CEO Insights Panel

In a first-of-its-kind of panel at ITEXPO in Miami last week, I moderated the CEO Insights panel which included: Adam Cole – Founder and CEO of SIPPIO, Eric Hernaez – CEO of RabbitRun Technologies, Tom Joseph – Founder and CEO of White Label Communications, and Tony Lewis – Founder and CEO of Clearly IP. These four distinguished CEOs have all been a CEO multiple times and have founded and exited a multitude of companies.

The panel provided a behind-the-scenes look into the journeys each took to become a CEO, the challenges they face every day, and over the past 16 pandemic months. Each provided tips and guidance for those who wish to become a CEO or a senior executive leader in their career.

As moderator and author of “The Rookie CEO, You Can’t Make This Stuff Up!”, I bring a passion for learning about CEOs, helping CEOs, and helping aspiring CEOs and leaders prepare for the top role. I asked questions of each panelist, offered a lighting round to learn little-known factoids about each, and each CEO offered tips and guidance for how to achieve the dream, how to build a team, and how to build a successful company.

This is the first blog in a 3-part series that will discuss the conversations we had with the leaders in front of a large audience in the first session of the day. Luke Bellos, TMCnet editor, published this article in the ITEXPO Show Daily and did a nice job capturing the highest level of discussions. My blog posts will delve into more detailed discussions.

Key Take-Aways

One of the common threads throughout the session were that hiring a top team of leaders on the management team were critical success factors for success. Another common response to the questions were not be the smartest person in the room – hire people smarter than you are. Having experts on your team that you can trust to execute and get the job done as expected, were CEO and company success factors.

The CEOs also discussed how they handle challenges on the leadership team and how they each address them to minimize negative impact. All were candid but consistent in their methodologies.

At one point, it was clear that the panelists were learning from each other. This is truly how it works.

The CEOs

A little more about each CEO will help you understand who they are, where they come from, how their mindsets were shaped for CEO and how they got there:

Adam Cole: Adam is in his 6th startup, 5 in tech, and one other. As a founder CEO, he is experienced in creating companies, building his teams and is a strong supporter of earning the title and respect of his teams. He believes working through every situation, thick and thin, will grow you as a CEO to prepare you for any future situation with a clear mindset. His takeaway from the pandemic is that he can’t wait to get everyone back in the office. A little know factoid is that Adam is a chef in his spare time.

Tom Joseph: Tom has been a CEO for about 20 years in every stage of a company – from startup to scaled up. He always wanted to be a CEO and in his career, and he made sure that every role he took was on the vector to get there. He once declined a great opportunity that would have been a lot of money but took him off of his path to CEO. This shows conviction to me. I write about this concept in my book, as part of the Path to CEO section. His approach is to learn the business, learn from mistakes and stay focused on your mission.

Eric Hernaez: Although Eric has been a startup CEO, his current firm is not a startup that he founded. He never had a mission to be a CEO, but he was always looking to make a buck from his teenage years and he does not like to take orders from others – so CEO is the answer for him! He held odd jobs to pick up the money as a youngster and learned a lot on his way to becoming the boss. Eric is a learner and shared that he loves working remotely!

Tony Lewis: Tony is in his seventh startup company, with six exits in companies of different sizes. Tony feels that he just fell into the CEO role without thinking about it. He started a company, and “boom” he was CEO. He learned from mistakes, listened a lot to others, asked a lot of questions, and over time the experience drives his leadership skills. Tony is from Wisconsin a proud Green Bay Packer and Milwaukee Bucks fan. He offered as well, that his nine children contribute joy to his life and career. Tony shared that what he learned about himself from the pandemic lockdowns, is he does not like to travel like he once did!

What’s next in the series

In the next two installment of the CEO Insights Panel, we will share each CEO’s perspectives on day-to-day focus and priority setting, what some of their worst and best days looked like, advice each CEO might give today to themselves in their pre-CEO days, tips and advice for aspiring CEOs and leaders, and their final words.


This is the first of three blog posts in my series of discussing the CEO Insights panel. The series will be posted in the coming days, and is intended to provide a solid foundation for those interested in what it’s like behind the scenes of a seasoned CEO in the tech space today – in this case, all companies are SaaS or SaaS product related.

I hope you enjoy this series, as the panel was truly both entertaining and educational with many great tips and tributes to CEOs and aspiring CEOs.

Thank you for stopping by the CEOInsights blog, and I hope you come back soon for new content and the remaining installments on this panel.

CEO Insights Tip:

There are a number of guest CEO Tips on this blog site, many from current CEOs of other companies, and some from me. Please check out the posts, and share on social media, I would appreciate that.

I would also refer you to my book, with the link above, which is available in eBook, paperback, hardcover, and audiobook formats. All formats are on Amazon, other print formats can be found in various online bookstores such as Barnes and Noble, Walmart, Target, and a myriad of other online sites. The audiobook is available on Amazon, Audible, and Apple books.