VC/Founder partnerships and the cycle of destructive deduction and creative induction

I recently read Boyd (h/t and thanks to rands) and it got me thinking about the role of the founder and the VC in a successful partnership. There is a stark difference in the mindset and approach required for founders and VC’s to maximize their contribution to a company. Winning depends on each knowing their role and respecting the role of the other.

The founders I work with know that a critical part of my working style is knowing when to be quiet. I prefer to create silence, even awkward, uncomfortable pauses after a question or a reframing of a challenge because when founders step in and fill the gap in conversation, the quality of the discussion goes up. Every. Single. Time.

My job is to help take a mental model apart. I push founders to pull at the building blocks of the model in an effort to topple the

Continue reading "VC/Founder partnerships and the cycle of destructive deduction and creative induction"

Local tech ecosystems: Stop comparing yourselves to Silicon Valley

From Silicon Alley to Silicon Beach, existing tech hubs and emerging ones long to be seen like the Valley: the self-proclaimed epicenter of all things tech. But why is that? When did living in San Francisco become a necessary prerequisite for being a startup founder or employee?

As a New Yorker, I’m a bit biased to the Big Apple — the hustle and bustle of the city and the intrinsic drive that people have here opposite of our laid-back counterparts in the Bay. There are hundreds of tech companies that make up our local ecosystem, yet we still seem to come second to San Francisco. A big blow to the empire state, but an even bigger blow to cities on the horizon.

Emerging hubs like Miami, Raleigh/Durham, Dallas, Nashville, Cincinnati, Detroit and others deserve the same effort, education, and access that we pour into the Bay. Tomorrow’s next tech leaders and talent Continue reading "Local tech ecosystems: Stop comparing yourselves to Silicon Valley"

Local tech ecosystems: Stop comparing yourselves to Silicon Valley

From Silicon Alley to Silicon Beach, existing tech hubs and emerging ones long to be seen like the Valley: the self-proclaimed epicenter of all things tech. But why is that? When did living in San Francisco become a necessary prerequisite for being a startup founder or employee? As a New Yorker, I’m a bit biased to the Big Apple — the hustle and bu…Read More

20VC: The Future Business Model For Drones & Why Enterprise Drones Need To Be As Boring As Possible with Jonathan Downey, Founder & CEO @ Airware

Jonathan Downey is the Founder & CEO @ Airware, the startup that allows you to make better-informed decisions with aerial date, captured by drones. They have raised over $65m in VC funding from some of the very best in the industry including a16z, Kleiner Perkins and Google Ventures just to name a few. Jonathan is also the General Partner @ Commerical Drone Fund, making $250K-$1m investments in early stage companies in the commercial drone space. Prior to Airware, Jonathan was a commercial pilot and a flight controls engineer @ Boeing.


In Today’s Episode You Will Learn:

1.) How Jonathan made the move from commercial pilot to startup founder with one of the hottest drone startups, Airware?

2.) What has been the catalyst for the rising belief in the potential for drones? What has changed about the landscape to make them now not only a commercially viable Continue reading "20VC: The Future Business Model For Drones & Why Enterprise Drones Need To Be As Boring As Possible with Jonathan Downey, Founder & CEO @ Airware"

Market Caps & The 2% Rule

One way to assess whether a startup idea is in a good market is to ask what are the market capitalizations of the biggest companies in that sector. For example in consumer internet, Google ($560 billion) and Facebook ($370 billion), and in enterprise software Microsoft ($460 billion), and Oracle, ($167 billion) are all large, high margin businesses.

Market caps in a pre-existing industry[1] tend to be proxies for the potential of the idea you are working on. There are three reasons for this:
1. The market capitalization of a set of companies reflects revenue in the market, growth rate of revenue and earnings, and the margins of the companies.
These core metrics used by wall street to value a stock are all metrics that help you understand whether a market is overall large, growing and profitable - all signs of a good market to enter.

2. Often, potential competitors Continue reading "Market Caps & The 2% Rule"

Dear Mr President , My Suggestion for Infrastructure Spending

I happen to be a fan of the government investing money into what is commonly called infrastructure projects.  I strongly believe that any reasonable businessperson, even one who works for the government, should be able to invest money at 1% interest rates and get a better than 2% return on taxpayer money. But I think its time to rethink how we spend a big chunk of that money.

If it was me spending the money, I would take 100 billion of the proposed $ 1 Trillion dollars in infrastructure investment and invest it in Robotics.

I would invest it in the companies that do R&D, software, and design for robots and every other facet of the Robotics Industry.

Unfortunately, none of the companies that actually make the robotics are based here in the USA. That’s a problem that needs to be solved.  We need to help develop domestic companies much like Continue reading "Dear Mr President , My Suggestion for Infrastructure Spending"

GOAT: In Defense of the Pivot

The “pivot.” If you spend much time in the VC industry or reading tech press, it starts to sound like a cliche. Like a punchline. A last, desperate scramble to make something out of a business that, rightly or wrongly, couldn’t make their model work the way originally thought or how early metrics had indicated it might.

