Sales Principle 6: Timing is Critical


Timing is crucial to sales and the hardest to master. Timing is what sets Sales apart from just about everyone else at the company.

If you don’t think so, look at the history of great ideas introduced at the wrong time. There is a list of companies in the vast internet graveyard. Even big companies miss the boat such as Microsoft giving Android the phone market. One of Bill Gates’ biggest regrets.

In Sales, deals are no different just on a smaller scale. Every deal has a window of opportunity. 

Regardless of how much a slam dunk you think the sale might be, you have a finite amount of time to close.

Juggling multiple deals while deadlines approaching is challenging. Sales aren’t just about fancy dinners and looking like you’re having fun. Everything is dependent on a monthly, quarterly, or yearly timeline: rain or shine.

The art lies in picking up the cues as you navigate the jungle to lead you to the promised land.

I was thinking about a few tips, but there is just one question which helps me understand the dynamics of a deal.

When do you expect to start?

‍A terrible move any salesperson can make is to be too sleazy and pushy. I once asked a client, “So when are we closing this thing”? As you can imagine, it went over well.

However, asking about the start date is a more subtle way of figuring out the timeframe.

There are other ways to ask this same question, but this one is my go-to. 

The significant part of understanding the start date is it allows me to work backward. If I know the start date, then what does it take to get there knowing we are four weeks away? How long does it take to sign agreements? Is there a budget in place? Who else needs to be involved?

These questions and many more can be asked after the first question. It gives you the best sense of whether a deal is in urgent mode and the steps needed to meet the start date.

Understanding timing is also beneficial for the client. It isn’t a one-way street. You don’t want a salesperson breathing down your neck for a project that won’t start for another six months.

What sets the star players apart are they understanding timing better than anyone else. It may look like luck. It is seizing the opportunity.

Sales Principle 5: Build a Repeatable System


For some waking up early and working out feels right. For others maybe it is a midday stroll around the neighborhood.  

Everyone has a preference. There is no right or wrong answer. 

The main point is to have a strong  foundation of how your day will be structured.  Build a system that works for you and only you.  

A repeatable system sets you up for a good day. It helps to reduce the number of decisions we need to make in a day.  

For sales, building your own “system” is absolutely critical to be able to manage the daily grind which will take a toll if you don’t get organized. Building a system applies really to any role.  

Here are a few tips I have found to be useful, backed by sales science. The goal is to keep a simple system that allows you to hit it hard everyday.  

Schedule out time blocks  

  • Early Morning: I like to be early as most of our team is 3 hours ahead of me anyway. My first 1-2 hours before the kids are up are dedicated to writing, thinking, a little prep, and some light email/messages. I have found this routine to be quite powerful in getting me ready for the day. I’m not diving into any projects or heavy creative work.  

  • Mornings: Primarily for client and project related work. Following up with clients. Record an episode for the Thoughtful Software Podcast. Make calls. Creative work.  

  • Afternoons: I feel it is best to have meetings in the afternoons. There happens to be quite a bit of research supporting meetings later in the day. I’ll schedule my 1:1’s, company meetings, project updates, all if possible, in the afternoon. Creating proposals is also good afternoon work.

There are always exceptions to the rule, but I have found a simple daily structure of breaking my day up into time blocks is advantageous.  

Breaking up my day is also helpful to tackle the most challenging part of sales: getting prospects to call/email you back.  

It is not mentally possible to stay in prospect mode all day long. Time blocks allow me to switch things up throughout the day.  

Sales Cadence 

Now that I have my daily routine mostly figured out, time to get into the details. Studies show prospects need multiple touch points to decide to do anything. Most salespeople give up after only 1-2 attempts.  

An easy tip to increases sales without spending a dime on any tools is to increase your activity. The challenge is how do you increase activity without losing your mind. 

I fall back to a simple system. Email, email, call, email, email, call… 

A good CRM should help you manage the activity or using an email sequencing tool is helpful.  

Ultimately, stay focused during the morning session and work on prospecting daily.  


The most fun part about sales is working with people.  

Our mission at Skiplist is to not only help people understand hard technology, but to build it. It is gratifying for everyone at Skiplist to help people be better at what they do.  

It is then absolutely critical to make time to meet with clients and partners routinely.  

I had a sales manager back in the day who used to tell the sales team, “If I wanted you in the office, I would hire better-looking people.” Haha.  

But he had a point. Meet people and see what is happening out on the front lines. There is no substitute for meeting face to face. Even video calls can’t compare.  

Use your lunchtime and afternoons for meetings. Coffee meetings are great. Thirty-minute face to face meetings are fantastic. I did have to switch to decaf as I was getting addicted to caffeine.  

Whatever you do meet with people routinely, Use the mornings to spend time setting up those meetings systematically.  

Systems Produce Results 

As James Clear put it in Atomic Habits, “If you’re having trouble changing your habits, the problem isn’t you. The problem is your system.”  

Focusing on implementing a healthy repeatable system rather than specific outcomes leads to a more manageable balance of getting things done and enjoying your work.  

If we are ever to achieve our vision of making the world a better place through "Thoughtful Software" and with thoughtful people, it will be built on a foundation of excellent systems.  

Figure out the way that works for you and enjoy the rest. If you need help, contact us.

