Venture Studio (10): Ben Lerer, CEO of Thrillist

This is Episode (10) of Venture Studio

Welcome to this week's conversation with Ben Lerer, CEO of Thrillist, which he started five years ago in NYC as a daily email/city guide chock full of product and experiential recommendations for a very underserved market- urban-dwelling guys.  Since then, Ben and his team have scaled the company to over three million subcribers, 90+ employees and into approximately 20 cities around the country. They have also just made their first acquisition: JackThreads and have launched a Rewards program.

I would say that "evolution" was definitely one of the major themes of our talk. Ben talks not only about the evolution of his business but also of his own from a "do everything kind of entrepreneur" to a guy who now oversees a large and growing business with talented people in important roles. It's a transition that any startup entrepreneur should aspire to make one day.

We also discuss Lerer Ventures, (the seed investment fund he and his father operate). Here too we talk about his evolution as a seed investor.  Enjoy.

:20  -  What is the story of Thrillist and how it got started?

2:10 -  On getting funded by AOL veteran Bob Pittman of the Pilot Group

3:34 -  What's an average day like for Ben lately?

4:04 - "Thrillist is definitely hiring!"

4:35 - How has Ben's role at Thrillist evolved as the company has scaled?

5:13 - What's with the Bowie Knife? (ok, ok, it's plastic....) 

8:19 - Biggest lessons learned... (it's that focus thing again!)

10:04 - All about the JackThreads acquisition

11:40 -  Lerer Ventures & their evolution as seed-stage investors

14:24 - What are they looking for in terms of entrepreneurs they back?

15:02 - What is the Rewards Program and what's next for Thrillist?

Click Here for Venture Studio (11) w/ Jonathan Glick from Sulia

                  

               

Venture Studio (2): Professor Evan Korth of HackNY

This is Episode (2) of Venture Studio

Get to know our guest, a huge figure in NYC's technology ecosystem, Professor Evan Korth. 

In this conversation we discuss HackNY at length, the role of the University in New York's technology ecosystem, some of Evan's student teams (including Diaspora!), NYU's Innovation Fund, and his passion for teaching, mentorship and NYC.

(This excellent piece was released today on TechCrunch about HackNY 2011)

Click for Venture Studio (3) w/ Mark Loranger of Square 1 Bank

                  

               

Welcome to Venture Studio

As a new feature to my blog, I'll be posting my one-on-one conversations with entrepreneurs, hackers, founders, vc's, angels and others who comprise New York's vibrant tech ecosystem starting next week. Getting some great guests working on fascinating projects! Our parter organizations below will be helping with identifying guests and getting the word out about the show. Stand by...

For Episode 1 of Venture Studio click here

Co-Hosting Organizations:

           
                                                        The Startup Genome Project

Angel Profiling (4): The Wild and Wooly (and Expanding) Angel Universe

 This is part of my Series on Angel Investing.

In the first post of this mini-series I pointed out that the landscape of angel investing is quite sprawling and diverse with many constituents. In fact, many are calling 2010 the "Year of the Angel", although this is often uttered ironically by those who believe we are witnessing (and participating in) a seed-stage bubble these days with requisite inflated valuations. During my recent interview with him, Mark Suster made the classic remark that "everyone is an angel today" and it's true. The Venture Hacks Angel List seems to be adding new angel investors by the hour!

So bubble or not, as promised, below is an infographic that illustrates this rapidly expanding and overlapping angel universe in a tongue-and-cheek manner. The entire wild and wooly cast of characters are represented below including the aforementioned "Susterian Mugs", the ubiquitous Friends and Family investors, the two varieties of Maniacs, the Celebs and of course, the so called "Pro-leaguers" or nearly extinct "SuperAngels" (most of whom are now running their own micro-funds).

The full dramatis personae are as follows:

Friends and Family supporting "our own": The largest contingent of all pumping $60B/year into startups

"Mugs" who don't know what the heck they are getting into and don't realize it (me circa 2001)! 

