Independence Day & Quicksand

On this long weekend celebrating our country’s independence, I’ve had the opportunity to reflect on the past couple of months since I left oneforty to work on my own startup.  It’s been good to reconnect with a lot of people who I didn’t get to while being heads down at oneforty, recharge my batteries a bit, and have some success in the cofounder search. That being said, I’ve also realized I’ve walked into quicksand…


On the football field, it’s when one thing after another goes wrong despite trying to make plays. In startups, it’s when you let something paralyze you and sink your entrepreneurial efforts. It might be because you focus too much on the wrong thing or ignore the most important thing.

I have tried to plan so many parts of this startup I’m now working on. Whether it be meticulously noting the learnings of the past year at oneforty, saving money so I can go without a salary for a very long period of time, or mapping out all of my contacts and the best ways to leverage them to succeed, everything has been carefully calculated.  I even focused on finding a great tech cofounder before the idea, so I was sure I had good alignment with them before we started running on an idea. All of this though ignores a key element: the idea. It is in this search for the idea that I’ve found myself in quicksand.

Searching for Inspiration.

Being calculated and focused is great for planning to save money and preparing to launch a company, but it’s terrible for trying to generate an idea. You can’t force inspiration.  I know this not for lack of trying:

  • Tried using David Skok’s brainstorming process he blogged about (coincidentally posted my first day after leaving oneforty).  It just left me feeling like a VC; knowing what are good, interesting industries, but not actually feeling like there was a specific idea to go work on.
  • Brainstorming with friends. I hit the white board with friends trying to flesh out some ideas, but only managed to write off a few ideas and failed in trying to dig deeper on ideas identified by using David Skok’s aforementioned process.
  • Talking with friends about the industries of their startups. I talked with a lot of friends in the community about what they were working on to see if any industries caught my eye.  Nothing seemed to spark.
  • Helping friends with their startups.  I tried helping a couple friends with their startups to see if I liked what they were doing (and might join them) or if their industries seemed like it had any interesting problems to solve.  The first two attempts yielded nothing and the verdict is still out on the 3rd.
I’ve found the harder I’ve tried to come up with the idea, the more I’ve sunk.

The Paradox of Choice

I feel a tremendous amount of pressure to come up with an incredible idea. A friend of mine mentioned over coffee that he hopes I don’t become Jarrod Saltalamacchia and it fits how I feel; Jarrod was a hugely touted prospect that came up from the minors and everyone expected he’d be the next great major league catcher.  As it turned out, he’s ended up being more of a journeyman.

I feel like I have to get a big hit in my first at bat and it has crippled me; everything feels like a non-starter because no idea feels “good enough.”  It’s also hard because the closest focus I’ve found is that I know I want to build a B2B SAAS company (mainly because I feel there is the most support and related companies here and I understand B2B more than consumer web.)

Digging Out

Realizing this is happening and admitting it feels like the first step. More importantly is what happens next.

David Cancel gave me great advice at RubyRiot that I haven’t heeded well to this point. He said, “save someone an hour a day and build a business around that.”  It also harkens back to the most obvious solution that’s been standing right in front of me the entire time: Customer Development.  Somehow, in all of this, I’ve done very little customer development (other than when helping friends’ startups).

What Now?

As a recent blog post said, “A lot of people talk about Lean Startups and customer development, but very few people really do it.” I need to get outside the f@&%ing building.

Here’s how you can help:

1) What sucks in your day to day or someone you know?

What makes you complain or you’ve heard someone say is horribly inefficient, and totally not in Web 2.0 and should be? I want to talk to you and/or them! Seriously, even if we don’t know each other, drop me an email at evanish.j [at] gmail [dot] com and tell me about your problem.

Don’t worry if you think it’s a boring problem; I in fact prefer unsexy problems. I’m hoping to solve a problem that doesn’t have 25 Valley startups working on it.  One of my favorite startups a friend is doing (not in Boston) is working in a space where his direct competitors are…call centers. That’s a fun problem to solve.

2) Got an idea you wish existed but can’t work on?