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Sales Principle 4: Dying, Lying, or Buying? Qualifying and Understanding Timing

Sales is a numbers game and a tough game. Most of the time we are getting told no or even worse getting nothing back. 

“Hello? Is it me you’re looking for?” Nope. 


Searching for potential customers is time-consuming. Painful. Heartbreaking. So, when you do get someone interested in having a discussion it is quite natural to be excited. It happens to even the most seasoned professionals. 

The challenge is how do we find out what is real and what isn’t?

Therein lies the art of qualifying a deal. I have to credit my old pal Will Harrison who gave me an easy and straightforward phrase to remember. Find out if a prospect is dying, lying, or buying? DLB for short.

It’s not as harsh as it sounds but an easy reminder it is ridiculously important to understand the overall status of a deal as soon as possible. I like to think about qualifying a deal in simple terms. 

Who is the coach, champion, decision maker, and buyer? Meddic sales methodology is a popular one. All essential questions but when dealing with dozens of deals going in and out of the pipeline, I always come back to DLB. It feels more organic and natural to my style as I am engaging in multiple daily conversations. 

I’ll share a few tips on how I try to understand what is real and what isn’t. By no means are these tips strict rules. Just some guidelines I use to help everyone involved. Including customers. 

The key though is always to be empathicauthentic, and conversational. Never be robotic and go through a list of set questions when qualifying a deal. Don’t be a jerk. 


Dying deals have all kinds of issues. No internal support. No real budget. No timing. Politics. 

Projects come and go for various reasons. Most if not all projects require some management buy-in and support. 

If your champion does not have internal support, your proposal will be dead on arrival. 

  • Who else needs to review the proposal?

  • How do you usually buy these types of services?

Meeting others involved will help understand the realness of a deal. You’ll also learn more about the dynamics with team members. 

  • Do you your homework also. Some industries such as the semiconductor industry are cyclical.

  • Are you catching them on a downturn? Budgets tighten up.

  • Is the specific company you are targeting dying?

  • Are they getting hammered by their competition?

  • Will your product or service move the needle?

Just a few questions to think about as you find an interesting potential deal. 


In my years in sales, the most challenging competitor I have ever faced and continue to meet is the biggest and baddest of them all. 

The dreaded “Do Nothing.” Three things usually happen in a deal. You win, you lose, or nothing happens. The customer decided to stay put and do nothing. 

In the do-nothing scenario, everyone loses. The first person who got out wins. Don’t be the person who after countless emails and meetings finds out the customer is not going to spend any money at all. Crushing. 

Or maybe they are going to push the project out to next year’s budget. Ugh! Those are the hardest ones to swallow and honestly the hardest part about sales. 

When you get knocked out with a gut punch. 

Often doing nothing isn’t anyone's fault — just the nature of the game. Shit happens. 

Without hesitation, pick yourself up and dust it off. Our ability to shake things off is also why salespeople make the big bucks. However, the mental anguish does take a toll and sales isn’t for everyone. 

Stay in close communication. Silence is death for a deal.

  • Confirm start dates. When would you like to start the project?

  • Has anything changed?

  • Get to know more people if possible

  • Build rapport. Relationships are critical.


“What is your budget”? 

One of my very first sales calls in what seems like ages ago, I decided to make asking about the budget the first thing that came out of my mouth. 

To the horror of my sales manager,  like a pro he laughed it off and kicked me under the table. I didn’t say a word afterward.

Although understanding the budget is essential, there is an art to navigating the money question.

I learned a valuable lesson. 

Usually, if the deal is active, you can feel it. There is activity. People are communicating. A solid timeline is understood. We have a budget. We have buy-in. We have a problem to solve. 

We can get into closing a deal. It helps to have a good sales process at this point and be able to walk a potential customer through the process. 

I admit I am not the best at following processes. I prefer a more freestyle approach. I prefer a more freestyle approach but I do have a process I tend to follow in my head. My advice is don’t do freestyle often.

Be disciplined in navigating a lead to close. At any point, buying can turn into lying or dying faster than you can say “Skiplist is awesome.”

There are many variables to consider when qualifying a deal. By being in the right mindset and disciplined you’ll find the early discussions more fruitful and more predictable. 

Make it rain!

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Sales Principle 3: Don’t Be a Jerk. Empathy is the Root of all Successful Conversations.


In 1998, according to the Associated Press, our average attention span was around 12 minutes. A decade later, attention spans dropped by 50% to 5-6 minutes. I’ll bet they are about five seconds today. 

There are many factors for the dramatic drop in these statistics. Social media is a huge culprit that has rewired our brains to make it more difficult to pay attention for long periods. 

If you have ever been part of a long sales presentation and wanted to fall asleep, please raise your hand. I’ll confess, in the past, I’ve wanted to fall asleep in long presentations my colleagues were giving. I also have done hour-long presentations and felt they were about 55 minutes too long. 

So many salespeople still want to set up that one-hour time slot to make a standard pitch using a standard deck. It is not only quite inefficient, but it’s also quite rude. 

The third sales principle is all about empathy. I was going to say “Be Empathic.” However, empathy seems too official of a word. It doesn’t hit on the point hard of don’t be a jerk. 

