If you prefer listening over reading, you can listen to this episode of The Bootstrapped Founder on my podcast.
Today I want to share my learnings from a year of intense podcasting.
I’ve been publishing new episodes of the Bootstrapped Founder podcast for almost a year now, just shy of twelve months. At the same time, I have been a guest on more than twenty podcasts. Both hosting and appearing on podcasts has changed my life and greatly impacted my audience-building.
I’ll talk about how you can leverage being on shows and what advantages having your own show brings to your entrepreneurial journey.
Both being a guest and running your own podcast require particular kinds of preparation. I’ve been on shows where the hosts were under-prepared, and I’ve lacked in preparation myself. That’s why I am sharing this with you today. Bad podcasts can be avoided if we make the appropriate preparations.
You’d think that being a guest is fairly straightforward. You show up, talk about your stuff, and someone else does all the work.
That’s not the case. If you want your appearances on other people’s shows to make a difference, you’ll need to make sure that several things happen.
First, you need to be interesting. Not just as a person, but also in the context of the show you are being invited to. Many podcasts are heavily themed, particularly in the business podcast space. There are just too many shows to be general. So, many people who run successful shows have niched down significantly. Even the most popular shows like the Indie Hackers podcast are very selective in their audience and the people who get interviewed on the show.
Being interesting therefore has two sides: you need to be interesting enough to be considered for the show, and you need to have interesting things to say once you’re chatting with the host.
The good thing is that what gets you on shows is also what makes it easy to have a great conversation. And even better, you don’t need to be the most successful person in your field to be invited onto shows. All you need to do is enough to be on the radar.
I’ve seen this story happen a lot over the last year: someone commits to building a new business in public, documenting their journey. Even though they might not run a mind-blowingly successful business, they are so present in the founder community that podcast hosts who are looking for an interesting story can’t avoid running into them.
That’s the trick: you don’t have to be an expert yet. Showing that you’re actively working on it is enough. People enjoy listening to heroes in the making. I’ve listened to shows where people who were just preparing to get started shared their challenges and ideas.
Why does this work? Because shows serve particular niches. If you want to be on podcasts, you’ll have to find those that cater to audiences that would enjoy hearing stories like yours. Finding those shows requires a bit of research but can be reliably done by being part of the audience community. For indie hacking and bootstrapping, just following the most interesting indie founders on Twitter will expose you to many conversations that involve interesting podcasts. Transistor.fm, the podcast hosting service that I use for the Bootstrapped Founder podcast, has a page dedicated to bootstrapping-related shows. Follow the community, and they will guide you to the shows that might be a fit for you.
Getting on a show won’t happen magically. You will have to ask. You’ll have to build a relationship with the host. They should have at least heard of you or seen your name before you reach out to them. All of this requires being present and consistently engaging with the community. If you reliably create quality content and engage with people in a meaningful and uplifting way, you will be someone that people want to talk to on the record.
And that’s the core idea: a podcast is a journalistic endeavor that makes you a recognized part of a community. It’s the audio version of a magazine article; it’s a literal conversation between domain experts. Being featured on a show in your target audience will establish your reputation as someone worth listening to.
Here is why podcasts will help you build an audience: everyone in the space commonly consumes them. People listen to podcasts while they work, cook, do the dishes, or while they take the dog for a walk. People will put your voice to your face, strengthening their digital relationship with you. If you go on enough shows, people will eventually recognize your voice.
The second effect of being on podcasts is that you get to meet and converse with very well-connected podcast hosts. Leading up and following the taping of a show, you’ll be chatting with your hosts via email, establishing a pre-warmed communication channel that you can tap into at some later point. Podcast hosts know a lot of interesting people, and they are often quite happy to connect the people they interview.
Podcasting, in essence, is networking. First, at scale, by putting yourself out there for hundreds, thousands, or maybe millions to hear, and then by building a personal network with influential people in the podcasting space.
So start now. No matter if you just started, are in the middle of building a business, or have just sold your seventh successful SaaS, consider reaching out to podcasters and have a chat on their shows. At worst, you have a nice conversation with someone. At best, you put yourself, your work, and your mission out there, and among the many who listen, there is that one special person or business who will open a door that you never thought you’d ever be able to walk through.
Here are a few tips on how to prepare as a podcast guest.
