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

Start Up Choate NYC

Ivan Taback and Proskauer hosted the final at bat of our Start Up // Choate Spring Road trip in their gorgeous space at 11 Times Square. It was a fitting finale to a great week which gathered over 100 Choaties from three cities to network, learn, and share experiences about starting and growing businesses.

The Panel was definitely skewed young and mobile, with Alex Moazed and NT Etuk joining me for the final night. We polled the crowd and we surprised to learn that there were 10 entrepreneurs, 6 angels, 8 service developers among the crowd that gathered. All said, I’d estimate 2/3 of the crowds in all three cities were involved one way or another with start-ups in their everyday lives.

Who knew.

As usual, the panel had some great nuggets to share. Here we some of my favorites from NYC: When we talked about forming an ideal team and looking for co-founders, NT Etuk said “Don’t look for a partner in the mirror” – meaning having opposing points of view when developing a product, a business, and an organization is key. When we discussed “what would be the plastics for tomorrow”, Alex Moazed was sure that mobile was the answer for how profoundly is has affected our lives just five years into the show. He also added the analogy of the toy business, which never got around to thinking like a tech company: result is that toys (plastics, plush, etc) are now $20B industry, and digital games are about $18B. Gotcha.

Here were some of my favorites from Boston and San Fran:

One of my favorite comments from Boston was Bain Capital’s Jeff Schwartz (P’16) was embrace your ignorance. It can be a valuable tool. Dream about how to solve problems. Live in the future, and build what is missing.

Jeffrey Mullen (Founder and CEO, Dynamics, Inc.) who is a legit freak of nature (lawyer, EE degree, patent holder, CEO, addicted gamer, nice guy) was around the question of singularity (will we live forever if we live to 2046, per Ray Kurzweil). “Sure, I checked it out- living forever is basically an engineering problem”. And you know, he’s the one person that I believe probably has.

Michael Holthouse former CEO of Paranet (sold to Sprint) added that the “plastics” of tomorrow may well be energy. How we make it, store it, and consume it will become vital to our future sustainability.

My favorite comment of the San Fran night from Seth Sternberg was on the makeup of founder teams: While he stressed the fact that Eng’s (his abbreviation) had to form the core of the product and it’s build, having a business guy that does the deals/money was also a healthy add. One point we all agreed on: avoid replicants. Having divergent points of view are key. Last point form the audience was this: consider how “geared” your co-founders are to start a business. It’s a long haul, with plenty of dips.

And, proud to say, Choate finally started to get its social groove on: the  LinkedIn group (now one of the school’s most active) has been full of good pointers, suggestions, and comments and a twitter feed (at this point twitter’s most inactive account , but getting better ) picked up steam in New York (this is a relative term- it’s a humble beginning. Check us out at #startupchoate

Soup to nuts, this whole thing came togehter in less than six weeks from the time Ron Fleury and Joe McAndrew posed the question: “what the hell do we do?”. And while Choate has been effusive in its praise and gracious with its thanks during this whole process (and tireless in its coordination), I attribute my contribution to nothing more than “doin’ what come naturally”. Hard as this may seem to some, it is really, truly all in a days work. Special praise also to our hosts at Connect Solutions in San Fran and Choate Hall (coincidence) in Boston. So now Choaties with start ups, who have a great network anyways, now have one on mobile, social and local to press the advantage.

Which is perhaps the greatest start up lesson of all: do what you love and your efforts can make a tremendous impact.

DC in Bloom, early morning

The shots of DC mornings have been rolling in from friends this week with cherry blossoms in full bloom. Got me thinking.

I once had a great mentor in Washington DC who simply adored Johnny Walker Red. Pounded the stuff, well into his seventies and deep into the night. Though we were 50 years his junior, we tried to keep up while he showed us around the social scene of DC in the 80′s: big ballrooms full of taffeta gowns, art auctions with amazing numbers, crazy black gas guzzling limos. We made a lot of noise. Thankfully, he paid.

But, he had one rule: breakfast is at 8.

Now matter how late the night went, no matter how far we walked with Johnny Walker the night before, we all got to the breakfast table by 8, and to work by 9. He went off to practice as a partner in a very large law firm. We were in school. But the bargain stuck.