Align Priorities 

Our customers have many other things to do besides sit in hour-long presentations. They most likely have a difficult job filled with a busy array of tasks, projects, and meetings throughout the day. 

Our goal as salespeople and product builders are to help our customers be better at what they do. First, we must understand the challenges our customers face and position everything to accomplish our goal. 

Anything else is a waste of time. 

Aligning priorities is more about aligning our mindset. That email you just sent to a new prospect, is it all about your company and products or did you take a minute to learn more about the person you’re emailing?

The deck you just prepared is it just the standard pitch or did you thoughtfully prepare to touch on key points relevant to the client. 

The challenge salespeople have they are in a natural conflicted position. Earning the big commission check drives hyperactivity. To achieve the hyperactivity salespeople will rely on a cookie cutter system to contact as many clients as possible. 

It is a challenge I have faced throughout my career. Doing anything custom or personalized slows down my ability to reach as many prospects as possible. 

The reality I came to understand as I spent more time in the field is the standard approach to sales is pure laziness. 

Personalizing our interactions does require more work. However, the long terms gain to spend a few extra minutes in preparation greatly outweigh any short quick mass emails. 

There are a time and place for mass emails such as event notices and updates which isn’t in the scope of this discussion. 

Thoughtful Software Process

At Skiplist, we firmly believe in what we call “Thoughtful Software.” It is more than just building software a certain way, although we do that well, it is an empathic approach to every touch point we have with clients and our partners.

From idea to handoff. 

For example, we rarely if ever will stand up in a conference room and pitch what we do. We prefer and emphasize conversations above all. We don’t even have a presentation anyone at Skiplist can present for more than 15 minutes. Our focus is on the problem we are all trying to solve and not us. 

We make it a point to streamline the legal process to smoothly and quickly start projects. Has anyone figured out why it takes six months to sign a services agreement? 

New technologies such as machine learning and blockchain can lead you down a complicated path when sometimes a more straightforward solution may be available. It doesn’t always make sense to push new technology when it may actually overcomplicate matters.

We value simpler thoughtful interactions to help everyone involved achieve the bigger vision and solve problems efficiently. 

A few final thoughts: 

  • Have an open mindset

  • Adapt

  • It’s not all about the commission. See sales principles 1 and 2.

  • Keep your meetings shorts. 15 minutes or 30 minutes max

  • Focus on conversations

  • Be mindful of your client’s schedule

  • Listen, listen, listen.

You’ll find people will want to work with you more, and your interactions will be more fruitful.   It is a compounding effect that leads to consistent success. 

Oh ya, and don’t be an a$$hole either.

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Sales Principles 2: Be Authentic. Be Genuine.

When you first set your mindset to help your customers as I discussed in Sales Principle #1, then you are on a journey to immense success. To make the journey more enjoyable and sales less of a grind, I firmly believe being authentic and genuine are essential. 

If you are a complete bozo, I’m not sure what to tell you. Hopefully, this article can help. 


This is more about building real lasting relationships. None of that fake stuff. Keepin’ it real. 

At Skiplist, one of our core values is “Relationships over Money.” Easy to say but very hard to practice. 

Everyone at Skiplist profoundly believes in our core values. This is our differentiator and what makes working at Skiplist a blast. 

The Long Game

Salespeople are pulled in all kinds of directions. Hitting your yearly, monthly, or even weekly quota is difficult enough. How do you focus on relationships when your manager is breathing down on you to sell, sell, sell? Not easy. 

The top salespeople and great companies understand deals don’t happen overnight. They take time. Our job is to guide deals through the process which on average can take six months or more.

Don’t get me wrong, even though deals take a long time that doesn’t mean you sit around. I’ll talk about pipeline management in another principle. 

Throughout the length of a deal, you’ll want to be on constant communication. 

Good solid communication is not going to happen if you don’t have a good relationship with your customer and you won’t have a good relationship if you are not really authentic throughout the process. Customers can snuff out fake. They will be less forthcoming with crucial information. 

If you are not always focused on short term results and you genuinely care about your customer’s success. Everyone can feel it, and the oddest thing happens. Deals close smoother and become more predictable. 

A salespersons’ dream. 

Scaling Values

When Andrew and I were in New York recently, we spoke to Gary Vaynerchuck about scaling values in an organization. It was a fascinating discussion around how he leads by example. We could see and feel it with everyone we met in his office. 

Imagine how VaynerMedia then treats its customers. I’m sure it is an excellent experience from the salesperson all the way to Gary. 

There is no such thing as B2B really. It is all P2P or person to person. Authentic relationships matter. 

Fortunately, there is a ton of opportunity as most salespeople focus only on the transaction. 

As a final thought, I recommend never go through robotic scripts, don’t be transactional, be a giver not a taker, build a close network of people who love to help, and please never go through the motions. 

Instead, be present, be thoughtful, be authentic, be genuine, and always hustle.

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Sales Principle 1: Selling is Not Convincing. Selling is Helping

Check out my original post on why I decided to start writing about "Sales Principles."


I’ve heard many definitions of what is sales, but Mark Cuban put it best, “Selling is not convincing. Selling is helping.”

It is unfortunate that “sales” is often associated negatively. I’ll admit sales rightfully gets a bad rap, and there are many bad salespeople out there. We have all experienced a tricky or pushy salesperson. You feel horrible and used. 

