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There’s been some anxious moments the last few weeks in the startup  I’m working on.  It’s the typical fears that you deal with in this stage of a startup (basically, what if we fail?).  I’ve been deep down this fearful road before, but this time it feels different.  I’ve been able to watch and notice more than ever, and it’s really interesting what I’ve seen.

I’ve noticed that often times we connect the anxiety and the situation as one, therefore calling it an “anxious situation.”  The tendency is to act quickly, swiftly, aggressively to solve these anxious situations.  In my own moments of high startup anxiety I’ve responded by working longer hours, setting up elaborate tasks list, creating crazy work rules for myself, and lost hours of sleep.  The funny thing is those all actually increase the anxiety.  Why? Because my work or work ethic was not the issue, the anxiety was the issue.  I’ve learned you need to work through that first, which often times requires a break and a breather, and then you can come back and deal with the tasks at hand (which usually are NEVER as bad as they look when you were anxious).  Or as Jerry put it in an email conversation earlier:

In fact, some times the anxiety can be so high it can actually prevent you from putting together the structure you need (to make you feel less anxious!).

There’s a big difference between the anxiety and the situation.  The anxiety is not tied to the situation, the anxiety is your reaction to the situation, and the anxiety makes dealing with the situation more difficult.  Step back, reflect, separate the two, and move forward…


2009 to 2010 thoughts

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We are now less than one week away from the end of 2009, and the first decade of the 2000’s.  As I look back on 2009, there are a lot of great lessons, ups and downs, victories, and losses, but ultimately a significant amount of progress in my life.  Life it seems is really about the balance between  enjoying and appreciating who and what you have currently, and at the same time continually pushing for growth.   Simply said: be truly grateful for the present and think and act big for the future.  Easier said than done.

Anyway looking back on 2009 for me I can see a few personal lessons to carry forward:

1.) Talk about it.  I wrote about this back in July. This year, particularly in my relationship with Julie, this lesson finally sunk in for me.  Communication is not about finding solutions, it’s about connecting with someone else, and generally it makes everyone feel much better.  I think we  feel better when we open up to another person.  And generally it is much easier to find solutions (if that’s what you’re looking for) when you are feeling good and open.

2.) Don’t do something just because you think it will make you money.  Sounds very obvious, but man is it a hard one.  As I wrote about back in May, I learned this lesson the hard way, spending almost a year working incredibly hard on a concept because I thought it would be a somewhat easy way to make money.  I of course was wrong.  Building a business is a long process with lots of ups and downs.  If you don’t have more interest in the process beyond making money, getting through those downs is going to be rough.

3.) When it comes to business concepts or projects, there is a big difference between a good one in general, and a good one for you.  For me at least, just because something seems like a good idea does not mean it’s a good idea for me to pursue.  I again learned this the hard way, as discussed in this post. (I may reference this post more…)

4.) Plan for and demand time for thought.  Big ideas don’t usually happen when you are checking email, sports scores, listening to podcasts, watching tv, etc.  They usually happen when your mind is allowed to think, free of distractions.  It’s way too easy to get sucked into the flow of the day and the week, and not give yourself time to reflect.  The reflection time is really when interesting thoughts come forward. And by the way, I don’t think time for thought should be all about allowing the big ideas to come through either…it should be just for thinking as well.

5.) JFDI. I just wrote about this. This one is a biggie for me.  I’m really good at putting things off, especially tasks or situations that may make feel uncomfortable.  I’d rather just push them to a later time and date.  There are usually 2 consequences that stem from that approach 1.) Generally the situation / problem worsens with the delays 2.) you feel worse and worse about putting it off.  There are definitely situations where a bit of reflection is the right move, but 9 times out of 10 we know what action needs to be taken almost immediately.  Act and you’ll get more done and feel better.

