Freedom in Progress

In the early days of Polar Notion, it felt like we were saying yes to everything. We hadn’t found a sweet spot and being quite honest, we had bills to pay. When times are tough and work is slow, any skill you possess is worth leveraging. Eventually we had enough breathing room to think through the type of company and brand we wanted to be.

Better Before Bigger

Today, we help businesses get better before bigger. This focus required us to do it for ourselves first. We have a clearly defined vision and values that guide the way. Since we work on behalf of clients, our name does not publicly accompany our work. We embrace this tension, thus adopting a secret-society-esk nature. Unapologetically, our quirky team and wild ideas are as much of who we are as the software we write or the design we create.

Exploring the most valuable elements of our work, it’s became clear that utilizing our experience and strategic insights increased value to clients. Instead of focusing on building to spec, we’re helping clients determine what to build and collaborating on the path ahead.

Each week, I sit down with entrepreneurs and business leader to shape the future of their business. Rejecting the notion that we are no more valuable than the code we can write, we push to refine ideas into their truest form.

Developed over time

In hindsight, we have sought this freedom all along. Since 2012, we felt the conflict of craftsmanship and desire to do remarkable work. We desired it, but we had not earned the right. Today, experience backed insights flow freely. Having witnessed hundreds of projects of all shapes and sizes, our blades are finely sharpened. Only a fool would claim to have all the answers but we’ve survived our share of hard times and distilled our learning into actionable insights. These experiences help us save others from much of the hardship and pain we’ve walked through.

Getting here was not easy. The deliberate attempts, thoughtfulness, risks, and investments took years to refine. The freedom and trust we receive from clients was hard fought and fiercely protected. It’s a consequence of healthy relationships and deliberate practice. There is not a fast path to credibility.

Go boldly forward is much our track record as it is our battle cry.

Adding and Removing Zeros

As we think about the evolution of a business, it’s growth and efficiency go hand in hand. It’s important to continually improve and continually growth. Without continual improvement, it’s easy to fall into complacency or get sloppy. Without continual growth, energy is spent balancing an arbitrary equation of profit and lose.

Simply put, if you are not actively improving, your passively diminishing.

Zero the Hero

While continual improvement may sustain the business, from time to time there are opportunities to innovate. Whether through a new approach or impactful technology, the change is exponential not linear. During these seasons, you have the opportunity to add and drop zeros, not percentages.

Over the last 3 years, we have built and iterated on software for an education company. Previously, their sales were dependent on physical books that had to be printed, packaged, and shipped. Every sale had hours of overhead and labor. Today, their entire collection have been converted to a digital experience that can be sold thousands of times with little additional effort. They dropped a few zeros from their costs.

At New Story, we are expanding our reach to the entire housing sector. Moving beyond building internal tools, we are making our web and mobile technology available for other nonprofits. This shift has allowed us to set our sights on the 1 billion people without adequate housing, not just the hundreds of thousands we could impact alone.

The skill of adding and removing zeros does not always come in the form of massive overhauls or complex tools like 3D Home Printers. Within Polar Notion, we reimagined our client on-boarding. On-boarding typically took three or four days of contracts, invoices, and setting expectations. The process today is more value packed and can be completed in 3-4 hours across multiple handoffs.

Better Before Bigger

Innovation and iteration go hand in hand. Healthy businesses combine big risks and proven processes. It’s not one or the other. It’s both. Focus on getting better and taking big swings.

If you’ve managed to add or remove zeros from your workflow, I’d love to hear about it.

Spilling Secrets

Over the years I’ve found myself defaulting to complete transparency. It’s helped me develop a feeling of authenticity and a deeper sense of generosity. If I have a perspective, experience, or behavior someone else might benefit, it feels selfish to stay quiet.

This openness and vulnerability intensified around the 5 year mark in our business. Following a near catastrophic financial issue for the business, I found myself scrambling. It was a desperate attempt at survival that led me to reach out to mentors, friends, and even strangers. The support and encouragement was humbling and invaluable. In turn, I’ve sought to do likewise. Rather than limiting it to those bold enough to ask, I began writing more and sharing it with those who might not feel comfortable reaching out.

