As a listener you may already know the general background story of The Flip's origins. In short, I wanted to learn more about African entrepreneurship, in-depth, and struggled to find what I was looking for. 

As I had made a commitment to start this project, I reached out to my friend Sayo, the founder and CEO of a Johannesburg-based startup Kandua, to conduct the first interview. We never did anything with that audio - the quality was poor and it was just a chat amongst friends, but it laid the foundation for Sayo and I to work together on this project. 

Sayo is a big believer in the benefit of “archiving” - that is, how sitting down and having a conversation about a specific topic that he’s focused on can help him better flesh out his thinking. It’s the same reason why people write blog posts, I suppose. 

After that first conversation, Sayo immediately named himself my b-mic and committed to helping work on the show with me. 

This underscores the importance of being specific about the audience you intend to speak to with your content. This show is very self-indulgent. I was my own audience, because I wanted to learn from the content I was creating. But at the same time, working closely with Sayo made him my audience. As a venture-backed startup founder as well as an investor, his knowledge of this space and his desire for more in-depth, nuanced content forced me to push myself to the edge in terms of the quality of insights shared. 

Now, this actually wasn’t my first attempt at a podcast. A few years ago, before I moved to South Africa, I recorded around 20 or 30 hours with my grandpa - a hilarious and affable man with a lifetime of stories to tell - for a show that would be called “Spoiled and Senile”. This experience gave me a little bit of familiarity with podcasting and recording conversations, but unfortunately Spoiled and Senile, like so many other podcasts, went absolutely nowhere. 

I didn’t know what I was doing at that time and I had unrealistic ambitions for the show. I quickly became daunted with how to put my vision together and disillusioned with my inability to make it sound like NPR on the first go. One day, I really hope to pick that project up again, and with the lessons learned from The Flip, I feel way more confident in my ability to see it through and create something special. 

I bring that story up because I think it’s important to acknowledge that The Flip wasn’t my first attempt at podcasting. I had already failed once, and that experience, to a large degree, laid the foundation for The Flip. 

Another past experience that has proven to be an invaluable building block is my experience blogging on Medium. Like so many other entrepreneurs, I went through a phase of consuming a lot of entrepreneurship thought leadership, and there came a time when I needed to stop reading and start doing. Blogging on Medium was one manifestation of that, and it started with a 30-day blogging challenge.

Writing more not only made me a better writer (obviously), but more importantly, it got me comfortable with shipping my work. With the benefit of hindsight, this experience was absolutely crucial for my podcasting journey. 

There’s a concept known as “the adjacent possible”, coined by Stephen Johnson in his book Where Good Ideas Come From. It’s a term used to describe innovation within the realm of possibilities at a given moment in time. Disruptive innovation is constrained to existing knowledge and technology. For example, M-Pesa wouldn’t have worked in the early 2000s. Mobile phone technology and data connectivity in Kenya was a prerequisite to mobile money’s ubiquity. 

Similarly, I feel that my past experiences and knowledge gained were requisite stepping stones on my podcasting journey, and The Flip could not exist without them. 

On Show Format

I knew that the show would include insights and contributions from entrepreneurs around Africa. I felt, however, that format was important to differentiate The Flip from existing content, both locally and globally. 

Most podcasts are interview-style shows - they’re the easiest to produce. Some of the most popular podcasts, in general, are what’s known as “cult-of-personality” style shows, in which the audience tunes in because of the personality of the host and/or their guest(s).

There are interview-style shows in the startup and entrepreneurship space, and the strength of their show is typically built off of the relative experience of the guests, and in the host and guest nerding out and going deep into relevant subject matter. 

Early on, I felt that I couldn’t produce this type of show, and for several reasons. 

First, I am cautious about insights from "professional speakers" - those who talk about the thing but haven’t done the thing. I wanted the show built by first-hand experts, but I was afraid that, given my lack of track record in this realm, I wouldn’t initially be able to attract the type of interviewees I was hoping for. I didn’t want the show to merely be a platform for people to pontificate, or for two bros to sit and have a chat that no one wants to listen to (more on this from a production standpoint later). 

To combat this, I thought a lot about other shows I liked, and one show stuck out  - Freakonomics. In particular, I liked how Freakonomics covered one theme and utilized insights from an interdisciplinary set of individuals that made each episode greater than the sum of its parts. 

