Bootstrapper.com - Confessions of Serial Entrepreneurs

So over the last few days I have been engaging in Guerilla Warfare. No, I wasn’t in the jungles of Vietnam - I was in the jungles of New York City. Big Bad New York City. Now the Silicon Alley Insider (http://www.AlleyInsider.com) , a great new publication spearheaded by the Scion of Online Advertising, Kevin Ryan and face of the first bubble, Henry Blodget who seems like a really nice guy btw is bringing back the Silicon Alley 100 List - a list of the 100 most influential people in Silicon Alley. Of course, I’m not on the list. I happen to know a lot of people but let’s be honest, I’m not on that level yet. Though I will go toe to toe with anyone in coming up with business idea, marketing strategies or GASP self promotion, I’m not on that level. I’ve never had lunch with Dick Parsons or Barry Diller. For the last few months, I’ve probably been one of the most prolific networkers and for the last month self promoters in our fair tech industry but I’m not on that level (though hopefully one day soon). Do I know people on that level? Yes. Does that mean I’m on that level? No.

So what’s the point of this besides for fawning over Kevin Ryan and his list?

Well, a gentleman and entrepreneur, Nate Westheimer started a peoples choice version of the list. I forgot to mention that AlleyInsider is naming the list internally themselves. So Nate decided he’s going to do the 2.0 version and let anyone nominate people. I marketed myself to top spot on the list - ahead of Barry Diller, Fred Wilson & Kevin Ryan himself. This is the story of how I did it.

For those of you that know me, I’m not one to turn down a perfect opportunity. I decided I wanted to be #1 on the list. What did I do? I asked everyone that I’d done a favor for in the last few weeks to nominate me. I even asked my girlfriend (I love you Bluey). A lot of people nominated me. Did they nominate me because I am the most influential person in New York City? No. They nominated me because I added value to their business for free and they were trying to return me the favor (as a side question: What is more important being the most influential speaker or being liked enough that people will help you out on a whim?)

But I admit I went further. I went further in 2 ways.

The first way was simple. As soon as I saw the list up, I emailed Nate and offered to sponsor the prize. What prize did I offer? A car? No. A Rolex? No. I offered to take the top 3 people in the contest to dinner at Angelos, my favorite restaurant in Little Italy. Why did I offer that prize? I want to go to dinner with Fred Wilson. I think he’s brilliant and is probably the most influential VC in the city (avc.blogs.com is his ever popular blog). I’m being honest.

Now I offered a second prize as well - I offered each of the top 100 people 1 Grey’s Papaya’s hot dog. (cost $1). Why did I do that you ask? Maybe I like Grey’s Papaya? Nope. In fact I won’t even eat the hot dogs myself - I’m kosher. I did it because it was a very New York prize (as Nate said) and because my offering that prize, every single person in the top 100 would find out who I am - and hopefully meet me on a street corner to claim their prize in person. Thus by me offering the prizes, a) I’m giving back b) it’s funny c) the prizes themselves are probably press worth in the marketing industry and d) I would be able to meet all of the top 100 influencers and thereby hopefully build relationships with them and then I would in fact be worthy of one of those spots myself.

So is the prize where I erred? No. Personally, I think offering the prizes is a very intelligent way to be part of something when you yourself may not qualify. (though a warning to marketers: This is only true if you are the only sponsor or the main sponsor otherwise there is too much noise and it only works if your prize itself is unique).

Where did I err? Now, to be fair, when I did this, I didn’t think anything was wrong with it, after all it is a People Choice contest. People Choice implies people choose! To me this means, It is a system meant to be marketed to guerilla style and any technique is fair game. After all we, the average person, like me is the judge. Who cares how I found out about it. There is no written rules for this contest as to who is allowed to vote. Why can’t my girlfriend vote me the most influential person in tech in nyc. Maybe she really does think so? (Or maybe she just doesn’t want to hear me complain that she wouldn’t support for a week) Either way - it’s her choice - People’s Choice.

