Matt MacInnis is a founder and investor in Silicon Valley, and he’s widely seen as one of the best personal angel investors out there — combining his experience as a founder (and knowing what made his investors actually helpful and others unhelpful) with the insight into what spaces and products are on the rise.

That’s his day job though. He is a profoundly deep thinker, an articulate leader, but most importantly, he’s honest. He’s seen all the ups and all the downs a founder can see, so you throw experience into that equation, and you’ve got a hell of a conversation.

Some of our favorite quotes from the episode:

"It is perfectly acceptable to go start a company with insane odds against you. If you understand the outcome will be beautiful, no matter what, thats the mindset you need to approach it with and it will be beautiful."

"I could not be where I am today without the hard experiences I had to go through, and it sucked… but they were necessary."
"That was the last time I put another person in the slot of alpha, on a pedestal, someone to emulate…" on his experience with Steve Jobs

"You look around and think that everyone else has it figured it out — and they don't…and I am the first to admit that I’m faking it too."

“I knew where I was strong and I knew where I wasn't, and I was fighting that instead of accepting it.”

“When I sit down across from an entrepreneur…and they really want me to invest, and its not one I can invest in…They’re not answering “should Matt be an investor” while they're trying to answer “can I get Matt to invest in this?” — and these are vastly different questions.”

“Don't win job offers. Go see if you test positive for that particular company or role and let “no” be as beautiful as yes because its the right thing. We are not as interested in truth as we are desire...”