Inside My Brain

Thoughts about startups, tech, marketing, and life

AUTHOR: Mike Chan

The power of focusing on fewer tasks

I’ve been on a never-ending search to find a system that works for managing my short term tasks. I’ve experimented with different methods in the past – using my calendar as my daily task manager, writing daily tasks down by hand, and others – but they haven’t seemed to increase my productivity or made me more comfortable with my progress.

I’ve used Asana in the past, and currently use Trello to track all of my projects and tasks. Both are great tools (see the comparison article I wrote here) that certainly help me stay organized and not forget about anything that I need to do. But it’s less about logging the tasks and more about executing them to completion.

I always seem to have a bunch of overdue tasks in my Trello cards, and all I do is just keep pushing back their due dates. Shitty.

Trello Overdue Cards Blurred

Ugh. Lots of tasks overdue, and it’s usually much worse.

This week, I tried something different.

I selected four big tasks that I would absolutely complete this week.

There will still other weekly maintenance tasks, like analyzing web traffic, social media, and writing this blog post, that I would finish by week’s end. But the four highlighted tasks were larger To-Dos that were either started a while ago and never completed, or an important project that needed to get done soon.

To log these tasks, I created a new Trello board, starred it, and only put those four tasks on that board. That’s it.

No other tasks or lists to distract focus from those tasks. Four tasks on a little lonely Trello island.

I have to say – so far, so good.

None of the tasks are fully complete, but they are all 90-95% done, and I still have today and Sunday (when I always put in a couple of hours of work) to finish them off.

The key here is to really focus and put more time into a fewer number of tasks.

In the past, I would start writing a blog post, get sick of writing it, then start another post, get sick of that, then go on and do something else. After repeating this process for days, if not weeks, all I would have is three or four quarter-written drafts and multiple Trello cards telling me how much work I have to do.

This week, I selected one of those unfinished blog posts and focused on completing it. Lo and behold, it’s almost ready to go!

Not only will I get to archive that Trello card, but the progress I’m seeing gives me a shot of dopamine and gets me amped up to complete the next task.

Maybe I’ve finally found a system that works for increasing my productivity.

How do you manage your daily and weekly tasks? What has worked for you? I’d love to hear your thoughts in the comments!

Lessons learned from Isaiah Thomas’ letter to Boston after being traded

Bradley Beal, Isaiah Thomas

Even if you’re not an NBA or sports fan, I think this story is something you’ll appreciate.

Isaiah Thomas is the former point guard for the Boston Celtics and was recently traded to the Cleveland Cavaliers. He recently penned a heartfelt letter on The Players’ Tribune telling how it all went down, how devastated he was, and how much his time in Boston meant to him. It’s an amazing read, so take 5 minutes and read it now – I’ll still be here when you get back.

Isaiah was the last player drafted – the 60th player overall – in 2011. Players drafted in this position rarely last in the NBA, and if they do, they’re typically relegated to the bench and traded many times.

Isaiah is 5’9″, tiny by NBA standards.

After stints in Sacramento and Phoenix, Isaiah was traded to Boston, where he became an All-Star and MVP candidate and led the team to the first seed in the Eastern Conference last season.

His sister Chyna tragically died in a car crash during last season’s playoffs. He flew to the West Coast to attend her funeral, then flew back to Boston to play the next night. And he scored 33 points and logged 9 assists.

Isaiah played months through a nagging hip injury that forced him out of the playoffs. He left his heart and soul on the court every day.

Yet he still got traded.

The guy he was traded for is Kyrie Irving, who is essentially basketball royalty.

He was drafted #1 overall that same year Isaiah was drafted. He played his college ball at Duke. Playing along side LeBron James, he’s been to the NBA Finals three years in a row and won the championship two seasons ago. Yet he wasn’t happy and demanded a trade.

While supremely talented, he’s been criticized as sometimes being lazy, playing bad defense, or being a ball hog.

Sounds like quite the opposite of Isaiah, no?

There are a few lessons that I took away from this situation and reading the article.

It doesn’t matter what deficiencies you have or what others think of you. If you work hard and keep learning and grinding, you can succeed no matter what hurdles are in your way. 

All odds were against Isaiah lasting in the NBA. Yet he continued to work hard and improve his craft, so much that he became one of the top players in the league.