To pursue this show format further, I actually sat down and took notes. How did the show’s host, Stephen Dubner, introduce each episode; where did they transition; how did he use his voiceovers to set the narrative and move the conversation forward? 

It was audacious to pick this show format as an amateur podcaster - and the reality is, it’s way more work - but I felt strongly that it would make for a better show, and I felt emboldened by studying existing episodes that I could put it together. 

One other piece of the show format that people seem to really enjoy is the conversation Sayo and I have at the end. That concept was borne out of coincidence. I was testing podcast recording software for remote interviews (more on that later, as well) and asked Sayo to test it out with me. We ended up having a lengthy conversation about the content of the first episode, and it became clear that our conversation would make for an interesting contribution to the show. In fact, these conversations have become an integral part of the workflow of the show.

One other huge benefit of this format is that the work required to put an episode together makes it a great active learning experience. Back to Sayo’s reverence for archiving - the Freakonomics style format forced both of us to think deeply about each episode; to not just take what people were saying at face value, but to try to get a level deeper, and explore key ideas that were raised by an otherwise diverse group of individuals.

And, the initial goal of this podcast was for me to learn, so while I wouldn’t advise pursuing this format from a workflow perspective, the show itself has been an excellent mechanism for learning.

Selecting Episode Topics and Interviewees

Though I determined that the show would be thematic, I started by selecting individuals that I thought would be interesting to talk to. Admittedly, my initial outreach lacked strategy or tact - I interviewed a lot of people without an idea of how they would fit into the episodes or themes.

That was a lesson I learned the hard way. While I do generally believe that creative work is iterative and non-linear, I’m now much more intentional about who I reach out to and the topic(s) that I’d like to speak to them about.

While it’s hard for me to pin down a particular reason why I reached out to any one entrepreneur early on, I think a lot of it was driven by preconceived notions about what people would talk about.

The overarching theme of the show is that doing business in Africa is different - hence the name The Flip, as we’re flipping the script on pervasive narratives on African entrepreneurship and challenging the ubiquity of Silicon Valley thought leadership - so I was looking for people who could speak to the environment being different. 

My first interviewee was SafeBoda’s co-founder Ricky Rapa Thomson. I was excited to speak with him because he was a former boda driver himself and I was really interested in the nature of a tech company being started by a former boda driver, who could advocate for the needs and wants of boda drivers on the supply side of a ridehailing app. 

Another early interviewee was Erik Hersman, a serial entrepreneur who is currently the CEO of BRCK. The company makes “ruggidized” connectivity hardware for developing markets - they started by asking why we’re using Internet routers from the US or the UK when the infrastructure in Kenya is completely different. BRCK was another obvious example of a company building products and services for the local context. 

I knew that I wanted the first episode to be about taking the “worm’s eye view” - building relevant companies by getting as close to the customer to best understand their problems and create solutions that they’ll pay for. The concept of the “worm’s eye view” was taken from Nobel Peace Prize recipient Muhammed Yunus, who wrote in his memoir, Banker To The Poor, about how spending time in the villages with the poverty-stricken in Bangladesh gave him insights that led to the development of microfinance and Grameen Bank. 

Now we call it design thinking, though surely it was a novel concept when Yunus started back in the 1970s. But the reality is - and this is very much an inspiration for the podcast - there are too many instances of people thinking that they can create value in Africa by taking an existing model from elsewhere in the world and copying and pasting it in local markets. It doesn’t work that way, and I wanted to speak to the people who were doing things differently. 

As I continued to interview more people, and have continued conversations with Sayo, additional themes and episodes began to present themselves. Now, I have an ever-growing list of topics I’d like to cover and can more strategically reach out to entrepreneurs who I believe will be able to contribute valuably to these topics. 

Workflow

My workflow is nasty. There’s no other way to put it. It’s a hard format, made harder by the fact that each episode has several contributors. Apart from normal podcast workflow, I’m having to balance schedules of very busy people and ask them to give up an hour of their time to have a chat with me. It’s not easy… but it’s worth it. 

Pre-production

Once an interviewee has agreed to participate, we schedule an hour for the conversation, and for me, the work begins. 