Now before I tell you the technique I used, I would like to say this - it didn’t even work. So what did I do? I posted a thread on asmallworld.net, the exclusive social network with a link to page and the line “please nominate me for Silicon Alley 100 - help a brother out” (something to that effect). Now, I actually got 2 responses only. After all - who would nominate me for the award (well, i guess i would be trying to hijack my own prize, lol) One response was from a friend in LA who said she would. Now she didn’t say she knew me, she replied on the thread just “sure i’ll do it”. The second post was from another girl, that I really liked and was starting to see as a friend. She did two things. First she replied on my thread accusing me of violating the rules (fist off - there is no rules to violate, second I would be stealing MY OWN PRIZE as I am the sponsor). Second, this person sent me an email saying the following:

�To be completely honest i can’t take you seriously both professionally and personally.

I am sorry to say this, and I don’t want to burn any bridges, but i am just being honest.�

To me this is the greatest insult. I yearn to be taken seriously. I am always the youngest guy in the room. For those of you out there that don�t know my age � I am in my 20�s � I have 8 years of experience running my own companies � I have done very well and I have blown myself up � but one thing that I will always have � or at least I hope to always maintain is my integrity. Why? If you�re the youngest guy in the room there are two paths to take if you want be taken seriously: 1) Be the smartest or b) be the most well liked. Now, I am not the smartest guy so I need to be well liked. I also love people. I really do. I love helping people. For me, there is no greater joy then helping someone else succeed. Getting emails from people saying they are so happy they met me is a real joy in my life. Thankfully I get about 1-2 of these emails per week. Truth me told � I have a LOT of personal references and goodwill. I do not and will not do anything to harm my friends of hurt my good will. I don�t see the point, I�m in it for the long run. There is about 15,000 people in the heart of the New York Tech Community and truthfully there is around 500 people that are the real power players. That�s a small group. We all know each other.

Now, I am very upset about this email I received. Am I upset because she won�t take me seriously personally? No. In fact I don�t take myself seriously personally (boy that would be boring). Am I even upset that she won�t take me seriously professionally? No. I could live with that � though it hurts � I�ll say this a million times, one blip in my reputation can ax me at this critical juncture in my young career. I am upset because I think I lost someone that I thought could be a very good friend. This person seemed like a truly genuine person. In fact, I respect this person more because I can see her true ethics now. This person is a very good person and I would recommend this person 100X over if this person never talked to me again.

But I�ll go a step further and give you a glimpse into my soul. I was at a bar last night with friends and we were chatting, I had a couple Scotch�s (Macallan 12) and I was talking. When I drink I talk trash, I get arrogant, I brag. I woke up this morning hating myself for being arrogant. The people I was with, probably didn�t even realize it (though they might now if they are reading this) but I was arrogant � and I hate it, I really hate it. I hate being arrogant, sometimes I am and I apologize in advance.

I don�t like to give people pause to think bad about me. I don�t want people to think I�m an arrogant young kid and dismiss me. Or worse � not respect me as a businessman. The average person my age has an entry level job. I go to dinner with CEO�s and investors and go toe to toe intellectually with people that run public companies. And you know what, they usually like and sometimes love my ideas. I have friends that are my parents age. Good friends. Confidants. I have lots of friends 10-20 years older then me. Real friends. Personally I don�t believe in age � maturity comes from experience � not age. There are plenty of very old people that immature � let�s be honest here. Most people know my age, the rest of them figure I�m young or can look it up. You can figure out my age on google if you know how to search. I (sadly) usually get 30, once when I was 18, I got 35 (that really sucked). I don�t want to look older � I�m losing my hair � I want to look younger. Honestly, I�d like to go back to college and actually pledge a fraternity. I was running companies in college and didn�t have the time (I actually rarely went to class and graduated on time with a 3.67 GPA from Binghamton University with a Degree in Finance � while running companies). I saw the movie Accepted and I made a few phone calls and seriously looked into starting my own college so I can go back to school � on my terms (seriously, isn�t this everyone dream of college?)

