This Is Me

I guess I’m not your typical CEO.

I probably don’t talk like a CEO. 

You won’t often find me dressing like a CEO. 

Frankly, I don’t particularly care what title I have at work. I’m less concerned with titles and more interested in impact.

The things that motivate me most are working alongside smart people, solving challenging problems, constantly learning new things, and having the greatest impact possible.

I have simple tastes. If given the choice between a meal at an expensive three star restaurant and a kids meal at McDonalds, I’ll take the kids meal (6 piece nuggets with sweet and sour sauce FTW). 

I don’t want/need credit for anything.

I’m not here to power trip or micromanage. 

I believe in the inverted org. When I’m in a leadership position, I’m at the bottom of the pyramid. Individual team members are at the top. I’m here to serve you. 

I believe in establishing agreements around clear responsibilities and then holding people accountable for the things they’ve committed to.

I value principles, people, product, and profits (always in that order). I believe that profit maximization in any company only occurs after you get the first 3 priorities right. 

I have a strong internal north star. I am grounded in my beliefs and my self worth. 

I believe that the original Pete’s Dragon is hands down the best movie ever made.

I believe that having fun is important and that we shouldn’t take ourselves too seriously.

I have very little patience for internal politics. 

I will tend to challenge statements like “we’ve tried that before”, or “that won’t work here” when they are based on untested assumptions or older data.

I’m a big fan of rapid iteration. Let’s try a bunch of stuff, keep the stuff that works, and then iterate on or ditch the stuff that doesn’t. 

I refuse to work with toxic people (No matter how long you’ve been at the company, or what role you have, or how impactful you’ve historically been).

I value diversity. Diversity in people, roles and experiences all leads to better decisions, better products, better work environments, and better companies.

I value ownership. When you make a mistake, own it.

I value clarity. If something is unclear, ask questions until you have all of the context you need to do your best work.

I value alignment. Let’s be united in our cause. We will rise and fall collectively together and find valuable learning opportunities in both our successes and our failures.

I will no doubt make mistakes. When I do, call me out on them. I will gladly apologize and own my shortcomings.

For those of you on my team:

If you ever feel unheard, frustrated or hurt, I am here to listen. 

If you’ve hit a roadblock, I will help you get unblocked. 

If you have questions or concerns, my door is always open. 

Most of all, know that I genuinely care. I care about you. I care about our customers. I care about the product we are building. I care about the company that we work for.

Oh, and I love musicals. 💖

“Powerful” notes

I highly recommend “Powerful” by Patty McCord as a very worthwhile read for anyone in leadership. Here are my notes from the book:


  • Be ready at any moment to cast aside your plans, admit mistakes, and embrace a new course.
  • People have power; Don’t take it away. A companies job isn’t to empower people; it’s to remind people that they walk in the door with power and to create the conditions for them to exercise it.
  • The Netflix culture wasn’t built by developing an elaborate new system for managing people; we did the opposite. We kept stripping away policies and procedures.
  • Most companies are clinging to the established command-and-control system of top-down decision making which is in enormously costly, time-consuming, and generally unproductive.
  • This older approach to leadership clings to false assumptions about human beings: that most people must be incentivized in order to really throw them selves into work, and that they need to be told what to do.


  • I’m going to challenge all of the basic premises of management today: that is about building loyalty and retention and career progression and implementing structures to ensure employee engagement and happiness. None of that is true. None of this is the job of management.
  • A business leaders job is to create great teams that do amazing work on time. That is it. That is the job of management.
  • If I could pick one course to teach everybody in the company, whether they’re in management or not, it would be on the fundamentals of how the business works and serving customers.


  • We wanted all of our people to challenge us, and one another, vigorously.
  • We wanted them to speak up about ideas and problems; to freely pushback, in front of one another and in front of us.
  • We didn’t want anyone, at any level, keeping vital insights and concerns to themselves.
  • We (as an executive team) made ourselves accessible, and we encouraged questions.
  • We engaged in open, intense debate and made sure all of our managers knew we wanted them to do the same.
  • If people have a problem with an employee or with the way another department was doing something, they were expected to talk about it openly with that person, ideally face-to-face.
  • It was unacceptable to talk about people behind their back’s or to come to then to complain about a colleague.


