Takeaways: 

• Selling into healthcare takes a long time - for good reason.
• Having worked in both the education and healthcare market selling software, both are difficult markets. While healthcare has more budget than education, both take forever to make a decision.
• Young entrepreneurs should think about getting some enterprise-level experience before starting a company.
• How entrepreneurship is like parenthood: you don't know it until you try it.
• Early technical decisions can have an outsize downstream impact, and is perhaps more important than go to market activity.
• Moore's most important job as CEO was first to drive revenue, then later to set the company vision and cultivate its culture.
• In his current role as an advisor, he stresses operational discipline over founders habits.
• The number one attribute for entrepreneurial success? Being able to work through ambiguity.
• Managing customers and raising kids both involve cultivating their independence from you.
• Jason's favorite saying? "People gonna people." It's not just negative - people also do amazing things. But just know that folks will disappoint you at some point.
• Advice to his 23 year-old self: Push through the hard times and keep people close; don't lose your focus on them.