I try to go into every interview as informed as possible. That means reading up on the interviewee and the interviewee’s company - blog posts (especially if they’ve written blog posts themselves!), news articles, other interviews or videos that the interviewee participated in, and so on. 

For two interviewees, GG Alcock and Feyi Olubodun, I even read their books (KasiNomics, KasiNomic Revolution and The Villager)! That may have been a little extra, but again, I am optimizing for learning through this experience. 

From there, I put together a list of questions and talking points. Ideally, these talking points are addressing the topic(s) for which I’d like to include the interviewee, but the interview itself ends up being a pretty open-ended, free-flowing conversation.

If the interviewee asks, I’ll send them the questions in advance, but most times I do not. It’s probably a bit better that their answers are not rehearsed, though the reality is much of what we talk about is pretty intimate to them and they can speak to it in their sleep.

Production

I’ll get to tools and equipment later on. That’s not as important as how the interview is conducted, and the environment in which it’s conducted. 

If I had to pick one trait that I think is most important for a good podcaster, it’s curiosity. I find myself genuinely and deeply curious in what the interviewees have to teach me about their business and their experience. Especially as an outsider to this ecosystem, I feel that there is so much to learn and these conversations are a tremendous opportunity for me to do so. 

I think curiosity is what makes a good interviewer, and subsequently what creates engaging conversations that are full of insights and intrigue. Having genuine, interesting chats in a comfortable and friendly environment also makes the interviewee more comfortable, especially if they are not as experienced in doing interviews or speaking into a microphone.  

From a how perspective, the most important element is a quiet environment. It’s so important for audio quality not only that there’s no background noise, but that there’s no weird echos or other elements that might negatively impact the recording. 

This is easier said than done when doing remote interviews. For that reason, I send each interviewee a checklist of considerations to ensure the best audio quality. For a remote interview, the list includes using headphones and being on strong wifi.

Another important thing to remember while interviewing is to hit record. I have forgotten a few times, and it’s sad to lose what otherwise would have been great content.

Post-Production

For our regular, thematic-style episodes, 75% of the work occurs in post-production. 

The first thing I do is transcribe interviews. Yes, I listen back and manually transcribe each hour-long interview. Yes, I know there are transcription tools that I can use to make this process a lot easier. 

Manually transcribing is an integral part of my workflow, first and foremost, because I find that it really improves my recall and helps to further ingrain the insights shared by my interviewee. It’s very easy to miss a nuanced point when conducting the interview, and while listening back to the transcription I often pick up a point that I didn’t fully appreciate during the interview. 

Transcription also makes the script-writing process for each episode much easier, as  the transcripts are a searchable tool with timestamps, and it’s much easier to find quotes compared to searching through an hour-long audio file.

As I mentioned, Sayo and I have a recorded conversation on each episode and theme. We actually do this in advance of the editing, because the conversation and his insights greatly help me with the narrative for the episode. I’ll share some insights from the interviewees - I may even read direct quotes from the transcripts - and like two sculptors we’ll chisel away to a more finished product. The majority of these conversations are not usable content for a public audience - it’s a lot of Sayo telling me my ideas suck and me defending my ego - but what is useful ends up edited into the final conversation you hear at the end of each show. 

For each episode, I write out a script. It’s comprised of the quotes we want to include from interviewees, as well as my voice overs to narrate and help guide the episode along. Since the quotes from interviewees are fixed, there’s a lot of creativity that can be applied to my voiceovers to help drive home a point. I tend to write my voiceovers out just like any blog post, and over time have tried to improve upon this writing by making it more concise for audio format.

The scriptwriting process is where the majority of our editing takes place. It’s an exercise in being ruthless in cutting and making clips as concise as possible. I’ve learned to better recognize, in advance, how much should be cut out to ensure that clips and insights aren’t rambling on. 

Sonal Chokshi, the producer of a16z’s podcast, talks about insights per minute as a metric they use. While I’m not counting insights, I try to take this to heart and get to the point as quickly and efficiently as possible. When in doubt, cut it out.

Another one of the most important pieces of advice I have - do not skimp on audio quality. No one wants to listen to bad sounding audio, or interviews with a lots of um’s and ticks. I hired a professional audio engineer to handle the technical production, and you should too. 

Once the script writing process is finished and I’ve recorded my voiceovers I send the script along with all of the raw files to my editor. He takes the script and turns it into a finished product, which includes mixing and mastering to make the audio quality as high as possible. 

