Anxiety

Published on February 8, 2010 in business and personal. Comments Tags: , , , .
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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…

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2009 to 2010 thoughts

Published on January 1, 2010 in personal. Closed Tags: , , , .
Bright Idea
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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….

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Op-Ed Columnist – The New Untouchables – NYTimes.com

Published on December 21, 2009 in personal. Closed
Those who are waiting for this recession to end so someone can again hand them work could have a long wait. Those with the imagination to make themselves untouchables — to invent smarter ways to do old jobs, energy-saving ways to provide new services, new ways to attract old customers or new ways to combine existing technologies — will thrive. Therefore, we not only need a higher percentage of our kids graduating from high school and college — more education — but we need more of them with the right education.

via nytimes.com

I forgot about this piece from Thomas Friedman from back in October. I can feel this new creative, entrepreneurial class really starting to kick into gear around me. It’s not an age or race thing, it’s a state of mind. It just feels like more people are going out on their own to create progress in the world. That’s of course a very good thing.

Posted via web from Dan’s Random Stuff

JFDI

Published on December 2, 2009 in personal. Closed
Jordan XI
Image by makoworks via Flickr

I stumbled on to this great blog post by @msuster talking about what it takes to be an entrepreneur.  His post can be summarized in four letters, JFDI, which stands for Just F**King Do It.

Entrepreneurs make fast decisions and move forward knowing that at best 70% of their decisions are going to be right.  They move the ball forward every day.  They are quick to spot their mistakes and correct.  Good entrepreneurs can admit when their course of action was wrong and learn from it.  Good entrepreneurs are wrong often.  If you’re not then you’re not trying hard enough.  Good entrepreneurs have a penchant for doing vs. over-analyzing.  (obviously don’t read this as zero analysis)

This really resonated with me.  I can get very comfortable with analyzing things.  I can in fact spend months and years analyzing something.  This is partly because I like to research, explore, review, brainstorm and partly because I’m scared of moving forward.  Sometimes I tell myself I’m just afraid of making the wrong move, but either way it’s all related to a fear of taking the next step.  The problem with this is you end up in this limbo world where you are safe from mistakes but also tormented by the decision hanging above you.  The longer the decision hangs above you, the heavier it gets whether you are aware of it or not.  The only reprieve from the weight is to act.  JFDI

In the blog post he talks about an entrepreneur who was constantly in brainstorming mode on his next thing, saying he was stuck because he didn’t have any money.  He was convinced the only way forward was to raise money.  This is a common excuse for inaction among entrepreneurs.  I’ve certainly been guilty of this, although I must confess my preferred stall tactic is to tell myself and others that I don’t quite have the right idea yet.  It doesn’t really matter the reason because at the end of the day they are just excuses. This is one of many deciding moments in the life an entrepreneur, the place where it seems like you are all out of options.  Either you find a way to do it, or you quit.  Mark advises the stalled entrepreneur:

I was blunt (warning: that sometimes happens with me) and told him not to bother and that I wasn’t prepared to help with angels.“Why?” he asked.  I told him he wasn’t a real entrepreneur.  He looked stunned.  I said that he had been talking about doing this for too long.  He still had no website and no prototypes.  But “he didn’t have the budget to hire a developer until he had raised money!”

I said that was my point. “A real entrepreneur would have done it anyway.  He would have found somebody technical and inspired that individual to work for equity or deferred payment.  Real entrepreneurs are contagious.  They are filled with ideas and they get those ideas onto paper.  That paper can be in the form of wireframes or in the form of a PowerPoint plan.  Or worst case your ideas can be conveyed verbally.  But they GET THINGS DONE.  You have the skills and knowledge to do that.”

Blunt but great advice.  If you want something bad enough, you can find a way to move forward, to act.  If you’re focused on the acting towards a result instead of a step towards a result (getting a prototype built some way vs obsessing over raising money to get a prototype built), if you’d JFDI, it would come together some way.  The entrepreneur took his advice:

He took my comments as a challenge.  He went out and found a developer and built a product.  He refined his business plan and he got commitments for $150-200k but needed some lead angels to commit first.  When he re-approached me he had a much better plan and he had a prototype!  I introduced him to some angels and his round was OVER SUBSCRIBED!

You and I have all the knowledge and skills we need to move our businesses forward RIGHT now.  We don’t have to wait for more data, for someone else to help, for outside input, for the “right moment.”  None of that.  We can move things forward right now. JFDI and you’ll not only feel better, you’ll be amazed at what you can accomplish.

(Additional thought:  I think self reflection, analysis, outside input, etc are still very important and should be used with the JFDI approach.  I think a good analogy is practice vs real game in the sports world.  There is definitely a time and place to practice and develop your skills, to analyze, to grow and then there is a time and place where you just trust and act.  Get out of your head at the real game and trust your training and preparation will guide you in the right direction)

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How far are you willing to go?

