From Founder To CEO

Health is everything. Founder fitness is everything. Michael knows abut both. That's why he created a company that uses NASA technology to make outdoor gear warm and free of bulk. It's also why he discovered that being a Founder requires focuses on his health and prompted him to lose over 20 pounds so he could better lead his company. Hear what happened and what he did and does about it so his company can soar.

Our very first, real Irishman on the podcast for this interview. :) I could talk with Tomás for ever. He is a smart, savvy, experienced Founder who is more than willing to share his journey from Founder to CEO. He had somewhat of a unique start to his business. I really appreciate how he turned a bad situation into a great business. We talk about the unpleasant need to fire a team member and how he handled the departure of two key team members who left his company while recruiting away his customers. We even talk about my favorite butter...made in Ireland. :)

The payments industry is a beast of an industry to enter. There are a growing number of players, lots of regulation, entrenched legacy leaders, and difficulties building and maintaining trust. But, PJ Gupta saw not only a need, but has a passion for helping millions of businesses reduce their payments costs and speed up their cash flow...so he took on the challenge of sending an receiving digital checks.

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.

Speaking with Richard was a real treat for me. The company he started and still leads has had a very positive impact on my son. 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." 

After we discussed his challenges in shifting from Founder to CEO, he and I came up with 4 actions you can take that will help you make it an easier transition.

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.