Throughout this season, I also felt a prompt to express gratitude to those who had helped us along the way. Our business has been built on the support and generosity of friends, families, and clients. At first, it was about giving me something positive to focus my attention but evolved into being more about the recipient and cheering them on in their journey. Either way, it aided me through the troubling time.

What about competition?

Naturally, this sparks conversations about trade secrets and giving away our competitive advantage. I’ve heard dozens of solid arguments that keep me questioning the merits of my approach. To date, I am undecided. Until I receive compelling evidence to the contrary, I’ll continue default to unbridled transparency. We have become more articulate with our clients, move to transparent salaries internally for team members, and even began passing along helpful strategies to competition.

Aren’t you worried about companies copying you?
What if you share too much?
Could someone beat you at your own game?

Bring it on. Personally, I love the accountability that surrounds transparency. It forces us to have our own house in order and continually improve. As we invite peers and competitors to compete at our level, high tide raises all ships. Plus, if you’re the overly competitive type, it’s actually advantageous to put yourself in a position where competitors are following you. Copying you means they are focused on you, while you’re free to focus on serving your customers or clients. You have them right where you want them.

It’s also worth noting that what works for me and my businesses will not work for everyone. For instance, transparency without accompanying integrity will end poorly. Also, following our process without the deep conviction in it’s value will result in unsavory outcomes. Doing the same thing, with different intentions, will not produce the same results.

No Secret Sauces

Think about your favorite dining experience. It’s unlikely the restaurant only has good food. They need more than great atmosphere. Attentive serving staff is not enough. My favorite restaurant has a great vibe, knowledgeable waitstaff, impeccable hospitality, delectable food, and delivers that experience every time. It’s the full experience. There is no special ingredient or a secret sauce, it’s about the full package.

In the same manner, I want to be a person where unrelenting generosity and unending gratitude are my differentiators. Not as a secret, but to be enjoyed by all.

Keeping it Practical

There is also a level of practicality to the process. Given the dozens of meetings I have each week, it’s exhausting to decide who I’m willing to share information with. Is there a conflict? Will they steal the idea? Can I trust them? No one knows. Rather than fixating on which version of the narrative to preserve, I’m freed up to share openly.

In parting, I’ll pass along a quote from Zig Ziglar what echos in my mind, “You will get all you want in life, if you help enough other people get what they want.” Living this way, I’m amazed by how fulfilling the work becomes when I stop making it about myself. Instead, choosing to focus more on adding value to others.

Building a Marketplace

Over the years, we’ve built plenty of marketplace solutions. Unlike feature based or business management software, the value of the technology within marketplace software is in the relationship that is facilitates. The most common formation is a two-sided market place. Two-sided marketplaces connect a seller and a buyer. Examples we’ve build include connecting law firms with project attorneys, job seekers with employers, riders with drivers, or even brides with wedding vendors. Two audiences exist and the software becomes the match maker. Their interests are align, they just need to be connected.

Two-sided Complexity

Two-sided markets have inherent complexities. A common complexity is around value. Once the match is formed, what keeps the customer and vendor within the system? Airbnb, for instance, matches renters with home owners. Since the behavior involves real world interaction, the two parties could conduct business offline in future interactions. It becomes the goal of the marketplace to add value beyond the matchmaking. In the case of Airbnb, the leverage renters insurance. If you skirt their system, they reserve the right to decline all claims if anything goes awry.

Craiglist charges certain markets for simply creating the listing. They expect you to handle financial transactions off system, but charge the vendor. Interestingly enough, Craigslist only does this in a few cities. Charging vendors in a small number of cities produces enough revenue to make it free for everyone else, which continues to increase adoption. is another fascinating example. When they fulfill their stated purpose, helping people find love, they actually lose a customer. Once you’ve entered into a happy, healthy dating relationship, their service becomes less valuable to it’s users. This tension can create a reverse incentive for the marketplace.

