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One of my favorite books of all times is Zen and the Art of Motorcycle Maintenance. I read it every few years and recommend that every entrepreneur read it early in their journey.
While a plethora of entrepreneurship books have come out recently, including the ones I’ve written in the Startup Revolution series, there hasn’t yet been the equivalent of Zen and the Art of Motorcycle Maintenance for entrepreneurship.
Matt Blumberg’s new book -Startup CEO: A Field Guide to Scaling Up Your Business - has elements of it and is awesome. It should be out next month and every entrepreneurial CEO should buy a copy of it right now as it’ll be an incredibly important book to read for any CEO at any experience level.
Riz Virk’s post on TechCrunch yesterday – The Zen of Entrepreneurship - also caught my eye. He’s got a book out called Zen Entrepreneurship: Walking the Path of the Career Warrior. He’s sending me a copy but I went ahead and grabbed it on Amazon to read this weekend.
I know Riz from the 1990′s in Boston – I was an advisor to his first company Brainstorm Technologies. It was long ago enough at this point that I don’t know if I was helpful or not, but I had warm feelings toward Riz and smiled when I saw his name pop up again after not seeing it for a while.
Jerry Colonna and I have talked on and off about really digging into this topic and trying to write a philosophical treatise on entrepreneurship and the entrepreneurial way that will stand the test of time. I’m not ready to take this on as I’ve got enough on my plate, but I know it’s out there somewhere. In the mean time, I’m psyched to see more CEOs writing real books about entrepreneurship, rather than yet another ego testament to themselves.
Matt and Riz – thanks for putting the effort into this!
The Boulder TechStars program is in week three and the intensity level is high. The TechStars office is across the hall from ours at Foundry Group and it’s wild to see the level of activity ramp up during the three months that TechStars Boulder is in session.
I’m trying a new thing this program and doing a weekly CEO-only meeting. I’ve been trying to figure out a new way to engage with each program other than mentoring a team or two, and have been looking for a high leverage activity that I could do remotely for all of the other programs. My current experiment is an hour a week with all of the CEOs in a completely confidential meeting, but a peer meeting so each of them gets to talk about what they are struggling with to help solve each other’s problems as well as learn from each other.
We’ve done two of these meetings in Boulder and I love it so far. I’ll run this experiment for the whole program, learn from it, and iterate. If it works, I’ll scale it across all the programs.
Yesterday I also finished up my first set of 1:1 meetings with all of the teams. In my 1:1 meetings, I try to keep them very short – 15 minutes – and focus on what is “top of mind“. I learn more from this and can help more precisely than if I spent 30 minutes getting a generic pitch, which will likely change dramatically anyway through the course of TechStars. So each of these top of mind drills is “up to 5 minutes telling me about your company” and “10 minutes talking about whatever is top of mind.”
By the third week, I notice what I call “pitch fatigue” setting in. I think every entrepreneur should have several short pitches that they can give anytime, in any context, on demand.
- 15 seconds: Three sentences – very tight “get me interested in you” overview.
- 60 seconds: What do you you, who do you do it to, why do I care?
- 5 minutes: Lead with the 60 seconds, then go deeper.
- 15 minutes: Full high level pitch
- 30 minutes: Extended presentation that has more details
Bt week three, the teams are still fighting through getting the 15 second and 60 second pitch nailed. That’s fine, but there’s emotional exhaustion in even trying for some of them. The founders have said some set of words so many times that they are tired. The emotion of what they are doing is out of the pitch. Their enthusiasm is muted – not for the business, but for describing it.
Recently I was on the receiving end of a description from an entrepreneur, who has a great idea that I love, that had the emotional impact a TSA inspection at the airport. He was going through the motions with almost zero emotional content. At the end of it, I said one sentence - “Don’t get sick of telling your story.” I then went deeper on what I meant.
He responded by email later that day:
Thanks for articulating what was going on in my head. I think I was getting burnt out from telling the same story to so many mentors. I need to stay focused and stick with the story that worked well the first 40 meetings. I also need to be careful that the lack of “freshness” doesn’t affect how passionate and energetic I come across. Timing for this realization couldn’t be better given our upcoming fundraising trip.
I’ve done an enormous amount of pitching and fundraising over the years. When we raised our first Foundry Group fund in 2007, I did 90 meetings in three months before we got our first investor commitment. By meeting 87, after hearing no a lot (we got about 30 no’s out of the first 90 meetings before we got a yes) I was definitely had pitch fatigue. But every time I told it, I brought the same level of intensity, emotion, optimism, and belief that I did the first time I told it. Today, six years later, when I describe what we are doing and why we are doing it, and why you should care, I’m just as focused on getting the message across as I ever have been. And I never get tired of telling our story.
This post originally appeared last week in the Wall Street Journal as part of their Accelerators Program in answer to the question “When and how should you wind down a failing business.”
