The more I don't think about software, the more ideas that start to creep into my mind.

It’s funny, when I’m not thinking about starting a software company, I start getting flooded with ideas. And since I’ve started coaching founders, I’m getting more of these ideas.

A few have come up that are pretty damn good. Or at least I am interested in them because I really like the industry, which is the e-learning and online course space. This is a market that I have been involved with my entire career – even before my foray into WordPress.

But unfortunately, that’s a problem.

Why is it a problem?

I am still bound by a non-compete clause after the sale of LearnDash, and that restriction doesn’t expire until 2026.

If I wanted to move forward in the e-learning industry, I would need to seek legal permission from LiquidWeb. Maybe that makes sense at some point, but for now I’m pretty content just continuing with my coaching. At the same time, I can start doing some more market research to see if any of these ideas actually have potential.

#entrepreneurship

Through my business career, I’ve had the pleasure to meet so many smart folks. Many of whom I now consider friends.

Matt Medeiros of The WP Minute is one of those people.

Matt and I have known one another for many years, mostly interacting online, but occasionally in person. I respect the hell outta Matt and what he does. He has great perspective on business, life, WordPress, software, and services. Plus, I just think he’s a cool guy.

Earlier this month, Matt invited me to be on his podcast, The WP Minute. At the end of this post, I have included the recording.

Key Takeaways

• I explain how I am now selling GapScout after running into challenges building complex AI technology and changes to review site terms and conditions.
• The GapScout experience left me feeling defeated but taught me to focus on what really energizes me in business.
• I have transitioned to coaching for founders, playing to my strengths in marketing, growth strategies and maximizing profits.
• I am being selective about who I work with through warm outreach and relationship building vs trying to scale massively.
• For WordPress entrepreneurs, takeaways are to focus on your strengths, cut out parts of the business you dislike, and be selective about services you realistically can deliver at a high level.
• I have been using Medium for content marketing and gets great organic reach without having to worry about blogging or SEO.
• Overall, it’s a story of reinvention, lessons learned from failure, and the importance of playing to your strengths as an entrepreneur.

#entrepreneurship

Short and sweet this Friday.

A couple of weeks back, I announced that I was taking on coaching clients. To be honest, I didn’t know what to expect.

Fast-forward to today, and I’m working with founders across a variety of industries on their businesses. It has all been moving so quick, and I’m loving every second of it!

Up until now, I’ve just been sending a Google Doc outlining my service. That worked, but I figured it was time that I get a website up to explain everything.

Take a look: BrightGrowth

And If you’re interested in having me on your side to grow your business, then go ahead and book some time!

#entrepreneurship

Your brand is just as important as your product.

In digital business, every detail, from pixel to prose, matters. Crafting a brand that resonates isn’t an added luxury, it’s the foundation.

From a foray into online education to dabbling in software, my learning has always been clear: Effective branding can be simple.

When I coach founders, I am often asked is which strategies work best to get more customers in a crowded market.

Well, this article will answer that question.

Let’s dive into the actionable tweaks that can deepen your customer connection and enhance your brand’s recall. This isn’t theory, folks. I’ve used these exact strategies for gaining impressive amounts of market share.

The Power of Consistency

Imagine you’re reading a book, and in the story, the protagonist’s personality changes every few chapters. Confusing, right? How could you ever get into a story like that?

I’ve found that founders make this same mistake. Their brands often mirror this inconsistency when their identity keeps shifting. Consistency, I learned early on, isn’t about stubborn rigidity but about establishing reliability across all channels.

In the world of digital products, whether it’s software, an interactive online course, or an ebook, consistency will always be critical to your success. This isn’t just about having a visually appealing visuals. It’s about ensuring that the core of your brand remains the same across every touchpoint. It’s the little things, and these little things add up!

For example, let’s talk visuals (since that what most founders tend to focus on). Colors, designs, and graphics aren’t just artistic choices — they’re statements. Each hue, each gradient, each font choice carries a weight of its own. And consistency ensures that this weight is balanced throughout.

