🌐 Justin's Blog

entrepreneurship

Ever since I was around 18-years-old, I have been trying my hand at starting new businesses. I recall coming home after my first semester of college and working over the holiday on a website and info product. I loved every second of it, but I was beyond naive.

As you would expect, nothing came from that effort. I went on to fall for pyramid schemes, bought an endless number of info products on making money online, and started countless other projects that never went anywhere.

I look back fondly on this time because with each effort, I was learning something new that would help me later in my entrepreneurial career. I got practice building a website, honing my sales messages, networking, blogging, and building a brand.

During the summers of those university years, I worked as an intern at a large company creating e-learning, which actually was the beginning of a lucrative career path. I had a cubical and wore the “uniform” (dress shirt & pants with a key badge attached to my hip). I was there to learn the ways of corporate America.

Except, I was hardly doing work.

I would spend my eight, long hours searching the internet for business opportunities and brainstorming ideas. When my boss would walk by, I’d quickly pull up my email or some random Excel document. My dad used to ask me how my days were going, and I would tell him about all the businesses I wanted to start. It drove him crazy!

While I put in the bare minimum regarding the work, my internships did teach me something: I learned that I did not want a corporate career.

Eventually, I had my first taste of success.

None of my projects produced any money. Maybe $5 here or there, but nothing substantial.

That changed when I was in grad school.

I had already secured a job with Accenture, but I still had another semester to go. I was in bed one night. I think it was around the beginning of February. It was dark outside, with snow on the ground. I was about to fall asleep, and it hit me…

Free domain names!

Ha, it’s funny to think back on this now, but I was convinced this was a revolutionary idea at the time. I mean, who wants to pay $10 or more for a domain when you can get it for free, right?? 😆

The business model was pretty simple:

  1. Get someone to tell me the domain they want

  2. They sign up for CPA offer

  3. I got paid a commission from the company, and used it to buy their domain name

I found someone to build my website for $300-500, then used Dreamweaver (remember that?) to make edits as needed. On the homepage, I had a field where someone could enter the domain that they wanted. This field would check to see if that domain was available, and if so, a button would appear for them to register.

Sounds basic, but in 2008 this was super slick. It was very “Web 2.0”.

Even though I was pretty familiar with WordPress at that point, I started a blog on Blogger instead.

My blog posts were bad. I mean, terrible. They were mostly all about self-promotion. No images or anything engaging, just short 250-word blog posts.

But the real magic came with… wait for it… MySpace.

Yes, you read that right. MySpace.

There were chat rooms on MySpace for various interests, one of them being business and entrepreneurship. I would participate in those chat room (most of the time, it was people just sharing their MLM programs).

Through the noise, though, there were folks who were looking to set-up their own website. Of course, they needed a domain, so I would chat with them.

My efforts paid off. I made $40-$120 per day with this strategy, and it was only the first month or so!

As you can imagine, I was pretty freaking excited! I had a job waiting for me in consulting after grad school, but I was seriously thinking about going all-in with this new success. Success that I finally achieved after so many years of trial-and-error.

So, I kept doing my thing, making good money by just sharing with people my new business. All was good in the world. I had my taste of success and a ton of confidence.

But I came crashing down from my high when payouts were due.

Reality hit hard when the company that was giving me the commissions nullified about 85% of them, which meant that I actually was operating at a loss after buying the domains for the customers!

Ugh…

It felt like someone punched me in the stomach. I called the CPA network and tried to reason with them, but it was a lost cause. They said the leads I had produced were not “high quality”. So, the business was sinking before it even had a chance to begin. I was only a few months away now from starting my consulting career.

In the end, I configured the site to use another CPA program that would pay me per email lead ($1 per email). It made about $300/mo passively. After three months, I sold it for $3500 on Flippa. A small success, but not the one that I had hoped for.

Reluctantly, I started my consulting career. It paid well and had great benefits, it just wasn’t what I wanted. That said, I was doing e-learning consulting and I did enjoy that industry. Little did I know it would translate to me finally achieving my dream with LearnDash.

Entrepreneurs never fail, they just learn.

I’ll admit, the side hustles that didn’t work out felt like failures at the time, but now that I have more perspective I see that these were not failures but rather lessons learned along the way.

True entrepreneurs never stop. We keep trying. There is a burning desire that cannot be satisfied by a normal 9-5 job. I kept trying, taking the tactics and lessons learned from previous endeavors with me and applying them to new ones until it all came together: my interests, skills, and market timing.

Because that’s the thing… if you never stop, you’re bound to get the timing right eventually. There is not a single entrepreneur out there who found success on their very first attempt. I tried countless times until finally getting it right.