  • We communicated honestly and continuously about challenges the company was facing and how we were going to tackle them.
  • People need to see the view from the C suite in order to feel truly connected to the problem-solving that must be done at all levels and on all teams.
  • If you stop any employee, at any level of the company, in the break room or the elevator and ask what are the five most important things the company is working on for the next six months, that person should be able to tell you, rapid fire, one, two, three, four, five, ideally using the same words you’ve used in your communications and in the same order.


  • We wanted everyone to understand the change would be a constant and we would make whatever changes of plan, and of personnel, we thought necessary to forge a head at high-speed
  • We wanted people to embrace the need for change and be thrilled to drive it.
  • We wanted people to feel excited to come to work each day, not despite the challenges but because of them.
  • It’s not cruel to tell people the truth respectfully and honestly.
  • The most important thing about giving feedback is that it must be about behavior, it also must be actionable.
  • Proactively letting people go was one of the hardest, probably the single hardest, component of the Netflix culture for managers to become comfortable with. But most of them did.


  • We did away with virtually all policies and procedures. We didn’t do it in one fell swoop. We did experimentally, step-by-step, over the course of years.
  • As we stripped away bureaucracy, we coached all of our people, at all levels and on all teams, to be disciplined about a fundamental set of behaviors.
  • It isn’t a matter of simply professing a set of values and operating principles. It’s a matter of identifying the behaviors that you would like to see become consistent practices and then instilling the discipline of actually doing them.
  • We fully and consistently communicated to everyone at Netflix the behaviors we expected them to be disciplined about and that started with the executive team and every manager.
  • We experimented with every way we could think of to liberate teams from unnecessary rules and approvals.


  • The company was like a sports team, not a family.
  • Creating a culture is an evolutionary process. Think of it as an experimental journey of discovery.
  • The best thing you can do for employees is hire only high performers to work alongside them. it’s a perk far better than Foos ball or free sushi or even a big signing bonus or the holy Grail of stock options. Excellent colleagues, a clear purpose, and well understood deliverables: that’s the powerful combination.
  • When we were interviewing people, we told them straight out that we were not a career management company, that we believed people’s careers were theirs to manage, and that while there might be lots of opportunities for them to advance at the company, we wouldn’t be designing opportunities for them.


  • Great teams are made when every single member knows where they’re going and will do anything to get there.
  • Great teams are not created with incentives, procedures, and perks.
  • Great teams are created by 1) hiring talented people 2) who are adults and want nothing more than to tackle a challenge, and then 3) communicating to then, clearly and continuously, about what the challenge is.
  • There is no better reward for team members than making a significant contribution towards meeting a challenge.
  • Great teams are made when things are hard.


  • You’ve got to hire now the team you wish to have in the future.
  • finding the right people is not primarily about “culture fit”. People can have all sorts of different personalities and be great fit for the job you need done.
  • When you hire someone and it turns out that they can’t do the job, the problem is with the hiring process, not the individual.
  • I decided to throw out the traditional recruiting practice and create a headhunting firm with in the company.
  • We focused on finding the best creative talent with the skills to execute, and then giving those creators the freedom to realize that vision.
  • We developed “new employee college”. For one whole day each quarter every head of every department would make an hour long presentation on the important issues and developments in their part of the business to an audience of our new hires.
  • At Netflix we had three fundamental tenants to our talent management philosophy. First, the responsibility for hiring great people. Second, for every job we try to hire a person who would be a great fit, not just adequate. Finally, we would be willing to say goodbye to even very good people if their skills no longer matched the work we needed done.
  • If you focus intently on hiring the best people you can find and pay top dollar, you will almost always find that they make a much more in business growth than the difference in compensation.

Caution: Work fills the space you give it

For most of my career I’ve prided myself on being able to restrict my work schedule to just 40 hour per week. Most of my career I’ve been able to stick to this. I even co-wrote a blog post about it at one point.

I took this past Monday off to have an extended weekend with my family. When Monday came, instead of enjoying time with my family, I was stressing about all of the stuff that was likely piling up at work.

