- How difficult it is to move from being good at something (teaching/producing radio shows) to creating an organization where you lead others to do that.
- Thinking of a name and how you drive yourself nuts trying to come up with one that is “perfect”, only to have others think it’s awful!
- What happens when you are obsessed with starting something and the stress that puts on those around you. If you’re like Blumberg and me, you’re lucky to have a partner who is incredibly supportive, but even with that support it's in no way easy.
- Coming up with a good “elevator pitch”. You can have a general idea of what you want your school/business to be like and you can explain it in 10 min, but how can you boil it down to 30 seconds that excite a potential supporter?
- The challenge of getting feedback from others while staying true to your core concept/values. You hear a great idea from someone else that you hadn’t originally thought of – do you change your plans to include this idea? Or would that distract you from your core idea?
- Recruiting and investing talent in your organization when nothing exists yet of what you hope they are signing up for.
- Learning on the job and dealing with mistakes, because you will make them.
- Doubt. So much doubt.
Seriously you should listen to this - for two reasons. First, even though the context for starting a podcast company is different than starting a school, the big ideas, many detail, and most importantly, the emotional roller coaster rang very true to my experience as a KIPP founder so if you listen to this and it seems insane that someone would want to do this, you might want to rethink your plans. Secondly, it's reassuring to know that there are crazy and successful people out there in all different fields following their dreams and pulling it off. Helps with that last bullet point above.