Bert Weiss of Pionaire Podcasting: “Be OK with delegating”

Be OK with delegating. Mostly not, but sometimes I can be a control freak with business. Why surround yourself with the best if you’re not going to allow them to freely apply their craft? This is part of their business too. Allow them to invest and be creative and enjoy their work. I got so […]

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Be OK with delegating. Mostly not, but sometimes I can be a control freak with business. Why surround yourself with the best if you’re not going to allow them to freely apply their craft? This is part of their business too. Allow them to invest and be creative and enjoy their work. I got so good at this that at some point I sent out an email to my super capable staff reminding them that they have the freedom to make decisions without me and run with those decisions. I trust them, but I think I had trained everybody to run everything by me first. That’s not good for anyone.

Many successful people reinvented themselves in a later period in their life. Jeff Bezos worked in Wall Street before he reinvented himself and started Amazon. Sara Blakely sold office supplies before she started Spanx. Dwayne “The Rock” Johnson was a WWE wrestler before he became a successful actor and filmmaker. Arnold Schwarzenegger went from a bodybuilder, to an actor to a Governor. McDonald’s founder Ray Croc was a milkshake-device salesman before starting the McDonalds franchise in his 50’s.

How does one reinvent themselves? What hurdles have to be overcome to take life in a new direction? How do you overcome those challenges? How do you ignore the naysayers? How do you push through the paralyzing fear?

In this series called “Second Chapters; How I Reinvented Myself In The Second Chapter Of My Life “ we are interviewing successful people who reinvented themselves in a second chapter in life, to share their story and help empower others.

As a part of this interview series, I had the pleasure of interviewing Bert Weiss with Pionaire Podcasting.

Pionaire CEO & President Bert Weiss is best-known as host of the nationally syndicated The Bert Show, which has been on air for two decades and is in the top 5 most downloaded radio podcasts in the country. A Georgia Radio Hall of Fame inductee, Weiss is leveraging his content and delivery expertise in the launch of his boutique podcasting network. Weiss is also the founder of Bert’s Big Adventure, a nonprofit organization that provides a magical, all-expenses-paid, five-day journey to Walt Disney World® for children with chronic and terminal illnesses and their families.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I grew up in a super dysfunctional, dismissive family. Family connection was not a priority. The thing I’m most proud of in my life is doing the work to reprogram the unhealthy foundation my parents established for personal connection.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

Life is 10% situation and 90% how you DEAL with that situation. Everybody has experienced problems — but there are very few unique problems. How you chose to react to those challenges is the ONLY thing you can control. #novictimmentality

You have been blessed with much success. In your opinion, what are the top three qualities that you possess that have helped you accomplish so much? If you can, please share a story or example for each.

Blessed or earned? Wonder if there is a difference. I guess you somewhat earn your blessings in a lot of cases, right?

I love watching other people shine. In fact, I’d rather be a conductor than the doing the solo. Surround yourself with good people, control your ego, allow those around you to be the best versions of themselves and help along the way. I’m most proud when loyal, creative, hard-working Bert Show members leave the show, follow their own path and become successful.

The ability to pivot: I know the business model says you should have a one-, three- and five-year plan, but I take a more unconventional approach. While I operate with a loose goal in mind, I never get so laser focused that I miss opportunities that I never saw coming when they arise. The nonprofit I founded called Bert’s Big Adventure is a good example. It started as “just” a trip to Disney World with families that have children with chronic and terminal diseases. But soon we noticed that families needed to stay connected with each other when we got back from the trip, so we created a reunion program that allows families to remain in contact. We also noticed that some of our kids were ending up in the hospital for long periods at a time, so we developed a program in which any child from a previous trip ends up in the hospital, we have a volunteer who brings them gifts, spends time with them and gives the parents a break.

Creating your own breaks: Here’s a good example of my career long attitude. My first job in radio was as a research assistant at a country radio station. What did that mean? I made phone calls out and tried to recruit country listeners. It was a minimum wage job. But my end goal was to be a sportscaster. I realized that I could use the radio station letterhead and get press passes for ANY sports event, so I started sending out requests to NFL, MLB, NHL, etc. as the station “sports director.” There was no sports department — but screw it. Following the rules all the time is a losing proposition.

Let’s now shift to the main part of our discussion about ‘Second Chapters’. Can you tell our readers about your career experience before your Second Chapter?

I worked my way up in radio. From a researcher to a research director, to a morning show gopher, to a producer, to a sidekick, to a co-host and finally to host my show, The Bert Show. It’s been a career in morning radio that literally started grabbing coffee for the morning personality, and I’ve worked my way up through every level. The Bert Show is now syndicated nationally in 25 cities.

And how did you “reinvent yourself” in your Second Chapter?

It all came down to leveraging my experience. I don’t want to do morning radio forever, but I know myself well enough that I know doing nothing in retirement isn’t possible. I want to travel. A lot. So, I began to play with the idea of consulting podcasting talent. Podcasting shows use the same content and delivery principals as morning radio shows. I heard a ton of really talented podcasters that were missing entertaining basics to make their podcasts truly stick. The idea grew from a consultancy to a podcasting network. Choosing podcasters to work with, building a network of gifted creators, enjoying success with them and allowing them to be the best at their craft.

Can you tell us about the specific trigger that made you decide that you were going to “take the plunge” and make your huge transition?

It was really the idea of retirement. I envisioned a job in which I could travel but also work and be engaged. I can contribute to podcasters from anywhere in the world while continuing to be hands-on with Pionaire from any corner of the globe.

What did you do to discover that you had a new skillset inside of you that you haven’t been maximizing? How did you find that and how did you ultimately overcome the barriers to help manifest those powers?

