Bootstrapper.com - Confessions of Serial Entrepreneurs

I figured i’d share a list of my projects. Yes, I have ADHD but as an excuse just about every entrepreneur and investor has ADHD to. After all, how can you possibly invest in 23 companies without having some form of ADD or ADHD? In fact i’ve never met an investor that doesn’t have this blessed disease I’m thankful for having it, it allows me to multi-task like crazy and unleash my creativity on the fly.

1) TakesAllTypes.org - my facebook non profit

2) AdSolutia.com - the future of online advertising (about to start raising a big round)

3) Jwed.com/Frumster.com/Shoes! Facebook application. I’m doing some consulting and have an equity stake in Frumster.com, the largest jewish dating site for marriage (i also have the title of Chief Marriage Officer which i just love), Jwed.com - an upstart jdate competitor and Shoes! which is a community of 300,000 rabid female shoe lovers on facebook. (i’m getting to test out a pile of new advertising and monetization techniques and probably and know a crapload about making money on facebook now)

4) GeekPlease.com - the web’s first web2.0 it support community built off of my friends amazing remote access technology. I set the strategy, came up with the name, architected the product and marketing strategy and built the team. I have an equity stake and an advisory role.

5) GeneralATM.com - i’m an advisor to generalatm.com, the fastest growing ATM company in NYC.

6) Facebook app development. I have several investment in various facebook applications. I happen to know how to make money from them so I will be building more and looking to acquire them.

7) BootStrapper.com - relaunching this site as a blog portal and a pile of other related sites for entrepreneurs

SeedingIt.com - my seed capital networking group. We do a monthly brainstorming sessions for entrepreneurs and a monthly happy hour. All invite only.

9) HotUpping.com - stealth startup, investor, cofounder, strategist

10) Adviser to a bunch of other random startups

11) Financiering - currently helping secure funding for several startups and films

12) Substitute Media - helping create a holding company to acquire social media properties, facebook apps and other community websites that are not properly monetized or managed. Also looking at unique alternative advertising opportunities. This will launch in the next 3-4 months. Also will be doing seed investing in social media properties.

13) MediaWhen.cm - stealth startup still in idea incubation phase but with very heavy players, if we do it, has the potential to revolutionize the way people look at media at home.

14) VC Fund - still in stealth, should launch by end of Q1 08. This will be a small unique fund playing upon my network and that of the other founders.

Those of you that know me, know that I don’t pretend to make any sense. I still don’t get myself. The last few months have been surreal, my network keeps growing and i’m fairly well known in the startup community and I really didn’t do so much to get there.

My seed capital group is growing, Sun is sponsoring it and we are launching the Happy Hour Series with The Hatchery & Tri-State Ventures. I’m also looking into throwing a large fancy startup forum sometime in the next few months, exact opposite of my campy informal activities so we’ll see.

I’m working with Frumster & Shoes! Application on facebook to help grow, monetize and finance them.

AdSolutia is generating $2,000 a day in revenue but breaking even and causing stress because leads suck and our technology has issues, one of my clients is screwing me etc…so in general its unpleasant. My demos are almost ready so I can start pitching it around and hopefully can raise money. I think I have a decent shot at it, a lot of people are interested. Our AI is pretty sweet. I also just bought an email marketing company with 400k in revenue and a pile of data. Hopefully we can generate some cash off of it in January. That would be pretty sweet.

I’m informally advising probably a dozen startups in random ways and HotUpping is still in development, we have TakesAllTypes in dev and should launch in January and a few other random things working their way out - Davis’ app may go somewhere if he gets his act together and relaunching bootstrapper and a pile of startup related sites in the next few months that i think could be fun.

I was thinking of working on financing for startups as a business but i just don’t see enough interesting startups that i dont think i can make money from it. Also the whole broker/dealer thing, which i can probably solve. I Still want to get the call center deal done, that would be awesome, been 4-5 months already, that deal would open so many doors if i can take control of a 1500 seat call center company. I can grow the crap out of it.

Due Diligence is a great topic. It sounds scary - it sometimes is. It also is where a lot of deals for apart. Why? Most people aren’t transparent and lie.

News flash: If you’ve gotten to due diligence if you are honest, you will get the deal 90% of the time. The second your lie or screw around, you are out of luck.

What is the big hair beast known as Due Diligence ? Primarily its really just reference checking. Each firm has its own approach and sometimes there is no due diligence or Pretend Diligence but expect the following:

1) Check references, personal and professional. Sharp investors will cold call companies on your resume and ask around your industry as well.

2) Check your resume and make sure you really did work at Goldman Sachs from 86-88

3) Run a background check. So you were arrested for pot possession in 1969? Few people care if you tell them about it but they will run if you try to hide it.

4) Do the same for your management team

5) Check your assumptions and do cursory market research and make sure there is some reasonable chance of maybe hitting 1/3 of your numbers. Also double check that our whizbang technology exists, that it does what you said and that you do have 100,000 users.

