Miles To Go.

Xin’s Thoughtful Gift: PBJ and Ramen 2

Being an entrepreneur is a lumpy business at best. And while I’ve written extensively about the mortality rate (95%), I’ve never written about how hard it is along the way for those 5% destined for greatness.

It ain’t easy, and it ain’t easy on everyone.

This is a basket of Ramen Noodles and Peanut Butter, presented on my Birthday by a very appropriate, thoughtful entrepreneur I backed; Xin Chung. Xin certainly has the moral authority to present the gift: he was liberated from Saigon as a child, spent time in an internment camp, and grew up in Valdez Alaska before settling in to SoCal and pursuing his dreams as an entrepreneur. He is now Founder and CEO of TrustCloud which has emerged from a “walk in the wilderness” with 10k passionate users and a growing number of interested clients in the social check space.

The Ramen and PBJ is our shorthand for being capital efficient, a must for start-ups.

My system at Vaux usually provides $250k of less for a team to develop a product that addresses a meaningful market problem, and do it within 90 days or so. This means most for the proceeds are dedicated to product. The next $250k usually goes to determining if anyone cares. The numbers vary, but either way the Founders and early employees do not get rich in salaries off of angel money. Frankly, they have to be prepared to barely eat, and when they do eat for strength. This is part of the ugly underbelly – and not a full underbelly! – of the dedication it takes to pursue your dreams. Every dollar you don’t waste can go to a better product or a better viral coefficient.

And of course, stuff takes longer than you expect. And costs more money than planned. This puts tons of pressure on the entrepreneurs as they debate the next crucial steps, often on an empty stomach. Probably once in my last 10 start-ups has a company got it right, right out of the box and kept doubling down all the way. Most try with a product, revamp, try again, tweak, and try again until there’s no track left. And it leads to some very difficult conversations about where to invest precious resources: make the product better and more people will come… or tell more people about the product and they will spread the word. Development vs. Marketing vs. Biz Dev. It often provokes difficult conversations, and sometimes desperate measures (these guys slept in a van on a Biz Dev road trip that lasted months).

And so the entrepreneurs themselves, while pursuing their dreams of autonomy, making a mark on the universe and yes winning riches, have to absorb the vagaries of what precious resources to assign where… including their own sustenance. I get queasy when I hear comparisons to the comp someone could make in the corporate world, which simply doesn’t apply in start-up-ville. And I get nauseous when I hear debates about how deep down the rabbit hole start-ups should go pursuing the next pivot (which is another term for fail and try again). Luckily  angels don’t have that much patience or that much capital for endless restarts. Which is why, when interviewing prospective partners I always look for that unique combination of resourcefulness, willingness and mental toughness that will see us through. And a dose of reality to know when to put a fork in it.

Entrepreneurship is not a straight line to the summit, it’s a jagged ascent and we have to be prepared for the whole ascent not just the sprint at the top.

~~

Save runway: TrustCloud’s sample T&E guidelines

Use personal credit card; expense every month with invoice. Avg trip: 2nts/3days, $800, $1000max

1. Air: economy $250

2. Ground:  $25/day

3. Lodging: Airbnb $50/nt

4. Entertainment: $75/day

5. Badges: pre-approved

6. Big dinners: pre-approved

Mobile Global: Click 2 see cool pic

I work hard to get lucky.

1. The Carriers used to think they were content curators. Seriously, there was no other way to get distribution than to program in bizarre carrier languages (BREW, etc) and pay them through the nose to be “on deck”. Hey, they got the idea from the old AOL days. But these people did not realize the comic effect of managing content on a 2″x2″ screen. Plenty of money was wasted getting on those decks, and getting the content optimized. At one point, I counted an easy $500MM of venture money was poured down that rabbit hole.
2. Eyeballs began to shift. First it was getting email and text on phones. Then a few games and stock quotes. But the iPhone and its 250,000 apps out the gate brought all manner of information and entertainment to the mobile screen. The PC reached a plateau.
3. People were no more willing to pay for apps than they were to pay for the “old fashioned” internet. It should be free, man continued as the digital credo. And except for very few exceptions (iTunes being one), the entire mobile revolution has been driven to date with ads.
4. Tablets followed shortly, and guess what: they’re mobile too. Meaning all the ad serving technology, all the geo-location and device data was much more like a mobile phone than a PC.

