Breaking Down Your Business | Small Business | Business Owners | Entrepreneurship | Leadership

What’s In This Episode:

As business owners, there's one overarching thing we have to do: we have to make decisions. Big or small, there is seemingly no end to the things we have to make a call on (that's why Mark Zuckerberg and Steve Jobs famously wore the same thing every day, so they could avoid having to decide what to wear). Sometimes, it's just exhausting.

"One of the rules that I recommend is that no one can work for the family until they've worked for someone else for a few years." - Brad

Former trapeze artist Hannah Sullivan and her wife Jade call into the podcast to discuss one big problem: working with family at their company, Pogo Insurance. Hannah's dad, their boss, is your typical alpha male and constantly wants to be the hero. Some of Hannah's siblings, who also work for the company,  don't do their fair share of work. Overall, the ladies just want to be taken seriously.

Brad says that one solution is to have regular family meetings. Establish ground rules and talk about what's going well (and not so well).  If they can separate out and have Hannah's dad as a mentor or advisor, that might be the best case scenario. If not, the other solution is to work someplace else.

"You can't value other people more than you value your own services." - Jill

Jill and Brad then discuss the top 5 worst business decisions they've made:

  • Signing a contract without reading it.
  • If you're going to put on an event, make sure you promote it.
  • Not charging for speaking or consulting.
  • Scaling the business too quickly.
  • And please, please, please, don't do this...

Want to know what it is? Listen in


  • This episode is sponsored by Warby Parker. Buying glasses can be expensive, annoying, and overwhelming. Warby Parker cuts out the middleman by providing high-quality eyewear at a fraction of the cost - and for every pair you buy, they give away a pair to someone who can't afford them.  How can you try glasses out online? Check out their Home Try-On Program for free and get started to find your perfect pair of glasses.


  • Hannah and Jade Sullivan are the co-founders of Pogo Insurance, an online platform that offers commercial insurance policies for freelancers, consultants and others who are self-employed.
Direct download: Breaking_Down_Your_Business_EP_244.mp3
Category:Business -- posted at: 3:00am EDT