I got a great email from a reader in Europe in response to my The Demo post that said “Here in Europe we VCs refer to the practice of introducing portfolio companies as ‘Panda Mating’. It should work, there is a logical fit but somehow even if they do mate they very rarely conceive.”  Panda Mating is a great metaphor, although I generally have better success with partnerships between portfolio companies as long as they are more than a Barney deal.

I also got a question from another reader asking me to define “top down vs. bottom up” demo.  I much prefer “top down” demos – these are ones that approach the demo from a user / use case perspective.  Show me what the software does and why I care, not how it does it.  So, rather than start at the top left menu choice and go through each feature (usually starting with “creating a new account” which I never have to see again in my entire life), walk me through a use case that is relevant to me and is populated with a complete and interesting data set.  Occasionally, I’ll have a “how” type question, but then it’ll be in the context of a use case, rather than a technical feature.

I love working with Seth – he always challenges my brain.  If you are “paying attention” and want to hear a great rant on the last year and how Seth sees it, check out his post Spying on Transparency.

Several weeks ago, I brokered a meeting between two of my portfolio companies.  One of them is relatively mature, has a good sized customer base, and a great set of products.  The other one is very young, is a recent investment, has some great technology, but is just now bringing it to market.

The business synergy between the two companies is superb – they are both going after similar customers (they’ve already had a little overlap in their leads) and – for a segment of the market – have a comparable pricing and deployment model.

So – slam dunk, right?  Get everyone in a room, have them show each other their stuff, and figure out where to go together – especially if everyone in the room is smart, very clued in, and predisposed to partner.  I figured we’d walk out of there in 90 minutes with a clear plan of attack.  I made the introductions, sketched out an agenda (YoungCo demo for 15 minutes, MatureCo demo for 15 minutes, then let’s figure stuff out) and then let folks go at it.

YoungCo’s demo was lousy.  I’d seen the CEO pitch before and he usually does a great job, but for some reason he was off.  Rather than a top down demo that gave a clear view of the product, he gave a ponderous bottoms up demo (e.g. “now, I’ll create a new user account, log in, and show you a screen with no data on it.”)  It wandered, it rambled, and it took 45 minutes, and still didn’t get to show its stuff in a way that I thought MatureCo would light up on.

MatureCo’s demo wasn’t much better.  Same story – in this case, they have an awesome pitch, but for some reason the person giving it followed YoungCo’s lead and went bottoms up.  I was impatient at this point, so I jumped in more and tried to guide things around some, which probably didn’t help.

We finally got down to business 90 minutes into the meeting.  Since everyone in the room was smart, they were able to appropriately abstract what they were seeing and we finally got on a coherent track.  But – I wasn’t particularly proud of the first pass of either company.  We ended up in a happy place and they’ve got some stuff rolling together, but if I hadn’t been an investor in both companies, I can imagine a situation where neither would have had the patience to work through things to get to a partnering point with the other.

In hindsight, I realized this was ultimately my fault.  I assumed that both companies would be able to read my mind in advance of the meeting and I didn’t put the effort into framing things and setting the expectation in advance.  I usually do this – in this case I just punted because the fit between the two seemed so obvious to me.

However, if each company had started with a tight, top down demo, the entire tone would have been different.  I learned – early in my first company – that the first 15 minutes of a meeting will make it or break it.  I learned how to do a great demo – even if it was simply my sales pitch on a white board or flip chart.  This meeting reminded me how important it is for a young company (and a MatureCo) to be able to nail their demo and do it quickly.

Yesterday, I was on a conference call with an entrepreneur that I’ve backed in the past.  He wanted to walk me through the idea for a new business that he was working on.  His goal was simply to get feedback from me at the very early stage of his idea – he wasn’t pitching me for an investment.  We got about five minutes into the pitch when I interrupted him.

I’m an angel investor in a company that is addressing the same domain as him, uses similar language, and is going after a comparable problem.  I didn’t get far enough into things to know if there was a direct conflict, but I know that the company I’m an investor in is rapidly evolving their business from what their website says based on customer reactions – and the path they are on sounded very familiar to what I was hearing from my friend.

I raised a yellow flag, paused the conversation, and expressed my discomfort.  My friend knew the company, knew I was an investor, and explained that he thought they were a little different.  But – I wasn’t sure – especially given where I think the company is heading.  I was uncomfortable – and told my friend this – since I didn’t want him to pitch the idea to me in detail unless he was completely comfortable that all the ideas might already be being incorporated into this other business.  In addition, since he wasn’t looking for any particular outcome, I wanted to give him a final chance to back out of sharing his ideas with me at this point.

He concluded – rationally – that we should stop talking.  I felt better, and – while he didn’t get the benefit of my feedback – I don’t think he missed out on much since I expect it would have been an early / preliminary conversation anyway.  While he could have kept pushing me to listen, he knew what he wanted to accomplish (expose me to the idea and get feedback) and – since he had this in mind – realized that the benefit to him was likely lower than the potential cost if the companies were in fact competitive.

