This is the transcript from a three-minute talk I gave at Side Project Society recently. I crammed a lot in those three minutes, and I hope it encourages you.

Photo by @april_lelia on Instagram

Photo by @april_lelia on Instagram

As a UX professional, I care deeply about talking to the people I build products for and meeting their needs, and, as I often preach to others, so much insight is hidden deep in the bowels of casual conversation. So, it should come as no surprise that a string of these types of conversations changed my career and helped me launch multiple successful side projects, starting specifically when I decided to move on from doing creative media in churches.

I decided to ask what I call God—you can call it your gut if it pleases you—hard questions and decided to listen to an inner voice, instead of making it scream like we’re prone to do. From there, I knew my wife (the smartest person I know) would help guide me. I asked God and April hard questions often and listened intently to their responses. I still do.

When I had final interviews for one startup and a massive company that both offered exciting jobs, I asked them directly about my family coming first. I listened to their response.

So, I didn’t take either of them because I asked good questions. Later, I’d have lunch with John Saddington, who would actually end up telling me what to look for in an opportunity. I listened to him.

When I interviewed at Pardot, and my then boss told me he wanted me in a different position, it rang of what John had told me, so I asked the owners of the company how they approached running a company and how they felt about my family coming first. I listened. I launched my career in UX there, which has felt like what I was always supposed to be doing. I now affect thousands of peoples’ lives every day.

When that same boss encouraged me to keep up the public speaking, I listened. I toured Europe last year.

When I went to Grok several years ago, I asked a group a question about a music startup I’d worked on. Their answers directly led to a long-lasting partnership with local record stores in which we’re not only making money, but a difference for these stores.

When I had an idea for something now called Evermore, I dedicated a year to asking people about their needs, and truly listened. I asked a smart, older mentor type a question about pricing and listened. A friend of mine became my co-founder because I was listening while we were talking casually one day. It all paid off: we’re growing, our customers love us, and we’re achieving product-market fit more quickly than most.

So, stop trying to get the answers you’re looking for.

Start talking to smart people, ask hard questions, shut up, forget about yourself, and listen.

People are always the key.

The unsung hero of achieving product-market fit is the space between checking checkboxes.

You’ve done everything right. You’ve prepared. You’ve researched. You’re experimenting. You have something worth buying. You have a business plan and goals.

The steady plod between idea and launch is well documented, and is honestly quite encouraging.

Even the time between launch and that first customer can be great. Unless you’ve made something that no one wants or are presenting in a way that interests no one, you’ll grab that first customer and celebrate with many gifs.

That space between your first handful of customers and that “rapid growth” everyone wants?

Oh, that’s mostly described as hard work.

Just pay your dues. Do things that don’t scale. Be patient. Move fast. Do literally everything at the same time. Don’t do too much. Experiment. Don’t reinvent the wheel. Look to your existing customers for more leads. Look for new leads from social channels.

This is the time where growth gains its momentum, but how in the world you can go about finding the hill to push growth down to gain that momentum is anybody’s guess. It seems to work differently for literally everyone.

Identifying Different Customer Journeys

Let’s take Evermore here, for instance. We’re now in this infamous period of hard work. How do we kickstart growth so fast that my business partner, Kyle, has to start hiring people.

And just so you know it’s not limited to unthoughtful startups, we checked all the startup boxes:

☑ Solving a real, validated problem and providing demonstrative value
☑ One full year of market and customer research before building
☑ Successful testing period
☑ Scalable business structure
☑ Pricing structure from successful business mentors
☑ Favorable, honest product launch coverage
☑ Converting leads to customers successfully
☑ Happy existing customers

All that planning and patience got things much further, faster than expected. It was even a very agile process: I’d never intended to have a business partner, but it was a very organic and obvious choice when the opportunity came.

But, now that we’ve tackled the part where so many businesses fail and have a sustainable way of operating, how can we take this solution to the world? How do we meet people where they are to tell them about Evermore’s value?

After all, we haven’t fallen into the trap of selling a vitamin. Evermore is definitely a pain killer for some. If someone’s wasted a weekend trying to do things they don’t care about with WordPress just to get their website working, they understand the value. If they’ve had a really bad experience with a hosting or theme or plugin company, they understand the value.