Maniacs Tilting at Windmills who don't know what they're doing, realize it, and don't care

Maniacal Wisemen Tilting at Windmills Although these guys are maniacs, there is a method to their madness. They are trying to fund companies that will make a massive and positive difference in the world and solve important problems and carry their checkbooks with them. Paige Craig is one such dude.

"Weekend Warriors" of varying skills and motivations, (this includes participants in Angel Groups)

Entrepreneurs Giving Back and supporting the younger generation

Celeb Angels Ashton Kutcher, Will.i.am, etc.

VC Angels VC's who do some angel investing on the side

Professional Angels (the pro-leaguers or "super-angels" who more and more are becoming micro-VC's)

What I call "Dark Angels" These characters are not often seen in the light of day. They are elusive, shun the spotlight, and yet appear somehow through various corporate vehicles on the cap tables of many of the top-tier funded companies out there. The further I've descended into the rabbit hole of angel investing the more I run into these figures. It's amazing really as the few I've met are serious bad-asses with deep domain expertise that just like to keep a low profile for whatever reason. The last "dark angel" I met showed up at an evening meeting the CEO had arranged a few weeks ago wearing darkly- tinted glasses and hardly said a word. To me this is the most fascinating category of all.

Some Reflections and Best Wishes for the New Year: Here Comes 2011!

As we officially launch the New Year today, a few thoughts occur to me that bear mentioning:

1) I would first like to thank all the readers of this blog for your kind encouragement, support, comments, valuable time and insights shared over the course of this past year. I wish you all the best for 2011 in both your entrepreneurial pursuits and personally. It has been terrific getting to know and learning from so many of you. Here's to another great year!

2) If you want to receive this blog via email in 2011 to make things easier, just click here. I'll also be sending out invites for readers to receive email updates within the next few days.

3) This year I'm looking forward to continuing my work on the following projects and activities:

• For those of you launching new businesses I'll definitely be continuing my Zero to One Series here.
• I'll continue to develop the crowdsourceable entrepreneur/venture maps which are part of what we're calling the Startup Genome Project. The goal of this project is to provide a powerful and rich resource for any entrepreneur in the world who wants to familiarize himself/herself with their entrepreneurial ecosystem and beyond. 
• I'll also be accelerating the Venture Studio Series with video interviews of the various dramatis personae of our incredible American entrepreneurial ecosystem.
• I'm really looking forward to working together with my newly elected colleague on the NY Tech Meetup Board, Evan Korth, to increase connections between our universities and the tech community here in NYC.
• Psyched to keep putting on great entrepreneurship events (and Happy Hours of course!) with the New York Venture Community.
• Working with the burgeoning entrepreneurial community at Columbia University through our ongoing Entrepreneur-Office-Hours, with Columbia Venture Community, and of course spinning-off excellent faculty spinoffs through my work at Columbia Tech Ventures.

4) Lastly, if you're looking for a dose of inspiration as you kick-off your year, see this video below in which Hans Rosling shows how the quality of life of humans worldwide has evolved/transformed and accelerated over the course of the past two centuries.

It occurred to me that Rosling's story is in many ways the story of entrepreneurship and innovation. We have and will continue to change the world for the better. That's certainly something to shoot for as the New Year arrives.

Angel Profiling (2): Global Directory of Blogging Angels

 
This is part of my ongoing Series on Angel Investing.

As promised in my last post I am compiling a list of Angel Investors who blog. Obviously this initial list is incomplete and has inaccuracies, so please help out by making suggestions and corrections. 

You will note that not all of these blogs are about angel investing per se, as in many cases the blogs address the personal interests of the investors themselves which is consistent with our continuing exercise in Angel Profiling!

Click on this hyperlink to subscribe to my Global Directory of Blogging Angels.