Things can change at a moment’s notice. 

For better or worse.

Take nothing for granted. You can do everything right but bad things can still happen. Stay humble and just keep working.

Be appreciative.

I’m sure Isaiah was angry, and he could have lashed out against the organization and city that he’s leaving. But he expressed his appreciation and love. That’s class.

Ambition is a powerful thing.

It seems as though Kyrie Irving’s situation was amazing. He’s won an NBA championship and has perennially made the NBA finals. Yet he still wasn’t satisfied with this.

I’ve written about the difference between happiness vs. satisfaction a couple times in the past – see here and here. Kyrie’s ambition to “be the man” and play second fiddle to Lebron James led him to request a trade. Was he appreciative of this situation in Cleveland? Maybe. But was he satisfied? Nope.

On the other hand, Isaiah’s ambition to be a great player, despite his deficiencies, got him to where he is today.

Isaiah’s blog post is one of the most personal, heartfelt articles I’ve read in a long time. The guy has worked so hard and laid it on the line every night, yet he still got done wrong. Life’s a cruel thing sometimes.

All you can do is appreciate what you have and keep moving on.

Photo courtesy of Keith Allison on Flickr

Think for yourself

Venture capitalist Leo Polovets tweeted the above statement out a couple of weeks ago, and I couldn’t agree more.

I know many people who are contrarian for the sake of being contrarian.

It’s good to be different, but only if it makes sense to be. It can be easy to be contrarian – just say the opposite of what others are saying. But you don’t want to be that kind of contrarian.

I also know many people who don’t have a unique or independent thought at all. They go through the ropes, agree with everyone, do what is expected of them, and nothing more.

I think that’s worse.

Independent thinking is the result of true analysis and understanding.

If you think independently, sometimes you’ll be contrarian, other times you won’t. Sometimes you’ll be right, other times you won’t.

What you’ll have is a say, an opinion, an input. And if that input is well researched and backed up, you’ll get respect for your thoughts, regardless of whether you’re right, wrong, contrarian, or conformist.

Think independently about that, and let me know what you think!

Putting your life and career into perspective

Last weekend I returned from an amazing two-week family vacation in Thailand.

This vacation allowed me to take time away from work (I didn’t even bring my laptop!), reflect on what’s going on in my life, and enjoy time with family.

We spent a few days in Ko Samui, where my cousin got married in a beautiful ceremony. A bunch of our family stayed in a beach villa and had a great time.

We then trekked up north to Chiang Rai and Chiang Mai to hang out with elephants, tigers, nature, and lots and lots of Thai food. Check out my “Le Tigre” below. 🙂

Zoolander would be proud


While on the trip, Steve Blank wrote a great blog post titled “Working Outside the Tech Bubble.”  The gist of the article is that because he works in tech, he sometimes forgets that most of the world lives outside of the Silicon Valley bubble. He has a summer home in New England, and most of his neighbors don’t know or don’t care about who the ex-CEO of Uber is or what venture capitalist funded which hot startup.

Reading this made me think about perspective.

Like I mentioned in my last blog post, I’ve been feeling guilty about not doing enough in both work and my personal life. I often look at others’ success and doubt myself and my decisions.

But when you put things into perspective, no matter how tough things get, it’s never that bad.

I’m not saying to look down on others’ hardships. It’s more about appreciating what you have and all of the options in front of you.

While in Thailand, we were amazed at how cheap things are. Uber rides were all less than $3, most meals were cheaper than $5 per person, and hour-long massages cost around $8.

Yet all of those low prices may be normal or expensive for the Thai citizens. And those citizens are working really hard to make those wages that are super cheap to us.

Many Thai people live in villages, without the comforts of running water and electricity that we are accustomed to.

There’s no doubt that people in the US still face hardships everyday. Crime, racism, and poverty are still rampant in society.

But by simply being born or living in the US, we’re luckier than 95% of people in the entire world.

We don’t have to face the threat of a suicide bomber day in and day out. Most of us have a roof over our heads with running water and electricity.

So whenever things get tough, I like to put things into perspective and appreciate how lucky I really am.

Sure, my career isn’t going exactly how I’d like it to go. Things aren’t perfect.