And when you’re surrounded by examples of failed pivots, it can be easy to become jaded about them. For every successful pivot like a Twitter, Instagram, or Slack, there are countless others, high profile and low profile, that never managed to find product-market fit and simply ran out of runway.

I sometimes say be careful with pivots, as the referee will blow the whistle for traveling. You can lose your key players, key coaches and influential fans and supporters. And yet, sometimes that pivot can create a clear path to the basket leading to

Continue reading "GOAT: In Defense of the Pivot"

Who is #LongLA?

This is a list of known firms and individuals with a home base or whose investment focus includes Southern California. It includes Accelerators, Angels, Corporate VCs, Family Offices, Hedge Funds, Seed Funds and Traditional VCs.

The list was inspired by @shaig‘s seed fund google doc. Tweet or comment additions, corrections or deletions. “Home base” definition and right to add is at my discretion. Investors w/ known funds are listed under Fund Name (ie: Matt Mazzeo via Lowercase Capital and Michael Eisner via Tornante Company)

Google Doc is accessible here. Originally created July 5, 2014 and has been modified many times.

#LongLA Tech Investor List

Imaging, Snapchat and mobile

For the first time, pretty much everyone on earth is going to have a camera. Over 5bn people will have a mobile phone, almost all will be smartphones and almost all will have cameras. Far more people will be taking far more photos than ever before - even today maybe 50-100 times more photos are taken each year than were taken on film. 

Talking about 'cameras' taking 'photos', though, is a pretty narrow way to think about this - rather like calling those internet-connected pocket supercomputers 'phones'. Yes, the sensor can capture something that looks like the prints you got with a 35mm camera, or that looks like the footage a video camera could take. And, yes, it's easier to show those images to your friends on the internet than by post, and easier to edit or crop them, or adjust the colours, so it's a better camera. But Continue reading "Imaging, Snapchat and mobile"

News Roundtable! Ari Levy, CNBC & Rolfe Winkler, WSJ: Walmart & Jet, Google & anti-trust, Uber & China, Elon & Energy, CEOs & bad behavior

Hi everyone, Producer Jacqui here. Ari Levy of CNBC and Rolfe Winkler of The Wall Street Journal joined @Jason for a must-see News Roundtable on This Week in Startups. An amazing discussion that kicked off with big deal of the week, Walmart snapping up for $3b, that crackled on to Google, the government, anti-trust, the entire U.S. debt problem, the Chinese Market, the very future of energy (featuring, naturally, Elon), and the latest in startup CEOs behaving badly. And more.

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And watch here! 🙂

Some key discussions

The big deal of week is being bought for $3B by Walmart. What’s behind the deal? has been around since 2000 and has never bridged the gap with Amazon, remaining the #2 player in e-commerce. Could & CEO Marc Lore be the Continue reading "News Roundtable! Ari Levy, CNBC & Rolfe Winkler, WSJ: Walmart & Jet, Google & anti-trust, Uber & China, Elon & Energy, CEOs & bad behavior"


I'm going to say something very unpopular in my world: Trump is right about some big things.

He's right that many Americans are getting screwed by the system.  He’s right that the economy is not growing nearly fast enough.  He's right that we're drowning in political correctness, and that broken campaign finance laws have bred a class of ineffective career politicians.  He may even be right that free trade is not the best policy.  Trump supporters are not dumb.

But Trump is wrong about the more important part: how to fix these problems.  Many of his proposals, such as they are, are so wrong they’re difficult to even respond to.

Even more dangerous, though, is the way he's wrong.  He is not merely irresponsible.  He is irresponsible in the way dictators are.

Trump's casual racism, misogyny, and conspiracy theories are without precedent among major presidential Continue reading "Trump"

New Investment: Robin

We all know the feeling.  We have an office conference room reserved, we go to that room to find someone in it, and then the awkward dance begins.  Do I go look for another space to be polite?  Are they really wrapping up the meeting?  Do I knock?  How senior is the person in there? Does it matter?  Should I do another walk by?  We now schedule over 25 million meetings a DAY, and this is a familiar refrain in nearly all of them.

Robin wants to change that. And, I’m very excited for FirstMark to lead the company’s Series A.

Robin is a better way to manage meeting rooms and office resources. It is software, a mobile app, and a tablet display (optional) outside rooms that syncs to your calendars in Google, Office 365, and Exchange. The platform then becomes a search engine for your office, enabling users to

Continue reading "New Investment: Robin"

buddying up to another series a

for the past year, many of the smartest investors and pundits i follow have claimed some variant of the following: the mobile market for apps is maturing. they’re probably mostly right, as it’s hard to drive distribution on either platform (for different reasons), the venture appetite to take on such risk has been satiated,  so much of the echo chamber has moved on to new exciting platforms like virtual reality, automobiles, space, and beyond.


don’t get me wrong, vr, cars, and space are all fascinating areas — but, as a long-time software engineer dating back to palm all the way to twitter, to me mobile hasn’t yet matured. it may never mature, what with billions of people worldwide who will come online over the next decade, new features (as recent as google instant apps), and interesting overseas forks of android, especially in asia. put another way, one investor’s maturing market
Continue reading "buddying up to another series a"

Gboard — Google’s brilliant strategy to leapfrog Apple, Facebook and iOS messengers

Google’s new iOS keyboard seeks to own the key mobile use case — messaging.