Now that I have had experience with LearnDash at all parts of the business process, I am taking those lessons with me as I start GapScout. Entrepreneurship is about continuous improvement. Learning from past mistakes, and then using those experiences to be better.

#entrepreneurship

When I was in middle school, my principal used to say:

“The hardest part about any project is starting it.”

I had this in mind when starting GapScout, my second foray into the world of software, but first as a traditional SaaS. I learned a lot during my time building (and selling) LearnDash, and I can't wait to apply those learnings to this new venture.

One of those lessons learned was building an audience before and during the build process. For that project, I started content marketing 10 months before the product was built. I built an email list, got a good solid footing in Google, and was able to build buzz. This made the launch a success.

For GapScout, I am using this same formula (except we won't have to wait 10 months for launch this time)! 🙂

The content marketing strategy will be taking place at the same time as product development. I tapped my network and was introduced to a couple of content marketers who will be helping me in this area. As always, I like to start out with a few trial articles to see how things go. So far, so good for the both of them!

Smart content creation is just the first step.

I’d like to first build a solid footing in Google (seeing as this is a brand-new site), at which point I will begin the outreach process to start building relations with bloggers and websites in the same niche.

When you start a business, it's not always about the “big milestones”, it's nice to recognize the smaller achievements along the way.

Recently, the GapScout website celebrated one month. While developer conversations are happening in the background, the content marketing has started to make progress. There is no “hack” for content creation. It's a slow, long process. But it pays off!

In 30 days, the GapScout website has seen 2,083 unique visitors.

No secrets, just keyword research, writing quality articles, and sharing the content on the normal social channels.

I do intend to use paid ads as well, but not quite yet, as I'd prefer to do that when there is a product ready to use. So for now, the content marketing approach will continue, it definitely is paying off.

Want early access to GapScout? Get on the early adopter list!

#entrepreneurship

Well, that didn’t take long.

Closing in on one-year since the sale of LearnDash, and I am jumping back into the software industry. This time, with a micro-SaaS as opposed to WordPress.

I’ll discuss a little about the why, but first let’s talk about what.

Meet GapScout!

In a sentence, GapScout is the easiest way to identify the profitable gaps in a market. It does this by analyzing reviews of your product or service and highlighting common themes & opportunities.

Reviews are a goldmine for a business. Not only your own reviews, but the reviews of your competitors as well. They can reveal desired features, opportunity areas, and influence your sales messaging so that you are saying the right thing, to the right people, at the right time.

From experience, I can tell you that sifting through reviews and knowing what to look for can be confusing and time-consuming. Especially if you are a solopreneur or a small business. GapScout systemizes the process and does the heavy-lifting for you. All you need to do is decide which action to take with your newfound insights.

When I was running LearnDash, I was constantly keeping an eye on the pulse of the market. What people were saying about my product, and also my competition. As a result, I was able to:

  • Improve my current offers
  • Find new opportunities
  • Spy on competitors
  • Improve sales copy

This was my secret sauce. I know it works, and I am excited to be building a solution that lets others benefit from it as well.

Sounds cool, but why start a software company (again)?

When my role with LearnDash ended, I was able to catch my breath. I’ll admit, I was a little burnt out from doing software (especially, WordPress). As I searched for inspiration outside of tech, I was originally attracted to land investing. Truth is, it’s something I’ve been interested in doing for a long time.

I was just about to pull the trigger on my business (everything was set up), but I stopped. Something didn’t feel right. I don’t know how to explain it, but I knew that I needed to pump the brakes again for some more self-reflection.

I realized that what energizes me the most, what I love to do, is to compete. To think creatively, to give people tremendous value, and to try to “win” in the game of business. The absolute best place for me to express this desire has been in software. It’s fun for me, but only if I believe in the software that I am building & selling.

I feel this way with GapScout. I completely believe in the value it can provide solopreneurs and small businesses selling services or products. I can’t wait to help people make more sales!

Even though it’s only the beginning of this journey, the response I have been getting from folks has been overwhelmingly positive. They want this product, and I’m excited to bring it to fruition.

If GapScout sounds cool to you, and you’re interested in getting early access, you can sign-up here. An early, pre-beta phase is targeted for the October/November timeframe.

Also, I am building GapScout in public, so if you like occasional updates, then follow me on Twitter as I post insights into the process there frequently.

#entrepreneurship

The revenue engine behind most companies is renewal income. Be it a food delivery service or software, compounding renewals is what helps move up your bottom floor up year-over-year.

But the thing that many entrepreneurs don’t realize is that the process of selling customers on your product initially is different from selling customers on the renewal purchase. In theory, selling an existing customer should be easier than getting a new one, but only if you do it right!