Then there’s the tone. How does your brand sound to your potential customers? Is your tone formal, casual, or somewhere in between? Your brand’s tone should remain recognizable across all channels. From your YouTube videos to the welcome emails.

Keeping track of all these things is tough, so I recommend that you create a brand guideline. Don’t worry, this isn’t a huge document. Keep it simple and focus on specifying your color choices, typography, and tone. This way, whenever you create a new asset for your business, you can pull it up just to make sure it’s all remaining “true to brand”.

The Art of Storytelling

Stories are what make us human. And your brand, beyond its digital facade, is profoundly human. It’s a tapestry of ambition, vision, and journey. Every digital product you see isn’t just a tool, it’s a testament to someone’s dream and determination.

So, what’s your story? It’s essential to articulate it, not just for your audience, but for yourself. Was your brand born out of a gap you observed in the market? Maybe it was a series of events, some eureka moments, and a few sleepless nights? Or perhaps, it was a dream you nurtured over countless cups of coffee?

Once you’ve identified your narrative, the next step is weaving it in a manner that resonates. Not every tale is epic, and that’s its beauty. The little detours, the unexpected roadblocks, the small joys — they add layers of authenticity to your brand narrative. Remember, it’s not the grandiosity of the story, but its genuineness that strikes a chord. An authentic tale, told from the heart, bridges the gap between a brand and its audience.

Engage, Don’t Just Broadcast

Think of the internet like a big, noisy classroom. Everyone’s trying to get a word in, and it often feels like a shouting match. Some people have big voices, so they carry further. Yes, they can be heard, but it’s annoying, right?

Don’t be annoying.

Here’s some advice from someone who’s been through it: instead of shouting louder, try a different approach. Don’t talk at people, talk with them.

You see, there’s a difference between just “shouting” your message and truly engaging with your audience.

For example, let’s say that you walk into a car dealership and without even a hello, the salesperson starts rattling off all the stuff they have, the prices, the discounts, and so on. It’s overwhelming, right? That’s just noise. They are sending out information, whether you need it or even want to hear it. It’s annoying, and you’ll shut down. It’s similar with those annoying chatbots and popups that people use on their websites. What is the first thing you do when you see them? You close it.

Same scenario, but picture this now: you walk into the car dealership and the salesperson greets you and asks for your name. They smile kindly, and simply ask you what you’re looking for, getting to know your needs. At this point, you’re likely to at least share your intentions. It has now become a conversation, a back-and-forth where you get to know each other.

From my experiences with software, online courses and digital products, I’ve found that true engagement is where you find troves of gold. It’s not about diluting what you want to say. It’s about saying it in a way that lines up perfectly with what your audience wants to hear.

Okay, cool — but how do you do that?

Here’s what I did. It works, you should copy it and put your flavor into the process:

1. Be Curious

Get to know your audience. Who are they? What’s their day like? What challenges are they facing? When you’re genuinely interested in them, you can serve them better.

2. Make It a Two-Way Street

When you post content, invite conversation. Ask questions, encourage replies, start discussions. It’s way more fun and useful when everyone’s involved. Do this in online chat, Facebook Groups, social media, and anywhere your potential customer is “hanging out” online.

3. Hold Interactive Sessions

Live Q&As, webinars, and AMAs (Ask Me Anything sessions) are awesome. They’re live, they’re real, and they give your audience a chance to chat with you directly. I crushed it with webinars. I didn’t do them often, but when I did, they were always a net positive. You can then re-use the content across multiple channels, like email, YouTube, and blog posts.

4. Value The Feedback

Yes, positive feedback feels great. But constructive criticism? That’s where the growth happens. It helps you see where you can do better. Every bit of feedback means someone took time for you and your brand. That’s big. Even the most scathing reviews have some important takeaways and represent an opportunity to demonstrate how you do, in fact, listen.

