I Am Very Proud of the Breaking Changes Podcast

My time at Postman came to such an abrupt end I haven’t had time to properly assess all the work I did during my time there. I just had brunch with my partner in crime LeTroy Gardner and his partner Joy, and a flood of memories have come to the surface. To help me work through I wanted to write about my time creating and producing almost 150 overall episodes of the Breaking Changes podcast I did while working at Postman. I am very proud of what I did with LeTroy, and haven’t really had time to sit back and reflect on what LeTroy and I made happen.

I wanted to unpack a little bit about why I am so proud of Breaking Changes, and make sure I take away what truly mattered to me, so if I ever do another podcast I can make sure I build on the momentum of Breaking Changes. The title of Breaking Changes was great, and something I don’t think we ever lived up to in the show, but I was trying to distill down into the types of questions I asked of my guest a sense of what mattered moving forward with APIs within an enterprise, while acknowledging our legacies. Here are some of the areas I walked away from the show feeling like I did good work, and will be something I carry forward in any other work I do in the future.


The number one topic of discussion across all of the shows I did was about the productization of APIs, which focused on bridging not just business and engineering within enterprises, but also establishing more meaningful consumer feedback loops. I left the show with a strong awareness of this need across many different industries, and is something I continue to wrestle with alongside API governance. I feel like this is the greatest challenge facing enterprise organizations and will continue to reflect on the quality and value of products and services they produce, but also strongly underpin how successful they are within the world of AI.


Coming in number two, and shaping where I went after leaving Postman, was API governance. I heard many different views of why API governance was the top priority of enterprises, which has continued to shape my definition and approach to API governance. I realized during the show that API governance was rarely about what vendors focused on with API design and automating rules and policing in pipelines, and was mostly about people. The API governance conversations I had across Breaking Changes is the basis for how I approach API governance going forward, and is a conversational pipeline I’d like to fire up again.


With season two of Breaking Changes, and with LeTroy’s assistance I was able to truly bring a diverse range of voices to the show. I feel like this was the lifeline for the show, but also a nutrient pipeline for my own transformation as I worked to deprogram myself after the Trump administration and during the pandemic. The diverse conversations I had on the show confirmed for me that many of the problems we face in tech could be alleviated if diverse voices had a seat at the table. Working and defining the voices we got onto the show also demonstrated for me the systemic and institutional challenges white women, women, and people of color face when operating within the tech ecosystem.


I had a couple of VCs on the show, while also producing a podcast at a well-funded startup. I learned a lot through these conversations and processes, and provided me with another advanced lens to look at the world of APIs through. Nothing is as it seems in this topsy-turvy world, and it is something you just have to learn along the way. I don’t think there will ever be a textbook that captures the positive and negative forces at place when you dance with venture capital. While much of the money side of these discussions left me yawning, the storytelling that occurs, and the power in which it holds over all of us is something that continues to fascinate and stun me as I make sense of the API landscape.


I received another significant dose of awareness regarding how the technology, business, policies, and people of the enterprise influence APIs, and the applications and integrations they power. The struggles of scale within the enterprise pertaining to API products, governance, and diversity above really caught my attention in the conversations I had on Breaking Changes. So much so, I ended up leaving to join an enterprise. The enterprise at scale is where the next wave of API solutions exist, and I needed to get more of the grownup view of this I was hearing in the conversations I was having on the podcast—because this reflects the future of APIs beyond the teenage years we are emerging from today.


I learn so much talking to startups. I learn so much from the smart people LeTroy lined up, and the diverse range of industries they operated in. When you switch from enterprise conversation one week to a startup conversation the next week you learn a lot just by contrast. When you ask about API design from a large company like Disney or Fedex, and then you ask about API design from seed stage startups, you can get very different answers. There are a lot of lessons in this diff, and when you contrast with venture capital and analyst views of things you can come away with a lot of awareness around how startups are just complex financial products that are combined into derivatives which drive each wave of tech.


I thrive on the honesty I was afforded for the most part on the show. I get to have the real conversations, and ask the questions that I felt mattered. I didn’t stick to a script. I found the guests that required questions up front were rarely the good shows. Honesty from host and guest is what seemed to build trust on the show, but then also with listeners. When and if I do another show in the future it will have to be 100% this. I want to be able to take the conversation anywhere it needs to go, even if it makes the host, guest, and audience uncomfortable. The tech space needs more of this, and less pandering. I am playing around with in my head different formulations of how this might play out for my future conversations.


I really enjoy listening to people. I love being in a space where I can truly listen, and not pretend to listen. As a white man I have done enough talking. If I am going to be the host I want to give the platform to my guests, and just be there to steer things in the right direction with thoughtful questions. I learned a lot from the diverse voices that LeTroy lined up for me. Looking at the cast of characters in season one and season two understand my approach to finding guests and LeTroy’s approach. It is stark. It made all the difference.