Upon reflection, I’ve come to the realization that I’ve been consistently working too many hours each week and that it’s probably not long-term healthy for myself or my family. After coming to this realization, I started taking some steps to help me get back to a more manageable work schedule, which include:

  • Removing the Slack app from my phone – My principle for some time has been to only have the app on my phone when I travel for work, and yet somehow the app found it’s way back to my phone and I found myself checking in during non-work hours.
  • Establishing a clear work schedule – I’ll try and start consistently each day at 8am and wrap up at 5pm (with a 1 hour break for lunch).
  • Stop working weekends – Unless there is a fire (which there rarely is) I’m going to try and avoid working on my weekends.
  • I blocked off two days as no meeting days – I blocked off Wednesday and Friday on my calendar as days where I can just catch up on work without having any meetings to break up my day.
  • Meeting audit – I realized that I’ve been over-committing myself to too many regularly scheduled meetings. I’m going to be scaling back the number of meetings that I attend each week.
  • Backing out of design discussions – For now (while I’m the acting Manage Group lead) I will be staying out of most design discussions and leaving them in the capable hands of our Manage Group designers.

The thing is, none of this happened suddenly. It just sort of crept up on me slowly. With time, I just stopped regulating each of these areas and eventually it added up.

I share this openly here for three reasons:

  1. To call myself out.
  2. To support anyone else who notices similar patterns in their own work routines and wants to take steps to correct them.
  3. To remind my future self that without self-regulation, work fills the space you give it.


I don’t do comments on this site, but if you have thoughts, I’d love to hear them. You can email me at

Tiny House Inspiration

Over the years I’ve collected the following list of tiny houses that inspire me – in no particular order:

Photo by Mariko Reed – Topanga Cabin
Photo by Shigeo Ogawa – Near House
Photo by Sol Haus Design – Vina’s Tiny House
Photo by Beppe Giardino – Tre Livelli
Photo by Tiny Home Builders – Tiny Studio
Photo by David Patterson – Vail Treehouse
Photo via Foster Huntington – The Cinder Cone
Photos via Carla Rodriguez – Beacon Cabin
Photo via Getaway House, Inc. – Clara
Photo by Tiny Living Homes – Tiny Living
Photo by Dan Hoffman – Nest
Photo via Greenleaf Tiny Homes – Kootenay
Photos by Garett and Carrie Buell – Alpha

Coach Bill Campbell

I never met Bill Campbell. To be honest, I had never even heard about him until I heard Eric Schmidt speak his praises on the the Tim Ferris Podcast.

I picked up a copy of Trillion Dollar Coach and I’m so very glad I did. This book is easily in the top 5 books I’ve ever read. It’s right up there with Creativity Inc.

I don’t share book reports very often. Probably only 1 out of every 100-150 books I read. But this is one book that I felt compelled to share.

I’ll do my best to theme selected highlights vs. presenting things linearly.

Great coaches:

  • Listen intently.
  • Look for patterns.
  • Assess strengths and weaknesses.
  • Ask questions instead of offering advice.
  • Hold a mirror up so we can see our blind spots.
  • Hold us accountable for working through our sore spots.
  • Take responsibility for making us better without taking credit for our accomplishments.
  • Notice body language and side conversations in addition to listening.
  • Act as a sounding board.
  • Relate stories that help us gain perspective, draw insight, or make a decision without telling us what to do.
  • Keep opinions about product and strategy to themselves.
  • Make sure the team is communicating.
  • Bring disagreements and tensions to the surface.
  • Connect the dots with various stakeholders behind the scenes so that when big decisions come up everyone is on board—whether they agree or not.
  • Don’t voice opinions about which way a decision should go—Just push for the decisions be made.
  • Listen, observe, and feel the communication gaps between people.
  • Lie awake at night thinking about how to make us better.

On coaching

  • The best coach for any team is the manager who leads that team.
  • I’ve come to believe that coaching might be even more essential than mentoring to our careers and our teams.
  • It’s up to all of us to coach our employees, our colleagues, and even sometimes our bosses.
  • Mentors dole out words of wisdom, coaches roll up their sleeves and get their hands dirty.
  • Purpose, pride, ambition, love, family, money, attention, power, meaning, and ego are all primary motivations to consider when coaching someone else.
  • It’s often the highest performing people who feel the most alone.