Triple the Chaos

Two-sided markets are complex, no doubt. But what’s more complex than a two-sided market? A three-sided market. That’s right, three audiences each coming to the table for a piece of the value-equation. In a three-sided market, the market software becomes the referee. The marketplace is responsible for maintaining the delicate balance of everyones’ best interest.

Imagine a triangle. The strongest form of a triangle is one in which all sides and angles are equal. A solid market with three parties should maintain a similar balance. If one party senses misalignment, it becomes more advantageous for them to leave. Over time however, the balance tips as each party pushes for their best interests.

Take recruiting firm for instance. Job candidates sign up, employers post jobs, and recruiters access the candidate pool to fill positions. Recruiters, compensated on a percentage of the employees salary, are incentivized to pursue high salaries for employees but only for those willing to pay either commission. Employees, incentivized to find the most purpose filled, flexible work at the best pay, field as many options as possible to make sure they find the best one. Meanwhile, most employers want to keep the process short, hire at-or-below market, and find someone who fits their values. Their interests overlap, but clearly conflict along the way.

Defining the value and continually communicating it to each party is essential to maintain equilibrium.

Chicken or the Egg

Whether the market has 2 or 3 sides, a chicken-and-egg scenario quickly forms. Imagine trying to use Uber without enough drivers. It doesn’t work. How about enticing drivers without anyone to drive? The marketplace depends on having enough people on both sides of the relationship.

Fortunately, we have noticed a trend. It’s easier to get the vendors than the customer. The audience who stands to gain financially is easier to build, so start there. We have speculated on why this might be, but it’s important not to overcomplicate it. The one who is making money is more likely to show up than the one you’re expecting to spend it. Eventually you will need the other side of the market but we’ve seen great value in moving fast and confidently building the list of sellers first.

Start Simpler

Building marketplace technology is complicated enough, don’t add unnecessary weight. Starting simple to prove the concept and validate the value will save time, money, and headache. I shared recently about starting smaller, which includes insight into a 3-sided marketplace. The big takeaway was how effective a simple email blast proved to be. No fancy software or complex system, but a simple touch point that connects key audiences at a consistent interval. Find the smallest measurable step and get started.

In the end, you should expect a 4-5x increase in complexity when building a marketplace. There are unknown technical constraints and instability in the increased human element. There are more variables than a service based business or a suite of products, so you’ll have more people with misaligned interests. Choose wisely. If you imagine an elegant three-sided market, push yourself to start with two. If you’re planning to invest in a two-sided market, figure out how you can validate with half the market first.

Aligning Software Pricing and Value

Not everything is worth a subscription.

We all know what it’s like to start using a software product only to see the paid plan is $20 per month. It’s one small feature we use but the cost is twice what I pay for Netflix. It doesn’t feel worth it.

The value of the tool and what it costs are misaligned.

The Flip Side

While some technology feels overpriced, there are others than feel like a deal. At polar notion, we spend over $300 a month for Slack. Our team and clients use Slack as a continual communication tool. It facilitates all conversations. Slack saves us hundreds of hours combing through emails and tens of thousands of dollars in efficiency.

We pay a lot for Slack, but we get more than we pay.

The Tension

How do we reconcile this when building technology? Someone has to pay for it to get built.

Increase the value before the cost. It’s not a matter of adding features. Rather, it could be providing more detail about other use cases. I use a recording and dictation app that began encouraging me to record meetings. I sync my calendar and the transcript is auto-named to match my calendar invite.

Charge differently. Subscriptions are popular but it is not always appropriate. Technology companies existed for decades with upfront pricing and charging per version.

Embrace ‘quid pro quo’. Dropbox grew rapidly through allowing users to increase their storage space by referring friends. It engenders customer loyalty and expands reach.

Wait. The most lucrative financial model is likely not the most obvious. Figuring out creative funding strategies to postponing charging customers will allow you time and experience to create the most valuable plan. When we launched Startup Picture Day,  it was obvious that quality headshots were important for startups and entrepreneurs but the cost they were willing to pay was insignificant. So, we funded it ourselves and through generous sponsors.

