Tim Ferriss, The Random Show, Fall Edition (#31)

0:00:01 – What was that aha moment for you?
0:00:05 I see something the rest of the world doesn’t see yet.
0:00:05 – Yeah.
0:00:06 – Well, I mean–
0:00:08 – Simon Sinek, popular at 50 million views.
0:00:10 – I mean, my initial conclusion was,
0:00:12 the good partnerships, you love the partner,
0:00:13 and they’re offering you the ability
0:00:15 to expand your vision.
0:00:17 Though it won’t be perfect, no relationship is,
0:00:18 you still love coming to work
0:00:20 because you feel like you’re still advancing
0:00:21 the greater good in building this business.
0:00:23 Those are the partnerships we should be pursuing.
0:00:24 – Discomfort is one of those things
0:00:26 that to learn to be uncomfortable
0:00:28 is nobody who’s ever achieved anything in the world
0:00:29 did it smoothly.
0:00:32 We all came close to zero if not hitting zero first.
0:00:35 And when you’re coming up to a stranger,
0:00:37 can you help me get out of this?
0:00:38 My answer is always the same as,
0:00:40 why would I get into mud with a stranger?
0:00:41 – Right. – I don’t know you.
0:00:43 Go ask somebody who loves you.
0:00:44 It’s safer to be vulnerable with me
0:00:45 because I’m a stranger.
0:00:46 It’s hard to be vulnerable
0:00:48 with somebody who actually knows me.
0:00:50 I don’t know the three most important words
0:00:52 that a young entrepreneur can ever learn.
0:00:53 It’s your story, it’s also my story.
0:00:55 I thought I had to have every answer
0:00:56 and if I didn’t, I thought I had to pretend that I did.
0:00:58 Let me tell you, you are who you are
0:00:59 and the rest of your life is simply an opportunity
0:01:01 to live in balance with that wire.
0:01:03 I’ll show you another way to find your wire.
0:01:04 Which is, and this is.
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0:02:06 Happy Father’s Day.
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0:03:34 – Simon, thank you for joining me.
0:03:35 – Thanks for having me.
0:03:36 – So great to have you on.
0:03:39 I’ve been a fan from afar watching what you’ve done
0:03:41 over the years and your content.
0:03:42 In preparation for this interview,
0:03:44 I had to go and just check the numbers
0:03:47 of how you’ve blown up over the years.
0:03:51 I mean, it’s insane, so 56 million views or so
0:03:53 on Start With Why.
0:03:56 Did you have any idea it was gonna be that big?
0:03:57 – I mean, of course not.
0:03:59 It’s winning the internet lottery.
0:04:00 I knew that the talk resonated
0:04:02 because it wasn’t the first time I gave it.
0:04:04 I’d been giving the long version of that talk
0:04:05 for a few years.
0:04:09 I knew the content was resonant with people.
0:04:12 I knew it was a different way of seeing the world.
0:04:13 But of course, I could never have known
0:04:15 that it would do what it did.
0:04:17 Combined with the fact that the audio quality
0:04:19 is terrible and the video quality is terrible.
0:04:23 And it’s living proof that it slick comes second.
0:04:24 – Yeah, I look back on that.
0:04:25 It’s not even HD.
0:04:26 – That’s terrible.
0:04:29 – My microphone breaks in the middle of my talk.
0:04:30 – Yeah.
0:04:32 There’s a handful of books that have really changed
0:04:34 my thinking, especially around entrepreneurship
0:04:36 and leadership, zero to one.
0:04:38 There’s a handful of ones where I’m just like,
0:04:41 oh wow, there was some great insight there that happened.
0:04:43 Where did this come from?
0:04:45 Where was that aha moment for you where you’re like,
0:04:49 I see something the rest of the world doesn’t see yet.
0:04:54 – Like most of these ideas, they’re rarely an aha moment.
0:04:56 It’s more like evolutionary steps.
0:04:59 The realization after many steps, and this was no different.
0:05:01 I came from an advertising and marketing background.
0:05:03 And I was always curious why some marketing worked
0:05:04 and some marketing didn’t.
0:05:07 I wasn’t the creative teams ’cause I could have
0:05:10 the same creative team make good stuff and bad stuff.
0:05:11 And it wasn’t just the clients.
0:05:13 I had clients that made good stuff and bad stuff.
0:05:14 And so I looked at sort of the great marketing
0:05:18 that I admired and I recognized that there was a pattern
0:05:21 that it all started with why they did what they did.
0:05:24 And I articulated the concept way back then
0:05:25 just to explain why some marketing worked
0:05:26 and some marketing didn’t.
0:05:28 That’s all it was.
0:05:29 And the original model was why, what, how.
0:05:31 The definitions were the same as they are now,
0:05:32 but it was why, what, how.
0:05:33 And I used to use that.
0:05:34 I started my own business and I used to use that
0:05:36 as my sort of pitch, you know.
0:05:38 And it wasn’t until much later I went to an event
0:05:40 at this black tie affair and I was just sort of
0:05:42 coincidentally seated next to somebody
0:05:43 whose dad was a neuroscientist
0:05:46 and we just started talking, making small talk.
0:05:49 Yeah, and she was telling me about neuroscience 101.
0:05:50 And I was curious about it.
0:05:52 And I came back and started like Googling like crazy.
0:05:54 And I realized this little model that I had discovered
0:05:56 and the neuroscience perfectly overlapped.
0:05:58 I hadn’t discovered why marketing worked.
0:06:00 I discovered why people do what they do.
0:06:02 So I reached out to a famous neuroscientist named Peter Wiebrough
0:06:05 who was the head of the Semmel Institute at UCLA,
0:06:07 which is the largest neuroscience institute in the world.
0:06:10 I don’t know how I got hold of him, but I did.
0:06:12 And I basically said, I need you to look at this stuff.
0:06:13 If I’m gonna say this is related to neuroscience,
0:06:15 I need this blessed.
0:06:15 Yes.
0:06:18 So I like went to his house for a weekend,
0:06:20 just basically talk nonstop.
0:06:24 And I came in on Sunday morning and he was like fidgety.
0:06:25 And I’m like, what’s the matter?
0:06:27 He goes, it doesn’t match the neuroscience.
0:06:28 I’m like, well, what do you mean?
0:06:31 He goes, you need to switch what and how.
0:06:32 I’m like, done.
0:06:33 Yeah.
0:06:34 Maybe came why, how, what?
0:06:35 Yeah.
0:06:36 The definitions are always the same,
0:06:38 but to match the neuroscience of how brainwork,
0:06:39 that’s what it was.
0:06:41 I started to realize that this thing had power.
0:06:44 At a later point, it saved me
0:06:46 ’cause I’d lost my passion for my own work
0:06:48 and hit sort of a really dark period.
0:06:50 And I realized that I knew what I did.
0:06:52 I knew how I did it, but I didn’t know why.
0:06:54 So these things all sort of collided,
0:06:57 personal depression, plus my exploration here.
0:06:58 And it all sort of came together.
0:07:00 I have at least a half dozen friends right now
0:07:03 that have landed in what they thought
0:07:05 was gonna be their dream job.
0:07:07 It typically happens via an acquisition.
0:07:08 It’s a tech entrepreneur.
0:07:10 They get acquired by a big company.
0:07:11 They’re now inside the belly of the beast
0:07:12 of something large.
0:07:14 And they have a couple of sayings.
0:07:15 It’s like, vest in peace.
0:07:17 Or it’s just like, you’re just vesting
0:07:19 and kind of showing up and quiet quitting, right?
0:07:20 Which I’m sure you’ve heard about.
0:07:22 What’s going wrong there?
0:07:23 What’s happening?
0:07:25 Why are they feeling this way?
0:07:28 You’re asking something that’s,
0:07:30 something that happens two or three steps prior.
0:07:31 Okay.
0:07:36 The number of young idealistic entrepreneurs
0:07:40 who start businesses and ethics matter to them
0:07:42 and treating their people right matters to them
0:07:43 and culture matters and all the things
0:07:45 that I write and talk about matters to them.
0:07:49 And they build these beautiful businesses
0:07:52 and then they sell them to the highest bidder.
0:07:54 Not to the company that believes in their values
0:07:56 and has to maintain the culture.
0:07:58 The highest bidder, right?
0:08:01 And the company goes to shit.
0:08:04 They change the ingredients of the product
0:08:06 because they go for something cheaper,
0:08:07 et cetera, et cetera, et cetera.
0:08:08 You go down the line.
0:08:10 And these, they can rationalize it
0:08:11 because they cashed out big.
0:08:13 They can rationalize that, no, we did it right.
0:08:14 And they didn’t.
0:08:16 That’s, be honest, they didn’t.
0:08:17 Why not take a little less money
0:08:19 and sell it to the right company who believes in the values
0:08:21 rather than just sell it to the highest bidder?
0:08:23 And so, if they’re stuck in a place
0:08:25 where they don’t wanna be there,
0:08:28 well, that was their choice.
0:08:29 They chose that partnership.
0:08:32 That’s like marrying somebody just ’cause they’re pretty.
0:08:34 And then complaining that my marriage isn’t working
0:08:35 and we don’t get along.
0:08:40 And I’m like, I don’t know how many marriage advice for you.
0:08:43 – It’s hard though too ’cause you have stakeholders, right?
0:08:44 – Well, that is another thing.
0:08:46 It’s the same trauma, which is,
0:08:49 so many entrepreneurs who are looking for capital,
0:08:51 they take the biggest capital
0:08:54 from the most famous venture capitalist,
0:08:56 not less capital from the right venture capitalist.
0:08:57 – That’s right.
0:08:59 – So, they chose their own partners
0:09:00 and then they’re surprised
0:09:02 whether partners are applying massive amounts of pressure
0:09:04 on them to make decisions that they don’t wanna make.
0:09:05 – Yeah.
0:09:07 – I don’t have a lot of sympathy, you know?
0:09:09 And we have reached the point now where,
0:09:10 and I can’t remember the statistic, it’s overwhelming.
0:09:12 It’s something like 80% of companies
0:09:15 are venture capital or private equity backed.
0:09:18 And so, we used to mock the public markets
0:09:20 that the pressure exerted by Wall Street
0:09:22 would force CEOs to make decisions
0:09:24 they knew were bad for their companies.
0:09:26 And we’re now at a point where private companies
0:09:27 are basically functioning like public companies
0:09:30 where the external pressures are so great
0:09:32 that the number of young, brilliant,
0:09:35 fantastic, talented CEOs getting fired from their own companies.
0:09:37 I have a friend who just got fired from her own company
0:09:39 because she didn’t have control of it.
0:09:40 – Yeah.
0:09:41 – And she couldn’t make decisions.
0:09:43 They fired her because she was trying to do
0:09:45 the quote unquote right thing and follow the vision.
0:09:47 And they wanted to do the thing that made it prettier
0:09:49 to sell in a short period.
0:09:51 There’s an element of like, you made your bed.
0:09:55 And so, there’s even a degree of,
0:09:57 look, I’m not in their position,
0:09:59 but there’s even a degree of irresponsibility.
0:10:02 You made the choice to take the deal
0:10:04 and now you’re dissatisfied with the deal.
0:10:06 You have sort of sellers remorse.
0:10:09 And so, you’re gonna quiet quit because you’re pissed off.
0:10:11 I’m like, they didn’t do anything wrong.
0:10:12 – Right.
0:10:13 – You took the deal.
0:10:15 I think there’s some soul searching to be done
0:10:17 in business writ large,
0:10:19 which is who we take money from and who we sell to.
0:10:20 Because I think a lot of good companies
0:10:23 actually don’t survive the founders
0:10:24 because of who we sell them to.
0:10:26 – I can almost count it like clockwork
0:10:28 because I’ve seen so many of these deals
0:10:29 and I know what it is.
0:10:30 It’s a three-year vest.
0:10:31 When you sell the company,
0:10:34 they put golden handcuffs on you for three years
0:10:36 and you can almost just mark the date.
0:10:37 And then you see a founder being like,
0:10:39 I’m leaving and it’s of course
0:10:41 right at the three-year anniversary, right?
0:10:42 And they’re out.
0:10:43 And then if they were holding it together
0:10:45 with any duct tape or whatever else,
0:10:48 like everything seems to fall apart from there, unfortunately.
0:10:49 – Good partnerships.
0:10:50 You love the partner.
0:10:52 You love the buyer.
0:10:54 And they’re offering you some sort of ability
0:10:57 to expand your vision that you couldn’t do yourself,
0:10:58 which is why you took the deal.
0:10:59 – That’s right.
0:11:01 – Fundamentally, you come to an arrangement
0:11:02 where even though you have a boss now
0:11:04 and you didn’t have one before,
0:11:05 that there’s a degree of independence you have
0:11:08 to build this brand, which is what they want as well.
0:11:12 And though it won’t be perfect, no relationship is,
0:11:15 you fundamentally still love coming to work
0:11:16 because you feel like you’re still advancing
0:11:18 the greater good in building this business.
0:11:19 – Right.
0:11:21 – So those are the partnerships we should be pursuing.
0:11:22 – Yes.
0:11:23 Yeah, that makes a ton of sense.
0:11:25 It’s almost like feel for the fire at that point.
0:11:26 Like you’re joining forces with someone
0:11:29 to help you expand and grow a lot faster.
0:11:31 – What about individuals that are,
0:11:34 I see as individual contributors to an organization
0:11:36 and I see some of these resumes
0:11:38 when I’m looking to hire, say an engineer,
0:11:39 and you see bouncing around.
0:11:40 You see bouncing around
0:11:43 between different employment opportunities.
0:11:45 What advice do you give them
0:11:46 and how do you help coach someone
0:11:49 through finding their why?
0:11:51 – Well, there’s a couple of different questions there.
0:11:53 You and I, when we were younger,
0:11:55 even if we hated our job,
0:11:58 we would never dream of quitting in less than one year.
0:11:58 – 100%.
0:11:59 – We couldn’t.
0:12:00 – It would look so bad.
0:12:01 – And we all knew that if you did that,
0:12:03 it would destroy your resume.
0:12:03 – Yes.
0:12:05 – It would create a bad narrative
0:12:07 about what kind of employee you were.
0:12:09 And I mean, it would have to be pretty toxic
0:12:11 for you to leave it under a year, right?
0:12:14 And so we held our nose and we made it to a year.
0:12:16 And this predominantly younger generation,
0:12:17 no, it’s not exclusive,
0:12:19 but predominantly younger generation
0:12:21 is very comfortable quitting quickly
0:12:24 and sometimes for not good reasons.
0:12:25 And I’ve seen it happen,
0:12:27 which is the young people who are so confrontation avoidant,
0:12:29 they’d rather quit than go through the discomfort
0:12:31 of asking for a raise, for example.
0:12:33 For every action, there’s an equal opposite reaction.
0:12:34 There’s a finite mindedness to it,
0:12:37 which is how do I solve the immediate problem in front of me
0:12:40 without considering the long-term impact of that decision?
0:12:42 I’m not for or against the decisions.
0:12:44 I’m saying consider the long-term impacts.
0:12:45 And I’ve been public about this
0:12:47 and I’ve been criticized for it by young people,
0:12:51 which is flash forward five or six years
0:12:54 and you’ve had seven jobs, right?