Evermore can also be a vaccination for many businesses: prevent ever wasting your weekend, or learning things you don’t want, or being hacked, or debugging a slow website.

There are two very different entry points for businesses that would benefit from Evermore, but that doesn’t mean the product is unfocused. It means we have to account for those entry points.

Finding Pivotal Moments

This is the hard work: how can you be the obvious choice when the decision is made by a potential customer?

In Evermore’s case, how can we be there when someone experiences the pain of lost time or money dealing with a frustrating issue, and speak to that? And, how can we be there when someone wants to make an investment in their business’s website that will last?

Everything gets foggy here. You can start diving into every famous phrase for marketing: thought leadership, inbound marketing, social engagement, content optimization and testing. It all comes from a good place. They are all truly promising methods for being top-of-mind for a potential customer, but every business needs its own custom combination.

Depending on your budget, you may be able to hire researchers. Do so if you can.

Perhaps you have $10,000 to run your first series of advertisements, so you can see what works. Do so if you can.

Regardless of your budget, though, there are two fundamental, scalable approaches to finding your potential customers’ pivotal moments.

Talk to People

Engage in more casual conversation with your customers, potential customers, and people who understand the problem you’re trying to solve.

Yes, you should sell when the time is right, but don’t miss the opportunity to have a discussion all the other times. Kyle and I are constantly talking to people about Evermore so we can learn and understand more about the pain—even though we already know more than almost anyone about the particular problem. Never stop learning.

Never stop having the casual conversations where you can glean insight from all that nonverbal communication and word choice.

Do What Your Customers Do

How do you expect to understand your potential customers’ perspective without actually attempting to see things from that angle?

Do some recon: read the blogs they would read, understand the search terms they use, and go to the events they go to. The more context you can have, the more adequately you can reach people when they need the problem solved that you can help with.

We’re doing all this with Evermore, but it feels like it’s a slow process. It’s probably not. Understanding how to take the power of open source to a market that doesn’t know to care about it is complex, and it should take time.

May this post serve as encouragement to you and myself: the hard work is confusing, but worthwhile.

October 3, 2014 — Leave a comment — In Blog, Business, CX, Entrepreneurship

There’s been no shortage of articles in recent months about the millennial generation, their approach to technology, and how your business will have to reach them on their mobile devices if you want to succeed in the coming decades.

Like this recent one on Wired, most articles of this nature go a little something like this:

“Millennials are immersed in their phones and oblivious to the world around them. They demand that products and designs be bonehead-simple, because they’re too impatient to learn anything else. They have some cute, somewhat redeeming qualities in regards to their connectivity to one another and passion for social justice. Yet, overall, we will have to deal with their inability to focus and work hard. You must fear the millennial, because they are coming of age, and there appears to be nothing that anyone can do to help them mature. You’ll need to adapt.”

And, if you think that thinly-veiled condescension is exaggerated, let me assure you that it’s not off by much. From the article linked above:

You’ve seen them walking around shopping malls, college campuses and summertime social gatherings — those packs of sleepy-eyed teens with their heads down and eyes glued to their smartphones. Even though they cluster together in groups, you notice they don’t make direct eye contact or utter any sounds to each other except to share a video or Tweet, since each is immersed in his or her own text message conversation or social media exchange. One might even be sending a text to another only a few feet away. Whether we like it or not, the zombie apocalypse is upon us and unlike the movies dedicated to this popular genre, the millennial generation will prove to be the most influential, distracted and finicky demographic in history when it comes to technology use.

I use hyperbole and sarcasm with the best of them, but I’m seeing a pattern emerge: contempt for millennials.

Contempt for your target market will sink your business.

Does it not take tremendous value to look past rude customer service at a store you walk into?
Or, put another way: do you love to give your business to people who think you’re dumb, but will take your money?

That’s just the outer layer of the onion, my friend. You can’t just attempt to deal with it because you want to grow your business and a generation is coming up you don’t like. You can’t just fake a smile and friendliness. It’s deeper than that.

