The Entrepreneur Ride Along – Introduction

Welcome to the Entrepreneur Ride Along. Follow along with me on the entrepreneurial journey as I learn, fail, and grow while testing, scaling and starting new businesses.

Along the way I will be scaling my online business, starting new online businesses, and talking to other entrepreneurs to learn exactly what they did to build their business.

About Jake

My name is Jake Lang.  First, and foremost, I am an entrepreneur who has started more than eight online businesses from scratch (and failed plenty of times along the way) scaling these businesses to the point where I replaced my day job income, quit my job in April 2021, and generated over $165,000 in revenue in 2021.

In the fall of 2014, as a senior at the University of New Hampshire, I attempted my first ever online business, buydirectmailadvertising.com. An absolutely terrible idea to sell a batch of residential addresses to local small businesses so the business could conduct a direct mail marketing campaign. Turns out, absolutely no one wanted this product. I started this website without ever asking what my customer wanted, I never even researched my competition!

Although buydirectmailadvertising.com was a total failure in terms of business success, it is one of the biggest successes of my life because it sparked my interest and love for starting niche online businesses. It was the best learning experience, and one of the most fun projects I have ever worked on.

Fast-forward to the summer of 2015, after a couple more failures and learning lessons, I founded AssociatePI. My most successful website that generates an average of $4,000 in passive income each month selling online courses in the insurance industry.  I’ve since invested my time elsewhere starting small niche sites including the Pomsky Owners Association (sold this business for $95,000 in 2021), a membership site for the Pomsky Dog Breed now generating approximately $2,000 per month through membership fees, AliExpress dropshipping, and a top-selling self-published book on Amazon.

I built all of my businesses on the side while working full-time as a product analyst in the insurance industry, on my lunch break, and while commuting to work. I officially quit my day job in 2021 to take on my businesses and entrepreneurship full-time. Now I focus on growing The Entrepreneur Ride Along Brand, writing books (like my book Step One), and building new businesses. I try to remain focused on what matters most in my life, which is my wife Brooke, my family, my dogs, and enjoying every day in my life without stress. I’m building these businesses so I can be financially free, and have more time to spend with my wife, friends,  family, and pursuing hobbies that I love. I do my best to put away work at 5 pm every day, and I refuse to work on weekends. Because of this focus in my life, I put in about 4 hours per day working on my businesses. If I can build these businesses and generate over $160,000 in revenue in one year working less than 4 hours per day (and no work on weekends), you can too.

With this experience, it is now my mission to help new entrepreneurs start and scale their online businesses. If you need some ideas, I recommend you start with my 10 small profitable business ideas.

My Websites

Here is an overview of the websites I have started. This is just a list of the websites I have started and monetized, this does not include the hundreds of ideas that never made it past the market validation stage.

There have been plenty of success along the way and lots of learning lessons. Follow along with each business below and think about what you can do to replicate this business to start your own niche website or improve your current business.

If you are looking to create your own website, I recommend you check out my 25 niche site ideas.

My Niche Website – AssociatePI

AssociatePI is currently my most successful business in terms of revenue. In this website, I sell online courses to help employees of the property-casualty insurance industry earn their CPCU® designation. I passed the CPCU® exams myself and turned my study materials into an online course to help others pass their exams.

I drive traffic through SEO, as I rank in the top three search results on Google for highly relevant terms related to the CPCU®. This website generates approximately 6,000 website visitors per month, which goes to show that you don’t need millions of website visitors to create a highly profitable website.

My primary sales strategy is to sell through my email list. About 90% of my sales come through my email list. This email list grows by approximately 300 new subscribers per month. Each new subscriber is fed into an email sales funnel to receive information relevant to their exam with an upsell for my online courses.

This website generates around $4,000 to $5,000 in passive income per month and has generated over $159,000 in revenue since I started the website (see the annual revenue graph below as of October 2019).

This website is completely automated and takes little to no input from me, the only thing I do is answer emails and tweak the website to increase traffic and improve conversion.

I am still working to tweak and improve this website. My goal is to generate $7,500 in recurring revenue for this website. I am currently working on strategies to drive more traffic, increase conversion, and drive revenue through a new affiliate relationship.

Follow the entire AssociatePI case study here and see what I’m doing now to increase the revenue of this website. In this case study, I’ll break down everything I’ve done from day one in a series of blogs, showing you exactly how I scaled this niche to generate $4,000 per month in passive income.

My Niche Website – Pomsky Owners Association

**Update. I sold this business in 2021 for $95,000. You can hear more about this process, and why I sold this business, here in this podcast episode.