0:12:55 And whether you’re bouncing
0:12:57 because you think they’re all toxic
0:12:58 or whether you’re bouncing
0:13:00 because you’re just dialing for dollars, whatever it is,
0:13:02 in five or six years,
0:13:03 the new employer is looking at you
0:13:04 and you’re a certain age now,
0:13:07 which means I expect a certain level of maturity
0:13:08 and accomplishment.
0:13:09 – Yes.
0:13:11 – You haven’t had it
0:13:12 because you haven’t gone through the shit.
0:13:13 – Right.
0:13:14 – You keep jumping shit.
0:13:16 So I don’t even know that you’re qualified
0:13:18 for the senior position you’re applying for
0:13:19 that somebody else with seven years experience
0:13:21 could apply for, number one.
0:13:24 And number two, if I’m given two resumes,
0:13:27 one with somebody who’s bouncing around
0:13:30 and one who’s like had two jobs over seven years,
0:13:31 I’ll take the one with two
0:13:33 because I’m not gonna trust
0:13:35 that this person’s gonna stick around
0:13:37 after I’ve trained them up and got them all in.
0:13:38 We have a few years
0:13:39 before we start seeing the repercussions,
0:13:41 but the repercussions are coming.
0:13:42 – Yeah.
0:13:43 – And again, I’m not saying don’t quit.
0:13:47 I’m saying just be cognizant
0:13:49 that there are implications
0:13:52 and maybe be a little slower.
0:13:53 – Do you think the problem there
0:13:55 is that they’re picking the wrong profession
0:13:58 and wrong job from the get-go
0:14:00 or they don’t have the grit to stick it out
0:14:02 during the hard times?
0:14:04 You mentioned this confrontation avoidant.
0:14:05 Is it because they are like,
0:14:07 this makes me uncomfortable.
0:14:08 I can’t handle it.
0:14:09 I’m out.
0:14:11 Or did I just pick wrong right away?
0:14:12 I know we’re generalizing, but–
0:14:13 – I mean, who knows?
0:14:16 But this idea of dream jobs is a funny thing, right?
0:14:17 – Yeah.
0:14:19 – Ain’t no such thing, number one.
0:14:20 Every job is imperfect,
0:14:22 like every relationship is imperfect.
0:14:24 And we live in a world that idealizes
0:14:26 both relationships and jobs.
0:14:29 And so when my relationship isn’t perfect
0:14:31 and my partner doesn’t do all the perfect things
0:14:33 and then I ban in that relationship,
0:14:34 and I’m doing the same thing,
0:14:36 this job isn’t perfect and I have stress
0:14:38 and they want me to work late on a Thursday,
0:14:40 there’s a problem with pursuing the dream job
0:14:43 because it doesn’t exist.
0:14:45 Now, that’s not to say we should suffer either.
0:14:47 I believe you should have joy at work.
0:14:49 I believe you should be fulfilled by work.
0:14:50 I believe that you should be inspired
0:14:51 by the company you work for,
0:14:53 but you don’t have to like every day.
0:14:54 You can love your children,
0:14:56 you don’t have to like them every day.
0:14:56 You can love your job,
0:14:58 you don’t have to like it every day.
0:14:59 I think we confuse the two,
0:15:01 that there are days that I don’t like my job
0:15:02 and that’s the reason to quit.
0:15:04 But the fundamentally,
0:15:05 are you working in a place
0:15:06 where you feel seen, heard and understood?
0:15:07 Are you working in a place
0:15:09 that you feel like you’re growing as a human being,
0:15:11 that you actually are a better version of yourself
0:15:13 because you work here?
0:15:15 Are they pushing you and challenging you
0:15:17 to take on more responsibility
0:15:19 than maybe you even think you’re capable of?
0:15:21 And that’s uncomfortable.
0:15:24 And if you go back to Steve Jobs, for example,
0:15:25 and I know we herald him,
0:15:27 but he was pretty remarkable, right?
0:15:29 One of the things that Jobs did
0:15:31 is it was uncomfortable working at Apple.
0:15:35 And it wasn’t uncomfortable because he was mean,
0:15:38 although he wasn’t the nicest person in the world,
0:15:40 it’s because he saw potential in people
0:15:42 that they didn’t necessarily see in themselves.
0:15:44 And he pushed and pushed and pushed people.
0:15:47 And people who didn’t like being pushed, they quit.
0:15:49 But the people who were okay being pushed,
0:15:53 they all said, I achieved more at this company
0:15:56 than I ever would have imagined.
0:15:59 Johnny Ive, this sort of middling designer,
0:16:00 Jobs sees something in him
0:16:03 that maybe he does or doesn’t even see in himself.
0:16:05 And he gets pushed and pushed and pushed and pushed.
0:16:07 He becomes one of the greatest designers
0:16:08 in modern history.
0:16:10 – I had a really long conversation with Tony Fidel
0:16:12 about this, working with Jobs,
0:16:15 and the growth comes from the discomfort.
0:16:17 – The growth comes from the discomfort.
0:16:19 I mean, look, there’s so many metaphors and analogies,
0:16:21 I love the one about the lobster.
0:16:22 – I haven’t heard the lobster one.
0:16:26 – So, lobsters, the soft mass inside the shell
0:16:28 is what grows, that’s the audience.
0:16:30 The shell itself doesn’t grow.
0:16:35 It’s this hard thing that excretes out and hardens.
0:16:37 And as the lobster grows,
0:16:40 it starts to get very uncomfortable in its own shell
0:16:41 ’cause it’s now bigger.
0:16:43 It’s like wearing clothes that are too small.
0:16:45 And only when it gets to that point,
0:16:48 does it then shed the shell and build a new one.
0:16:51 In other words, you can’t grow without being uncomfortable.
0:16:52 – Right, right.
0:16:52 Yeah, that’s so good.
0:16:53 – And that’s true.
0:16:55 I like to equate everything to personal relationships
0:16:59 because corporate relationships are relationships, right?
0:17:03 Which is every fight or uncomfortable situation
0:17:04 I ever had with my girlfriend.
0:17:06 Though I did not enjoy it,
0:17:08 though I wish we’d never had it.
0:17:09 Though sometimes I was to blame,
0:17:10 sometimes she was to blame.
0:17:13 More often than not, we were both to blame.
0:17:14 And when I say that just a quick aside,
0:17:16 usually in an argument,
0:17:18 we start accusing each other of who started it.
0:17:19 The reality is, yes,
0:17:20 absolutely somebody always started it.
0:17:22 And the other person almost always poured gasoline.
0:17:23 – Yes.
0:17:25 – So you both have a culpability.
0:17:27 It doesn’t matter what started it.
0:17:28 You both made it worse, right?
0:17:31 Invariably, every uncomfortable conversation
0:17:33 or fight that we ever had,
0:17:36 though I hated every moment of it and so did she.
0:17:38 We ended up stronger and closer because of it.
0:17:40 Because there were lessons that were learned.
0:17:44 There were triggers that were realized.
0:17:47 There was language that was dissected.
0:17:50 And what we did was learn to fight,
0:17:53 not against each other, but against the problem.
0:17:57 And I think it’s the same at work, right?
0:18:00 Which is when there’s pressure exerted,
0:18:02 is it me versus management?
0:18:04 Or is it management and me
0:18:06 versus whatever we’re trying to accomplish.
0:18:08 And good leaders know that.
0:18:10 And good team members know that.
0:18:13 It’s when it becomes adversarial.
0:18:14 Us versus them.
0:18:15 – Yeah.
0:18:16 – And by the way, I blame leadership
0:18:18 as much as I blame employees.
0:18:21 Team members will go out for drinks and vent about work,
0:18:23 which I’m, by the way, totally healthy.
0:18:24 – Yeah. – I’m in problem with that.
0:18:25 But sometimes narratives,
0:18:28 and especially in virtual and distributed workforces
0:18:30 where everybody’s wherever they are,
0:18:32 the rumor mills can spin out of control a lot quicker.
0:18:33 – Yes.
0:18:36 – And we blame management for what they did to us
0:18:37 or whatever.
0:18:39 But it happens at leadership as well.
0:18:41 The number of times I’ve sat in leadership groups,
0:18:45 including my own, where we label someone dumb,
0:18:50 or lazy, or inconsiderate, or one foot out the door.
0:18:52 And we make jokes about,
0:18:55 ugh, here we go again, we’re entitled,
0:18:57 or just go down the list.
0:18:59 And we label them, we create a narrative about them,
0:19:01 and now we treat them that way.
0:19:03 And though they may not know our narrative,
0:19:06 they know that they’re being treated a certain way.
0:19:09 And so one of the things that is imperative
0:19:10 in any leadership team,
0:19:13 which is when one person finds themselves venting
0:19:15 about somebody where it’s creating a narrative
0:19:16 about another human being,
0:19:18 it’s imperative that somebody else in the leadership team
0:19:20 interrupt that narrative.
0:19:22 And say, they could be lazy.
0:19:25 True, that’s definitely a possibility.
0:19:26 Or they’re overwhelmed,
0:19:28 or we haven’t given them good instruction,
0:19:29 or they’re struggling at home.
0:19:30 – Yeah, I was gonna say,
0:19:32 are they going through a divorce or something?
0:19:33 We don’t know about.
0:19:34 There’s a list of things.
0:19:36 And so we treat them with empathy
0:19:37 and maybe check in on them.
0:19:38 I expect leadership to go first
0:19:40 ’cause they should know better.
0:19:41 But whether it’s in a group of team members
0:19:43 about each other,
0:19:45 more about management,
0:19:46 management about team members.
0:19:48 And again, I hold the leaders to a higher level
0:19:49 of accountability.
0:19:50 And if they act appropriately,
0:19:51 the team will act appropriately.
0:19:53 But we have to interrupt each other
0:19:54 with these kinds of narrative.
0:19:57 Discomfort is one of those things
0:20:02 where it’s good to be transparent about discomfort.
0:20:04 And it starts, again, leaders set the tone.
0:20:06 – Because it’s disarming.
0:20:07 – When you lie, hide and fake.
0:20:10 When you pretend that you got it all figured out.
0:20:11 People will think you got it all figured out.
0:20:15 And so they will pile on more and push you more
0:20:17 and give you more and expect more
0:20:20 because you said everything’s good.
0:20:22 And that’s when it becomes overwhelming.
0:20:25 And that’s when you start blaming management
0:20:26 for mistreating you.
0:20:28 But hold on, right?
0:20:29 Whereas I’m a great believer
0:20:31 in just being totally transparent about discomfort.
0:20:33 And sometimes it’s real
0:20:34 and sometimes it’s perceived.
0:20:36 For example, and I had it happen recently,
0:20:38 one of my team members, she’s wonderful.
0:20:39 We’re a distributed workforce
0:20:41 so we don’t get a lot of face time, right?
0:20:43 So she’s never had a lot of one-on-one time with me.
0:20:45 You know, I see her corporate off-sites and stuff like that.
0:20:46 And I see her on Zoom all the time,
0:20:48 but she’s never had one-on-one time with me.
0:20:50 And so we brought her out to LA
0:20:52 to have a one-day hackathon with me.
0:20:58 She’s young, she’s in her early mid-20s junior employee.
0:21:02 And she came clean.
0:21:04 She said, I just need to tell you,
0:21:06 I was really nervous about today.
0:21:08 I don’t get us a lot of face time with you
0:21:09 and I want to make sure I do right.
0:21:13 And I got really prepared, but I’m really nervous.
0:21:16 And giving me that information was magical
0:21:19 because if she had come in all like ego and everything,
0:21:22 I would have ripped her writing apart a lot more aggressively
0:21:24 because she’s good.
0:21:26 But now I could just be like a little softer
0:21:28 or it’s a doing great.
0:21:29 I can just reinforce
0:21:32 ’cause I know she’s feeling a little intimidated or fragile.
0:21:36 So saying, I’m really excited about this project.
0:21:37 I’m really excited about this new responsibility.
0:21:39 If you’ve given me, I’m a little uncomfortable
0:21:41 because I’ve never had this amount of responsibility.
0:21:42 And I really don’t want to screw it up
0:21:43 and I want to do right by you
0:21:44 and I do want to do right by me.
0:21:46 And I don’t want to fail.
0:21:50 And simply just saying that means that a good leader
0:21:54 will be like, got it, I’m here, you’re good.
0:21:56 And you feel supported in that discomfort.
0:21:58 Yes, right?
0:22:00 Uncomfortable isn’t the problem.
0:22:01 It’s feeling alone and uncomfortable.
0:22:02 That’s the problem.
0:22:03 Yeah.
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0:24:24 – A good leader can see the signs.
0:24:26 Virtual makes it much more difficult.
0:24:27 – Yeah.
0:24:27 – Working in a distributed workforce
0:24:30 makes it much easier to hide.
0:24:34 Lionfake, body language doesn’t come across as easily.
0:24:35 If somebody’s a little bit fidgety,
0:24:36 you can’t really see,
0:24:38 doesn’t really show up on a Zoom call.
0:24:39 But I think discomfort is one of those things
0:24:41 that to learn to be uncomfortable
0:24:43 is probably the single greatest asset you could ever,
0:24:46 you know this, ’cause nobody’s ever achieved anything
0:24:50 in the world did it smoothly.
0:24:54 We all came close to zero if not hitting zero first,
0:24:55 all of us.
0:24:58 And Lionel Richie talks about this.
0:25:01 When he was younger, he had crippling,
0:25:03 debilitating stage fright.
0:25:04 Lionel Richie.
0:25:06 – Yeah.
0:25:08 – And he says, there’s two types of people in this world.
0:25:11 Nobody has the absence of fear.
0:25:13 The two types of people in the world
0:25:15 are those who have fear and they take a step back.
0:25:16 And there are those who have fear
0:25:18 and take the step forward.
0:25:19 And I always took the step forward.
0:25:20 – Yeah.
0:25:22 – Courage isn’t the absence of fear.
0:25:25 It’s being afraid and leaning into it.
0:25:28 And so to be uncomfortable and step forward
0:25:30 is perhaps the single greatest thing you can ever learn.
0:25:31 And what you discover is you’re surrounded
0:25:32 by people who want to help you.
0:25:33 – Yes.
0:25:34 – 100%.
0:25:36 – Which is the most amazing thing to discover.
0:25:37 – This is one of my biggest mistakes.
0:25:39 You know, when I was in my early 20s
0:25:40 and I had my first startup,
0:25:43 I was pleasantly surprised in that it was my first go,
0:25:46 it was dig and it was the first social news app
0:25:49 and it exploded to tens of millions of users in six months.
0:25:50 – Yeah.
0:25:52 – And I was afraid. – That’s uncomfortable.
0:25:55 – Oh my God. Well, here I am in college dropout,
0:25:56 moved to the valley.
0:25:59 I was so intimidated by everyone around me,
0:26:01 the VCs I was getting introduced to everyone else.
0:26:04 And I was scared to raise my hand
0:26:07 and say, I don’t know the answer to this.
0:26:10 Because everyone was looking to me as like someone
0:26:12 that had created something new and exciting.
0:26:14 And it wasn’t until actually two years into the company
0:26:16 where it was really strange.
