The Moment When Everything Changed

I wanted to share our surprising journey of becoming a top ranked podcast. Our podcast strategy has changed multiple times; and we have learned and iterated. Over 250 recorded episodes, multiple partners, and key lessons learned. It was not an overnight success. 

From Burst Appendix to 3 Big Goals (Destinations) 

I started the Measure Success Podcast, wrote Lost at CEO, and ran the San Diego Rock and Roll marathon because those were the three big goals that I created to motivate myself to recover from my burst appendix. During that long week in a remote hospital in the middle of COVID, with an NG tube down my throat for four days…well it put a bit of perspective in my life. I was once again reminded that life is short. And if you don’t start doing things now, they will never happen.

The podcast was the first of the three goals that got accomplished. 

As in most cases, when I start something I want to accelerate its success. I reached out to experts and found, I now call a friend, Dr. Jeremy Weisz from Rise 25 and he helped me build the Measure Success Podcast from scratch. 

Rise 25 was fantastic. They help me set up the framework for the podcast, professional music, speaker, tech stack, listing, and how to prepare for great interview questions. They provided excellent coaching to help get it launched. 

If it wasn’t for Rise 25, I would have never built a foundation to become a successful podcast. I’ll always be thankful for them. 

One of their recommendations is to have people on your podcast who could potentially be clients. What a great way to establish rapport when interviewing them versus trying to do a cold call. 

I started with this process and it frankly had little success. I don’t think I had anything to do with Rise 25. It just felt like this was not the real reason why I started the podcast. After all, it was called the Measure Success Podcast and I was generally interested in learning how successful people define and create success for themselves and to teach others how to do the same. How do you measure success? How do you help build great companies? How do leaders measure their own success?

Looking for Guests

In those early days, it was hard to find somebody to be on the show. I think a lot of that had to do with the fact that I was doing the podcast for my own benefit, and not the guest. I was trying to get people to buy me, as opposed to why they were coming on the show, which was to talk about their life experiences, business success, products and/or services. One of the best tips that I heard from a podcast guest, was just simply ask your current podcast guest if they have somebody that they’d highly recommend to be in the show.  And with that, the quality of guests really started to improve. We began to get people on board.

We were able to get to a point where we had a four-month backlog of guests, therefore, we had cracked the guest code.

Creating a Quality Guest Experience

But the conversations did not really start improving until I made one huge key change.

NO MORE SELLING. No more prospects. Just build a great show. 

BE CURIOUS. Connect with the guest.

I had established a few key questions that I generally ask in every show…but my goal is to connect with the guest. Get them to a point where they have to think, go deep. Provide insights they do not typically share. Sometimes the show gets emotional where our guests go. That means that I have to listen intently to ask questions based on what they are saying to understand them more.

Over the last 75 episodes, I regularly get feedback from the guests that this show was different and they appreciated that. They tell me that I ask great questions. That has been very rewarding. That was the 2nd code that was cracked. Create a great product, or in this case, podcast.

After the show, they get to pick Measure Success or 40 Strategy Swag and we send it to them through our partner GearUp Sports. It's very cool when they send pics wearing their shirts, sweatshirts, and some say they wear it all the time.

Creating a Podcast with Impact

My second reason for building a podcast was to educate our audience and make an impact. One of our core missions at 40 Strategy is to positively impact over 1,000 business owners directly and 10,000 businesses indirectly during this decade. I felt one of the best ways to measure that impact was becoming a Top Ranked Podcast, in particular, a Top 100 Podcast in our genre. We had been rated a Top 2% global podcast, but not in the Top 100.

Therefore, I changed my podcasting team to two different offshore groups who worked with some of the most popular business leaders in the industry. I had listened to some of their clients speak at large conferences, they appeared legit. Unfortunately, I learned that a lot of popularity is purchased. Yes, we definitely improved our social media quantity and quality and picked up more downloads through the process; but I was not interested in just buying popularity. Therefore, I stopped the process.  

And, we had still not cracked the top 100. 

(Picture: Just a few of our guests: Mark S. Lewis,  Dr. Amir Rashidian, Crystal Mosser, Paul Menig, Dane Groeneveld, Kris Ward, Norman Wolfe, Antoni Lacinai, Isabelle Mercier, Rob Bier, Trey Taylor, and JM Ryerson) 

Launching the $4M Strategies Podcast 

So, I hired a third firm because they were the experts on becoming known and they had incredible successes with social media expansion. We even launched a second podcast, the $4 Million Strategies podcast. 

This was awesome because of the amount of different people that we talked with! They started to provide real tactical advice on how to fix problems within a company. Our content started to really resonate and grow with our audience, and provided extra value for the main podcast. 

However, my time and energy and not to mention expense, was growing at a clip that did not seem to bring the return, or necessarily accomplish the goals that I was trying to accomplish. 

But still Not There

And once again, we did not crack the top 100.

So with the advent of technology, particularly moving to Riverside, and using some of the tools built right from it with our existing team members. We were able to skinny down the technology around the podcast and continue to focus on having great guests and meaningful conversations. Our audience, and myself were able to learn something from each podcast, where we can help teach others about measuring their success, business, and their life.

I will admit, there were times that I had become discouraged that we will never hit the top 100. We were not going to put in the dollars, the resources, into other organizations (i.e. buying the addresses necessary, etc. to get to that next level).

But, we did not quit. We kept moving forward. Every week, create it, ship it!

The Unexpected Surprise

After doing a couple hundred episodes of the podcast you begin to develop your style, your approach, you become more comfortable behind the mic. The $4M Strategies podcast helped expand that experience and connection with great business leaders. 

Apparently, our reputation, our consistency has spread. Today, we get 2 to 3 requests on a daily basis to be on our weekly podcast. 

Today we are rejecting far more podcast guests than we are accepting. 

But the Most Important Thing

We changed our focus on just creating a great podcast, to learning to become better at business strategy and execution. We continue to create great value and we have created an amazing network of people within our community that I didn’t have three years ago.

The #4 Rated Strategic Planning Podcast in 2025

So Million Podcasts rated us as the #4 ranked podcast behind a few experts. I was absolutely overwhelmed!

We were completely unaware of the rating. We didn’t apply for this. An independent third-party validated the hard work that we’ve put in since 2021 and the 222 Measure Success Podcasts we have released so far.

We not only reached, but exceeded our goal. When I came across the announcement on LinkedIn, I was emotional about the award.

The irony is that the award came, after we stopped trying. The goals came after we stopped trying.

The sales came after we stopped trying.

Five years later, we continue to build a podcast with integrity. To create the best experience for our guests and our audience.

Thank you to all of our guests, to everyone who supported the process along the way, and to Tonya and Erin who have helped us create this top rated podcast.

What we learned is, if we create great value, and create a great experience for our guests, we can create a top strategic podcast. We have developed brand expertise, an amazing network, and ultimately a podcast that can now Measure its Own Success, #4. We are rated with some of the most respected names, such as Build with Leila Hormozi, Scaling Up Business with Bill Gallagher, Poised for Exit with Julie Keyes, and my friend Anthony Taylor with Strategy and Leadership Podcast.

And finally, and thank you to our guests! We appreciate the feedback and your support along the way. We would not continue to be here if we were not making a difference for you.

As we finish with every podcast, “Wishing you the very best in measuring your success, have a great day!”