SPEAKERS

Ashton Kutcher Actor & Investor

Ashton Kutcher is an actor, investor, entrepreneur, producer and philanthropist.

Kutcher has been investing in technology for over a decade, both as an angel investor and a founding partner of A-Grade Investments and Sound Ventures. His fund portfolio includes Airbnb, Uber, Flexport, Brex, Robinhood, Bird, Airtable and Affirm among others.

Kutcher has been named one of TIME magazine’s “100 Most Influential People in the World,” as well as being honored by Vanity Fair ‘s “New Establishment List,” which identifies the top 50 of an innovative new breed of buccaneering visionaries, engineering prodigies and entrepreneurs. Twice, Kutcher was named one of Forbes magazine’s “World’s Most Powerful Celebrities,” as well as one of Fast Company magazine’s “Most Creative People.”

Kutcher is also the co-founder of Thorn: Digital Defenders of Children (www.thorn.org). Thorn drives technology innovation to fight the sexual exploitation of children.

"Pain is inevitable, but suffering is a choice. When these things come that are painful or unpleasant... I know that if I don't execute against them, they'll turn into suffering. And I choose to not have suffering."

<cite>- Ashton Kutcher </cite>

Ryan Petersen, Founder and CEO @ Flexport

Ryan Petersen is founder and Chief Executive Officer of Flexport, a full-service freight forwarder and customs broker. Since founding Flexport in 2013, Ryan and his team have worked to make global trade easy for everyone. Ryan led Flexport from inception to the company it is today: supporting over 10,000 customers and suppliers across 109 countries and doubling revenue to nearly $450m last year. His areas of focus include setting company strategy, ensuring the company tracks to goals, and most importantly, building and maintaining Flexport’s unique culture.

Prior to founding Flexport, Ryan helped run an e-commerce company and co-founded ImportGenius, one of the largest providers of business intelligence to the import-export industry. His experience and frustration with global logistics served as the inspiration to start Flexport. Ryan holds a Bachelor’s Degree in Economics from the University of California, Berkeley and an MBA from Columbia University.

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Show Notes

• How Ashton & Ryan first met & their early entrepreneurship hustles (2:15)
• Productivity tools & systems (4:06)
• How to say “NO” to optimize your time (7:08)
• Leverage culture in your organization to scale your time and mind (10:32)
• The power of predictability on company culture and productivity (15:26)
• Networking Hack: Connect through social impact (17:40)
• Creating a personal mission statement & the “energy audit” (19:02)
• How to avoid being reactive to your to-do list (21:26)
• Productivity as your company scales & cultivating sub-cultures within your org (23:17)
• What question should you be asking yourself right now? (25:01)

Transcript

How Ashton and Ryan first met & their early entrepreneurship hustles

Patrick: Thank you both so much for joining us.

Ryan: Thank you, thanks to you for that nice intro. And Ashton, awesome to see you! Many of you probably have no idea, but Ashton is one of my first investors in Flexport, so great... so great to hang out and reconnect.

Can I tell that story about the first time when we met? One of Ashton's first questions he ever asked me was what was your middle school hustle? I guess he likes to test, like, if entrepreneurs actually like are true entrepreneurs from back when they were in middle school. And I told them how I used to sell lollipops to the other kids.

and as always, I was a discounter, so my mom would buy these boxes at Costco when you could get the lollipops for 6 cents, and the other kids were selling them for 25. And I came in and did two for 25 and undersold everybody.

But you told me that your hustle was like, you had like a, more like a subscription service for your locker, which was full, which you kept stocked full of candy. So as Saas pioneer here. I just love that.

Ashton: There were, there was those little Debbie oatmeal cream pies, and I had a stash of them in my locker and I would, I would sell people and they could get the code to my locker, which I would change on a monthly basis. They could just go in and take them.

And that was my move!

But I, I love asking the question because I kind of think there's a certain version of... there's a certain mentality that, that comes from that high school hustle question.

That is one... were you just satisfied with your station in life? And most people that become great innovators are people that are never satisfied with 'what is' and want more.

