Bootstrapped Founders - How to Craft the Story Behind Your Business

September 1, 2021
Man with glasses, wearing a sweater, speaking in front of a Marvel character mural.

As bootstrapped founders, we may not find ourselves about to give a formal pitch in front of suited VCs, but we do constantly interact with potential customers, partners and other stakeholders in our networks. Every one of these people should know what you do and most importantly why you do it.

You’ll know it’s time to tell a story about what you do and why when you get questions like these:


  • Why did you start your business?
  • What are you up to lately?
  • Tell me about yourself


Here’s how you can craft a version of your story that will feel authentic and extemporaneous, but also be an influential and powerful representation of you and your business...


1. Create a rough draft.


You already tell a version of your story even if you haven’t prepared and you’re not confident about it. Imagine somebody asking you one of the above questions and write down an answer to it. If putting pen to paper is challenging, don’t let that get in the way! Make an audio recording of yourself and then transcribe it. The point at this step of the process is to simply get something down - don’t worry about editing or refining it to perfection just yet.


2. Pinpoint your theme or main takeaway.


Having a theme in mind will help you stay on track and avoid tangents. With preparation, knowing your theme becomes a true super power. With a clear idea of what you want people to take away from this story, review your draft and eliminate every piece of context and action that doesn't relate to or build upon your theme. And make sure you close your story by reinforcing this main point.


3. Make it visual.


If your audience can picture your story while they listen, the story becomes easier to follow and experiential. This makes what you share more memorable. Consider your story as a series of scenes. For each scene, make sure you include some sensory details as well as time and place indicators to make your story more cinematic.


4. Practice and get feedback.


Just like the design process that you use for your product or service, think about your story development as an exercise in rapid prototyping. Take an early draft and share it aloud with someone safe like a friend or colleague. Once you’ve shared it, ask them questions to help you refine your message:


  • What did you take away from this story?
  • If I want you to take away [your theme], what should I include or remove?
  • What was powerful about the story?
  • What felt unnecessary or extra?


Your story will continue to evolve as your strategy shifts over time and your business grows, but you’ll be surprised by how much your “why” stays the same and this will soon become a go-to story.


In the meantime, if you’re struggling in your story development anywhere in the process, join us at a free Story Hour to get some insights and experiments to try.

Summary of Takeaways

The shift to a hybrid work model requires leaders to evolve beyond traditional "in-office" management styles. To maintain connection and performance in a virtual/in-person mix, focus on these four strategies:


  • Practice Mindful Leadership: In a cycle of back-to-back meetings and potential burnout, mindfulness is essential. This means shifting from a reactive to a strategic mindset, being truly present in every interaction, and respecting the boundaries of both yourself and your team.
  • Leverage Audio-Only Moments: Not every meeting requires video. Transitioning to phone calls can reduce screen fatigue, allow for better focus on content without the distraction of self-image, and even enable "walking meetings" to improve physical and mental health.
  • Reinvent Team Building: Move past the "Friday Pizza" model. Since remote employees can feel secondary in hybrid settings, experiment with inclusive alternatives like virtual coffees or localized activities where members share stories afterward.
  • Proactively Recreate "Hallway Coaching": Ad-hoc feedback moments have vanished in hybrid work. To prevent team members from feeling isolated or like a burden, establish dedicated "Office Hours" or routine ad-hoc check-ins to provide the guidance and encouragement that used to happen naturally in person.

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