But it’s always helpful to take a step back and look at what I have – an amazing family, a beautiful home, good health, and lots of opportunity – rather than what I don’t have.

It’s good to put things into perspective once in a while.

The importance of taking time off from work

Career regret

A couple of weeks ago, a story about a woman who took a couple of days off from work to focus on her mental health went viral.

In summary, Madalyn Parker, an engineer who works for live chat company Olark, wrote an email to her team that said she was taking the next couple of days off to focus on her mental health. The company’s CEO responded, praising her for her email and stressing how important it is to take time off.

This is an ongoing issue in the startup world, where 80-hour work weeks are often the norm and considered cool. David Heinemeier Hansson, the creator of Ruby on Rails and CTO of Basecamp, completely disagrees.

In the early days of my career in consulting, I used very few of my vacation days, and the thought of taking time off to work on my mental health never even crossed my mind.

When I was working for the Washington Capitals, the seasonality of the job didn’t really allow us to take any days off between September and May (when the Caps would crap the bed in the playoffs). We would take some time of in the summer, but even then I didn’t take full advantage of it.

I thought that taking days off would slow my ascent up the ladder. If I was the hardest working person in the company, I would get promoted and get more responsibility and authority.

Looking back, all that crap didn’t matter.

Unless you have a terrible manager, no one is going to ding you for taking days off. And as important and valuable as you are, your big company will go on without you and will still be there when you return. It’s harsh but true.

But as an entrepreneur, taking days off matters more, both for better and worse.

Any day that you’re not working on your product or business is a day of progress and potentially revenue lost. For each day that you take off, your competitors may be moving ahead of you, and it’s a day where you’re just not learning anything.

But if you don’t take time off, you won’t be able to recharge and your mind will never be 100%. You likely won’t be able to make those creative breakthroughs that are so important to the success of a company. You’ll get burned out.

Quite a predicament, huh?

Personally, I’ve been feeling a lot of guilt lately. I keep thinking that I don’t do enough for my day job, I don’t do enough for WinOptix, and I don’t do enough as a parent and husband. I don’t know how much of that is true or if it’s just me.

One possible answer is that I can work harder. Dedicate more hours to my day job, stay up later to work on WinOptix, and spend more time with my family.

You can see just how impossible that is.

Hopefully it’s just all in my head. And I think some time away will help clear my mind and be more comfortable with my situation. It has to be real time away though, where I’m truly physically and mentally disconnected from work. Otherwise, it’s not really time away.

On that note, I’ll be traveling to Thailand for the next couple of weeks to attend my cousin’s wedding, hang out with some elephants and tigers, see some temples, and eat some amazing Thai food. I’ll see family that I haven’t seen in a long time, and spend time with my family exploring very different environments.

I’m going to take this time to reflect on my current situation, think about the path forward, and reset my mind. So I won’t be blogging over the next three Fridays. Hopefully I’ll come back refreshed, less guilt-ridden, and ready to kick some ass.

See you in a few weeks. And remember, go take a day or two off from work and don’t feel guilty about it. It’ll help in the long run.

Doing things you don’t have to do

Some of the biggest breakthroughs have come from people doing things that they didn’t have to do.

Though it’s largely gone now, Google didn’t have to implement their famous 20% time program, where their employees could spend 20% of their hours working on side projects that might help the company. And their engineers didn’t have to work on these side projects if they didn’t want to. But Google and its employees did things they didn’t have to do, which led to amazing products such as Gmail, Google News, AdSense, and more.

Famed investor Marc Andreessen asks himself, “What do the nerds do on nights and weekends?” when searching for new investment opportunities. The side projects of these nerds may eventually lead to something that changes the world.

Gary Vaynerchuk doesn’t have to create that 500th Instagram post or that 1000th video. But he wants to buy the New York Jets, so he continues to crank out content.

Everyone needs to work to make money, put food on the table, and live life. But when you do things you don’t have to do, whether it’s within your company or on the side, that’s when special things can happen.

Maybe you have some ideas of how to improve how your company hires, but you work in Manufacturing and have little to no contact with HR. So what? Ask your boss and a HR rep to see if you can take on a side project that helps your company improve its hiring processes. That could lead to your company getting better at recruiting and retaining the best employees, and becoming an industry leader.

