Archives for November 2015

November 18, 2015 - No Comments!

How To Innovate: The Dummy’s Guide

Pitch after pitch, it’s clear a lot of people get this wrong from the start. We take a hard stance on our process for coming up with new products, ideas, features, or services — essentially, how we innovate. The human element of innovation is too often lost.

First and foremost, we talk to people about their problems.
I enjoy talking to people about their problems. Very often, I like to ask these three questions:

  1. What is your biggest problem? Why?
  2. What is your biggest time drain? Why?
  3. What is unnecessarily expensive? Why?

We don’t go in swinging with ideas, solutions, and a pitch; we go in swinging with questions. We seek to understand people deeply, understand their problems and their motivations. We ask “why?” a lot.

The myth of the lonely visionary
There’s this idea that the lone genius in a sterile room will, by just sitting there and thinking for long enough, happen upon the brilliant idea of a lifetime. And that’s the process that most pitches I hear went through. They are entirely disconnected from real problems.

This lonely visionary concept is a myth. You have to understand people and their problems to be able to create a valuable solution for them.

Henry Ford’s ill-cited quote
A famous Henry Ford quote:

If I had asked people what they wanted, they would have said faster horses.

I love this quote. But many think it proves the lonely visionary — Henry didn’t talk to people, so why should I?

Here, however, Henry should have asked a simple question: “why?” For example:


Here’s the difference: Henry already knew the problem. His quote is not a license to take people out of the equation. It’s proof that you need to know the problem, not the request.

Find the fundamental, underlying problem
Understanding the fundamental, underlying problem is the key to building the right thing. How? Use the 5 Whys.

There’s an urban legend, probably untrue, that goes like this:

A proposal was submitted to move the city airport to a new location. It would cost $500 million. While reviewing the proposal, someone asked,
“Why does the airport need to be moved?”

“Because its current location has a huge bird population that is becoming a serious risk to the increasing traffic of airplanes taking off.”

“Why are there so many birds?”

Unsure of the answer, the team looked into it. After some time, they discovered the answer. “Because there is a large population of spiders in the area that the birds eat.”


After looking into it again, “because there is a large population of large insects at dusk that the spiders eat.”

“Because the bright lights on the local monuments attract them at dusk.”

“Why are the lights so bright?”

“So people can see the monuments. Though they don’t need to be so bright.”

Knowing this, the team first tried dimming the lights to 50% brightness, and ultimately the problem went away. Instead of spending $500 million, they actually ended up saving a few bucks each year.

Using the 5 whys helps you to get down to the fundamental, underlying problem. Solve that problem.

Good product design starts with empathy.

Then, start to solve the problem.
Once you have a problem that resonates, then attempt to solve it. This is the step that takes creativity, imagination, research, thinking alone, thinking out loud, and brainstorming.

Propose solutions to people, and find one that resonates.

Iterate and refine.
As you propose solutions, write down all of the questions people ask. Make those pieces clearer for the next person you share the solution with. Their qualitative remarks can be invaluable.

With their feedback, you can iterate not just the concept, but also the language that surrounds it. For example, when I was first telling people about the idea that would eventually become Mail Pilot, I suggested a feature I called “review by date” where an email that you don’t need to deal with until friday could be marked for review on Friday, leaving the inbox until then, and popping back up at the time it was needed. People loved the idea, but it took a little bit of time for people to get it. One person said, “Oh, like a reminder!” To which I thought, “duh, yes, that’s a way better name.” For everyone else, I called it a reminder and it clicked instantly.

Share, listen, iterate, repeat.

I’ve said it before, but it’s worth saying again: iteration is key. Execution trumps ideas. Iterating with feedback is how to nail the execution.

Connect your ideas with reality.
With both Mail Pilot and Throttle, we were coming up with ideas that aren’t supported by today’s protocols. The last step is to figure out how to get reminders to work in today’s IMAP protocol or how to detect someone sold your email address with today’s SMTP protocol.

Without connecting our ideas to the reality of today’s context, today’s technology, we’d ship software entirely useless for people’s current setups, and our software could die before ever being adopted. Even Google couldn’t pull that off, sadly.

This quote is the cornerstone of our existence:

Start where you are. Use what you have. Do what you can.

Consider what would kill your product.
Every month, we like to ask ourselves, “What would kill Mail Pilot?” Or better yet, “What would kill email?”

We’ve had a few answers, and those answers are slowly becoming products and features. While yes, that means some of our products will cannibalize our existing top-sellers, if we don’t, someone else will.

It’s dead simple. There are three simple steps to take when trying to ideate a product to bring to market.

  1. Find a problem that resonates with people
  2. Find a solution to that problem that resonates with people
  3. Connect your ideas to reality

If you leave this post with one thought, let it be this: don’t forget the human element of innovation.

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November 17, 2015 - No Comments!

Behind the Mail Pilot Branding

maritime pilot helps ship captains maneuver through difficult or congested waters. Mail Pilot helps you maneuver through the difficult and congested waters of your inbox.