- Listen to at least three or four episodes of the show, starting with the most recent one. You’ll learn a lot about the host, the audience, and how conversations work on that particular show.
- Make a little cheat sheet with things you want to cover in your conversation. When I prepared for appearing on the Indie Hackers podcast, I had a full page of notes with things I considered interesting. As someone who has trouble recalling names, I wrote down the people who influenced me most, so I could mention them correctly if needed.
- On your cheat sheet, write down your first line. Most podcast hosts open the show the same way, which you’ll have learned by listening to a few. You can pre-write a few initial responses like “Thanks for having me” or “Great to be on the show.” Trust me, when you’re nervous, getting this first line right is a massive boost to your on-air confidence.
- Consider writing down your “where to find me” line too. Most hosts will ask where listeners can find out more about the guest, so be ready to drop your best links and social media accounts there.
- If you’re bad with names, write down the full name of the host. I sometimes forget who I am talking to when I’m in the middle of a 20-minute tangent, so it’s really helpful to have their names on my little cheat sheet.
- If you’ve listened to a few shows, you will eventually understand the host’s interview style. Some people ask leading questions; some explore concepts deeply by asking follow-up questions. Some hosts are very strict with their script, and then some don’t mind going off-topic at all. Knowing how your host expects the conversation to go will allow you to phrase your responses fittingly. The goal of a good podcast is to have an enlightening and relaxed conversation. You can prepare for that by making it easy to talk to you.
- On many shows, the host might ask you a few specific questions that they ask every guest. You can prepare for that way ahead of time. Put those responses on your cheatsheet too.
- Understand who is listening. Check out the show’s reviews and what people in your audience community are saying about the podcast. A good trick here is to ask who is their favorite guest on that particular show and listening to the most commonly mentioned episodes. That’s what people gravitate to. If you can provide something similar yet different, you might be the person they mention next time someone asks for their favorite show.
- Adjust to the theme of the show. I’ve been on business podcasts that focus on idea validation. There, I talk about my experiences with the preparation stages of my businesses. I was on a show called Writer on the Side, where I spoke about my book and the publishing process, and how it fits into my greater strategy. I was on technical podcasts, where I talked about how I built a SaaS using specific technologies. You don’t have to tell the same stories every time. And even if you do, a new anecdote can teach those who heard your story before a new and meaningful lesson.
- Promote the show. Once the episode is out, make sure to share the link with your audience. Share it over the next few days, once or twice a day. Give people a chance to get to know you through that show — and give the host the chance to get to know your audience.
Finally, let me share my experience with running a podcast myself. It has been an interesting journey, for sure. At some point, I had sponsors for the show, and that was very insightful. Even with just a few hundred listeners, my podcast was interesting enough for them to spend a few hundred dollars. I read the ads during the show and got paid. I eventually stopped accepting sponsors because I wanted to focus on sharing my story. Still, it was fairly easy to find people willing to sponsor the show.
My podcast is not an interview show. If I were to categorize it, I’d say it’s a stream-of-consciousness reflection of past, present, and future endeavors in my entrepreneurial life. That makes preparing for the show fairly easy: I might take a couple of notes or write a few phrases, but most of the time, I just start recording and talk about what I want.
Shows like this are not the most popular ones. People gravitate to conversations, not lectures. If you want to build an audience around yourself, I’d recommend interviewing people on your show. That way, fresh content is available for every conversation, and you can leverage your guests’ reputation to drive traffic to your show.
Now, since I have interacted with a lot of podcast hosts that interviewed me, let me point out a few tips for how you can prepare as a host.
- Do your homework. Research your guests. Check out their websites and social media profiles. There is nothing worse for a podcast guest than talking to a host who doesn’t know the basics about your story. Luckily, this rarely happened to me. But I have been on a few shows where I needed to explain certain things that a host could have found out by reading a couple of paragraphs on my homepage. Particularly in the pre-show conversations, it’s quite the let-down if the host is completely clueless. It’s a sign of respect to do preliminary research. Skipping that leaves a bitter taste.
- Skip the surprises. If you have a lightning-round where you ask every guest the same quick-answer questions, communicate this ahead. Not every guest will have the time to pick up on your show’s specifics all the time.
- Your script is a guideline, not a manual. If you have questions prepared, consider going off-script if the conversation takes an interesting turn. People tune in for a good chat, not for a well-followed script. Find podcast hosts who have engaging interview styles and imitate them. Learn how to gently guide tangential conversations back to what you want to talk about without completely changing the subject. Interviewing is a skill, and as such, it can be improved upon.
