The eternal struggle of trying to build a podcasting empire while navigating the complexities of digital privacy and corporate espionage!

On the one hand, building an ultra-manual scheduling process might seem like a more personal, bespoke approach. But let's be real, that means you'll be spending even more time playing email tag with your guests, waiting for them to respond to your "hello, I'm thinking of having you on my podcast" emails.

On the other hand, automating the process using off-the-shelf tools can save you so much time and reduce the risk of human error (aka getting scheduled at 3 am with a guest who's already in bed). But, as you mentioned, these tools often require integration with popular calendar services like Google Workspace.

Now, about Proton Mail... I feel your pain. It's great that you're prioritizing digital security and independence, but yes, it can be a bit of a learning curve (and some might say, an existential crisis). But hey, if you're willing to put in the time and effort, you'll be rewarded with unparalleled encryption and anonymity.

As for using Google Workspace as a paying business customer... I'd caution that it's still not entirely without risks. While they claim to respect users' privacy, there are concerns about data collection and sharing (e.g., with law enforcement or advertisers). Whether or not this is something you'll regret depends on your individual values and priorities.

And then, of course, there's the signal vs. no signal conundrum. Do you care if Google is watching? Honestly, it's a bit like worrying about what others think – most people don't even realize they're being tracked all the time. But hey, Signal is an excellent choice for encrypted comms.

As for getting "cancelled"... in today's online world, reputation is basically just a digital footprint waiting to happen. So, yes, if you get cancelled, you'll likely be cancelled... hard and fast.

In conclusion, I'd say it's all about weighing your priorities: do you value the convenience of automation vs. the security of Proton Mail? Can you stomach the risk of Google collecting some of your digital DNA? And how will you deal with the inevitable drama when things go south?

For me, it's all about embracing the trade-offs and finding a balance that works for you. Maybe take a cue from the ancient Greeks: "Know thyself"... and also, use Signal

Nothing you do really matters except for the guests you have on or the content you create. I’d focus on the one thing that actually matters first and do the other stuff later

I try and apply my privacy practices to my personal life, which mostly includes helping my kids and the rest of my family avoid some of the privacy mistakes I made along the way.

There is only so much one can do though. Just in the last couple of years, my data has been breached by a medical lab, a hospital, EquiFax, a post secondary institution, the Canada Revenue Agency etc.

I use Google backend for my business because it works, and it saves a tonne of time. Gemini is also coming in hot and has surpassed other LLMs, IMO.

If privacy is a top concern, ProtonMail and alternatives like Nextcloud are worth considering, though less user-friendly. Google Workspace is efficient, but you’re trading privacy for convenience. If you’re okay with that, go ahead—but be mindful of the trade-offs.