Coach Software Venture Capital Writing 
Both Sides of the Table
JANUARY 22, 2014
Picking a VC is hard. So I thought I’d write about out with what I would look for in a VC knowing what I know now and why. Most VCs are book smart. VCs should be more of a coach than proscriptively telling you what to do. Traditional software vs. SaaS. Reputation of firm? Of partner?
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. How might our next phase of the journey seem brighter, even with more uncertain days for startups and capital markets? What happened? It was 1991.
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Both Sides of the Table
OCTOBER 25, 2009
Beware of VC Seagulls, who shit on you and then fly away (or worse yet leave you with Red Herrings). I write this post as a warning to pick your VC’s carefully. I like to say to first-time entrepreneurs, picking a VC is more permanent than marriage. I guarantee this is a bad VC. There are many great VCs.
Both Sides of the Table
JUNE 29, 2011
Yesterday I wrote Part 1 of the series on the changes to the software industry over the past decade that has led to changes in the venture capital industry itself. These trends have put pressure on traditional VCs. So VCs spent a couple of years experimenting with earlier-stage investing, which is OK. Funny, that.
Both Sides of the Table
NOVEMBER 18, 2012
I plan to write about it early next year when we’re all through. As I’ve written about before, You’d Have to be a Big Baby to Complain about Being a VC. Think about it – most entrepreneurs who manage to raise seed money or venture capital usually raise enough money for 12-18 months maximum.
Both Sides of the Table
APRIL 10, 2014
One of the interesting things about being a VC is that you often see companies in transition. If you’re an early investor like I am that often means writing the first $2-3 million check into a business that previously had either survived on fumes or on a $500,000 angel round. You’re the coach, mentor, cheerleader.
Both Sides of the Table
NOVEMBER 25, 2010
It is never as rewarding when you’re the coach (but coaching has many other benefits. On Losing in VC. I know I won’t win every deal I want to in VC. Write things down. We helped the write out their requirements for a system. Don’t get me wrong – I’m not a sore loser.
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