Last week, Google launched the Gboard to stellar reviews. It’s a 3rd party iOS keyboard that allows for searching and sharing in context on the phone. It’s a brilliant strategy for ensuring that Google is central for information discovery. It has the potential to be more strategic than the default search deals Google has previously struck with iOS Spotlight and Safari. To top it off, after nearly a week of playing with it, I love it.

It’s a strong keyboard and has a slew of delightful features like emoji autocorrect [search pizza], predictive searches [text want to get a drink tonight], and of course the core search and share card metaphors.

Up until now, first class keyboards that have done well on Android have had a hard time replacing the primary keyboard on iOS. It’s not an easy Continue reading "Gboard — Google’s brilliant strategy to leapfrog Apple, Facebook and iOS messengers"

TapInfluence Taps $14 Million for Influencer Marketing

TapInfluence, a platform that connects brands with influencer marketers to promote their content online, has raised $14 million in Series B1 funding.

The company, incorporated as TapInfluence Inc., has a network of about 45,000 vetted influencers. TapInfluence uses Watson, IBM’s natural-language-processing computer, to create demographic profiles of each influencer’s audience, to help marketers target their campaigns. TapInfluence also works with the Nielsen Catalina Solutions to provide its clients with attribution data on the conversions driven by each campaign and influencer. This includes return-on-investment data for both online and in-store transactions.

Last year it transitioned from a fee-for-service model to a software-as-a-service one.

TapInfluence is harnessing advertising dollars from brands that are beginning to embrace influencer marketing at scale, running hundreds of campaigns instead of reaching out to individual influencers, said Chief Executive Promise Phelon. The company’s clients include WhiteWave Foods, the maker of Silk soy milk.

Last spring Continue reading "TapInfluence Taps $14 Million for Influencer Marketing"

No Neurozone for Trump

We need a Manhattan Project for the brain, a place where entrepreneurs, startups, established companies, and talented people from all over the world come together to solve some of the brain's most vexing problems - which are also some of the world's most pressing problems.

What’s your startup’s superpower?

The sky is falling in the venture financing market!  Warnings, exhortations and admonitions are being written and spoken everywhere.  A market in which capital was abundant is now increasingly constrained.  So what’s a startup to do?  The reality is that you probably shouldn’t change anything about your business if you’ve been running it rationally.  Capital is really only a tool at the early stages.  Capital enables you to exist, it doesn’t enable you to win.  More important than ever is being able to answer one question.  What are you going to be the best in the world at doing?  Answering that question will help your company focus on unlocking its superpower, the skill or asset that truly sets it apart in the market.  And that will allow you to survive, and even thrive, in any fundraising environment.  

As a VC, I see a large number of

Continue reading "What’s your startup’s superpower?"

Debunking The Skill Gap in Daily Fantasy

Daily Fantasy Sports are under a full on assault: allegations of “insider trading,” a hyper aggressive (if not overwhelming/annoying) advertising strategy, and multi-directional claims that DFS can’t be beat because it involves too much skill. There are lots of legitimate concerns which I will address in future posts over the coming weeks. But the most […]

The ‘Oh, Shit!’ Moment When Growth Stops

Investors tend to value growth over everything else because a business can’t get big enough to break out if it isn’t growing. Of course, there are a number of key performance indicators for managing a business well and toward profitability — which we’ve written about here — but there are still stomach-churning moments where growth trajectory was interrupted.

Sometimes it happens gradually, but in a surprising number of cases it happens suddenly: The business is growing one day, then it’s not growing the next. I’ve taken to calling these growth hiccups “Oh, shit!” moments for CEOs. So what do you do when the growth rocket judders? MORE


Creativity Today

Steven Johnson has an excellent long read coming up this weekend in the NYT Magazine.  It’s available online now.  Its title says exactly what it’s about: The Creative Apocalypse That Wasn’t.  In short, Napster was supposed to be a harbinger of doom for all creative talent as piracy and digital boogeymen were going to mean the end of any viable revenue streams in the creative industries. Steven explores digital implications for music, movies, books, and television in a pre-Internet context compared to today. It’s just great; I’ll refrain from stealing his thunder on conclusions (if the title didn’t already tell you everything).

Reading Steven’s piece, at the very end he had a tiny throwaway line about how two musicians separated by the Atlantic can collaborate on a work today, but he never elaborates on this half-sentence at all. I was instantly reminded of a recent episode of Song Exploder (a Continue reading "Creativity Today"