Have you seen Broiler Room, Glengarry Glen Ross, Wolf of Wall Street and so on? Slick hair, thousand-dollar suit. Excuse me while I clutch my wallet.

These experiences lead people to be cautious when buying products. Understandable. 

Well, sales isn’t a bad word, and the great salespeople know how to help customers not convince them. 

Evolution of Sales

Sales have changed quite a bit in the last thirty years. Consumer consumption and demands have also dramatically become more complex.

It first started with feature selling. Present the customer with how fast your widget can do something. Remember the computer processor wars? 1.5GHz vs. 1.7GHz! I’m going with the faster processor. I need my browser to open a few milliseconds faster. 

Don’t get me wrong it is essential to discuss the specs. However, your product is more than just bits and bytes.

Feature selling is a losing strategy. The rapid pace of changing technology and the rush of new entrants will put you on constant shaky ground. 

Then came solution selling where the salesperson focuses on the customer problem and matches it to a product or solution. 

Theoretically, solution selling seems like a home run. However, in reality, the complexity of each situation does not allow for things to work out that easy. 

“Everyone has a game plan until they get hit in the mouth.” – Mike Tyson 

Rarely in my career have I ever walked into a sales pitch where the stars aligned and I walked out with a signed deal. The one to one match of a problem to a solution doesn’t exist, especially in custom software development services. 

The other challenge is solution selling doesn’t take into account the personal human aspect of buying and selling. You’ll need to get the customer to offer up what problems they are facing. What if they don’t want to tell you about their problems or don’t know exactly themselves? 

Also, buyers are coming in well prepared and better educated. Open-ended questions to learn more are hard to get answered. You can’t just fit your solution in nicely to a specific problem. 

Buyers are dealing with more complex problems than ever before. 

Then why do so many salespeople beat this to death? I don’t know. Laziness, ignorance, greed…?

Today, there is a shift to focus more on insight selling. This type of selling focuses on helping customers work through challenging problems together. 

Insightful salespeople:

•    Actively listen

•    Ask the right questions

•    Bring ideas

•    Collaborate

•    Roll up their sleeves to help come up with answers 

We are in the idea economy. Bring ideas. Be a helper, not a seller, and your customers will come back to you again and again. 

One Size Does Not Fit All

Features, solutions, and insights. What is a salesperson to do now? 

The answer is all of the above.  

It is imperative salespeople today possess the ability to navigate deals with every possible tool to help customers achieve their goals. 

This complexity makes selling extremely hard. Rapid changing technology means you always have to stay up to date. Continuous learning is a vital part of sales. 

Not to mention salespeople today must possess a high emotional intelligence (EQ). 

At Skiplist, we don’t look to push machine learning for example, on a project just because we do those projects well. 

We look for areas where we can provide the most value as it relates to the bigger picture. 

Do we need an ideation session first to flush out the goals of a project? Maybe we can stand-up a basic architecture quickly to start testing our assumptions before moving to the next phase. Is there something off the shelf that can help us during this one phase? 

Our Innovators Toolkit is often helpful to think about those early questions. 

I recommend rather than getting lost in a specific sales methodology or try to do everything at once. 

Focus on one thing.

How can you help your customers be better at what they do?  

Help don’t convince.

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Our Journey and Our Values


My journey at Skiplist has been nothing but exciting. Over the last year, we have grown tremendously with each person bringing a diverse background to the table. Never a dull moment at Skiplist that is for sure. 

From starting our podcast to meeting Gary Vaynerchuk, the opportunity to work with some of the brightest minds is genuinely humbling. 

Our clients and partners are the best and believe as we do, thoughtful software and thoughtful people can change the world for the better. 

Our mission has and will always be to transform the software industry with incredible and thoughtful software. 

For me, leading our sales, marketing, and product efforts, I keep pondering one question.

“What do we want people to remember about us?”  

To formulate the strategy of Skiplist and our various teams, it is critical we root our decisions with strong values and principles. 

There is already enough nonsense out there. We don't need more.

I’m a huge fan of Ray Dalio and his book “Principles.” A truly transformative read. 

Inspired by Mr. Dalio, I figure there is no time better than now to share over the next few weeks my thoughts and principles on sales, marketing, and product. 

My primary goal is to share how we think about customer experiences and what we want people to remember about working with the great folks at Skiplist.  

I’ll start with my ten “Sales Principles.” I probably have a hundred but ten seems like a good start.

The Deep Life

We are visual creatures. Society places a tremendous amount of importance on what we see. The way we dress, our shape, and our color. It is so powerful in fact, billion dollar companies such as Instagram are all about visuals.

It is this urge to appeal to our visual senses where our reality gets distorted. We are able to filter the output and filter the input. Or that is what we are led to believe.

Tuesday afternoon around 2:15pm. Cranking away on a report due in a few hours. Ding. A notification pops up on your phone. A post from a former colleague from two jobs ago. Someone you have not spoken to since you stepped out of those office doors.

A picture from their family vacation. Cool.

Posting a picture of a fabulous vacation in the Bahamas sends a lasting ripple through our mental networks, causing more harm than good.

This is a shallow activity yet perceived to be important.

What we see fires off our neurons in our brain to feel the joy of the Bahamas. Often it turns into jealousy and anger.

