Matt MacInnis: A Beautiful Mind(set) – Below the Line

Key Takeaways

  • Set goals for your future self, but realize that things change – don’t be afraid to change directions given the necessary inputs
    • You DON’T have to achieve every goal you set for yourself, especially if your older (and wiser) self learns of new information that the younger you (who set the goal) didn’t previously have access to
  • More likely than not, most of the problems in your life originate from the fact that you’re continuing to fight what’s true
  • When you start a company, look at it as an experiment
    • “Your ability to control the outcomes in your life are basically 0. There’s a ton of randomness. Certainly you should try hard and engage with your environment and be the best person you can, but at the end of the day luck plays a huge role.”
    • Do everything you can to succeed, but realize – “The odds that your outcome is influenced by your actions is effectively 0. It’s sort of known by the universe when you start what the outcome will be and it’s your job to run the experiment.”
  • NEVER put another human being on a pedestal in any way shape or form – especially in the context of business
  • Be honest about your strengths and avoid being blind to your weaknesses (or covering them up) in the hopes of fulfilling something you’re not truly meant for
  • Let your behavior be driven by a search for what’s true, not by a desire for a particular outcome

Books Mentioned


The Best Radio Voice You Ever Heard

  • Growing up in Northeastern Nova Scotia, Matt became a professional radio DJ at age 15
    • The summer before going off to college, he served as the midday DJ from 10 AM – 2 PM
  • A tip – never drink caffeine or carbonated beverages before going on the air
    • Why? – You already have tons of adrenaline (so you don’t need the caffeine) and carbonated beverages cause you to spontaneously burp while squeezing your diaphragm


  • “We as humans do a relatively poor job, and certainly an infrequent job, of discussing the human condition in an open and vulnerable way”
    • “As you wander through the ocean of humans, once in a blue moon you bump into someone who naturally has a tendency to be open and vulnerable and you detect that very quickly”
      • When you find these people – latch on to them

A Rumi Poem

  • The first page of Matt’s journal contains a poem he hand copied from Rumi:
    • “When I run after what I think I want, my days are a furnace of distress and anxiety”
    • “If I sit in my own place of patience, what I need flows to me and without any pain”
    • “From this, I understand that what I want also wants me, is looking for me, and attracting me”
    • “When it cannot attract me anymore to go to it, it has to go to me”
    • “There is a great secret in this for anyone who can grab it”
  • On the quote:
    • “It’s a reminder for me to stay grounded and it speaks to the demons I struggle with”
    • “This clicks for me at a stomach level so intensely that I never want to let go of that feeling”

Matt’s Personal Evolution

  • In his mid-late teens, Matt (38 now) started to get the sense that he wanted to grow up to be a world-class CEO – this caused him to spend much of his 20s agonizing over the pursuit of that outcome
  • But – “In 2015-2017… I experienced the recognition that my goal was no longer valid. This idea that an 18-year-old can set goals for a 35-year-old is probably not so right.”
    • “The minute you’re able to cast off the notion that once you set a goal for yourself you have to achieve it in order to fulfill some sort of destiny or fill a void in your ego… the minute you’re able to cast that notion aside for even one set of things, you realize that for all sets of things that’s not the right way to do it”
  • Digging deeper:
    • “I would worry so much about the perceptions of others and whether or not I was on the path to becoming this big and successful CEO, but in reality no one was paying attention to me”
  • Matt did end up becoming a CEO around 2000, but – “It wasn’t until later on that I was far closer to being authentic when I showed up to work and presented a more believable and likable version of myself, had better relationships with my colleagues, and did a better job of running the company”
  • Further:
    • Many people set an unreasonable goal for themselves while they’re young and do everything possibly to achieve it, without course-correcting along the way or changing directions (even though it might be necessary)
      • They then judge themselves for not achieving that one particular goal, even if it just wasn’t meant to be

Stop Fighting What’s True (and thoughts on entrepreneurship)

  • “The sum total of problems people fall into in these status races has to do with fighting things they can’t change… fighting what is true… That’s the thing I have tried to rid my life of in the last 4 years – don’t fight what is true.”
  • Eric Ries has said that the psychology to start a company is almost the opposite of the psychology needed in order to run and build a company
    • To start a company – disavow anything that doesn’t agree with your intuition and bust through anything you don’t think is true
    • To build a company – develop the sensitivity and understanding to endure truths all day long
  • The above kind of relates to the serenity prayer:
    • God, grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference

Should you start a company?