Some entrepreneurs and investors subscribe to the creed “failure is not an option.” I’m not one of them.
I strongly believe that there are times you should call it quits on a business. Not everything works. And — even after trying incredibly hard, and for a long period of time — failure is sometimes the best option. An entrepreneur shouldn’t view their entrepreneur arc as being linked to a single company, and having a lifetime perspective around entrepreneurship helps put the notion of failure into perspective. Rather than prognosticate, let me give you an example.
My friend Mark’s first company was successfully acquired. After being an executive for several years at the acquirer, Mark decided to start a new company. I was the seed investor, excited to work with my friend again on his new company.
Over three years, this new company raised a total of $10 million from me and several other investors over several rounds. The first few years were exciting as Mark launched a product, scaled the company up to about 40 people, and tried to build a business. But after two years we realized that we weren’t really making any progress — there was a lot of activity but it wasn’t translating into revenue growth.
In year three we tried a completely different approach to the same market with a new product. Mark scaled the business back to a dozen people in an effort to restart the business. Over the course of the year we tried different things, but continued to have very little success.
By the end of the year there was $1 million left. Mark cut the company back again — this time to a half dozen people. He started thinking about how to restart for a third time on the remaining $1 million.
Mark had never failed at anything in his life up to this point. He was proud of this, and the idea that he couldn’t at least make his investors’ money back was devastating to him. But he was stuck and started exploring creating an entirely different business, in a completely different market, with the $1 million he had left.
Mark was newly married and was working 20 hours a day. We were talking at the end of the day during the middle of the week and he was so tense, I thought his brain might explode. I told him that as his largest investor and board member, I wanted him to turn off his cell phone, take his wife out to dinner, have a bottle of wine, and talk about whether it made any sense to spend the next year of his life trying to restart the business with the remaining $1 million.
After resisting turning his phone off, I insisted. I told him that I gave him permission to decide that it wasn’t worth the next year of his life at this point and that as his largest investor it was perfectly ok to shut the business down and declare it a failure. I then said I was hanging up the phone and would talk to him in the morning. Click.
He called me back early the next morning. He was calm. He started by saying thanks for giving him permission to consider shutting down the company. This had never occurred to him as an option. During dinner, he realized he needed a break as he was exhausted. He wasn’t coming up with anything to do to reinvent the business and was just desperate to figure out a way to pay his investors back.
By morning, he realized it was time to shut things down, return whatever money was left, and take six months off to recover from the previous three years while he thought about what to do next.
We gracefully wound the company down and returned five cents on the dollar to the investors. Mark took six months off. He then spent six months exploring a new business, which ended up being extraordinarily successful. And he’s now very happily married.
Failure is sometimes the best option if you view the process of entrepreneurship as a lifelong journey.
When I was in Rio a few months ago for the Global Entrepreneurial Congress, I did a talk called “Day1” that Endeavor puts on. It’s a 20 minute presentation about “your day 1″ – a profound moment that impacted your entrepreneurial journey.
I decided to talk about a number of Day 1′s that I’ve had. I’ve always felt that with the dawn of each day is a new chance to “try again to be the best that I can be.” So my Day 1′s vary a lot – some good, some bad, but all full of lessons for me. They include:
- Me deciding not to be a doctor
- My first real job
- Hating MIT as a freshman and almost leaving
- Deciding to sell my first company
- Having Amy tell me I was a lousy roommate
- Learning they can’t kill you and they can’t eat you
- The power of a random day
I mention plenty of characters – some you’ve heard of on this blog and some new ones. My dad (Stan), Chris and Helena Aves, Dave Jilk, Len Fassler and Jerry Poch, Raj Bhargava, Steve Maggs, my partners Seth, Jason, and Ryan, David Cohen, and of course Amy.
When I give a talk like this I never really know where it will go when I start. I don’t prepare – it’s 100% extemporaneous. I was the second person to present a Day1 so I had 20 minutes to listen to someone else’s as I rolled around some stories in my head. Amy and I just listened to it together and it made us both smile and chuckle a lot with memories.
What’s your Day1?
The Deming Center for Entrepreneurship at CU is looking to hire a new Director. As part of the Leeds School of Business, the Deming Center prepares students across CU’s campus to think like entrepreneurs, act as social innovators and deliver as successful business leaders. It actively engages the community members of Boulder in order to accomplish this. The Deming Center also partners closely with Silicon Flatirons and other CU organizations to put on events such as the New Venture Challenge, Productive Collisions, and annually hosts the regional Venture Capital Investment Competition for MBA students.
This is an exciting opportunity to be part of CU and the larger Boulder entrepreneurship community. The person who serves in this Director role will have a unique opportunity to work with individuals both inside and outside the University to help foster and shape entrepreneurship on and off the campus. This person will also be responsible for the overall brand of the center as well as its operational and financial oversight. If you want to be part of a unique contributor to Boulder’s startup ecosystem, apply here!