And two, are you scrappy enough to figure how to make it work when it's not working? And I think that like, those functions make great entrepreneurs and if you learn it and it just becomes a part of your blood, it becomes something you never have to question as an investor going forward.

So... but that's, that's the emphasis of the question.

Productivity tools & systems

Ashton: But we are here to talk about productivity and scaling your time and mind.

Which when posed with this session and this idea... it seems like it's an ever-changing thing. The tools that you use. And people who are highly productive are always looking for the next tool. I don't think I ever stop looking for the next tool to become more effective.

And Ryan, you have between your company, Flexport.org, your VC investing all the various things you do... you've gotten very good at it.

And so maybe you could share some of the baseline tools and tips that you think or see as pat in your own personal behavior and actions?

Ryan: Yeah, love to. So from a tools perspective, I totally agree with you. I'm always looking for something new. I've been using the same to-do list app for a few years called Things. It's fine. I'm sure there's other ones that are maybe even better, but I like it.

What I'm more focused on is systems. Like, what is the process that I use. And that I've used the same process for 20 years and it's... I didn't invent it... it's from that book, Getting Things Done. Many of you probably read it.

And it's all about breaking things into super bite-size... having some goals, like start with your values, actually. What do you want to do in life? Pick some goals. And then how do you break those into the smallest possible chunk that you could get done today? If possible.

And if, and if the list is, if the thing is sitting on your to-do list for so long, and it's just sitting there, which we all know that feeling, you're just like, wait, I keep staring at this thing. It's probably because it's too big. So break it down into something that you can do in the next 45 minutes. So I use that system.

Oh, one nice thing about it. Like by no means, am I like awesome at this. Like I drift and become unproductive for periods of time, et cetera. But one nice thing about having a good tool like Things or Evernote or whatever you guys like to use is it's there when you come back.

Like your goals are already still listed, kind of the objectives are there. So when you fall off the wagon, it's really easy to get right by like, "oh, cool! I already like documented what I want to do."

So I'm not... I'm definitely not perfect at this stuff. But that system has worked really well for me. Inbox zero, et cetera.

Ashton: Yeah, I'm... I try to get to inbox zero. It never seems to happen... and there's probably a distinct reason why it doesn't happen... I think my biggest productivity hack is heard somewhere, which is that "Your email inbox is everyone else's to-do list and treating it as such."

And so before I jump into my inbox in the morning, I draft and put out all the outbound emails that I have. And tick off the action items that I have for the day.

that those things are in momentum before I start getting to everybody else's stuff.

I would say the other thing that I do quite often. Is I actually create notes tabs for people. So specifically, go in at the end of the day and go, "I need to talk to this person about that. I needed to talk to that person about this. I need to talk to this person..."

So I actually tag the action item to an individual, as opposed to just put it. ... leave it in this sort of ether of action items. Because generally speaking, it's an interaction with another human being. Otherwise I would just be doing it right now.

Yeah. Okay.

How to say "NO" to optimize your time

Ashton: The next thing, think... we talked a little bit about this, just having a chat about this call, is... what do you say no to? How do you say no to it? Because one of the things in optimizing time and productivity is saying, no. It's not just like, who's on the bus who you leave off the bus. It's not just what you are doing. It's what you're not doing. And the framework that you create to say no. Which I think is key and core.

Ryan: Your answer is probably more interesting here because you get asked to do more. So you're like famous. I, nobody cares about me. They don't ask me to do that many things.

Within the company, that's really hard to say no. And it's like, you want to do everything? I'm an entrepreneur. I want to say yes. And just do the things.

And so it's gotta be what are my priorities? And like, make sure I check my priorities list every single day. And if it doesn't map really clear to those things, I have to say no.

And I've been bad at that over the years. Like, especially when I was first getting going, and like people started to take an interest in me and like wanted to talk to me about stuff. Like other entrepreneurs want to chat. Maybe VCs want to do a reference check or get my opinion on some startup.

I used to say yes to these things because it's like, it's interesting. It's fascinating. Or someone wants me to help on a project. I'd love to help you. B a great way to learn about the world and create some value. But like you quickly realize my time would fill up. And I was doing BS instead of working on the company. So I had to start saying no to stuff but...