0:26:17 It was a very small period of time
0:26:19 where dig was bigger, traffic-wise than Facebook.
0:26:22 And so Mark came to my office at Zuckerberg
0:26:25 and he just asked a thousand questions.
0:26:28 And he was really probing me on so many different things
0:26:32 and admitting so many things that he just didn’t know.
0:26:35 And I was like, wow, I need to be more like this.
0:26:36 – Exactly.
0:26:39 – Because here I am operating in the silo.
0:26:40 – Yeah.
0:26:42 – Afraid, ashamed.
0:26:43 And it’s not doing me any good.
0:26:46 I’m actually doing more harm to my business.
0:26:49 And once you have that unlock and you realize
0:26:52 it’s a massive strength to have vulnerability
0:26:53 and to raise your hand and say,
0:26:55 I don’t know the answer to this.
0:26:56 It’s a huge, huge unlock.
0:26:59 – I don’t know is the three most important words
0:27:01 any young entrepreneur can ever wear.
0:27:03 It’s your story, it’s also my story.
0:27:07 I had a small business and I was chief cook and bottle washer
0:27:08 and I started having employees
0:27:09 and I had to be in every meeting
0:27:10 and I had to make every decision.
0:27:12 I thought I had to have every answer.
0:27:15 And if I didn’t, I thought I had to pretend that I did.
0:27:17 And A, the business doesn’t do well with that model.
0:27:19 But B, it’s crippling.
0:27:20 – Yes.
0:27:21 – Like depression set in.
0:27:21 – Oh, 100%.
0:27:24 – Because you feel so alone in the hiding.
0:27:26 And it wasn’t until I learned to say,
0:27:28 I don’t know or can you help me
0:27:31 or learn to accept help when it’s offered.
0:27:33 The amount of help we’re offered on a daily basis,
0:27:37 if you just counted it’s tons to say, I’ll take that.
0:27:38 – Right.
0:27:39 – And it is humiliating by the way.
0:27:41 Like I have some very successful friends
0:27:42 and they asked me what I’m going through
0:27:44 and I’ll just talked about the stuff
0:27:46 that I’m stuck with or don’t know.
0:27:47 And these are very successful people
0:27:49 that I want to look good in front of.
0:27:52 The amazing thing is by being open to them,
0:27:54 the amount that they are there for me,
0:27:56 like that day of humiliation
0:27:58 was the greatest investment I ever made.
0:27:59 – Yeah.
0:28:00 – And I think that’s what you need to think of it as.
0:28:00 Like it’s an investment,
0:28:02 which is when you make an investment,
0:28:04 you pay money, it hurts, you take it out of your bank account,
0:28:06 it was a high number and it was a low number.
0:28:08 And you’re like, oh, this works.
0:28:08 – Yeah.
0:28:09 – It’s an investment.
0:28:10 And sometimes it pays off.
0:28:12 I can’t say that it pays off all the time.
0:28:13 – Sometimes it’s just humiliated.
0:28:14 – Yeah, right.
0:28:15 – But that’s okay.
0:28:15 – And that’s okay.
0:28:16 – Yeah.
0:28:17 What was your personal story?
0:28:18 What was that moment you mentioned
0:28:20 where you didn’t want to go to work anymore?
0:28:22 And then how did you dig yourself out of that?
0:28:25 – Not ironically, I didn’t do it alone.
0:28:27 I reached a point where I didn’t have the skill set
0:28:28 to build the business.
0:28:30 I’d reached a certain level of growth
0:28:32 that I could achieve by myself.
0:28:35 And needing to let go and not be in every meeting
0:28:36 and not make every decision.
0:28:37 That’s a critical point
0:28:39 because you literally can’t grow beyond a certain point
0:28:43 of if only one person can make all the major decisions.
0:28:44 I couldn’t let go.
0:28:48 And so I couldn’t grow, which means frustration.
0:28:49 Didn’t know how to build systems.
0:28:51 Didn’t know how to ask for help.
0:28:52 Ego was out of check.
0:28:54 And I don’t mean like, I thought I was everything.
0:28:57 I mean, I was pretending that I was everything.
0:28:59 And depression set in.
0:29:00 Didn’t want to wake up.
0:29:04 Didn’t find the joy in business ownership anymore.
0:29:06 And was really good at lying, hiding, faking.
0:29:08 I could pretend that I was happier, more in control
0:29:09 and more successful than I felt.
0:29:11 And by the way, so good that nobody could tell.
0:29:14 I mean, I was phenomenal.
0:29:18 And one friend could see through the armor.
0:29:22 One friend came to me and said, “Something’s not right.
0:29:26 “I don’t know what it is, but something feels off.”
0:29:27 And for whatever reason,
0:29:32 probably ’cause she is really good at making a safe space,
0:29:33 I started to open up.
0:29:37 And she didn’t try and fix anything.
0:29:39 She didn’t have suggestions.
0:29:44 She simply let me be vulnerable.
0:29:46 And it’s not the act of being vulnerable per se.
0:29:50 It’s the act of not feeling alone in that vulnerability.
0:29:53 And that she could hold space for me so effectively.
0:29:55 I now had the courage to take all that energy
0:29:56 that I was using to lie, hide and fake.
0:29:59 And I could take that energy to find a solution
0:30:01 to my malaise.
0:30:02 And the solution that I found was sitting right in front
0:30:03 of me the whole time,
0:30:05 which is this thing that I called the golden circle.
0:30:06 And that’s when I made the realization
0:30:07 that I knew what I did.
0:30:09 I knew how I did it, but I didn’t know why.
0:30:12 And that was the reason that I was stuck
0:30:15 as I had no sense of purpose, cause or belief.
0:30:18 And I became obsessed with understanding my why.
0:30:20 I learned my why, but more important,
0:30:22 I learned how to help others find theirs.
0:30:24 And I helped my friends find their ways.
0:30:26 Just because I wanna, it’s like you see a great movie.
0:30:27 You tell your friends to go see it.
0:30:28 – Yeah, yeah.
0:30:29 – No other reason, right?
0:30:30 There’s excitement.
0:30:31 And my friends, they quit their jobs
0:30:32 and started their own businesses
0:30:36 or they found renewed joy in the jobs that they had
0:30:40 to the same levels that I was experiencing, way higher.
0:30:42 And they asked me to talk to their friends
0:30:44 and I would go to someone’s apartment in New York City
0:30:45 and stand in the living room and talk about this thing
0:30:46 called the why and help people find their why
0:30:48 for a hundred bucks on the side.
0:30:51 And my career took a weird turn completely by accident.
0:30:52 – Yeah.
0:30:52 – It was all organic.
0:30:54 But the point to the question was,
0:30:56 it was one person who held space.
0:30:59 We forget that we are social animals
0:31:03 and our very ability to survive
0:31:05 requires the help of other people.
0:31:06 If you fall asleep,
0:31:08 you need someone to watch for wild animals.
0:31:09 – Right.
0:31:10 – We just know good by ourselves.
0:31:12 We can’t solve complex problems by ourselves.
0:31:13 But in groups who are remarkable,
0:31:15 human beings hunted woolly mammoths.
0:31:16 – Yeah.
0:31:19 – No other animal could take down a woolly mammoth.
0:31:22 But we frail, weak human beings could
0:31:26 because the asset that we have that is our superpower
0:31:28 is our ability to cooperate.
0:31:30 And if you know that and you remember that,
0:31:32 that no human being can survive or thrive alone,
0:31:34 that we are fundamentally social animals,
0:31:35 you have to learn to ask for help
0:31:38 and you have to learn to offer it.
0:31:39 And that’s what I did.
0:31:40 That’s where I learned that lesson.
0:31:42 – One of the things that you said that struck me is,
0:31:44 and this is the mistake I make with my wife a lot,
0:31:45 I’ll admit it publicly,
0:31:47 is that I go into problem solving mode.
0:31:50 She’s got an issue and rather than just sit there
0:31:52 and hold space and have some empathy
0:31:54 for what she’s going through
0:31:57 and how it is something that lands on her.
0:31:58 I’m like, let’s fix this, you know,
0:32:00 and I’m like throwing out solutions and all this.
0:32:03 And then that’s not always the best.
0:32:05 – Men are particularly bad at it.
0:32:07 Men are usually in solution mode, not exclusively,
0:32:09 but tends to skew that way.
0:32:10 That’s correct.
0:32:11 That is not a good idea.
0:32:13 There’s a great video on YouTube
0:32:14 called It’s Not About The Nail.
0:32:15 Everybody can go look it up.
0:32:17 It’s one that has a bazillion views.
0:32:19 It’s many years old, but it basically sums it up
0:32:20 absolutely perfectly.
0:32:22 And by the way, you’re the same.
0:32:24 When you have a problem and somebody says,
0:32:25 well, why don’t you do this?
0:32:27 You end up being defensive and fighting with them
0:32:28 because you don’t actually want them to solve the problem.
0:32:31 You just want to feel safe in your stuckness.
0:32:32 And when somebody comes to you and says,
0:32:35 I’m struggling, just go tell me more.
0:32:35 What else?
0:32:37 Boy, by the way, you know how to do this
0:32:40 because you read all the books to do it with your children.
0:32:42 Then when you say, daddy, I’m afraid, that’s okay.
0:32:44 You can be afraid.
0:32:45 But daddy, this, and you’re like, that’s okay.
0:32:47 You don’t try and fix their fear.
0:32:48 You hold space for their fear.
0:32:51 When they’re nervous, you don’t try and fix their nervousness.
0:32:52 You don’t have to be nervous.
0:32:53 Don’t be nervous.
0:32:54 We’ve learned that that’s a terrible thing to do
0:32:55 with children.
0:32:57 You go, oh, I know, it’s scary.
0:32:59 You affirm the feelings.
0:33:01 Well, why did you stop doing that?
0:33:03 Just because somebody’s an adult?
0:33:04 Like you still have to affirm their feelings.
0:33:05 – It’s a great point.
0:33:06 – Honey, I’m nervous.
0:33:07 Honey, I’m scared.
0:33:08 Honey, I’m confused.
0:33:09 Honey, I’m angry.
0:33:10 – Yeah.
0:33:12 – My girlfriend and I were,
0:33:13 she said something about something
0:33:16 and I had done something that upset her.
0:33:19 And I basically was like, well, that’s ridiculous.
0:33:20 And clearly, I didn’t mean to.
0:33:21 How can you say that I did that?
0:33:23 Of course, I didn’t do that on purpose.
0:33:24 – Right.
0:33:25 – You know, I’m in full on defense mode.
0:33:28 I’m in full on like, it’s not really gaslighting,
0:33:29 but it’s a form of gaslighting,
0:33:30 which is like I’m saying,
0:33:32 you can’t feel that way about that.
0:33:33 – Right.
0:33:34 – Right?
0:33:38 And after many rounds, I finally said,
0:33:40 if I were in your shoes, I would have felt the same.
0:33:41 – Mm.
0:33:42 – And she said, thank you.
0:33:43 – Yeah.
0:33:45 – And the funny thing is what preceded that was,
0:33:46 I just need you to see it.
0:33:47 What if you were me?
0:33:49 Like she literally gave me the instruction.
0:33:50 – Right.
0:33:51 – I’m like, well, if I were in your shoes,
0:33:52 yeah, I probably would have felt the same
0:33:53 where you’re feeling now.
0:33:54 – Right.
0:33:55 – That was it.
0:33:55 – No, you’re right.
0:33:56 – Argument over.
0:33:57 – I’ve been there.
0:33:58 I’ve been in this exact conversation.
0:33:59 – Yeah.
0:34:00 – 100%.
0:34:02 – I’ve had it happen where I’m in a bad place
0:34:03 and I call a friend and tell them basically like,
0:34:04 hey, I’m not feeling good.
0:34:06 And they start fixing and I get off the phone.
0:34:07 – Yeah.
0:34:08 – ‘Cause they make it worse.
0:34:10 – So true.
0:34:11 I talk about this a lot,
0:34:13 which is the idea of sitting in mud,
0:34:17 which is when we or our people we love are in a bad place,
0:34:18 they’re sitting in mud.
0:34:19 – Mm-hmm.
0:34:20 – And our instincts, well-intentioned,
0:34:21 is to pull them out of the mud.
0:34:22 – Sure.
0:34:22 – Right, to fix it.
0:34:24 Oh my God, that looks horrible.
0:34:25 Nobody wants to be in mud.
0:34:26 Let me pull you out of the mud.
0:34:27 And they don’t want to be pulled out of the mud.
0:34:28 – Right.
0:34:30 – But they don’t want you standing on the sidelines.
0:34:32 What they want, what loving friendship,
0:34:33 what loving relationship means is,
0:34:36 I’m gonna come and sit in the mud with you.
0:34:37 – Yeah.
0:34:37 – I don’t want to sit in the mud with you.
0:34:39 It’s no fun being in the mud with you,
0:34:41 but I’m gonna get in the mud with you.
0:34:44 – Well, that act alone will allow them to dig theirself
0:34:45 or climb their way out of the mud.
0:34:47 – Or turn to you and say,
0:34:48 I think I’m ready to get out of the mud.
0:34:49 – Yeah.
0:34:50 – And then you can go into solution mode.
0:34:52 If a friend is depressed,
0:34:54 they just don’t want to get out of bed.
0:34:55 And we can’t make them get out of bed
0:34:57 and tell them they have to get out of bed.
0:34:59 Go to their house and get into bed with them
0:35:03 and watch TV, watch movies all day, be depressed with them.
0:35:04 It’s not fun.
0:35:07 It’s not productive, but it makes them feel not alone.
0:35:08 – Right.
0:35:12 You’re matching their spirit at the moment.
0:35:13 – You’re making them feel not alone.
0:35:14 – Yeah.
0:35:16 – And usually when we try and fix someone’s problem,
0:35:19 usually when we try and pull them out of the mud,
0:35:20 what that makes them feel
0:35:22 is that they’re in the mud by themselves.
0:35:26 ‘Cause we’re standing on high ground, on dry ground,
0:35:27 saying, “Let me pull you out.”
0:35:28 – Right.
0:35:30 – Oh my God, look at you down there in the mud.
0:35:31 Let me pull you up here to the dry land,
0:35:34 which all that does is remind them that they’re alone.
0:35:34 – Right.
0:35:38 You must have just given everything
0:35:40 that you’ve been through in all your talks.
0:35:42 I’d imagine people come up to you randomly
0:35:45 or at talks after talking to the line forms
0:35:47 and people want to ask you questions.
0:35:51 If a young person comes to you looking to be pulled out
0:35:52 or in some way it’s like, “Give me advice on this,”
0:35:56 or that, “How do you empower them to make their own decisions?
0:36:00 How do you equip them to figure out their why?”
0:36:03 ‘Cause I’d imagine you can’t do that in two minutes.
0:36:05 – You can.
0:36:06 – Tell me.
0:36:08 – So finding the why is the easy part.
0:36:11 It’s like college graduation is called commencement.
0:36:12 – Yeah. – Beginning of something?
0:36:13 – Yeah.
0:36:14 – Well, finding your why is easy.
0:36:16 That’s why I called the book “Start With Why,”
0:36:18 ’cause once you have it, now the work begins.