6.) Be Optimistic.  Sounds simple, and I guess in theory it is.  But for me it can be a struggle.  There’s a voice in my head that is optimistic about things 70% of the time I would say.  The problem is the other 30% of the time it’s very pessimistic.  This voice sees the “bad” in my life as permanent and a direct reflection of who I am as a person.  That’s a hard one to deal with.  In making a conscious effort to notice this voice and brush it aside, it’s amazing how much better life looks day in and day out.  Again it’s not easy, and it seems to be a long process, but just noticing the downer voice is a big first step

7.) Be your biggest supporter, not your harshest critic.  Similar to #6 above, I’ve really become aware this year of the inner critic.  When that voice is strong in my head, things really feel hard in my life.  Nothing I’ve done means anything.  Nothing I’m working on will ever be good enough.  I haven’t treated this person correctly, or said this when I should have, or called this person in a reasonable time.  Certainly there are times where that voice needs to come through to make adjustments and teach lessons, but it needs to change its tone.  I’m looking for one that teaches, guides, and supports not criticizes.  First step is noticing the critic, something I did very well in 2009.

I skipped a few years with this tradition (last one was 2006, which looks very similar to this years), but think it’s a good one to continue going forward.  Happy and healthy 2010….


How far are you willing to go?

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I’ve had the pleasure of having front row seats to watch my friend Jason develop his business Jackthreads (check it out, it’s a private shopping community) over the last 4 or so years.  Things are going very well for Jason now as his membership and revenue numbers continue to explode month over month.  More importantly he’s now able to work full time doing something he loves with customers and employees who also love what he’s doing.   The business is now drawing all sorts of interest from investors to partners to customers.  Everyone seems impressed by this thing that seemingly popped up over night.  I can tell you, it didn’t. Jason took the long path here. 

He started out 4 years ago with a totally different business model. He has had more than a few people tell him he was crazy, that his idea was off, that he had no business building something like that from Columbus, OH.   He had all kinds of jobs from bar back to sales consultant to selling towels just to sustain himself while he worked through this concept.  He burned through multiple  programming groups / teams and watched his development process drag on and on. He had to work tirelessly just to get someone to give him a chance to test his concept.   He had more than a few “what the hell am I doing,” moments.  There were more moments where quitting made more sense than going on.   Obviously, he chose to stick with it.

As an entrepreneur, you are going to have lots of “what the hell am I doing,” moments.  It’s a key part of the journey. In fact most cases are like Jason’s, where you must go through the grind of work and doubt until you finally see some traction.  The deciding factor ultimately is how you deal with those moments.  Do you stop as so many do, and as I have done?  Or do you push through as Jason did.  How many moments of doubt, how many “no’s,” moments of frustration, odd jobs are you willing to go through to see your idea to fruition?  How far are you willing to go?


“Make meaning not movement”

I was having a discussion about entrepreneurship yesterday with a friend and I mentioned that I can see one of entrepreneurs at one of the startups I’m consulting for really starting to get anxious about money.  I mentioned that I could see their anxiety manifesting itself in pushing for more…more time, more phone calls, more emails, more stuff.  But at the end of the day when I look back all of the things we / they have done as a company over the last 4 months, there are really only a few high value activities, and none of them seemed to come from “doing more.”  There is a lot of chatter, particularly email and skype chatter, but very little of it seems to translate into real value for the copmany.  It just yields more chatter, but it feels like doing something, and when people start to get anxious they feel they can solve the anxiety by just doing something.  It doesn’t work.

In my discussion yesterday, my friend told me he has seen this time and time again in startups, where entrepreneurs think the cure for their problems is by making more movement.  Instead, my friend suggested, “make meaning, not movement.”  This is certainly easier said than done.  And you might say “well the only way to know what creates value is to try lots of things.”  I do think that is true to some extent.  But often times what I see and do (I’m very guilty of this) is sort of a blind blur of activity in hopes it will make something happen.  Amazingly people (me included) take very little time to take a step back, and really evaluate the situation.  It is only within this “meta” perspective that you will be able to spot opportunities to “make meaning.”

So I was pleased to stumble upon this blog post today from Caterian Fake titled “working hard is overrated.”   My favorite section of the post was a quote  from a book titled “Smart World,” about Watson and Crick, who discovered the structure of DNA:

At times the two central protagonists behaved like people whose day job was working up skits for Monty Python….they had distinctly lackadaisical work habits. Watson played several sets of tennis every afternoon and spent his evenings alternately chasing ‘popsies’ at Cambridge parties and going to the movies. Crick, who rarely showed up at the lab before 10 AM and took a coffee break and hour later repeatedly appeared to lose interest in the problem of DNA. On more than one occasion, vital piece of information were obtained not through hard work but as a result of chance conversations in the tea line at the Cavendish laboratory.