I'd like to hear your answer to this because you get asked to do many more things than you can have a huge impact with just like a tweet or something. Right. It's like, how do you decide what you're going to say yes to, or not?

Ashton: Well, I started several years ago. You know, my company has a mission statement. Every org that I get involved with all the companies I invest in, they have a mission statement.

And years ago I created a personal mission statement for myself. and it was am I doing What am I really affecting? And what do I want the outcomes to be? And then backed into a personal mission statement. And so that sort of created a matrix of what do you say yes and no to. Which makes a lot of no's easy.

The things that it makes hard are things that, you know you can do. You know, it might take you a fraction of the time to accomplish the thing that the person that's coming to you, wants to have accomplished. That it will take them to accomplish it. And you like the person. And you actually know the thing that they're doing will make a positive difference in the world. But by doing it, you jeopardize your ability to accomplish the things that are on your own statements.

And one of the things I did was I, I drafted an outbound, "no" email for those types of things specifically. That is the body of that email. Because I, want to communicate a bunch of things, which is, "I care about you, you're doing the right thing. I know I could be helpful on this. But I can't because these are the things I'm trying to accomplish. And if I do it, I'm going to jeopardize, accomplishing those things."

And by having that draft email and it, and I have it shortcutted, it's like the keyboard.

Ryan: So it's amazing.

Ashton: It's "T- Y No." Right. So if I put in "T- Y No" there's a shortcut that auto-populates that text. And then I baseline the email response and then augment it slightly.

Ryan: It's so hard to say no to stuff. And like, I love that idea of like, Look, let's be really thoughtful about it and reuse that logic and make sure you're telling people like, yeah, I would love to do this, but I can't. And you know, if you can provide some reasons why, then people won't take it personally.

Leverage culture in your organization to scale your time and mind

Ashton: I think there's another huge productivity hack that also kind of comes with like this notion of scaling your mind. And I think it's around culture and the culture you create within your organization.

Because generally culture has an alignment with mission. Has an alignment with your own personal belief system which is always changing.

So I'm curious about sort of how you go about establishing culture? What are some of your thoughts on culture? Because, you know, happy people are more productive people and tend to be. So I'm curious about what your moves in that

Ryan: hundred percent agree with this. And I think it's the, the challenge and especially for this audience for folks from engineering leadership who were trying to move up and have a bigger impact. And at some point, you know, your impact to scale it, you have to have impact on lots of people. And ultimately culture is the best way to do that.

But my, the, my frustration, as I started to scale Flexport and realized that like, Hey, we really... what is culture? It's like, it's very hand wavy. I didn't see a lot of good definitions for it. But one thing I found was that like, whenever I would reach out to a senior leader, a C level at a public company or a sort of around Silicon Valley and these top companies. If I reached out to the senior leader and asked them a question about like, Hey, can you tell me about sales compensation? They would send me down to someone like four levels down in the org to get an answer. They're very helpful.

But like, but if I ask a question about culture or something in related to culture in some way, they take the call themselves and like usually pretty quickly. So I can tell like, "Hey, this is something that's important to top people in the valley and the top companies."

So I, that was my first signal. And I did a ton of these interviews trying to unpack, you're trying to build a framework for it. So it was less hand wavy. And I came up with a framework that for me works. And I think for a framework to be useful, it has to be easy to remember.

And mine is easy to remember, not because of some stupid acronym, but because I use the six question words in the English language. I think questions are extremely powerful to get ourselves thinking.

And, and our question where the questions are, why like, why are we doing this? What's our mission. What's our purpose? Why are we all here?

The, who was that about talent? What kind of people do we need for this mission? How do we organize ourselves? How do we make sure that we've got the right leveling and HR processes and stuff?

What is our prioritization frameworks? What are we going to work on? How are we going to, what are we going to prioritize?

How, the, how question for me is like, how do we run our meetings? How do we make decisions and getting some good frameworks in there? You can tell a lot about a company culture if you just sit in on a meeting.. and watch how it works. Like is it just the loudest people in the room talking. Is there a bunch of PowerPoints and nobody's talking until three minutes left when they finish and you're allowed to ask a question. So the how question I think is really important.