0:36:19 – Right.
0:36:21 – So again, there’s two questions there.
0:36:23 One is how to find the why and which I’ll tell you.
0:36:26 And the one is when you’re coming up to a stranger,
0:36:28 I mean, they don’t know me and I don’t know them.
0:36:29 And they come up to me and say,
0:36:31 “Can you help me get out of this?”
0:36:32 Or, you know, hey.
0:36:33 – Right.
0:36:34 – And my answer is always the same is,
0:36:35 you don’t know me.
0:36:37 You know the image of me.
0:36:39 You know the image you’ve built of me.
0:36:42 I could be the worst qualified person to help you with this.
0:36:44 Go ask somebody who actually cares about you.
0:36:46 You know, you’re not my friend.
0:36:48 Like, I like you, you ever seem very nice,
0:36:50 but why would I get into mud with a stranger?
0:36:52 – Right. – I don’t know you.
0:36:54 You know, go ask somebody who loves you
0:36:57 because it’s safer to be vulnerable with me
0:36:58 because I’m a stranger.
0:36:59 – Right.
0:37:00 – It’s hard to be vulnerable
0:37:02 with somebody who actually knows us,
0:37:04 but that’s the thing you gotta do.
0:37:05 – Yes.
0:37:06 – They’re asking the wrong person.
0:37:09 I’m sympathetic, but I’m the wrong person.
0:37:09 – Yeah.
0:37:12 – So where does a therapist fall on that?
0:37:13 Because you don’t know them,
0:37:16 but yet you can be vulnerable around them.
0:37:19 How do they fit into your thinking?
0:37:21 Like, obviously it’s a useful tool to have a therapist.
0:37:24 – Therapists have said that I professionally
0:37:26 hold space for you, that is my job.
0:37:27 – Right.
0:37:28 – Depending on the therapist,
0:37:30 some of them have tools to help you
0:37:31 with whatever you’re dealing with, right?
0:37:33 So they can equip you with tools.
0:37:36 And I think therapists are one of the things that we need.
0:37:38 I don’t think they’re the only thing that we need.
0:37:40 I believe in therapy, I think it’s a good thing.
0:37:42 And the practice of being open with someone.
0:37:44 But I hope that you use that skill set with your friends.
0:37:46 Like, what’s the point of learning the skill
0:37:48 if you’re not gonna apply it in other places?
0:37:49 And I think somebody who really struggles
0:37:51 with vulnerability should do therapy
0:37:55 because it is a good way to practice being vulnerable
0:37:58 with the people you really need to be vulnerable.
0:38:00 If you’re only vulnerable with your therapist and no one else,
0:38:02 I think that’s as much of a problem
0:38:03 as not being vulnerable to anybody.
0:38:06 It’s an education as much as a catharsis.
0:38:07 – Right.
0:38:08 – So going back to your question about finding your one.
0:38:09 – Yes.
0:38:10 – Okay.
0:38:11 I’ll give you two answers.
0:38:11 – Okay.
0:38:13 – There are many ways to do it.
0:38:14 We’ve tried to make many tools available.
0:38:16 We have things in our website
0:38:18 that people can do to find their why.
0:38:20 I wrote a book called “Find Your One.”
0:38:20 – Yeah.
0:38:22 Your website’s got some great thank courses
0:38:24 and things that people can sign up for,
0:38:25 which look awesome.
0:38:26 – Thank you.
0:38:28 – But there’s something called the friends exercise,
0:38:30 which anybody can do, and it’s fun.
0:38:32 Basically find a friend who loves you and you love them.
0:38:34 The kind of friend who,
0:38:35 if you call them at three o’clock in the morning,
0:38:36 you know that they would be there for you
0:38:37 and you would be there for them.
0:38:38 – Okay.
0:38:40 – Do not do this exercise with a spouse,
0:38:41 with a sibling, with a parent.
0:38:42 It does not work.
0:38:44 Those relationships are too close.
0:38:45 – Okay.
0:38:46 – Do it with a best friend.
0:38:48 And ask them the simple question.
0:38:49 Why are we friends?
0:38:52 And they’re gonna look at you like you’re crazy.
0:38:53 Because the part of the brain that controls
0:38:56 all of our feelings, love, loyalty, trust,
0:38:58 the limbic brain, doesn’t control language.
0:39:00 It doesn’t control rational thought.
0:39:01 – Hmm.
0:39:02 – And so it’s very hard for us
0:39:05 to rationally articulate emotions,
0:39:07 which is why we use metaphors.
0:39:08 – Yeah.
0:39:08 You’re hard tempering him in the words.
0:39:09 – Yeah, of course.
0:39:10 It’s a biological problem.
0:39:12 And so then you immediately convert the question,
0:39:14 because why is an emotional question?
0:39:16 And you start saying, come on, come on.
0:39:19 What, what specifically is it about me
0:39:22 that I know that you would be there for me no matter what?
0:39:23 And again, they’re gonna hem and ha,
0:39:24 it’s very hard to put them to words.
0:39:25 – What if they just give you high level like,
0:39:26 oh, you’re funny? – They will.
0:39:27 They will.
0:39:28 That’s what they will do.
0:39:28 They’ll start describing you.
0:39:32 You’re funny, I trust you, you’re always there for me.
0:39:33 And you have to play devil’s advocate.
0:39:35 Great, that’s the definition of friend.
0:39:37 What specifically is it about me?
0:39:39 Or great, yes, all true.
0:39:41 But you get that from lots of other people.
0:39:43 What specifically is it about me?
0:39:45 Then I know you’d be there for me no matter what.
0:39:47 And they’re gonna go through a few rounds of this
0:39:48 where they’re just describing you
0:39:52 and describing this generic best friend archetype.
0:39:56 And eventually, because of discomfort, they will give up.
0:39:59 And they’ll go, look, man, I don’t know.
0:40:02 All I know is, and they’ll start describing themselves.
0:40:04 And this is what my friend said to me
0:40:04 when I did the exercise.
0:40:06 Look Simon, I don’t know.
0:40:09 All I know is, I can sit in a room with you.
0:40:11 I don’t even have to talk to you when I feel inspired.
0:40:13 And I got goosebumps.
0:40:15 So what they’ll do is they’ll say something
0:40:18 about themselves and you will have an emotional reaction.
0:40:20 You’ll get goosebumps, you’ll wail up with tears,
0:40:21 because what they’re doing is articulating the value
0:40:24 having their life, which is the thing you give
0:40:26 to the world, which is your why.
0:40:27 And if you do this with multiple friends,
0:40:30 you will get very similar, if not the exact same answer,
0:40:31 because who you are in the world
0:40:35 is the space you fill in all of these people’s lives.
0:40:37 – And so is this idea what you give to them
0:40:38 or what you give to the world,
0:40:41 are you looking for a cross-section of agreement
0:40:42 amongst friends?
0:40:43 – No, no, no, no, no, no, no, no, no.
0:40:45 This is not subjective, this is objective.
0:40:46 – Okay.
0:40:47 – Find as there’s common themes.
0:40:50 And your why is the value you have in the world.
0:40:51 It’s why not everybody likes you.
0:40:53 It’s not everybody wants what you have.
0:40:54 There are plenty of people who think
0:40:57 that my entire existence is cheesy.
0:40:58 I mean, I talk about inspiration.
0:41:01 I mean, literally what could be cheesier, right?
0:41:02 And they’re very dismissive.
0:41:03 Well, I’m not for them.
0:41:04 That’s okay.
0:41:05 It’s like some people like chocolate,
0:41:05 some people like vanilla.
0:41:06 It’s all good.
0:41:08 But the people who love what I have to offer,
0:41:12 well, those people are either part of the movement.
0:41:15 They either, you know, buy a, read a book
0:41:17 or watch a video or they’re my friends.
0:41:19 And we’re all kind of the same kind of person.
0:41:21 It’s like when Apple says think different,
0:41:22 who are they describing?
0:41:23 The answer is yes.
0:41:24 – Yeah.
0:41:25 – They’re describing their employees.
0:41:26 They’re describing their founders.
0:41:27 They’re describing their customers.
0:41:30 They’re describing, the answer is yes.
0:41:33 They’re describing everyone who believes in that thing.
0:41:34 Well, it’s the same.
0:41:35 Your why is the thing you give to the world
0:41:37 and the people who value that
0:41:38 are the ones who want to receive it.
0:41:39 But it’s always going to be you.
0:41:42 – Can we have different whys, multiple whys?
0:41:44 When do these whys form?
0:41:46 – Your why is fully formed by your mid to late teens.
0:41:48 The youngest why discovery I ever did
0:41:50 was a 16 year old and it worked perfectly.
0:41:53 – We are all the products of our upbringing.
0:41:55 You are who you are based on the experiences you had
0:41:57 when you were young, which made you quote unquote,
0:41:58 who you are.
0:42:01 And you don’t have a why for work and a why for home
0:42:03 because then how would I know which one’s the real you?
0:42:06 And one of those two places you’re lying, right?
0:42:08 And you can’t change your why every year
0:42:09 because then again, how would you ever form trusting
0:42:11 relationships because I’d never know who you are.
0:42:13 Are you authentic this week?
0:42:14 But last week was a different why,
0:42:16 so it’s the concept of authenticity
0:42:19 literally couldn’t exist if your why could change.
0:42:20 You are who you are and the rest of your life
0:42:22 is simply an opportunity to live in balance
0:42:23 with that why or not.
0:42:26 I’ll show you another way to find your why,
0:42:27 which is pattern recognition.
0:42:31 I want you to tell me something you’ve done in your career,
0:42:32 whether it was commercially successful or not,
0:42:34 does not matter.
0:42:35 But something, a project you’ve worked on,
0:42:37 something specific that you did in your career
0:42:40 that you absolutely loved being a part of.
0:42:43 And if everything you ever did for the rest of your life
0:42:44 was like this one thing,
0:42:45 you’d be the happiest person in life.
0:42:47 – Oh.
0:42:50 – I would say one of the things that I’ve enjoyed is–
0:42:51 – Loved.
0:42:53 – Loved, okay.
0:42:55 One of the things that I’ve loved is,
0:42:57 then this is probably ego loaded,
0:42:58 so let’s just take it with that.
0:43:03 So I’ve loved getting the recognition from others
0:43:05 for discovering things earlier than anyone else.
0:43:08 Tell me something specific that you did
0:43:12 that you loved the process, you loved being a part of it,
0:43:14 that if all of your projects were like this one,
0:43:16 ’cause you’ve started multiple business,
0:43:19 many of them have had commercial success,
0:43:21 some of them you enjoyed more than others,
0:43:24 and within those projects, there were things that happened.
0:43:25 – Sure.
0:43:26 – Things that went right or wrong,
0:43:27 new clients you landed, whatever it was.
0:43:31 Tell me one specific thing throughout this entire career
0:43:33 that you loved, you didn’t necessarily like it ever,
0:43:36 but you loved every, like this is the most exciting thing.
0:43:40 – I would say that is the invention of things that–
0:43:42 – Specific, invention of what?
0:43:45 – When we created social voting for the first time
0:43:48 and you could see the number go up
0:43:51 on a piece of content on the web, this is before likes,
0:43:54 and because of something called asynchronous JavaScript,
0:43:57 you could actually watch as people socially voted
0:44:00 on things in real time, and inventing that,
0:44:04 and seeing that come to life, and watching humans
0:44:07 in real time gather around articles
0:44:11 and watch them socially spread information,
0:44:16 that moment of creating that and seeing it take off
0:44:20 was just the creation process was a highlight
0:44:22 you would probably never get anywhere else.
0:44:27 That was a great just accomplishment for me and my team.
0:44:29 – So of all the amazing things you’ve done,
0:44:31 and you’ve had exits, and all of the things
0:44:33 that people dream of, right?
0:44:35 What specifically was it about that,
0:44:40 about social voting that stands out in an entire career?
0:44:42 – I think it’s because historically,
0:44:43 my kids will look back on that and said,
0:44:47 dad did something that changed the world in some small way.
0:44:48 Could say that about other things you’ve done,
0:44:49 dad did something with dig,
0:44:52 dad did something with all those things.
0:44:54 My dad did was precursor to this or precursor to that.
0:44:57 Mark Zuckerberg came to my dad for advice.
0:45:01 So that, what specifically was about social voting
0:45:01 that was so exciting?
0:45:03 – Probably because it had the biggest impact.
0:45:05 I would say there’s been other things,
0:45:07 like when I made the first intermittent fasting app,
0:45:10 severely obese people, my dad died of a heart attack,
0:45:11 were losing a lot of weight,
0:45:14 and we started getting emails saying it changed their lives.
0:45:18 And that was another aha moment where I was like,
0:45:20 this makes me feel so good.
0:45:22 Just because I know that I’d give anything
0:45:23 for another year with my dad,
0:45:26 and to like think that I’m giving somebody else’s son
0:45:29 or daughter an extra year with their mom or dad
0:45:31 is a huge one for me.
0:45:33 So I think that’s another huge one.
0:45:35 – No, that’s good.
0:45:37 Tell me an early specific happy childhood memory,
0:45:38 something I can relive with you.
0:45:40 – Saturday mornings, my dad–
0:45:41 – One memory.
0:45:45 – One memory, catching a fish with my dad out on a boat.
0:45:47 – So this is a specific time you were at?
0:45:48 – Yeah, 100%.
0:45:50 – Okay, tell me about that day.
0:45:52 – Got up early, I had never been fishing in the sea,
0:45:54 only kind of on lakes.
0:45:58 My dad drove me about, it was a multi-day trip
0:45:59 to get up to the state of Washington.
0:46:03 When we went out on a boat, I was probably 10 years old,
0:46:07 and I helped reel in like a 45 pound salmon.
0:46:10 I obviously couldn’t do it myself, ’cause I was tiny.
0:46:11 – Actually, I take that back.
0:46:14 A better memory was laying in the back of our truck bed,
0:46:15 looking up at my dad,
0:46:17 he showed me satellites for the first time,
0:46:19 and I saw a satellite camping with my dad.
0:46:21 That was like just a magical moment.
0:46:22 – Okay, tell me more about that.
0:46:24 – I just realized how much I love my father,
0:46:26 and I just realized how special it was
0:46:28 that I got to spend some one-on-one time with him,
0:46:31 and that he would take time out of his busy schedule
0:46:34 to show me attention, to teach me things.
0:46:36 It was difficult because my dad
0:46:38 was a very verbally abusive father to my mom,
0:46:40 and so he was always angry.
0:46:44 And so to see him being tender with me
0:46:47 was just a beautiful thing,
0:46:49 because I got to see my dad in a place of like,
0:46:52 happiness, which I didn’t see that often.
0:46:53 – Yeah.
0:46:56 And what was it about showing you the satellites?
0:46:57 – More one-on-one time,
0:47:00 and I just didn’t even know those things existed.
0:47:02 My late 40s, satellites were a big deal
0:47:03 way back in the day,
0:47:04 and now I will go watch SpaceX launches
0:47:06 outside of my balcony.
0:47:07 But back then it was like,
0:47:09 I just didn’t even know you could see them with a naked eye.
0:47:11 And if you’re laying on a clear enough night,
0:47:13 you can look up and you can actually track them
0:47:14 and see a satellite, which is amazing.