And so, I’ve gone on to my world of creating, building and leading start ups with some great co-founders over the years – most of them slightly younger than I. We often blend their urgency with my long range vision, their naturally updated thinking with my tried and true processes. Their tequila to my Burgundy. But somehow, it works, and often the work spills deep into the night. And the next night. And the next.  Much like those parties in Washington I remember so well. But every morning as the sun rises on our start up and every other throughout the country, we have to answer the bell. Make the great pitch. Push the next release. Counter the next punch from the marketplace. There simply is no room for sleeping in. No tolerance for being less than sharp when presenting or hosting at trade show or conference. No excuse for being late. Sorry, doesn’t work that way.

Yes, the late nights of my younger days marauding through the streets of NW Washington had some enduring value. But only because of that one hard truth: the bill is due in the morning. So do what you must to blow off steam. Enjoy yourself, often to the fullest. But never, ever let that effect how you perform the next day, or how others see your performance.

It wouldn’t be right.

(this was written well before 8 btw)

360 respect for Someone that looks up to you

I recently read “On Raising Boys” and it brought out some very interesting points that I think apply to start-ups as well. One of the three key phases to development for a boy is having mentors in his teen years that are outside their main family unit, that have perspective, and come with authority in some field.  He can rely on this guidance to make important decisions outside of his direct family unit while building interdependence and confidence on his own.

Same goes for mentoring entrepreneurs.

I recently wrote about my mantra of Discover. Develop. Deliver. Which in very broad terms means I am always looking for young-at-heart entrepreneurs with fresh ideas. But equally important is the willingness to develop themselves  their product, the message, etc.

So here are some experiences I have drawn from mentoring lots of entrepreneurs over the years:

Know what you are mentoring to

Sounds crazy, but often the mentee does not know what they want out of the relationship. “Sounding board” is often the catchword for “ I need someone to talk to”. Rather than that generalization, I find I have always been more effective when we focus on a specialty need. It could be finances, business models, business development, partners, motivation, time management, you name it. But knowing what the mentee wants out of the relationship allows me to think on their behalf through the lens that they asked for guidance.

I don’t give personal advice when business advice is asked for- or vice versa.

I try to share my experience wherever possible. I tried this… I realized this…. I once had trouble with this… so that the entrepreneur can see things through another lens, and not be defensive about hearing “you should do this.. try this… break that. Entrepreneurs are tense enough; they don’t need an office parent telling them to eat their vegetables. I was reminded recently of one of my classics in this category: breakfast begins at 8. I work with so many younger entrepreneurs, who has a quite different idea of “bedtime” on “school-nights”. Rather than try to correct that behavior, I simply scheduled important meetings at 8am. They soon got the message that no matter what is done the night before, the bill is due in the morning. Here’s the link from Richard Dinan ‏ breakfast is at 8

And I try to help people discover the talents within themselves by asking questions. Lots of questions. Lots and lots of questions. Eventually, we run the table from vision to execution and are ready to make some bold decisions. Having what Covey called “the courage of our convictions” means all the available facts have been surfaced, and intelligent discussion held, and the best course chosen. It’s never a lock, but it sure helps to enter the rapids with some sort of thought out plan.

And, most importantly, I try to behave like someone whose opinion is often sought. That’s perhaps the most important lesson of all.

Work with a mentee that actually is coachable

Some mentees want window dressing: so-and-so is on my Advisory Board. Some want a sounding board, but have their minds made up anyways. Some are just lonely. To me, neither are a great use of mentor time.

The mentee that has a thirst to learn, a gift for presenting situations with options, a curiosity to experiment and learn gives the mentor a sense of usefulness that is so key. Good mentees have the elements of challenges or opportunities worked out in their minds, but often lack the confidence to make a decision or fear some blind spot they haven’t considered. Those are great examples of where mentoring can really help cut to the chase, or save some dead ends.

The biggest gift you can give someone is to beleive in themselves – AJ Joshi

If you are doing it to make everyone money, let everyone know. If you are doing it for charity, make sure it’s worth it.

 Ah yes, why do we do this. Mentors are rarely ever paid by the hour (though some coaches are, but I contend that is different). I mentor a lot of CEO’s and Founders where I own stock in the company and have quite a vested interest in their success. So by teaching them, I expect to add value to my position. Sometimes, the lessons actually shrink value in the short-term; but that’s why they are called lessons. The worst sin there is to repeat them. Good way to lose a mentor relationship.

But some mentor relationships are just plain charitable. While I have very little free time to take on non-commercial mentorships, sometimes I run across someone who I really believe in, and believe they could use my help. I guess the key point there is that both mentor and mentee know what the other is doing it for, and the ground rules are set and respected.

I’ve been told that time spent and value delivered does not necessarily correlate: you can do just about anything in two minutes… if you spent thirty years perfecting how to do it.