I’ve already talked to a few of you that have shared ideas where you said, “If I wasn’t doing my startup, I would do this.”  If you find yourself saying that, I’d love to buy you a coffee or beer and see if it’s something I can help make a reality.  I’m very happy to make you a beta user ;- )

3) Hold me to this.

Whether you have a problem or know of one I can solve or not, please hold me to this.

Don’t ask me how I’m doing next time you see me. Ask me if I’ve gotten outside the building.

Torture and Culture

Thanks to the “War on Terror” the topic of torture is much more front and center than it was in the past.  As life mirrors art, I’ve noticed that popular culture has picked up on it.

In movies and television, torture has become an increasingly prevalent piece of plots. Jack Bauer, hero of the long running show, 24, has regularly used it to get answers and even supposed unexpected everyman hero, MIT educated, Sean Walker of The Event has used torture to get answers.

With real life and art showing torture so prevalently…is it any surprise that more than half of all American teens condone torture?

What’s most interesting is that it wasn’t always like that. We didn’t always glorify it or even condone it.

I just finished watching an old Star Trek the Next Generation episode that addressed torture head on and was far from supportive of the practice. In the episode, Captain Picard is captured by an alien race and tortured for answers. He refuses to break down and repeatedly discusses the ethics and effectiveness of torture. In the end, once he’s free, he admits to the ship’s counselor that after the torture not only was he willing to tell them anything they wanted, he thought he *saw* what they told him to see. (The episode is called “Chain of Command” and you can find an awesome article examining the episode on Slate here.)

As art can also mirror life, it’s well worth noting a practice from World War II. At Fort Hunt, high level German prisoners were subjected to chess, ping pong and steak dinners. Shockingly, these prisoners befriended their captors and divulge massive quantities of highly accurate information. Learn more about the incredible story here.

Our military’s practice of torture is only further enabled by our cultural embrace of its supposed effectiveness. The survey of teens shows that we may be more impressionable than we like to believe. I’m genuinely concerned for the implications of our future where the majority of people embrace practices so contradictory to our founding principles of Life, Liberty and the Pursuit of Happiness.

Yes…I finally have a SmartPhone and it’s an iPhone.

Yes, this is the phone I had up until 5pm today....

So it finally happened. I caved. After holding out a solid 17 months in the startup community, I finally got a smart phone.  It was kind of amusing to see how shocked some people were and frankly, I can see why you might not expect it after I previously debated this and chose iPad + dumb phone.

So here’s what tipped the scales as key things I wanted:


1) Ability to save notes and contacts anytime

I have a horrendous memory and I feel like a total douche when I can’t remember people’s names. So one of the first things I intend to do is  start writing down everyone I meet in my phone each night. I can then also add notes for action items so I don’t have to just say “email me.”

2) Try other Startupers stuff

I have a lot of friends with smart phone apps, and I feel bad I can’t try them.

3) I’m tired of printing out google maps and calling friends when lost

I got lost last week trying to walk to Kabir’s house. I called him and he asked me, “what do you think I am? Google maps?”  He then told me how to get to his place, but there’s a lot of times I mooch off friends to get to the right place because of this.

4) The adoption curve is pushing me to the minority

When I saw where the adoption curve was going with smartphones (projected to surpass 50% in 2011), I realized I can’t be in the techscene and thinking about startups and not have one.

5) 40404 Tweeting gets old. Fast.

I tweeted a lot with 40404, but I can only do one account with my phone number that way which meant it was all Greenhorn.  Also, 3 letters to a key makes even a tweet a lengthy ordeal. Finally, working at a startup focused on twitter and thinking about the huge presence Twitter has in my life, being able to Tweet, is actually pretty important to me.

6) SXSW is coming…fast!

In the interest of not being the next RazrDude (ask Chris Keller about it…) and actually being able to reach people when I need to…this was the real impetus. I’m going down on behalf of oneforty and need to be able to meet up with Janet and Laura, and we’ll be most effective if we’re all free roaming, I think. I’ve also heard foursquare is hugely important and obviously a smartphone comes into play there.  I concluded I couldn’t be maximally effective there without a smart phone.

So there you have it…that’s why I have a Smart phone…finally!

