Below the Line with James Beshara on Smash Notes

#13 — Matt MacInnis — A Beautiful Mind(set)

Below the Line with James Beshara

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...”

Episode notes last updated on June 20, 2019 14:06


In this episode

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Smash Notes summary for this episode

How can we deal with anxieties that come with the pursuit of entrepreneurial path?

Silicon Valley today is like Florence during the Renaissance, with insane amounts of energy and output. Yet, the battles and crises that humans go through have remained the same.

Matt MacInnis grew up in a small town in Nova Scotia, seeing amazing companies being built in Silicon Valley He wanted to start on. As a result, Matt had spent his 20s agonizing over the pursuit of that outcome, until he had realized that an 18-year-old Matt probably should not set goals for a 35-year-old, and it is okay to change your focus and desires as you gain the wisdom to be rescued from your past.

How should I approach starting a company?

It is perfectly rational to go start a company with insane odds against you if you understand that the outcome is beautiful no matter what. If you can approach it with that mindset, then it will be beautiful.

What lessons did Matt MacInnis learn from his experiences?

Matt had a lot of hard lessons through his career, but he also learned from the book "Zen in the Art of Archery," that everything worth doing is hard, and those hard experiences shape you and make you a better person.

Get the book from Amazon: Zen in the Art of Archery.

What did Matt MacInnis learn from Steve Jobs?

After Steve Jobs effectively stole Matt's designs for a product, Matt realized that your heroes are not who they appear to be. You should never be putting anyone on a piedestal.

What is one secret nobody tells you about?

You might look around and think that everyone else has life figured out, but they don't. Everyone is faking it.

What is Matt MacInnis's head that he does not talk about?

Instead of striving for an achievement, it first helps to figure out whether that is the right achievement for you.

For example, many entrepreneurs want Matt to invest in their company, but instead of answering the question whether Matt should be an investor, they are focused on getting Matt as an investor. Similar, but not the same.

Getting what you want would be a lot easier if you are trying to get the right thing.