Gate is actually the basis of the Vaux Logo

Despite focusing most of my writing efforts on my blog, and keeping up with the world via my twitter the year-end letter to Vaux angels is a tradition well worth continuing. I’ve cribbed the best of it here…

 Discover. Develop. Deliver.

These three words are scrawled across everything I do for Vaux. They are three parts of my personal mission to success as entrepreneur and angel investor, which I had the honor of mapping out in a 2012 white paper for the Family Office Association  “Angel Investing for the Family Office” . I took a hard look at the process of building a foundation on the long journey from inception to exit, and nowadays I plan my week based on these categories. I color code each meeting in my outlook. They might as well be scrawled on my bathroom mirror in lipstick. They are the cycle of life for Vaux les Ventures and the angels that have supported these endeavors for nearly 10 years. Here’s what these simple words mean to me:

Discover is about being very focused on what you can do well, and what markets will have an impact that can generate angel returns. Big market trends that people don’t yet see, or are unwilling to accept. Trends that will obviously converge, but no one knows exactly when. It means being early and brave, but it also means being patient to find the right mix that can sustain the long march. This is where the DNA of the business is set: habits formed early are virtually impossible to break. Many people in the business call this “deal flow”, and I did too for a while but I soured on the term as too many IB ‘s and VC’s (both of which I have been) over-use it. Having a well know criteria for how to invest and who to invest with seems to do very well in attracting the right types of people. So does being a good guy. But it’s about discovery as much as it is about network. And that discovery includes markets and their real problems as well as solutions and the best team to build them.

A recent example of this would be my work on WellAware, the mobile health solution. I’m as committed as ever to the trend of mobile devices having profound affect on health and wellness. And I truly believe that very simple data can have tremendous impact on lives. The Wellaware team did a tremendous job developing the platform for this theory to play out, but certainly overshot the MVP standard. What we need in 2013 is more cycles with large user bases to refine our solution, likely in the mobile environment.

Develop is where the entrepreneur (in anyone!) takes over: translating a vision for a product solution into a product itself, and testing it with users to see if the darn thing works. It takes tremendous amounts of courage, persistence and luck. Some attempts are ridiculously off the mark. Ironically, more often there are overshots than undershots when going for the minimally viable product. And users are rarely the viral dream everyone hopes for- more like a block-by-block struggle to get to a vantage point where people notice you. But more than product and users, the team is the big part of the develop picture. Entrepreneurs have a passion for building things are not always Schwartkoffs when it comes to leading people. And that is where the coaching and mentoring foundation is laid. Capital begins to show up at this point, as we have baked enough of the risk out of the opportunity for larger sources of capital to begin to show interest. That too is a major challenge in this phase, and if you grow fast enough, it never ends.

[Major edits here from the angel letter. Sorry, that's not public.]

The poster child for the develop phase is certainly TrustCloud, which just 9 months ago had product solution in search of a problem, no user base, and a team that had already endured a few pivots. Such are the risks of being early! But the saving grace was each of the founders used the sharing economy and saw what it could deliver, as well as its limitations. Something had to give, we thought.

And 2012 was full of such breaks, as TrustCloud found its core team, delivered a product and began building users at an impressive clip  (10x from July to December) after the Wall Street Journal picked us up. Check out the product here, or the very impressive Facebook TrustCloud user group (which tracks bugs and promotes the product passionately). The Company rolls into the New Year with a new Peer Protect insurance product to couple with it’s ever growing number of sharing networks.  Kudos to the indefatigable and imminently coachable CEO Xin Chung, who details the year here:

 I shared keys to my NYC apartment on Airbnb, rides through San Francisco in a Sidecar, and my workload with TaskRabbits. I’m not alone– people worldwide are sharing more than ever with millions of room-nights booked, cars rented, and dogs walked by reputable strangers. The movement is called The Sharing Economy, Collaborative Consumption, or as Mary Meeker calls it, living Asset Light. (this is a great read! Don’t miss it!)

 Flush with VC funding, the movement scaled fast in 2012– but not without growing pains: A quick look at recent sharing history would give anyone pause before sharing with a stranger. Home sharing market leader Airbnb had a redux of its 2011 EJ incident with the so-called airbed & brothel snafu where a Swedish apartment was literally pimped-out. Carsharing had it’s own collisions with the luxury carsharing service HiGear shutting down due to thefts, car sharer RelayRides’ liability issues with a fatality crash, and regulatory fines for on-demand ride-sharers.