As a captain, when you need a maritime pilot on board, you raise a “Signal G” flag. Once the pilot is on board, you raise a “Signal H” flag, which is half red, half white.

And so you have the Mail Pilot branding, red sails on a white field.


We didn’t originally create the Mail Pilot brand with this metaphor; we applied it later.

Initially, I was word mapping, and went down this path: “Burn down your inbox” > “burn” > “fire” > “light”> “pilot light” > “pilot” > “copilot” > “aviator”. Initially, I used “Aviator” as the name. After a while, I used “Copilot Mail” but eventually landed on “Mail Pilot” which really seemed to stick.


After our Kickstarter, we wanted to appeal to the productivity-ists and early adopters in tech. We thought the imagery of space exploration would evoke that sense, so the first icon was an astronaut’s pin.


After a fantastic public launch, we got a call from Apple, who worked with us quite a bit more than we expected. Wondering if the impending iOS launch would be featured, we contemplated the need for Mail Pilot’s branding to appeal to a wider audience. When I was sketching a few random new directions out, the sails formed, and I really liked them; they’re more approachable, simpler, and evoke a sense of calm. It also, coincidentally, had a stronger metaphor to the name.

With that new metaphor, we got to leverage new nautical themes, like “#SetSail” on Twitter, and “Anchors Aweigh” on the launch button in the app’s onboarding. Finally, we’ve also put together thematic posters for the office.

Screen Shot 2016-07-06 at 9.25.33 PM

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November 12, 2015 - No Comments!

When “Someone’s Already Done It”

You come up with a brilliant idea, you obsess over it, you Google some info, and on your screen lies your idea, being done by someone else, for the last two years. You’re all too familiar with that sinking feeling in your stomache that follows. You adandon the idea almost immedaitely after all that excitement and ideation.

Two things. First, existing solutions prove your idea — their existence proves that you’re trying to solve a real problem that people might pay to have solved. And it proves that you’re heading in a direction that makes sense in the market.

Second, and this is the biggie: The moment you see someone else’s solution, you mar and limit your ideas. It suddenly becomes a lot more difficult to think outside the box because before, you were exploring totally new territory, but now, you’ve seen someone else’s path. It becomes much harder to be freely creative.

Next time you come up with that great idea, don’t Google it for a week. Let your mind fester on the idea, allow it to grow like many branches from a trunk. Jot down all of the tangentially realted but equally exciting ideas that inevitably follow. Allow your mind to take the idea far into new places. No, you won’t build 90% of them, but give yourself the time to enjoy exploring the idea totally.

When I do this, once I do Google for existing solutions, I usually find that all the other things I came up with are far better than the existing solutions — I have more innovative ideas for where it could go next; I have a unique value proposition that the other guys haven’t figured out yet. But had I searched for them first, I never would have come up with those better ideas.

Finally, if you see your idea has already been done and no longer care about it, then it wasn’t something you were passionate enough about in the first place. Consider it a blessing that you found it.

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November 11, 2015 - No Comments!

Three Qualities of Entrepreneurs That Aren’t Clichés

Regularly, students ask me about what qualities make good entrepreneurs. There are too many cliché answers I could give, so over time, I’ve built up my own list of three that aren’t cliches:


When I looked at my designs for an ‘email client of the future’ I wanted it immediately. I didn’t want to wait for someone else to figure it out, my impatience was such a huge motivator that it pushed me to sit down and make it happen as soon as I could.


Without naivety, it’s painfully clear just how much work, energy, and time it takes to start a business, or build an entire line of email clients from scratch. So I think naivety really helped me: I was able to jump right in without reservation.


When it comes to designing products that are successful at fitting right into place in a person’s life, workday, or environment, it starts with empathy. You have to be able to get into the mind of your potential customer and figure out their language, motivations, goals, working styles, etc.

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November 10, 2015 - No Comments!

The Human Element of Great Leadership

The Difference Between Good vs. Great Leaders

I’ve been asked a few times recently to give advice to leaders. I have usually responded by saying that I don’t have enough perspective or experience to have distilled any universal truths that would be credible advice that I think someone else should take. That said, the question keeps coming up, and there are probably a few words I can string together on the topic.

What I can share are lessons I’ve learned for myself. I’m not suggesting anyone take these lessons as advice for themselves, but these experiences that I’ll share may help direct your own thoughts in the future. Here it goes.

Have no ego

To be a great leader, I have found that you must have no ego whatsoever. Leaders with egos need to feel more important, smarter, needed. This is toxic for a few reasons:

  1. Leaders with egos hire people that aren’t as good as they are. The entire team underperforms because their leaders cobbled together the wrong team. This is where the saying “A players hire A players; B players hire C players” comes from.
  2. Leaders with egos ensure that people need them. For example, they might hand over most of the reigns, but keep an important step for themselves, so people have to keep coming back to them. Why is this so bad? Well, a team that would crumble without any one single member is a team hobbling on one leg.
  3. Leaders with egos don’t allow a winning ideology to permeate the team, so their team lacks a basic cohesion, depth, and alignment. Instead, people work “for” him. These leaders prefer to be the charismatic, well-known, potentially genius face of the team instead of supporting and resourcing their team members with a unifying purpose and method for success. This means they aren’t succession planning — so when they go, any performance the team was able to achieve before won’t last very long.

