Entrepreneurial Beginnings

It's been sometime since my last post on quitting. Since then I've been endeavoring on my entrepreneurial journey, while admittedly soaking up summertime in Boulder. I wanted to recap, if for no other reason than, to keep a running catalog of the course of events.

First week after I quit, I jumped right into Boulder Startup week. This event has come and gone with my attention for years, so my timing this year wasn't all that coincidental. I went to a number of activities and got to catch up and with those I've known professionally at some point in my 8 year tenure living in Boulder. In general, TechStars and it's attitude pervades the startup culture here. There are other players in town, but TechStars helped to pioneer the culture as it is. One thing I've felt personally and hear from others in the community is how Boulder is a 'give first' community. That's straight from Brad Feld and his notions on Startup Communities. The most helpful events were the TechStars mentor sessions and startup demo presentations. The Founder Stories were great too. These sessions reminded me of a book I read years back called Founders at Work. Super helpful for newbs like me. One thing I wish there were more of were sessions hosted by the bootstrapped. I've generally worked for bootstrapped software companies for the last 10 years, and there is something to be said for not taking money and making your own way. There was one excellent and informal session put on by SnapEngage. I learned some about Open Book Management and liked 3 things: they are super diligent about who they bring in, have a great operational model where workers can meaningfully contribute to company metrics, and everyone shares *equally* in the company's success. Seems like a great company to work for and something I'd hope to model my business operations after.

In the general search for more information on how to start my adventures, I'm keenly aware of the need for other cofounders. Not only does TechStars lean heavily on this, I've always enjoyed, as many do, the company you keep at work. Not to mention the numerous benefits of having someone else to do some lifting, execute where you are weak, and balancing each others life/mental roller coaster out. Finding a cofounder isn't easy, but nothing sends a message that you are serious like quitting a well paying job in the prime of your career. I'm lucky that I have a good background and narrative that seems to help when generating interest from others. I've been trying out CoFounder's Lab. Basically its a social network for those looking for startup opportunities and building a team. It's great to meet others who can help give you feedback on your idea, network, or form partnerships. The forum of networking needs a lot of love, and the random meets don't produce much return. You've got to talk to 20 people to find something of interest. I believe firmly that these things need to happen organically over time. It's obviously much more advantageous to have a cofounder that you've worked with in the past or even someone that's in your network, but my list has been tested already. Networking and planting seeds now is key, you just need to have a long term mindset.

I've had to put my ego and introversion aside. I'm cold contacting lots of folks in the area and in the industry. I'd guess I have an 80% response rate so far and persistence pays off for those high value players. Not knowing the industry I'm entering into, I put priority to those who know the industry or those who've started startups. It's important to know what the prevailing opinions are. You can't carve a niche out of an industry if you don't first know how it works. In the last 2 weeks a travel focused incubator, TravelPort Labs, has opened up in Denver, which seems to have alot of pieces that might help me. I met with them 2 weeks ago and I like that they are starting their own initiative for the first time like me, I'd get a decent amount of attention, they have experienced mentors, and helpful UX/UI resources. My reservations are whether we'd have conflicting operational approaches, the 1.25 hr drive each way, and if I'm limited to the travel industry in case the technology takes me elsewhere. In any case, I'll apply because I had a great conversation with 2 guys from the program.

Not knowing the industry and never having done market research, I generally was a bit disorganized at doing this on my own. But I found a few footholds with large market research firms, competitor analysis, and a gem of a site, Tnooz, which focuses on latest trends in travel, especially startups. I have a sense of the challenges in the travel planning space, the size, behaviors of the target demographic. The space is so crowded and generally everybody is faced with the challenge of 1 or 2 engagements per year and a high CAC. There's been a number of times I've gone to a travel planning site and been discouraged at the fact that a) it exists b) it seems well done from a UI standpoint. Then I test it and find the confidence to keep moving forward and carving out a niche. I'm the sort of entrepreneur that is a builder and have a personal need for the product, the question is whether others agree and are willing to pay for it. Nonetheless, it's at best a journey and a reasonable place to start.

So far I've taken a stab at the modern version of a business plan, the Lean Kanban board. I've identified my hypotheses and have strategies to get there. When you talk to the serial entrepreneurs around here it's "get out of the building", test, pivot, product/market fit. But in this "process", i think you need to have some core narrative or principles you are revolving around. For me it's technology, operational narratives, and an industry that you can give a shit about. I'd like to have all 3, but the buck will stop somewhere, that's what the hypothesis are for. From here on out when starting a business, you'll get tested on where to go and where to start. You need to really have your head on straight about who you are and why you are doing this.