5. Show the Human Side

People connect with people, not faceless brands. Share a bit about your journey, the ups and downs, the behind-the-scenes stuff. It makes everything more real. When I was growing GapScout, I tried the “Build In Public” route. It was incredibly successful for building a following and list of potential customers. People gravitate towards authenticity and stories. Telling stories is about as human as it gets.

6. Stay Agile

The digital world changes fast. What works today is probably going to be old news tomorrow. Keep an eye out, adjust as you go, and don’t be afraid to try new things. Want a clear example? No one uses Facebook pages anymore for their brands. It’s moved to TikTok. Maybe you haven’t started a TikTok because you think it doesn’t make sense for your business, but I want to challenge you to get out of your own way!

7. Respond and Be Present

Engagement means being there, consistently. If someone drops a comment or sends a message, make sure you get back to them. It shows you care. And don’t carry a different tone between public and private comments. People are savvy, they’ll pick up on that, and it won’t sit well with them.

Small Changes Lead to Big Impact

The internet as a bustling marketplace. You know how some market stalls grab your attention because they have just the right lighting or display? That’s the magic of small details. Small changes, like tweaking how we present things, can make a huge difference.

In the online business world, it’s not enough just to be present. You want your ‘stall’ to be the one people remember and come back to, and you do this one intentional step at a time.

#entrepreneurship

Well, here’s an unexpected update for those of you who have been following my GapScout journey for the past year or so…

Summary: My heart is not into it, and after a lot of reflection, I have decided to exit the business. I’m currently working with some folks on a buyout and/or licensing. I have transitioned to offering coaching/mentoring to a select few founders (keep reading for information related to that).

Longer version: Software is fun, but it sucks, too. What I find most fun about it is building a brand, competing, and marketing. And since August 2022, I've been doing my thing from that standpoint, and it was working!

Through content marketing alone, it has gained a lot of traction! Thousands of visitors to the site each month, and 10-20 daily sign-ups for the email list, which has thousands of folks on it as well. Had some moments where it went viral on Reddit, too. People want what GapScout has to offer!

But the other side of the coin: software is emotionally draining. At least for me.

I encountered many hurdles over the past year. We overcame them, but each time it made me question... “why am I even doing this?”

I would lament these issues with my wife, Lorena, as I began to seriously question why I was choosing to have this stress in my life (she was incredibly patient with me).

Because that's the thing... it was a choice. I didn't need to be building a software company. The final straw came when G2 sent me a letter saying I couldn't analyze their very public reviews without a licensing agreement. At first, I thought, “Okay, no biggie, there's got to be a solution”.

I spoke with lawyers and with their legal team. Here's the thing: G2 (and similar sites) have been rewriting their T&Cs to limit AI analysis of ANY kind to protect their investors. It's insane. They can technically sue you even if you manually review the content on their site and document any themes or insights on a pad of paper. Like... what?!

Nonetheless, we found the solution, and that was to pay G2 (and similar sites) a licensing fee. They were cool with that, as you would expect. So, I was at a crossroads...

• Option 1: continue forward with the project, paying yearly fees to these sites.
• Option 2: back out now, and sell.

I took a few weeks to discuss with Lorena, and I landed on exiting the business.

I'm fortunate to have some options from that standpoint. One is to license the tech, another is to purchase the tech, and the third is to purchase the tech & brand. I'm confident that the end of GapScout will sort itself out in some capacity. I'm done stressing about it. The project had it's fun parts (i.e. marketing and growing the brand), but I’m moving on.

Okay, so what's next for me?

Something this journey taught me is to choose to spend my time doing whatever makes me happy. And something I've always been energized by helping other founders overcome challenges.

I have done this informally for years. It's fun helping others travel the path that I've already been down. I like to celebrate their wins, and help them get unstuck when encountering a roadblock.