- Send out information on how the technical part of the recording will happen. If you use Skype, hand over your Skype name so that people can connect. If you use Zoom or web-based recording portals like ZenCastr or SquadCast, make the link available ahead of time. Tell people what kind of technical equipment you recommend. Please give them a few tips on how they can make their recording environment suitable for the conversation. Many guests will not have appeared on podcasts before, and things like microphone quality and environmental noise may not be at the forefront of their minds.
- Send out invites. Don’t expect people to keep the recording you schedule five weeks in advance on their minds. Make it easy to put it into calendars by sending calendar invites, best through the recording tool your use.
- Remind people a day before the recording. If your guests have forgotten the event, they’ll be aware of it now. If people need to reschedule, you’ll have their full attention.
It’s incredibly rewarding to be in the podcast game. Both being a guest and a host are delightful activities, and they will make you stand out in your community.
Interesting Things in the Bootstrapping World
Taking over a business is hard. This week, the folks at Baremetrics learned how intense the backlash of a tribal community could be when you change things in unexpected ways. Baremetrics introduced a “call us to cancel” policy because the new management of the recently acquired metrics business learned that for some customers, self-serve offboarding could, in some cases, lead to their Stripe account stopping to charge their customers. Now that sounds like a critical issue.
Jonathan Siegel of Baremetrics explained the reasons why on Hacker News, and a number of Twitter conversations from engineers at the company shed light on this new policy. It appears that if customers don’t fully remove all of their webhook configurations from Stripe right after canceling their Baremetrics account, Stripe won’t fully charge invoices anymore (because they only charge invoices when all webhooks are confirmed).
I understand that this warrants making sure that you notify your customer before they cancel. Causing the loss of revenue due to some arcane and hidden configuration complexity is a pretty bad way to end a business relationship. In a way, I totally get why you would create a blanked policy to prevent this from happening for anyone.
But you have to understand who your audience is. You’re dealing with often very technical founders who expect you to do more. They expect you to build at least a semi-automated solution that checks if you had incoming webhooks in the past. Or something that would automatically confirm stray webhooks even when customers have canceled, as well as sending notifications to those ex-customers.
No matter what solution ultimately makes the cut, asking all of your customers to call a person will cause reputational damage in this community. It’s a too-often-maliciously-used retention tactic, and without an explanation, it feels like an attempt to make cancellation hard — all for the wrong reasons.
This is the first clash of a post-Josh-Pigford Baremetrics with their audience. If a business gets acquired, some innate understanding of “how we do things here” isn’t communicated, and the acquirer will find out the hard way. If your playbook contains a provision to install the “call to cancel” policy in all the SaaS businesses you acquire, you need to make sure that you read the room. This move might work well in high-touch Enterprise B2B SaaS, where people are used to chatting with their vendors. But not in the Indie Hackers community, a globally distributed group of solopreneurs and small teams that don’t have time for offboarding calls.
Understand your audience. Or else people will flip the script on you in hilarious ways.
JetBrains is a bootstrapped business that’s valued at $7 billion. They build software tools (like WebStorm and IntelliJ) that allow many founders to build their products. They also designed the Android programming language Kotlin, which Google has recently made the main focus of Android development efforts. As bootstrappers through and through, founder Shafirov is quoted to say, “we don’t have revenue growth targets.” Gotta love the freedom of doing whatever you want without huge investor expectations.
Jon Yongfook, Bannerbear founder and very active Twitter user, shared his top 3 lessons of the year and how he reached $8k MRR. They are solution-focus, ambitious pricing, and world-class documentation, three strategies that I can get behind. The Bannerbear journey is very insightful, with interesting data-driven pivots along the way.
The folks over at Plausible Analytics shared their lessons from building and growing an open source SaaS. With a big focus on building a stable business model, amazing customer support, and managing developer expectations, they built a business that is slowly but surely reaching the $10k MRR mark.
Thank you for reading this week’s edition of The Bootstrapped Founder. If you like what I wrote about, please forward the newsletter to anyone you think would enjoy it too.
You can find my book Zero to Sold at zerotosoldbook.com. It is being sold on Amazon and Gumroad.
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See you next week!
Warm Regards from Berlin,