Tag Archive | nyc

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.


Talk About It

It’s definitely been an interesting 2 months or so for me.  In addition to traveling a lot for weddings and a vacation, moving into a new (and better, much better) apartment, I’ve seen a lot professionally as well.  Coming off of my so called “failed entrepreneurial experiment,” I really struggled for a little while in terms of where I was headed professionally, which affected my life overall.  I really let the fear of the uncertainty get to me, so much in a way it was having an effect on my business partnership, friendships, and most importantly my relationship with Julie.  Now 2 months later I feel like I’m in a totally different place..the secret? Talking about it.

It sort of sounds like something you’d expect to hear on Oprah, but it has definitely been true for me.  In the past I always believed that the whole reason you talked about something was to find a solution.  It turns out that this is not the right perspective.  When you’re talking just to seek a solution your conversations are forced and usually focused inward.  It’s really hard to hear what the other person is saying when you’re thinking about what you need to fix.  Thankfully my friend Jerry has been telling me for awhile now that 1.) I needed to communicate more in my relationships (talk about it) 2.) the purpose of talking is not to solve but to connect.  So when it really felt like my business partnership was on the verge of breaking apart, and I found myself talking less and less to my partner Chris, I was reminded of this lesson.  Chris and I had several very long conversations where we discussed our lives both professionally and personally.  We didn’t find any long term solutions, but we felt much better.

This is even more true in my relationship with my girlfriend Julie.  When Julie and I get busy, and we stop communicating normally, and then we are faced with a stressful situation things usually reach a breaking point.  Earlier this summer as I was dealing with the stress of the above, and Julie was working nights, and we weren’t communicating normally, and we both were having our fears about the future, things came to a head.  As I’ve said before, relationships require effort, and I had been distracted from putting in the effort…so we talked about it, a lot.  I feel closer and more connected with her than I ever have I think. We both do. Did we solve everything? No, of course not.  But talking about it makes us both feel better, and feel better together, and feeling good with a little time will bring the solutions as well.  Talk to learn, explore, connect, and communicate..don’t talk to find solutions.  The solutions will come.


Opportunities in the moment


Image via Wikipedia

I’ve been meaning to write something on Fred Wilson‘s post last week on job losses here in the US, noting that the announcement last week of 75,000 jobs being wiped out in one day exceeded the amount of jobs he had helped create in 22 years of venture investing. Wow.   He goes on to say that we need people going out on their own to help us get through this.  I agree.

I think going out on your own can mean a lot of things, and doesn’t necessarily being an entrepreneur as most people think.  You don’t have to know how to build a business or raise money or hire people, you have to know how to capitalize on your unique skills and abilities.  You have to know how to find opportunities that exist right now in your life, all around you.  I really liked this comment on Fred’s post elaborates on this better than I can:

An anecdote to illustrate the point of the awakening of entrepreneurial impulses in the population: a cab driver that took me to SFO airport from a recent JP Morgan Healthcare conference told me that he has been asking himself, what can he do better in this grim environment. His decision was to focus on nurturing and growing his local clientele, to increase their loyalty to him, and to bypass convention traffic, as it would not mean return business. – Now if everyone from cabbies to white collar folks is asking, what can they do better and how, wouldn’t that necessarily lead to a bump in productivity, perhaps an unexpectedly meaningful one? I hope so. Same for previous non-entrepreneurs becoming entrepreneurs – in some sense, it is a numbers game – if enough of them build highly scalable, fast growing businesses, VC-backed or bootstrapped, it might have a strong enough effect to at least dampen the fall we are in. I choose to remain a long-term optimist, if wounded at present.

I’ve been saying for a few years now that I think more and more people will eventually beome their own mini companies and create a world where we are more likely to be sole proprietors than employees.  I think it’s  likely that people will work on “projects” instead of working for companies in the near future.  Think I’m crazy? This process has already started.  You can see it on sites like elance.com, odesk.com, 99designs.com and many, many more.  These sites are filled with very talented people who are building thriving businesses (some one man shops, some have several people) focused on doing what they do best, whether that be design, programming, sales, or whatever. Now these sites are by no means perfect, and they certainly are not capable of having a major effect on the economy at the moment, but I think they could be a starting point for something that may.

I can’t help but think of all the amazingly talented, smart, hard working people out there who are not working at the moment.  To quote a friend that’s an “incredible waste of national resources.”  People are not losing their jobs because there is no work to do, in fact there is more work to be done now, it’s just that no one has figured out how to tap those resources.  Isn’t there an answer in the elances of the world? If we could figure out how to tap the incredible worldwide design talent by using a marketplace like elance,  can’t we expand that to put some of these people to work?  Doing something they are good at (and most likely enjoy)? Just a bit of rambling…


Why are you scared?


