Category: Uncategorized

Are Great Entrepreneurs Crazy?

Posted on 11th April, by josh in Uncategorized. No Comments


 I’ve been thinking a lot about this exchange between two successful investors that popped up in my Twitter feed last week.

To make money as an investor, must you back unreasonable, mercurial, irrational entrepreneurs? This feels on the surface like it has a grain of truth to it. And both these guys have generated spectacular returns in their investment portfolios, so they should know what they are talking about.

Chris is most notable for betting big on Twitter, by acquiring a ton of common stock from employees and former employees, both for himself and on behalf of other investors. I don’t know Ev, Jack or Biz well, so I can’t personally grade them, but given that is Chris’ primary investment, he is likely referring to that. And if you’ve read Hatching Twitter, the book about … Read More »

Regulation and Startups

Posted on 31st March, by josh in Uncategorized. No Comments


This post originally appeared in PandoDaily.

How should entrepreneurs (and investors) factor the risks and challenges of regulation into their decision to start a company or invest in one? It doesn’t come up very often — regulation rarely intrudes on the fate of startups. Even if you are in a regulated industry, generally you can fly below the radar for quite a while.

Lately regulation has been in the news with discussions around a number of industries. Drones have entrepreneurs salivating at the disruptive opportunity for unmanned flight to empower delivery of goods, aerial surveillance, and more. Yet, the FAA is concerned about flying objects weighing several pounds or more crashing and injuring people or property. In the automotive industry, Tesla wants to sell cars directly to consumers, arguably in violation of long-standing franchise laws. Finally, … Read More »

The Perfect Valentine

Posted on 15th February, by josh in Uncategorized. No Comments

I’ve found the perfect Valentine’s gift for that geek girl in your life.  Actually, it works fine for non-geeks but given that you are reading my blog, I’m pretty sure your wife or girlfriends is somewhat of a geek.

That gift is a subscription to RocksBox.  It’s an affordable subscription to great jewelry — have something new, fresh and beautiful to wear every day, all for less than $20/month.  Not cheap plastic stuff, but real high quality pieces, generally $100+ pieces with a lot of style.

On behalf of Matrix Partners, I have just led the company’s most recent round of funding, and I couldn’t be more delighted.  When I met the founder Meaghan Rose the first time, I was very impressed, but early stage commerce ideas are hard to evaluate in advance of market data other than … Read More »

In Defense of MBAs

Posted on 11th February, by josh in Uncategorized. No Comments

Dan Primack at Fortune re-started a discussion around whether MBAs make good entrepreneurial founders, based on Chamath’s remarks at an HBS event.

While I’ve commented on this on a Quora answer in the past, I’ll weigh in again… While an MBA certainly doesn’t mean you’re going to be a successful founder, it certainly won’t hurt and it might even help.

I went to Stanford GSB, and a great entrepreneur and professor, Irv Grousbeck, inspired me with the notion that I was qualified to be my own boss, and that the life of an entrepreneur was a virtuous choice.  I am certain that without his inspiration, I would not have chosen that path, and it was one of the most important decisions in my life.  So on your scorecard of MBAs not qualifying founders to start billion dollar companies, we can … Read More »

Q&A: Cold Email

Posted on 18th September, by josh in Uncategorized. No Comments

Question:  Will an investor consider an investment via cold email, if that email contains complete info about the business?

In a world of no scarcity, I would read every email from an entrepreneur and take every coffee with them.  I rarely fail to enjoy hearing about someone’s business.  And, if you could remove the financing agenda, I would probably enjoy all of them.  (What I mean is: since I turn down 99 out of 100 investment opportunities, and in general decide quite quickly, I enjoy the meeting itself but that enjoyment is reduced by thinking about having to say no the the entrepreneur, and by the fact that my financing agenda and their fundraising agenda dilutes the quality of discourse in the meeting: they don’t want to talk openly about the things that are likely to kill their … Read More »

Leaving iOS

Posted on 18th September, by josh in Uncategorized. No Comments

After 6 wonderful years, I’ve left iOS for Android.  Thanks Apple, it’s been fun, I have no complaints.   Well, except that you’ve turned the population of people I interact with into robots who stare at their devices for most of the day, but ultimately it’s hard to hold you accountable for that.