Excellence in teams comes from

  • Psychological safety
  • Clear goals
  • Meaningful roles
  • Reliable teammates
  • Confidence that the teams mission will make a difference

On trust

  • Perhaps the most important currency in relationship—friendship, romantic, familial, or professional—is trust.
  • Trust means people feel safe to be vulnerable.
  • Trust means loyalty.
  • Trust means integrity.

Wisdom for leaders

  • Leaders lead. You can’t have 1 foot in and 1 foot out. If you aren’t fully committed then the people around you won’t be either.
  • In business there is growing evidence that compassion is a key factor to success.
  • Go to extraordinary lengths to build safety, clarity, meaning, dependability, and impact into each team you lead.
  • Create a climate of communication, respect, feedback, and trust.
  • Listen. Pay attention. This is what great managers do.
  • Managers authority emerges only as the manager establishes credibility with subordinates, peers, and superiors.
  • Your title makes you a manager. You’re people make you a leader.
  • “Get the one on one right” and “get the staff meeting right” were top on Bill’s list of the most important management principles.
  • Failure to make a decision can be as damaging as a wrong decision.
  • Never put up with people who cross ethical lines: Lying, lapses of integrity or ethics, harassing or mistreating colleagues.
  • Letting people go is a failure of management, not one of any of the people who are being let go.
  • It’s a manager’s job to push this team to be more courageous.
  • Don’t just be a dictator assigning tasks, pair people up!

On Teams

  • Coaching is the best way to mold effective people into powerful teams.
  • Start treating teams, not individuals, as the fundamental building block of the organization.
  • Teams need to act as communities, integrating interests and putting aside differences to be individually and collectively obsessed with what’s best for the company.
  • When internal conflict arises the trick is to corral rivals into a community and get them aligned, marching toward a common goal.
  • When team members can’t break the tie themselves, it falls on you to make that decision.
  • When faced with an issue, his first question wasn’t about the issue itself, it was about the team tasked with tackling the issue. Get the team right and you’ll get the issue right.

On meetings

  • He’d start by asking what people did for the weekend.
  • Before decisions were made everyone weighed in, regardless of whether the issue touched on their functional area or not.
  • Bill would often meet with multiple people before an important meeting to find out what they were thinking. This gave members of the team the chance to come into the room prepared to talk about their point of view.
  • When labelled a debate rather than a disagreement, participants are more likely to share information.
  • Having a well-run process to get to a decision is just as important as the decision itself, because it gives the team confidence and keeps everyone moving.

On 1:1’s

  • Bill would always start with a hug.
  • Next he’d ask about your personal life, family, and non-work stuff.
  • Bill would write five words on a white board indicating the topics to discuss that day. The words might be about a person, a product, an operational issue, a prospective customer, or an upcoming meeting.
  • Bill took great care in preparing for one-on-one meetings.
  • Bill typically discussed performance, peer relationships, teams, and innovation.
  • Deliver tough messages with respect, warmth, and candor.

Coach Campbell

  • Was tremendously respected and loved.
  • Lit up the room whenever he walked in.
  • Was a straight shooter.
  • Was a hugger.
  • Was generous.
  • Like to help people.
  • Cursed like a sailor.
  • Treated everyone with respect.
  • Believed in diversity on teams.
  • Preferred operating behind the scenes.
  • Saw through the title to who a person was.
  • Always strived for a politics-free environment.
  • Always gave you a call back when you left voicemail.
  • Demanded commitment, passion, and loyalty.
  • Cared about his people fiercely and genuinely.
  • Was always there for you when you needed him, no matter what.
  • Had a way of making you feel better, even if he was sharing bad news.
  • Is sorely missed by many.

As I said, I never met Coach Bill Campbell, but after reading this book I wish I had.


I don’t do comments on this site, but if you have thoughts, I’d love to hear them. You can email me at

Japan, April 2019

Two weeks ago I travelled to Japan for the first time. I was there for 7 days. It was everything that I had hoped for. Below I’ll share a few select memories.