Do you have an inner Pit Bull?

I have one. Do You?

Not sure what it is? To me, it’s when I get really fired up about something. Much like a pit bull, it’s all about encroaching on my turf or otherwise threatening something important to me.  I can’t help but feel a fire inside that just charges me up to take on whatever challenge comes up.

Now unlike your average fool at the bar, this isn’t about someone bumping into me or looking at me funny; it’s more in actually the business environment.  Nothing quite fires me up like some good competition or healthy negotiation.

I also see a parallel to sports…look at Michael Jordan…he just criticized LeBron for going to Miami and I totally get it. Jordan was pushed his whole career because he always had people challenging him on other teams that forced him to get better.  Kobe has been the same way, working harder than anyone to be the best. Love or hate Kobe for his personality, you can’t argue with how unbelievable his shot was in the NBA Finals (when Ray wasn’t smothering him…).  That fire I think is essential to success in whatever you do, as long as you can keep it under control.

For every Jordan, Bryant, Jobs or Zuckerberg, there are tons of people that let their heads drive them to self-destruction.  So how do you channel your inner pit bull to feed the fire when you need it and not destroy yourself?  I’m not sure totally, but I’m trying to understand it better; in my past I’ve found the inner pit bull has gotten me in trouble a few times but in general has been a net benefit.

The extra fire has helped carry me through many a challenge and luckily, instead of being blinded in rage, it has actually helped me think harder on challenges. Some of my most resourceful and innovative ideas have come while in “pit bull” mode. I think this is because when in “pit bull” mode I’m incredibly focused; nothing else gets in…it’s just me and the threat/challenge in front of me.  With that opportunity of clarity, it’s almost “easier” to come up with solutions.

So do you have an “inner pit bull” or what would you call it?

…Consider this a very open-ended, partially thought out post.  It will be connected to a more thought out blog post on Greenhorn Wednesday.

The smart phone decision: an unexpected choice

So after much deliberation, I’ve decided I won’t be getting a smart phone after all.  Instead, I’m going to get an iPad. Here’s why:

1) I don’t feel there’s enough missing in my life that a smart phone can do.

Yeah, I want to be one of the cool kids and have a new gadget to show off too, but in the end, after playing around with a few friend’s iphones, I just couldn’t justify it.  I didn’t feel like there were any “killer apps” that would change my life if I had it.

2) The Price

By my calculations, it was going to cost me about $800-$1,200 over the next year to have a smart phone.  Meanwhile, the iPad with 3G for a year would come in at the bottom of that, $800.  And the second year, when I’m not considering the cost of the item in it, it has a significant cost advantage at just $15 for data.

3) The iPad did have the killer apps

After about 15 minutes with the oneforty company iPad, I realized I wanted one.  It has this strange magic ability to fill a gap I didn’t know I had in my life; now I can’t wait to run through a bunch of saved blog posts on instapaper and it feels so much less intrusive to have an iPad in my living room while watching TV with roommates than it did having a full fledged laptop burning my lap.  The giant color screen is also really powerful for displaying everything from websites to simple one to one presentations.

4) The iPad is just an iPhone with a bigger screen

So evaluating things overall, and I see that the iPad can do any of those magical things that the iPhone can do, but with a much bigger screen. I personally cannot imagine using a 3.5 inch screen to read emails or blog posts, so I’m happy to have the advantages of the big screen and none of the stress of needed it to fail at making phone calls.

5) Dumb Phones are still the world’s majority

Want to make a killer app to serve the world? It’s going to be on dumb phones.  Smart phone proliferation is a luxury of the wealthy.  There are billions of people just getting any cellular technology and that will only be on “dumb phones” for some time.  As an entrepreneur, I think you’re at your best when you’re one of your own customers.  Therefore, to keep in mind some of the biggest opportunities, I’m keeping my dumb phone.  I couldn’t find any current statistics I found satisfying to put here, but if I find one that shows the cell phone breakdown of the world, I’ll definitely add it later.

So I doubt there are too many people that are going to be rolling with a LG VX8300 and an iPad, but hey…who doesn’t want to be a trendsetter?