That mostly sums up the activities of the first few weeks. Now I'm onto writing code and building a product, a subject for the next blog post.

Travel: A Necessary American Curriculum

I wish traveling was a required life curriculum.  Not vacationing, but travel.  Sitting on a beach sipping mai tai’s is plenty needed at points in life, but that's not what I'm talking about. How is travel different than vacationing?  I think when you travel you have a purpose in mind.  Perhaps you want to see and experience things.  Different perspectives, different food, different landscapes.  Perhaps you need to move through something, a problem or the vague notion of one.  Travel is best a journey that helps to step out of the patterns of your routine, and engage in the therapeutic activities of wanderlust.  Perhaps you’re keenly aware of how fucked up things are in your life and your therapies are much more deliberate in nature.  For other people, like myself, you love to learn.  Learning is a paramount activity for its own sake and there nothing quite like experiential learning.  Remember that scene in Good Will Hunting, where Robin Williams says to Matt Damon, “you’re just a kid, you don’t have the faintest idea what you’re talkin’ about…I’ll bet you can’t tell me what it smells like in the Sistine Chapel”  Experiential learning has a staying effect and an impression that's hard to replicate from other methods of learning.

Why should travel be required?  We’ve all met bigoted and ignorant people in life.  How much do you think those people have traveled?   "Travel is fatal to prejudice, bigotry, and narrow-mindedness." - Mark Twain.  Experiencing different cultures causes you to reflect on what has shaped you, and certain liberal rhetorics become more clear.  Chomsky’s Manufacturing Consent takes on a whole new meaning when you see how little advertising there is elsewhere.  Sure other countries might be outright corrupt when you need pay off the cops, but at least its on the table and not so subversive.  Military-Industrial Complex, Consumerism, Narcissism… these are concomitant side-effects of American society.  I'm not here to bash ‘merica, but merely see it for what it is.  Take the emotion out of the rhetoric by stepping outside of your routine and truly see how your circumstances came to be.  Engage, if but momentarily, in a different way of living or viewing the world.  Go to some non-western 3rd world country and see how much happier people can be even when they have little material wealth.

I remember reading Zen and the Art of Motorcycle Maintenance by Robert Pirsig in my travels to Fiji.  As an analytical person his analysis of the scientific process was eye opening to me.  Years later I read his follow-on, Lila: An Inquiry into Morals.  Lila touched on anthropology and explored a culture's values and mores in relation to other cultures, intellect, and biology.  These things take on a much deeper meaning when you understand just how different value systems of different countries and cultures can be.  It’s quite certain that nobody has it figured out, but surely some more than others.  When you see the connectedness and community of societies outside the Ayn-Randian dystopia, you can see that maybe you are missing something.  When reading Lila, I realized that most disagreements between persons stem from different value systems, different ways of looking at the world.  What I can see now is the black and white morality of a Christian derived US value system, is really bullshit.  Right and wrong is just a matter of what side you are on.  And the driver of war is keenly driven by our primitive aspects of ‘us vs them’.  Nothing codifies a group of individuals like having an enemy: in business, in sports, in nation building…  What does this have to do with travel?  You develop meta-attitudes and value systems that embrace other cultures.  You become a citizen of the world, not just the US.  

Do you travel?  Did you used to?  Do you have a ‘wish/bucket list’ in the recesses of your mind?  Dig it up, plan a trip.  Do you have a family?  There are a ton of resources out there on family travel.  Are you low on money?  There are resources out there for being a nomad on dollars a day.  Do you only have 3 weeks of vacation and use it sparingly.  That’s just a shitty excuse.  And a broken byproduct of the American work culture best known as the Paradox of Productivity.  We are the least traveled of any developed nation and its at our detriment.  Maybe you’ve read the top 5 regrets of the dying, most of it is obvious right?  The challenge is to step out of your routine, to make it a priority.  Or perhaps you’ve seen that paying for experiences is vastly better for you than material things.  By no means am I a nomad, but I live well within my means.  And I’d like to think I'm unconstrained by those trappings of American materialism.  Fuck your car, your house, your overinflated sense of self worth at your job, and go travel.  And travel with purpose. (When you do, feel free to share with me how flawed my views of contemporary American society are.)