Emotional Messaging vs. Validating Actions

I really enjoy the process of positioning a brand. It was my favorite part of running LearnDash, and I got pretty good at it.

What I enjoyed most is that it forced me to be creative, discover gaps in the market, and create messaging around emotional triggers that get people genuinely excited to make a purchase.

But if your product has a renewal (you should), the sales validation process is different. Specifically, you need to move from emotional messaging to validating by actions, and the best way to do this is by:

  1. Making customer requested improvements to your product.

  2. Effectively communicating these improvements.

Making continual improvements to your product is a given, but you should be thinking about two audiences with these efforts: new customers and current ones.

New functionality designed to bring in more customers is a natural part of any marketing strategy. To remain competitive in a market, you need to be current with the latest trends. This is where you use your intuition to develop (and position) your product accordingly.

Features that you develop for current customers are not a waste of time or effort. In fact, these kinds of releases are more beneficial than features designed solely for bringing in new customers. If you please your current customers, then they are more likely to give you that word-of-mouth marketing that companies dream of, and that is way more valuable than any paid ad campaign.

But aside from this benefit, creating functionality that your customers ask for is a surefire way to keep them around.

Look, there are an endless number of software solutions available today. Some are dirt-cheap, so competing on price isn’t going to get you anywhere.

What does get you somewhere is your responsiveness and willingness to hear out the use-cases of your customers, and then use those drive a portion of your development. This reinforces a customer’s initial decision to purchase your product (people hate to be wrong). It shows them that you are committed to them and their success.

You Need to Bring the Hype!

More important than anything (and I cannot stress this enough), you need to over-communicate what it is you are doing, specifically why it matters to your customers.

This is where most businesses get it wrong.

They listen to customers and develop “crowd pleasing” functionality, but then they suck at getting the word out about it. They fire off an email and that’s about it. I mean, if you do the bare minimum, then expect a bare minimum response.

While it’s not necessary for every release you do, at least once a quarter you should be building a robust marketing hype train with your new releases. Things like:

  • Teasing the new functionality on social media with screenshots.
  • Creating pre-release videos to share with customers.
  • Working with your affiliates to notify them of the new functionality, why it’s good, and how they can spread the word.
  • Doing live webinars to show the new stuff in action.
  • Creating a release blog post and video(s) to show it all off.
  • Holding post-release webinars to demonstrate further.
  • Sharing case studies with the new functionality in action.
  • Running re-retargeting campaigns.
  • Having a limited time sale in conjunction with the announcement.
  • Emailing people who didn’t open your initial email (several times).
  • Contacting folks who let their license expire and give them a limited-time discount to jump back on board with your product.

Honestly, the above is just scratching the surface on what you should be doing. If you’re excited, that will get other people excited. You show people you are excited by making a lot of noise, plain and simple.

Keep your current customers excited, and they will reward you by sticking around.

The excitement you generate with your releases translates to new customers (because of the hype) but it also shows your commitment to existing ones.

When their renewal hits, they’ll remember that you keep giving them a return on investment. You’ll be giving folks FOMO if they don't renew. People who let their account expire will jump back on board (you should be emailing old customers about the exciting stuff you’re doing).

You need to over-communicate.

You need to beat your own drum and never stop.

Remember that you are competing with an infinite number of other options out there — it pays to be the loudest one in the room.

#WordPress #entrepreneurship

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If you are like most people, then at some point in your life you have considered owning real estate.

Even people who don’t consider themselves to be entrepreneurs find real estate an attractive concept because it’s an easy business model to wrap your head around. Own a couple of low-maintenance residential rentals and let that other person pay off the mortgage while building equity.

Sounds great on paper, but as anyone who does this will tell you, things don’t always run smoothly.

I just need to look to my parents. During the recession of 2008, they purchase a few foreclosed condos. They are in a nice area with low crime and good schools. Even still, there is constantly something to be taken care of. Like the time their renter was literally stabbed by their crazy ass ex-husband, and was late on the rent by a few months because of the whole ordeal. I mean, there isn’t a book that can teach you how to deal with that.

When you peel back the onion, the reality is that real estate is not for the faint of heart. While it’s a great way to build wealth, it is not passive by any means. Depending on your property and the person renting, you may end up sinking insane amounts of time and money into the property to the point where you barely break-even.

I want to build wealth in real estate, but I prefer not to deal with the bullsh*t of having renters.

Upgrading appliances, fixing sinks, evicting squatters… I don’t have time for this. Okay, scratch that. I have time, but I want to spend my time dealing with it.