0:47:16 – Yeah.
0:47:18 Okay, so what’s interesting about those stories,
0:47:20 seeing satellites with your dad,
0:47:22 and when you talk about the intermittent fasting,
0:47:26 you use very similar language in both of them,
0:47:28 which is you talk about the opportunity
0:47:30 to have these moments, right?
0:47:31 My dad was an angry man,
0:47:33 and I got to see him in tender times.
0:47:35 You talk about giving somebody else
0:47:38 the opportunity to spend more time with, right?
0:47:40 It’s about the discovery of beautiful things
0:47:42 that you didn’t know existed,
0:47:43 an angry man who could be tender,
0:47:46 a satellite you didn’t know you could see with a naked eye,
0:47:49 the discovery of changing an intermittent fast,
0:47:51 even the uploading of things.
0:47:55 It’s really about recognizing that there’s community,
0:47:57 like there’s other people who connect.
0:48:02 And I think your why sort of exists in this arena.
0:48:04 I’m struggling to find the exact words for it.
0:48:05 – Yes, that feels right to me.
0:48:07 It’s very right to me.
0:48:09 – Where the things that bring you joy
0:48:11 are when you give somebody the opportunity
0:48:14 to make a discovery that has a positive impact in their lives.
0:48:15 – 100%.
0:48:16 – To see something they didn’t see before.
0:48:17 – And in all of those examples,
0:48:20 there was an element of like, I didn’t know that before.
0:48:22 I had never seen that before.
0:48:23 I didn’t know that could have an impact.
0:48:24 And there was a positive impact
0:48:26 whether it’s spending time with your dad.
0:48:27 And you said it beautifully,
0:48:28 which is giving somebody the opportunity
0:48:31 to spend more time with their mother or father
0:48:33 that you didn’t have.
0:48:34 And to some degree,
0:48:36 you’re becoming the best parts of your father,
0:48:39 which is to take quiet moments,
0:48:40 show somebody something
0:48:42 and let them discover something magical.
0:48:44 – Yeah, I think that’s why I like playing with my kids so much.
0:48:46 – The things you get to show your kids.
0:48:47 – Yeah, and see through their eyes.
0:48:48 – See through their eyes.
0:48:49 – Yeah, it’s beautiful.
0:48:50 – It’s beautiful.
0:48:52 And even in the way you talk about social voting,
0:48:55 which is to see through other people’s eyes
0:48:57 what they find interesting.
0:48:59 So there’s discovery for the person
0:49:00 who’s learning it for the first time,
0:49:01 but there’s discovery for you who’s teaching them
0:49:03 because you don’t know where it’s gonna go.
0:49:04 – Right.
0:49:05 – And so there’s discovery on both sides.
0:49:06 – Yeah.
0:49:07 – So I think discover or discovery
0:49:10 is sort of your magic place, your magical place.
0:49:11 Anyway, your why exists somewhere in the–
0:49:12 – No, that’s awesome.
0:49:14 I do wanna talk about like what you do professionally
0:49:16 for people because I think this is important.
0:49:18 I noticed your site has some ways
0:49:19 that people can sign up
0:49:22 and actually learn how to be coached through this.
0:49:24 More people need to do that.
0:49:25 And I wanna take it further now.
0:49:27 What do people do on your site?
0:49:29 – So we started the optimism company
0:49:30 with a very specific purpose,
0:49:33 which is to advance the idea of human skills.
0:49:35 I hate the term soft skills.
0:49:36 Hard skills and soft skills.
0:49:38 First of all, hard and softer opposites.
0:49:40 These things do not work against each other.
0:49:43 And also there’s nothing soft about soft skills.
0:49:45 They’re hard skills and there’s human skills.
0:49:46 Hard skills are the skills you need to learn
0:49:48 to do the job you need to do.
0:49:50 And human skills are the skills you need to learn
0:49:51 to be a better human being.
0:49:54 And there’s a great irony in being human, right?
0:49:56 Like cats don’t have to work very hard to be cats.
0:49:58 They’re just naturally good at being cats.
0:50:00 But we have to actually do a lot of work
0:50:01 to be good human beings.
0:50:03 It’s frustrating and annoying.
0:50:05 And we built the optimism company
0:50:08 to completely focus on teaching people
0:50:12 the human skills they need to be better human beings
0:50:15 and to advance that ability to cooperate and socialize.
0:50:17 – Is that both personally and professionally?
0:50:18 – It’s you, right?
0:50:20 So when I teach you better listening skills,
0:50:23 when I teach you how to have a difficult conversation,
0:50:26 when I teach you how to have an effective confrontation.
0:50:28 Now we teach it in a work context
0:50:30 because that’s where the people are.
0:50:32 But the reality is those skills are useful everywhere.
0:50:34 I like to make the joke that there’s an entire section
0:50:36 of the bookshop called self-help.
0:50:39 And there’s no section of the bookshop called help others.
0:50:41 And what we need is to advance the help others industry.
0:50:43 And that starts with teaching people the human skills
0:50:46 of how to not only be a better version of yourself,
0:50:50 but more important, which is how to be a good partner,
0:50:54 friend, colleague, coworker, boyfriend, girlfriend,
0:50:55 brother, sister, son, daughter,
0:50:57 mother, father, to somebody else.
0:51:02 Because all of these relationships, boss, employee, dad,
0:51:05 mom, brother, sister, they’re all cooperative.
0:51:07 None of them are solo.
0:51:09 They all involve a relationship.
0:51:10 Almost every label we have for people
0:51:12 involves some sort of relationship.
0:51:14 You can’t be a leader if nobody’s following you.
0:51:17 You can’t be a follower if there’s nothing to follow.
0:51:18 All of these things is a relationship,
0:51:20 even when people talk about their faith.
0:51:21 I’m a follower of X.
0:51:22 Well, that’s a relationship.
0:51:24 That’s how they describe faith.
0:51:27 And so that’s what the optimism is singularly focused on,
0:51:28 which is how we teach people the human skills
0:51:29 to be better human beings.
0:51:30 – That’s awesome.
0:51:32 I was picking through the website
0:51:35 and I noticed there was a couple of things
0:51:38 you mentioned on the site that you teach people
0:51:41 the courage to lead and then also conflict resolution.
0:51:44 How do you teach someone to resolve conflict?
0:51:46 – So many of these skills,
0:51:49 the foundational skill of a lot of them is listening, right?
0:51:51 Like we talked about it before with you and your wife.
0:51:52 You fix everything.
0:51:54 One of what you need to do is learn to listen.
0:51:57 You work really hard to learn to listen to your kids,
0:51:59 but then you abandon the skill at work
0:52:02 or in your adult relationships, right?
0:52:05 And so conflict resolution, we have conflict at work.
0:52:06 We have disagreements.
0:52:07 We have misunderstandings.
0:52:09 We feel triggered by certain things that people say,
0:52:11 whether they said it on purpose or by accident,
0:52:14 we feel pressure, we react badly.
0:52:16 There’s conflict everywhere.
0:52:19 And I don’t believe that world peace, for example,
0:52:21 is the absence of conflict.
0:52:23 I think that’s nonsense, right?
0:52:26 We live in a world with no conflict or war.
0:52:28 Nope, not gonna happen, right?
0:52:30 To me, world peace is the ability
0:52:32 to resolve conflict peacefully.
0:52:36 There’s gonna be conflict on how to resolve it peacefully.
0:52:36 And you see it at work all the time.
0:52:38 People yell at each other, people quit out of anger,
0:52:40 people fire out of anger.
0:52:42 Conflict is gonna happen.
0:52:44 How do we resolve our conflicts peacefully?
0:52:45 You’re gonna have conflict in your relationships.
0:52:47 How do you resolve conflict peacefully?
0:52:51 So for me, conflict resolution is that very difficult skill
0:52:52 of when you’re angry,
0:52:54 you still have the skill to hold space for somebody else.
0:52:57 – That’s so hard because when someone is triggered,
0:52:58 everything goes out the window.
0:53:00 And it’s just like, all of a sudden it’s all about emotion.
0:53:03 How do you train yourself to say,
0:53:06 let me pause this emotion and set it aside for a second
0:53:08 and listen, what’s the process like?
0:53:09 – Part of it is you have to have a game plan
0:53:10 going into every conflict.
0:53:11 You wanna make these decisions
0:53:13 before you get to conflict.
0:53:14 You don’t wanna be in conflict
0:53:16 and then having to come up with strategy.
0:53:17 You need to master these skills
0:53:19 before the conflict so you’re prepared.
0:53:20 Whether they’re athletes or military,
0:53:21 they talk about muscle memory.
0:53:22 You practice and practice and practice
0:53:23 and practice and practice.
0:53:25 So you don’t quote unquote have to think
0:53:26 in the stressful time
0:53:29 because you can just quote unquote rely on your training.
0:53:30 – Interesting.
0:53:31 – Very similar.
0:53:32 – So you offer that type of training?
0:53:34 – Well, I mean, if you do these kinds of trainings,
0:53:37 then you’re doing them in artificial environments.
0:53:38 – Is it role-playing?
0:53:39 What type of training is it?
0:53:41 – The role-playing, we expect people to go do themselves.
0:53:42 But the point is all of these things,
0:53:44 even if you learn the skill, you have to go practice it.
0:53:45 So I’ll give you one example.
0:53:49 My girlfriend, we talk to each other very openly
0:53:53 when we’re not in conflict, that when we fight,
0:53:55 we don’t want it to be me versus you.
0:53:57 We want it to be us versus the problem, right?
0:53:58 So we know that.
0:54:00 So both of us have that mindset.
0:54:04 So when conflict does arise, we both have the right mindset
0:54:06 and sometimes it takes us a little to get back to it
0:54:08 or we can say to each other, “Hey, hey, hey,
0:54:10 “I’m not trying to be right here.
0:54:11 “I’m trying to solve this problem.”
0:54:12 And then we might see the person.
0:54:13 But I’ll give you a real-life example
0:54:15 that actually happened where we went down
0:54:18 that horrible rabbit hole of who started it.
0:54:20 If you hadn’t done this, then I wouldn’t have done that.
0:54:21 Well, if you hadn’t done that,
0:54:22 then I wouldn’t have done this.
0:54:23 It sounds like some Middle East conflict,
0:54:25 which is like we’re both blaming each other
0:54:26 for where it started.
0:54:29 And it was getting worse and worse and worse
0:54:31 and more aggressive.
0:54:33 And it occurred to me in that fight,
0:54:34 this is going nowhere.
0:54:36 This is intractable.
0:54:39 This is going to end up on you on the couch or something.
0:54:40 One of us is going to storm out.
0:54:42 If you just flash forward 10 minutes,
0:54:46 there’s no peaceful resolution to this journey we’re on
0:54:48 where we’re pointing out what I did right
0:54:49 and what she did wrong
0:54:50 and she’s pointing out what I did wrong
0:54:52 and what she did right.
0:54:53 Right?
0:54:54 And I literally interrupted.
0:54:58 I said, “Okay, this is going nowhere, new rules.
0:54:59 “We’re going to reverse the script here
0:55:01 “because right now I’m pointing out everything
0:55:02 “I’m doing right and you’re doing wrong
0:55:04 “and you’re doing the same, new rules.
0:55:07 “From now on, I’m going to tell you what I did wrong
0:55:10 “and what you did right and I’ll go first.”
0:55:11 Wow.
0:55:12 And I said, “Here’s what I did wrong
0:55:14 “and here’s what you got right.”
0:55:16 And she goes, “Well, yeah, here’s what I got wrong
0:55:17 “and here’s what you got right.”
0:55:17 That’s beautiful.
0:55:18 And I said, “Well, here’s what I got wrong
0:55:20 “and you got right.”
0:55:25 And in five minutes or less, the tension had been released.
0:55:28 We realized that both of us were trying.
0:55:29 Neither of us was evil.
0:55:32 Both of us were doing things right
0:55:35 and both of us had accountability.
0:55:37 And in that moment, it just petered out.
0:55:38 That’s beautiful.
0:55:40 You’re taking the knob and just turning it down enough
0:55:43 to where you can have a sensible conversation again.
0:55:44 But I created rules.
0:55:45 Yes.
0:55:47 The rules of engagement are this.
0:55:49 We’re going to continue to fight,
0:55:52 but we are operating from this script.
0:55:53 Me right, you wrong.
0:55:54 I’m just going to flip the script.
0:55:56 Me wrong, you right.
0:55:57 And let’s just see what happens.
0:55:59 Do you use that every time or is that just–
0:55:59 No, I didn’t.
0:56:00 That was spontaneous in the moment.
0:56:01 That’s amazing.
0:56:02 I’ve never done that before.
0:56:03 I’m going to do it again.
0:56:04 Yeah.
0:56:08 But the point is, is like doing it once even,
0:56:10 the next time you go down that path,
0:56:13 I don’t have to go down the path and get it really tense
0:56:15 ’cause I can stop it immediately like look,
0:56:16 I hear what you’re saying
0:56:18 and I definitely have some culpability here.
0:56:19 Yeah.
0:56:21 I definitely did this wrong and you did this right.
0:56:23 I can do it immediately now.
0:56:24 But the point is, these are skills.
0:56:25 Right.
0:56:27 Learnable, practicable skills and they’re muscles.
0:56:30 If you don’t use them, they’re going to atrophy.
0:56:31 And this is what we’re trying to teach.
0:56:34 We’re trying to teach a host of these skills
0:56:37 that by themselves, they’ll help a little bit.
0:56:39 But the more of these skills we master,
0:56:41 the better colleagues,
0:56:43 yeah, girlfriends, girlfriends, brothers, sisters,
0:56:46 fathers, mothers, sons, daughters, leaders, employees,
0:56:49 the better we become team members, colleagues,
0:56:51 any kind of human relationship.
0:56:53 It was a big blind spot for me for a long time,
0:56:56 which is I was a computer geek as a kid.
0:56:59 So back in our day, it was not cool to be a computer geek.
0:57:00 So I was made fun of a lot.
0:57:04 So I was socially awkward and I had a really hard time
0:57:06 getting into my teens and then twenties,
0:57:10 going into a new situation without applying alcohol
0:57:13 because alcohol for me was like a crutch, right?
0:57:14 I’ve since course corrected that,
0:57:17 but I’ve had to realize that when I stopped alcohol,
0:57:19 I have to build new muscles again.
0:57:22 I have to build new muscles around social interactions.
0:57:23 One on one, I’m fine.
0:57:25 I can turn it on for a while and I’m fine.
0:57:29 But there’s things that you have to kind of figure out
0:57:31 how to build that muscle around
0:57:34 so you can become proficient in it.
0:57:38 When you meet someone that is like, I’m socially awkward,
0:57:42 I am not advancing my career,
0:57:43 the classic one is afraid to ask for a raise,
0:57:45 but let’s just say I’m not outgoing enough
0:57:50 to inspire confidence by the leaders in my organization.
0:57:52 Is that something that you believe
0:57:54 that we can learn and improve upon?
0:57:57 – So social awkwardness is not the problem.
0:57:59 Un-discomfort asking for difficult things
0:58:00 is not the problem.
0:58:01 I’m socially awkward.
