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Latest posts

Last updated 1 day ago

Would You Invest All Your Money at This Price?

4 days ago

If I handed you the cash equivalent of your vested equity today...

Why I Haven’t Written Anything This Year

18 days ago

Wait… what?You read that right. I haven't sat down and written a...

The Idiot’s Guide to Raising Venture Capital

19 days ago

“What is all this?”That's what's running through my head at slide seven...

Potentially Pregnant? Try Sheep’s Blood: A Real Future Unicorn Pitch a VC Might Have Gotten in 1976

about 1 month ago

Lately I've been down a rabbit hole on the history of the...

If You Don't Take the Wheel, Your Board Will

about 1 month ago

“I don’t know, Rob. You’re the f*cking CEO. You tell me.”The first...

Revenue and Talent: The Cure for Itchy VC Trigger Fingers

about 2 months ago

Founders aren’t the only ones under funding pressure. I know because it’s...

How to Prompt Engineer A VC

2 months ago

Everybody's figuring out how to prompt an AI right now. Be specific,...

Are you Better at Running the Company Or Running Your Board Meeting?

3 months ago

Some of the best operators I know are terrible in their own...

Climbing the Wrong Mountain: When Founders Build Around Familiar Problems

3 months ago

The first check I ever wrote into Edward Woodford of ZeroHash went...

Should I stay or should I go now? A field guide for discouraged founders

3 months ago

If you’re old enough to know the title reference and the image,...

VCs Don’t Care About Your Product

3 months ago

I can't remember the last time I went through a drive-thru window....

Sourcing Versus Thinking: Should We Put the Deal Flow Sharing Call to Bed?

3 months ago

Everyday, throngs of mostly junior investors join deal flow calls--regularly scheduled check-ins...