“Why am I here working on this report when I could be in the Bahamas?”

Instead of focusing on the report, our mind is distracted. The attention economy is in full effect. You’re plugged in now. Get ready.

You’ll end up wasting a considerable amount of time on the Bahamas now. Also, trying to convince your wife the trip is a good idea.

I bring up this small scenario as recently I read “Deep Work” by Cal Newport. This is one of those books where when I was done, it changed my reality. I had been living in the matrix all along.

Seemingly, innocent notifications drain our mental capacity and set a chain reaction of shallow events. All to appease our urges.

The question then is does being connected all the time in real-time be a fruitful way to live? Newport argues it isn’t. I agree.

There are extreme measures some take by completing cutting themselves off. Digital detox I think its called. Abstain from technology for a period of time.

I’m not buying it. It is just like any diet. If you’re back to your original weight then what was the point?

This require a lifestyle change.

Deep Work is about increasing our mental capacity to reach new heights in getting important things done.

Setting aside hours a day of uninterrupted work sessions. Scheduling out your work day. Being diligent about what to focus on.

I have noticed this has offered me more rewards than before.

More time with family. More productivity in the best way. Less busyness, higher quality output.

Newport offers several tactics to support how we can incorporate “Deep Work” into our daily schedule. 

Some are interesting. However, I fear many won’t take them seriously. So I offer two simple suggestions to be more productive and reach new heights.

  1. Use “Do Not Disturb” feature on your phone and laptop religiously. When you are working on important work. Turn it on and focus your attention on your work. No notifications.

  2. Turn off all notifications. I mean all of them all the time. You choose who to give your attention to and when.

After some experimentation, I tend to prefer the second option. I get so much more done. It’s ridiculous. Almost like a super power or what dunking on someone might feel like.

This by no means is easy to do. I still struggle with this as an entrepreneur and being a part of a growing startup my time is often fragmented. That’s ok. Just keep doing the best you can and try to block out a few hours of uninterrupted a day. 

In a deep working session, focusing on the task at hand is critical. An innocent email popping up can derail everything.

I’m not against social media and as Newport says it isn’t a “moral” issue for him. Not for me either. It is all about getting things done. Important things.

Be focused about where your attention goes and to whom.

This isn’t easy but I can promise you one thing. You’ll find life more rewarding.

It turns out we don’t need to be connected all the time. We just need to go deep.

This is the “Deep Life.”

Amazon HQ Blunder

I’m not quite sure what corporate folks think when they make blunders as the one Amazon did with deciding its next HQ location.

Well, maybe they meant to do it this way. During the review process cities across America vying for Amazon’s attention sent in their detailed proprietary city plans to lure the giant.

Essentially, Amazon now has detailed plans on how cities will expand and what they are planning to do next. These plans give Amazon a significant advantage with their corporate expansion plans.

The hunger for growth is getting ridiculous on how far corporations will go for any advantage.

Jeff Bezos also recently said he thinks Amazon will eventually fail. So, what is the plan? Take as much as you can while things are going well?

This total disregard is a significant reason society is falling out of love with tech. Facebook is already in some deep trouble. Google also.

I doubt they are in trouble trouble, but things do feel a bit different.

What happened to thoughtful business? Is there even such a thing?

I for one am for the “thoughtful revolution.” It’s time.

Apple Music vs Spotify vs Google Music

To determine which service is the best we have to go back to the roots of all great music. Finding that track, you could bump over and over again.

Remember Rasputins? Or tower records? Or your local record shop?

For my friends and I, it was always fun to walk into a record shop and sort through CDs. For you, it may have been crates of records or tapes. It was the thing to do on a Saturday afternoon. Usually when it was too hot to play basketball. The cool AC at the shop was just what we needed.

The enjoyment was always in the discovery. I got good at flipping through those CD cases fast. Running back and forth from the rap section to R&B then back wasn’t as annoying as it sounds.

When 2Pac’s “All Eyes On Me” came out we knew it was going to be good. Every single track was and still is a classic.

The challenge though was we didn’t have enough money or time to discover all the music. We could have dug through music and argued about west coast vs. east coast hip-hop all day.

The Winner?

Fast forward to 2018 and all the hype is streaming music. Every service now touts 30 million-plus songs in their database. High-quality streaming. Playlists. Every service is necessarily the same. Except for one. Apple Music.

Apple Music figured out and emphasizes the one crucial thing about music. Discovery. It is at least half the enjoyment of listening to good music was the journey to find it.

It brought me back to flipping through those CDs or finding that rare B side track.

I was a long time Spotify user for ages. However, with Apple Music, I find it easier to discover music and browse around.

The “For You” area is quite excellent at recommending new tracks. I recommend getting the family plan to avoid mixing in nursery rhymes with TJR and Steve Aoki although Apples’ algorithms do an excellent job of presenting different genres and playlists.

In the end, all the music services provide the same basic functionality — extensive libraries and customizations.

Apple Music though does the best at focusing the UI and UX to the best part of music. Discovery.

Diversity will help your company make more money...seriously!

Is diversity in the workplace just a cool statistic we talk about or a critical part of your company?

Let’s forget for a moment diversity, in general, is just the right thing to do as a society.

