Leadership Journeys [80] - Caleb Avery - "When I'm getting anxious and overwhelmed, it is because I am spending too much time on things that I have no ability to change."

This is the Leadership Journey series on the Choosing Leadership Podcast.

I believe we all have a lot to learn from each other's stories - of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, my attempt is to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name.

In the conversation, Caleb shares how his entrepreneurial journey started at college going door to door when he was only 19 years of age. We spoke about how the role of a founder or leader changes as their company grows to more than 50 people. He shared the challenges that presents as you have to learn to let go and trust others, and how invests in his own learning in this process.

Caleb discusses the challenges he faced while going door to door and trying to sell their payment processing services to small business owners. He shares how this experience helped them to handle rejection and empathize with people. He also talks about the importance of leading by example and how a founder-led sales approach is crucial in the early stages of a business.

Caleb emphasizes the importance of pushing oneself out of the comfort zone and doing things that they may not be incredible at, to help the organization grow. Finally, we discuss the importance of feedback and being open to suggestions from investors, the board, and the team. Overall, the conversation is an inspiring and educational look into the journey of an entrepreneur and the challenges they face along the way.

You can find Caleb at the below links

• https://www.linkedin.com/in/caleb-avery/
• http://www.tilled.com/

In the interview, Caleb shares

• my entrepreneurial journey at 19 by co-founding , uh, credit card processing business when I was in college. And started my career going door to door, selling payment processing services to small business owners over time, scaled up that business.
• a buddy of mine at the time, uh, we were talking about this idea of credit card processing and ni neither of us really knew anything about credit card processing at that particular time.
• I learned, in that experience was really, the, this idea of rejection and how to handle, the rejection, not take it personally, how to overcome those objections and really. Taught me a lot about, how to sell, how to empathize, with the people you know that you're working with.
•  it's easy to fall into the trap of focusing on the things that, you're good at you enjoy, and you could basically do on autopilot. Like that's the kind of comfort zone, for an entrepreneur. And oftentimes like, that's where you decide to go start a business.
•  it's easy to fall into the trap of focusing on the things that, you're good at you enjoy, and you could basically do on autopilot. Like that's the kind of comfort zone, for an entrepreneur. And oftentimes like, that's where you decide to go start a business.
• for the organization to grow and for you to evolve, into that c e o role, you have to push yourself out of that comfort zone and say, Hey, here's something that I need to go do.
• I'm an entrepreneur, at heart that's what my business needs and you have to have leaders in the right roles within the organization that have that desire and intense focus.
• leader myself, empower them to have the ability to institute, follow and maintain those processes without me, getting in the way.