PRO-LEAGUERS

Jeff Clavier (investor)

Chris Sacca (ex-googler, founder of lowercase capital)

Dave McClure (entrepreneur, 500 Hats)

Jason Calacanis (entrepreneur, ceo Mahalo, poker player)

Keith Rabois (entrepreneur, executive)

Chris Dixon (entrepreneur, co-founder Hunch, Founder's Collective)

Paul Kedrosky (investor, writer)

CELEBRITY ANGELS

Tim Ferriss    (author of 4 Hour Work Week)

Kevin Rose  (founder of Digg)

Will.i.am (musician, blackeyed peas)

Ashton Kutcher (actor)

ANGELS OF ALL KINDS

Max Levchin (entrepreneur, ceo Slide)

Bill Lee (entrepreneur, founder Remarq)

Naval Ravikant (entrepreneur, epinions, venturehacks)

Kevin Fox (entrepreneur)

Seth Goldstein (entrepreneur)

Auren Hoffman  (entrepreneur, ceo Rapleaf)

Joshua Schachter (entrepreneur, founder Delicious)

Gabriel Weinberg (entrepreneur)

Shervin Pishevar (entrepreneur)

Jeremie Berribie (entrepreneur)

Brock Blake (founder Funding Universe)

 Kimbal Musk  (entrepreneur, founder Me.dium)

Mitch Kapor (entrepreneur)

Howard Lindzon (entrepreneur, founder Stocktwits)

Joi Ito  (entrepreneur, founder, Creative Commons)

Alexander Muse (entrepreneur)

David Rose  (founder AngelSoft, NY Angels)

Esther Dyson (ED Venture Holdings)

Dave Lerner  (entrepreneur, Columbia Venture Lab)

David Tisch   (NY Tech Stars)

Roger Ehrenberg   (IA Ventures)

Gary Vaynerchuk  (entrepreneur, WineLibrary TV)

Pat Matthews  (entrepreneur, founder of webmail.us)

Micah Rosenbloom (entrepreneur, co-founder Brontes, Founder's Collective)

Caterina Fake (entrepreneur, Flickr, Hunch)

J. Basil Peters (angel investor)

Michael Parekh (investor)

Travis Kalanick (entrepreneur)

Stephen Gill (entrepreneur)

Eric Paley (entrepreneur, Founder's Collective)

Roy Rodenstein (entrepreneur, founder Going)

Jeff Miller (entrepreneur, founder Punchfork)

David Shen (product guy, former Yahoo)

Kip McClanahan (entrepreneur, TippingPoint, 3Com)

Dave Nakayama (former Yahoo)

Will Herman (entrepreneur, Innoveda, Viewlogic Systems) 

Bill Boebel (entrepreneur, webmail.us, Rackspace)

Marco Messina (entrepreneur)

JS Cournoyer (entrepreneur)

VC's WHO DO ANGEL INVESTING

Fred Wilson (Union Square Ventures)

Mark Suster (GRP Partners)

Brad Feld (The Foundry Group)

Roger Ehrenberg (IA Ventures)

John Frankel (FF Asset Management)

For Part 3 of this mini-series, click here.

Mapping the Whole Venture Ecosystem (or my new life as a Venture Cartographer)

                               
This is part of my various series on Venture Capital, Angel Investing and Entrepreneurial Culture.

It all started when it occurred to me that we were missing a nice visual map of Silicon Alley's early-stage ecosystem available for everyone to use. Entrepreneurs were always asking me about various angels and VC's and I just thought that such a map would be a good resource to which I could refer people. I also thought that adding the twitter addresses of all these investors would be a nice feature as well. So one night I did just that and mapped out New York's early-stage tech investor ecosystem and posted it here on my blog.

After receiving so much great encouragement and so many submissions and corrections, I thought I'd do the same for our neighbors to the north- my old stomping grounds- Boston! That took me a bit longer, of course, because the ecosystem is quite a bit larger than NY's coupled with the fact that I couldn't do most of it from memory. I haven't lived in Boston for over nine years now! 

