She flipped open her sketch book, which looked exactly like a book you would expect a four and a half year old to own. It was ripped in places, bent, crinkled, and completely covered with random splashes of color.

“Here, use this black pen to make the outline. What are you going to draw?”

She had already started creating, a long skinny creature with a beak.

“It’s a duck princess leaving the castle,” she proudly announced. Of course.

My page was still blank. I was stuck. I had absolutely no idea what to put there. Totally empty. I certainly could remember a time where I had the picture in my head, and the excitement of helping it come to life, but here I was with a pen and a blank sheet of paper, and absolutely zero idea on what to put there. I’ll admit there was a part of me that even thought about giving up, just leaving it, and going with a safe scribble of a rainbow. But why? Why was I stuck? There are no rules, there is no judging..from her. I realized there was a filter in me, that was judging, and was slowing me down. Seriously?

Based on this post from James Altucher (one of my favorite blogs), I’ve been taking time, even if just 10 minutes, to have a wide open, anything goes, ideas brainstorming session each day. I’ve been at it for about a week, and I must say it has been far more difficult than I thought. I very much had the same feeling as I did with my niece, staring at a blank piece of paper and no idea where to start. The filter, the judge, was even more active there. But also, quite honestly, I think my “creative” muscle is a bit weak. It’s like I’m trying to do crunches again for the first time in years. The first few weeks are always the hardest, and also the time you most likely want to throw in the towel. I have considered it several times…but have stuck with the practice so far. I’m honestly a bit surprised that this muscle is weak. I would have thought all the work I’ve done over the years, certainly would have kept me sharp. I must admit, it’s weak. But it’s getting stronger. It takes time and practice.

Ultimately, I just dove in. She had a duck princess, and I had to deliver something. A frog came to mind, so I drew it. It came out deformed with a confused arrangement of legs and arms. I found myself saying out loud “whoa, that’s bad,” but kept at it. After a few minutes, she looked up from the Duck princess and said:

“Wow, Uncle Dan, that’s a great Frog!” Ha…she was right, what a great teacher.

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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.

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.

It gets really, really hot in NYC in the summer, particularly in July and August.  It’s the kind of hot where you’re sweating the moment you open the door, and all you want to do is stay inside in the A/C.  I really feel for those who have to head out everyday in this heat wearing a suit, and I really feel for those who have to wear a suit everyday AND ride the subway.  The subway stations are literally like an oven this time of year.  Ugh.  I’ve been fortunate to work generally in a “virtual” environment, and don’t really have to ever dress up except for a few meetings here and there.  But despite this freedom, I have continually worn jeans and a nice shirt when I head out during the week.  It’s one of my rules (I’ve written many times about my rules.), and I finally broke it this summer (without even noticing it until today).

We all have rules, some of them make a lot of sense, and some are just bizarre.  Forcing myself to wear jeans when it’s 90 and 80% humidity is a stupid rule (note: if you’re one of those people who just likes to dress up to feel good, then go for it).  Why did I do it?  Because I wanted to convince myself and others (who don’t really care) that I was indeed a working professional, not just some bum with a computer.  Why?  I don’t really know, but it was one of those things I didn’t even notice I was living by until someone pointed it out to me one day. It’s hard to notice the rules we hold ourselves too, but we all have them.  The key is figuring out which ones need to be broken.

Today as I was walking in the scorching NYC streets, I was thankful to be in my shorts.  I feel for those poor people that make themselves wear pants in the summer.

Well it’s official, or at least it feels that way. I don’t think we’re going to ever sell the GJG directly to users profitably. It doesn’t mean that GJG is a flawed concept, it just means that Chris and I are unable to sell it effectively with our approach. And we’re just sick of trying to sell it. So how do you know whether you need to work through something or you need to cut your losses? In other words how do you know when something is a good hitter in a slump or just a bad hitter. The good news is there are lots of lessons in this experiment that I can take with me into the future…lessons that can only help me on my entrepreneurial path.

10 lessons

1. Don’t ever do something primarily to make money quickly. It will take way more time, money, and effort to get something going than you could ever think, no matter how quick and easy it appears. So if you have no interest in the particular subject you think you can make money working on, then don’t go anywhere near it.

2. (building on the last one)…Being an entrepreneur requires passion. It sounds cliched but if you took money out of the equation, would you work on whatever it is you’re working on? If the answer is no, then you need to re-evaluate.

