From Founder To CEO

Nick Symmonds didn't have all the advantages that athletes at top tier schools had, but that did not stop him from becoming an Olympic athlete, twice! And, Nick's can-do, work hard, never-give-up, Olympic attitude has translated into the building of a company that is changing the way athletes approach performance. You'll be inspired by his grit and the candid conversation we had during this interview. He discusses:

• The challenges of shifting from an individual, Olympic sport to the team sport of business
• How his need for structure competed with the need for startup flexibility and patience
• Why role clarity is so important as your startup grows
• How getting his team outdoors helps them overcome overwhelm

Fred is a Founder & CEO who just gets it. As the Founder & CEO of IntroAgent.com, he understands the mindset of the Founder. That's why he created VentureFuel. He wants to helps Founders grow their company by connecting them with the right, big brands. 

Fred was a lot of fun to interview because he is also not afraid of getting vulnerable and sharing about his own challenges shifting from Founder to CEO. He gets personal about:

1. The challenge of actually charging clients for his work...and the ensuing cash flow issues of not doing so.
2. His challenges about "letting go" and building capacity in his team members so he can better scale himself.

Some of my fondest memories involved spending two weeks in the summer with my grandmother. We didn't go on fancy trips or do anything that required money or connections. We played games, went to the park, and my favorite...we visited the farmer markets, picked the very finest fresh foods, and went home and made amazing dinners together. You might say it was "farm-to-fork," grandma style.

So, when Erik Oberholtzer agreed to come on the podcast, I was thrilled. Erik is among a small number of inspired leaders pioneering "farm-to-fork" cuisine. His California based company is expanding, and with that he too is growing from Co-founder to CEO. Erik is a thoughtful person whose wisdom shines through in this candid interview.

You'll hear him discuss:

• Why "slow and easy" wins the day
• How his long-term thinking about partnerships has fueled his growth...and expansion plans into New York
• Why shifting from Co-Founder to CEO has been such an emotional experience for him personally

As for me, I can't wait until he brings Tender Greens to Cincinnati. ;)

Angelique is one of those Founders whom you say to yourself...just wow! Super smart, truly dedicated, inspirational, ready to tackle complex problems, and a wide variety of amazing experiences all combine in one amazing CEO. Angelique and her team are combining SaaS, with change management, with innovation, and with a deep understanding of cultures and how they react to re-invention.

Angelique talks about two really important issues that I am sure you have either struggled with or which you will probably encounter in the future:

1. Navigating "mentor whiplash"
2. Dealing with a major injury while still needing to perform as CEO

You can tell by Angelique's mindset that she is a winner.

Eric has quite the background. As one of the founding engineers and Vice President of Engineering at WebEx, he LOVES connecting people digitally. And, with Zoom he has created an experience that I have found to be truly magically.

Since we use Zoom for our Founder & CEO peer groups, Trail Team 10, I just has to get Eric on the show so you and I can learn more about the leader behind this great communication tool. With over 370 people on the Zoom team and over 320,000 customers, Eric sure is doing something right. 

In this interview Eric shares:

• Why he left Cisco to create Zoom
• His biggest leadership struggle
• And the one leadership skill he wishes he would have learned earlier

Andrea ("Drea") and her team inspire me. I have personally traveled the world and fully appreciate when I am able to authentically connect with the people of the region I am visiting. Drea's emphasis on authentic experiences rather than simply bus "drive by gazing," is a refreshing approach to a travel industry that is increasingly dominated by familiar experiences.

As she has built LocalAdventura, she has also experiences her own personal growth. In this interview she gets personal about:

• Why her favorite quite is from Margaret Mead
• How overcoming overthinking and over-planning helped her grow the company
• How using experiments and taking more risks were key to growing the company
• Why she invites other founders to speak with her team
• What happens when she sponsors team experiment competitions

A few years ago the wood swing set in our back yard had deteriorated enough for me to start worrying it may not be safe for my family. I knew it would take me forever to disassemble it. And, then there was the issue of what to do with all the pieces. So, I called 1-800-Got-Junk. It was gone in an hour. Wow!

After interviewing the company's Founder & CEO, Brian Scudamore, in this episode, I now know why my experience with 1-800-Got-Junk was so exceptional. Brian is exceptional. His energy, enthusiasm, attitude, are contagious and his entrepreneurial leadership is extraordinary. 

In this candid interview Brian covers:

• Why he fired almost all of his team leaders...all at the same time
• How he found his COO...and how you can too
• The evolution of COO hiring
• Why he only focuses on what he does well
• How to leverage a mentor
• Why it was so important for him to let go in order to scale
• Why it's important to trust in yourself as the Founder & CEO
• Why he believes in "leaders eat last"

Ry and his team at Astronomer have goals as big as the sky. You know all that growing data that you are having a hard time wrangling? Well, Ry co-founded the company that is helping you move that data to where it is needed and when it is needed so you can make better sense of it all. It's a harrowing task, but he and his team have made enormous progress. And, along the way, Ry has learned more and more about himself as a leader. He gets personal about:

1. Leveraging his sales strengths by getting Monthly Recurring Revenue (MRR) right from the start.
2. How he and his COO divide the responsibilities of leadership.
3. How he looks at maintaining a good relationship with his board.

Down to earth, but reaching for the stars. That's I sum up this interview with the fast-growth Co-founding CEO of Astronomer, Ry Walker.

Eric has a growing list of accolades that all reflect the growth and success of his company, Vacasa. He's a humble guy whose fast-growth company all started with his family's 1800s cabin. That experience combined with two great first hires, hard work, diligence, and an amazing team have all resulted in the 2nd largest vacation rental management company in the United States.

In this interview you'll hear Eric address some unique topics like:

• When he first realized he was actually a CEO
• How focusing on hiring friends and referrals has fueled Vacasa's growth
• How he handled leaping from individual contributor at Capital One to being the CEO of an over 1,000 person company
• How his tendency toward analytics has helped and hindered his journey From Founder To CEO

What's it like to found and scale the #1 cloud accounting software for small businesses and the self-employed? What's it like to work out of your parent's basement for three years while you grow your startup?  What's it like to wait ten years to accept venture capital money and conquer your fear of doing so?  What's it like to lead a growing company of over 250 team members?

Listen to Mike McDerment, the Founder & CEO of FreshBooks, in this revealing and candid interview as he answers all the above questions and more.

I was particularly impressed with his story about how greater self-awareness has been the key to his ability to scale himself as a CEO. My favorite quote: "I've got to slow down and actually be present in a way that is probably not natural to me."