Let’s forget that no matter your race or gender, equality and inclusion should never be an issue.

Let’s say with all the recent events you’re still not on board with diversity.

Let’s forget for a moment diversity in an organization could be the most important strategic advantage your company could ever deploy.

Wait! Let’s not forget that one.

You are running a business, and it's has been created to make profits.

“When it comes to building a product, diverse thinking helps organizations appeal to a larger customer set by incorporating different voices. After all, you can’t sell to people whose perspectives you can’t understand.” - Hackernoon

Still, don’t believe it?

Advancing Gender Inequality

California recently became the first state to require a woman on a corporate board. In a rare message included in the bill, Gov. Jerry Brown said, “I don’t minimize the potential flaws that indeed may prove fatal to its ultimate implementation. Nevertheless, recent events in Washington, D.C. — and beyond — make it crystal clear that many are not getting the message.”

Government agencies are forcing the issue of diversity because people are not getting the message. Force feeding is truly sad we have to resort to political force.

It is to our strategic advantage as a company to maximize shareholder value, and diversity does just that.

The one reason to convince you diversity is important is the company will build better products with a more diverse workforce and diverse thinking.

You will make more money!

This also includes diversity from different ethnic backgrounds and races.

McKinsey & Company reported that companies in the top quartile of racial diversity are 35% more likely to have higher financial returns than the national median in their industry.

Product Development and Diversity

Let’s focus on the product side for a moment.

In our podcast episode “Machine learning and data bias,” we discuss actually how unsettling a lack of diversity can be for a company. For example, many claimed Pokemon Go discriminates against predominantly minority neighborhoods. Whether this is true or not is one thing, the main issue here is we should be using technology to break down these barriers, not put more up.

I am particularly interested in Internet of Things (IoT) and autonomous cars. I have heard from friends some smart assistant devices have a hard time understanding women. Interesting. I am also curious who is building all this self-driving technology? Are they all males? Are these companies considering how different people drive and their product experience?

Without a proper understanding of the user base, the user experience could suffer, resulting in lost revenue and a tarnished reputation. After all, over half the population are women. Probably a good idea to include different perspectives.

Don’t blame the algorithms either. Chris Stoll, a software engineer at Skiplist wrote a fascinating piece on machine learning and data biases. In the article, he discusses that data isn’t just data. It is indeed the people who build these algorithms have their own intentional and unintentional biases baked in.

We must account for these biases and diversity.

However, an issue companies face is there are just not enough minorities and women in tech. The limited pipeline of good talent is already a challenge. Tech companies, in particular, are very competitive when it comes to software talent.

While we can’t speak for other companies on fostering a more diverse workplace, especially in the software industry; we observe and learn. We work on projects that span many different industries, and because of this, we prioritize a diverse staff. It’s quite interesting to see the different perspectives from tech-leading companies to more traditional ones that are transitioning to more of an emphasis on tech.

The value of a diverse staff and varying backgrounds and perspectives becomes quite apparent. We have the unique opportunity to see what works for different types of companies when it comes to diversity, and to witness the challenges.

This perspective allows for us at Skiplist to continue improving and growing, ourselves.  Without a doubt, we see that more diverse teams tend to produce better results.

Our employees come from various non-traditional software backgrounds as Scott Stahl, a software engineer at Skiplist discussed in his article, Does diversity matter for success?

We’ve also seen that diversity of thought matters to our team, and not just for software. Our marketing coordinator, Samantha Wolfe reviews and edits our content. As someone who previously worked in the public health and non-profit field,  her perspective is equally essential to align what we say to the world, mainly because she does not have a technical background.

We know that Skiplist has room to grow regarding diversity and we look forward to that challenge. We can, and we will continue to do better. And in that same arena, we will continue to seek out partnerships with like-minded companies that hold the same values.

This article was originally published on

The iPhone "Notch" a Brilliant Design Choice

Don’t hate the iPhone notch


So much has been written about the infamous "notch" on the iPhone X. Surprisingly many hate the notch. True to Apple fans they are passionate about whether a feature is right or not. 

I am an Apple design fan and I started to wonder whether the notch was a mistake. I personally like the notch. All the notch haters got me thinking, did Apple miss something?

Well, no. Lets get something straight, they are so far ahead in design concepts than any other company out there. So they know way more than you, me, and everyone else. They know what they are doing. 

Sells itself every time you take it out at a coffee shop or a restaurant. 

Then I realized the notch is actually done on purpose. Or at least this is my theory. My reasoning is the notch is truly a distinctive design feature. 

Every other phone manufacturer is making phones that basically look the same. Especially when you put a case to cover the logo. 

A major part of an iPhone is that you have an iPhone. It is a luxury item. 

Iconic brands have their distinct logo. You know a Louis Vuitton bag when you see the famous LV logo. You know it from across the room. You are helping them advertise. Brilliant. 

This is independent of whether you care if people know you have a LV bag. This is all part of building lasting thoughtful products. 

Design with purpose. Engineer with purpose. 

Bye Bye iPhone Home Button

The iPhone X removed the famous home button. Everyone knows the iPhone with the distinctive home button. Now gone they came up with the notch. This all comes together to build iconic products. Everyone is talking about the notch. So much so that even people who don't have an iPhone X know one when they see it.