Or maybe you’re in Accounting and do a lot of repetitive things at your job. You can learn some programming on the side to automate some of your tedious tasks and become more efficient. This can lead to promotions and even a career change.

Start a blog or podcast about something you’re interested in. That could eventually turn into a money maker down the road.

If you have an interest, just explore it. Start learning. Do things that you don’t have to do, do them consistently, and don’t be afraid to learn and fail. Amazing things can happen.

How credible do you need to be to create content?

Back in the day, the only way to gain credibility in your career was to go to a top-tier college, work for some brand-name, behemoth organization, climb the corporate ladder, and obtain some powerful title like “VP of Corporate Development” or “Senior Managing General Partner.”

Now, with LinkedIn, YouTube, Twitter, Medium, and other blogging and social platforms, you can build your credibility without going the corporate route.

Look at Gary Vaynerchuk.

He was just a kid helping his parents run their local NJ wine store. No one knew who he was, and he certainly was not known as a wine expert like Robert Parker.

But he tasted thousands of wines and posted over 1000 video reviews on Wine Library TV. This helped transform him into a wine expert and grow the wine store into a $60 million business.

And now Gary is a living legend in the business world.

Every now and again, I have conversations with people who have thoughts about starting a blog or a podcast. All of them always ask the question, “what the hell should I write about? I don’t have real credibility in anything, so no one is going to read.”

My first answer is that everyone has some credibility in something.

You’ve been doing a job for X years, write about your work. Do you have a hobby that you enjoy and are good at? Write about that.

And to tell you the truth, even if you had a high level of credibility on a subject, that doesn’t necessarily lead to an audience. You still have to work hard at creating great content and distributing it consistently.

My second response is that even if you don’t have credibility, but are interested in a specific topic, just start chronicling your learning process.

The more your write (or record, or however you choose to deliver your message), the faster you’ll learn, the more credibility you’ll gain, and the more inspired you’ll be to keep learning.

You’ll connect with fellow learners and that’s when magic can happen. If you can connect with and help just one person out there, it’s totally worth it.

Everyone has “impostor syndrome” at some point. If you keep learning, you’ll get past the impostor stage are obtain that credibility. Yeah, there are some real impostors who claim to be credible but really aren’t. Avoid those people like the plague and don’t be one of them.

So it doesn’t really matter whether you’re credible or not. Get your thoughts and knowledge out there, and the world will be a better place for it.

Are MBAs good fits for startups?

There’s an ongoing debate about whether MBAs are good fits for startups.

Recently, Michael Seibel of Y Combinator tweeted this MBA-damning quote:

This led to an interview with Jeff Bussgang, Harvard Business School Professor and General Partner at Flybridge Capital Partners, about the impact of an MBA education on startup founders.

Famed entrepreneur and VC Guy Kawasaki said that MBAs are worth about a negative $250,000 to the valuation of a startup. And Guy has an MBA!

As a startup founder with an MBA, I have some opinions about this. But take this with a grain of salt, because I haven’t done shit in the startup world (yet). 🙂

With anything, there are pros and cons, and having an MBA in a startup is no different.

MBA good fit for startups

Pros of MBAs in Startups

Generalist Skill Set

I believe the skill set of an MBA fits well with what’s needed at an early stage startup.

Regardless of what specialization was chosen by the student, MBAs receive a degree in general management. Thus, they have knowledge about multiple aspects of business, including marketing, finance, accounting, strategy, and many other subjects.

I believe this fits well with what a startup needs in its early stages – a generalist who can address many parts of the business. And if that MBA has deeper expertise in marketing and growth, the candidate is even a better fit.

Yes, engineers are the most valuable members of an early-stage startup team, because they can actually build the product and get it to market. But having that marketer or business person to do everything that the engineers can’t or don’t want to do is very important as well.

Additionally, many MBAs are numbers-oriented and fluent in analytics, which is necessary to validate assumptions, measure product usage, and assess other trends.

MBAs can help the engineers concentrate on what they do best – developing the product – and add value in many other ways.

Ability to Learn

All MBAs from top-tier schools have at least a few years of work experience before heading back to get their advanced degree, so they have proven their ability to adapt to different industries and work environments.

