In May I made a request for images for a presentation I was doing at my 20th MIT Sloan School reunion.  The presentation – titled Software Innovation — Do You Think the Last 20 Years Were Exciting? The Next 20 Years Will Blow Your Mind is now up on the web.  If you don’t want to watch it, read the summary below:

In a trip down memory lane, Brad Feld regales us with the pre- and recent history of electronic innovation, with a rapid-fire delivery that achieves vaudevillian pitch.

Via a slide-laden PowerPoint presentation — and, by the way, Feld claims to hate PowerPoint, because as a venture capitalist “I’ve only received about 6,723,000 of them” — he narrates landmark moments in the evolution of the computer age. He touches on the room-size ENIAC computer, and pays tribute to the Jetsons cartoon as embodying his view of the future as a child. He cites his first programming language (APL, 1976), and first computer (Apple II, 1978). Feld speaks sentimentally of the familiar A> prompt as a quaint relic of the DOS operating system era.

Jump to the late ’80s, when Hypercard on the Macintosh was a pre-web foreshadowing of distributing data through multiple applications…“a major breakthrough.” Windows 3.0 heralded the ’90s and subsequent leapfrogging of Microsoft and Apple on the personal computer frontier. He cites the renegade Linux operating system (1991), then the ignoble Michelangelo virus (1992)…“the first time the mainstream media got crazy about computer security.”

Feld detours from history to recount naming his software consulting firm Feld Technologies; whenever anything went wrong “people called up and asked for Mr. Feld.” Therefore, he warns “lesson #1 of entrepreneurship is don’t name your company after yourself.”

In the mid-’90s, the emergence of the Internet in mass culture made ubiquitous such terms as Mosaic, Yahoo!, Java, Explorer, and other iterations of web browser, search engine, and email protocol. In 1999, E-commerce and the Y2K scare entered common parlance. Around 2000, OS X and iTunes burst on the scene, in spite of post-Internet bubble depression. Feld credits Apple with changing “the way we think about digital content.” Catching up to recent times, he invokes social networking, the astronomical Google IPO, and the notion of Web 2.0.

As a venture capitalist, Feld seeks new paradigms in software development as investing prospects for 10 to 20 years – “the next big thing.” He is interested in “immersive experience” that alters human interaction with the computer. His attention is also drawn to decoupling mouse and keyboard from control of the computer toward methods requiring no tactile input. Lastly, he speaks of “cloud computing” where “everything is disconnected from what is on your desktop” and “you don’t have to worry about…data storage and equipment.” Then, elliptically, he reprises a slide of a 1960s room-size computer, suggesting it resembles a latter-day incarnation of a server farm. Full circle.

As a special bonus, the speaker who preceded me – Professor Roberto Rigobon – did an incredible job on his lecture The U.S. and the World’s Recession which feels particularly relevant and prescient today.

Once a year I go on a long weekend trip with the men in my family (my dad, his brother, my brother, and my two cousins.) We hang out, see a baseball game, eat, talk about our lives, and discuss the future.

This year we went to New York City. My dad and his brother grew up in the Bronx and we decided to see one of the last Yankee games at the old Yankee Stadium. Before the game, we spent three hours touring the Bronx where my dad and his brother grew up. I don’t remember the Bronx at all; my world view of it was shaped by a combination of my dad reminiscing about his childhood in the Bronx in the 1940’s and 1950’s and Tom Wolfe describing the bombed out Bronx of the 1970’s and 1980’s in The Bonfire of the Vanities.

As we drove around the Bronx, we talked about the natural cycle of life from birth to death. Against the backdrop of their childhood, we talked about the current economic cycle in the United States and the chaos we were seeing in the financial markets.  We talked about the growth of China and India, especially in the technology business where most of us are involved. We talked about what makes people, companies, and countries great, and what happens when they stop being great. At some point my uncle tossed out the line of the weekend – “If You Aren’t Growing, You’re Dying.”

We kicked around the idea of growth for a while over dinner. When we talked about growth with regard to people, we didn’t just mean physical size. When we talked about companies, we didn’t really mean only growing headcount or revenues, but included skills, experiences, product lines, and geography. When we mapped this idea to a country, we included economic expansion, job creation, company creation, and innovation.

As a long time entrepreneur and venture capitalist, I have strong opinions about the critical importance of innovation to society. To me, growth is all about experiences. As an entrepreneur, you learn from every success, but I think you learn even more from your failures. Since it’s both socially and legally acceptable in the United States to fail, some of the best entrepreneurial successes come immediately after entrepreneurial failures. It’s one of the pieces of the equation that I think makes the United States so great at innovation.

The world we live in today is much more complex than the world my dad and his uncle grew up in. Yankee Stadium was the center of their universe. TV was a new idea. The computers and the Internet we use every day had not yet been invented. Entrepreneurship existed, but it wasn’t the mainstream.

As we drove around the Bronx, we were all amazed by the incredible amount of growth we’d experienced. We decided that much of it had come from the endless efforts of entrepreneurs. Some resulted in success while some resulted in failure; all of it contributed to growth.

We concluded that every entrepreneur has an opportunity to grow, to create new businesses, new jobs, new industries, and change the way we think about things. In fact, I think that if you are an entrepreneurs, part of your responsibility is to do everything you know how to do to grow.