Still, the idea of real estate is very appealing to me, especially as I am completely burnt out from anything to do with the software industry, especially WordPress. As someone who started and sold a software business, there is something therapeutic about owning physical real estate. Like, you can touch it. It’s real. You can actually see the asset. Most importantly, it’s proven as the world’s oldest way to generate wealth – be it for a side income or a financial empire.

So, for me, it’s land > rental properties.

That’s not to say it’s all rainbows and butterflies. Land has its ups and downs, like any industry. But what I find refreshing is that the business model is straight-forward, with less complexity than other profitable industries.

Also, land is less impacted by the housing market. It is a little as you can imagine, but seeing as banks don’t generally provide loans for land in the first place, it creates additional opportunity for seller financing of deals (which has an added benefit of spacing out capital gains tax on a short-term flip).

I have already got the wheels in motion for this journey. I started off by getting the legal entities set-up and the business presence. All the software I am going to use initially has been configured and is ready to go. I’m also taking courses and getting up-to-speed with the basics because I don’t have a background in this business. Though honestly, that’s never stopped me in the past.

If I know anything about my learning style, I am a “ready-fire-aim” kind of guy. Give me the basics, and let me start working it. I know that I’ll make mistakes along the way, but I don’t sweat those as I know it’s a learning opportunity (I made a crap-ton of mistakes when running a software company, and everything worked out just fine).

Want to learn how to make money from land investing?

If you find the concept of land investing interesting, and you don’t want to worry about renters or fixing sinks, then I encourage you to follow along as I share what I learn!

I won’t be writing about it here too much, as this is my personal site and I use it to write about a variety of topics.

I started a newsletter where I document my journey in building a land investment business from scratch – with no prior experience. Think of it as my online journal of lessons learned, from “hell yes” to “oh sh*t”, and everything in between. Things like…

  • The strategies I use to find deals
  • Business set-up & tools
  • Marketing strategies
  • Growing a team
  • Automation of tasks
  • Making money buying & selling land

I hope you follow along with me, I promise you will learn something along the way!

#entrepreneurship

I have been a blogger for a long time. Even before I started LearnDash, I wrote a blog while in college as I first became familiar with WordPress. Expressing myself through blogging has been a major part of my life.

So, when I first heard about artificial intelligence (AI) written blog posts, I sort of rolled my eyes. Many of you can remember the days of “article spinners” and the garbage output – half of the time they didn’t even make sense. I assumed the same for AI written blog posts and never gave them a second glance.

Until recently, and I must say, AI blogging is damn impressive.

I have spent a number of days the past week experimenting with a variety of AI content platforms to see the type of quality they would produce (finally landing on WriteSonic). My assessment is by no means scientific, but my best estimate is that most of the AI articles I created were about 60-90% complete. Meaning, most of the content is ready to be published without any updates.

To be clear, there were times when the articles were quite poor. This is most often the result of targeting a very specific industry topic that requires in-depth knowledge in order to write about it effectively. But I found that if I took it “up a level” to a more general topic, the quality of the content improved.

Herein lies the opportunity, and the method, in which you can use AI for your own content.

What you can expect with AI blogging.

If you rely on blogging as a core part of your business, then it can be challenging to come up with ideas and post structures regularly. This is where AI can help. When I use WriteSonic, I’m able to whip up outlines in about 30 seconds for any topic by just giving a few prompts.

For example, I put in the prompt Types of Mortgages, and got this outline:

Not bad, right? Honestly, this feature alone provides enough value for most bloggers. I should note that this is just one outline of about six that were presented after I gave my prompt.

This is just scratching the surface of AI content generation. Let’s say you wanted the intro written for you (just to kick things off). Well, that’s possible. Using the same prompt, I was presented with six intro paragraphs. Here is one:

Again, not bad at all! There are definitely some things I would change, but for the most part, it’s good to go and is a great intro to my article.

AI content is best when you keep the topics rather broad (in this example, “mortgages” is a pretty generic topic). If you drill down into a subject further, then you will find that the content isn’t as robust, with sentences that don’t really say anything. For example, I tried Paying off a Mortgage Early as the prompt, and the blocks of text weren’t so impressive.

This was the shortest of the six options presented. The longer ones weren’t any better. They all were essentially just a few sentences being repeated in different ways.

How you can use AI-generated content.

Undoubtedly, there will be people out there that use AI to write their entire blog posts, and without making any changes. It has to be said that the articles that are purely AI written are not the greatest. Even the best ones need a little massaging to sound more natural.

And that’s really the point. A natural sounding article is a good user experience that reflects well on you and your brand. If you are interested in using articles written using AI, then you owe it to the reader to do a little proofreading before you press publish.