I love the last paragraph of her post to summarize:

Much more important than working hard is knowing how to find the right thing to work on. Paying attention to what is going on in the world. Seeing patterns. Seeing things as they are rather than how you want them to be. Being able to read what people want. Putting yourself in the right place where information is flowing freely and interesting new juxtapositions can be seen. But you can save yourself a lot of time by working on the right thing. Working hard, even, if that’s what you like to do.

Make meaning not movement.


no regrets about going with my gut.


Image by Mick Opportunity via Flickr

So I was watching the Techcrunch 50 tonight live on ustream while waiting for Julie to get off the phone before watching Mad Men, and just as I was about to switch it off, I saw a name I recognized.  The upcoming presenter was a company called Yext, a company I knew.  My jaw hit the floor.

You see when I first moved to NYC 3 years ago this week, I was all open and up for anything.  I told myself I just wanted to do something interesting with people I could have fun with and learn from.  I wanted to continue pursuing my path as an entrepreneur either by starting my own company or coming on board VERY early with another startup.  So I went to all sorts of meetups, NextNY events, and made lots of random linkedin meetings.  It was actually fun, and quite honestly I don’t remember a lot of the people I met with during that time, but I do have to say, I remember Howard.

I actually met Howard on Craigslist.  One of the things I did at that time to increase my chances of meeting interesting people was to post something on Craigslist saying basically I was an entrepreneur, I had just moved here, and I was looking for another entrepreneur to to partner up with.  I got a LOT of responses to that posting, and about 99% of them were junk (no offense to the responders).  But Howard’s for some reason intrigued me.  I think it simply said “I’m interested, tell me more,” but I did a little digging on his email address and I found an old article about him being a hot shot college entrepreneur.  I gave him a call, we connected over the phone so we decided to meet.  We met for drinks a few nights later.

I actually liked Howard right away.  He’s clearly very smart, he’s very direct, and he’s vision driven.  He had a lot more experience as an entrepreneur than I did, and really knew his way around NYC.  He told me he was working on an idea around generating leads for local businesses, using his previous company experience “driving millions of qualified leads (he said this a lot).”  He said he had another co-founder, the tech guy, and they were looking for someone else to bring on.  I was very intrigued.  Actually I was really excited.  We agreed to meet a few more times, and to meet when his partner came into town.

After a few more meetings, and a quick trip to Chicago for a conference where I was able to see reactions of potential customers, they offered me a deal.  They wanted me to join them as a founder and to buy into the company at somewhat higher valuations than they had.  I also had to agree to stay on for at least 3 years to get all of my equity (I forget exactly all of the details).  I was a little nervous about the money, but was really nervous about being locked in for 3 years.  This is something I’ve grown quite a bit on since, but back then I was terried of being locked down for anything.  I had only spent a couple of days with these guys, and they were asking me to invest money and committ 3 years of my life. What if I didn’t like it?  What if I wasn’t as good as they or I thought I was?  What if I found something better?  Deeper down than the fear of time committment, I knew 2 things:

1.) Howard would make it work.  He would make a big, successful company, and he would do it quickly

2.) I really didn’t want to be part of it.

So I did what I had always done up to that point…I  found a way to ease out the back door.  I talked to one friend, a VC in Columbus, who told me exactly what I wanted to hear at that time (that the deal was not great for me), and I made my decision: I was walking away. I told Howard via email I was not doing the deal.  I do regret that now (not telling him to his face), but that was how I did things back then. But I felt like a freed prisoner and it felt amazing.  I remember walking down broadway thinking to myself, “wow I really do know what I want.”  I guess I was impressed that I was able to look through an opportunity to probably make a lot of money, and do a lot of the things I want to do, and still hear my gut say “it’s not this one.”