APIs are everywhere. I took some flack for talking to people who were not always one degree of separation from APIs. The people who put APIs to work, and ventured into more of the business realm. This was something my more hardcore tech listeners didn’t always appreciate and would let me know. They are wrong. This is the future of APIs. Hell, it is the present of APIs. The fact that the faces and voices I was talking to didn’t look like you, and the topics weren’t focused on the technology of APIs, demonstrates how blind this audience segment can be to what the future holds. Us tech bros are good at defending our turf, but the world is changing and we need more voices in the API conversation because they are everywhere.

Long Term

Breaking Changes provided me with a healthier long term view of the API landscape. Something I don’t think many folks can achieve down on the API factory floor, or lost in the API hustle on the streets. I learned across the enterprise, startup, and venture conversations more about just how short-term decision making dominates the landscape. Most people involved with delivering APIs are focused on near term value generation and extraction, and not building generational wealth across the tech sector. After you talk to enough hustlers and hard workers you begin to easily see who is in for the long haul, and who is just looking to get attention, tell a good story, and benefit whatever their current hustle is.


I learned so much about leaving a legacy talking to folks on Breaking Changes. I went from talking about our legacy technical debt to considering how your technology can still be used in 20 or 30 years. I found some of the conversations I had about enterprise legacy to some of the most revealing regarding the current state of business across the tech sector. The way an organization and its employees view their technical legacy and talk about it will tell you everything you need to know about the future of that business. This is another topic that haunts and sticks with me like productization, governance, and the other areas listed above, and will be something I continue to explore across many different business sectors.


It is really hard to establish, communicate, and stay true to a strategic vision in the world of APIs. APIs are really hard to see, yet they also represent all of the knobs and dials that executive leadership will need to turn to steer the enterprise vessel in the right direction. The API factory floor is extremely noisy and it can be very difficult to find the peace of mind and awareness you need to properly craft the right strategy. This is by design, although it has occurred accidentally, or through a series of externally orchestrated accidents. AI is just one of many accidents that have occurred over the years, making things noisy. The alternative is to retreat to your ivory tower to craft your strategy, where you will ultimately lose touch with what actually is occurring down on the factory floor, let alone the street.


You can see hints of where LeTroy was taking things towards a larger and much more mainstream destination. Riot Games, Special Olympics, Boy Scouts, American Cannabis, and The Trevor Project all have these fingerprints on them. If left inhibited, LeTroy would have doubled or tripled the audience with the next season. I learned a lot talking to some of the people he lined up who never even made it on the show. Some who did, I got pushed back on. I learned a long time ago that there are only so many API conversations you can have within the echo chamber and you need to explore interesting and not so interesting conversations to find where you need to be to elevate into the mainstream. We came close. Maybe next time.


Breaking Changes was the highlight of each of my very busy weeks at Postman. My team was 45 people, with 15 direct reports when I left Postman. I was also the face of the company with all of our largest enterprise customers. My notebook from Breaking Changes conversation that never happened, the ones that ended up being published, and from the conversations I was having with their largest enterprise conversations is fascinating. There is so much to learn there. Breaking Changes even had an API for accessing the transcripts from each show, and all of the topics that were discussed across each show, so that I could easily pull up references for blog posts, or find where I was deficient for planning upcoming questions I’d ask new guests. Breaking Changes was (and will continue to be) a rich space for me to learn about APIs.

I am extremely thankful for LeTroy, and all the guests he brought on the show. I guess I also have to give some credit to Postman for making it happen. However, I think that the show became so rich because of LeTroy’s hard work to find guests. He convinced some people who were very shy or skeptical to come on the show. He took to heart when I said I wanted to break out of the echo chamber and bring diverse voices from around the world. While I can highlight other meaningful things I did while at Postman, something I will do in another post, I put Breaking Changes at the top of the list. I would say that I have learned so much from 2010 through 2020 as the API Evangelist, but what I learned from Breaking Changes and the enterprise API conversations I had as Chief Evangelist at Postman are equal to the previous decade—-something I am continuing in my current role.

Thanks LeTroy. You rock!! This time meant a lot to me. If I ever get another chance to work with you I will. I count 136 Breaking Changes shows in my local folder, with 26 from season one, and 110 from season two, and I know there were more that I didn’t properly log. At some point I will index the content again so that I can search across it for references in my future storytelling. After the body of work I call API Evangelist, Breaking Changes season one and two represent the second greatest body of work I have created. Both of which will define the next couple of decades of my career, and hopefully influence things even once I retire. I am going to take everything I’ve learned on the show and continue applying in my day job, but I am also exploring what will matter the most when it comes to my API Commons, APIs.json, APIs.io, and API Evangelist work which is all intertwined with all the stories I explored in my Breaking Changes conversations.