The Point

It’s not enough to slap a double digit subscription on your product and expect customers to pay. The value has to be in alignment. When in doubt, make sure the value is weighted in favor of the customer or start with charging nothing.


Swing, Swing, Swing

There is a restaurant down the road from our office. We’ve eaten their quite often but they always manage to get our order wrong. If I had to guess, they get it right about 30% of the time. It’s abysmal. It’s low on our list of lunch places.

In baseball, they have a name for players who only get their job right 30% of the time: Hall of Famers. That’s right, the best players in the world hit the ball less than half of the time. Over the course of their career, a baseball player will strike out thousands of times.

Taking swings

Conversations about failure are everywhere. They cover the importance of failure, trying things that might not work, doing things that don’t scale, moving fast while breaking things, and so much more. Almost as popular are counter points about quality, excellence, and seamless experiences.

Witnessing this trend, it’s clear they aren’t counterarguments at all. There may be some mild contradictions, but it seems more a difference in how they define failure. Few people are proposing to build failing businesses or risk more than you can afford to lose. It is different than the failure we were taught to fear in school.

It is making measured attempts, calculated attempts to validate an idea. Taking swings.

The path to innovation is not losing everything or continually starting from zero. It’s about stepping up to the plate as often as possible and swinging at what comes your way. You may strike out. You may even lose a couple games. Fortunately, no one is counting on your to get it right every time.

Recent Events

In a recent meeting with our leadership team at Polar Notion, we wanted to test the idea of design retainers. In hopes of filling in the downtime between projects, retainers seemed like a great fit. Conversation quickly began about creating a landing page, defining deliverables, and understanding the value to clients. Fortunately, we took a step back. Rather than creating this elaborate campaign, I ended up sending an email. 1 email to a client who seemed like the best fit for this service. “Hey man, we’re testing out an idea. Can we experiment on your brand for 3 months? Cost is on us.” Within 10 minutes, we had our first retainer.

The second email was to another close match. This time, the cost was $500 per month. A rock bottom price and steal for the value we provide, but optimizing the value wasn’t the point. We just wanted to make sure the service was worth paying anything for. We got an enthusiastic ‘yes’.

I sent a few more emails, wherein people said ‘no’. In my mind, these ‘failures’ were low impact and part of learning what people wanted. Months later, we now have a body of work that supports this service. The results are stunning. The deliverables and limitations have been refined by actual conversations with real clients. Whenever we get around to creating a landing page (it’s looking like we may not need to) the content and value will be clearly defined. There was no guessing or big investment, just quickly executed, small swings.

Checkout more thoughts on starting smaller. Also, we have a few ‘seats’ left on our latest iteration of the design retainer. If you’re interested in making consistent investments in your brand identify, let’s chat!

Start Smaller

In 2016, we built a streamlined recruiter management system. It allowed candidates to connect via LinkedIn, recruiters to post jobs, and employers to filter prospects. The interface was clean and polished. The value was well defined and benefits were obvious.

For months prior, the client also had been working to build an email list. Every week a newsletter would be sent to job-seekers with top jobs in the industry. Employers would also receive an email with top candidates. It was basic and simple.


In the end, their email list was 30x more effective at connecting people to jobs. It wasn’t much, but it worked. It wasn’t sexy, but apparently it didn’t have to be. When he approached investors, they couldn’t reconcile investing in an app when the traditional email was working well. “Comeback when you have a plan that capitalizes on the effectiveness of that email list.”

The technology was not the answer. It was about engagement. What did people actually use?

The early days of New Story, it worked much the same way. Instead of waiting until a revolutionary new platform was ready, one of the founders hacked together a few tools in order to prove the concept. They used a third party donation service. The progress bar had to be updated manually. Each “campaign page” was built from scratch. In light of today’s robust system, it’s nauseating  to consider the amount of manual work that must have been involved. It wasn’t amazing, but it was good enough.

