If you have ever had to fill out the same healthcare forms time and again, you will appreciate what Sean and his team at Olive AI is doing. They are using AI to cut through the huge amount of money that is waisted on healthcare administration. 

Sean is an accomplished entrepreneur and former Air Force intelligence officer, so it was also enlightening to learn about some of the challenges he has encountered around how to keep his leadership focused on the people and not the technology.

Isaac and his team of over 400 have earned $93 million in venture financing as it helps take care of over 45,000 employees in all 50 states. In this interview Isaac gets very specific about his feelings of failure, being real with his team when things are not going well, and how he has structure his team for growth. Plus, it was fun for me to talk with a fellow Army Intelligence Officer veteran.

Sandra built her business on service. With over 100 employees, she has created a premium subscription staffing company that is helping a growing number of entrepreneurs. She shares a story of a bad hiring experience that prompted her to create a better hiring process. She now interviews candidates with 4 Attitudes in mind. Listen as she shares this painful experience, the 4 attitudes, and her only challenges on the road from Founder to CEO.

Richard is a self-proclaimed math enthusiast. And, as he says, he likes to solve math problems, teach, and build things. So, when he revealed some of his personal challenges in becoming a CEO, they were very different than what you might expect. Because, as he says, "People are all different, they're snowflakes, you can't treat them as widgets, you can't treat them like math problems."

Dan understands delegation. He has mastered the art of delegation in a unique way. He shares his unique approach to delegation, his systematic review of talent, and how he communicates with his team.

The best startups a born out of Founder frustrations. Haley is a lawyer who hated the manual process for helping Founders and attorneys with deal flow. So, she created a collaborative SaaS platform that is having a big impact. She also knows being a Founder is hard work. Balancing giving the team direction with empowering the team was a challenge for her. She explains what she learned in this interesting interview.

Sometimes focusing on simplification is the most important action a Founder can take. Austin knows this. He helps entrepreneurs, like you, simplify and focus. And, he too knows the perils and pitfalls of being a Founder and leader. He candidly shares the story of when one of his team members ask him: Have you thought about hiring a CEO? His response to this question will amaze you.

There's a dirty word in some entrepreneurial circles. It starts with s...no, not that word. It's structure. Yes, some Founders shy away from structure, processes, and systems just at the time the business needs a bit more. Christian experienced this himself and is helping Founders like you better navigate this important part of entrepreneurial leadership.

Daisy Ozim is passionate about helping marginalized communities get access to and use the healthcare resources in their area. She is using tech like blockchain to make it happen. Plus, she shares her own struggles with Founder health and how important it is to the success of your business.

You can learn a lot about Founder development from the Founder of a church. That's why I was very excited when Luke Dooley agreed to come on the show. Luke learned a lot being the Co-founder of Journey Church and has applied his lessons learned as the Vice President of Program for the OCEAN Accelerator.