Should investors apply pressure and challenge when a company is thriving, or reserve calm support for when it is struggling?

Ed Sim · Jan 10, 2024

Investors should challenge founders when things are going really well and cheer them when things are bad — the opposite of the natural instinct

Venture takes a long time and the companies that look like your best can end up your worst and vice versa, so you have to ride through the cycles

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Kevin Hartz · Jul 22, 2024

When a portfolio company is going really poorly you should be supportive and nurturing rather than hammering the founder; when it is going great you dig in and push hard

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Kevin Hartz · Jul 22, 2024

Tough love should be applied when a company is doing extraordinarily well; when things are going terribly wrong, being a calm, solid, supportive voice is what is extraordinarily helpful

In a crisis the founder is already seized up — teammates quitting, site hacked — so calmness and support are the productive contribution

48:55 20VC: How I Lost Airbnb at Seed Because of an Exploding Term Sheet | Investing Lessons from Roelof Botha & Peter Thiel | Why VC is Less Collaborative Than Ever and Great Companies Are Being Destroyed by Too Much Cash with Kevin Hartz @ A*

Harry Stebbings · Jul 22, 2024

The right support style is individual — some founders need calm nurturing in hard times, others need a kick up the backside

In his own hard times what helped was his mother telling him to stop moaning and get on with it, whereas others resonate with support

49:23 Adapt support style to the individual founder