With a little knowledge as an angel/board member with digital yield optimizer operative (now Operative One) and some domain expertise from Cellufun, I went on to start mobile ad network/ad server Mojiva with co-founders Krish and Dan.  And I have since been founding angel in mobile powered projects like MyBailiwick (crowdsourcing too early!), TrustCloud (trust in the sharing economy getting hotter now) and WellAware (mobile health and wellness platform). I think my bets in mobile media have been pretty lucky, and i will continue to make them for all the basic reasons above (and many more that are regularly laid out by tech guru Mary Meeker).

I just never knew where the tipping point was.

I do now. High five.

Michael Arrington is blunt.

That ouchie brought to you by Michael Arrington at a recent Tech Crunch Disrupt Conference.

It’s not as bad as it seems.

I find myself initially defensive at this comment, made by the headline grabbing (headline making!) founder of TechCrunch. I fall on the other side of thirty. If you check out this graph, which represents 300 responses from startups financed by Ron Conway, repeat founders under the age of 30 get more $500M+ exits. 

So if this is true, are old(er) founders more cautious, prudent, and take earlier, cheaper exits for security? Possibly. Whereas a younger founder will let their company brew for a while, gaining value, or be more tolerant of the risk along the way.

Older founders have also likely seen the game played before, and know how to judge incremental success, while a younger buck is more likely to bet the farm. But what is most interesting to me is which of these personalities match best with todays “2 & 20″ VC dynamic, where small hits don’t clear their preference hurdles. If you need a moonshot to make a buck for your portfolio, by all means go find a kid.

But they are getting less naive every day.

Huana AKA Sugar loaf

I was in Deer Valley recently for a Pelion LP meeting and the topic turned to high- altitude climbing. Entrepreneurs that I work with know that I constantly use the experience as an analogly for building companies. (I have analogies for everything, some more crazy than others.  At least, that’s what I’m told).

The basic premise is that, as you get to higher  altitudes, your mind and body play tricks on you. Cognitive powers are altered. Moving carefully and deliberately is important, but so is having a guide to help you move quicker and avoid mis-steps. For a look into real-world mountain climbs, there’s a great book called Into Thin Air by Krakuer that covers it well. (and the rebuttal by Anatoly Bukareev is just as good). As for entrepreneurship, there are very few books about a company’s pending danger and death; most focus on reaching the top. I wrote a bit about that aspect in a prior post called Let ‘em Crash. I personally have been to what I define as” high altitude,” both in climbing and entrepreneurship. (Over 10,000 and over $100M+ in valuation, respectively.) Here’s a hairy story from one climb: entrepreneurs, see if you can pick out the analogie(s).

A trip to Peru brought me to the Machu Picchu lodge and my altitude adjustment was fully set, having begun the trip in Cusco at 11,000 feet. I had climbed Huana Picchu earlier that day, at dawn. I saw the most spectacular sunrise, as many Inca priests had before me (hint, these would be VC’s), and marveled at the symmetry of the Sun Gate and the other temples in the complex. I returned to the lodge for late breakfast. It was there we began talking about Cerro, the peak I had seen obscured by mist from Huana, with a giant flag fluttering at the top. I did some quick calculations and decided I could make it by sundown.

Cerro is the highest immediate peak above Macchu Pichu, but there’s nothing technical about it.  Like most of the Inca trail, .ost of the path is carved rock.  A little slippery at times, and occasionally requiring pull-ups, but mostly the climb is a mental one. I say this because the Urabumba River roars on three sides of the peak, and the drop is about 1,000m, sometimes straight.  After a few thousand feet, the mist socked me in. All there was in front of me were stones, laid by Incas many hundreds of years ago, and vines. And the sound of the river. It became my navigation.  As I heard it down and to my left, I knew I was on the west face; at it switched to my right, I knew I the path had traversed to the west. Half way up, I met two Japanese who were on descent. You alone?, they asked. Yup. Even that small exchange heartened me, not for the guidance, but for the fact someone else would know where I was on the mountain if things got bad. As it was, their estimate was a bit off.

 Ninety minutes later, I came through a skree field of snakestone (awesome green stuff that looks like malachite, but softer) and arrived at a gate of carved rock. It was the first clue I was entering a holy place. From there, I experienced my closest-to-divine moment. The path became flat, and the mist enveloped my feet, such that only my footfall revealed the path in front of me. I was on the spine of the peak, so the sun, or what was left of it, made the way brighter. I noticed orchids, which grow wild at that altitude. And hummingbirds which fluttered around like some  Natural History Museum display. Summit euphoria was taking over, as I heard the flag flapping in the wind in front of me. As I reached it I sat still for twenty minutes, precious time given the daylight. It was total peace. (Have you guessed? This is an exit!) 