The Pomsky Owners Association is a blog I started about the Pomsky Dog Breed. This website started as a side project in 2016 after learning that puppy mills were profiting by unethically breeding this dog breed, and thousands of people were being scammed trying to buy this breed online. I’m a dog lover myself, I couldn’t imagine living without my four great Danes (Miley, Millie, Penny, and Charlie), so I started this website to help people identify scams, shut down puppy mills, and provide reputable information about the Pomsky breed.

This website turned into much more than I ever thought it would be, though it took me years to get over some mindset hurdles to begin generating revenue from this blog (something I’ll share more about in a later blog and podcast). The Pomsky Owners Association is now, a membership site for the Pomsky Dog Breed generating approximately $2,000 per month through membership fees, AliExpress dropshipping, and a top-selling self-published book on Amazon.

Follow the entire Pomsky Owners Association case study here and see everything I did from day one in this series of blog posts showing exactly how I drive traffic, wrote a top-selling book, and turned a niche blog into a membership website.

The “dog niche” is extremely profitable. It’s why I include it in my list of niches that you should consider when starting your first online business.

My Niche Website – Agile Exam Academy

Agile Exam Academy is one of my newest websites, started in March 2020. I will be sharing my journey along the way getting this website up and running. The goal is to build a website to teach the Agile Methodology, starting with PMI-ACP® Practice Exam Questions.

My Niche Website – NE Lounge

NE Lounge, A.K.A my biggest failure as an entrepreneur. But failure’s a bad word. Instead, let’s call this my biggest learning lesson.

The NE Lounger was an “inflatable lounger” that I sold through the Amazon FBA program. You can see examples of this on Amazon here. NE Lounger is no longer active, I shut it down after selling off the remainder of my inventory. But you can see examples of “inflatable loungers” here on Amazon.

I will be the first to admit, I jumped in too quickly to this business. I first started this process in the summer of 2017 and I sold out of inventory by February 2018. The good news is, I sold more than 500 items of inventory, learned a ton about selling physical products, created my own inflatable lounger design, and formed a great relationship with my manufacturer in China.

The bad news, I lost about $13,000 in the process. Inventory is expensive, and the margins through Amazon FBA are thin, especially with this product that had lots of competition.

I had the right idea.  I did my research talking to customers and I entered the market with a better product. I built a larger more durable inflatable lounger. Exactly what people wanted. The problem is manufacturing each item at $18 apiece, plus Amazon marketing fees, plus Amazon’s cut for each sale left me with a fraction of the profit margin that I needed to breakeven.

One thing for sure, I will be back to Amazon FBA. And you will hear all about it when I do. Now I know that I need my manufacturing costs to be lower, now I know the whole process of importing goods from China through customs, now I know all the hidden FBA fees, now I know how to rank on Amazon, now I know exactly what to do to create a profitable business using Amazon FBA. It just cost me $13,000 to learn the lesson.

You can read about NE Lounge (my biggest failure) here in my interview at Failory.com. I will share plenty more about this expensive learning lesson in future blogs and podcasts.

My Niche Website – Sway Wear Clothing

Sway wear clothing, another website that is no longer active. Started in 2015 just before I started AssociatePI. I’m tall and I have stupidly long arms. I was fed up with buying dress shirts off the shelf that did not fit, either the sleeves were too short, or the sleeves fit but the waist stuck out like a parachute. I wanted to solve this problem, either with a better fitting dress shirt, a shirt that could be adjusted and self-tailored after buying, or a dress shirt that would be tailored before delivered to the consumer.

I learned from BuyDirectMailAdvertising.com. This time, I would validate my idea before putting in months of work. I talked to my target market and figured out there was a large group of both men and women facing the same issue as me. Dress shirts didn’t fit unless you got them tailored.

So, I set up a quick website and tried to pre-sell the idea. I set aside $100 to drive Google Ad traffic to a landing page where I would see how many people would go through to the purchase page. The plan was $10 a day for 10 days. I was trying to validate the concept that people wanted to buy my product before I put in the time, effort, and money to build it (thanks to the 4-hour workweek for the idea).

But…I apparently messed something up. Somewhere along the way, I must have accidentally clicked for Google Ads Express. I checked my account a week later to see $750 charged to my Google ads account. Not great for someone fresh out of college with plenty of student loan debt!