0:58:02 You see me in a crowd, I’m useless,
0:58:03 I’m the one standing in the corner.
0:58:04 – So am I.
0:58:07 – I’m an over-sharer, mainly out of discomfort.
0:58:10 Talk too much, come on too strong.
0:58:12 It’s all discomfort.
0:58:13 Years of failed dates, you know?
0:58:14 – Yeah.
0:58:16 – Just social awkwardness.
0:58:21 And what I’ve learned is that those are not the problems.
0:58:23 The problem is confidence.
0:58:28 And I use social awkwardness or ADHD or introversion
0:58:33 or one of these excuses for whatever weirdness that I feel.
0:58:36 And I’m a great believer
0:58:38 that none of these things are right or wrong.
0:58:40 They just are, you know?
0:58:41 You can be socially awkward as an extrovert,
0:58:43 you can be socially awkward as an introvert.
0:58:44 They just are.
0:58:45 And again, it goes back to asking for help
0:58:47 and just owning it, right?
0:58:48 Let’s be vulnerable.
0:58:51 Let’s be open about our social awkwardness.
0:58:52 Let’s put it out there, let’s let people know.
0:58:53 I say it all the time,
0:58:54 like I’m really socially awkward.
0:58:58 I say it on dates, it’s a release, right?
0:58:58 It’s like putting it on the table.
0:59:00 So if I have a moment,
0:59:02 I’m not beating myself up in my head, right?
0:59:03 – Which can compound, right?
0:59:04 – And now it’s all me.
0:59:06 It’s all me in my narrative, right?
0:59:06 – Yeah.
0:59:09 – And so the most important thing
0:59:10 is just owning it with confidence.
0:59:12 So here’s an example.
0:59:15 I’m really uncomfortable asking for a raise.
0:59:20 This is really hard for me, right?
0:59:22 That’s not owning it.
0:59:24 How about, hey, I’m so uncomfortable
0:59:25 having this conversation with you right now.
0:59:27 Like, I know I need to ask for a raise,
0:59:28 but I don’t want to ask for a raise
0:59:29 because it makes me really uncomfortable.
0:59:31 But can we have the conversation anyway, please?
0:59:32 Right?
0:59:32 – Yeah.
0:59:33 – Or when you’re out with somebody,
0:59:34 meeting somebody for the first time,
0:59:35 it’s like, I’m really socially awkward
0:59:36 and I’m going to introvert
0:59:37 and I’m probably going to say something
0:59:38 that’s going to make you uncomfortable.
0:59:40 Like that’s just got creeper vibes all the way.
0:59:41 – Yes.
0:59:42 – Right?
0:59:42 – Yeah, that’s like, I’ll follow you
0:59:43 out of the bar situation.
0:59:45 – Yeah, that’s so uncomfortable to even hear,
0:59:46 even though it’s well-intentioned
0:59:49 and it’s explanation versus just so you know,
0:59:51 I’m probably like totally socially awkward.
0:59:52 I’m probably going to say something
0:59:53 that’s going to make you uncomfortable,
0:59:54 make me uncomfortable.
0:59:55 It’s going to happen
0:59:56 because I’m just socially awkward that way.
0:59:58 You can hear the difference in tone.
0:59:59 – Right.
1:00:00 – When you just own it.
1:00:01 – Yes.
1:00:03 – When you’re just confident about who you are.
1:00:04 – Yes, it’s a great point.
1:00:06 – And so all the things that we talk about,
1:00:07 we’re trying to fix the symptoms,
1:00:10 but the cause is that you’re just not owning who you are.
1:00:11 – Right.
1:00:12 – And you can own your strengths
1:00:14 and you can own your awkwardness.
1:00:14 – Yeah.
1:00:15 – Just as an aside,
1:00:17 I don’t believe in strengths and weaknesses.
1:00:19 I believe we have characteristics and attributes.
1:00:20 And in the right contexts,
1:00:22 those things are strengths.
1:00:23 And in the wrong contexts,
1:00:25 those things are weaknesses.
1:00:27 So nothing that we have in our personalities
1:00:29 is inherently a strength or a weakness.
1:00:31 It’s all contextual, right?
1:00:34 So I work hard to be aware
1:00:36 of my characteristics and attributes.
1:00:39 And I work hard to learn
1:00:40 when those things are to my advantage
1:00:42 and when those things are to my disadvantage.
1:00:44 And I work hard to put myself in situations
1:00:46 where who I am is more likely to be an advantage
1:00:48 than a disadvantage, right?
1:00:51 So for example, I’m disorganized,
1:00:53 chronically disorganized, right?
1:00:56 And I remember I was a young entrepreneur
1:01:00 at a networking event, socially awkward, introvert,
1:01:01 not very good at this stuff.
1:01:03 And I met a guy who,
1:01:06 he’s like, Simon, what you have to say is amazing.
1:01:07 I wanna work with you.
1:01:09 Here’s my card, right?
1:01:10 Amazing.
1:01:11 And if I was organized,
1:01:14 I would be texting him from the taxi on the way home
1:01:16 or at least emailing him the next day.
1:01:17 – Pleasure to meet you.
1:01:18 – All of that stuff.
1:01:19 I lost the business card.
1:01:20 – Yeah.
1:01:21 – I don’t know what I did with it, right?
1:01:23 I had it and I lost it.
1:01:26 Two weeks later, I found it at the bottom of a briefcase.
1:01:27 And so I emailed him.
1:01:29 I don’t know if you remember when we met a couple of weeks ago,
1:01:30 I just wanted to reach back out.
1:01:32 And he wanted to work with me more
1:01:33 ’cause he thought I was busy.
1:01:34 – That’s amazing.
1:01:36 – So is being disorganized a strength or weakness?
1:01:38 The answer is it depends, right?
1:01:41 In some contexts, it is really not helpful.
1:01:44 In some contexts, it’s an accidental strength,
1:01:46 introverted and a little bit quiet, right?
1:01:48 And intimidated by, like, you don’t know what to say
1:01:50 in a room, strength or weakness.
1:01:53 Well, at a networking event, it’s not gonna help you, right?
1:01:54 When you have to go around the room
1:01:55 and do all that kind of stuff.
1:01:57 But if you’re in a meeting and you’re the quiet one,
1:01:59 nobody knows if you’re an idiot or a genius.
1:02:02 And you’re the listener.
1:02:03 And they’re just waiting.
1:02:05 So huge strength.
1:02:08 And so all of the things that I know about me
1:02:12 and when I thrive and when I fail,
1:02:14 when I’m happy and when I’m struggling,
1:02:18 I figure out what the characteristics and attributes are
1:02:20 and work very hard to put myself in situations,
1:02:23 find jobs, find clients, find opportunities
1:02:25 that are more likely to result in me
1:02:27 having those characteristics and attributes
1:02:29 work to my advantage,
1:02:30 versus simply chasing the money,
1:02:32 chasing the client, chasing the opportunity,
1:02:34 finding myself in a situation
1:02:35 where this is not gonna work to my advantage.
1:02:37 – Yeah.
1:02:38 And do you believe those characteristics
1:02:41 and attributes can be enhanced?
1:02:42 Some people I know,
1:02:43 they just can’t make a decision for the life of them.
1:02:45 They can’t move forward.
1:02:46 Is that something where you look and say,
1:02:47 well, that’s kind of your DNA,
1:02:49 that’s an attribute or a characteristic,
1:02:50 that’s who you are,
1:02:53 or we can actually take who you are
1:02:55 and enhance something to make that a better,
1:02:57 more smoother process for you.
1:02:58 – Yeah, I don’t think that’s necessarily
1:02:59 a characteristic or attribute.
1:03:00 – Okay.
1:03:02 – You know, what’s underlying that is risk tolerance.
1:03:03 Accountability.
1:03:05 – Yeah, so how do we improve risk tolerance?
1:03:06 – So risk tolerance and accountability
1:03:09 come from relationships, believe it or not, right?
1:03:11 So this is why people say,
1:03:12 the lawyers say we can’t do that.
1:03:13 – Right.
1:03:16 – The lawyers don’t make the decision on this.
1:03:17 – Right, right.
1:03:18 – The lawyer said I can’t do it.
1:03:19 That’s not a lawyer’s job.
1:03:21 And any lawyer who says you can’t do this
1:03:22 is actually not doing the job.
1:03:24 Lawyers have one job, advise you on risk.
1:03:25 There’s a lot of risk if you do that.
1:03:28 And you’re the one who’s supposed to assess the risk reward
1:03:30 and decide if the risk is worth it.
1:03:30 – Yeah.
1:03:31 – And if it’s not worth it, then say no,
1:03:33 but if you think it is worth it, then say yes.
1:03:35 – Every time I hear a CEO say that, it’s such bullshit.
1:03:37 – And when anybody says the lawyer said we can’t,
1:03:39 they’re abdicating the responsibility
1:03:40 of making a decision.
1:03:41 – Yeah.
1:03:42 – It’s a weak leader, right?
1:03:44 – Yes, take counsel from your attorneys.
1:03:45 – Right.
1:03:46 – Absolutely.
1:03:48 But ultimately you’ve got to take a risk or not.
1:03:49 – Right.
1:03:50 – It’s your choice.
1:03:51 – Right.
1:03:52 – If you want to have a high or low risk tolerance,
1:03:52 I don’t care.
1:03:54 – But ultimately say, own up to it and say,
1:03:57 I listened to our lawyers and I agree with them.
1:03:58 This is too risky for our business.
1:03:59 – This is too risky.
1:04:00 – So I made the call.
1:04:00 – I made the call.
1:04:01 – Right.
1:04:02 – I made the call.
1:04:05 They spooked me and I just don’t think it’s worth it.
1:04:06 It’s palpable.
1:04:07 And if it goes sideways,
1:04:09 I think we can deal with the fallout.
1:04:12 That’s the conversation of which the lawyers are part of it.
1:04:15 – So being decisive, I think is about relationships.
1:04:19 When we have relationships where somebody says to us,
1:04:22 I believe in your vision, you got this.
1:04:24 The world needs what you’re trying to do.
1:04:28 You will find your courage to make decisions skyrockets.
1:04:29 – Yeah.
1:04:32 – When you don’t seek relationships and support from others,
1:04:35 you will gonna be alone in all your decisions.
1:04:38 And that’s where the fear creeps in.
1:04:39 – Yeah.
1:04:41 – Because you feel like you’re on an island.
1:04:43 You know, and I think the more senior you get
1:04:44 in an organization, whether you’re a young founder
1:04:47 or whether you’re a senior in a large corporate organization,
1:04:50 you know, it’s a very lonely place.
1:04:51 And we all know it.
1:04:52 We all talk about it.
1:04:53 When you’re not in those situations,
1:04:54 you don’t understand it.
1:04:55 – Yeah.
1:04:57 – But when you’re there, it is an incredibly lonely place
1:05:00 because there’s not a lot of people you can confide in.
1:05:04 When you have moments of crippling doubt,
1:05:05 are we doing the right thing here?
1:05:06 – Mm-hmm.
1:05:08 – That last decision I made that I just blow it,
1:05:11 you can’t go to your team and say,
1:05:13 I think I’ve completely screwed this one up.
1:05:14 You have to be vulnerable and open with your team.
1:05:16 But you can’t share that.
1:05:17 But you have to share it with someone.
1:05:18 – Right.
1:05:19 – And to be able to call a friend.
1:05:20 – Yes.
1:05:22 – And be like, dude, I think I completely screwed this up.
1:05:23 – Yeah.
1:05:24 – Yeah.
1:05:25 – It’s relationships.
1:05:27 Human beings need human beings.
1:05:28 – Yeah.
1:05:28 – Done.
1:05:30 And the more human beings that you have in your life
1:05:31 that love you, care about you, trust you,
1:05:34 and you love them, care about them and trust them,
1:05:36 you will find yourself with a courage
1:05:38 and a confidence that few others have.
1:05:39 By the way, people who have that confidence
1:05:40 without relationships.
1:05:41 – Yeah.
1:05:42 – That to me is like psychotic.
1:05:43 – Right.
1:05:44 So if we want to unpack that a little bit and say,
1:05:46 okay, I’m in my late 40s.
1:05:48 Yeah, I just moved to LA six months ago.
1:05:51 Building a new network of trusted friendships,
1:05:54 relationships, it’s harder to do as you get older
1:05:56 and couples establish patterns.
1:06:00 They have kids now, there’s more responsibilities.
1:06:01 What if someone’s listening to be like,
1:06:03 okay, great guys, you’re telling me over and over again,
1:06:04 I need relationships.
1:06:04 I get it.
1:06:06 I don’t have a whole heck of a lot.
1:06:07 – Right.
1:06:07 – What do I do?
1:06:09 – So I’m in the same place as you.
1:06:10 I’m a COVID transplant.
1:06:13 I’m gonna have friends in LA, some good friends in LA,
1:06:15 but expanding my networks proved to be very hard,
1:06:18 partially because LA doesn’t have serendipity.
1:06:20 I come from New York where you bump into people
1:06:21 all over the place at the time.
1:06:23 Here I go from my couch to my car.
1:06:24 – Right.
1:06:26 – To an hour drive or a conference room
1:06:28 and then back, we’re then reversed back away
1:06:30 and you never bump into any, there’s no serendipity.
1:06:31 – Right.
1:06:34 – And so meeting people has to be prescriptive
1:06:35 and it’s very hard.
1:06:37 It’s very hard to meet people here.
1:06:40 And it’s Hollywood so everybody’s a little bit aloof.
1:06:41 You get people’s cell phones,
1:06:42 but you’re not allowed to use them.
1:06:43 It’s a weird place.
1:06:44 – Yes, yeah.
1:06:46 – So one of the things I’m doing,
1:06:47 and it’s imperfect but I’m doing,
1:06:51 which is I’m leaning on my friends from not from here.
1:06:52 – Yeah.
1:06:53 – When I’m calling them up more.
1:06:54 – That’s what I’m doing as well.
1:06:55 – Yeah.
1:06:58 – And I’m finding ways that we can meet up somewhere
1:07:01 or can you come out here or let me come out to you
1:07:03 or why don’t we go away for a weekend together?
1:07:04 – Yes.
1:07:06 – When I’m realizing that a couple of days
1:07:08 of precious time is better than lots of fleeting moments.
1:07:09 – Yeah.
1:07:11 – And I spend a lot of time on the phone
1:07:12 with my friends who aren’t here.
1:07:14 – So funny how the phone’s made a comeback.
1:07:16 – I do more phone calls with friends remote now.
1:07:18 I actually want to hear them than texting.
1:07:19 It just feels more intimate.
1:07:21 – Also I don’t like Zoom.
1:07:23 I don’t think well sitting.
1:07:24 I’m a pacer.
1:07:26 And so on a phone I can pace.
1:07:27 – Yeah.
1:07:28 – I go for a rock.
1:07:29 I put on one of those weighted backpacks
1:07:30 and just go on some of these trails
1:07:32 and just call a friend, check for a half hour.
1:07:33 We now live in a world where, you know,
1:07:36 it’s considered rude to call without texting first.
1:07:38 I mean, really just don’t answer the call then.
1:07:40 – Right, I just call, yeah.