This whole process can take 1 day and it can take six months. Its all about transparency.

At the same time, you should ask for references from the investors. Make sure you get references from unsuccessful investments - any investor that will give you a reference to an unsuccessful deal is probably above board if they think their former CEO that they forcibly kicked out won’t bad mouth them to hell and high-water. Any investor that won’t give references is probably a shady dude and stay away.

In the spirit of transparency, I am open myself up to some good old fashioned DD.

I invite anyone who wants to go through my cell phone and crank call my friends and contacts and see what they have to say about me.

I invite anyone to send an email to the NY Tech Meetup list and see if anyone will bad mouth me - or go up on the podium after the meetup and ask “Who has been screwed by Richie Hecker?” (warning: some people will in fact think i’m crazy but i am a self described crazy entrepreneur).

I invite you to come to my seed capital group meetings and see how i manage a group and the quality of my contacts.

I invite you to give me a list of companies or ideas or products and have me give them 10 points of feedback and 5 ideas for each. I will do this for anyone who asks.

I will fwd you 10+ emails from people in the last 3 months alone saying how thankful they are for meeting me and for my advice for their startups.

I will tell you my life story on richhecker.com and all of my philosophies on my blog here.

And I will tell you what happened with my past companies. My first real company ClickZen Worldwide, I founded when I was 15 without so much as a phone line or a dollar and turned into a company worth a couple million bucks that owned a couple million dollars in databases and a small ad network and a nice little office on Broad St. I will tell you that I split a division off of the company because my partner who is a very dear friend was an immature jerk and i couldn’t get along with any longer so i took a very big risk and spun off a division and left ClickZen. (He’s matured now and is a very close friend). ZenFinancial was my call center outsourcing company, we did telemarketing from India, i had an office in New Delhi, India. I brought in something like 200 clients in 3 years primarily myself and had a book of business going forward of $50MM+ for the next year. Fair valuation was $100,000,000. That was a lot of money. It got to be my head. I was a horrible manager and an arrogant naive asshole. I almost opened what would have been the worlds’ largest call center in what was the former Reebok factory (the famous one that got shut down for human rights violations a while back). That would have been dumb. I was called the “Father of Mortgage Lead Telemarketing in India”. I used to be proud of that dubious title. Yes, i’m that asshole

So what happened? I blew it up. I had 2 partners. One is very nice, honest and super successful. The other one I shouldn’t have been working with in the first place (My GF who is always right warned me - actually thats the best way to do some DD on me and my ideas - ask her what she really thinks - she may charge you a Coach bag for it though, I love you Bluey). It turns out he stole a fortune from the company, at least a couple hundred grand, possibly up to a million bucks by selling our leads out the backdoor - to people i introduced him too as clients i brought in originally. Most our clients cancelled, I had a panic attack, i lost my long term contracts and most of my book of business and almost went bankrupt. Scary shit. I borrowed money, threw myself in there, didn’t earn a dime for six months and saved the company. (I didn’t find out why my clients were canceling and about the theft until a year later). I sold my majority stake to my honest partner and left the industry. I took a huge haircut on its value and no I didn’t get a $50MM exit. That would have been nice but i learned from it. Mainly that the most important thing is to relax, move slow and steady and do a boatload of due diligence and active monitoring on any business partners. This is why I believe in serious hardcore break out the big guns due diligence. I didn’t do it myself and it literally cost me a fortune.

After that, I produced a tv pilot (fun but shady experience), did a bunch of consulting, invested in some random startups, completed my degree in Finance (okay, so maybe I do understand a tiny little bit about finance) and tested things out waiting for the next big opportunity.

These days, I run AdSolutia, which is a combination of a few companies, who in total generated about $700k in revenue this year - and i really haven’t tried - it’s a testing bed more than anything else. We have some amazing technology and im bringing on the former CMO of DoubleClick as Chairman.

I consult formally and informally for a dozen startups. I develop marketing strategies for fun and am a professional networker. I’m a connector. I like putting people together, any of the dozens of people who has gotten my introductions will vouch for the quality of my seal of introduction. I also run a seed capital group. I’m a startup junkie.

And that’s where I am today

I have no regrets.