When it comes to remote businesses (software, digital products, agencies, etc.), there are very few things that I haven't seen. I recently completed a coaching certification program to get some ideas on how to better structure my coaching so that it can yield positive results for clients as quickly as possible.

It’s exciting! I've only just started to let people know that I am taking on clients, and as of writing this, I have four founders officially signed-up. Several others have phone calls with me this week.

I just need a few more, and I'm closing the doors.

Why?

I'm the one doing the coaching, and I'm not trying to have a 40hr/week “job”. I want to show up with energy and enthusiasm so that I'm helping the folks I work with.

If you'd be interested in me helping your business grow, then email me, and I'll send you a doc outlining everything. Trust me, it's not your typical coaching process.

So that's the story and where I am at today. I feel like a weight is off my shoulders, which is how I know this is the right choice for me.

Finally, if I may offer a bit of advice. A key takeaway, if you will:

Always check-in with yourself. In life, in your job, in general. If you are powering through that “ball in the stomach” feeling, then take a minute to understand what is causing that feeling in the first place. Your current path might not be the best for you, and you have it in your power to make a change.

If you made it this far, thanks for reading!

#entrepreneurship

As a non-technical tech founder, I’ve always had to rely on a different skill set for starting a software company. I don’t have a huge following, so unlike content creators on YouTube, I lack any extensive reach when it comes to my entrepreneurial projects.

Whether you know how to code or not, perhaps you are in a similar situation, and so I want to share my methodology for starting a business (specifically software products, but it could be applied to any industry).

The premise is simple: start marketing prior to, or at the same time as, building the product.

This is the process I used when launching LearnDash, a company that I grew to over 42,000 paying users before selling. I am starting GapScout using the exact same process as I did a decade ago.

For years, I’ve been telling people to start marketing at the same time as building their product. I don’t understand why this advice doesn’t stick. Maybe because too many people have shared this tip, so it feels dated? Let me assure you that it works.

In 2012, I did this and built my email list to 1,000+ people before launch, a process that took about 10 months. It’s a modest email list size, but it helped me to be profitable and gain traction from day one.

It has been 10 months since I started a blog for GapScout (you guessed it: doing marketing at the same time as build, which is just a few weeks away from being done). And guess what? After 10 months of blogging, over 1,000 subscribers.

Here’s the thing: I’m not doing anything other than blogging, and the posts themselves are simply helpful content. Just do some really basic research on themes you want to rank for in your industry and start writing blog posts around these themes. Don't try to game the system or worry too much about how Google will rank your content. Just write blog posts:

• 1400 words minimum
• 3x per week
• Configure SEO (I use Yoast)

On each page of your website, have a sign-up form/call to action for when you launch. This is obviously how people sign-up to your list. That’s all.

This methodology works for many reasons, but mainly:

1. You get early traction. You can run special deals to start recouping costs and making money. Treat these early adopters well and they'll help spread the word.

2. New customers will come automatically. This is the most important part. My site now gets thousands of visitors per month from my blog posts. It feeds itself now, in addition to any other marketing endeavors I add (for example, YouTube).

After launch, make sure you communicate often to keep the buzz alive about your product. Announce ever update that you do, share your excitement, and always explain how your product improves their life. Constantly emphasize this. Never stop. People need to be reminded all the time. Oh, and issue refunds promptly if that ever comes up. The easiest way to piss people off is to hijack their money.

Most of all, have fun. Don't overthink the process, enjoy the flow of everything, and be flexible as you learn along the way. Listen to customers, and they'll give you their loyalty. Don't hide behind email – use chat. Be accessible. People like to do business with people, not brands.

#entrepreneurship

When I started GapScout in August 2022, I wanted to try something different.

I had success with LearnDash, but my motivation for that business, and the online education industry as a whole, was different.

I landed on building in public.

This involves sharing more details about my journey in starting and growing a software company. I am finding it quite enjoyable, and it challenges me to go outside my comfort zone as well.