Shibuya Crossing

So crazy…

Roppongi Hills Mori Tower & Museum

Akira in the Streets

Vending Machines

Capsule Hotel

First Meal

Cherry Blossoms

Hie Shrine



Good Food

Toilets 😳


TeamLab Borderless


Meiji Shrine

Street Ads

This ad/song played literally every 120 seconds on the streets of Shibuya where I stayed.


Ueno Zoo

Everything I Wish I knew About Stock Options 15 Years Ago

Stock Options
Photo by Suzy Hazelwood

Disclaimer: I’m a designer. I’m not an accountant or a lawyer. When it comes to stock options, if you’re not careful you can end up in a mess tax-wise. Be sure to consult with an accountant and a lawyer before considering any of the scenarios below.

Slow your roll…

You just received a job offer from a startup that includes a $120/yr salary and 20k options that vest over 4 years (with a one year cliff). How do you ensure that those options don’t just slip through your fingers?

Before you start browsing brochures for your Scrooge McDuck sized money vault, here are some practical tips that you should consider:

Don’t be like most startup employees

Most startup employees have no idea how stock options work. They blindly sign agreements, have no idea what liquidation strategies are available to them, and often times forfeit all of their options by leaving the company without exercising anything.

Learn the terminology

Here’s a quick primer:

a. Stock Option
It’s called an “option” for a reason. A stock option is not the same thing as “stock”. With stock options, you are not given stock, you’re giving the option to purchase stock once your shares have vested. Once you leave your company, you typically only have 3 months to execute your options, before it disappears.

b. Strike/Grant/Exercise Price
The fixed price you’re allowed to purchase stock at. This price stays the same during the life of your options grant. If the company that you’re working at is growing, the delta between your strike price and the 409A price and market price will continue to grow.

c. 409A Price
Private companies that issue stock options are required to periodically perform an evaluation of the companies value. Technically this should happen after any event that materially affects the value of the company. Typically though this process happens once per year. From this evaluation, a price per share is estimated. The 409A price is typically lower than the market price.

d. Market price
The per share price the market is willing to pay for your companies stock.

e. ISO vs. NSO
There’s quite a bit of nuance here. Instead of listing everything out, I’ll just link to this article. The biggest thing to keep in mind are the tax implications of the type of options you have.

f. Grant
The amount of stock options you’re given. In the scenario above this would be 20,000 options.

g. Issue/Grant Date
The date you were issued your grant.

h. Vesting Schedule
The schedule by which your stock options become exercisable. Having a 4 year vesting schedule with a one year cliff is super common. In our example above, that would mean that 5000 shares would become exercisable after one year at the company and approximately 416 shares would become exercisable to you each month thereafter for the next 3 years.

i. Cliff

The period of time before your first chunk of options becomes exercisable. After the cliff, a smaller pool of your options generally start becoming executable on a monthly basis

j. Exercisable

The point at which you can purchase some portion of your options.

k. Exercise Date

The date you purchase your options.

l. Expiration Window

The date at which your options expire. Typically this is either:

  • 3 months after you leave the company
  • 10 years after your issue date
  • The date you were fired (if that applies)

m. Cap Table

The list of people who already own stock in your company. This may include founders, investors, advisors, other employees who have already exercised their options.

n. Options Pool

Stock options are granted from an options pool. From a company ownership standpoint, an options pool is necessary in order to prevent constant churn or dilution as options are granted and then expire.

o. Liquidation Preferences

Depending on the round and the state of your company when it raises money, liquidation preferences can be added as bargaining chips that can have an impact on your options when it comes to a sale or acquisition. Essentially this means that some investors will be able to get more money for each share they hold, and likely will be able to sell their shares in the event of the sale of your company before you can.

p. Dilution

Any time additional shares are added (typically as a result of fund raising rounds) there is going to be dilution of the stock value for all stock owners across the board. Basically this means that (at least temporarily) your individual stocks, or options will be worth less money.

q. Equity Investment Plan Document

This formal document outlines the bylaws of a companies stock option program. You’ll need a copy of this if you ever wish to sell your shares.

r. Option Agreement Document

This legal document outlines everything about your particular stock grant. This document will also be needed if you ever go to sell your shares.

s. Exercise Agreement Document

Once you exercise stock options, it is done through an exercise agreement. You’ll also want to hang onto this document.

t. Right of First Refusal

If you have a contract to sell your private stock to a third party, the company typically has a clause that they can purchase your shares at the same price that the third party. This ensures that the company has control over who is added to their cap table.