This will show you a) my intelligence b) i used to be an asshole c) i used to want to be a trial lawyer

I did mock trial in high school. I was a lawyer. There was a witness on the stand, i caught her in a technicality lie but i pressed it and i got her so confused she had no idea what was going on. I got her to admit she had just lied on the stand, that she was under oath, that she knew what perjury was, that she just perjured herself and that she knew she was going to jail. I went too far - way beyond discrediting her - just to make sure she was fully discredited. I wanted to take no chances and I always relished the oportunity to show off my intelligence. We won the case but i got a low score. My coach and team forced me to apologize - i didnt want to - “if you’re going to swim with the sharks, you may get bitten” was my attitude - yea i know it was like running up the score but in reality there is no decorum in the court room (a lesson i learned a few years later by being screwed because of the courts)

After i asked the judge why i got a low score and that i thought it was unfair because i ripped her to shreds and clearly deserved a top score. He said because a jury would hold it against me and that you need to show emotion in front of a jury. I replied “but this was a bench trial - it’s your job to be impartial in the eyes of the law and i wanted to make sure you knew she was lying” He replied “you’ll make a great lawyer someday”

So people ask me all the time who i am and what i’m about…so here’s the rundown for my readers:

First let get the generic stuff out of the way. I’m young, I’ve been working since I was like 13 and running my own companies since I was 15. I Started a company out of an AOL account and no phone and a year later had an office and employees, I thought I was the man. I was reality just an arrogant 16 year old. What can you do? Thus is life. I’ve made some huge mistakes, I’ve built 2 nice sized multi-million dollar companies, one of them was probably worth at its height $100,000,000 - and that’s based on actual sales contracts that i brought in myself - not eyeball mumbo jumbo - and then i blew it up - what actually happened you can find my old posts but suffice it to say, I fixed the problems, sold and got out - though I lost some hair. No I didn’t get the huge exit everyone assumes I did. I could have though I had offers to sell the company for more - but i was honest. It’s alright, I did fine and I’d still be an arrogant prick if i did - instead of humble and down to earth. In the grand scheme of things I’m happier now as a normal guy that i would have been as a crazy rich arrogant prick of a kid. What do you think?

Since then, i’ve done a bunch of stuff, consulted for a lot of people, helped lots of people start companies, produced a tv pilot and made some dumb investments. I also started a company out of revenge - the worst reason to do it - and of course it failed.

Where am I now? I run an online ad company that i’m about to embark on the process of raising a huge round of capital. And you know what - I think i can. And no i’ve never had a public exit or even taking on a dime of outside capital. We’ll that’s not true - I took on partners on a few ventures all at once and my developers didn’t come through and the projects went up in smoke - so i took the losses myself and paid my partners back out of my pocket.

I just think i can because i have a great fucking idea, great team, tech and i know how to sell myself. I can market the crap out of myself and can network like a frog can jump on lilly pads.

My life story can be seen online at www.richhecker.com. It is the worlds’ only animated life story and resume. I have my own cartoon - who else can say that? Not trying to be arrogant - it’s just how i market myself.

Whenever i get into a new situation, I either stand out or never come back. I have no middle. I either take on responsibility or leave - i don’t just go to events, I host them.

I love building things, I love playing sports and martial arts and i have a tick because i have a pinched nerve in my neck from not stretching properly - stretch or pay the price.

My body feels like its 40 but i have the happy go lucky attitude of a 12 year old - and the experience of a director of a fortune 500 company. I know my shit. I can position things very well and i can come up with ideas on the spot. GIve me a problem and a day and i’ll give you a solution. It comes natural to me but i suck at math - go figure.

My memory sucks - it used to be great, i used to be able to memorize entire pages, now you’re lucky if i know your name. I say its from growing wiser. if you are wise, you dont have to be smart. i’ve blogged on this too. just know how to apply other peoples smarts. The truth is its probably from a mixture of over memorizing shit in school, too much alcohol in college and getting hit in the head too many times in martial arts training. Full contact martial arts can do that to you. WHat can i say? I’m happy.

I believe in karma. Good karma. lots of good karma. I love helping people. Yes i dont mind helping people without getting anything in return. If you ask me to help i will try to help you. In fact I’m flattered you thought to ask me. I will not turn you down if its reasonable and your a good person. If your not a good person - get lost.

I will give free advice to any entrepreneur that asks. That’s right - just ask. If you are funded though id like something for it - because you can afford it but if you cant afford me - i dont cost anything - i’m like the blue chip $5000 hooker that works free for homeless people - shes just a nice person at heart.

I love connected people and creating relationships. If i can create a friendship i am happy. It means i added value to peoples lives. I like adding value. It gives me a sense of self -worth. Making a lot of money is nice but adding value to people is better. It makes you feel secure. I don’t need to be worth $10BN and a meglomaniac to be content - as long as i add value of course id love $10BN. I’d take half of it and solve a world problem and live like a king with other half.

I’d rather help people than profit at their demise - though occassionally even i admit its necessary. Some companies are meant to go bankrupt - bad management is bad management.

I don’t believe in subsidies, please eat what they kill. Add value or get lost. Leech and leave me alone.

Since I was little people have told me i’m special, some in nice ways, others not. you see i have no middle i was a space cadet in school and socially awkward. now i’m a social butterfly. i love being social because i was a geek when i was little. yes i admit it. Revenge of the nerds eh?

i am blunt - i say things people disagree with and dont like - ocassionally i brag - im sorry when i do, im working on it. I also get excited too fast. It’s a habit, i’m sorry.

So what else do you want to know?