To date, I have been doing this primarily on Twitter, but plan to expand to YouTube as well.

Discussing the pros and cons to building in public.

This week, I got a chance to chat with my friends Devin and Matt.

The last time we were all in together in person was back in 2019. I have chatted with each individually since then, but not as a group. I really enjoyed catching up and “talking shop”. I always walk away learning something new.

Here is the replay of our discussion. We talk about the pros and cons of building in public, how to do it, and the results of doing it. If you are eager to learn more about this marketing strategy, give it a watch!

As a special bonus: enjoy my dad interrupting me in the middle of the discussion, even after I asked him not to interrupt because I was in a meeting. 😆

#entrepreneurship

Starting a software company has many moving parts, and an often overlooked part of the process is creating an attractive, memorable brand experience for visitors.

The previous GapScout website was created by me (and that’s not a good thing). I put together something that looked decent, and then turned my focus on building my team that would ultimately build GapScout.

Thankfully, that design is retired. I’m pretty pleased with the new look, both the logo and design overall.

I am not one for flash, and I think the new design conveys that the value we will offer is in the AI and data. No distractions, just the facts. Clean, simple, and effective – just like the GapScout software intends to be!

Speaking of which…

BETA program is almost ready.

It has been six months since I first talked about starting GapScout. I will admit, things are not as far along as I originally envisioned. My goal was to have a beta program open by now.

You would think I’d be used to slower timelines by now, having worked in software for over a decade.

But alas, that is the nature of this industry. I am an entrepreneur, not a developer. In the end, this is for the best because I can focus on the vision and not the execution.

Building an AI tool that can provide value (i.e. help people make better decisions and make more money) is no simple task. I am thankful to have incredibly smart folks involved with this project. They are smart, thoughtful, and don’t want to rush anything. I can appreciate that.

Something quite important to me is that our first version provides you immediate value. Yes, there are plans for additional value-adding features, but right from the start I want to make sure that people are happy using GapScout. That is my personal goal.

If you like the idea of having an AI tool at your disposal to quickly analyze your business, your competitors, and your market for quick wins and in-depth insights, then invite you to become a beta tester!

#entrepreneurship

It has been roughly six months since I started the GapScout project, and I will admit, the delays in the progress have started to get to me a little.

On one hand, I get it. I am no stranger to software development delays. I don’t think I ever had a project finish on schedule if I’m honest. But at the same time, it is frustrating. This is particularly true because the current progress (as of this blog post) prevents me from really going hard with a pre-launch strategy.

Building business on a blog.

To date, all I have been doing is focusing on content marketing with blog posts. In 2012, I built LearnDash from a blog, so I guess I am just going back to my roots. I’ll admit, though, getting results from blogging today is a lot more challenging than it was back then.

From August through December, I made sure that two blog posts were being published per week. Each article is 1,500-2,500 words. The tone used is informative and the goal is to teach or help someone understand a business related concept.

At the end of the day, helpful content builds trust, and that’s my goal with the content created on the blog. It’s a simple formula, but one that I know can help drive revenue.

I have been using a “Pillar & Spoke” strategy that was first told to me by my good friend, Ross Johnson. The concept is fairly simple:

• Pick “pillar” keywords that are broader in nature (i.e. “Market Research”).
• Find related, longer-tailed keywords for that topic, called “spokes”.
• Link the spokes together, and point the spokes back to the pillar. The pillar then links out to the spokes.

Google likes this kind of linking, and it adds some extra “weight” to your posts in the eyes of the search engine. Well, that’s what we believe, anyway. Who really knows?

Upping to three articles per week in 2023.

Posting twice per week was working, but I wasn’t satisfied with the results. I felt as if the site should be getting more visitors and sign-ups for the beta release (which is currently the “goal” of the website that exists today).