  • “It’s irrational to start a company, and nothing will give you a more visceral sense of the horrible odds than being a full-time angel investor.”
    • “There is no lower leverage position than the day 0 entrepreneur, it is just a horrible position to be in”
    • BUT that being said – “It is perfectly rational to go start a company with insane odds against you if you understand the outcome is beautiful… no matter what happens”
      • If you approach it with this mindset, then the journey will serve you well
  • When you start a company, look at it as an experiment
    • “Your ability to control the outcomes in your life are basically 0. There’s a ton of randomness. Certainly you should try hard and engage with your environment and be the best person you can, but at the end of the day luck plays a huge role.”
    • Do everything you can to succeed, but realize – “The odds that your outcome is influenced by your actions is effectively 0. It’s sort of known by the universe when you start what the outcome will be and it’s your job to run the experiment.”

Interact With Systems Not Symptoms

  • “My experience of most people is that they interact with symptoms, not systems”
  • Expanded:
    • “You look at people who seem to be operating at some wavelength you just can’t quite get to, those people aren’t interacting with symptoms. They’re interacting with the system. They’re thinking about the world through a really different lens, and maybe reaching the same conclusions, but by virtue of a vastly different journey.”
      • “People who interact with systems are so much more at peace and ease within themselves, and everyone’s drawn to it. We all want to be around people who are at peace with who they are.”
    • Interacting with symptoms (instead of systems):
      • Is like looking at the leaves instead of the roots
      • Is like chasing the symbol of the thing you want (fame or being on the cover of a magazine) instead of the thing itself (success)

The Story That Changed Matt’s Life #1 – Coming as Gay

  • Matt was in high school at the time, and started coming out to his friends around 9th grade
    • “I cried myself to sleep a lot trying to pray my own gay away… but you just know and you eventually have to come to terms with it”
  • But it took a little longer to come out to his parents…
    • Matt had hidden a gay culture magazine in his father’s filing cabinet
    • One afternoon, after coming home from school, his dad confronted him about it
      • “That moment was pretty tough, but it was the beginning of my life. It was the beginning of me being myself for the first time in front of my parents.”
  • Check out The Velvet Glove to learn more about the experience of coming out as a gay man
  • “I feel bad for people who’ve stayed in the closet and the only true version of themselves is in their head”

The Story That Changed Matt’s Life #2 – The Crimson Newspaper Rape Scandal

  • Matt was president of Harvard’s daily newspaper (The Crimson) when he was 20 (back in 2001)
  • Someone at the school had accused another student of rape and the administrative board was planning to expel the accused student
    • The writers at the newspaper were skeptical of the accuser
      • Here was the dilemma – under Massachusetts state law, you’re allowed to publish the name of the accused, but not the accuser
        • (Matt and his writers didn’t agree with this and being skeptical of the accuser, wanted to get the full story out there)
  • As the person who had to make the decision, all the administrative staff at the university were encouraging Matt to just kill the story
    • “But there was no way I was going to not print it”
      • “Look at where we are today with people trying to skill stories… f*ck that”
  • Matt describes the experience as the first taste he ever had of being a CEO and realizing – “Only the nuclear shit lands in your lap”
    • Complain about CEOs all you want and that they’re overpaid, but they have a job that’s tough as hell
    • Related to this, Sean Parker has famously said – “CEOs get too much credit and they don’t get nearly enough credit”
    • “It was a good taste for me as to how miserable it can be to be at the top”
  • In the end, Matt decided to publish the story with both names 
    • The guy ended up being expelled and the girl’s reputation was ruined
    • There was never any sort of legal fallout

The Story That Changed Matt’s Life #3 – A Meeting With Steve Jobs That Took a Turn for the Worse