Word of advice, check your testing daily. In the end, testing resulted in hundreds of clicks and only one sale. Less than a 1% conversion rate. Add that to my ongoing conversations with manufacturers, tailors, and made to measure clothing specialists and I realized I was out of my element. I’m not a stylish guy myself, my Fiance dresses me, I can barely dress myself with matching colors on a day to day basis. Ceating a whole brand of clothing was not in my zone of genius. I shut this website down after a few months and some testing. On the brightside, Google surprisingly refunded me the $750 charged from Google Ads Express. I guess that’s the one perk of playing the broke college kid pity card.

Sway Wear Clothing was started right before things like Indochino, Untuckit, and MTMshirt blew up. So, I had the right train of thought! I was trying to get into the same market right before these big players blew up, now you see Indochino and Untuckit everywhere. I probably could have carved out a little niche here and differentiated myself from the big players, but it was way out of my element and would have taken me away from other projects that I could start with less hassle.

I will share more about Sway Wear Clothing and how I tried to validate the idea in future blogs and podcasts.

My Niche Website – Buy Direct Mail Advertising

My first ever website, and the one that got me hooked. BuyDirectMailAdvertising.com.

Through my university, I was granted access to a database of addresses. I don’t know why I had access to this, every student at the University did. Working as a business development intern for a small IT firm, I knew that small businesses were running direct mail advertising campaigns. I was running direct mail campaigns for my company and I was always looking for a database of leads. I saw this as a potential business opportunity. I had access to a database of addresses through my University, I could sell these residential and commercial addresses as leads to small businesses around my campus. I’d sell each address for $0.05.

I found this great domain name using Long Tail Pro (my favorite keyword research tool), I’d be able to quickly rank for keywords like “Direct mail advertising” and “Buy mailing leads”. I’d be rich!

Except I didn’t talk to a single person in my target market before starting the business. I just started it without asking. I didn’t even consider if anyone wanted this product. I just built it.

And guess what. No one wanted it. Turns out there is this thing called Google where people have unlimited access to addresses. I called and emailed twenty businesses in my area, businesses that I knew used direct mail advertising. Pizza shops, tax firms, lawyers, etc… I was ready for the money to start flowing in. Time to drop out of college! Here comes the next Bill Gates, the Bill Gates of selling direct mail leads.

Instead, I was very quickly told “no” by every single person I talked to. All politely declining and telling me they either have a service that does everything from lead generation to sending the direct mail campaigns already, or they use free services online to batch residential addresses. There was no need for my product.

It was an eye-opening experience and a much-needed lesson. I didn’t even ask what people wanted, I didn’t even ask if they needed my service. I just assumed if I built it, people would buy it. But that’s not how business works.

A very inexpensive learning lesson, about $20 for the domain and hosting and that was it. But, probably the best investment of my life. It hooked me on online business, and blogging, and creating content, and trying to get that first sale. It took me about a whole year and a few more failed attempts at online business until I finally got that first sale. And that never would have happened if I didn’t step out there and learn, even if it was the dumbest least thought-through business idea ever. I wouldn’t be here writing this blog if I hadn’t attempted to sell direct mail leads and suffer the rejection of a “No” twenty times in a row.

I will share more about BuyDirectMailAdvertising.com and my first experience with online business in future blogs and podcasts.

New Niche Websites (in progress)

Pellet Stove Home – where all things pellet stoves are discussed including (but not limited to) pellet stove brands, parts, and accessories.

All These Photos – is a print-on-demand photography business.

Follow Along

Follow along with me on this journey. Start by downloading The Five Niches Websites I Would Start Today (if I had more time). 

I’ve learned a lot about starting online businesses, and I have a huge ongoing list of new niche websites that I want to start (100+ ideas last time I counted). In fact, most of these I have started the initial phase of market research and talking to prospective customers to validate the idea.

The problem is, I don’t have time to start all of these new niche websites. Which is why I started The Entrepreneur Ride Along. So I could have an outlet to meet and talk with other entrepreneurs about online business and these entrepreneurial ideas.

That’s why I put together this downloadable list. My list of the five niche websites I would start today if I had more time. In this download, in each email, I will send you a detailed breakdown of a niche website idea. These are my favorite types of niche websites, they are types of sites that I have created in the past to generate anywhere from $1k per month in recurring revenue to $5k per month in recurring revenue. I want to introduce you to these ideas so you can create a niche website yourself to begin generating $5k per month in recurring revenue.

In each email, I will give you an overview of one new niche website idea including:

• Why I love each idea
• How I would make money from this niche site
• What I would do to drive traffic to the website

Click here to download the list of the 5 niche websites that I would start today to earn $5k per month in passive income.