Know the Tax Implications

I can only speak from my experience. Again, if you’re considering purchasing options, you’ll want to consult with an accountant and a lawyer.

Long-term vs. short-term capital gains tax

In the U.S. if you purchase options and hang on to them for a year before you resell them, you will pay long-term cap gains taxes which as of 2018 is a flat 15% rate. If you purchase your options and sell them before a year passes, you’ll pay short-term cap gains tax which is effectively your personal tax rate 25-35%.


With ISO options you wait to pay the taxes on the sale of your stock until April 15th of the following year. When you sell NSO options, you pay the taxes immediately upon purchase.

AMT tax rate

This is a tricky bugger to figure out and plan for. 🙂 Basically, if you exercise your options and hold on to them for a year (in order to qualify for long-term capital gains tax) come April 15 you’ll still need to report the purchase of your options and likely pay AMT taxes on them. Talk to your accountant. They should be able to help estimate this for you.

Warning: If the delta between your strike price and the current 409A price is large, the AMT taxes that you’ll be required to pay (prior to selling your stock and recouping any of the money you spent to purchase your stock) may be high (depending a number of variables, like your household income level). You’re absolutely going to want to factor this into your decision to exercise and hold stock.

Get the big picture

Mapping everything out will help you get a better picture of what sort of return you could see from your options.

I created a sheet to help you plan out your liquidation options:

Stock Options Planner

If you’d like to use this sheet, just go to “File” and select “Make a copy” within this Google Sheet.

Liquidation options

Finally, since the company you work for is not a publicly traded company, how do you go about actually selling your private stock? You actually have quite a few options.

1) Forward/accelerated vesting

First, going into a new role it’s helpful to be aware of the option of forward vesting shares. If you’ve got the cash, and the company is open to it, this is your best option, as it avoids all tax hassles down the road.

Here’s how it works:

Taking our example above. Let’s say you’re in the process of joining a new company. They’ve extend a grant of 20,000 options at a strike price of $0.10/share. Chances are the 409A price is also at or near $0.10/share as well.

With forward vesting you purchase all of your options ahead of time. Since there is no delta between your strike price and the 409A price, you don’t pay any taxes. So in this scenario, you’d still have a 4 year vesting schedule with a 1 year cliff. You’d pay $1500 up front, but once you pass your cliff, you start vesting stock instead of options.

There’s a decent chance that the company you’re joining has never heard of this. They may need to consult their lawyer.

But what happens if you leave the company before all of your stock has vested you might be wondering? Not to worry. There is a clause in the agreement that the company can purchase back any unvested stock from the employee at the price the employee paid if the employee leaves the company before they are fully vested.

It requires a little bit of extra paperwork on the company, but can be a win, win situation (assuming you have the cash up front to pre-purchase all of your options).

2) Your company goes public

This is an easy one. Typically there will be a window of time post IPO where you cannot liquidate any of your shares, but after that you can sell your stock at any time at the current market value.

3) Your company is acquired

This is another easy scenario. But again, be mindful of liquidation preferences. Chances are that if you received employee stock options that you have common stock which receives it’s distribution last, and often at multiples less than preferred stock.

4) Sell to someone already on the cap table

If your company isn’t planning on going for an IPO and there’s no sign that they are planning on selling in the near future, a next best step is to reach out to them to see if anyone on the existing cap table is interested in picking up some additional shares. This is in their best interest because it means that no new investors are added to the cap table. It’s in your best interest because it saves you from having to hunt for someone else to buy your stock, and prevents you from having to pay a commission fee.

5) Piggy back off primary rounds

If your company is raising money, it’s almost guaranteed that some people in the company are taking some money off the table. If you can get in on that, this is an easy was to liquidate some of your holdings.

6) Secondary rounds

It’s becoming more and more common for privately held companies to do secondary rounds where employees and early investors have the option of cashing out.