Sells itself every time you take it out at a coffee shop or a restaurant. C'mon you have to admit this is brilliant stuff. 


This also applies to the camera bump. Yeah we can argue about the need for a certain camera lens. Blah, blah, blah. You think Apple doesn't know how to make a completely flat phone and camera?

It's done as a distinctive design feature. Embrace the oddities of design. How many companies can pull that off? Not many. 

Even with a case covering the logo, you can see the bump. Making a call. Everyone knows you have an iPhone. 

Lay the phone face up, you see the notch. Everyone know you have an iPhone. Again, I am not talking about where you like the design or like Apple. 

The main point is design matters. 

Thoughtful Design

Often we build products by assuming we know more about a product than the company building it. However, great companies know their user better than you and also know their presence in this world better than you. 

Apple is selling all the time through design and great engineering. So good, they can't be ignored. 

When building software, always start with why? Why would our users care? Why would the market care?

The result should be a full understanding of the ecosystem surrounding you and your product. Don't take design lightly. Build unique incredible features that are so good, users remember and they can't ignore you. 

Working with individuals who are design thinkers and thoughtful builders will dramatically increase the chances of success. 

Here's to the notch. Jk.

What is blockchain?

What are some important things to consider when thinking about blockchain?


The Dotcom boom and bust was a wild ride. From the rubble came a wave of new tech giants - namely Google, Facebook, and many others. Tremendous investments were made to build out the foundation of the internet.

Wireless communication and the growth of LTE, Wifi, and Bluetooth have completely changed our lives. Mobile communication and the upcoming launch of 5G is going to be really cool.

The financial crisis and housing crash was an interesting experiment that seems to be repeating itself. Banking is primed for a major technology overhaul.

Every now and then we encounter seismic shifts in how technology will shape our future. Currently, that new technology is the Blockchain.

You have probably heard of it by now. If you haven't then this article is not for you and we  want to know if you living in cave.

Bitcoin and Ethereum are examples of applications built on the blockchain.

A quick summary, a blockchain is a digital ledger of records or transactions arranged in data blocks. Blocks of data are linked together through a cryptographic validation known as a hashing function. Follow the link if you want to nerd out for a bit or have trouble sleeping.

Linking the blocks together forms a blockchain.

What makes blockchain and this type of data structure so hot is applications can be decentralized. Meaning data is not stored in any single location, data is accessible by everyone, and is immutable. Meaning it is nearly impossible to hack.

There are tons of resources online that dive into the basics of blockchain. We won’t be covering that here but focus more on enterprise blockchain applications.

Our goal is to discuss important aspects to consider when working with blockchain technology as well as a few use cases for enterprises.



Enter the enterprise

A survey of 800 executives, featured in the same book, suggests 58 percent believe that up to 10 percent of global GDP will be stored using blockchain technology.
— McKinsey

Decentralization, cryptocurrencies, and Bitcoin? How can enterprises of all sizes take advantage of blockchain technology?

Mainly for enterprises Blockchain plays an important role in fundamentally changing how we think about exchanging value and assets, contracts, and sharing data. The blockchain allows enterprises to transparently and digitally track assets as one example. As well as creating new ways of cross-organization communications.

Do you need Blockchain?

In 2017, many enterprises began experimenting with blockchain technology. This will continue in 2018 but for some blockchain will be ready to go from experimentation to a live deployment.

There are several enhancements being made to technologies such as Bitcoin, Hyperledger, and Ethereum to handle a higher scale.

A current limitation of blockchain are transaction latency and higher throughput. A large enterprise may handle 100,000 transaction per seconds where ethereum can handle only 14 transactions per second.

Enterprises will need higher throughput and better latency. You will need to evaluate your current and future needs and have a good understanding of the volume you expect to see. This will surely be a major factor in whether blockchain can work for a particular application. This isn't to say you should rule out blockchain. Just something to consider.

In addition, a blockchain enterprise proof of concept (PoC) may include only a dozen participants where a truly scaled permissioned blockchain will have dozens or thousands of participants. Onboarding and architecture design will play a critical role in how successful a blockchain will be in your enterprise.

Other considerations are ensuring the system avoids downtime. Traditional systems use replication and redundancy to ensure system avoid outages. Similar techniques are available with the right blockchain technologies.

Further, security is the most important aspect to consider. Permissioning models and authentication enable members to digitally sign messages and transactions.

Deploying blockchain is always the moment of truth as now it is exposed to the world. Any blockchain project must consider security early on in the development process to avoid major changes later. Basically, be friendly with the IT person. They’ll help you avoid trouble later.

Use cases for Enterprise

Let's get to the more practical aspects of using blockchain technology. There are many potential use cases. Quite a few are looking way too far ahead in what can actually be deployed and be usable.

Our belief is software should always be usable and thoughtful. This starts with taking an iterative approach and build a strong foundation. Whether we are working on a core project or something with an innovation lab, the process of testing and learning is a skill often forgot today.

Smart Contracts

The fundamental benefit of blockchain technology is a consensus of the participants on the network is needed to verify and approve transactions. This would allow an enterprise to dramatically limit fraud.

In theory, blockchain features can be used in supply chains, product development, internal workflows, pretty much in every department.