If you’re anything like me, you’ll be impressed with the quality of your articles (and how quickly you’re able to complete them), making it tempting to just publish them as-is. But as my friend Jack points out in the tweet below, you’ll want to be approach this strategy with a bit of caution. Google doesn’t like this kind of content, and if they can figure out how to accurately detect it, they’ll penalize sites with AI content.

So if Google will potentially punish sites using AI-generated content, how can you use it?

Well, one option is to just ignore the threat. There are some major outlets using AI content right now (and they have been for years) – such as the Associated Press. Make some intelligent modifications to the core content, and you’re in the clear (…hopefully).

I am testing this “intelligent modification of AI content” method for my real estate investment business, but admittedly, content marketing is not a primary customer acquisition strategy. If the content was flagged in any capacity, then the business would still function fine. That said, I will admit that it would really suck to lose a potential passive marketing channel.

Another option would be to use AI to help you create an outline for your article, and then you write all the content. This is a conservative approach that should leave you sleeping worry-free at night, and is probably the best way to get started using AI. It’s especially powerful for helping you come up with a good sales page, or product description. Granted, it’s more time-consuming, but it will help you get through writer’s block, which will help you write more efficiently.

Finally, you can just avoid AI content creation altogether. That’s certainly a valid approach. If your business is 100% online, and you really rely upon content marketing for customer acquisition, then not using it is the safest way to avoid any potential penalty. Either write the content yourself, or hire someone to do it for you.

AI content will only get better.

Something that we all know about AI and machine learning is it continues to improve over time. I think this may start to create a cat and mouse game between purely AI-generated content and Google.

If I have learned one thing in my career, it’s that you don’t want to try to beat Google at their own game. So, while AI content will improve, I highly recommend that you don’t just use the content “as-is”. Humanize it with your own voice and expertise.

#entrepreneurship

One of the first times I was inspired to make money online was in the early 2000s, when I came across The Million Dollar Homepage.

The concept was simple: there were 1,000,000 pixels available for purchase at $1 per pixel. You could purchase a block of pixels and put your digital advertisement in that location. This kind of thing took-off in the early years of the internet, and as you can imagine, it was sold-out pretty quickly as it also garnered a lot of attention internationally.

The site is still available to visit today if you want to take a look, though be careful on which ads you click because who knows where they will take you!

The creator of this website was Alex Tew. He has since moved on to bigger and better, as evident by founding Calm.com, which generates ÂŁ150-200 Million in revenue per year.

All it takes is one idea to get started.

Alex’s story is not original by any means. He had a “flash-in-the-pan” idea, and leveraged that idea to then fuel future endeavors. In reality, many people would be happy with the results of his original million dollar homepage idea – it’s proof that just one idea can change your life forever.

I remember back in college when I had a few of my friends over for some drinks. We all got pretty buzzed, and one of my friends started talking about how if we could just come up with one idea, we would be set for life. He kept emphasizing how all it would take was one idea. Just one!

Hell, that should be easy, right? So, the rest of the evening, we all brainstormed what were likely terrible ideas before ultimately giving into the alcohol.

I don’t remember any details around the ideas we discussed, but I do remember thinking back on the entire evening for years to come. My friend was oversimplifying things a bit, but he wasn’t entirely wrong. All you need is one idea. So many people have made a fortune by finding an idea they believe in and making it a reality.

Thinking back on that evening with my friends, I see that we were all seeking more than one idea. We were trying to come up with one revolutionary idea. That was never going to happen, especially from us.

You don’t need a revolutionary idea, just a small twist on an already proven one.

Time can be a great teacher if you let it. I have learned a lot over the years about entrepreneurship, creative thinking, and bringing ideas to life. I have started a multitude of businesses that didn’t work out, but they didn’t “fail” because along the way I picked up new skills. Things like:

  • How to communicate value
  • How to use content marketing to build an email list
  • How to position a brand
  • How to sell

Through it all, I started to refine my skills so that the likelihood of my next idea being a success would be just a little higher. And eventually, my skills (and timing) came together when I started LearnDash.

Over the years, I have realized that there are very few original ideas out there. You don’t have to create an entirely new category, like Steve Jobs did with the iPhone. All that is needed is an original take on a concept that is already proven. This is particularly easy to do in software, but can apply to any industry.

How you can find an opportunity for your idea.

Most good ideas come from a point of user research. The easiest way to find a winning idea is to look at reviews of the products you love, and to document the common complaints. Then, create a solution that addresses one of those issues.

If you want to sell physical products, jump to the Amazon reviews to see what people are saying.

If you would like to sell software, go to Capterra or G2Crowd and do the same. In these reviews, you will find the profitable segments of very well established markets. No need to reinvent the wheel, just create a better wheel.

Of course, establishing product-market fit is only a part of the equation. It makes no sense to build something if you can’t get it in front of your intended audience. As such, my advice is to avoid building and start marketing instead!