Well, the encouragement and emails kept flowing. There was a real need for this. No one enjoyed wasting hours looking various funds up online or clicking through some spreadsheet or flipping through one of those venture capital directories for that matter. I knew then that I had to take the next step into what appears to be a new discipline- I think I am going to call it Venture Cartography.  :)

The Silicon Valley/San Fran map was soon to follow and I'm happy to say it is now up and running! Corrections, submissions, etc. more than welcome as usual. Bring it on!

At this point, however, I realized I needed help. I really wanted these maps to be interactive and provide richer information for us all. So I gave my friend Shane Snow a call. He is a super-talented entrepreneur, hacker, designer and journalist extraordinaire who can basically do anything. 

Our collaboration has resulted in this interactive map, which is a precursor to us mapping the venture ecosystem of the entire world in its component parts. Now all you have to do is just click on the city you are interested in and then click on any investor to get a good understanding of his or her background, investments, blogs, opinions, twitter-feed and the like. 

We've put a lot of effort into teeing this up, but this is meant to be crowd-sourced on an ongoing basis- so please- send us all the names, the people, the angels, the accelerators and the funds we are missing! You can email us here: info at venturemaps.co   (yep, that's .co, not .com)...

We'll be thankful for all the help you can provide. Apologies in advance to anyone we've left out.

I want to offer a special thanks to the folks who have given us excellent insight into their respective ecosystems, especially the venture investor and irrepressible gadfly Stewart Alsop  (@salsop) as well as my buddy JJ Freitag  (@jjfreitag) over at Azure Capital. Thanks guys!

Map of Boston's Early-Stage Tech Investor Ecosystem (Updated)

This is part of my Series' on Venture Capital and Angel Investing.

After I posted the recent map of Silicon Alley's early-stage venture ecosystem, a healthy number of people found it to be very helpful and several suggested I do the same for Boston.

Well, here's my first stab at capturing what is just a massive early stage venture ecosystem! Until you lay it out on a map, you just have no idea of the sheer sweep scope of the venture/tech community. Amazing stuff really.

Though I lived and ran my first business from Boston for a number of years, I'm going to ask for your help again- especially from the Bostonians among you! I'm sure I have made plenty of errors, I definitely need the twitter addresses of those investors that tweet- and I'd love to hear from the angel groups and angel investors in Beantown. Please keep the twitter addresses coming!

I'll be updating the map periodically based on people's feedback and will eventually put all these maps on an interactive and hyper-linked template.

As the print is currently quite small due to the sheer size of the map, simply click on it and it will open in a separate window. You may then use your zoom feature or simply click it again to enlarge once more at that point.

Looking forward to your feedback!

For the next post, a crowdsourceable map of the global entrepreneurial ecosystem, click here.

Map of Silicon Alley's Early-Stage Tech Investor Ecosystem (updated)

This is part of my various Series on Venture Capital and Angel Investing.

In that I am a heavy user of mapping software and think programs like MindNode are excellent visual aids, I decided to put together a first draft of the early-stage tech investor ecosystem here in Silicon Alley as a resource for entrepreneurs. As this is a first stab, I would ask your help in the comment section of this post letting me know about any early-stage investors I have left out and/or about any corrections of errors you come across on this map.

As the print is quite small due to the size of this map, simply click on it and it will open in a separate window. You may then use your zoom feature or simply click it again to enlarge once more at that point.

Looking forward to your feedback.

For the next post in this Series, click here.

A New Style of Russian Roulette

 

This is part of my ongoing Series on Entrepreneurial Culture and Venture Capital.

In the tech world there was of course Sergey and that little pet project of his (and Larry's) at Stanford we came to know as Google. Then there was Max and his partners- unfurling the behemoth of PayPal and then Slide.

In the fight game Andrei Arlovski appeared suddenly out of nowhere, shaking-up the heavyweight division in the UFC with some magnificent wins. But then came the ascent of the legendary fighter Fedor Emilianenko, also known as "The Last Emperor", who may be the greatest mixed martial artist the world has ever seen.

In boxing the amazing Klitschko brothers, Vladimir and Vitali, wear practically all the world's heavyweight championship belts between the two of them. Vitali also happens to hold a PhD and I am told both play a mean game of chess.