1:07:40 – I just call.
1:07:42 – If they’re that close a friend,
1:07:43 you should just build a call.
1:07:44 – But I do with people I’m not that close with either
1:07:46 because I just think the phone is a beautiful,
1:07:49 magical to hear voice.
1:07:50 – One more question for you.
1:07:52 We started off the conversation
1:07:52 talking about great leaders.
1:07:54 You mentioned Steve Jobs.
1:07:55 One of the people that I’ve been fortunate enough
1:07:58 to have on this show is Elon Musk a while ago.
1:08:00 Really admired him and, you know,
1:08:02 got to watch his career unfold
1:08:04 and him build some great companies.
1:08:07 Seems like he’s found his why.
1:08:12 That said, Twitter/X was a huge head scratcher for me.
1:08:14 Do you think he kind of lost his way?
1:08:17 – So let’s just take one step to the left
1:08:20 and say why is Elon Musk important, right?
1:08:24 There are plenty of very successful entrepreneurs
1:08:29 who, their success, they won the lottery, you know?
1:08:32 Like, right place, right time, right partner,
1:08:33 and some of the ones we admire
1:08:35 weren’t the ones who came up with the idea.
1:08:36 They’re just the ones who are leading the company.
1:08:37 – Sure.
1:08:39 – And then we’ll leave the names of those companies out,
1:08:41 but you and I both know who they are.
1:08:43 And they won’t be able to repeat it.
1:08:46 Even if they’ve made hundreds of millions of dollars,
1:08:48 they won’t be able to repeat it, right?
1:08:53 Elon is important because he’s repeated it multiple times.
1:08:54 He’s the real deal.
1:08:55 – Real deal.
1:08:56 – Real deal, right?
1:08:57 So that’s important.
1:08:58 – Yes.
1:08:59 – He didn’t win a lottery.
1:09:02 Absolutely, people bet against him.
1:09:05 And he had so much passion and vision for what he was doing
1:09:08 that he proved all the naysayers wrong.
1:09:11 He made a very bad decision on Twitter, right?
1:09:12 He got backed into a corner.
1:09:14 He backed himself.
1:09:15 – I don’t think he wanted to buy it at the end.
1:09:16 – I don’t think so.
1:09:17 I think he backed himself into a corner.
1:09:18 – Yeah.
1:09:21 – And he tried to get out of the deal.
1:09:22 Couldn’t.
1:09:24 Just as a side, I think it’s really funny.
1:09:26 The board members of Twitter and like leaders
1:09:27 that were like, we would never sell, how much?
1:09:28 – Okay.
1:09:29 – Yeah, totally.
1:09:31 – How’s that idealism doing for you guys?
1:09:33 Turns out everyone’s got a price.
1:09:35 Anyway, I think Elon backed himself into the corner
1:09:39 because he’s always beaten the naysayers in the past.
1:09:41 People are saying, well, never doubt Elon.
1:09:42 – Right.
1:09:43 – Well, no, you can doubt Elon.
1:09:46 In this case, he doesn’t have a passion or a vision.
1:09:47 – Yes.
1:09:47 – Like he did for the others.
1:09:49 – The others were his ideas.
1:09:49 – Others were his ideas.
1:09:52 I mean, Tesla wasn’t his idea, but he saw the potential.
1:09:53 – Right.
1:09:54 – The decisions he made were clearly
1:09:56 to advanced a greater good.
1:09:58 And he was willing to take tremendous financial risk
1:09:59 to do it.
1:10:01 In this case, he’s trying to make a company
1:10:03 that doesn’t make money, make money,
1:10:05 as opposed to advance some sort of greater good.
1:10:07 And it’s clearly, I mean, he keeps talking
1:10:09 about freedom of speech, but that’s not it.
1:10:10 – Yeah.
1:10:11 – Because you can just look at the decisions
1:10:12 that are being made.
1:10:13 – Yeah.
1:10:13 – I think he screwed the pooch.
1:10:14 I think he made a mistake.
1:10:18 And the sad part is because I think he has a brand
1:10:21 and his brand is look at the shit I get right.
1:10:24 I think he’s too intimidated, shy, embarrassed
1:10:27 to say I blew it, right?
1:10:28 – Yeah.
1:10:30 – And if you would just come at and be like, look,
1:10:32 I made the biggest mistake in my career.
1:10:34 I got wrapped up in the excitement of it all.
1:10:37 I find myself buying something I didn’t wanna buy.
1:10:39 We’ve all done it, but when you’re the world’s richest man,
1:10:41 it’s just a lot more expensive.
1:10:44 And at the end of the day, I don’t really wanna do this.
1:10:45 It’s not my passion.
1:10:47 And I’m willing to sell Twitter to somebody
1:10:49 who actually has a vision for this thing.
1:10:51 You know, I don’t wanna lose my shirt on it,
1:10:52 but you’ll get a good deal.
1:10:53 – Yeah.
1:10:54 – And I need to unload this thing.
1:10:55 And I screwed the pooch.
1:10:57 I don’t wanna go back and focus my time energy
1:10:58 on the things that I actually love and care about.
1:10:59 – Oh man.
1:11:01 – If he just said that, we’d all be fine with it.
1:11:02 – Yeah.
1:11:03 – We’d all be like, cool.
1:11:05 – Everyone would stand up and applaud.
1:11:06 – Everyone would stand up and applaud.
1:11:07 – And what he’s doing, it’s unfortunately,
1:11:11 it’s very the times, which is deny, deny, deny,
1:11:12 deny, deny, right?
1:11:14 Like nobody does anything wrong anymore.
1:11:16 If you look at all of his companies,
1:11:18 you can see there’s an idealism
1:11:21 and that you can see they kind of like fit a portfolio.
1:11:24 Like they kind of all belong in this fund.
1:11:24 This one doesn’t.
1:11:25 – It doesn’t.
1:11:28 – Also, it’s a social product that I find
1:11:29 that it’s a different beast.
1:11:30 – Yeah.
1:11:31 – It’s not science.
1:11:33 – Guy with ass burger shouldn’t be running a social.
1:11:33 – Exactly.
1:11:35 – Look, it’s so fraught with irony.
1:11:37 One of his things that he said at the beginning was,
1:11:39 I think it’s irresponsible and bad
1:11:42 that one company should be deciding
1:11:45 what we say or don’t say.
1:11:47 So I’ve replaced that company with a person.
1:11:49 It’s another one person decides
1:11:51 who all we should be saying or not saying.
1:11:51 – Yeah, I know.
1:11:52 – I mean, whatever.
1:11:53 We can talk about it.
1:11:56 Like he screwed up and I can’t imagine the pressure
1:11:58 he feels or more importantly that he puts on himself.
1:11:59 It’s gotta be so tough.
1:12:00 – You know, he’s still a human being.
1:12:01 – A hundred percent.
1:12:02 – Give the guy a little grace.
1:12:03 He screwed up.
1:12:03 We all do.
1:12:05 His was more expensive and more public
1:12:06 than the rest of ours.
1:12:07 – I’d much rather be working
1:12:10 on neuroscience related issues and working on this.
1:12:11 – Yeah, the exactly.
1:12:14 – Like every moment or day that he spends working on this,
1:12:17 he’s not helping us find solutions to energy problems.
1:12:18 – Right.
1:12:19 – He’s not helping us find solutions
1:12:21 to mental health problems.
1:12:22 – Which he’s damn good at.
1:12:24 – I want Elon to do the stuff that he’s great at
1:12:25 and I don’t want him to do Twitter.
1:12:26 – Yeah, same.
1:12:28 We’re completely aligned.
1:12:29 So what’s next for you?
1:12:32 You’ve got several successful best selling books.
1:12:35 That could just be your jam for the rest of your life.
1:12:39 – I’ve all but stopped doing in person public speaking.
1:12:41 I do them occasionally,
1:12:45 but it’s basically not happening anymore.
1:12:45 – Yeah.
1:12:48 – Because it doesn’t work like it used to.
1:12:50 I believe in impact.
1:12:52 Impact is more important to me than money.
1:12:54 And when I was starting, I was proselytizing.
1:12:58 I was preaching a point of view in a way the world worked.
1:12:59 And most people in the room had never heard of me
1:13:01 or my ideas.
1:13:04 And so I came into preach and the delta
1:13:05 of how people felt when I came in,
1:13:07 when people felt when I came out
1:13:08 and the lifestyle that I was living,
1:13:11 which was on the road all the time exhausting.
1:13:12 – Yeah.
1:13:13 – The pain was worth it.
1:13:15 And I’m a great, but people like,
1:13:16 you should never quit.
1:13:16 You have to have grit.
1:13:18 People like, well, you have to know when to quit.
1:13:19 My standard is very simple,
1:13:23 which is if the struggle or the sacrifice is worth it,
1:13:24 then keep doing it.
1:13:26 If the struggle or sacrifice doesn’t feel worth it,
1:13:28 then stop doing it, right?
1:13:30 You know you have cause
1:13:31 and you know that you’re doing the right thing.
1:13:34 When this sucks, but it’s worth it.
1:13:35 – Yeah.
1:13:36 – Right?
1:13:37 And so I hated it, but it was worth it.
1:13:39 I hated the lifestyle.
1:13:42 Now the delta is much smaller.
1:13:44 I’m coming to talk about ideas
1:13:46 that people have already read about or heard about,
1:13:49 or I’m no longer proselytizing a group of people
1:13:50 who’ve never heard of my work.
1:13:53 And so I’m in this magical period of exploration.
1:13:55 I actually don’t know what I’m gonna do next.
1:13:56 And so I’m saying yes to things
1:13:58 that have no financial gain whatsoever,
1:14:00 but I’m just kind of like giving it a try
1:14:01 to see if I like it or not.
1:14:03 I know that it won’t be what I’ve been doing.
1:14:04 – Yeah.
1:14:05 – I like steep learning curves.
1:14:06 This is the curse of 10,000 hours.
1:14:08 Gladwell made this whole 10,000 hour things
1:14:09 that you have to achieve 10,000 hours
1:14:11 or something before you can achieve mastery.
1:14:15 And we all are in quote unquote pursuit of the 10,000 hours.
1:14:16 But what we forget, and I firmly believe
1:14:18 that everything is balanced.
1:14:19 Everything in the world is balanced.
1:14:20 Every advantage you have in the world,
1:14:22 there’s a disadvantage that comes
1:14:24 with whatever that thing is, always.
1:14:27 The world is always balanced and nature pours a vacuum.
1:14:29 And so there’s a downside to the 10,000 hours.
1:14:30 You talk to lots of people who have mastery.
1:14:32 You’ll find the same pattern.
1:14:34 There’s only one of a few things.
1:14:35 Boredom is one of them.
1:14:38 It was so exciting when the steep learning curve was steep.
1:14:40 And I’ve met directors and producers
1:14:42 and VCs and entrepreneurs.
1:14:44 And they’re so good at what they do.
1:14:46 They’re considered the best in their industry.
1:14:47 And they’re out there.
1:14:48 They know how to make money.
1:14:49 They know how to make movies.
1:14:50 They know how to write books.
1:14:51 They’re like bang, bang, bang.
1:14:54 And if you get them on a quiet night,
1:14:55 when they’re a little bit tired,
1:14:58 probably a glass of whiskey or two in them,
1:15:00 they will absolutely all admit
1:15:01 that they’re bored out of their skulls.
1:15:03 Because there’s nothing exciting
1:15:04 about what they’re doing anymore.
1:15:05 It’s just rote.
1:15:07 – Because it’s become second nature to them?
1:15:08 – Because it’s 10,000 hours.
1:15:09 They have so much mastery.
1:15:10 It’s not exciting.
1:15:12 It’s the excitement of gaining 10,000 hours.
1:15:14 It’s actually more enjoyable for the human being.
1:15:16 I meet these really, really senior successful people
1:15:18 that privately admit that they’re bored.
1:15:20 – I wonder how Steph Curry does it.
1:15:22 – I wonder how those professional basketball players
1:15:24 when they’re just like the top of their game,
1:15:25 how they stay motivated.
1:15:26 Like Kobe was really good at this.
1:15:28 – If you saw “The Last Dance,”
1:15:30 Michael Jordan created narratives that were fake.
1:15:31 – Yeah, that’s right.
1:15:32 He was making shit up.
1:15:33 – He was making shit up.
1:15:35 He was making enemies.
1:15:36 – Yeah.
1:15:38 – He was not this great infinite minded guy
1:15:38 that we all thought he was.
1:15:40 He was the consummate finite player.
1:15:41 He was the best finite player in the world
1:15:43 where he would produce conflict that didn’t exist
1:15:44 to make himself so angry
1:15:46 that he was gonna take you down.
1:15:48 I mean, that was crazy.
1:15:50 That was insane. – It was crazy insight.
1:15:52 And I do think they get bored as well.
1:15:54 And I think it’s just like the next ring
1:15:55 and become the winning most of this
1:15:56 or the winning most team.
1:15:59 They just keep setting finite goals.
1:16:00 And that’s exciting for the short term,
1:16:02 but do they have long-term joy?
1:16:03 I don’t know, you know?
1:16:06 So boredom is one thing that I think a lot of people,
1:16:07 when you reach 10,000 hours,
1:16:10 I think the other thing is you find yourself,
1:16:12 like when you’re a hammer, every problem’s a nail.
1:16:14 And when you have mastery of something,
1:16:17 you see the whole world through that one lens.
1:16:20 And I think it creates a closeness to new.
1:16:21 And you see this a lot.
1:16:25 You see very successful CEOs, entrepreneurs
1:16:29 that miss significant changes in technology, for example.
1:16:31 And the number of CEOs who didn’t see the internet
1:16:33 as a thing. – Right.
1:16:34 – Yeah, you look back and look at those old quotes
1:16:36 and they’re hilarious.
1:16:39 – Or like bomber who like, shittle over the iPhone.
1:16:40 Like it’ll never be a thing
1:16:41 because no one’s gonna spend that amount of money
1:16:42 on a phone.
1:16:43 – You’re smarter than that.
1:16:45 But the problem is it’s not because he’s dumb.
1:16:46 – Yeah.
1:16:48 – And it’s not because he’s blind.
1:16:49 And it’s not because he’s stupid.
1:16:52 It’s because when you have mastered something
1:16:54 and you’ve been doing that thing the same way
1:16:57 for 30 years to the point where it’s made you rich
1:16:59 and famous and the top of the organization,
1:17:01 it is very, very hard to see the world
1:17:04 through any other lens than that lens.
1:17:05 – And whether you know it or not,
1:17:07 you’ve created a walled garden for yourself.
1:17:09 When I was at Google, the first thing I did
1:17:11 when I landed inside and I was assigned
1:17:13 to their social products team and I was running mobile
1:17:16 for Google+ which ended up failing.
1:17:17 – Well done.
1:17:18 – Listen, I bounced.
1:17:21 I was speaking of leaving jobs quickly.
1:17:22 I was there for like four months
1:17:25 and I went to Google Ventures and just became an investor.
1:17:27 I knew there was no future there.
1:17:28 But yeah, that was horrible.
1:17:30 But one of the things I realized is like,
1:17:31 I’d gone to these product meetings
1:17:33 and there was like 30 people in the room.