"Stop designing and developing, and start marketing." - Me

Create a sales page that calls out the features & benefits of your product based on the research you did, then start creating content. Build an audience first. If your message is resonating, you will get people asking when your product will be available. At this point, you know you have a market, and also initial customers.

Ideas are inherently worthless.

As you probably already know, ideas are worthless. The value comes in execution and bringing that idea to life. If you have done your market research and know that it is viable, then all your energy should be spent in making your mission known.

Your priority in any business is to make money. If you are working on something that isn’t coming to fruition in the way you envision, don’t get discouraged. It’s not a failure by any means. Take your lessons learned and apply it to your next project.

It is only a failure if you stop trying.

#entrepreneurship

It's the easiest decision you'll ever have to make.

Can we talk about Black Friday sales?

Can we also make it the last time we talk about Black Friday sales?

Okay, good. I’m glad we are on the same page.

This article is the “be-all, end-all” for the discussion of whether you should, or should not, run Black Friday sales in your business. Next year, when this conversation comes up, just send this article to the person who is asking the question.

When you first start a business, you wear many hats, from janitor to CEO, and everything in between. You are the one to make the big, strategic decisions for the company, and then you are the person who has to implement them.

Smart entrepreneurs understand that they don’t have the answers to every unique situation, especially the first time around. As such, they often rely upon their network for advice on certain topics.

And inevitably, one of those topics is Black Friday.

I am a member of a few entrepreneurial groups (mostly around the WordPress space) and like clockwork, around October people begin to ask whether they should have a Black Friday sale. This then sparks lengthy discussions that go into weird directions, from ethics and capitalism to politics and cultures.

Whether you should have a Black Friday sale or not is an odd question, as the answer is quite obvious: yes, you should.

There is No Gray Area

It is incredibly stupid to not have a Black Friday sale.

For a few years while running LearnDash, I decided not to have a Black Friday sale, and I convinced myself that my decision was the right one using the same arguments I see others use today. I’m sure you have seen, or maybe even used yourself, one of these:

“Black Friday sales devalue our product.”

“It’s not fair to people who purchased before the sale.”

“It feels dishonest.”

“Current customers will get mad.”

“Current customers will want the sale retroactively applied.”

Every one of these statements is unequivocally false. If you think this way now, purge it from your head. You are wrong.

Whenever I see people present (terrible) arguments against having a Black Friday sale, I want to shake them to their senses. Though over time I have come to realize that this is just a “growing pain” that every early entrepreneur has to go through.

Look, I get it. I know that being an entrepreneur is hard. We are constantly faced with decisions, and the answers aren’t always clear. We are used to solving these complexities. But that’s not the case for this one, and this super easy decision will add thousands upon thousands of dollars to your bottom line, like it did for Maarten:

Maximize the Impact

My first year doing a Black Friday sale, I didn’t do any kind of promotion. I just threw up a site wide sale announcement on my website and slashed the price by 50%. Even then, it resulted in over four times the normal sales on a typical day.

Over time, I added some more elements, but I never went overboard with the promotion. At a certain point, it can have diminishing returns. Remember, the point of Black Friday is that you maximize revenue for very little effort.

Here are some tips for maximizing your Black Friday sale reach. These are the exact ones that I used to reach strong six figure Black Friday sales:

  • Offer 50% off – Anything less than 50% is a waste of time and isn’t enough to elicit impulse purchases.
  • Use countdown timers – Put a banner on every page of your website advertising the sale and include a timer for when that sale is over to create a sense of urgency. Important: include a button to your purchase page on the banner!
  • Create affiliate materials – Leading up to the sale, email your affiliates to let them know of the discount. Give them promotional materials like website banners, images, videos, and email swipes. Make it as “point-and-click” as possible.
  • Don’t offer lifetime deals – I won’t drain this topic, as I have written about it quite extensively already. The biggest benefit of doing a yearly Black Friday sale is that it will compound over time, assuming you have a yearly renewal.
  • Renew at full-price – Black Friday special pricing is for new customers, not existing. When renewal comes for these purchases, it should renew at the full price or close to it. Be upfront about this with your promotion and you’re all good.

Black Friday is a great time to experiment with your marketing in general as well! It’s the perfect testing ground to try out those strategies you have been thinking about implementing. My friend Joe Casabona did this and had his best Black Friday ever!

Black Friday is Not a Hard Decision

Many people overthink Black Friday. If that's you, then stop. It’s actually the easiest one you will ever have to make for your business.

The best part about Black Friday sales is that the world understands how it works. There is no educating people on what it means and why the sale exists. Consumers know they can get a deal on products, and that this deal is limited in time. They also know that the deals around this time of year are often the best deals ever offered by a company.