As a result, we had a pleasant 10 minute phone call, rather than a 60 minute phone call that – in the best case – would have likely been irrelevant for him.

I was in a meeting today in Redmond when someone mentioned something about Passport and Live ID.  It reminded me of something that happened a few weeks ago that I meant to write about, but forgot.

A few weeks ago, I was in a meeting at one of my portfolio companies using the CEO’s computer when I did something that caused a password request box to appear on some random website that I had surfed to.  I turned to the CEO and asked “what’s your password that everyone knows.” He laughed and said it out loud, which I then used to log in successfully to the random website.  I then turned to the person next to the CEO and said “What’s your password that everyone knows?”  He looked shocked and said “I don’t have one.”  I responded with “c’mon – of course you do.”  “Nope, he replied smugly.”  I then asked if his girlfriend knew any of his passwords.  His smug look disappeared – he had figured out which of his passwords everyone knew.

Do you have a password that everyone knows?  In our wonderful world of security, online identity, online storage, and hundreds of theoretically unique and secure systems that each of us use every week, do you ever wonder how secure you really are?

Ironically – the CEO’s password that everyone knows happens to be the same as the password of his previous business partner – that everyone knows.  Time to change a few passwords.

Amy and I love art – it is an integral part of our existence on this planet.  The Boulder art scene – while modest by New York standards – is vibrant and we love to participate in it whenever we can.  One of the major events of the year is the annual Art Auction at the Boulder Museum of Contemporary Art.  It’s happening this year on October 19th from 6:30pm – 10:30pm and Amy and I are the title sponsors.  If you like art, this is a great venue to see over 75 original pieces – many by local artists – have a fun time hanging out at a great party, and contribute to one of Boulder’s important local arts-related non-profit organizations.

On my Q3 Vacation, I read Anonymous Lawyer and loved it.  Jason – one of the lawyers in my life – just read it and had the following to say.

It’s a great read for anyone – non-lawyers included.  Jeremy blogged as a fictional hiring partner at a top law firm while still a student at Harvard and many people thought he was the real deal.  The book is one of the funniest books I have read in recent memory and is the perfect way to unwind at the end of the day or while traveling.  Please buy this book so Jeremy doesn’t have to go work at a law firm.

There’s nothing quite like taking a major spill an hour into a 90 minute trail run – in the mountains – alone – early in the morning.

At least it matches my shoes and my house.  I was going downhill – pretty fast – when all of a sudden I was falling forward for no discernible reason.  My knee took most of the impact (hence the torn pants and a cut the size of a silver dollar) – quickly followed by my forearms (yup – I’ve had a lot of practice falling when running.)  A 30 second system check later and I was back up on my feet.  I shook it off and continued on my way.

Kind of like the process of creating a company.

All serious runners know that ice has special properties and is a critical part of one’s recovery regimen (e.g. “Sore muscle?  Ice it.”)  However, I only recently discovered the magic of an ice bath.

Last month, immediately after running the Albuquerque Marathon, I went back to my hotel room (the bridal suite at the Hotel Albuquerque at Old Town – we asked for the “best room”) and immersed myself in a 10 minute ice bath.  Amy, Raj, and Stef  (my traveling marathon fan club – at least for this race) were in the other room watching the US Open (tennis, not golf) and were subjected to an outburst of “holy fucking shit” and 60 seconds of maniacal laughter as I got used to the temperature.  The last 9 minutes were fine, although I was disoriented and bemused when I got out of the tub.  I felt great the next day, although I forced myself to take a week off from running (every time I thought about running, Amy said “Brad – rest” using her best golden retriever command voice.)

On Saturday, I was in Bells, Texas at my parents farm for the weekend.  If you know me and my love of land, you’ll be able to trace it back to my parents farm, which they bought when I was in college.  There’s nothing like 100 acres that is yours to wander around on.

My dad got up at 6am, drove me 15 miles away from their house, and dropped me on the side of the road.  He drove back; I ran back.  I had a kick-ass run (a mile / minute faster than normal due to the lower altitude, plus I felt great.)  When I finished, I went upstairs, filled the bathtub with cold water, and dumped two huge bags of ice that my mom had bought at the gas station into the tub.  My outburst was even more colorful this time (“you’ve got to be fucking kidding me”) followed by peels of laughter as my body got used to the cold.  Again – I settled down – and this time hung out for 15 minutes in the tub reading 24: Trojan Horse.

Four hours later, I felt great and was ready to go for another run.  I managed to hold off until the following morning when I did a very comfortable hour run (at least for my legs), although I slept too late and ended up in 90+ degree heat.

I’m two for two with the ice bath, and am now a complete believer.