Now, back for a second to this person that inspired this impassioned little diatribe of mine. This person is someone whom, I, without this person asking me, opened up my network to and made introductions for. Now when I make introductions, I don’t introduce any odd person to each other. I make very high level introductions, each one essentially with my reputation on the line. (If i make an introduction and someone gets screwed on this level - you better believe - all of you my tech friends and investors will likely find out - after all, we are all gossip queens in the small water cooler village that is our industry.)

Considering how much stock I put in my reputation and considering that I share all of ideas and strategies on my blog, I’m pretty ripe for the picking if you know what I mean, if I really screw up. One person - any of you - if I screw can ruin me. In fact - I’ll go further, If I have screwed any of you - or if anyone of you - my tech brethren have any reason to believe I’m not genuine, please stand up and post your the New York Tech Meetup & and Old Timers Online Advertising List what I did to you and why no one else in the community should ever work with me again. If I have screwed you, I invite you to come out of the woodwork and ruin my reputation. Sure, not everything I’ve done has gone down well, yes, I’ve had clients that have lost money, lord knows I’ve lost money and made some really dumb decisions, I repeat, really really dumb decisions but if I have harmed anyone here - I hereby submit myself to tarring and feathering by the group. I ask you my tech brethren, if you have ever seen even anyone offer up themselves with earnest like I am doing before you today? You will be hard pressed to find a single person out there that is willing to put himself on the line in such a public forum as this. And yes, I am doing this and putting myself on the line - while I am about to go out and try to raise money. I am not just trying to raise money - I am trying to raise a LOT of money - $10,000,000. Now if I had $10,000,000 and was in the position to say F U to everyone I don’t care what you think - that would be one thing - but I am going to the markets to raise this money. That means my entire blog and this post will be easily found during due diligence. That means that any investor will be able to easily track down the threads from the New York Tech Meetup and anywhere else and see where you my tech friends warned these investors to stay away from me. Would anyone like to stand up and deride me? I am here, Richie Hecker, you’re humble crazy entrepreneurial servant - for the beating - if you so choose. (as an aside: I just had a new idea for a business - i will call it reference networking - what we do is build a social networking site like linkedin but by doing so, you are forced to accept all references - both good and bad so that the world can get a true profile - not just the references of people you could have very well have paid to vouch for you!”)

So then what did I do? I did a post to the Meet Up group apologizing for posting on asmallworld and offering to give back my votes so that I don�t win this contest � and so I will not get the opportunity to take myself to dinner � I offered to forfeit the prize back to the sponsor (myself) and walk away. But guess what? I reached the quota of maximum messages allowed on the listserv for the day (25 � long story involving Bill Gates & India) so did I give up? Nope. I asked a dear friend and kindred soul, Dr. Yao to send out the message on my behalf. Now Dr. Y runs The Hatchery (hatchedby.us) and rightfully deserves one of the top spots. She is super genuine and amazing and incredibly well connected. She sent this on my behalf to apologize to the group. Then the group got confused because she forgot to attach my signature and thought she was the one who gamed the system (but I�d like to take credit for the guerilla warefare) and thus more drama ensues. But hopefully this email will clarify that up as well. (Thanks Doc)

Now, there a few things left to consider. First the reason this contest was started, let�s be honest here, it�s so Nate could promote the new product he was launching. The contest itself is a clever publicity stunt (good job Nate). I will go further � I know I said earlier I apologize for posting on asmallworld and calling out to the public to vote me in � but I leave that question to you? If a People Choice award is for the people to choose and no rules are posted � would it not then be fair game to guerilla market yourself on any venue where you can attract votes? My personal feeling is I didn�t do anything wrong but I actually did a very smart thing � after all I am a guerilla marketer. And if you�ve read this far I must have influenced you in some way � hopefully to buy my book! (just kidding, I don�t have a book coming out � though I would appreciate your vote for most influential person in Silicon Alley as even if I�m no the most influential - I�m pretty sure I�m becoming one of the most controversial. (I apologize again � that�s the publicist in me trying to spin the situation).

So instead I leave the question to you my fair audience � should I be kicked off of the People�s Choice list or left on?

PS. Once again to you I am sorry if I offended you and I just bared my sole so I ask of you if you will give me another chance to earn your friendship?