Bootstrapper.com - Confessions of Serial Entrepreneurs

So it seems I host the most events out of anyone in NYC tech at the moment. I just wanted to share with everyone why I do it. It’s called being the influencer and connector. People come to me and seek me out because I am the gatekeeper to the network that is NYC tech (one of them). It’s a great place since the host can get away with being aloof and everyone trusts the host naturally so it’s very easy for me to build relationships. When you have a chance to run the show, take it and run it, hosting events and conferences are a very valuable thing for your reputation building - as is having a popular blog.

So I wanted to share with everyone something very exciting - I will be hosting Ibreakfast.com events for the next couple of months. Alan Brody who has been holding the events for over 15 years is going on a book tour and asked me to take them over. It is a complete honor. When I got into the events game a little while back, i thought ibreakfast had the best speakers and brand in NYC. I think it’s going to be a lot of fun to host the events.

We have 2 in planning, Media Buying 2.0 on July 23rd and iEvening, Startup Pitching on July 30th.

Let’s eat!

So I host a lot of events. I’m going to share with everyone a few key tricks to the event game.

1) Always make friends with the host. I host a lot of events, people look to me for information and connections. Every time I make a connection, i put my reputation on the line - do you think I’m going to do it for people I don’t trust?

2) Talk to the person, not the product. Learn about the person, not what they sell.

3) Take a step beyond the event. Don’t leave a relationship at the event. An event is a first touch experience, ask someone out for a drink or lunch or to another event. Don’t assume a first touch experience becomes a sale.

So i went to the gym tonight for the first time in 2 weeks and figured I’d need a rush so I bought an energy drink - one I had never tried before - RedLine - one of the guys warned me it’s like RedBull X5 so i took it anyway… didn’t effect me for about 40 minutes - until I was leaving the gym, then got drymouth and now feel like a rat on speed - super jittery, hyperactive, wide awake and want to run 100 miles. Luckily, I don’t have my shoes on so I don’t think I’ll go running in the dark and trip over my own feet moving too fast. But a warning - watch out for those energy drinks - sheesh. I had trouble sleeping all week and was like a zombie, reminded me of high school all over again. But tonight, wow, I’m going crazy and thus the many blog posts.

While i’m in this hyper attentive state, I figured I’d muse on the NYC tech/finance scene. Lately, I’ve been lucky enough to get in deep in the community, the alley 2.0 so to speak and count among my friends most of the people that throw events in our great city. Interestingly enough, I started throwing events so I ended up friends with the people that do. Probably is subconsciously intentional. What i’ve realized, is that everyone that has started events in the last year or so fits the same profile, overambitious bootstrapper trying to get ahead and not quite sure why they are throwing events yet know people appreciate them and they are doing well. Also, most of the events, don’t make much money. Some do, most don’t, which is something most attendees don’t realize. Small events such as happy hours and the like don’t make bank - big events like conferences bring home the Bacon though.

Along those lines, people are insulted sometimes when they are charged to go to small events - thinking its charity that someone is spending time & money planning events and also putting their reputation on the line. I mean, it’s very risky throwing events for your reputation. If you throw one bad event you can lose your whole audience. It’s much easier just to be in the crowd and attend, then there’s no risk. For example, I cohost a happy hour series, www.startuphappy.com and we charge $10/$20 at the door.

Someone got angry at me for charging and basically attacked me for charging. First off, we have a bar gaurantee and at startup/investor events no one drinks so we lose money at the bar - quite a bit. Our first Happy Hour lost $1500 - out of a $2000 gaurantee, only $500 was spent across 80 people. The cover helps us break even. We don’t profit from the events - it would be nice though to make a few bucks for the time and reputation risk put in but it’s okay, I have a long term view of building my network and helping people. But just something to keep in mind is that most events actually lose money - few make any money next time you bitch about a cover. If you’re unhappy about it - simply don’t attend or throw your own.

Now, I don’t want to sound like I’m ranting which I suppose I am but it can be frustrating sometimes. I love hosting events and helping people so it’s worthwhile and I hope some good comes out of my events. I’ve also noticed that the more you charge for an event, the more people appreciate it. I suspect it is a level of subconscious belief that because it is expensive, it is good and okay to charge.

I have a bunch of cool events in planning and love helping out with other peoples’ events. I feel in the long run being in the center of the network, the crux of the information flow has its merits. It builds a lot of goodwill and goodwill is important for a scrappy up and comer like me that wants to succeed. Sure, i’ve had my successes & failures in the past but I’m up for another go around. Got lots of stuff in the fire and it seems no matter how much I want to focus, I end up involved in more and more projects. Hopefully, I’ll be able to force myself to focus properly in the next few weeks and I give it a go for my next (hopefully) big thing.

Wow, i’m all over the place tonight. Reminder to self - never drink RedLine again - never.

When you start going to events you start seeing a lot of people over and over again. Considering how small our nyc startup community is, you really can’t afford to screw around unless you are a hermit. If you’re social, everyone gets to know you so far. I mean, come on, how many people are really in this community? Not many. My benchmark is the 5000 on the tech meetup list but most people there are enthusiasts not startuppers or investors. Let’s crunch some numbers.

There is maybe 15 vc funds in nyc, average fund has 6 employees = 90 investors, add in ibankers and other related people that focus on seed stage and maybe we’re at 200, now add in professional angels and we’re at maybe 500 investors. Maybe there is 300 tech companies in nyc, each with 2 founders and 300 people that are top execs so we’re up to 1400 people. Let’s add in random other top tier people and we’re up to 2000. now split that in half as half the people on there are anti-social so we’re left with maybe 1000 people. Now divide that by 10 networking groups and the average has an event once a month, the average person goes to one event a month and 50 people show at the average event, we keep running into each other.

I have good feelings for the community here as a number of organizations are sprouting up and being supported. YVCS.org relaunched and is doing very well. The Hatchery launched a few months ago and is doing very well. My little group is taking off. Tri State Ventures just relaunched. All these groups are thriving. for years there was almost nothing going on and a lot of the original groups are gone - the long standing one being ibreakfast but the guard and tides are changing in a very positive way.

Someone needs to build tools for entrepreneurs. At some point I’m starting a non profit with the goal of helping people understand what it means to start a company. Even Cereal Insomniacs like me start somewhere, i made a billion mistakes (i’ll take only 1 penny per mistake). Here are the set of tools I’d like to see.

1) Automated powerpoint creator
2) Automated executive summary creator - not bullshit bplan writing software
3) Event calendar for entrepreneur events
4) Turn BootStrapper.com into a blog site for Cereal Entrepreneurs

Lets get some resources together to actually help people

1) Unless your job is a broker, never straight broker anything unless you actually add value. It’s stressful and leads to strained relationships.

2) When you meet someone you find would be a good person to know, immediately offer advice and introductions without them asking…be nice without asking for anything in return…very few people do it and it builds incredible good will and it doesn’t matter if your introductions end in a deal…it’s one of the few times intent is just as an important as result

3) If you can throw the events, then you control the power of the pulpit.

4) If you can’t/don’t want to throw the event, make yourself invaluable to host, make yourself the kingmaker and be the one to step in when there’s the issue.

5) If someone does you a favor, return it 2X

That’s pretty much it. That’s how I network and anyone that knows me knows I’m a super networker and rarely if ever ask for anything back and usually just like helping people. Helping people is the key= providing value.

Hope I’m helpful

Richie