There is absolutely no need to apologize, feel bad, or feel like you owe something to those who purchased previously. If you feel this way, you are overthinking it.

Keep it simple because the reality is that Black Friday is exactly that: simple.

It is a win for your customers and a win for your business. My advice to anyone questioning Black Friday is to take the win, and put your energy into the real issues you are facing with your business. You can then use some of that Black Friday revenue to help solve it. 😉

At the end of the day, the best way to help your current customers is for your business to do well. The more money you make, the more you can do for those who have trusted you and your product. If you choose not to have a Black Friday sale, you aren’t doing everything possible to properly serve your customers.

Have the sale, and know that everyone benefits from it.

#entrepreneurship

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I don’t know when it happened, but sometime within the past three to five years, “lifetime deals” (LTD) for software really started to become a thing.

As a consumer, you love these. Pay a little extra upfront, lock-in the price, and never have to worry about paying again. The company gets a little extra money, and you get a lifetime benefit. Win-win, right? No, not at all. This is all win for the consumer. While offering customers a lifetime deal is tempting, if you ever want to sell your business, then you better avoid them.

Full disclosure: at one point, I gave a lifetime deal for my software, but it wasn’t really planned. Renewals weren’t a thing in WordPress back in 2013, so I didn’t really know anything different. The industry matured over time, and yearly renewals eventually became the norm.

The only other time I offered lifetime pricing was to satisfy my ego by selling LearnDash for $999 just to prove to AppSumo that I didn’t need to bother with their bogus pricing model after they wouldn’t stop bothering me about listing on their website. I sold ~20 in four days, then stopped the experiment.

All this is to say that the lifetime deal business model was never an intentional, long-term pricing strategy for me.

If you ever think that you one day you will want to sell your company (spoiler: you will), then you are doing your business harm by offering lifetime deals.

My friend Pippin Williamson sold his company the same week that LearnDash was sold. But before he made that big sale, he sold a single product from his portfolio. He wrote a blog post, and in it, he said:

All products and companies will ultimately always meet one of three fates: they will slowly fade away and die; they will be discontinued; or they will be sold or transferred to someone else to carry forward. There are no other possibilities. One of those three things will always happen.

Pippin Williamson Founder, Sandhills Dev

If you are a founder, then this will one day be your fate, too. Hopefully, you will be selling! That is far more fun than closing up shop. 😆

I will cut straight to the point: investors hate non-recurring revenue. I mean, you wouldn’t either, right? Let’s say you are looking to purchase a company and last year it did $2,000,000 in revenue and all of it represented lifetime deal sales. Wouldn’t that make you nervous? It should.

First, there is no guarantee that the following year will be better than the previous. With recurring revenue, that becomes highly more likely because of the snowball effect. Growth rules the day, always.

Second, the customers who made up that $2,000,000 can never be sold to again for the product they are using. Yes, in theory you could sell them a complimentary product, but there are no guarantees that they will want that product. Whereas, you know they want the product that they purchased the lifetime deal.

When I was selling LearnDash, I gave many management presentations to prospective buyers. Each one of them asked about the lifetime access that the earliest of customers had to the product (back in 2013)! They disliked it and wanted to quantify the loss of future revenues because of it.

Fortunately, the impact of lifetime licenses was so small at that point, it was not a major valuation factor for me. Still, I had to put their mind at peace about it. Had we offered those every year, I think those particular conversations would have been a lot more difficult.

While there are many reasons why you should not bother with offering lifetime deals, this is one that isn’t talked about enough. To be honest, I wasn’t even aware of this downside until going through an acquisition process myself.

Instead of offering a lifetime deal, think creatively about other ways to increase revenue while simultaneously delivering continuous value to justify recurring payments.

#entrepreneurship

LearnDash is now part of the Liquid Web family of brands, I learned a ton along this journey.

Selling my business was one of the most stressful and challenging things that I have ever done as an entrepreneur. In the end, it took just about a year from start to finish (October 2020 – September 2021).

If you’re interested, you can check out the official announcement on the LearnDash blog, or check out Liquid Web’s press release.

LearnDash started making sales in early 2013. It was meant to be a lifestyle business for me, initially. But slowly over time the company grew into something more than that. With employees and customers from all over the world, LearnDash carved out a unique space in both the WordPress and e-learning industries.

When the pandemic arrived in 2020, LearnDash was very well poised to be found as people scrambled to create online courses – be it for extra income or to augment their entire business model. It was an insane time in more ways than one. The already healthy company grew even more in team size and in revenue. It was clear that the business was bigger than me, and far from the lifestyle business I created.