Lead from behind

Don’t manage people. If someone can’t manage themselves, they probably don’t belong on our small, high-passion, high-energy team. Making more rules tethering people to their desk at specific hours of the day, telling them how many days they are allowed to not be at the office per year, and telling people exactly how to do their job are all ways of managing people. People that should already know how to handle all of those things (time management, how to do their job, etc.) on their own.

Rather than leading from above, I ought to lead them from behind; instilling in them our core identity as a team, and our envisioned future, and supporting them as they carry our flag forward in the direction we all see fit. We first huddle; aligning onto a common purpose and goal, then the entire team works together to get us there.

Motivate with Purpose and Goals

In my experience, it’s much more effective to motivate not with carrots and sticks (rewards and punishments, see Drive), but rather with a meaningful purpose and audacious goals.

If I told you, “we’re going to build this thing over the next year, and if it succeeds, I’ll give you a 5% bonus, but if we start to slip, we’ll lose vacation days” how would you react? Would it motivate you? How much?

If I told you, “we believe that people should get to control who can send them email. We believe that people shouldn’t have to waste so much time in their inbox with pedantic tasks. We believe that we can improve people’s lives by freeing up their time for more important things — meaningful work, time with their family, etc. Because of this, we’re going to topple the biggest incumbent in the email industry with the innovation that we’re pulling together over this next year.” How would you react? Would it motivate you? How much?

My role as a leader is not to light a fire under people. My role is to light a fire in people — to paint a picture of the future, and fight like hell alongside my team members to get us there.

Fight alongside your team

I think many poor leaders think of themselves as head coach, when they should think of themselves as team captain.

A friend of mine, a CEO at a young company, went through tough times and a few team members left the team. Instead of demanding the other team members work more until replacements could be found, this CEO hopped right into the assembly line alongside the rest of the team and help get the products out the door on time. This CEO, along with ever member of their team, understands their common purpose and their common goal, and they’re working together to make it happen, regardless of the circumstances.

Motivation and Fulfillment

By doing all of these things, we’ve found that we can foster an environment that motivates people to get up in the morning to come to work, and leaves people feeling fulfilled at the end of the day.

Our lead developer at Mindsense, Jeb, put it this way:

The environment we’ve created at Mindsense where I can use exciting technology to build useful software for other people makes me look forward to coming into work everyday… I had always felt like I was a part of something bigger that just a 9–5 job.

Notice he said “the environment we’ve created” — it’s something that he has a sense of ownership over; his input matters, and he can help mold Mindsense into the company that he, along with the rest of his ream members, feels should exist in the world. This level of personal buy-in is incredibly fulfilling.

He also said “for other people” which has strong ties to our purpose. You can immediately see the effect that has in his last sentence, “I was a part of something bigger that just a 9–5 job.”

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November 6, 2015 - No Comments!

What Attracted Me to Software Design

As a kid, I became obsessed with this idea that the world is not simply as you receive it, but that it can be what you make it. That what is shown to me as “official” was designed by people just like me. And that I could take something that I thought could be designed better; something that could function better, or be clearer, and I could build that better, clearer thing, and then give that to the world. And software is the most inexpensive way to do this: I could come up with a better solution and build it in a day or a few days, and then have it to use.

A perfect example of this is Hungry Hokie. When I started at Virginia Tech, I loved the dining halls, but couldn’t keep track of the seemingly random hours for all 16 or so halls, particularly at nights, or on weekends and breaks. The hours calendar online was atrocious — requiring north of 40 clicks just to find out what dining centers were open at any given moment (serious).

I think that’s 45 clicks. I know what you’re thinking, “just use the left and right arrows, Alex!” You would think that. But those go forward and back by days on the same dining hall. When would you ever need that?

I think that’s 45 clicks. I know what you’re thinking, “just use the left and right arrows, Alex!” You would think that. But those go forward and back by days on the same dining hall. When would you ever need that?

I figured there should be an app that showed just the dining halls that are open right now. I built exactly that in two days, and it went on to be used thousands of times a day, and even got coverage from the New York Timesand the Washington Post — for some little app! But its impact was big: It was a better tool to allow us to live our lives more easily.



I’m obsessed with improving things and solving problems. Software is the most maximized path to do that: it’s the least expensive on resources of time and money, and its impact can be multipled nearly infinitely — any one action can provide a huge result.

Learn to make world-class products that sell themselves.

Get actionable insights on product design and product ideation each Thursday morning, so you can become a pro at creating products people will love.

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