Grok Your Users and Their Motivations

There’s endless exploration that can be had when we talk about understanding users and where your product or service or content fits in, but the point here is that assuming Millennials are impatient, aloof, uncaring, lazy, or shallow simply because of their age is unhelpful. This is the same trap we fall into when we overextend the utility of marketing personas and use them to assume how people will act based on demographics.

You have more in common with people who have the same motivations you do than those that are just your age, your ethnicity, in your field, or who live in the same area you do.

For more on this concept, read up on job stories, which help us understand people on a deeper level. In short, job stories help us explore a users’s circumstances, motivations, and expected outcomes. Getting in touch with users on this level is what creates raving customers.

People called millennials are no different. Their circumstances, motivations, and expected outcomes are different than yours, but that doesn’t make them nonsensical. You’re going to need to understand your target audience no matter what decade they were born in.

So, if you want to reach anyone in that age group, the first step is not attributing behavioral tendencies to all of them.

The second step is finding your target market within that age group by looking for problems you can solve.

It’s no different than traditional ways to find product-market fit—unless you bring an attitude of prejudice along with you. You’ll just need to have more conversations with customers, read more of what they read, go where they go, and validate your assumptions.

Write off an entire generation at your own peril. Millennials have a nose for businesses that do.

September 12, 2014 — 1 Comment — In Blog, Entrepreneurship, UX

There’s a business model that gets more glamorized than others, no doubt because it’s more interesting to read about than the alternatives. It goes something like this:

  1. Bootstrap an MVP (Minimum Viable Product)
  2. Try to get funding with MVP
  3. If no funding, bootstrap the initial product
  4. If funding is in sight, get as many customers as possible
  5. Hope that funding, product/market fit, and revenue align before one runs out
  6. Scale or sell later

Since this model is so interesting to read about, popular tech news is littered with “funding success” stories. We can easily begin assuming that this approach to success is the standard.

I have absolutely nothing against this approach, but it does start to skew our perceptions, making it difficult to know how to create our own pricing and customer acquisition models.


I read this laughably obvious article on why charging something like $5/month is unsustainable. The author isn’t pretending to have discovered anything groundbreaking, but it’s a good example of how we can get used to sub-$10 monthly payments for services that are valuable and expensive to run.

How are other companies charging next to nothing, and why?

It goes back to the model above. When a company gains enough momentum to get to step #4 (get as many customers as possible), the goal is customer acquisition—not creating a sustainable business model.

There’s nothing wrong with that, but if you’re not eyeing funding or being acquired, you’ll usually have to take a different approach. We can call this approach “charging more money”.


All kidding aside, you can’t just make a competitor in a product space, charge more, and wish for the best. I get that. But, bootstrapping a business has its advantages, and it’s possible to get there with patience and clarity.

Here are two different approaches I’m a part of:

B2B Foundation

The concept behind has always been to connect music lovers with new and forgotten music. And there’s always been a community aspect to it, as it’s designed to focus on your social friends, and we actively encourage supporting bands and local record stores (which our target audience—ourselves—pretty much do anyway).

As such, we realized a couple of years ago that we didn’t just need to do work from the customer angle. We needed to work with local record stores to understand the community better. Long story short: in pursuing and building a relationship with them, we were able to take work we were already doing and use it to build an ad platform that saved them money and brought us revenue.

We’re in a sustainable place to pursue further components that give value to record stores, while also being able to take our time developing the consumer side of things. We’ve started earning the trust of important people in our “market” by being, y’know, trustworthy. And this means we’re in a good place to help an entire ecosystem, instead of continuing to iterate on products that are built in a vacuum.

Need more encouragement? Consider how many mobile app developers are running unsustainable businesses while not pursuing the “enterprise”, which pays more (source).


We consider those record stores to be partners. Because partners deserve respect, we spent a nice chunk of money (before we had revenue) formalizing our arrangement with a contract. We took it seriously, because asking for peoples’ time is serious.

Partnering with smart people has paid off more than just about any of our early coverage in high-traffic tech blogs.