3. Just because something seems like a good idea, and it’s based on very sound assumptions, it does not mean it’s a good idea for you to work on. We really nailed the economic trends that could have put GJG at the front of rising tide (the search numbers have tripled since we started), but that was not enough to make it work for us. Tying in with the 2 points above, you need more than just a good idea to make something work.

4. Get in front of your business and your customers as soon as possible. We hid for nearly 6 months with GJG. We hoped that it would somehow work and come together without us really ever getting out and talking to other people and even more importantly our potential customers. This again goes back into 1 and 2 because we weren’t really that interested in the subject, we were just hoping it would make us money. We learned more about the business and our potential customers in 3 days of phone calls than we had learned in 6 months of researching, reading, and testing. Get in front of people (customers, other entrepreneurs, potential investors, partners, friends) on an idea ASAP. And going with the lesson learned in 1 and 2, the more excited and passionate you are about something, the more excited you’ll be about telling the world. I guess a good rule of thumb is, if you wouldn’t want your face and name next to an article about your business in the New York Times, then it’s probably time to re-evaluate.

5. Talking and brainstorming are very important in entrepreneurship, and time must be made for them. It’s way too easy to get swept into each day’s activities and completely push off the big picture discussions. In GJG we kept talking about having big idea discussions, but only had a few over the course of 6 months. Make time for connecting, talking, brainstorming around your business. It energizes, and strengthens the long term picture, which provides a backbone for the day to day…thus helping you ride out more of the ups and downs.

6. Planning is important, especially in times of uncertainty. We struggled to really consistently make plans that went beyond a few days with GJG, so we were always sort of scrambling based on the data of the last 3 hours. It’s very important to lay out a plan that is specific and easy to follow, and that has clear success metrics, deadlines, and decision points. We always went on with GJG with the notion that we were just one or two changes away from making it work. If we had been more serious about keeping a plan, with deadlines, milestones, and success metrics we may have pulled the plug or switched directions earlier. By following a moving target, we struggled to really make clear decisions. This again ties in with 1-2.

7. A partnership is built on open communication. With GJG we started early on with a company email list where open discussions where encouraged. These discussions were not just about GJG, but about life, entrepreneurship, personal development, and especially ways to communicate between partners. It certainly allowed for issues between partners to get out while they were relatively small, and so they were discussed and worked out before blowing way up. A partnership is very much like a romantic relationship. Without open communication and a mechanism to get out frustrations, they will never succeed. It’s hard enough being an entrepreneur, much less an entrepreneur by yourself facing off against your partner. If you can’t discuss your dreams and your FEARS with your partner, then you need to find someone else to work with.

8. Don’t try to create and sell a product you wouldn’t buy. This is very similar to 1 and 2, but important enough to state separately. It’s hard enough to create and sell something, much less something that you don’t really care about (no matter how much sense it makes). GJG is not a product I would have ever bought. Even in the outside chance I may have looked for a product like that, I would have NEVER bought it in the manner we were selling it. That disconnect had to show in the product and the marketing, and certainly had to hurt our chances. Entrepreneurship is about creating something that solves a problem and then scaling it. The best way to understand the problem you want to solve is to have it or live it. So if you’re creating something that you solves a problem you don’t have or understand and you would never buy or use it, then you need to re-evaluate a bit.

9. waiting doesn’t feel good. We had tons of waiting scenarios with GJG, whether it was waiting on a programmer to do something, or for people to come to the site, or for people to buy, we had a lot of moments where we sat and watched our inboxes and analytics accounts. Watching and waiting does not feel good, and it does not help your business. It drains you, and it distracts you. Both of these things fulfill a need to feel like you’re working, but neither of them help you make progress. I guess it’s more likely that you’ll stare at these two things if you’re not crazy about your product, your customer, amd the subject matter. But waiting is more than just watching these two things. It’s waiting on an email when a phone call could get the answer now. It’s waiting on one person, when others could potentially help you.

10. Ask for help, early and often.  We did get good about reaching out to others for help along the way, but it took us several months to get there.  People really do want to help, so go out and ask them for it.  If you feel like there are certain people you can’t ask for help because of what you’re working on, then you need to see number 8 above.

So while I’m not happy about the money and time lost in the GJG experiment, I don’t have any regrets because of the many lessons I learned along the way.  I guess the hardest lesson, and one that I didn’t put above, was knowing when to quit.  We probably went way too far into this process because we convinced ourselves this was our only and best option.  It wasn’t until a moment of just intense frustration this week where we realized it was time to make a big direction change.  I can’t say I really have a good idea when it’s time to switch directions other than you can just feel it.  Oh well, on to the next thing…

This post was inspired by this Post in July of 2008

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