When trying to identify what the market wants, it’s worth starting small. There is always time to get bigger and more complex, assuming you can survive long enough to build something people want.

Estimating Completion via Hill Charts

In high school, I ventured out with two friends to hike on the Appalachian Trail which stretches from Georgia to Maine. The plan was to hike for 5 days, covering about 75 miles. The distance would have covered the entire section within Georgia. On Day 3 a massive mountain was expected to be the highlight of the trip. Looking at the map and using some rough calculations, I estimated we would eat lunch atop the mountain in a few hours. We’d heard from others that it was one of the state’s best views.

As you might guess, I was wrong. Ascending the mountain took twice as long as expected. Conditions were rough and visibility was poor. We were exhausted by the time we reached the top and our lunch was devoured hours before. A thick fog left us with mere inches of visibility. No view and no highlight. From the summit, we made fast work of the descent.

Estimating is hard.

When it comes to project based work, estimates for tasks and deliverables are even harder. With changing expectations and unknowns, predicting requirements to ‘get the job done’ can feel like an impossible task. The difficulty intensifies when you consider that progress is not linear. If the project lasts 10 days, it’s unlikely that you are 50% complete on Day 5.

Complexity is Misleading

If complexity is front loaded, it may have progress slowly at first but is now picking up speed. Building software often follows this trend. If you plan early, later development goes a lot faster.

When complexity is backloaded, the early days may be smooth sailing though the majority of the progress lies ahead. Hiring new team members often works like this. You may communicate with, pursue, and interview a large number of candidates, though in the end all the value is in the offer being excepted by a single candidate.

There are also certain tasks that create bottlenecks for progress. If you are 20% complete but may not have the 1 necessary piece of information to move on.

The Hill Chart

Imagine you are hiking. At the beginning of the day you start at the base of the mountain. Over the course of the day you plan to summit and walk to a destination on the other side. Unless you have hiked the mountain before, it’s unrealistic to predict how long it will take you to walk down the other side. Until you reach the summit, more information is still needed.

Projects work much the same way. There are tasks you’ve done 1000 times before and others tasks that require more clarity before estimating.

In order to clarify the process and help the team visualize where things stand, our thinking has evolved. Rather than tasks being perceived as equals, they’re plotted on a hill. Items on the left require more information and insight. Items atop the hill have a path forward that only lacks execution. Items on the right done done.

When work is plotted in this manner, the conversation changes. Instead of broad questions about completion percentages, a helpful dialogue can exist around the items that need to move up the hill.

At the beginning of a project, it’s customary for some tasks to be on the far left while a few start at the top of the hill.  Throughout the project, tasks are regularly reorganized, discussed, and shifted. Since their place on the hill speaks to different constraints, discussion is allocated more appropriately. An incomplete item at the top of the hill is vastly different than an incomplete item on the left.

Strategy Feeds Execution

Strategy is among our most valuable work. In technology, it’s easy to get caught up in apps, features, and how it looks. We must consistently stop and consider if we are building the right thing. As I look back over years of building products and millions of times of code, my proudest moments involve software we avoided having to write. In contrast, the greatest disappointments involve a tremendous amount of time, energy, and effort spent on something that was ultimately wrong.

It comes back to strategy vs execution. Doing the work or deciding on the work to be done.

Great technologists are able to align technology with business objectives. This alignment shouldn’t only be at the beginning of the project. It must happen over and over as conditions evolve. This is typically the role of the technical cofounder on smaller teams and Chief Technology Officer within large or growing organizations. Building great software is important but far superior is knowing what is appropriate to build.

To illustrate the point, it’s worth exploring a few tradeoffs. Common tradeoffs include expectations, timeline, and quality.


What do they think they are getting? Assumptions are easy to make and hard to articulate. The phrase Minimum Viable Product, for instance, is riddled with assumptions. We all have different definitions of minimum and viable.

In the end, ‘expectation minus communication, equal frustration’.


