In the Now: Andy Bailey

The serial entrepreneur and Petra Coach founder says pursuing what’s next is a ‘chronic condition.’ But being both a business coach and an operating CEO has given Andy Bailey the ability to effectively blend theoretical knowledge and real-world experience in his interactions with clients. 

Watch the full interview with Andy Bailey here and read an excerpt from the interview below. 

Nowspeed: Welcome to this edition of In the Now where we focus on uncovering the myths and misunderstandings of marketing leadership including digital content strategy with some of the world’s most interesting people. And my guest today is Andy Bailey, founder of Petra Coach. Andy, welcome to the show! Could you kick things off by sharing with us the story of your journey with Petra Coach? Specifically, I’m interested in learning more about your transition from being an operating CEO to becoming a coach who mentors other CEOs. What led you to make this significant shift?

Andy: Hi David, thank you for having me on the show. I’ll begin by sharing the origin of my entrepreneurial journey which started when I was in college. In the early 90s, I established my first business. It didn’t take me long to understand that there’s a big difference between being good at something and running a successful organization that specializes in the same thing. That was when I stumbled upon Verne Harnish‘s scaling up methodology, then known as the Rockefeller Habits.

The Rockefeller Habits provided me with a framework that I could use to structure my business operations. I put this practice into play for my own business. Over time, I noticed a significant transformation, which ultimately led to the success of my venture. I operated that business for a total of 18 years. I must admit, though, that the first 10 years were quite challenging. However, the last eight were fruitful, and I’m proud to say that we accomplished a lot during that time.

The ultimate validation of our hard work came in 2011 when I sold the business. After the sale, I was left wondering what my next venture should be. I knew that the operational practices of the Rockefeller Habits, which is now known as scaling up, were extremely beneficial to me. It provided me with the freedom to grow my business while keeping chaos to a minimum. I knew that if I could pass this knowledge onto others, I could help them achieve the same success. So, I started by helping a few friends, and then I realized that I could turn this into a more extensive operation.

Today, Petra Coach is a full-fledged organization with about 30 team members spread across North America. We’ve grown our network and now have members in Canada, the US, Central America, and have recently expanded into Europe, specifically in Germany and Scotland. We’re collaborating with multinational organizations and helping them implement the Rockefeller Habits and scaling up methodology in the Petra process.

Nowspeed: Wow, Andy, that’s quite an inspiring journey. From being the operator of your own business to becoming a guiding light for other businesses with its own digital content strategy, it’s clear that you’ve learned a lot from your experiences. But I’m curious, which role did you enjoy more – being an operator or a coach? And could you explain why?

Andy: David, it’s a difficult question to answer because both roles have their unique rewards. I think my continual pursuit of what’s next is somewhat of a chronic condition. It’s never about being content with where I am. I’m always trying to figure out what’s the next thing I can work on, which I believe is a common trait among entrepreneurs.

When you’re running your own organization, you have the responsibility of being the guiding light. Your team looks up to you for direction, and there’s a lot of risk involved. But it’s a rewarding experience because you get to watch your vision come to life. As a coach, you don’t carry the same risk. You’re still a guiding light, but it’s up to the business owners to decide whether or not they want to follow your advice. The two roles have their unique challenges, but they’re both gratifying in their own ways.

Interestingly, I continue to do both today. After selling NationLink, I launched Petra Coach, which is an operating organization that I lead. Additionally, in 2013, we established Align, an operational business based in New Orleans, which today employs about 35 people. More recently, we’ve started a marketing company and also kicked off Boundless, another operating business. I must admit, it’s somewhat of a compulsion — I can’t seem to resist the urge to go through the struggles and the joys of growing organizations. It makes me feel like a bit of a glutton for punishment, but it’s undeniably fulfilling.

Nowspeed: That’s quite remarkable, Andy. It seems like you’ve successfully managed to juggle both roles simultaneously — coaching other businesses and operating your own. How do you think this dual perspective has influenced your coaching style?

Andy: That’s a great question, David. I believe my firsthand experience in operating businesses significantly enriches my coaching style. In the early days of coaching, I realized that my perspective on running organizations was deteriorating. It seemed like I was too focused on the pure methodology and losing touch with the realities of operating a business.

However, as Petra and my other ventures grew, and I continued leading them while making operational decisions, I was able to maintain a balanced perspective. Even with a clear roadmap of how to run an organization, getting it done is an entirely different challenge. By keeping myself in the thick of things, I have managed to stay in touch with the realities and complexities of operating a business. This dual perspective has allowed me to offer more pragmatic advice to the businesses I coach.

Nowspeed: That sounds like a fantastic approach, Andy. This blend of real-world experience and theoretical knowledge, alongside some strategy for digital content, surely makes your coaching incredibly effective. As we approach the end of this conversation, could you tell us more about your experience with the scaling-up methodology? In your opinion, what sets it apart from other operational practices?

Make sure to watch this interview in its entirety here.