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…

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…

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.

Ny Times: Unemployment can lead to Entrepreneurship

I feel like this is a question I’m constantly asking,  and perhaps that is part of the issue, but I feel like I’m really at decision point on what to do next.  As I touched on in this post, I had a big project I was working on come to an end in May / June and since then I’ve been thinking a lot about the question: “what to do next?”  Now don’t get me wrong, my current situation is actually very good.  I’ve got a very good consulting gig working on a startup that is not short on energy, excitement, or capital.  It’s been fun to work with people who really passionate about what they’re doing, and it’s been nice to not worry about paying my bills.  It has been a great summer experience, and at the very least I’ve helped get an interesting concept off the ground and assist another entrepreneur in pursuing his dream, all while putting a little money in my pocket (I’ll share concept when it is live).  That’s a good thing, but truth be told I know that this is only another project for me. I know that 6 months from now I’d like to be back on my own, pursuing a concept, industry, niche I feel more personally connected to.

I know I’ve talked much about finding a purpose and pursuing a passion, but I’ve backed off that a bit.  There is something very heavy in telling yourself that you must find and work on your passion, your calling.  Especially when you’re like me, and you are interested and excited about all sorts of things.  How do you pick one thing when you have ten that seem interesting in front of you?  Add to that the weight of picking the one that is your purpose, and you end up stuck…as I have been many times before.  I will say though, I don’t really feel stuck at the moment.  I’m moving forward and picking up skills and connections that will help me down the road, but I still am in the same position of not knowing exactly what road I want to at least try and go down.  Simply put: I’m not sure what to do next.  I don’t want to carry all that pressure of finding my calling, and I don’t want to just go with the flow like a stick in the stream.  I want to go forward with something that is especially interesting to me, something that feels good, but I am not worried about it being “it.”  I just want to feel close personally to what I’m working on (I will not make the mistake again of investing time, energy, and money into something that I don’t care about, no matter how good of an idea it seems).

I do consider myself very lucky to still be in a position in my life where I can seriously ask this question, and at least feel like I’m in a position to pursue the answer.  My responsibilities are fairly light, and I’ve been at this long enough to have a good group of people around me who support whatever I want to do.  I look at the world and honestly feel that I could do anything.  I’ve always felt that way.  Or maybe deep down I don’t.  Maybe that is why I can never seem to answer that question because if I don’t answer it, then I don’t have to do it. OK now I’m just making things complicated.

Man this post seems like a giant circle, perhaps that is part of the issue here.  I think part of my answering this question is to write more.  I want to write here more.  I think I want to list things I know I don’t like / want.   I want to go back and explore my past writings, maybe even update my careerography, reach out to more people I admire, but what else?

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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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I’ve been thinking and wondering a lot lately about what needs to come together to create a working company.  I’m not going to touch the issue of “successful,” company because that’s really impossible to quantify (at least for me), so instead I’m just going to look at what I think is needed to make a “working” company, defined as one that is growing, can meet all of its financial obligations, and support the entrepreneurs behind it.  As best as I can see it there are 4 inputs required to create a working company (all either provided or gathered  by the entrepreneur):

1. time
2. expertise (includes a network of contacts)
3. money
4. energy / passion
5. **Luck

I struggled with putting energy and passion in this list because I think it is more important than any of those items, and it influences them all.  The odds are (and we always hear about this) the more passionate you are about what you’re working on, the more leverage you’ll have on everything else (time, money, expertise).  If you’re passionate, you will find a way to get all of those ingredients together.  In fact I would say that number 4 is more of the wildcard here.  It can make up for a huge defiency in any of the other items or all.  I guess you could call passion/energy the leverage.  It helps you do more with less.

All of these are needed in some amount to get a company going.   If you’re extremely strong in one area you can make up for a weakness in other areas.  For example if you’re expert in building and managing sales teams, and your new business is in sales of some kind, it will likely take less time, money, and energy on your part to get things up and running.  If you don’t have any money, and you don’t have any expertise in the space you are hoping to work in, then you’ll need to devote a lot more time (and I hope you have the passion to drive you through it). I added luck with a star because I think all companies need it.  The problem is you can’t really plan on good luck, you can only increase your odds of getting it through time.  The more time you’re able to buy yourself and your business, the more likely you’ll have some luck on your side.

I’m sure a lot of people will wonder where idea fits in all of this.  I”m learning that idea in most cases is not all that important.  It can really help people be excited about what they are working on, but I think mission can do more for making someone passionate.  The idea itself is usually just a starting point, a place to organize resources.  Rarely will the idea you start with be the one that works.  They usually evolve very quickly as more time, money, and expertise are added.