To be sure, audio quality starts with the recording itself. There’s limited things an editor can do if you’re in a noisy environment. 

But for me, my editor is invaluable, because I simply lack the technical ability, especially given the complexity of our show from an editing perspective, to create a final version of this show. 

Once my editor gets me back an air ready file, there may be a round or two more of edits before we get to the final version. I share with the interviewees as a courtesy, should they want to listen back before we publish. I have scarcely had any edit requests, but it’s a nice thing to do. 

Publication

I have a production and release schedule for my show. I publish on Thursday mornings. There’s not really any rhyme or reason why I picked Thursday. It just felt good. I should probably A/B test this, but the reality is that there’s quite a long tail with this content, and I suspect the majority of people don’t listen to a podcast immediately anyway, so I don’t really think the day or time that we release matters that much. 

I have a checklist of things that I need to do for each show. It includes writing show notes, creating episode graphics for the show and social media, uploading the show via my podcast host (which in turn distributes the episode to Apple Podcasts, Spotify, Google Podcasts, and all of the other platforms), creating a new post for my website and creating new contributor pages, when necessary. I also repurpose the show notes copy for a newsletter, as well as posts on social media, and always ensure to tag the interviewees and their companies so they can help spread the word to their networks, as well.

Equipment and Software

This is what everyone asks about, but as I mentioned earlier, it really is less important than everything else I have outlined. My equipment is probably middle range - there’s definitely more advanced and professional microphones I can use, for example, but I really don’t find it a necessary expenditure at this point. Also, I don’t have a permanent studio, so I’ve optimized for portability (while being mindful of quality) over anything else. 

Equipment

When I do in-person interviews and my voiceovers, I have a mobile studio that I use. Again, it’s most important to be set up in a quiet environment, so I will often ask interviewees to meet in a location of my choosing as opposed to visiting them in their offices, to ensure a quality environment. 

Here's what I use -

Zoom H5 recorder
Shure SM58 XLR microphones
XLR cables
Desktop microphone stands

I also have a Blue Yeti USB microphone that I occasionally use when conducting remote interviews on the computer.

Software

When recording an interview remotely, there’s dedicated recording software I use. You can use Zoom, which has great connectivity for a VOIP call, but it does not create as high of quality audio recordings as dedicated podcast recording software. The key is obtaining audio files in .WAV format, which is higher fidelity than .MP3. 

Again, ensuring you and your guests are in a quiet environment, and that your guest is using headphones or, ideally, a microphone, is more important than software you use. 

Simplecast - my podcast host, which handles distributing each show to all of the podcast networks, gives me an embeddable player for my website, as well as listenership metrics.

SquadCast - remote podcast recording software.

Zencastr - this was the first remote recording software I used, but they had a bug one day that lost two of my interviews so I left them for SquadCast. 

Other software in my tech stack includes Descript, which I sometimes use for rough edits and have increasingly used for recent interview-style episodes, Mailchimp for my email newsletters, and Notion for literally everything - workflow and to do’s, podcast notes and transcripts, and much more. 

What does success look like? 

Invariably, the question I get now that the show’s been launched is how many listeners do we have. It feels good to watch the chart go up, but listenership is clearly a vanity metric - even more so when acknowledging that this is a niche show for a niche audience. 

For me, I prefer to measure success by trying to understand how the show is being received by the type of person I’m creating the show for. If those with more experience on the continent, and who are trusted, esteemed entrepreneurs in their own right are listening and finding value from the content we’re creating, I know we're making the right kind of content. 

A discussion on measurement goes even further by asking what you’re trying to achieve with a podcast. Undoubtedly, that’s different for The Flip than many other shows. Measure accordingly.

In Conclusion...

…there’s much more to podcasting than meets the eye. I learned this the hard way. But investing the time and doing the things that scale, as they say, makes all the difference. For me, this includes research and production, as well as audience development and engagement. 

While I’m very early in my podcasting journey, it has been an incredible mechanism for both learning and meeting people, and is something I’m excited to continue to do and to grow as long as I’m creating value for listeners. 

If you’re thinking about starting a podcast, I’d caution that it’s hard work, but would absolutely encourage you to go for it. I’m here as a resource if you need!