In high stakes poker Ivan Demidov exploded on the scene in 2008 making the final table at both the World Series of Poker and World Series of Poker Europe.

In chess the Russians have of course been absolutely dominant for almost a century. Kasparov went out on top as the world's #1 a few years ago, is running his own political movement, and now is throwing his support to his old nemisis, Karpov, in the latter's bid to become the new President of FIDE, the world chess federation.

Here in the US, the NBA has now cleared mega-billionaire Mikhail "The Giraffe" Prokhorov's purchase of the New Jersey Nets (not to mention the major stake in the Brooklyn arena in which they'll be playing). Any whiff of oligarchism is off the rose- this guy is 6'7", likes to jet-ski (check this out) and was wrongfully arrested a while ago in France for traveling with too many attractive women. They erroneously thought he was pimping. He was just living his life.

That brings us to the VC game where Yuri Milner and the boys at Digital Sky Technologies have made a huge splash. They swaggered in with some Goldman Sachs polish, rolled up in limos and started laying massive bets all over the table. Valuations were suddenly off the charts. Liquidation preferences? They thought you meant Stolichnaya. "No thanks, we'll just take common shares." Some players in the VC and PE community looked up bleary-eyed from the dingy tables they'd been playing all night and said, "what the f@#$ just happened?".  Meanwhile, entrepreneurs like the CEO of Groupon were quoted as saying:

"DST is just cool..... I think they're disrupting the entire late-stage investment business. They are good at identifying exceptional companies and getting behind them in a way that entrepreneurs want them to. They don't get all caught up in terms. They are very accommodating." (Source: Business Insider, SAI)

In startups there is of course the phenomenon of high-school drop-out Andrey Ternovskiy, who rolled-out Chatroulette from the cramped confines of a Soviet-era apartment in the outskirts of Moscow after being inspired by the movie Deer Hunter! He is young and raw and not into the usual niceties. Word on the street is that Fred Wilson pulled some strings with immigration to get him over here with a special Visa. Milner too sent a limo to pick the kid up, but the lad wasn't impressed. I hear he's been making the rounds in Cali and is speaking at TechCrunch Disrupt this week. Something tells me this is one savvy kid and he's here to stay.

It also seems to me that much like so many of his erstwhile countrymen, he's having the time of his life playing this new game- and playing it his own way...

На здоровье!

Evening Tidings: 5-17-2010

Carleton: Senate Finally Comes to Senses and Amends Anti-Angel Nonsense

NY Times: VC the Old-Fashioned Way

Hecht: A Chess/Tech Story

Columbia Lang Fund: Board Select Four Companies For Funding

ChessVibes: Anand Discussed World Championship Triumph

CNN: Trouble Sleeping? Maybe It's Your iPad

Business Week: Steve Jobs Not Pleased with Gizmodo

Marketing Pilgrim: Larry Ellison Unloads on CEO Bloggers

Market Watch: Columbia Professor Joins Austin Ventures

Eisenberg: Nassim Taleb Calls Stock Market a Hoax

Morning Read: 5-12-2010

Venture Hype: Super Angel Ron Conway

Dixon: Old VC Firms Get Ready to be Disrupted

peHUB: Calacanis Calls Out "Young Zuck" Bay-Ridge Style

Calacanis: Calls out Facebook Some More

Weisen: Spring Office Hours at RRE  

WSJ: When it Comes to VC's Senator Jack Reed Can't Control Himself

Picasso: Don't Mess With This Man

Ehrenberg: Seeding A Startup Culture

Andor Arnoldovich Lilienthal, 1911-2010

Anand Beats Topalov for World Title

Entrepreneur Survival Guide: Motivation, Courtesy of Uncle Nikolai

This is part of my Series on Entrepreneurial Culture.

"I tattooed 'survive' on my hand the night before I went away to prison.
And I did. We do what we have to do to survive..."