I’d say in my current situation I’m capable of providing some expertise, some money, and some energy…but my best contribution is my time.  Sometimes that really can be frustrating.  Without expertise or money to push things forward, you just need the time to experiment (and make a lot of mistakes). When setting out to start a business, take a look at the list above.  What, at the moment, are you most capable of bringing to the table?  Are you OK with that?  Can you really give all that is required (especially in $$ or time)?

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It’s not that I stopped writing blog posts, it’s just that I stopped posting them here.  I find that I’m constantly writing out thoughts, but I struggle consistently posting them here.  Instead I usually will email them to a few different people to get feedback.  I realized today that I could simply edit those emails and start posting them here.  So the 3 of you that still check my blog…I”m back.

My partner Chris and I have been having some long discussions lately about working more efficiently (more work in less time).  He has been inspired by the 4 hour workweek (which I read a little over a year ago).   I think there are a lot of great thoughts in that book, but I really don’t think it’s likely you can start a successful business following all of his guidelines.  Chris and I have been back and forth on this.  Here is my latest email on the topic (sorry if it is a little jumbled).

I’ve been thinking about this,the slippery slope of trying to work super efficiently.  I’ll admit it is a struggle for me.  On one hand I get very excited about the idea of “getting 8 hours of work completed in 4 hours,” and I think striving to do that could really make some interesting things happen like better delegation / outsourcing skills, and being more relaxed.  But on the other hand I’ve been racking my brain thinking about “successful” entrepreneurs I know. By successful I mean those who have built a business that more than pays their bills, they have a great team around them, and lots of upside potential.  Some of these people I’ve known for awhile, others I met recently…but one thing I know for sure: they are all VERY active.  I realize that the 4 hour workweek is not about only working 4 hours a week, but really about delegating and confronting simple tasks as quickly and efficiently as possible.  Part of this approach is really about attacking email, encouraging people to cut down significantly on the time they spent writing and responding to emails.  I agree 100% here.  I think email must be controlled or it will control you.  But I think other things in the 4hww are just not practical for entrepreneurs.

Building a business to me seems a lot like building and maintaining physical fitness.  They are actually very similar…as most people want to be “fit,” but very few people (myself included) really do everything it takes to be fit.  When it comes to working efficiently vs not working there are parallels as well. There’s no doubt that you can truly “get a body like this with just 30 minutes of exercise, 3 times a week,” as they say in those Bowflex commercials.  The problem is very, very, few people work themselves hard enough in those 30 minutes for that to be true.  Even worse the way that is written I think most people assume then that exercising and getting fit should be easy, so they slack off even more, cutting their sessions to 2 times a week, then 1, then it’s a piece of crap in your basement.  They also get pissed and annoyed that they are not fit, despite doing what the commercial said.

I think the Tim Ferris mantra is like the 30 minute quote above.  It is absolutely possible to build a successful business with just 4 hours of work a week, or 4 hours of work a day.  The problem is that most people don’t know enough about entrepreneurship and/or their business to really effectively use those 4 hours of work a week / a day.  So if they do truly just work the 4 hours a day  / week, they don’t get enough finished to really make the business work, and it becomes a piece of crap in your basement.

I completely agree that most people (myself included) simply do not work efficiently, and don’t delegate properly.  But like exercising, you really can’t know what are key exercises to do in order to only workout 30 minutes a day 3 x  a week, until you spend a fair amount of time learning and doing lots of routines.  It means you’ll try a lot of crap that won’t help in order to find the ones that do help. Unfortunately in order to test a lot of things, it’s going to take some time.  So if you are only exercising the 30 minutes a day, it’s
going to take you a lot of days to get to a working routine.  That’s ok, if you’re aware of that and comfortable with that (most people aren’t).  Or you can try to speed things up a bit by spending more time. Yes you’ll have wasted time, but with good tracking and patience, you’ll get something that works.

It seems that in building a business or getting physically on track, the most important part at the start is showing up.  That sucks because you may waste a lot of time you think you don’t have, but it seems like the only way you can make the mistakes you need to make to learn the lessons you need to learn.

Furthermore people who are successful in either (being very fit or entrepreneurship) tend to do several things:
-enjoy it
-constantly grow, learn, and redevelop themselves / their routines / their business
-spend more and more time doing it, the better they get, despite being more “efficient” (which seems to kind of challenge 4hww a bit)

Maybe if you’re spending a lot of time trying to not spend time on the work / business you are in, you shouldn’t be in it in the first place?

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