Or else you are dying.

Recently, I’ve found myself in several situations where I realized the complexity of each one had spun out of control.  Rather than be able to make a rational assessment of the situation, collect a set of specific data, and make a decision I found myself in a discussion that was going around in circles.

When I was a kid, my dad used to refer to these situations as "complicated mistakes."  You’d make a mistake and, in an effort to deal with it, you’d pile another mistake on top of it.  Before you knew it, you had a complicated mistake which was much harder to deal with.

I’ve worked hard in my life to understand what a "sunk cost" was an how best to deal with one.  While I’m not perfect, I’m pretty good at assessing the situation and removing the notion of the sunk cost from my going forward analysis.

When you have difficulty understanding how to deal with a sunk cost and you get tangled up in a complicated mistake, a real mess occurs.  You keep trying to fix the complicated mistake and justify the ongoing future investment of time, energy, and money based on what is essentially a sunk cost that you are unlikely to recover.  Rather than valuing your sunk cost at zero and simply evaluating the future potential of the opportunity, you compound the complicated mistake even further.

My solution to these situations is to simplify. Completely write off the sunk cost.  Ignore (or void) as many of the historical decisions that created the complicated mistake.  Figure out what your real current reality is and what you want your future state to be.  Then create a plan that connects your current reality to your desired future state.

Start by simplifying things.

Anyone who has worked with me knows that one of my favorite lines is "marketing is stupid."  And – if you really know me – you know that I don’t actually mean "marketing is stupid", but I use it as a proxy for "most PR people suck, most marcom is done poorly, and most companies have no idea what they are trying to accomplish with all the money they waste on shitty marketing and PR."

Last week I got one of Jason Calacanis’ email missives from his new email list (post-blog).  It’s been reblogged on the Silicon Alley Insider blog titled Jason Calacanis On How To Get PR For Your Startup: Fire Your PR Company.  There are a few things I disagree with, but on the whole it’s one of the best long essays I’ve ever read on how to do PR for your startup.

While there are a few technology PR firms (or more specifically – people) that are just awesome and worth the money, the vast majority range from marginally useful but not worth the money to completely useless.  If you are the CEO of a startup, I encourage you to read Jason’s post slowly, and then re-read it, and then think about what you are doing to get PR for your company.

Jason and I were talking about some of the running events in the Olympics as we walked in to the office together this morning.  After chatting about the marathon, he asked if I’d seen the Bolt 100 meter final.  I did – and it was an amazing performance – but I was perplexed why Bolt coasted the last 20 meters and "only" did 9.69 when he most likely could have broken 9.60.  Now – 9.69 is a world record, but 9.60 (or even the symbolic 9.59) would be mindblowing.

Jason suggested that it might be marketing.  Whoever is "advising" Bolt said "just win and break the world record by a little.  Then the endorsements will flow.  Then you can keep breaking the world record and steadily upping the stakes."  Cynical, but it rang true.

This just in – Bolt won the 200 meter and set a world record – 19.30.  This time he ran hard through the finish.

Now – I think both Bolt and Phelps are incredible athletes.  Amazing.  Mindblowing.  But I was really baffled to see Bolt pull up short.  It made no sense to me, especially when compared to the incredible effort by Phelps across all of his races. 

This made me think of sales people or teams that beat their number in a quarter and then bank something for the next quarter.  I’ve never ever liked this practice, especially in private companies.  I much prefer the Phelps approach – where you give it your all through the very end and bring in as much as you can, take a deep breath, and start all over again – than the Bolt approach (at least in the 100) of when you know you have it nailed, you coast to the finish.

Alex Muse has a long, detailed post up about How [He] lost $20,000,000+ in 18 months.  It’s the story of his experience with LayerOne – the first version and the second version.  It’s a useful story on failure that harkens back to 2001 with a nice redemption twist at the end.

Mark Cuban has a brilliant post up titled How to Jumpstart the Economy – Tax Free Small Businesses.  He totally nails it.  Send a copy to every politician you know.

My friend Larry Nelson who with his wife Pat runs w3w3.com interviews me periodically.  I’m always happy to talk to Larry – he’s a tireless reporter on the Colorado entrepreneurial scene.  His most recent interview with me happens while I am reclining on my red coach downstairs in my house in Homer, Alaska.

Note the blue sky in the background.  It’s gone now, but it was here for a few days.

It’s unusual for a founder to write a long thoughtful post on the failure of his company.  Roger Ehrenberg – the co-founder of Monitor110 – which shut down earlier this week, did just that on his outstanding post titled Monitor110: A Post Mortem.  The post is oriented around Roger’s "seven deadly sins":

1. The lack of a single, "the buck stops here" leader until too late in the game
2. No separation between the technology organization and the product organization
3. Too much PR, too early
4. Too much money
5. Not close enough to the customer
6. Slow to adapt to market reality
7. Disagreement on strategy both within the Company and with the Board

Every person in every company that I’m involved with should read this post carefully.  Every entrepreneur should also.  Failure is part of the entrepreneur experience – Roger has done us all a great service by being willing to be deeply introspective and share his thoughts on what went wrong at Monitor110 in such a direct way.