Bootstrapper profiles & questions

I plan to highlight former and current bootstrappers who will share their stories, struggles and accomplishments about what it was like to bootstrap their ideas to scale and success. I’m shooting to make this a weekly or at least a biweekly feature on the site and Instagram.

Below are the questions questions I have at my side when I conduct these bootrstrapper interviews. These are some of the main questions I wrote down to guide me and stay on track. It is always good to go with the flow of the interview and use a question outline as a guide.

If you make a guide and follow it strictly, this inhibits you to “feel out” the tempo, flow and topic of conversation, leaving the impression that interview seemed forced, disjointed and uncomfortable. Aim for interviews to be conversational not twenty questions.

The question outline:

  1. What do you do?
  2. How did you get your start/decide to go for it?
  3. What made you gravitate to //insert industry/job/activity//?
  4. Where you daunted about the competition or saturation in this field?
  5. What were the early days/months/years like? (As in time, money, revenues, content and acquiring clients.)
  6. Biggest obstacles in the early stages?
  7. How did you stay motivated?
  8. What was your service and how did you sell it without having the quintessential corporate experience?
  9. Advice for those taking on the risk of being a bootstrapper? Advantages?
  10. Anything you would do differently in the beginning?
  11. Is there a common theme you see with your clients that people need the most help with?
  12. Anything I missed that you would like to add?

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