I had lunch with one of my favorite old timer A-lister technology geek dudes today - Dave Winer.  We talk about Ray Ozzie, Salim and all sorts of stuff.

I come home from lunch to find out about Tony Pierce and Marc Brown’s party at SXSW and poor Bill Gross - who went out on a limb, borrowed $50m on cash from BofA in 2000 and now they want to get paid back.

Only problem is - Bill’s $1B incubator fund - IDEAlab - is now worth $300M - and hasn’t had a hit in - well did it ever have a hit?  I think that can be debated.

So this all made me think back to when I had money, lived the lifestyle of the partying boutique incubator applied R&D guy - who didn’t care about making money, sucking up to VCs or liquidity events.

I mean how much does it cost to keep your lifestyle going?  Bill Gross apparently needed $50m.  Me I chewed through about $4M - but I got a lot out of it. 

Scalable Content, rich media interfaces, server-in-the-closet, magicCarpetRide, MyPortals, Meet the MediaBand, The Marc Canter Show, a facewall, adaptive user interfaces, new kinds of tool paradigms, personal identity apps and services, theme restaurant operating system, interactive music videos, interactive TV authoring systems, over 50 interfaces, the world’s first decoupled on-line UI - based upon XML-RPC (Feb. 1999), loads of contacts, relationships, prior art (to bust a TON of patents), good times, some killer parties and of course - knowledge.

I’d say I got a pretty good deal for $4M.  Well invested - and enough fodder to drive about 5 companies.  Its been along run since I left the company I founded in 1992 - and it ain’t over with yet. Some say I went broke. Me - I think of it as investing in my future.

But having lunch with Dave made me look out and try and see a time when I’ll stop - when I’ve done everything wanna do.

Hmmmmm - what a concept.

I also ran in Bob Ellis at lunch, who worked at XOOM when they sold out to NBCi. I reminded Bob that we had signed a deal with them -two days before their announcement and how they made us whole - paying us $25k - “just to be nice”.

What a world we live in.

Dave (Winer) can sit back, change the world from his desktop and still act cool - when he’s ignored and abused.  Ray Ozzie can post a new idea - and have it shoot up Memeorandum and Tailrank, while poor Bill Gross goes broke.  Meanwhile Tony Pierce is getting laid and partying like it used to be 1999.

Me - I’m just working on some killer software with some amazing dudes - and hoping that everyone just spells my name right.

They better at the Buzznet party (I immediately sent away to get onto the list) - or else I want to able to show the homeboys how it was done - back in the 80’s.  We live in amazing time and I’m thankful for people like Dave who can show me how to ’stay mellow’, go with the flow - and yet - still do something that matters.

OPML 2.0 rocks.  Live Clipboard rocks. Putting them all together will rock even harder

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