With Evermore, we’re taking a similar approach with partnering. Since we’ve chosen pricing that’s actually sustainable for everyone—while still providing enormous value to the right customers—it’s more difficult to PPC our way into more revenue. Instead, we’re partnering with individuals and companies who could benefit by having Evermore to refer people to.

Think of agencies that have an overflow of requests with low budgets, or public speakers who get asked how to build an online presence. We’re choosing to partner with them (and pay them a decent commission) to make it easy for them to refer people to a quality product.

We’ve chosen to focus on these partnerships over simple affiliate marketing for the same reason we won’t price unsustainably low just to acquire customers. It’s unsustainable, and we’d rather bootstrap it with the future in mind. It is slower, but we also don’t have to waste our time with scaling up for people who won’t stick around, or with not knowing how many customers will stay when we inevitably raise prices.

(Side note: get in touch if you want to learn more about being a partner.)

Both of these approaches are probably slower than the sexier, fast-paced customer acquisition model. You will need patience.

In my experience, though, the payoff of less stress, better customers, and more impact is worth the wait.

July 25, 2014 — Leave a comment — In Blog, Business, Entrepreneurship

A few years back, I heard a dude named Andy Stanley speak on leadership. He said something that stuck with me like few other teaching points ever have:

“Your responsibility is to empty your cup. It is not your responsibility to fill someone else’s cup.”

Honestly, I hate the cliché of having a pivotal moment while someone is talking about being a leader. I’ve got mental walls up against it. So, the fact that this permeated then and still sticks around today is impressive.

The idea of what my responsibility is as a leader (i.e. expert) began to shift after hearing that. As I thought more about it, I realized that focusing on “filling someone else’s cup” was actually too self-focused.

Trying to take responsibility for outcomes that truly can’t be controlled is a fool’s errand.

Any time someone else is involved, no one actually has control.

And, wouldn’t we all agree that other people have to be involved in any situation in which we’re making an outward impact?

I realized the best way I could help people is by understanding where my impact can begin and end.


When I started working with WordPress, and got pretty good with it, what I wanted more than anything was to be respected in the community. Honestly, I wanted people to know who I was, because, I thought, “How can I have have any impact unless I have respect first?”

There are two huge issues with tying your success to respect:

  • It’s not measurable, so you never actually know when you  have it.
  • Even if you try to measure it, you’re putting others in the position of informing you you’ve accomplished your goal.

Want to be more helpful in a community? Measuring it by the amount of respect you think you get is a cop-out. And, it will encourage you to give based on the perceived worth of the other party. If you’re trying to get respect, won’t you want to be helpful in front of the people you perceive as most important?

Bail on that. Don’t add a layer of abstraction on top of helpfulness—because that can be measured.


I’ve been trying to integrate the perspective of what Andy said into the way I help others for some time. Part of being helpful involves clear communication. So, when folks come to me with questions (which are usually about WordPress), I do my absolute best to help them in whatever manner I’m able, regardless of whether they’re ever going to pay me money or not. Regardless of who they are.

But then, it struck me this week that helpfulness could be quantitative for the purpose of self-improvement. It had to hit me over the head, because in the span of a few days, I:

  • was asked by two developers I respect to give my thoughts on their projects.
  • saw obvious progress from another developer I’ve been helping learn WordPress.
  • sent pull requests to multiple plugin developers to help them out.
  • had feedback be well received by WordPress business owners.
  • showed off someone else’s plugin for a client instead of taking their money and not mentioning it.
  • impressed that same client with WordPress’s ability to be integrated with API’s.

I realized, finally, that the hard work I’d been doing to be helpful was finally paying off. I’ve become helpful to people. I don’t know if they respect me or my domain knowledge, but that’s actually inconsequential. I’m doing what I always wanted to do: be a trusted resource in the WordPress community.

It doesn’t matter who knows my name or doesn’t, because the people who do aren’t afraid to ask me for input. That’s what I wanted all along.

Don’t measure your value to a community as a whole by your perceived respect in it. Measure your value by the frequency with with you help others accomplish their goals.

I don’t know if nice guys truly finish last or not, but I do know that it only matters if you’re in a race.

July 11, 2014 — Leave a comment — In Blog, Business, Entrepreneurship