A good proof of concept may be around developing smart contracts. Software contracts built on the blockchain that enforce the performance of a contract without third parties. The transactions on the contract are tracked and cannot be reversed.

In addition, smart contracts eliminate or reduce the need for a middle-man. Dramatically reducing human errors and associated costs.

Smart contracts are great use case to test blockchain capability for your supply chain. Industries such as banking and insurance are already pushing forward to deploy smart contracts on blockchain secure platform such as Ethereum.

The benefits of a smart contract:

  • Security

  • Speed

  • Potential lower costs

  • Standardization

Potential areas where you could use smart contracts:

  • Shipping and logistics

  • Asset management

  • Infrastructure management

  • Supply chain

  • Cross-border financial systems

  • Life-term insurance

  • Real estate contracts

  • Hospitality services like Airbnb

Blockchain technology is going to play a major role in shaping our future. We can all agree the internet needs to be more secure. There is a tremendous amount of hype around it but make no doubt blockchain is here to stay.

As you build elite talent, bringing them into your organization can take time without any guarantees or productive outcomes.

Blockchain projects are a great use case to partner with a development firm such as Skiplist. The first step is a short discussion to see where we could potentially help. Often we can guide you to the best path whether that may be to do more research or start on a potential proof of concept then move to scaling the project from a MVP to a fully deployed product.

Where do you begin with blockchain?


Start with a proof of concept with blockchain.

Most of what is written today about Blockchain technology is theoretical. What could potentially happen with blockchain and how disruptive it will be. 

There are articles after articles on how blockchain will disrupt X industry and change everything. Finance, supply chains, contracts, or venture capital, nothing is safe from blockchain's disruptive force. 

Let me know tell this is a lot of hype. Not to say it isn't true but hyped what too fast. This is the environment we live in now where something can go viral immediately. 

Hype is good thing when it comes to technology particularly. This is mainly how so much money gets poured into new projects and companies. The hype train brings in money so the infrastructure can be laid out today for a better tomorrow. 

Blockchain is not going anywhere. In the US we have a fairly good banking system and things generally work well. However, for many in the world their infrastructure is terrible. 

A basic thing such as keeping your money with you is not possible. Governments and banks hold all the cards. Extremely inflation in certain countries make the Bitcoin volatility look like a kids seesaw. 

Proof Of Concept

What most companies should be doing though is to start dipping their toes into blockchain. Start with a proof of concept (POC) and see what results you get from these tests. Maybe a smart contract can streamline the supply chain better and reduce costs by 15%. Then make bigger investments into a more wide spread architecture. 

There is not also a strong need to build out a full blockchain group internally. Use outside resources and freelance developers to build POCs. 

Test. Iterate. Test. Iterate. Look for areas to double down on. Then full steam ahead. 

Design Review: ProtonMail


Encrypted and based in Switzerland? Sounds interesting. 

On their homepage you'll find a bunch of cool features. At least cool to me. Swiss privacy. End-to-end encryption. Anonymous email. Open source. This is all good but ehhh. Intriguing for a nerd but the market doesn't really care. 

Wait a minute...then they list easy to use and modern inbox design. Ok now we are talking. "Security without the hassle" and "Security with productivity" is catchy. This the market does care about. 

Secure email will never get mass adoption without a great user experience. In the past, not many companies were able to solve this problem. When you think of security and encryption, I immediately think complicated. 

Protonmail makes it very simple. Just as simple as creating a Gmail account. This is really the most important factor. The underlying technology is an after thought when you just want to check email. 

The purpose of Protonmail and similar services is to keep your communications secure. Away from prying eyes. Corporate and government eyes. Even from hackers. You may think you have nothing to hide. That is true for most of us. I am mainly interested in security from hackers and general privacy when it comes to email. 

This led me to Protonmail. Check out this video for more into. You got privacy?

Sending an email message is like sending a postcard, says scientist Andy Yen in this thought-provoking talk: Anyone can read it. Yet encryption, the technology that protects the privacy of email communication, does exist. It's just that until now it has been difficult to install and a hassle to use.

 I signed up for the free account to get 5MB to check out the service. I almost immediately signed up for the paid account. The setup was extremely easy and the user experience is great also. 

For example, out of the box swipe right is archive an email and swipe left is trash. Simple. Touch ID setup was easy. Everything you would expect was simple. 

They really thought about the user experience. Even using the ProtonBridge to setup encrypted email on your desktop was easy. The bridge also can setup your Apple mail for you. Brilliant. 

The web portal is very good. They even show you how to secure your domain. This may be for a more advanced user but wasn't too bad for me. 

Not perfect

There are some drawbacks. It can be confusing to understand which plan to buy. Some plans give you 20G of total space. Then some give you a different space per user. Then another one included VPN. 

Setting up different email addresses seems quirky also. 

The major drawback is contacts isn't integrated with iOS. Meaning I can't save Proton contacts on my iPhone to a iPhone contact directory. I understand they want to keep it secure. Problem is if someone emails me and I save their email into a contact, I won't be able to text them from iPhone. It doesn't transfer over. 

Another big big drawback is no calendar support. This is a big problem for me. They say its on the roadmap. Even if it does come out I don't we will get iOS support. 

This leaves me with still having to use Gmail. I'll live with it for now. At least I got one secure email account. Nice work Protonmail.