Putting Together the Pieces of a Content Strategy Puzzle

At Bootstrappers Breakfast, we often hear a wide range of marketing challenges that entrepreneurs and young businesses are looking to solve– such as lead generation, developing a strong online presence, time management, focus. Marketing may not be your forte if you’re more of a visionary entrepreneur, with big ideas and passion, or in the trenches with product and operations. And there always seems to be insufficient resources and budget. In today’s competitive market, starting a business is hard enough, let alone growing it.

In May’s Philly Bootstrappers Breakfast, a lot of what was discussed were different pieces of the content strategy puzzle. Let’s break it down.


Developing a content strategy - to drive results through your content, you need a solid strategy. First off, you have to set and define goals. Never create content just to create it. Instead, constantly measure the impact your content marketing is having on your business. There's no magic, one-size-fits-all formula. Your strategy should be uniquely influenced by the size of your business, budget, resources, A/B testing, and other factors.

Next step is to figure out your core messaging. This comes up a lot in Bootstrappers. How do I define what it is that I do and why it’s important?

We introduced a concept that Mike learned from Alex Kutsishin, a colleague in Baltimore, called, “Sticky Pitch.” He suggests that a business pitch should be like comedian’s joke, where everyone gets it regardless of their background. He shares the following formula:

  1. Who is your product or service for?
  2. What are they unhappy with?
  3. Broad overview of what it is.
  4. What is it unlike?
  5. What's your unfair advantage?

By answering all of these points, you’ll have a proposition that resonates with almost anyone you might pitch.

Another important aspect of a content strategy is developing personas, descriptions of your ideal customers that you’d develop as part of a brand strategy. Content is less boasting about how great your product or service is, more about understanding your audience and helping them solve pain points. This first requires us to know our audience. When you are creating content to reach potential buyers, it’s most effective to combine your personas with the buyer’s journey framework. Gear your message to each stage of the journey: Awareness, Consideration, Decision.

Producing Content- Taking the elements we’ve discussed (Goals > Messaging > Personas) should help you determine what types of content to focus on. With so much to read and see on the internet, being strategic, understanding what to focus on, and setting goals around each initiative will help you reach the right audience with the right message.

Here are a few Bootstrapper’s ideas to consider when you plan your content calendar.

  • Create a YouTube Series - We had an attendee who was creating an app to compete against the big name health care providers. He was starting a video series to demystify the healthcare industry. This type of content hits his audience at the Awareness stage, educating and solving a potential problem.

  • Surveys are a great way to create a story using data. Once you’ve found a concrete story, you can publish and pitch it to the press.

  • Advertising. If there’s one thing we can stress in this post, it’s this: Know your competitors and follow what they’re doing. Big name brands likely have big budgets to spend on marketing and advertising campaigns. Take what is already working and tweak/position it to align with your message. Differentiate it by adding your personal touch.

  • Thought Leadership. Use the talent, experience, and passion of you or your business to answer the biggest questions your audience faces on a particular topic. Identify the questions your customers are asking and answer them on multiple channels. Become an authority and add value.

Lastly is reaching your audience. This requires an understanding of the marketplace and customer needs and wants. Know where your audience lives and how to target them on different platforms. Make sure your content is relevant and easy to find. Connect with influencers and have them re-share to their networks. Distribution and amplification are just as important as creating content!

It may sound like a lot of work, but having a strategy and content calendar in place will help you get ahead. Don’t feel alone in the struggle! Many small businesses face similar challenges. There are tons of resources, tools, strategies, and networks at your fingertips, including the Bootstrappers Breakfast, with upcoming meetings in Philadelphia and NYC.