And then the, when question is really important to culture. When is like, what are our rituals? What is the cadence of this place, your sprints, but your planning cycles, your... hopefully some interesting rituals. Like, it's interesting to look at religions who have done culture for thousands of years, the Catholic church, right? You have like seasonality, have holidays. You have the mass, you have a lot of rituals. I'm not saying we're like creating a cult, but it's interesting to study these things.

And then, and then the where kind of question is like your community, the office environment. How do you make it really safe and inclusive? And for me, like that's the bucket that a lot of people kind of think of when they think culture. But copying it without the other stuff, like you copied Google and you just copied there where you get, like, you're going to get ping pong tables and bean bags. And I don't know if it's going to be like a really productive culture without some... You know, the other stuff matters more in my opinion towards like having an awesome place to work where people are productive.

So, yeah, I think that's a key aspect, but it's, it's important troubleshoot it. You know, that checklist is not like we're perfect to all of this stuff, but it's a great troubleshooting checklist. Like, "oh, what are we not doing well right now"

The power of predictability on company culture & productivity

Ashton: I think the religion parallel is really interesting. I was actually thinking about this and having a conversation about it last week. Where, you're Christian Catholic and it's Christmas time... there's no question, you know, the rhythm. you know, exactly what the rhythm and cadence of that gonna be, you know, the mass. You know, this is going to go.

if you're Jewish and it's Passover, you know exactly what it's going to be. And, because it happens consistently. It's consistency. It's clear expectations. Clear deliverables every single time. And sometimes there's nuance to the problem or nuance to the surrounding ecosystem. But the process through which it works is consistent every time. That bolsters productivity in an extraordinary way.

I did a movie where I was playing a coast guard rescue swimmer. And I went to one of their boot camps for A school. And the key to their bootcamp was that you never knew what was going to come And they were always trying to play a mind game of like, We might, we might be out here for three days, who knows how long this is... and you didn't know whether you were going to go into the pool or you're going to go for a run or you're going to do a pushup

And you're holding these pushups... You don't know how long they're going to make you hold and it messes with you. Yeah. That something's predictable and you know what's coming next. You know how it's going to go it suddenly puts you at ease and opens up your ability to be creative.

Ryan: And it's so hard do, and it's like, you want to do it when you're smaller and in smaller teams, but you want to get this rhythm that syncs like across the company. That lots of your teams are on the same cadence rather than like, you know, this team is doing that. and the other team's doing this.

Is really important. I think why it's early on for companies to recognize this or that, because it's so hard like once you're big company, how are you going to get all these people to change and adopt some new rhythm? You know, you build it when you're small, it's much easier to scale.

So probably one of my mistakes and do-overs is like really value these things from day one. Instead of like, I was probably on year three when I realized like, "Hey, we have a great culture, but like it's not consciously designed with good frameworks."

I think we're going to take an audience question.

What do you think?

Ashton: Yeah, we can totally take your question while we wait for the question to come in...

Networking Hack: Connect through social impact

Ashton: I just wanted to also point out that relative to your reaching out to CEOs and talking about asking about culture... the other extraordinary hack is reaching out to other CEOs and talking about philanthropy.

And you've built philanthropy in as part of your organization. I have philanthropy is very much part of my life. If you're reaching out to talk about philanthropy, you can get a call back from more people than you would ever anticipate and build a relationship set that can be valuable beyond belief for ton of other things. would say that fits in the same bucket is reaching out to talk to people about both...

a hundred

Ryan: percent, by the way.

So, one of our early investors is Bloomberg and the Bloomberg company, and they, I had never met Michael Bloomberg. We were, I think we were one of their best portfolio companies probably, but still like, I'd never met him... doesn't need the money.

But when we started Flexport.org, and started doing logistics for humanitarian causes and non-profits and other, other types of disaster relief, that type of stuff. The next day, I had a meeting scheduled with Michael Bloomberg. He wanted to talk about it. Cause he's, you know, he's starting to have an impact. He doesn't need me to make more money. So I, a hundred percent agree with that. It's a very effective way to build your network. And like doing well by doing good.