This ability to learn and adapt is critical to startups. Steve Blank and Eric Ries preach about customer development and the Lean Startup, both of which focus on continuous, iterative learning.

MBAs have proven the ability to learn throughout their careers, whether it’s on the job or in the classroom. So why would anyone doubt that they could do the same in a startup environment?

The Network

One of the most valuable benefits of going to B-school is the network that you gain access to.

My alma mater, NYU Stern, has over 100,000 alumni in over 125 countries across the globe.

MBAs can leverage these massive networks to raise money, find great partners, and potentially help get a startup acquired (if it makes it that far).

Businesses are built on relationships, and business schools can help forge these very valuable relationships.

Cons of MBAs in Startups

MBAs Want More Money and Less Risk

Most MBA candidates went to business school to make more money. Post-MBA salaries are often in the six figures, and candidates can double or triple their pre-MBA income.

And having an MBA decreases the level of risk for the future, since it’s a very marketable degree to have if you’re searching for a job.

This does not jive in the startup world.

Startups are fraught with risk. Depending on the stats that you believe, up to 90% of startups fail, many times because they run out of money.

And because of this, early-stage startup salaries are very low and even sometimes $0.

It’s obvious that this doesn’t align well with the typical MBA’s mindset.


MBAs are good at analysis, which can be a strength and a weakness.

The ability to process and analyze data is helpful for any type and stage of company. But over-analysis is a bad thing for startups.

Speed is one of the few advantages startups have over their incumbent competition, and many times quick decisions need to be made with incomplete information. MBAs tend to want to collect more data, do more surveys, and just pore over the data until a solid conclusion can be obtained.

Early-stage startups just don’t work this way.

Managing vs. Making

MBAs typically have a few years of work experience under their belts, and many of them have moved up from some lower-level analyst position to a manager role.

Once you become a manager, going back to actually doing the work can be extremely difficult.

After years of hiring people to write blog posts, would you want to do it yourself?

Do you even remember how to build that revenue model that your analysts have been creating for you when you were working at that investment bank?

YC co-founder Paul Graham wrote the seminal article about the maker’s vs. manager’s schedule.

Early-stage startups need makers, not managers. And unfortunately it’s very difficult to revert back to being a do-er after managing people for a while.


Michael Siebel and Guy Kawasaki obviously have their negative opinions. But there is a good amount of evidence that MBAs are good startup founders.

David Fairbank, formerly of NextView Ventures, wrote a great piece on how MBAs have been successful founders.

Entrepreneur-turned-academic Vivek Wadhwa said that his MBA from NYU Stern (yes!) was the best investment he’s ever made.

And Poets and Quants has plenty of articles about the success of MBA startups, like this one.

So what’s the verdict? Is the MBA good for startups?

Like many arguments, it depends.

Personally, I think an MBA brings a lot of good things to the startup table, but the founder needs to be really open to learning, doing things differently, and sacrificing lots of money and stability.

Is an MBA a pre-requisite to startup success? Definitely not.

But are MBA founders doomed for failure? Definitely not, too.

What are your thoughts about MBAs in startups? I’d love to hear from you.

Let Your Personality Shine in Your Product

A couple of years ago, the folks at startup accelerator Y Combinator put on a series of lectures called “How to Start a Startup” at Stanford University.

My favorite lecture was lecture 7, “How to Build Products Users Love“, which was presented by Kevin Hale, Founder of online form company Wufoo and now Partner at YC.

There is a TON of great information about user onboarding, customer support, and much more.

But the enduring theme that I took out of the lecture was how to incorporate your personality into your product to make it something that your users love to use.

With Wufoo, they did things like include interesting microcopy, like having “RARRR!” pop up when you hover over the dinosaur login button:


Wufoo login microcopy



Another example was from one of Wufoo’s customers who included some hilarious microcopy in their sign-up form:

Corkd form microcopy


Every time you open Slack, they’ll have an amusing message waiting for you to start your day:

Slack quote


Of course, you need to build a product that provides value to the user, is fast, doesn’t crash all the time, has solid design, and has all of the other baseline things that a good product should have.

But these little user experience details count a lot, and incorporating your personality into your product wherever possible can delight users and keep them coming back. It can build trust, put a smile on users’ faces, and make them feel loved.

