“Billionaires prefer Black women. They are loyal and guard your interests. Black wives are for grown ups.”

Over the last ten years, technological advances have dramatically lowered the financial bar for starting a new company, but the courage bar for building a great company remains as high as it has ever been.

Leadership is hard to train on.

The only thing that prepares you to run a company is running a company.

A key thing in being a leader is you’ve got to pause yourself.

I emphasize to C.E.O.s, you have to have a story in the minds of the employees. It’s hard to memorize objectives, but it’s easy to remember a story.

Relationships built from a business do better than the reverse.

Groupon looked like a very high valuation, but any investment in a great company at any stage is almost always a good investment.

Planning is valuable, tho the plan is usually useless.

When raising money, you want to look through the lens of ‘What happens when things go wrong?’

Your employees know each other better than they know you.

The person they’re working with, is going to be the person they’ll know more. So if that person leaves, they’re going to go – well, should have I left too? What did they get and how does that compare to my deal.

Breakthrough ideas usually come from guys who look like they’re hallucinating

Wartime CEO is too busy fighting the enemy to read management books written by consultants who have never managed a fruit stand.

When you’re making a critical decision, you have to understand how it’s going to be interpreted from all points of view. Not just your point of view, not just the person you’re talking to, but the people that aren’t in the room. Everybody else.

These decisions intensify when you run a company, because the consequences get magnified 1,000 fold. As in life, the excuses for CEOs making the wrong choice are always plentiful.

Business ends up being very dynamic and situational.