Which leads me to tonight..There on the tv before me, with my jaw on the floor, was Howard and Brent (the two co-founders) presenting their newest product offering at the Techcrunch 50 conference. On top of that they were presenting to some people I really admire and would like to meet someday, and quite frankly their demo was VERY impressive.  During the demo Howard let it slip that their current business, the one I was asked to co-found and invest in, will do $20M in revenues this year. I laughed out loud.  I turned to Julie and laughed again, saying “now THAT would have been a good investment.”  I laughed some more and finally said to her “well I was good enough to find an opportunity like that once, and was good enough to know it wasn’t for me, so I’m certainly capable of finding another one that good again.”

And as hard as that may be to believe, I feel that way.  I’m very happy and proud of what Howard and his team have been able to do, and I knew they would do it.  And yes sometimes I wish that I had made better decisions financially in my life.  But as good as that one would have been for my bank account, it would have been worse to ignore my gut. I have no regrets about my decision. And my gut says now if I was good enough to find an opportunity that big once, I can do it again.  But this time it will be right for me.


Tinker don’t perfect


I’ve spoken to several entrepreneurs this week as well as spent some time thinking about my past endeavors, and one thought keeps popping in my head: “tinker, don’t perfect.”   When I look back on some things that I’ve worked on, some of them things I REALLY was  passionate about (have some thoughts about passion, but that’s another post), I realize that a common theme was I was trying to finish them before I started them.  A good example was All is Well.

My basic plan and goal with All is Well was to take an this image that my sister had found after my mom had passed away (to the right) and put it on t-shirts using cafepress, create a simple website to tell the story and sell the shirts, then split the proceeds between the company and several causes my mom cared about.  It quite frankly was a simple


process, one that could have been wrapped up in a week or two.  And I was very close to doing just that…until I had a problem.  The programmer I was working with had basically agreed to put the site together for a very low rate because of the nature of the project.  Unfortunately they got stuck on one issue with cafepress and integrating it within wordpress. Now at this time you could actually buy the t-shirts on cafepress (in fact you still can) but I became obsessed with the site being perfect before I told anyone about it.  So I waited, and waited, and waited, and slowly I realized the programmer had moved on to something else.  The 2 week project became a month long project, which became a 3 month long project, and now a 2 year project.  With each passing day,  I beat myself up more for it not being completed, perfect, and live.  And the more I beat myself up about it, the less time I wanted to spend on it.

Now I will say that there is certainly a whole other layer of issues related to this particular project, and a lot of emotions attached to it, but the point I’m trying to make here is that I was afraid to do anything until I thought it was perfect.  If I had just been willing to accept that perfection, if ever possible, comes with time and tinkering, I most likely would have just gone with what I had, or actually gone with the simplest path to what matters: spreading the message through selling shirts.  So I guess there are 2 lessons I’m seeing here: 1.) tinker, don’t perfect 2.) remember what’s important. What’s the goal?  Don’t get bogged down on all sorts little things that in the end don’t mean all that much to what you’re trying to do.

So whatever you’re working on, give yourself a break.  It is not going to be perfect right away if ever.  But you’re better off playing and sharing and testing, than hiding and perfecting.  Get out there and see what happens.


lessons in failure

I enjoyed Fred Wilson’s post this morning on failure (inspired by Obama’s speech to students a few days ago).  He wrote this, quoting from Obama:

you can’t let your failures define you – you have to let them teach you. You have to let them show you what to do differently next time

He goes on to talk about how when he first started in the VC business, he was so afraid of failure that he worked overly hard to prevent any failures. But  failures were unavoidable in the VC business in 2001 – 2003, and during that time Fred and his firm had a lot of them.  He doesn’t hide from those failures and he doesn’t deny them, he embraces them.

I think embracing failure is one of the things that makes this country such a great place to do business in. In many parts of the world, if you fail once, you are done. People won’t touch you with a ten foot pole. But here in the US, it’s almost a badge of honor. And our President explains why.

We’ve of course heard this all before.  I think most people if you asked them would tell you that they embrace failure and its lessons, but I think what people say and what they feel are very different here.  We all have this fear.

With that said, I do feel so much differently about failure now than I did even a few years ago.  When I look back at my “careerography,” which was written right before I moved to NYC at the end of 2006, my strong fear of failure and my equally strong fear of other’s perceptions of my failures are very evident.  I guess for me the worst part of failing was not so much of what might go wrong, but more so of what others might think of me when things go wrong.  I do feel different now.  That’s not to say I’m not afraid to fail, I still feel that fear.  But I am no longer afraid to openly discuss my failures…in fact as Fred says, I wear them like badges of courage.