Life I chose or the life that chose me…

So tonight I got a text from a friend…actual exchange:

Friend: I have big news!

me: Yeah? What?

Friend: We got engaged!

me: With who?!?

Friend: Seriously? My now fiance Brandon

me: Sorry. havent seen u much the last 6 mos. congrats! heard youre headed to grad school too. when are you having a big nite in boston?

This sums up a lot of my life since being “greenhorn” become a part of it and really since I started grad school in sept. 2008.  I have chosen learning about entrepreneurship and building GHC over everything else.  Until I started working at oneforty, I attributed part of it to being broke; I was cobbling together odd jobs and living off savings. But now I have a great job with a healthy paycheck, and I still find myself almost always choosing startup life over things normal 25 year olds do.

In a way, tonight was a wake up. But in many ways, it’s just a blip on the radar.  I have zero regrets. I’m very proud and grateful for how far I’ve come thus far and still feel like there’s so much still to do, so much to learn and still behind where I need to be; I feel like every moment I work at oneforty and work on Greenhorn Connect, I’m learning so much, it’s sooo hard to want to put it down for any meaningful time.

I’m 25. It feels so old and yet so young. Mark Zuckerberg and LeBron James are less than a year older than me. They remind me to stay hungry and realize there are no limits; if they can do what they’ve done, than the trivial things I can do must be easy.

At the same time I realize that maybe I need to “enjoy” a bit more of my 20s; is the relentless pursuit of startup nirvana really how I should leave every moment of my life, or can I effectively pursue it and still be an average 25 year old every once in a while? I don’t know…but I’m going to try.

Why Barnes & Noble is going to go out of business and I don’t mind…

Having finished the last of the books I had stock piled to read, I realized it was time to pick up some new reading material. Since I had a Barnes & Noble gift card sitting around from Christmas, I thought this was a great time to use it. I didn’t want to wait for shipping, so I ventured into the Barnes & Noble at the Prudential Center with the goal of picking up Steve Krug’s Don’t Make Me Think and Jason Freid’s new ReWork. I thought it would be easy enough…go in, find ReWork in the business section and Krug in some type of web development/design section.  Not so much…

So after wandering all the way to the wrong side of the store, I finally found the business shelf…but couldn’t find ReWork. I stumbled across a kiosk, but despite it’s insistence the book was in the middle of the area I was in (note: the kiosk didn’t have the most up to date shelving set up…#fail), I couldn’t find ReWork.  I then figured I’d look for Don’t Make Me Think, but their web development and design sections are a mess of photography how to books and random coding languages jumbled.

I finally grabbed a B&N staff person after about 15 min of feeling like a blind man in a library and they took me to their main station.  Turns out they only give the best treatment to Jason Fried’s new book: ankle level on a special shelf halfway under a table about 2 feet from the help desk…obviously easy to find!  With ReWork in hand we then went searching for Don’t Make Me Think…unfortunately, much thinking was required as we searched the jumbled mess of web and design sections.  But alas…finally we found it.

Then I went to the check out:

Don’t Make Me Think: $40

ReWork: $22

Tax: $3.88

Total: $65.88***

Note: The cashier was kind enough to offer me the opportunity! to pay an additional $25 to become a B&N club member and save 15% on all purchases!!! What a deal! She reminded me, that I’d save $9 on my books today if I got the club membership…ignore that’s still a net extra of $14.

Now: Why Barnes & Noble is going to go out of business and I don’t mind…

If I go to…I can get both of those books with free shipping for: $38.50.  I can also immediately find the books by simply typing in the title or author. I can also see reviews to make sure I really want the books (luckily, both have already come strongly endorsed by my Tweeples).

So let’s see…save over 40% (much more than that awesome B&N membership!), find stuff instantly and deliver it to my doorstep? SOLD.

Sorry B&N…I’m going to use up my gift card $ and not only not come back, but ask my mom for gift cards next year.

Learning: Amassing Knowledge vs. Creating Understanding

In my “New Year’s Resolution” post I promised to write more…that hasn’t really happened as most of my writing time is committed to Greenhorn Connect related content.  However, I’ve just had an inspiration for a post and so I’d like to share it here.