7) Buying yourself 103 days

If you have ISO stock, one handy trick you might try and leverage is to purchase your stock on January 1st. Since you don’t owe taxes until April 15 of the following year, this buys you 3+ months the following year to find a buyer for your stock, thus qualifying you for long-term capital gains tax AND preventing you from having to pay taxes before a sale.

Note: I’ve not actually tried this. You’ll have to let me know if you ever do.

8) Private stock marketplaces

If you work for an exciting startup—one that investors are eager to get a piece of—there are multiple private stock marketplaces where you can list your stock:

Just be aware that just because you list your stock doesn’t mean that you will sell it. There is also typically a commission fee that you’ll pay when you sell your shares (5% is typical but you may pay more or less depending on how popular the company is that you work for).

9) Extending your window

Finally it’s worth noting that if you’re leaving your company on good terms and you don’t have the resources to purchase your vested shares (and pay the corresponding taxes) you should definitely check with your company to see if they’ll extend your expiration window. This is becoming increasing popular. More and more tech companies are extending their expiration window out as much as 10 years.

Just know that by law, 3 months after you leave your company your ISO stock options will convert into NSO options.

I hope that was helpful

If you have any thoughts or feedback I’d love to hear it. You can email me at

If you’re interested in receiving additional posts like this on a weekly basis, just toss your email in the form at the top of this page. 🤘

Hold Regular Negativity Audits

Negative influences
Photo by Tim Gouw

What’s a negativity audit?

It’s a simple self-evaluation that when held on a regular basis can highlight negative influences in your life.

How does the audit work?

It’s simple. Just ask yourself these 3 questions:

  1. What 3 people leave me feeling the most negative after I spend time with them?
  2. What 3 songs leave me feeling the most negative after I listen to them?
  3. What three things that I’ve watched or read recently leave me feeling the most negative?

Try and answer each of these questions completely and honestly every time. The most is intentionally bolded in each of these. You may not hang around net-negative people at all, but who are “the most” negative 3 people you hang around.

I’ve found it handy to record my answers in the same place every time (either in a journal or in dropbox paper or Google Docs). That way I can look for patterns.

What are the benefits?

I’ve been able to identify and eliminate quite a few things from my life which I believe have had an outsized impact on the quality of my everyday life. One simple example was when I realized how much of a negative influence consuming the news has on me. 3 years ago I stopped watching the news altogether and I can attest to the fact that my life is better for it!

How do I know if something is negative or not?

Common negative behavior includes:

  • abuse (verbal, physical, emotional)
  • gossip
  • fault finding
  • insults
  • discrimination
  • lying
  • sabotage
  • theft

In general, negative interactions can leave you feeling:

  • fearful
  • guilty
  • sad
  • superior
  • shameful
  • depressed
  • inadequate
  • vulnerable
  • jealous
  • fat/ugly

How Often is “Regular”?

That is up to you. I generally do this once a quarter.

Handy Tip for Creating Full Length Screenshots

There are a number of tools out there that specialize in creating full-length screenshots of a website, but did you know that you can also use Chrome’s Developer Tool to accomplish the same thing?

Check it out, first pull up any website:

Website Example

Next, right click and select “Inspect”:

Chrome Dev Tool Inspect

Once the dev console is showing hold down command + shift + p and you should see the following menu:

Type “screen” in the top search box and select the “Capture full size screenshot” option:

Chrome capture screenshot

Then sit back and let Chrome do it’s thing. Within a few seconds you should see a full-length screenshot pop into your downloads folder:


Updated November 28, 2018.

Clever Onboarding Video

This week my exploration took me to the onboarding flow for Asana. Once you sign up and confirm your email you hit this screen:

Asana Intro Video

Note: I clicked play for this animated gif, but the video actually auto plays normally.

I thought this was clever for a couple of reasons:

First, the video auto plays but the sound is turned off and captions are turned on. I really appreciated this approach. I’ve not seen anyone else do this within the context of an onboarding flow before.

Typically I’m not a fan of intro videos because in my experience they tend to rarely get played and auto playing videos that have sound can be a bit of a turn off—especially depending on the environment that you’re in when you go through the flow.

This approach was novel enough to me that I found myself watching the entire video.