So, starting in January 2023, I have increased the publishing schedule to three posts per week. It’s still early, but current signs show that just increasing to three times per week is having a positive effect. Traffic is up, and impressions are up as well. Just have a look at the upward trajectory that starts in the new year.

I will continue with this plan going forward, and I expect to see these positive results continue to snowball over time.

Key takeaways for your business.

Look, I’m not an SEO expert. Anything I know is because people way smarter than me have helped me out. With that in mind, here are some tips that I live by with the GapScout blog that, I think, will help you as well.

• Publish three articles per week.
• Write articles that are a minimum of 1,200 words.
• Use the pillar & spoke strategy outlined earlier.
• Share articles on social media (Twitter is quite effective).
• Use an SEO tool to optimize your articles (I use Yoast).
• Reach out to other related blogs for contextual mentions.*
• Be consistent, and patient!

*From what I have noticed, getting backlinks is still very much an important factor for building your presence in Google. Just a few mentions on reputable domains can really help boost your visibility!

This is my strategy. Nothing fancy. It’s working, but admittedly, there are probably things I could be doing that would make this more effective.

I will be sure to report back again this year on how things are going with the three posts per week. So far, I’m very optimistic with the impact that will have for the business.

Until next time!

#entrepreneurship

Allow me to paint a scenario…

You have passed the first six-months as a software startup. You have paying customers, and there is some buzz around your product. Your customers are pretty happy, and surprisingly understanding to the fact that your product still lacks some functionality compared to the competition.

Naturally, you want to repay them for their dedication and trust. You want them to know that you are listening to them, so you decide to publicly publish your product’s roadmap, so they can see what you are working towards.

They are happy, and you are energized. Everything is good!

The truth is, product roadmaps can be helpful in the first year of business, but then become a liability.

In the early years of a business, product roadmaps are a good way to get (and keep) people excited about your software, but at the end of the day, they do more harm than good – particularly in competitive markets.

When I was running LearnDash, I used to always look at my competitors roadmaps to see what they were working on. It gave me insight into what they (and their customers) thought was most important.

But here’s the thing. Occasionally, there were times when I would swipe their ideas and get it to market quicker. In the process, snapping up more market share and tempting their users to come over to my product.

Any worthwhile industry will be competitive, and public product roadmaps are the equivalent to showing your competition your cards before you even play, giving them an opportunity to play their hand accordingly.

Public roadmaps can frustrate customers.

I think most entrepreneurs think that having a roadmap available is a way to give customers confidence in the direction of the business. It shows movement and dedication. This is certainly true to a degree.

But what is often overlooked is that the roadmap can also be a source of frustration for customers. This is particularly true if it does not include features that they really want or believe are necessary. Worse, they may disagree with the entire direction and think that you’re out of touch with the market.

I know this to be true because I experienced it first-hand. I once had a roadmap where I shared the development priorities. For a while (during the first year of business) it was a value-add. However, I noticed that people would write into support increasingly frustrated with the roadmap.

From what I recall, the complaints fell into one of the following areas:

• They wanted a certain feature that was not on it.
• They thought it was taking too long for features in development.
• They didn’t think it was being consistently updated.

I noticed that the more vocal critics would often cite the roadmap in their public complaints, which meant that I had to jump in and “defend the roadmap” at times in lengthy back & forth conversations. Both sides getting more and more frustrated.

This experience made me realize that the roadmap had a negative impact on the business and just gave any customer who was already annoyed fuel for their fire.

So, I scrapped it and immediately didn’t have to deal with any of that BS anymore.

Customers hardly noticed its absence.

Product roadmaps are a distraction.

Look, many folks love having a roadmap for customers. If it is working for them, then that’s great.

But they aren’t necessary. In fact, they are more often a distraction for both you and your customers. They also give your competition some incredible insights.

So, if you never had a roadmap and feel like you need to add one, then I’m here to tell you that it’s okay to bypass it and just focus on more important parts of your business.

#entrepreneurship