8 Lessons I Learned from Starting 4 Very Different Side Businesses

I’ve always had a passion for entrepreneurship.  There’s just something awesome about building your own product, finding a market for it, persuading people to buy it, and making a living off your own ideas and hard work.

Being an entrepreneur is all about trying new things and learning from them.  You’ll never learn what works if you don’t first make an attempt at an initiative.

“All life is an experiment.  The more experiments you make the better.”  -- Ralph Waldo Emerson

I've had the good fortune to start, build, and operate four very different side businesses.  Here are just some of the very valuable lessons I've learned over the past 16 years...

Business #1:  YouNique4U Gifts (eCommerce site)

I launched my first side business in 2001, right when the first dot-com bubble started to burst.  I created gift items that were personalized with the meaning of your name or the history of your birthday.

I purchased some software that would create the content and then I’d put it into a framed plaque or on a product like a coffee mug or Christmas ornament, eventually building a product line of about 50 different items.

Lessons learned:

#1 - Don’t Pick a Clever or Hard to Spell Name

I originally wanted the name YouNique Gifts -- still somewhat clever but relatively easy to explain and spell.  Unfortunately, that name was taken, so I got overly clever by adding the “4U” at the end.

Suffice to say, I ended up always having to explain and spell out the name when discussing my business.  And even then, a lot of folks wouldn’t quite understand or get it.

In the end, just go with something that is easy to say, understand, and spell!

#2 - Creating Products by Hand is Hard Work

I initially loved the idea of creating my products by hand.  However, after several months of creating all these hand-made products, it got to be difficult and tedious.  

I tried to find ways to make the products digital, but the price-points were too low to effectively market.  This is one of the main reasons I decided to abandon this business.

Business #2:  DR Marketing (Affiliate marketing business)

This was by far the most successful of my four home-based businesses.  I operated it for seven years as a side business while working full-time at other companies.  

It was essentially an arbitrage business where I would market other companies’ offers on Google Adwords and pocket the difference between the commissions earned and ad dollars paid out.

It was so successful that by the second year, I was making more money operating DR Marketing on the weekends than I was working F/T at my regular day job.  I averaged about $130k in profit for the two best years (2005 & 2006).

Lessons learned:

#3 - Ride the Gravy Train While You Can

If you ever have an opportunity like I had where you can earn more money for a P/T business than your F/T job, enjoy it while it lasts!  

Don’t take these opportunities for granted, because they most likely won’t last.  This business was great, but it eventually died out for reasons coming up….

#4 - Google Has a Lot of Power

My business basically lived and died by Google.  When it was going strong, I was spending hundreds of thousands of my own dollars profitably on Google.  

But eventually Google decided (and rightly so) that they didn’t like affiliates running so many ads on their site.  They made a number of sweeping changes that would end up killing this business model.

Business #3:  Full Lotus Marketing (Marketing Consulting company)

My third business was a partnership with a friend of mine, and we consulted small businesses on their online marketing needs (Google Adwords, Facebook marketing, Content marketing, etc).

It was a fun ride, but we burned out pretty fast due to…

Lessons learned:

#5 - One Bad Client can Severely Hurt a Business

We had one client (won’t mention any names) that didn’t like our work and refused to pay us.  Suffice to say, we had put in a lot of our own time and paid our contractors to help this client, so their refusal to pay really hurt us financially and set us back substantially.

#6 - Service Businesses are Hard to Scale

In order to keep growing, we had to either put in more and more of our own time servicing clients, or we had to keep hiring people to help.  This was kind of exhausting, since we would’ve rather focused mainly on getting new clients.

We tried coming up with a physical (electronic) product that we could sell, but we just didn’t have the bandwidth to create it while servicing our clients.

Business #4:  Experiencify (Content Site & Blog)

This was my fourth side business.  I started working on it (with my wife Allison) in January of 2015 after we both got laid off from our “real jobs.”   Experiencify provides inspiration, tips, and resources for having amazing life experiences.  

Think Bucket List adventures like climbing Mount Everest, walking the Great Wall of China, and visiting the Eiffel Tower in Paris.  To more “down to earth” experiences like finding the best pizza joints in the U.S. or driving along the world’s most scenic road trips.

Lessons learned:

#7 - Be Prepared to Produce a LOT of Content

I realized that to create a content site / blog that attracts readers and keeps them coming back, you have to have a lot of content.  We’ve published hundreds of pages of content on our site, including over 30 blog posts, several quizzes, and a variety of resource pages.

#7a - The Content has to be Really Good

Not only do you need to produce a lot of content, but in order to have Google index you highly and have readers continuously come back, your content better be really compelling.  There’s so much content out on the Internet, so you have to really stand out from the pack.

And as far as SEO goes, the #1 tip is to make sure your content is really great -- it answers questions users may have, surprises them, inspires them, and keeps them engaged.  Google is becoming much smarter about recognizing what constitutes good quality content by analyzing click rates, time on site, bounce rates, number of pages viewed, etc.

#8 - Content Alone won’t Generate Much Revenue

If you just purely have a content site, you can make some money on ads and/or affiliate links.  But unless you have A LOT of traffic, that revenue will likely be very small.

Once I realized that, I started thinking about what kinds of “products” could I create and sell on my sites.  I considered a book (or ebook), but then decided to focus on creating online courses for my next venture...

My Current Side Business

I started Retire By 45 in August 2016 after blogging on Experiencify about how I retired at the age of 43.  

It was clear this concept resonated, and my audience wanted to learn more.  So Allison and I created Retire By 45 to help people learn about personal finance and becoming financially independent.

It’s been so much fun working on this side business.  And fortunately I’ve been able to apply many of the lessons I learned from first 4 side businesses:

• Name:  Retire By 45 is easy to say, read, and understand.  And the idea behind it is pretty self-explanatory
• Traffic:  I’m not reliant on getting traffic from any one source (like Google).  I use a wide variety of content marketing, social media, and email engagement for traffic.
• Product:  I decided to create digital products and content (not services or physical products), ranging from blog posts to calculators to online courses.
• Content:  Fortunately I love the subject, so I enjoy writing about it.  I try to create content that is meaningful, intelligent, and enjoyable for my audience.

Conclusion

My first four home-based businesses have come and gone, and we’ll see how my fifth goes.  One thing is for certain -- each one provides so many opportunities for learning and growth.

“I’m always doing that which I cannot do, in order that I may learn how to do it.”  -- Pablo Picasso

No matter what happens, the entrepreneur in me will always have a full-time or part-time home business running.  The process is as rewarding as the outcome!