You don't have to apologize for it. It's awesome.

Ashton: So Patrick, you can jump back in with a couple of questions and then we have one question to sort of a wrap things up at the end.

Creating a personal mission statement & the "energy audit"

Patrick: Absolutely. Well, the response that you had about a personal mission statement as a filter for decision-making was something that really resonated and set off a pretty extensive discussion of people's personal mission statements.

I was wondering if you could share how you created your personal mission statement? Do you have like the methodology or resources that you use to get there? Cause it sounds like a really powerful decision-making.

Ashton: was actually an exercise I did with someone. There was a woman I met that had a company. And this is kind of, was part of what she did. And she was kind of like a CEO coach type person. And I think it was called the Seed Company. I don't remember completely.

But she, we went through a whole process and it really started out with like... What made me feel alive? What made me feel powerful?

It started a little journey of what are the things that when I wake up, I go. "Man, I can't wait to do!" Like it, it was like moving things from the, "have to do list" on the, I get to do list. And once that I get to do lists was built out, it became abundantly clear what the thing is that not only am I good at. But that I will love to do and that I can have extraordinary impact by doing. And so that was the basic methodology.

Ryan: By the way, we, I do that as well quarterly. I call it an energy audit and I, what I do is I go through my whole calendar, get everything into like a Google sheet or something. And then each meeting that I did, I score it red or green "Did it give me energy or did it take energy away from me?"

And all the stuff that's one cool thing about being a leader and at some scale, and the fact that humans are different... is almost everything that takes away energy from me. There's probably someone else who's different than me that would like love to do something like that. It would give them energy.

And so if you can figure this out with your team. It's, what's great about having a really diverse team of people different interests and backgrounds. Is like, "Hey, you like doing something. I hate doing it. I'm not good at."

And so I got when, when I first started that exercise about two years ago, I think it was like 60% red and 40% green. And now I'm at like 80 or 90% green. Which is probably as good as you're going to get. Like Bill Gates still probably has to go to the DMV. So, you know, there's certain amount of bullshit you have to put up with in life. But I feel like it's been a big change to like my energy levels and my desire to go to work and make stuff happen.

How to avoid being reactive to your to-do list

Patrick: Awesome. I have another follow-up question for both of you just in the spirit of energy redistribution and making decisions on tasks that make you feel alive or make you feel, feel powerful...

I think one of the questions that came up was how do you, how do you avoid being reactive when you get the different to-do's?

And so if you had any insights about the best way to stop being reactive at your list of tasks. When you may be the single point of contact, the person blocking that big thing being done...

Ashton, you were talking about writing your emails first of like the outbound things. Do you have other practices, which you are more proactive versus reactive?

Ashton: I mean, think they were constantly as human beings in, in process of shutting down our reactive behavior. And so that's just a... to me that's just a consistent constant practice of life.

And my mantra around it is that "pain is inevitable, but suffering is a choice."

So when these things come that are painful or unpleasant, I know that if I don't execute against them, they'll turn into suffering. And I, I choose to not have suffering.

And so, if you process it is what it is. and go "all right, this is painful. This sucks. If you leave it there, it's going to become suffering. Because it'll, it'll manifest in some other way eventually.

So let me deal with it while it's pain. That is my non-reactive processes.

Believe in Newtonian physics. So, every action has an equal and opposite reaction. And I probably did something in the world that brought this back to me. So it's, it's mine to deal with.

Patrick: Awesome. Ryan do you have any...?

Ryan: I was a beautiful answer. I don't want to mess it up by adding anything to it.

Patrick: Pain is inevitable. Suffering is a choice. That's really powerful wisdom to go with.

Productivity as your company scales & cultivating sub-cultures within your org

Patrick: So both of you referenced culture several times. So at the talk is like the conditions that create productivity for organizations. And one of the questions that came in, was about like in organizations that have different subcultures with the different teams or different organizations.

And so, an engineering leader is somebody who is, you know, architecting the culture that their team exists in... do you have any insights about how to cultivate that culture as companies grow in size? Or how to cultivate those different micro-cultures that still serve the productivity as a larger organization?