Since I really dove into entrepreneurship a few years ago, I’ve found I have an insatiable thirst for learning anything and everything related to the topic.  All this time though, I’ve been thinking about what that really means, “to learn.”  I think that in life there are many that seek to learn, but often it’s merely to amass knowledge; I know this fact or that statistic. I’m well-read on this subject.  That’s all well and good, but if they’re just facts and merely someone else’s ideas…how much has been gained?

My goal is not to just amass facts. I’m not looking to be an encyclopedia.  I want to understand. I have so many questions about so many things. And yes, studying and reading always helps, but I always consider it in the context of greater understanding. I think this analogy may help:

You have a farm. On this farm all kinds of fruits and vegetables grow.  Those that are merely amassing knowledge would look at what they have and say that they have hundreds of broccoli heads and thousands of ears of corn.  Those building understanding look deeper and understand how they can take the vegetables and make salads and juices and other unique dishes; each item grown on the farm represents an ingredient, not an end result. When they file this knowledge away of the farm and its produce, those with understanding are thinking of it from the perspective of how the different dishes were made from the farm, while those amassing knowledge only see it in the narrow verticals of each fruit or vegetable produced Those with understanding are also more easily able to transport the concepts created from the dishes from the farm into other areas; everything around them is a small piece to a bigger picture…one that is not necessarily completely clear, but is larger and better than before because of what’s been added.

I think that it’s as important what the question you’re asking is as the means to which you’re going about your learning. For example, I’ve recently become very interested in user experience.  The questions I have are related to better understanding people. I want to be able to better step out of what I think (and all the biases and preconceived notions distorting it) and be able to understand others.  My impressions when I come to a website are not the same as someone else’s.  To accomplish this, I could go straight to a bunch of UI/UX web books, but I think it’s important to go broader than that, so I’m going to try to cast a wider net to truly understand people.  Incidentally, as I work towards this goal, I believe I will be able to apply this new understanding to other areas of my life in human interaction.

How thoughtful are you with your learning? Are you amassing knowledge or creating understanding?

Naming is so (not) Important

The name of your business is everything.  It’s the first impression of your business. It tells people what you’re about and sets the expectations.  You only name your business once, so you have to love the idea. And yet…in the world of domain camping, millions of social media accounts to reserve and a never ending battle for customer mind-space, there’s a lot of factors to satisfy.

Naming Greenhorn Connect took many weeks of thinking about what the name should be and then suddenly just came to mind and we ran with it. We’re now in that “nothing sounds right and we can’t think of anything good” phase for Doodlebugging.  Much like with Greenhorn, bounties offered to others isn’t yielding anything great either (if you’d like to suggest a name, and we use it…we’ll give you $50.)  Still, I’m sure we’ll end up with something…it’s just annoying and feels like a waste of mind space and productive time to think about it.

I’ve read all the tips about making it memorable, getting the dot com of your name and what makes the best choice from a trademark perspective, but does anyone have any real tips for coming up with a name after you remember those basics?

It’s a Black and Blue and Gray World…

As we move through the toughest part of Boston’s annual weather cycle, I’ve noticed that the colors of people’s wardrobes have gotten increasingly dark and muted. It creates an interesting sea of similar looking people and crowds. I feel like this wardrobe boredom is probably for a few reasons: dark colors are slimming (holiday/winter gain from inactivity), reflection of attitude (winter can be depressing) and it’s easy (black goes with everything!).   This provides a unique opportunity for anyone willing to buck the trend.

If you’re a high energy person, this creates a fantastic opportunity. Wear some color. No really, put on that red sweater, that shiny blue vest or that…bright green shirt.  You will stand out and your energy can draw people in.  It’s a great tool for networking, for going out or whatever you’re doing.  If nothing else, people will notice your lack of black/grey/blue-ness and wonder a bit about you (in a good way).  At best, they want to come over and talk to the interesting person that was bold enough to wear something different.

Clothing is one of the best ways for your personality to show through. Let’s get a little more color out there and turn the energy level up a notch or two.