It didn’t take too long before I started receiving offers for LearnDash from venture capitalists. Truth is, this has been the case for the past few years, but during the pandemic that interest skyrocketed. I would get contacted literally every other day from investment firms looking to get a piece of the e-learning pie.

Now, I have always been one to pursue happiness, and this was the main driver for selling LearnDash. The truth was that I no longer had the same inspiration that I did for the industry, and this meant that I was getting in the way of the company’s true potential. LearnDash is bigger, and more important, than me. It deserved more so that it could reach that next phase of its potential.

The continued growth trajectory for LearnDash is huge, especially since it straddles both the WordPress and e-learning industries so well (which is unlike any other WordPress product, ever). Both the WordPress and e-learning markets will continue to grow in importance, and LearnDash will continue to be a leader in that space. Even more so with the backing and leadership of Liquid Web.

I hired investment bankers to market and sell LearnDash.

Given LearnDash’s unique position across two industries, I felt like professional representation was needed for the sale. In October 2020, I was introduced to the investment banking firm, Angle Advisors. I can say with confidence that had I not done this, LearnDash would have never found its new home with Liquid Web.

These folks are incredibly smart. Much smarter than me. We spent the remainder of 2020 preparing the financials and creating a management presentation. In January of this year, Angle Advisors reached out to hundreds of potential buyers. A large percentage of these companies were interested in learning more. They indicated this by presenting an offer for the company (usually a range). Those that made respectable offers were invited to a management presentation.

Let me tell you something about management presentations: they are stressful, and they are long. Each one that I gave was about two to three hours long, and in it, I discussed everything about the business. Its history, its present status, its position across the markets, the growth opportunities, and so on. It’s an informative presentation and a sales presentation all in one.

When all the presentations were done, the stopwatch began. The companies had to decide if they wanted to make a formal offer. Only three companies decided to drop out of the process. The rest submitted offers.

Moving into the due diligence phase.

With Angle Advisors’ guidance, an offer was accepted and the “one-on-one” relationship with the potential buyer could begin. I know that I said the management presentation is stressful, but honestly the due diligence phase is the most stressful part of it all. Just because you enter into this phase doesn’t mean that you will for sure close the deal. Either party can decide to move on for a variety of reasons.

In this phase, you set an agreed upon closing date for the deal. Leading up to that date, you have to provide the buying company with any piece of information that they request. Information on financials, market, product, legal, and so on — reaching back three to four years (sometimes longer). There are meetings, many meetings. The days are long and tiring for everyone involved.

In the latter stages of this phase is when the lawyers really start to get involved. Luckily for me, I didn’t have to worry about that too much since I was working with Angle Advisors (and they brought in Varnum Law to provide the counsel).

Once all the requested information has been shared, all questions answered, and all contractual agreements made from a legal standpoint, the closing can occur, and the buyer becomes the new owner. You finally can “hand over the keys to the house”.

LearnDash is in the perfect home with Liquid Web, and holy crap are they ready to take it to the next level! I’m especially thrilled that Chris will be taking an active role as General Manager. He is incredibly smart, and has deep roots in the online education space. He gets it.

What is next after you sell a business?

This is probably the most common question people have for a founder after they sell a business (besides curiosity on the sales price, which I am not sharing, sorry).

As I mentioned earlier, I live my life by prioritizing happiness. This has led LearnDash into the Liquid Web portfolio, and in the near term I am still very much part of the LearnDash team. I am in the middle of some exciting initiatives that I’ll be helping to see to the end (LearnDash 4.0 being one that I’m very eager about getting released). I will then be an active advisor to the company.

I get excited about new challenges. WordPress and e-learning have been good to me, but I’m running on fumes at this point. I’ve been involved in these two industries my entire life (e-learning since 2004 and WordPress since 2006).

I have interests outside of software and WordPress that I will have time to pursue. One in particular is starting a fitness brand with my wife, Lorena. I will be documenting this journey, so if you’re interested in hearing about the ups-and-downs of that adventure, check back here often.

I have learned from people sharing, so I plan to do the same.

I have learned a lot over the years about running (and now selling) a business. Things like competing, brand positioning, driving sales, and more. I plan to share these lessons learned on this blog. I’ll share exactly what it takes to build a multi-million dollar WordPress business across two industries.

Think of it like a conversation between friends. I had so many questions when starting out, and while there is no substitute for direct experience, a little guidance from someone who has been there before can be reassuring.

I won’t be selling courses or products, just writing. If you would like these insider tips, then just sign-up below. By doing so, you can also email me at anytime with your questions. All you have to do is click “reply” on a new post, and it’ll land in my inbox.

#WordPress #entrepreneurship

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