Ryan: I'll take this one. I think it's, it's really important that you allow culture to flourish. And that you don't try to top-down control everything. You want to have that like, I like frameworks, like like-mind because it sets some guard rails and you say, "Hey, these are the things that we're gonna be consistent about. They're gonna fly all over and you can't allow people to deviate from that."

And as a leader, your job as a leader, if you're an engineering leader is to think end to end... just one of our core values at Flexport... but think about the whole system and not just your own team. That's your job as a leader.

But you don't want that to be the job of every single person under you is sort of like the load that you bear for them. So that they can focus and get stuff done.

And so you gotta let culture flourish. And, hopefully, identify. 1 project I've asked... like in a little office of the CEO... and one project I've asked them to do is sort of non scientifically to go across the org and try to find our little micro-cultures and rituals and cadences that are existing in certain teams, and be like, "Hey, which of these are good ideas that we should share and try to propagate in more places rather than... certainly not squash them?"

But they've gotta be certain standards and values that you uphold. And that's the job of like the framework and the higher level of culture of the CEO. The CEO really has to be the defender of the culture.

What question should you be asking yourself right now?

Ashton: I know we're up against time here. Oftentimes we think about questions in the framework of, know, looking for the answer from someone else. And the question we have is a question that is for everyone to be asking of themselves.

And it is just that!

What is the question that you should be asking yourself right now...? and so Ryan, I want to ask you... What is the question that you feel like you should be asking yourself right now?

Ryan: I feel like I have a really good answer in my life to the "why" question. I have a great mission. I mean, it's Flexport's mission. It's super aligned, but I'm in, I'm in love with my work. The "who" question was going awesome. Value system and talent system. We have some work.

But where are where I struggle and where I'm working so hard as like on the "what" on how do we prioritize stuff? We want to do everything. And it's so hard to sit for me to say no to stuff and yeah. I'm such an entrepreneur. And I see people who like a team of three, wants to get something done. I'm like, why would I not let those guys go and do it? But then at the same time, I'm like, we have to focus.

And so really trying to think more about how do I do my prioritization as a company. And I don't have like, a big divide between my personal life and my work. So it's all very much like, okay, what are we going to do? Like this year? Next year? What do we, how do we prioritize that, that list? I'm pretty obsessed with it.

The other one I would probably think about a lot is how do we kill bureaucracy? There's no good word in the English language for bureaucracy. But like, you need a little bit of it. Or else you get a bureaucracy. So I spent a lot of time thinking about that paradox.

Patrick: We have a couple of people jumping in just to give you the return there.

Uh, So Jason says, is this the most important thing I should be doing right now?

That's my question. I think it's a pretty, pretty good question to go with. What's the question for, what's your response to that? What's the question that you want to ask yourself?

Ashton: I think probably the question I should be asking myself is... What have I learned or allowed myself to learn, to create a mental framework that makes me think that the things that I believe should happen or that I'm not the one that should be doing them?

Like, I think that I should be looking at what I've learned, that, is limiting what I'm capable of? And I should be asking myself whether or not what I learned was legitimate? Or what I learned was something that was a reference that was likely misinterpreted by myself?

Patrick: It's a really powerful question for people to consider. You know, we're in a platform of, of learning and are the things that you're learning, the things that actually are serving what you're trying to accomplish?

Ashton: Or are they true? we learned a lot of shit that, come to find out is not real or true.

And then, and we learned a lot of behaviors that are not good. But we think that they're good because they're the only thing we've ever known. And because this is the only life we've ever known. So maybe there's a different framework that will allow us to have a greater output that is more positive for more people.

Patrick: And I think that that's something that companies suffer like are unconscious about as well, in terms of like, "Is how we operate as an organization, how we interact with each other, just product of what we learned or what we've been conditioned to do? Or is there a better way to do it in terms of how you can lead to part company?"

I being told that this is all the time that we have for, for questions.

I just wanted to say thank you both for sharing your insights and sharing your time and helping people tackle productivity, because as you just said, Ashton, you only have one shot or one life here. And to be able to use that time is one of the most precious things that you can do.

So thank you both so much for joining us today.