While product designs will differ, many products that do similar things tend to feel the same. There are many online form tools like Wufoo that get the job done. But the microcopy and other details that reflect the company’s personality can be the difference in winning or losing that customer.

Have you encountered a product where you saw the company’s personality shine through? I’d love to hear your thoughts!

Targeting a Niche Audience Early – Lessons Learned from Past Startups Part 5

This is the fifth post I’ve written about some of the mistakes I’ve made with past startups. You can find the other four here:

  1. Alignment with Idea – Lessons Learned from Past Startups 
  2. Alignment with Co-Founders – Lessons Learned From Past Startups Pt. 2
  3. Real Customer Development – Lessons Learned from Past Startups Pt. 3
  4. Testing Mockups Before Coding – Lessons Learned from Past Startups Pt. 4

Hi! Sorry, I didn’t blog last week off because I was traveling for a wedding. Did you miss me?

Anyway, today I’m going to write about a big mistake I’ve made in my past startups – not focusing on a niche audience in the early days.

target niche audience

Dokkit – a calendar tool for everyone

We didn’t get very far with Dokkit because of team issues, so not selecting a niche audience didn’t really bite us. But the path we were going down was for a very generic audience, so it would eventually have caused problems.

The plan was to ingest a whole bunch of different types of calendars – the schedules of sports teams, concert halls, bars, restaurants, you name it – for anyone to download.

Thus, we were going to try to make everyone happy, and probably would have made no one happy.

The smart thing to do would have been to focus on one type of calendar – sports teams’ schedules, for instance – and reach out only to sports fans to see if Dokkit would add value to their lives. If so, great; we could continue to build out additional functionality for sports fans. If not, we could have either stuck with sports fans to try to solve other calendar or scheduling problems, or move on to another audience.

We didn’t even get to run into the audience problem, but we would have eventually.

ribl – a conscious (and wrong) decision to stay broad

We had a choice with ribl – to launch it into the wild and see who would use it and for what purposes, or to focus on a niche audience and iterate through different types of users if things didn’t seem to be working.

We chose the former, and received feedback like “I don’t know what to post,” and “This seems cool but I’m not sure what to use it for.”

It’s tough to grow an audience who doesn’t know what your app is supposed to do. And to tell you the truth, we didn’t really do much about changing that.

What we should have done is pick one audience – maybe concert attendees – and focus on how they shared their experiences at concerts and events. If that didn’t work, we could have moved on to restaurant goers, or sports fans, or another niche local audience.

We also had a choice to focus on a specific geographic area. While we did concentrate our efforts on the DC / Baltimore area, we didn’t solely focus on it. We actually had users all over the world – from San Francisco to Brazil to China – but that was actually a bad thing, as ribl needed a certain density of users around a specific location to have value.

Heck, we launched ribl at South By Southwest, and I spent thousands of dollars and sweated my ass off in a frog suit. It was fun but completely draining, and eventually worthless.

mike in frog costume

This frog was not that happy at the end of SXSW.

Facebook started with Harvard only. Foursquare focused on NYC. ConvertKit focused on a specific type of blogger (see the “Working in Niches” section of this blog post from Groove.)

Focusing on a niche audience in the early days in crucial.

Applying this to WinOptix

From my customer development interviews, I’ve narrowed down the initial audience for WinOptix to professional services federal government contracting companies with at least $3M in revenue. Pretty focused and descriptive, huh?

While I’ve spoken to very large contractors like Booz Allen Hamilton and Raytheon, and much smaller govcons that you’ve never heard of, these conversations have helped me eliminate these types of companies from my target segment.

And while WinOptix certainly has applications for state and local government contractors, ad agencies, and anyone who responds to RFPs, I’m not going to worry about those segments now.

Focusing on my initial target audience will allow me truly understand their needs and build a product that solves their problems. I know we may still be wrong along the way, we’ll be in a better position to adjust accordingly with a smaller, niche audience.


Starting with a small target audience is so important.

You can deeply understand their needs and solve their problems. If what you build isn’t working, you can either solve a different problem or move on to another audience who might have similar problems.

But if you try to solve everyone’s problems, you’ll solve nobody’s.

What are your thoughts about targeting a niche audience in the early stages of your startup? I’d love to hear your thoughts in the comments.