 These events highlighted that trust between strangers in peer-to-peer marketplaces must keep pace with their own rapid growth. In the offline world, hotels have long adopted star ratings, rental cars are licensed and insured by brands spend billions to give consumers confidence to buy. Since online, peer to-peer marketplaces powered by micro-entrepreneurs don’t have time to brand themselves or vet strangers, they are much less efficient as buyers and sellers waste time sizing each other up, figuring out a schedule and even haggling over price before committing. Trust can make these transactions much faster, and insuring the risk is something we look forward to. Read more at TrustCloud’s Blog.

Deliver is where all the hard work pays off. That would seem like a triumphant moment, and I’ll allow myself a few. But as I have matured it has become a little more bittersweet. Here are companies we have built from scratch, communities that started with a handful of people, angel capital that came in for under $1M pre money. And despite some intermittent liquidity opportunities, in some cases these companies have futures that remain bright(er). We have seen large that we turned down; we may see 2x-3x-4x from here (or of course, we may not). So parting with some or all of the ownership isn’t as easy as “see ya later”. It’s an asset, with a value that has to be managed detachment that is at arms’ length, hard as that may be. We also live in a world of high risk, so those precious few windows of liquidity opportunity have to be considered when they are open.

[More major edits here from the angel letter. Sorry, that's not public.]

In summary, I guess I feel every venture I have been involved with has contributed to the next. Things I have learned about the Discover phase have allowed for better Develop results. Those few short peeks at liquidity in Deliver have been viewed with a paradigm that allows the whole group to consider individualized risk and reward before deciding on liquidity. And of course, the success through the process has allowed us the opportunity to feed the beast, return to what we do best, and further diversify with another opportunity.

I am extremely grateful for the opportunity to work in the field that I do, side by side with talented entrepreneurs, backed by caring and value adding angels that ask good questions and have the patience to help realize the vision I had almost ten years ago. We’ll see great opportunities in each of the three key Phases in 2013. Drop me a line and we’ll discuss which ones best fit your criteria in the days ahead.

All my best in the New Year,

Ridiculously happy, no ticket required

Least it feels like it, every day.

No ticket required. No waiting in line either.

And no sense of outrage that followed… the last guys from Greenwich who won.

No ignorance tax, for those that don’t realize it’s all just states… generating revenue.

Yes, that’s a short post, but certainly, one of my better.

What did you win today?

Twinkies

Only in America would people violently trample each other for discounts, exactly one day after being thankful for what they already have.

Consumption of calories.

The Twinkee headline this week got me thinking about, with all our bounty we are unable, unwilling or incapable of  governing our intake.  Look, 150 calories of processed corn syrup won’t kill anyone in one sitting. But who in America eats one? And who does it just once. This food group has been a best seller in America for a generation. Later in the week, another caloric orgy takes place; It’s hard to believe, perhaps, that the average American Thanksgiving meal equals 3,000 Calories That would mean a 160 lb. person would have to run at a moderate pace for four hours, swim for five hours or walk 30 miles to burn off a 3,000-calorie Thanksgiving Day meal. Most do not.  Trying to work that off with the halftime football toss is as futile as try to get warmth from the slanting sun as the ball flies through a deep winter sky.

Consumption of natural resources.

How much gasoline does the United States consume? 1.18 gallons per person per day, every day. This figure includes every man women and child, (only 89% have licences, and about half of them in my neighborhood deserve to be retested regularly). 33 Gallons a month, enough to drive a little less than 1,000 miles on any of our great highways for the princely sum of about $4.00 per gallon. In France, that would run you about $10.00 per gallon, which is a) realistic , b) forces conservation, c) reduces the number of escalades tooling around in Paris. Add that to the amount of plastic we consume (another pertro-product) and you have the makings of a genuine addiction.

Consumption of Media.

The one that bothers me the most, and demonstrates the worst lack of self control is couch potato TV time: 2.5 to 2.9 hours per day. Worse as you get older. I’m not sure if this accounts for time spent on other screens like tablets and phones. I doubt it, and I will concede that at least most of that screen time is spent learning, communicating and socializing (in a mild form). But almost 3 hours per day in front of  the TV tells me people need something better to do.

So, the point is this: if even the French can point it out (and do so with empathy) it must be pretty obvious. If we can spend a little more time being thankful for what we have, consuming in more reasonable proportions, and buying and wasting a little less of what we don’t really need… we’ll be a little better off.

Giving up Twinkees is a good start.