Published on December 1, 2009 in business, future and personal. Closed Tags: , .
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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 at least 5 different 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?

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What Does It Take To Be A Successful Entrepreneur? – with Jerry Colonna

Published on November 24, 2009 in personal. Comments
via mixergy.com

Jerry is just an awesome dude who I have the pleasure of learning from and working with on a regular basis. I’ve learned so much from him both in life and in business, and as a big fan of Mixergy I recommended both Jerry and Andrew do this interview. It really turned out great, definitely check this one out when you have a chance…

Posted via web from Dan’s Random Stuff

Culture and Core Values (via OrganizedWisdom)

Published on October 14, 2009 in personal. Closed

I really liked this post from Unity over at the OrganizedWisdom Blog on their company values and culture.

I’ve been fortunate to spend some time with the guys at OrganizedWisdom and I know that they truly mean every word posted.  I’ve learned more and more that the key to a successful startup is a solid foundation of people and values.  I think people often get confused that ideas, connections, or money are the key to success.  From what I’ve seen, all of those things help but are not the key.  In fact I think all of those things are easier to come by when you have a solid core of values and people who believe in them.  I really like the core values laid out in the OrganizedWisdom blog post:

So here are the 10 core values that shape our culture…

  1. Our people are our most valuable asset and our most important investment:
    Over 90% of our budget is invested directly in our team! It is ultimately our team who drive innovation and create success.
  2. We only hire A-team players who are the best at what they do:
    We care as much about passion and a positive attitude as we do specific skills and experience.  We strive for a family spirit to create a fertile environment for service, progress and growth.
  3. We dream big:
    We believe (and have proven since inception) that any goal we set for the Company, we achieve. We set big goals and constantly ask how can we do better, how can we innovate, and how can we help more people?
  4. We focus on effectiveness and results:
    We work with each team member to define clear and measurable goals every month and use weekly metric reviews to stay focused and keep on track.
  5. We believe transparency and collaborative communication makes us more effective:
    We get more done when working together which is why we use group communication tools for nearly everything we do.
  6. We stay solutions focused when innovating:
    The mindset is not why we can’t do something, but how we can do something.
  7. We don’t write plans, we mock our ideas.
    On the fly prototyping enables us to innovate rapidly, save valuable time, and get new creations live early and often so we can get invaluable real world feedback.
  8. We continually test, experiment and optimize:
    Our product and the service we are creating are never done.  We use data and real-world feedback and iterate producing major transformations of the week.
  9. We thrive because of our $0 Cost Office Model:
    Our going green virtually approach helps us do more with less, create happier team members, and invest our time and capital more effectively to better serve our users and our clients.
  10. We’re passionate about an important mission — to create the most useful search service in online health…We hope those around us are inspired by our energy and passion for the OrganizedWisdom Mission to help people.

Check out the full post at the OrganizedWisdom blog.

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“Make meaning not movement”

Published on October 7, 2009 in business and personal. Closed

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.

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Note to future self (and others): I will make lots of mistakes

Published on September 17, 2009 in future and personal. Comments Tags: , , , , .
The old road on the southern side of the St.
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I had one of my favorite mixergy interviews with Zaadz founder, Brian Johnson on in the background today while doing some work.  Brian is my kind of entrepreneur, a guy who has seemed to have found the amazing intersection of personal meaning and business.   There’s a ton of great stuff in this interview, things I will most likely write about down the road, but there was one thing in particular that struck me.  Brian says he’s learning to embrace the fact that he is an entrepreneur, a creator and with the lifestyle comes mistakes. Lots of them. There is no avoiding them or denying them, they will come sooner or later.  So as he’s embraced who he is, he’s also learning to embrace the falling down and the more comfortable he gets in the falling down, the less he fears it.  I want to embrace it too.

So I guess this blog post is a first step there.  As I’ve discussed before, I struggle as much if not more with the fear of what others will think of me after a mistake as the consequences of the mistake itself.  So let’s just get this out of the way now: For anyone working with me or anyone who may work with me in the near or distant future, I’m going to make mistakes.  In fact I  may make a lot mistakes, but I will get up and move on from each one a little bit smarter. I’m telling you now, so it will be even easier to tell you later. I will do my best to deal with whatever the consequences of the mistakes may be. I’ll do all I can to learn from them and move forward.

There, now that we have that out of the way, let’s get on with the doing…

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no regrets about going with my gut.

Published on September 14, 2009 in business, nyc, personal and tech. Comments Tags: , , , , .
Scoring a Stash

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.

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