Ride Shotgun - Building a Profitable Side Business



Riding shotgun is a turn of phrase that came from stagecoach days, referring to the presence of an armed protector who would provide security for the driver and passengers. He/she would ride alongside the driver with a shotgun in hand.

In modern days the term has come to mean, besides the more literal interpretation of riding in the passenger seat of a car, to join someone on a journey, either physically or metaphorically.


For the past several months I have been busy building out content for 2 online courses that I will be launching in April and May of 2015. I had originally intended to write a book, but decided that the people who would benefit most from the content would benefit more from online, self-directed courses.

The Social Entrepreneur will be an in-depth online course covering every aspect of taking a social enterprise idea (a business with both a profit and a social mandate) from inception to launch, growth and profitability.

The Adventure Entrepreneur will follow the same online course format, only customized for those looking to launch and grow an adventure travel business. 

Both courses will draw on my 19+ years experience growing my company Sacred Rides to over $250,000 in monthly revenue, my 5+ years mentoring social entrepreneurs at the Centre for Social Innovation (first as founder of social enterprise incubator Project Wildfire and then as Dean of Social Enterprise at CSI), and my continual learning and training on all aspects of entrepreneurship.


Now that the bulk of the content for the courses is ready, the fun - and the true test - begins.

The two main tasks remaining (and they're big ones!) are:

a) figuring out the business model (customer segments, revenue model, value proposition, etc..)
b) figuring out the marketing strategy and then executing on it

I should mention here that my company, Sacred Rides, still occupies the bulk of my professional time. Although it's a very mature (and fast growing) business, with well-developed automated systems and a great team that helps me mostly stay out of day to day operations, I'm still very focused on growing the company, with an eye towards an exit in the next few years. 

I also have a wife and 3 young kids to whom I would like to devote a lot of my free time, a mountain bike that needs riding, and friends whose company I very much enjoy.

So the challenge will be figuring out how to build a business model and execute a marketing plan on very limited hours.

A big part of that strategy will involved staying committed to my morning routine, which I wrote about in an earlier blog post. The other part of that strategy will involve tremendous focus, using every productivity and strategy tip that I've picked up over the years, while applying Lean Startup principles to run through feedback loops as quickly as possible, and get to a business model that works in 3 months or less.


I'll be pursuing 3 main growth strategies to build both my subscriber list and my customer base:

1) Kickass content marketing:

a) publishing the best blog posts I possibly can
b) leveraging my relationships (see #3 below) to spread that content
c) optimizing content for search engines so that it continues to be found by my target audience for years to come
d) converting visitors into subscribers (with the promise of more great entrepreneur-focused content)
e) converting subscribers into customers (with the promise of top-notch, affordable products and courses for entrepreneurs)

2) Paid advertising into a continually split tested and optimized sales funnel: I'll be running Facebook Ads to a free offer page (such as my 15 Apps and Tools for Social Entrepreneurs), then taking them further down the funnel with discounted introductory offers and then eventually offers for my core products - The Social Entrepreneur online training and The Adventure Entrepreneur online training courses (both launching late April 2015) and my Social Entrepreneur Bootcamps.

3) Relationship building: Developing relationships with other influencers in the social enterprise sphere and building on existing relationships to support our mutual goals.


I'll be writing regularly about my progress, with a goal of getting to $5,000 in monthly revenue in 3 months or less (roughly mid-July 2015). Because my (financial) costs are minimal, most of that revenue will end up as profit - if I can hit my targets I'll have a nice side income, and hope to demonstrate that this is possible for others as well. Many of the entrepreneurs that I teach and consult with follow the same path, launching their businesses while pursuing other, often full time, employment.

This will be a big test of all of the stuff that I teach to my students. I'll share all my strategies and tips, and update you on my revenue numbers, as well as all the highs and the lows along the way.

Come along for the journey - SUBSCRIBE TO MY MAILING LIST and ride shotgun with me!

Want more training on productivity and social entrepreneurship?
Join me at SOCIAL ENTREPRENEUR BOOTCAMP, starting April 29!

Want to know the 15 apps and tools I use for maximum productivity? CLICK HERE