1999 Entrepreneur Internet Valuation 
Both Sides of the Table
DECEMBER 11, 2022
Something happened in the past 7 years in the startup and venture capital world that I hadn’t experienced since the late 90’s — we all began praying to the God of Valuation. The browser and thus the WWW and the first Internet businesses were born circa 1994–95 and there was a golden period where anything seemed possible. What happened?
Startup Professionals Musings
JANUARY 7, 2023
As an entrepreneur mentor and startup investor, I see with sadness the 50 to 90 percent that fail. Just because you would have loved to have your groceries picked out and delivered, doesn’t mean the mainstream customer was ready for Webvan in 1999. Or ask PlanetRx, an online service for prescriptions, before the Internet was pervasive.
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Both Sides of the Table
SEPTEMBER 28, 2014
it is also the title of a fabulous book from Internet 1.0 by Michael Woolf that is worth any startup founder reading to get a sense of perspective on the reality warp that is startup world during a frothy market such as 1997-1999, 2005-2007 or 2012-2014. Valuation.
Startup Professionals Musings
APRIL 12, 2020
As an entrepreneur mentor and startup investor, I see with sadness the 50 to 90 percent that fail. Just because you would have loved to have your groceries picked out and delivered, doesn’t mean the mainstream customer was ready for Webvan in 1999. Or ask PlanetRx, an online service for prescriptions, before the Internet was pervasive.
Both Sides of the Table
AUGUST 30, 2010
My advice to entrepreneurs was and is “ when the hors d’oeuvres tray is being passed take two ” (e.g. So I agreed to offer my current thinking on the economy and what it portends for the VC industry & fund raising for entrepreneurs. While not 1999 all over again but I am observing first-hand the signs of funding frenzy.
Both Sides of the Table
AUGUST 9, 2011
Valuations were enormous relative to progress in companies. Companies with less than $2 million in revenue were asking for $50-60 million valuations and getting them. I spent my days meeting companies, figuring out what areas of the market interested me and trying to get a sense for how VCs thought about fair valuations.
Both Sides of the Table
MAY 23, 2012
The movie, “The Social Network” might have had more of an impact on creating future entrepreneurs than any other event of the past 5 years. Yes, it’s true that FOMO (fear of missing out) is driving some irrational behavior and valuations amongst uber competitive deals and well-financed VCs. Thank you, Aaron Sorkin!
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