My partner @antrod predicted I would flip back within a couple weeks, but it’s not happening.  I inadvertently burned the boats when my wife’s phone got stolen this week, and I gave her my iPhone 5.  No easy way back.

I picked up one of Google’s very cheap, very good Nexus 4 phones ($250 with no contract) and off to the races.

Why switch?

Fingerprints be damned, I think the pace of hardware evolution of the iPhone is slow at this point.  I think Android is gaining steam … Read More »

Opportunities in Digital Gambling

Posted on 13th February, by josh in Uncategorized. 1 Comment

For those who don’t know, I co-founded the company that became Betfair, and have a keen interest in the space of online gambling.

I continue to wonder how opportunities are going to develop for startups in this space in the US.  Outside the US, most of the companies that have been built have pretty much been an online representation of what takes place offline.  (Betfair being one of few exceptions).  Consequently, most of the spoils have gone to pre-existing (pre-internet) companies who leverage their brand and presence to build an audience.  If all everyone does is put blackjack online, it boils down to a game of  customer acquisition and those with big brands have an unfair advantage.

Which bring me to the question of: what, if any, is the opportunity for startups in the USA if gambling gets legalized?

First, an aside for … Read More »

The “Bad News” Call

Posted on 13th September, by josh in Uncategorized. No Comments

One of my CEOs just surprised me!  I just did a pre-board meeting call, scheduled at the last minute.  Actually, I just did two of these in two days.

I think of this as the “bad news call” — when the CEO sends me an email and says he just wants to catch up on something before the meeting, but gives no indication of what it is, I’m left speculating:  who’s quitting?  who did we fire?  how badly did we miss the quarter?

It’s borne of a good impulse: if you have bad news, you should absolutely get out in front of it, and diffuse it 1-on-1 with individual board members.  If you don’t, you risk the conversation going in a way you didn’t expect, or the group getting in a downward spiral.  It’s absolutely best practice to handle it this way.

But … Read More »

Quora Elevates the Web

Posted on 14th May, by josh in Uncategorized. 3 Comments

Quora just announced its Series B fundraising, and I’m pleased to be a part of it, as Matrix is one of the large investors in the round.

I’m a huge fan and avid user of the site, and I think it has the potential to be one of the cornerstone web properties, and help make the world a better place.

I’ve spent a ton of time in this shared knowledge category on the web over the last 8 years.  In 2003, when I was looking to start my next business, I came onto this idea of community shared knowledge.  In the post-bubble era, no one was investing in content for the web because there was no economic model to support it, but by 2003-04 a number of things were happening.  Wikipedia was just beginning to … Read More »

A Disconcerting Lack of Hubris

Posted on 9th April, by josh in Uncategorized. 1 Comment

I agree with everything in @jasonfreedman’s outstanding blog post about raising seed capital in today’s environment.  I urge all seed stage entrepreneurs to give it a thorough read.

As Jason says, no investor should begrudge entrepreneurs for a strong fundraise in an attractive early stage financing market — but keep some perspective, this is a long game, and you can’t win it today at your seed stage financing.

I wasn’t able to make the YCombinator demo day this time due to a board meeting.  But For context of what I’m talking about, let me anonymize and share a representative email exchange from the previous demo day:

On Wed, Aug 24, 2011 at 1:24 PM, Josh Hannah <> wrote:

Impressive presentation and interesting business.  Would love to learn
more, if you’d be up for a meeting?


Hey Josh,

We’d definitely love to talk!  We’ll look for … Read More »

From the Blog

Are Great Entrepreneurs Crazy?


 I’ve been thinking a lot about this exchange between two successful investors that popped up in my Twitter feed...

Regulation and Startups


This post originally appeared in PandoDaily.

How should entrepreneurs (and investors) factor the risks and challenges of regulation into their...

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