1:17:36 And I’d start talking about what we were doing
1:17:37 that was novel and different
1:17:40 and that just wasn’t feature parody with Facebook.
1:17:45 And it was like, they were so of the mindset
1:17:47 of like, we’re Google, we can do anything.
1:17:49 We have scale.
1:17:51 They didn’t even use anyone else’s tools.
1:17:53 They were never installing other apps
1:17:53 of other competitors.
1:17:54 They weren’t playing.
1:17:55 They lost all of that.
1:17:57 They had their free lunches.
1:17:58 They had their soccer campuses.
1:18:01 They even had a half pipe on Google’s campus,
1:18:03 which I rode, which was actually pretty awesome.
1:18:08 But it was like, you’re so surrounded by like-minded people.
1:18:11 You don’t think to play and there’s no discovery.
1:18:13 And so I think that’s what happened with Bomber and others
1:18:15 when you don’t get a chance to actually get out there
1:18:16 and be a real person.
1:18:17 – And that’s the thing that made you successful
1:18:19 in the first place was the open-mindedness
1:18:20 of the child like one. – Play, yeah.
1:18:21 – You’re 100% right.
1:18:23 And this is the curse of the 10,000 hours.
1:18:26 It’s 10,000 hours plus, plus, plus,
1:18:29 which is why publishing didn’t invent the e-reader.
1:18:32 Amazon invented the e-reader, not publishers.
1:18:34 – Right, very confusing.
1:18:37 – Why is it that Netflix made streaming a thing
1:18:39 and not the movie and TV industry?
1:18:41 How did you guys miss that?
1:18:43 You could have, but you didn’t.
1:18:44 – You can’t blame companies or industries
1:18:46 ’cause companies and industries don’t make decisions.
1:18:50 It’s human beings who have achieved mastery,
1:18:51 who are now running organizations,
1:18:53 who are decision-making positions,
1:18:56 who literally cannot perceive the world
1:18:58 outside of the 10,000 hours of mastery that they’ve achieved.
1:18:59 – For sure.
1:19:03 I’m at that point where I have 10,000 hours of mastery
1:19:06 in one little space and it scares the shit out of me.
1:19:08 And so if there’s one thing I know,
1:19:10 which is to go be an idiot again.
1:19:11 – I love that.
1:19:13 – I need to start with four hours.
1:19:15 Okay, I’m gonna learn about venture.
1:19:18 I don’t know and understand anything about money.
1:19:20 I’ve never been motivated, I’m the money idiot.
1:19:21 And I’m sitting at these meetings
1:19:23 and they’re all using all this jargon.
1:19:25 And I am so clueless.
1:19:28 It is not fun, it is not comfortable, I feel dumb.
1:19:29 Everybody thinks I’m smart
1:19:30 because I’ve achieved something
1:19:33 and they think I know everything about everything, right?
1:19:35 And I’m trying to be dumb.
1:19:37 And I’m trying to find what I’m passionate about
1:19:40 that is worth really working hard
1:19:43 to not be dumb at the thing that I’m dumb about.
1:19:44 – What’s your point earlier?
1:19:45 I mean, it’s about asking questions
1:19:46 that you don’t know the answer to again.
1:19:47 – You’ll appreciate this.
1:19:50 So I got to know James Kars,
1:19:52 who was the originator of the concept
1:19:55 of finite and infinite games before he died.
1:20:00 And when I first met him, of course, the burning question,
1:20:01 how’d you come up with that?
1:20:03 Right now, just as an aside for those
1:20:04 who don’t know what I’m talking about.
1:20:07 So Jim Kars was a philosopher and theologian.
1:20:09 He worked at NYU who wrote a book
1:20:12 in the mid-1980s called “Finite and Infinite Games”
1:20:13 where he defined these two types of games.
1:20:15 It’s a kooky little philosophy book, right?
1:20:16 He defined these two types of games.
1:20:19 A finite game is defined as known players,
1:20:22 fixed rules, agreed upon objectives, football, baseball.
1:20:23 If there’s a winner necessarily,
1:20:25 you have to have a loser or losers.
1:20:28 But more important, there’s always a beginning,
1:20:29 a middle, and an end.
1:20:30 Then you have infinite games.
1:20:33 Infinite games are defined as known and unknown players,
1:20:34 which means you don’t necessarily know
1:20:36 who all the other players are,
1:20:38 and new players can join the game at any time.
1:20:39 The rules are changeable,
1:20:42 which means every player can play however they want.
1:20:43 And there’s no such thing as winning.
1:20:45 You can only perpetuate the game.
1:20:47 The goal is to stay in the games long as possible.
1:20:48 – Right, so life, basically.
1:20:51 – Business, nobody wins business.
1:20:52 When Circuit City went bankrupt,
1:20:54 Best Buy didn’t win anything.
1:20:55 The game will change forms.
1:20:57 You don’t know who your competitors are necessarily.
1:20:58 New competitors can join.
1:21:00 Every company can run however they want to run.
1:21:02 And no one’s ever declared the winner of business.
1:21:04 This is what Kars put out in the world.
1:21:07 And it dramatically impacted my work.
1:21:09 ‘Cause I bought into his philosophy,
1:21:11 Hogan and Sinker, and I started to realize,
1:21:12 if you listen to leaders,
1:21:13 they talk about being number one,
1:21:15 being the best, or beating their competition.
1:21:17 Based on what?
1:21:18 Based on what agreed upon metrics,
1:21:19 objectives, and time frames.
1:21:21 So when you play to win in a game
1:21:22 that has no finish line,
1:21:24 turns out you make a lot of stupid decisions,
1:21:26 and you end up destroying trust, cooperation,
1:21:27 and innovation.
1:21:30 And if you look, most companies today,
1:21:32 most large companies are not innovative.
1:21:34 They just buy smaller and more innovative companies.
1:21:37 The average lifespan of a company, I think, is 17 years,
1:21:39 which is abysmal, right?
1:21:41 Look at the damage that companies are doing
1:21:42 because they’re so short-termist.
1:21:44 It’s all because they have a finite mindset
1:21:45 in the infinite game of business.
1:21:47 What Kars articulated was a truth.
1:21:49 A lot of people have theories.
1:21:50 Finding them games is a truth.
1:21:52 That is how the world works,
1:21:54 and you have to play for the game you’re in.
1:21:56 So I got to know some.
1:21:57 And of course, when I met him the first time,
1:21:58 I sat down with him and was like,
1:22:02 I gotta ask, how did you come up with this?
1:22:05 And he was telling me that in the 1970s,
1:22:06 there were all of these salons,
1:22:09 so these intellectual salons of which he was a part of,
1:22:11 where they would bring in people from different disciplines,
1:22:13 like mathematics and philosophy and engineering,
1:22:17 to debate the topic of the day, which was game theory.
1:22:20 Game theory was all the rage in the 1970s,
1:22:23 and lots of theories were coming out of these salons.
1:22:24 So for example, the prisoner’s dilemma,
1:22:26 which many of us are familiar with,
1:22:29 that came out of one of these salons in the 1970s.
1:22:31 So he was in these salons,
1:22:35 and it occurred to him that in all of these discussions,
1:22:37 they were always talking about winning and losing,
1:22:38 all of them.
1:22:40 Nobody was talking about playing.
1:22:43 Even the prisoner’s dilemma is about winning and losing.
1:22:45 And then he sort of went home with this problem
1:22:46 he had stuck in his mind,
1:22:48 and he watched his kids,
1:22:50 and he saw when his kids played ping-pong,
1:22:52 there was always screaming and yelling,
1:22:53 there was always fighting,
1:22:55 and there was always accusations of somebody cheating.
1:22:56 Every time.
1:22:57 – That doesn’t change with adults, by the way, right?
1:22:58 – But yeah.
1:23:00 – But when his kids were playing Lego,
1:23:03 they would sit there quietly for hours,
1:23:05 and one of the kids would leave for a little bit,
1:23:06 and then come back later,
1:23:09 and the game would, the Legos would last for days,
1:23:11 and they would start and stop and start and stop,
1:23:12 and there was never any fighting,
1:23:14 and there was only cooperation.
1:23:17 – And he realized that we’re so obsessed
1:23:18 with winning and losing,
1:23:19 that we’ve forgotten the value of playing,
1:23:24 and not all games have an end.
1:23:26 And business should be treated like a game
1:23:27 rather than a competition.
1:23:31 It should be treated like Lego more than baseball.
1:23:32 – Yes.
1:23:34 – And we overuse sports and war analogies
1:23:35 in business all the time.
1:23:36 – Yeah, hit a home run.
1:23:38 – ‘Cause we treat it like a game.
1:23:40 We have launches, we have campaigns,
1:23:42 we have wins, we have losses,
1:23:44 we give bonuses for accomplishment,
1:23:45 we talk about performance-driven,
1:23:47 but we never talk about creativity,
1:23:49 we never talk about joy,
1:23:53 we never talk about cooperation or cross-pollination,
1:23:55 and this is the magic of great innovation
1:23:57 and great businesses.
1:24:00 And so you talk about the magic of play, right?
1:24:03 One of the problems with 10,000 hours of mastery,
1:24:04 or any kind of mastery,
1:24:06 is you’ve become so good at something,
1:24:08 now you wanna win every time you’re playing,
1:24:10 because you’re the expert.
1:24:13 And there’s a joy in not worrying
1:24:15 about the outcome.
1:24:18 There’s a joy in just playing.
1:24:23 And so I am looking for few opportunities to play baseball,
1:24:25 and more opportunities to do Lego.
1:24:26 – That’s interesting.
1:24:28 – A few years ago, I picked up studying Zen
1:24:30 with a great Zen master out of Santa Fe,
1:24:32 and one of the things about Zen
1:24:34 is it is a dedicated practice.
1:24:37 You wanna get in your reps in terms of hours,
1:24:39 but you cannot have an outcome,
1:24:41 because that pushes away.
1:24:43 It defeats the point.
1:24:46 The West is more obsessed with finite,
1:24:47 and I think Eastern philosophies
1:24:48 are more obsessed with infinite.
1:24:51 I learned that you are actually not present
1:24:53 until somebody else says you are, right?
1:24:55 Because you can’t be present by yourself.
1:24:57 I mean, you can, that’s one of the side effects,
1:24:59 but the true value of being present
1:25:01 is as a gift to another, right?
1:25:02 So let’s think about meditation.
1:25:04 For those who’ve ever practiced meditation,
1:25:06 what you’re supposed to do is sit still,
1:25:08 and focus on one thing,
1:25:09 whether it’s something you stare at,
1:25:12 whether it’s a mantra or a sound,
1:25:14 or the ocean, or whatever it is,
1:25:17 you’re supposed to focus on one thing.
1:25:18 You can’t clear your mind, it doesn’t exist.
1:25:19 You focus on one thing,
1:25:20 and you learn to clear your mind
1:25:22 of all other thoughts except this one thing.
1:25:25 And if you have a thought about work,
1:25:26 you label it a thought, you say,
1:25:28 “Ah, that’s a thought, I’m gonna push that aside
1:25:29 “and I’ll deal with that later.”
1:25:31 And you find this tremendous calm and focus
1:25:33 and tremendous relaxation.
1:25:34 Okay, what was the point of all of that?
1:25:35 Just so you can feel good?
1:25:38 No, that’s the unintended byproduct
1:25:40 that you feel good and you have all the health benefits.
1:25:43 The true benefit for me of practicing meditation
1:25:45 is that when I’m sitting with a friend,
1:25:46 they wanna tell me something amazing
1:25:47 that’s happening in their life,
1:25:48 or they wanna tell me something
1:25:49 that’s horrible that they’re dealing with.
1:25:51 I’m focused on one thing and one thing only,
1:25:53 what they’re telling me.
1:25:55 Every other thought, the car that just screeched,
1:25:56 don’t hear it anymore.
1:25:58 I have thoughts of things I wanna say,
1:25:59 and I label them thoughts, I’m gonna say,
1:26:01 “That’s a label of, I’m gonna deal with that later.”
1:26:02 You’re bringing it into real life.
1:26:03 I’m bringing it to real life.
1:26:04 And at the end of the conversation,
1:26:06 I know that I have been present,
1:26:08 all of that practice, we call meditation a practice,
1:26:10 that all of that practice was worth it.
1:26:12 For this one moment when my friend says to me,
1:26:13 “Thank you for listening,”
1:26:14 or “Thank you for being present,”
1:26:17 or “I really feel heard, thank you.”
1:26:19 Now all of that meditation was worth it.
1:26:22 And all of the benefits that I derive are secondary.
1:26:24 The true benefit is the gift that I get to give
1:26:27 from working really hard in my own practice.
1:26:31 So we’ve made so many of these Eastern practices
1:26:34 that are pro-social, selfish.
1:26:35 We made them checkboxes.
1:26:36 We’ve made them checkboxes,
1:26:37 and we’ve made them only for us.
1:26:38 Yes.
1:26:42 And perpetuating that imbalance that America is so good at,
1:26:44 which is we’ve over-indexed on rugged individualism,
1:26:47 maubrum in, with hero-ized CEOs,
1:26:50 as if they did everything by themselves, right?
1:26:51 We’re all striving to be the hero.
1:26:52 We’re all striving to be influencers.
1:26:54 We’ve created heroes out of individuals
1:26:57 of which none of us succeed without groups of people
1:26:59 who believed in us, took bets on us,
1:27:01 were there for us, they were crying their shoulders,
1:27:04 or just cheered us on on a rainy day.
1:27:07 And we’ve forgotten that the more we can focus
1:27:09 on each other and taking care of each other,
1:27:11 and what it means to be a good friend,
1:27:12 to be a good partner, to be a good leader,
1:27:15 to be a good follower, to be a good employee,
1:27:17 to be a good boss, to be a good, all the relationship,
1:27:21 friend, that’s where true joy and success lies.
1:27:26 And play, play, I think is the most magical of all,
1:27:30 play without a required income.
1:27:33 You start drawing, you start playing with Lego,
1:27:36 and a few days later, you decide to put it away.
1:27:39 Yeah, arbitrary, yeah.
1:27:40 And I’m trying to do that with my career.
1:27:41 I’m trying to play again.
1:27:43 That’s great, I love to hear that.
1:27:44 Must feel good.
1:27:46 Well, it’s nerve-wracking.
1:27:47 You know, we talked about being uncomfortable,
1:27:49 I’m uncomfortable, I have no idea
1:27:52 what my future is gonna be, but I’m okay with that.
1:27:53 That’s awesome.
1:27:55 What you did with me, it was beautiful.
1:27:56 Thank you again for that.
1:28:00 That was just a fun little few minutes of unpacking that.
1:28:02 Well, let’s just say, I wanted to go deeper on that.
1:28:03 Where do I go on your website?
1:28:05 Is there a specific course?
1:28:07 There’s a whole thing about finding your why.
1:28:09 Okay, so that’s the one to sign up for.
1:28:09 That’s the one to sign up for.
1:28:11 Okay, awesome.
1:28:12 Simon, thank you so much.
1:28:13 This is great.
1:28:13 Oh, my pleasure, thanks for having me.
1:28:14 It’s been great.
1:28:15 Yeah, the joy, thanks.