(See, she’s harmless)

As the proud new owner of a puppy (she’s about a year, so technically still a puppy, but almost full grown) in New York City, I’ve become quite good at reading people and instantly identifying dog people and non-dog people. Dog people generally look down at her as we approach them with a smile or at least a happy expression. Some of them can’t help themselves from bending over and petting her as she jumps up and down with excitement. I am pleasantly surprised at just how many dog people there are and love running into them as I walk her. But as much as I’m surprised by the dog people, I’m even more surprised at how many non-dog people there are. The non-dog people are easy to spot. They notice her from a good distance, and usually fold their arms close to their chest, stare at her with a glaze of fear in their eyes, and make their way quickly to the very edge of the sidewalk as if they are skimming by a werewolf on a leash. Most of them just seem absolutely terrified to even be on the same block much less same chunk of sidewalk as her. I really have to wonder: Why? Why are they so afraid of her (and dogs in general)? Were they bitten in the past? Did their friend have a mean dog that would chase them as a kid? Were their parents afraid of dogs, and they learned from watching them? Why were they so afraid of this sweet, loving, absolutely harmless and friendly animal (referring to my dog)?

I’m fascinated with the human mind/body at work here. Obviously this fear is an individual thing because not everyone is afraid of dogs, and not everyone loves them, but what separates the two? What happened in the past to create a fearful non-dog person? Ok, perhaps they were bitten by one in their distant past, and there I could understand why they were afraid of THAT dog, but why all dogs? It makes me wonder about how our mind works. Perhaps in the process of analyzing and storing so much information, our brain takes an awful lot of shortcuts. It knows that at some point in the past being around a dog brought pain, and avoiding pain is generally a necessity for survival, so it quickly calculates that dogs = pain, and to stay away from them. But we all know that not ALL dogs are evil and mean, and therefore assuming they all will bring pain is false, so why then do some still avoid them at all costs? I think because it’s a wired pattern in the brain…dogs=pain, avoid at all costs. I am not afraid of dogs, but I am sure afraid of other things. Do I act the same towards those?

I have to wonder: What are some things I learned in the past that could bring pain, and now have almost an instinctual reaction to avoid? I believe one of my “dogs,” has to do with acceptance of others. I learned sometime ago that sticking out too much, going against the grain of others too much publicly could bring a lot of ridicule, and ridicule was painful. Looking back on my early years, I can recall quite a few instances in school where I stuck my neck out and was quickly brought down by those around me. That was my “dog bite,” incident and now I have a reaction whenever I feel I’m in a similar situation I pull my arms to my chest and rush to the edge of the sidewalk. Deep down I feel that most circumstances I expose my strongest thoughts and beliefs in are dangerous. I never really thought about it before because I didn’t have to. My body reacted for me, working quickly to secure me from the potentially dangerous situation. But that doesn’t serve me anymore. I’m not a 3rd grader trying to fit in with my peers, I’m just trying to be all me in this world…and I don’t care what everyone thinks. After all, I KNOW 97% of “dogs” won’t bite. It’s time to stop avoiding them.

Project to lifestyle


(“Learning to Swim,” on flickr by sposta via CC – You can’t learn to swim until you jump in)

I feel like everyone I speak to these days has at least a “project or two,” they are working on. By project I mean they have something they are at least thinking about that hopefully could someday become a real working business that they would own and operate. At the moment, I certainly consider myself part of this group, and sometimes it’s really sort of depressing. I know so many of these “projects,” will never even see the light of day, and of those that do even fewer will ever get far enough to be considered a business. This seemingly harsh reality begs the internal question “Why am I any different?”

I think that more and more people from my generation are at least thinking about heading down the entrepreneurial path. The so called millenials have grown up with access to unlimited information across an unlimited spectrum of niches. We’ve been empowered to go out and learn about anything and everything we’re interested in with ease. We’ve also had front row seats to rise of the “young entrepreneur.” We’ve heard so much about people out of high school and college creating companies that are phenomenal successes. We idolize these people yet we also can’t help but ask “why not me?” This question is precisely why we are so fascinated with them. I’ve asked myself that question for at least 10 years now, going way back to my high school days where I became obsessed with the business world via the stock market (dotcom days, ah what a time to start investing!). Why couldn’t I potentially take my part in the American dream? It’s cheaper than ever to start a business. All the information, contacts, and products you may need are seconds away in a Google search. From the outside perspective the only thing that stands between you and your dream life/job is a smart programming partner and a few months (NOTE: most of the people I talk to are trying to create some sort of web focused business, so they need someone with programming skills). And that is why I think there are so many of us out there with projects.

But if projects are so easy to start, why aren’t more projects becoming working, real life businesses? Because I think very few project starters have the capability to start a business. Most of us want to learn to swim by merely dipping our toes in the water. We think we can expose ourself to gain without risking any of the potential failure, but the truth is the lessons from failure are what create opportunity for success. If you don’t attempt to swim by getting in the pool, you’ll never feel the struggle that is growth, the struggle that is learning. And very few people are prepared for a struggle.

