I recently finished an excellent book called Founders At Work. It’s a series of candid interviews with thirty-two dot-com founders and it shares the same goal of our Grid7 podcast to get the story directly from the people that started companies from scratch and distill their wisdom. I started taking notes at the beginning of this book with the intention of doing a single blog post summarizing my thoughts. By the time I finished I had eleven pages of notes- lessons that rang true from our own experience in doing a start-up, synergies from other blogs and podcasts and quotes from founders that just struck a chord. I wound up with way too many thoughts from this book to cram into a single post.
So I’m doing an exercise this month. May has thirty-one days and there were thirty-two chapters in the book. We’re also marching towards June 1st as the ship date for the product we’ve been building the past nine months and it would be neat to coincide the final post with our first revenue. So I’m doing a post each day for the month of May to share my thoughts on each of the founder vignettes to add our perspective from building JumpBox.
There were recurring themes across all interviews-
- the “Midnight Run”
- the positive byproduct that came with being forced to work under tight resource constraints and the subsequent downfall that often followed when those constraints were lifted
- the viral element that many offerings shared
- the critical necessity of the open dialogue with the customer
- and the healthy suspension of disbelief that was required of the founding team from the beginning in order to do the impossible.
The one thing that was entirely consistent across all interviews was that the people were extremely likable – their passion, their candor and their dedication in the face of adversity – I just wanted to meet each one of these people and shake their hands.
The first of this 32-part series is available here on Grid7. If you’d like to follow along this month you can subscribe to the RSS feed for that site. The intent is that by conducting this exercise we toss in our perspective and help influence anyone out there who is contemplating taking the same plunge that we faced nine months ago.
This point was hammered home in an exercise we did recently in our 
Crafting a pitch in the absence of feedback is like spending energy to build the perfect steel-reinforced bridge half-way across a river- it’s pointless unless it connects to the other side. Try out your pitch on some friends. Then approach them three days later and ask them to repeat what they remember. Whatever comes back is what stuck – it is the essence of how your pitch is currently received. Just like the game of telephone where the message gets garbled in re-transmission, your pitch is only as good as that final version which gets relayed second-hand at the cocktail party. Doing recon on that second-generation essence gives you invaluable info about how your pitch needs to be altered.
For those unfamiliar with what kite surfing is, it’s a water sport that meshes wake boarding with the art of flying an over-sized kite and using the wind to generate the power that a motorboat would normally provide. Also known as “kite boarding,” this sport is the fastest growing water sport in the world right now. A skilled kite surfer can navigate upwind tacking like a sailboat and launch several stories into the air by timing a jump off of a large wave. I had the opportunity to 
There is a useful mental abstraction in kite surfing called the “wind window.” The wind window is an imaginary quarter sphere that extends around you and occupies your peripheral vision as you are standing with your back to the wind looking straight ahead (like a big orange slice downwind from you if you are one of the seeds). This is the space in which your kite will fly when its tethered to you. Now imagine a colored gradient superimposed against this quarter sphere where the red zone is that spot directly downwind and the concentric zones of the sphere that radiate outward from there to the edge of your peripheral vision are gradually cooler colors. Weird I know, but if you’re visualizing it you should have something like the picture on the right.
The takeaway here is that, much like with a startup, there are a thousand different things you could do at any moment to improve your situation, but with limited resources it’s all about determining where that power band is at all times. Some startups have blown millions optimizing kite skills with their kites around on the periphery while others have succeeded on shoestring budgets with a small, crappy kite and minimal kite mastery but by keeping their kite in the red zone. At least 50% of this game is identifying the power band.
The holy grail of a wind sport is to go upwind. Any jokester with a sailboat can raise full sails and go wherever the wind takes him/her. It takes true skill to know how to tack and travel against the wind – but once you can do that you can go anywhere. In the same way, anyone with deep pockets can start a company, throw up the sail and go downwind. Bootstrapping with minimal resources means you have to learn to travel upwind.