Uncle Nikolai (25th Hour)

I've posted here about how to deal with massive and unexpected knockout-type punches as an entrepreneur. But there's another type of dangerous threat to an entrepreneur's well-being and survival:

It is the phenomenon of interminable waiting.

You see, entrepreneurs are always in perpetual motion, hurrying from one task to another, taking calls, having meetings, raising money, cajoling, selling, emailing, tweeting, blogging, hiring, partnering, selling some more, stressing, exhorting others, and so on and so forth. To the outside world it all seems like a dizzying whir of movement. Less visible is the fact that this is exactly how the entrepreneurial species waits. Waits? Waits for what exactly?

Think about it. You know what I'm talking about. It's that internal clock we have ticking inside that's coldly tracking the next milestone in our business amidst all the apparent chaos: private beta, first product release, first customers, first investor, Series A, hitting break-even, that big partnership, that first million in revenue, that first bad-ass hire, that first good piece of PR, that first big spike in traffic, and on and on. It never ends. We feed off of it- we live for it.

The problem is, most of these major milestones seem to take forever to materialize. There are always delays, endless obstacles, issues, difficulties, crises that delay our progress. We're fighting inertia, indifference, short attention spans and it's inevitable that moments arrive when our resolve, our will, our morale and in many cases our cash begin to melt away. That internal clock of ours so intent on progress gradually goes haywire and all this interminable waiting begins to cause despair. Thoughts of capitulation slowly creep into our minds...

How we handle and see our way through these moments define who we are as entrepreneurs and whether we survive or die.

That's why I recommend you rent and then watch a certain scene in 25th Hour several times. (Once my buddy Nate over at AnyClip posts it, I will link to it). It is the scene in which Uncle Nikolai describes to Ed Norton's character how he survived through his toughest moments in life. (Norton's character is facing seven long years in prison.)

Sometimes we entrepreneurs need some inspiration and encouragement and this scene will fire you up if you are out there now giving it your all- trying to survive. Let me know what you think.

Avoiding Typical Pitfalls with Founder's Equity

This is part of my Series on Entrepreneurial Culture.

In meeting after meeting with first-time entrepreneurs I see many variations upon the theme of what can charitably be called unfortunate decisions about equity splits between the early participants. It is of course always a relief when I'm able to catch the entrepreneur before he or she commits this typical sort of blunder. Sadly, all too often, it is already too late and there is hair on the deal.

If you are an entrepreneur launching a new company, you really have to think long and hard about who your co-founders should be and how to involve them. 

It is most likely the single-most important business decision you will ever make.

Here are some realities and rules of thumb to go by:

• Most poor decisions made in the allotment of founder's equity are made by first-time entrepreneurs in the atmosphere of euphoria created by 'taking the leap' and starting a company for the first time with so-called 'buddies'. If you are in this category- take heed!

• Blindly going in "50-50" with someone you don't know all that well is just ludicrous.

• In most cases you should only bring on one other co-founder, (at most a second), and that founder absolutely must offer singular value and expertise to the venture.

• If you do bring on a co-founder, make sure you put their equity on a vesting schedule. (Four year vesting with a one year cliff is standard).

• With this sort of vesting in place, if they end up taking off after a dispute or a change of heart, they don't end up leaving with a huge chunk of equity in your company! Your cap table thus will remain attractive to potential investors if you execute well.

• Only partner with co-founders that are as driven and passionate about making this successful as you are. Do not partner with people who enjoy just "hanging around the hoop". Remember, every founder must be totally committed to the venture.

For my video conversations with great entrepreneurs go to: Venture Studio

Morning Read: 5-3-2010

Horowitz: Why We Prefer Founding CEO's

Hargreaves: NYC Startup Drinks List

ReadWriteWeb: Mendeley Throws Open Doors to Academic Data

UPENN Almanac: UPENN Tech Transfer launches UPSTART

Kharif: A Russian Star Rises in Silicon Valley

NY Times: In New York, A Tech Incubator Becomes a Hub of Collaboration

Chronicle of Higher Ed: Tech Transfer's Big Moment

Calacanis: On GenY Loyalty