  • Matt had worked at Apple from 2002-2009 and had interacted with Steve in passing
    • Then Matt left and started Inkling – they made some killer software/user interface designs for the iPad which Steve soon got wind of
      • Steve then summoned Matt and his head of design for a meeting to check out their work
  • In the meeting:
    • Steve was impressed and immediately knew – “The stuff they were doing at Apple was completely second fiddle”
    • But, after a long moment of silence, in true Steve Jobs fashion, he started tearing Matt and his head of design to shreds – “He kept telling us why we’re f*cked, why our company was going to die…”
    • At the close, Steve asked them if he could keep some of the designs and Matt (regretfully) let him 
      • That move, for the most part, signaled the end of Inkling – all of the design features were included in the next version of iBooks for the iPad
  • Here’s what Matt learned:
    • He had gone into the meeting subconsciously putting Steve in the “alpha male” slot, just from knowing him at a distance
      • “I didn’t know Steve Jobs and there was no reason for me to respect Steve Jobs other than what he had accomplished”
      • “That was the last time I put anybody into the slot of alpha, it was the last time I ever put anybody else on a pedestal in any way”
  • Matt adds:
    • “Steve Jobs was not a nice person and the way he built an empire and became one of the most powerful people in Silicon Valley history is by being ‘not nice,’ and that’s okay. I respect that.”

Everyone’s Faking It

  • “One of the things that really set me free to be myself as a CEO was the recognition that everyone’s just faking it”
    • No one has it figured out
    • “And I’m the first to admit I’m faking it”

The Path of Life (according to Carl Jung)

  • On your route to age 30, you’re trying to prove you belong
  • Once you hit 30, you start trying to prove you’re useful

What’s something Matt thinks a lot about but rarely gets a chance to chat about?

  • “I could spend hours and hours with a like-minded person rejoicing in the miracle of the human mind… it’s such an unlikely thing and so complicated and hard to understand”
  • The logical brain and emotional brain are always competing – the sum total of that combat is this inability for most people to see what’s true and accept it
    • This mostly has to do with the truth fighting that happens inside the minds of people with respect to themselves
      • For example – Someone’s behavior being a function of how badly they wants something (like a job title), not whether or not they’re actually suited for it
      • Be honest about your strengths and avoid being blind to your weaknesses (or covering them up) in the hopes of fulfilling something you’re not truly meant for
        • “Every time you fight your truth… you sub-optimize the outcome and create anxiety, grief, and friction”
      • “This narrative of desire as the driving force for behavior as opposed to acceptance of what is apparent as truth is actually at the core of our species’ inability to self-actualize”
  • How else might this play out in the real world?
    • An entrepreneur pitching as hard as they can to bring on an investor, without realizing that it’s just not meant to be
      • They’re trying to answer the question – “Can I get Matt to invest in my company?”
      • As opposed to – “Should Matt be an investor in my company?”
    • “With job searches, people tend to want to ‘win’ job offers. Don’t win job offers, go see if you test positive for that particular company and that particular role. Let ‘no’ be as beautiful as ‘yes’ because it’s the right thing.”
  • You need to realize:
    • Long term-pain is worth trading for the lesser short-term pain in the pursuit of truth
    • You’ll be okay if things don’t go the way you want them to at this very moment – the universe has a plan
  • In summary:
    • “Be Zen about what’s true and embrace it, and within the constrains of what’s true fight like hell and be competitive. But realize that being competitive and fighting like hell will never change what’s true.”

Additional Notes

  • “My 18-year-old self saw 38 as impossibly old, and now I realize I have so much ahead of me”
  • 50% of all unicorns generated in the last 6-7 years have passed through Y Combinator
  • “We all have to recognize we are swirls in a cup of coffee in the cosmic context”
  • “The human brain has a tendency to draw a straight line from A to B and it is supremely unenlightened. It is not the way great things are built.”
  • Aristotle has said – “The only goal of action is contemplation”
    • It isn’t about what you achieve at all – it’s about the insights you learn about yourself on the other side
  • “If you want me to recommend one book to people, it’s Zen and the Art of Archery
    • “Zen is the artless art, and to get there you have to choose an art”
    • “Entrepreneurship was my archery”
Below the Line : , , , , ,
Notes By MMiller

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