When I turned to go, I notice the river roaring about me not on my left or right, but on three sides. With the dimming sun, the mist, the flowers and birds it was truly heaven. The euphoria lasts through the first fifteen minutes of descent, as I passed markings I had made in my mind during the ascent. I allowed myself to gain momentum, feeling free, and frankly as good as a teenager in springtime. Then I mis-stepped. In an instant, I was hurtling down one side of the face, when I instinctively grabbed on of the vines hanging from the face. It caught me, and I quickly recovered, with not a small amount of briars — and a pulse suddenly 2x. I kept rolling, and reached the main Inca village by dusk.

Llamas get around without Merrils

At dinner that night back in Macchu Pichu, one of our guides, Juan —- asked if I had walked or crawled on the spine of Cerro. I told him, and he was surprised. Most people crawl, he said. The spine is only 2m wide, and the drop to the river there is about 800m on the right side, and 1,200m (4,000 feet) on the left. Well, I walked the whole thing… maybe leaning a bit to the right to compensate for the difference…

But the most interesting thing about that climb was what it taught me about the entrepreneurial climb: the height of the ascent is an optional objective… but the return is mandatory!

» Monastario-Cusco
» Machu Pichu Lodge
 and ask for  Juan and Lourdes Sotomayor

VCs... deserve some respect!

As the summer intern wave hits New York, I get my share of inquiries from very smart kids wanting to become VC’s.

And now I know, as Rodney Dangerfield once said, why tigers sometimes eat their young!

It’s that tough a world. Yes, I’ll be the first to tip my hat to some great VC successes (not much ink is wasted on the failures), and it makes a wonderful pickup line for Wedding Crashers.  But being a VC today- or tomorrow- is way harder than it looks. First-time funds, no matter how much they raise, are basically start-ups under intense pressure to provide a preferred return to their investors before they get paid anything special. They have to be incredible consensus-builders within their firm  to get anything approved. And the deals that everyone wants come with incredible competition from everyone else looking at the same thing.  This is not a profession to wander into with stars in your eyes. If you do, expect your Share of Crashes.

According to a recent Cambridge Associates Study, short-term returns in 2010 were fine (based on data from nearly 1,300 funds raised between 1981 and 2010, U.S. venture capital rose from 6.4% at the end of Q2 2010 to 8.2% by the end of Q3 2010,). But venture is a long-term asset class. The median net return to VC fund investors has not been positive for any vintage year since 1998. Cambridge reports that 10-year returns fell from a miserable -4.2% to a downright horrid -4.64% over the relevant period. Five-year returns fell from 4.3% to 4.25%. Think about that for a moment: despite the past decade’s many hits (Google, YouTube, etc.), the typical VC fund has lost money for its limited partners. Even the top-quartile benchmarks over the past decade aren’t very impressive, with the best figure coming in at 5.59% for 2001 vintage funds.

I was a VC for a brief moment in time and it was fun, profitable — and nothing I would ever attempt to repeat.  From 1997 to 2000, Capital Express, having failed to raise any big money like our competitors in the dot.com chase, had a measly $4M to invest. But we picked right (including an IPO that reached a $4 Billion valuation for a moment) and we exited with great timing, returning 100x. It was the top of the bubble. My partners were fantastic, our timing was fortuitous, but I know the difference between luck and skill, and believe me, as good as we thought we were, we were luckier than we will ever know.

Do not try this at home! Your results may vary depending on many circumstances. The mortality rate of VC’s and their funds is stunning.  Thats why I now leave that work to smarter people, and wish them all the best. And I do that often because I see them practically everyday: in the past five years,Vaux’s companies like Cellufun, Operative, Mojiva and more have raised nearly $50M in capital from VCs.  I  sit on panels with them, across board tables from them, and see them constantly in subsequent fund raises for growing companies. They’re incredibly smart, ask great questions, usually have relevant and helpful operating experience, and work really hard. Yet, their fate lies with the luck and timing of a random world.

Is that a profession I would encourage a little cub to venture into? I respect VC’s, I just don’t encourage more of them.

And if they absolutely insist, I wish them all the luck.