I find comfort in that. Don’t get me wrong, I love the explosion in entrepreneurial mindset in this city and this country. I love that at least in our heads more and more us believe we are capable of doing something big on our own. We all benefit from this because the tinkering of potential entrepreneurs and current entrepreneurs is what pushes growth and innovation throughout. This constant push to create is what created the great environment we are in today. But now I’m seeing what separates someone building a project and someone building a company, and I have to really respect and admire the courage in the creators. Great things happen to those of us who are willing to put ourselves out there. I mean to really put yourself out there for something you believe in. “Putting yourself out there,” obviously has different meanings for different people, and you know ultimately what that means for you, but this is the only place where your “project” becomes a potential business.

For me I believe this means to stop hiding in confusion (I’m not quite sure what to work on),pick a path, and declare it to the world. For me putting myself out there isn’t about money because I’ve never been afraid to put money on the line (thanks to my days dotcom investing and bootstrapping a business in college by the nifty credit card balance transfer trick). My “putting myself out there,” is more about exposing myself completely to the criticism of others. I get out there by speaking up with my ideas, sharing them with as many people as I can, reaching to any and all who may be able to help, and learning from the feedback. Only by challenging myself to expose ideas to others, with a firm voice behind it, can I learn to swim (that’s part of the reason I’ve been blogging more lately..it’s amazing how much more you can write when you write what you’re truly thinking / feeling) and move my project on to a company.

How do you put yourself out there?

Life Tip: Don’t worry about what other people think…

I have a new dog (puppy really, she’s about a year) and she’s great.


Anyway there are a lot of dogs in my building and it’s been great talking with my neighbors as we all head out on our morning and evening walks.  I never realized how great a connector dogs can be.  I’ve talked to more people in the last 2 weeks than I probably did in the last 6 months.  But they haven’t all been good conversations.

Yesterday evening while heading out for my night time walk, I held the door to the entrance of my building for an older woman who is a resident (I had never seen her before though).  While stretching to hold the door for her and control the dog, Izzy (the dog) decided to relieve herself in my building lobby instead of outside.  The woman saw this and seemed to be ok with it, sort of looking disgusted but laughing.  I apologized and told her I would clean it up. No big deal.

Today around the same time I took Izzy for her evening walk.  Again on my way out the front door one of my older building residents, who is in a wheelchair, was at the door.  I again stretched to hold the door open for him, and again Izzy relieved herself at the door, although this time outside on the sidewalk directly in front of my building.  As I stood there and talked a minute with my neighbor in the wheelchair, the older woman from last night came home.  While opening the door she talked very loudly to herself (indirectly aimed at me)…”this is ridiculous, he can’t even control his dog…first inside yesterday and now he lets her pee on the door today. Just ridiculous.  Give me a break!”  I tried to explain but she was in the door, and I was pissed.  And embarrassed.

How come this bothered me so much?  It was an accident.  I’m as considerate as any other resident in this building.  I’m clean, I’ll even clean trash in the lobby that is not mine.  I don’t steal papers, I’m courteous, and I have very good dog manners.  I didn’t intentionally let this dog pee near the door.  It was an accident of circumstance.  Why did this seem to bother me so much?

If you are someone who cares a lot what others think, this city will be tough for you.  There are so many people with so many crazy rules and life regulations (as my friend Jerry would say they are all carrying around “their own bag of shit.”), you are bound to, at one point, rub someone the wrong way.  That’s just how it works.  So if you let yourself get all whacked out of sorts by all the comments and opinions of others,  you’ll lose your mind.  It’s a lesson for life we learn early: “sticks and stones….words will never hurt me.”  So true.  All you can do is live by the rules that feel right to you, don’t worry about breaking the rules of everyone else.

I’m good, really

It seems like everytime I post to this blog I start off with an apology for not posting in awhile and while I’m tempted to do the same here, I won’t…


Things have been great. I’ve moved into a nice new apartment on e. 17th st. just a short walk from Union Square, which I’m very excited and happy to be in. I’m even more excited to be finished with the whole New York City apartment search and moving process which quite frankly, is horrible. It’s painful, expensive, and draining becaues everyone you come in contact with immediately demands to know what they can get out of you. I guess in a place with limited supply and endless demand, being nice and having good customer service is not required to be successful. Unfortunately this has been true from the apartment brokers we worked with to the new build Super (wow is he a not nice person), and even the new building management. It seems the name of the game is to get the most money as quickly and easily as possible. This means getting people in the door and signed on the dotted line. After that, who cares what they think or say.

With all that said, I’m happy with the new place. I love this city. The energy, the endless stream of diversity and interesting sites. I love the possibilties. I love my apartment. I look forward to a new and exciting experience here.