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The Twenty Year Itch: My Last VC Investment Out of Brooklyn Bridge Ventures

This is going to be BIG.

I understand that now, being an investor in companies that have over 100 employees, closing in on $100mm run rates, where it’s been a long time since I was a Board Observer and most of their interaction is with the bigger, later stage investors that came after me.

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The Stock Dive: How I Learned to Stop Worrying and Love the Market

This is going to be BIG.

5) Is the post-money on your last round north of $30mm and you’ve yet to show meaningful and repeatable revenue traction that comes with positive contribution margins? 3) Do you need to raise a large amount of growth capital in 2022? 4) Are you struggling to get to unit profitability? If so, yeah, then I’d say I’d be concerned.

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When Entry Multiples Don’t Matter

Ben's Blog

OH in South Park, San Francisco (or on Zoom from Big Sky, Montana): “OMG, crazy – that firm just paid 100x revenue to invest in [insert hot startup here] – what could they be thinking?” Multiples are not only used to value companies today but also to value companies several years down the line.

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What Are Pre-Seed Rounds and Why Do They Exist?

View from Seed

These are well known , so I won’t go into much detail but: The combination of the capital efficiency of early stage software companies, the increase in VC fund sizes, and the rise of institutional seed funds created a fairly different early-stage landscape in the following five years. (I

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The Coming Zombie Startup Apocalypse

This is going to be BIG.

Would you be surprised to know that almost half of the dot com companies founded when the boom started in 1996 were still around in 2004--four years after the peak of the NASDAQ? Because companies today have way more revenues than the companies that went public or had huge up rounds back then.

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Playing the Long Game in Venture Capital

Both Sides of the Table

It has historically been the case that VCs would rather fund the promise of 100x in a company with almost no revenue than the reality of a company growing at 50% but doing $20+ million in sales. This “overnight success” was first financed in 2004. It literally drove FOMO. By any external benchmarks this will be a $billion++ company.