Actually, I think I’m maximizing my existing skillset while simultaneously surrounding the network with podcasting experts who are much more experienced than I am. I know content and delivery. It’s where I’m elite. But podcasting is too intricate to learn quickly, so I’m learning each day from my partners who are experts in all other areas of the industry.

How are things going with this new initiative? We would love to hear some specific examples or stories.

Pionaire just started. We have three shows. House of Kim, which is hosted by former Real Housewives of Atlanta star Kim Zolciak and her husband Kroy Biermann. They came to us with a nice following established, and I’m really honored and lucky they chose Pionaire as their network. My Bert Show co-host Moe Mitchell has a podcast called In the Moement. He’s an extraordinarily gifted talent, and his podcast is solid start to finish — it just needs the right marketing. And the third show is my syndicated radio show, The Bert Show, which is getting almost 4 million downloads a month. At some point we’ll expand, but I want to make sure we’re operating at a super high level for our current shows before getting more ambitious. I want to remain a boutique network, so I’m being very selective about the shows we choose to bring on.

Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

There are SOOOO many. But I think the person that had the biggest impact on me was a syndicated radio host named Kidd Kraddick. I worked on his show for two years, but he became an older brother and mentor. He taught me so much about entertainment and life that his influence is with me every day.

Can you share the most interesting story that happened to you since you started in this new direction?

It’s so new, but I think the most interesting is probably the network itself. I was all set to have nice little consultancy, but I messed up and have surrounded myself with very ambitious friends. My business partner and friend, Chris Tuff, is a big thinker. He’s a “how do we scale this?” guy. He made me realize that the experience I’ve gained in my radio career can be turned into something much bigger than a consultancy. Then he pressured me into thinking bigger, so here we are.

Did you ever struggle with believing in yourself? If so, how did you overcome that limiting belief about yourself? Can you share a story or example?

The answer is a resounding yes. When I first started The Bert Show I was terrified that I didn’t have the talent to be a host. I thought maybe I was a good support piece. In fact, a General Manager at another station told me I’d never be a good host. I have a tremendous fear of failure. To be honest, it probably drives me more than the excitement of winning. Maybe it comes from a place of wanting to be accepted? I think the difference for me is that when I get scared, I still jump in. I don’t allow myself to ask, “what if?” That would be the worst decision.

In my own work I usually encourage my clients to ask for support before they embark on something new. How did you create your support system before you moved to your new chapter?

I don’t usually ask for support. I have a few good friends I trust who are fantastic at business, which is NOT my strong point. I’m creative. Not a business guy. But I surround myself with people who are great in areas where I’m weak. I’ll ask them to poke holes in my business idea. If my gut says yes, but they say no … business over.

Starting a new chapter usually means getting out of your comfort zone, how did you do that? Can you share a story or example of that?

Podcasting is a completely different field than radio broadcasting. The only thing that is the same is what I’m strongest at: content and delivery. So, this entire industry is out of my comfort zone. I was stressing about learning a completely different industry in a small amount of time. It wasn’t possible, but that’s where my team comes in: I’ve surrounded myself with the best podcasting marketers, engineers, social media professionals, etc. to work with clients while I continue to develop my expertise in these areas. It allows me to focus on my strength.

Here is the main question of our interview. What are your “5 things I wish someone told me before I started leading my organization” and why? Please share a brief story or example for each.

How to time block better!!! In the beginning I was scrambling from one task to the next, trying to get to one finish line just to start another task. I wasn’t good at any of them. I was just trying to get it done. Putting a structure together that allowed me to breath, have dedicated time blocks and sticking to them was incredibly helpful.

ENJOY THE JOURNEY. I refuse to fail. Sometimes there’s a price to pay for that. Getting frustrated by things that “don’t go as planned” is useless energy. Look, this is the last company I’m going to start. My business partner Chris reminded me of this and made it clear that being intrigued by unforeseen challenges is better than stressing when things go slightly off the rails. Remember that problems are just a blip in the overall picture.

Be OK with delegating. Mostly not, but sometimes I can be a control freak with business. Why surround yourself with the best if you’re not going to allow them to freely apply their craft? This is part of their business too. Allow them to invest and be creative and enjoy their work. I got so good at this that at some point I sent out an email to my super capable staff reminding them that they have the freedom to make decisions without me and run with those decisions. I trust them, but I think I had trained everybody to run everything by me first. That’s not good for anyone.

Know the numbers. This is one I wish I would have addressed 25 years ago. I don’t know how business numbers work. I don’t understand EBIDA. I don’t understand about taxes. I’m not good at budgeting. Do not be like me! You can be creative AND a good businessperson. I think I’ve lost hundreds of thousands of dollars over the years by not understanding or paying attention to the monetary side and understanding the spreadsheets I was looking at.

BALANCE. This is not possible. But try. Try and balance your life. Work life balance is the key to happiness. In my experience, most millionaires are not happy personally. They are driven professionally and have husbands or wives at home feeling alone. When you’re driven, it can be tough to shut the computer off and say to yourself, “it’s way more important to watch soccer right now with my kid than to answer 12 more emails.”

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

Start something that is important to you and that you have personal connection to the struggle. Are you a single mom who had to choose between feeding your kids or keeping the electricity on? You know that pain. Help women that were in your same position. Are you a man who grew up with an emotionally abusive dad that didn’t encourage any events in your life? Try to connect with that pain and pave some roads for others that you can help avoid your previous experience.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

Ed Mylett and Jay Shetty really inspire me with their podcasts. They have amazing insight into how to be successful but also … HAPPY!!!!!! Are you truly HAPPY and fulfilled?

How can our readers further follow your work online?

Visit or

Thank you so much for sharing these important insights. We wish you continued success and good health!

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