Everyone has failures.  What distinguishes us is how we deal with them.


Connect the dots looking back…

Image by

via CrunchBase

I was listening to a Venture Voice with  Scott Heiferman of this morning, and I had a thought about connecting the dots.  When asked how or why he started, he talked about being in NYC in 9/11 and the need for in person interactions inspired him, but the thing that I found interesting was when he went back 10 years to when he first arrived in NYC in 1994.  He said  when he came from Iowa, he looked all over the place for ways to find and meet people in the city who had similar interests.  I think this is how everyone feels when they first move to a new city, but it is clear that this was a problem Heiferman cared about way back then.  He could have never known (or maybe he did) that 7-8 years later (I think) his interest in solving that problem for himself, would lead to  building a platform that would solve it for so many people.  It reminded me of this quote from Steve Jobs Stanford commencement speech:

Again, you can’t connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.

Something about this all makes me excited.  I think it’s something about how the problems you care enough about to seek solutions today, could be the start of something very big.


Building for the long term

Image by jdlasica via Flickr

I’m a big fan.  I think every pair of shoes I currently own came via  Their selection and service are amazing, and they make the shoe buying experience very simple.  But the thing I really love about Zappos (which I know has been discussed to death on the internet), is their company culture.

Today I was listening to an interview (yes, another mixergy interview) with Zappos CEO Tony Hsieh, someone I’ve come to really admire.  In the interview he tells the whole story about the founding of Zappos, how he first got involved as an investor and then later on as CEO, and how the company’s legendary culture evolved.  I realized in listening to Tony talk, the key to their success, one of the key factors in the evolution of their famed culture, was the ability to think and act in the long term.  I think this is one of those things that you always hear (just like following your passion) but very few people have the courage to actually do it.  It’s clear that Hsieh and his team have a long term vision for the company, and they’re willing to allow it to evolve.  The thing about having a long term perspective is you can absorb short term costs such as their legendary $2,000 offer to pay new hires to quit, or their 365 day return policy because over the course of 5 or 10 years those policies will pay off big.  In fact in the interview Hsieh even says he could instantly add to the bottom line by shutting down their 24/7 call center, and most likely it would have very little effect on sales over the course of 6-12 months.  But the worsened customer experience would eventually eat into their most valuable asset (perceived high quality of service), and start to hurt sales.

The more books I read and interviews I listen to about people who do big, remarkable things, and I’d put Hsieh and his team’s work at Zappos in this category, the more I see the importance of thinking and acting with the long term in mind.

check out the mixergy interview


a recap of Tony Hsieh’s talk at SXSW 09


NY Times article on unemployment leading to entrepreneurship

I enjoyed this article in yesterday’s times about people who have become entrepreneurs after losing their jobs in the most recent recession.  I guess this is really unsurprising, and there have been numerous articles about this of late, but it’s always nice to see.  It seems with each new downturn, there is a significant upturn in people turning to entrepreneurship.  There is no cheaper and better time to go out and be an entrepreneur as the cost of starting a business has come down to literally a few hundred bucks (including legal).  Even better is that the costs required to sustain a business have come way down as well, so the hurdle to sustainability is significantly lower for a vast majority of these entrepreneurs.  But something I hadn’t thought of until today…the one huge hurdle that remains, especially for older first time entrepreneurs, is health insurance.  The people mentioned in this article are used to good health care coverage provided by their employers.  As an entrepreneur not only are you on your own in terms of health care coverage, but it is WAY more expensive as an individual or small business.  I have to wonder how many people thought about pursuing a more entrepreneurial path, but had to turn back because of health care coverage.  I think that’s a’s clear to see that encouraging more people to go out and create is good for us all, so lowering and removing the health care hurdle could be a significant stimulus in itself.  (not making a political statement here, just an observation).  There can, should, and will always be hurdles to entrepreneurship.  I just don’t think health care coverage should be one.

Ny Times: Unemployment can lead to Entrepreneurship