Patience is a virtue, but in business, it can also be a weakness.

Entrepreneurship is often about finding balance. If you're building a product, it's understanding the number of features you put into a major version to make it newsworthy, versus causing too much confusion. Or, if you're in services, you balance the time you spend with each client so that you maximize your time, but the client doesn't feel ignored.

Opportunities are briefly open doors. If you don't walk through them when they're open, they could shut, and you'll be locked out forever.

The trick is to always be on the lookout for these doors, and to take advantage of proper timing. Those that do this more often than not end up winning in their respective markets.

If You Move Too Slow, You Lose

When I'm working with my clients, I always stress the importance of having a sense of urgency. If they have a good idea, they need to execute. Otherwise, it could be too late (for a variety of factors).

If you move too slowly, your competitor may beat you to the sexy new feature.

Or, you may enter into slower sales months around the holidays, and your message isn't heard.

Or, your competitor has their own release, and they make more noise than you.

I could go on, but the point is that you can only control your timing and nothing else. If you keep waiting, you keep losing future business.

"Never put off today what makes you money tomorrow!"

Money isn't everything, but it's the solution to many issues. Putting off competitive initiatives for too long hurts your ability to grow your business. I think at its core, we understand this as entrepreneurs. But why do we do it?

If you have some level of success already, then a large part of that can be attributed to being in the right place, at the right time. While this sounds like luck (and it is on some level), the reality is that you increased your chances of being in that right place at the right time by the sense of urgency you had in the ideas you implemented.

But then something changed. You got comfortable.

I've been guilty of this, too. It's easy to achieve a comfortable level of success and then slow down too much. Taking a more measured approach is well and good, but it's very easy for this to slip into a form of laziness. You already have predictable income for the business, so you don't need to “rush” anything, and as a result, you miss the timing.

Move Fast, Stay Sharp

If you're reading this, it's probably because, deep down, you know you've been moving a little too slowly. Maybe you've convinced yourself that you're being “strategic” or “waiting for the right moment”, but more often than not, that moment never comes unless you're the one to create it.

Success doesn’t wait around. Neither should you.

The best businesses aren’t just the ones with great ideas, they’re the ones that act on them quickly. So whatever it is you've been sitting on, such as a new offer or campaign, you need to move now! Get it out into the world. Iterate if you must, but don’t wait for perfect.

Because in business, speed doesn't just matter. It wins.

#entrepreneurship

I wrote 36 blog posts this year - here are the most popular ones.

Writing has always been a form of therapy for me. I enjoy the reflection, the physical process, and just documenting my experiences for future reference. I write about topics ranging from personal events, entrepreneurship, WordPress, mindfulness, politics, health, and happiness.

As you would expect, some posts are more popular than others. Below are my five most popular posts in 2024 based on number of views:

1. Matt vs WP Engine: Too Far?
2. WP Business Mistakes
3. Blogging Alternative to WordPress
4. WordPress Pricing
5. Winning in WordPress

Occasionally I write on Medium. Here are my top three articles this year:

1. How to Grow from $1M to $2M ARR
2. 6 Profitable Lessons from My Startup to Exit Journey
3. Pricing Strategies That Work

Stay in The Know

While I often blog, I don't always email my list. I try to limit it to just one email a month, sometimes two. And these are typically my better posts, not my personal ones where I'm documenting my life.

If you're not already, then you can subscribe below. I don't spam my list, and I value your privacy (there is no email tracking).

Also, if you're up for it, let's connect on Bluesky!

Have a great holiday!

#WordPress #entrepreneurship

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