasn’t Looking

Of course, I’ve known the fax machine’s days were numbered for a while now. The fact of it’s death is no surprise.

But I realized today that I can’t remember the last time I sent or received a fax.

As recently as five years ago, I felt the need to have an “all in one” printer at home with a fax machine hooked up to the phone line, in case I needed to send something — likely a signed document. And for about a decade I’ve had an eFax number that I pay to be able to receive faxes and get them as a pdf — trust me it seemed cutting edge when I signed up for it.

Checking my email, I find the last fax I received was in November 2014, ironically from Silicon Valley … Read More »

An Ad-Blocking Compromise

The debate over ad-blocking, spurred by the OS-level support for ad blockers in iOS9, has the feel of a religious war to me. People on both sides are making arguments as to why they are right, as if it would convince the others, but nobody is listening or really open to a new point of view. Be that as it may, I am going to foolishly wade in with a compromise proposal for “site blockers” instead of ad blockers.

Many good points have been made in the existing debate. Dan Primack argues that reading people’s sites while blocking their ads is akin to stealing. You are taking what you want, the content, but saying “no thanks” to paying for it by viewing the ads posted alongside it. I Read More »

iPhone 6 vs Samsung S6, Android vs. iOS: My Experience

After switching to an Android (Nexus 5) as a primary phone for over a year, I came back to iOS with the launch of the iPhone 6. I felt the new iOS and new Apple phone addressed the key things I went to Android for: bigger screen and 3rd party keyboards were a couple of big things for me. Once back on iOS, I immediately missed Android, and found iOS 8 to be less than I expected: it was buggy (particularly 3rd party keyboard integration, also calendar and others) and inflexible (what if I wanted to open Google Maps instead of Apple when I clicked on an address in my calendar?)

So I bought a Samsung S6. For the last six weeks, I have been using the two in parallel and carrying both (a lot of pocket weight!) On … Read More »

Dilution vs. Death

Thanks Laff4K for CC-A photo

I was chatting with a talented and smart founder/CEO in our portfolio about the Series B funding round he is going out to raise for the company, and the subject of dilution came up.

We had a conversation I have had many times: how much money to raise, and at what price. Specifically, he was sensitive to the amount of dilution he would take in the next round of funding. He owns approximately 20% of the company now and thinks things are going well. Ideally the company might raise more money at a $150M valuation, but if the market won’t support that, and offers came at say $100M, his inclination would be to raise a small amount of money and make more progress and go out later to … Read More »

“A book with a couple of legs sticking out.”

Also published on Medium.

I realized in 2013 that I had stopped reading books.

It wasn’t intentional —things got in the way, like life, learning how to do venture capital, three kids under 8 years old, the Warriors improbably beginning to figuring out how to play professional basketball. Dumb reasons for not doing something so important.

I was at a dinner event and Tim Ferriss asked: “What book do you give the most as a gift?” — and I really had no answer to this question. Not only because I am a bad person who doesn’t give books as a gift, but actually because I wasn’t making time to read books. Naval Ravikant (our host) suggested The Secret Race, Tyler Hamilton’s absolutely fascinating account … Read More »

A Startup CEO’s Guide to Burn Rates and Vaporization


The alarm has sounded.  A three-alarm fire, with alarms named Bill, Fred and Marc.  Burn rates are too high, change course or risk the consequences.

A CEO might be forgiven for asking: “that advice might have been more helpful before I hired those extra hundred engineers, and leased the fancy SOMA exposed-brick office to house them in.  Changing course on burn-rate now will be a lot harder than it would have been a year ago.”

To which I would say: suck it up and go run your business.  The past is past, and the decision you need to be focused on as the CEO is:  what should I do now?  The board is not running your business, they merely advise you, and you are ultimately responsible for making the correct decisions.

The question remains:  What should I do now?


The Past is History, … Read More »

Winning Slowly

Marc’s tweet today was timely, as this is an issue I have thought a lot about through my career (both entrepreneurial and investing.

Silicon Valley has embraced the idea of early testing and market feedback wholeheartedly, and ushered in a much more capital efficient era of startup building.  It used to take $10M+ to get a website off the ground, now it is generally live before the first outside capital comes in.  While this speaks volumes about the state of programming tools, cloud services, and other catalysts to development, it also speaks to the ethos of getting a “minimum viable product” live and in consumers hands.  Once out in the world, best practices of the lean startup encourage you to analyze the metrics and iterate on the product based on what you learn.  Startup construction has moved from … Read More »

#TBT – What Series A Fundraising Looked Like in 1999

Times have changed pretty dramatically since I started my first business in 1999, and I thought for throwback Thursday it would be interesting to share with the young’uns what Series A fundraising looked like back in 1999.

My business was then called InsightMarket, as a placeholder, and we thought we would call it WannaBet. We eventually launched as Flutter.com and it became Betfair when we merged with our biggest competitor.

I think our financing was extremely typical of the era — but how does the Series A process of 2014 compare with fifteen years ago?

Take a look through this fundraising deck and marvel at how risky a Series A investment was in 1999 – how little we knew about the product, the customer, acquisition, product-market fit.  This 14 page deck was the entire fundraising pitch — there was nothing else, no model, … Read More »

Foreign Exchange

As a bunch of you asked for it, my recent discovery on moving large ($10K+)  chunks of money from British Pounds or Euros to Dollars (and back).  (For smaller amounts, I’m told PayPal works well but I haven’t tried it.)

Here’s the challenge I have had:  if I want to move it from a bank in the UK to a bank in the USA, I have to go through a complicated process to initiate the movement – often requiring me to be in the country where the money is, which is rarely where I am.  So I am in the bank’s office in London, or on the phone with them at 3am, and go through an hour of bureacracy (ID checks, paperwork, waiting) until the money is ready to be wired.  Then, they call their exchange desks … Read More »

From the Blog

The Fax Machine Died When I Wasn’t Looking

Of course, I’ve known the fax machine’s days were numbered for a while now. The fact of it’s death...

An Ad-Blocking Compromise

The debate over ad-blocking, spurred by the OS-level support for ad blockers in iOS9, has the feel of a religious war to me. People...