When will it be done? The larger the project, the harder it is to predict. There is also an assumption that it has been clearly defined as to remove all uncertainty or confusion, which is rarely the case. Time is the most challenging constraint. It is always being spent. Whether we are planning or waiting, it is passing.

Rush through planning and the journey will contain more missteps. Take too long and the window of opportunity could close.


How good is good enough? As a child, there were times when cleaning my room took minutes and times when it took hours. The difference? Quality. Was I stuffing dirty clothes under the bed or cleaning, folding, and organizing them in their proper place?

Where a proper customer and market have not been identified, we’ve found quality to be less important. Without knowing who you’re optimizing for, it’s impossible to truly hit the mark. If building for existing customers, it’s worth the extra time and attention to get it right.

Continual Realignment

Historically, Strategy Sprints preceded each project. The tension emerges when constraints change while the work is underway. Is time spent adjusting based on new information or pushing forward on the given path?

You wouldn’t plan a road trip and jump in the car without a GPS or map. Strategy is a perpetual pursuit. Constant recalculating is crucial to long term success. For engineering projects, there seems to be a natural rhythm to proceeding two week at a time. Defined break-points forces pause, reflection, and reevaluation. Making informed adjustments will ensure you end up where you intend to go.

In the end, it does not matter what you’re driving, how much the trip cost, how long it took, or how you get there if you arrive at the wrong destination.

How to Launch an Idea in 1 Month

A 4 week overview to move from idea to entrepreneur.

Keeping things simple is often difficult. When creating a physical product or software solution, there are hundreds of decisions and trade offs that impact time, budget, and end product.

We’ve put together a straight forward game plan for moving from idea to reality with speed and confidence. Success isn’t a guarantee, but it frames the process around well defined milestones. Our approach doesn’t claim that ANYTHING is possible in a month. Instead, the focus is launching something of value, start to finish, in a month.

We’re broken it down into 4 weeks:

  • Week 1. Research + Refine the Idea
  • Week 2. Plan your Approach
  • Week 3. Build Prototype + Audience
  • Week 4. Launch and Refine

Week 1. Research and Settle on an Idea

A solid idea solves an actual problem, provides unique value to customers, and aligns with the customers interests. Identifying problems involves a level of empathy with your ideal customers. Providing unique value to the customer requires research around existing tools and products. The most compelling offerings stand out from the competition.

What is a problem that you or those close to you have identified?

Week 2. Plan your Approach

Assess the constraints you’re working within. Common project constraints include desired features, time, and budget.

It’s also worth considering your endgame for the project. What are you trying to accomplish? Your approach to merely solving your own problem should vary greatly from someone seeking to redefine a category.

What is a solid first step in attempting to solve the problem?

Week 3. Build Product + Audience

By Week 3, it’s time to get started. Many find it surprising that you would get started on building half way through the month, but this demonstrates the importance of planning. Building the wrong thing and adjusting is more costly than starting ‘late’ on the right path.

It’s important to remember that promoting shouldn’t wait until the product is complete. You can build your audience before or during the creating of your actual product. Early stage customers and supporters are often your greatest advocates and appreciate being involved in the early stages.

Week 4. Launch

Done is better than perfect.

If people aren’t looking at it by Week 4, you’re behind the ball. It’s important that at least a few people are able to weigh in on the process. You don’t have to share on social or drop $1,000 on Facebook ads, but challenge yourself to email a link to 3 friends.

Of course it’s not 100% complete, but you’re going to learn more than you realize by putting it in the hands of prospective customers.

What do customers think of your product?

Your idea is closer than you realize to becoming reality. Thoughtful, consistent effort can have you validating your idea and gaining momentum in a relatively short amount of time.

Start somewhere. Start today.

For the month of November, we’re inviting startups and entreprenuers to take the journey with us. While many are participating in conjunction with the Product Hunt Hackathon, the insight here isn’t limited to one event.

If you haven’t already done so, register for the Product Hunt Hackathon and hold yourself accountable with thousands of other entreprenuers and dreamers around the world.

If you’re ready to go but don’t know where to start, shoot me an email:


Originally posted on Medium.