I tried to transscribe one episode of my podcast which was 1,5 hours long. I'm commuting 2 * 1h per day and I was able to transstribe about 5 minutes of audio per hour, after a couple of weeks I had transcribed about 40 minutes. I used a special software to do that too which connected the text with timestamps to the audio. But I had to give up because I wasn't able to do anything else but transcribing, it was just too time consuming.
And the automatic transcribtion services are still quite bad. And paying someone to transcribe is quite a financial burden. I agree that it would be awesome but I don't quite agree that the technology is there (yet).
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I did not know you tried it yourself. Sounds indeed like an annoying thing to do. Regarding the payment it's also a very good argument that you would pay on top of your time. For me it's just sad that I really would like to get the content of your Podcasts, without spending 1,5 hours listening to it. Let's hope the technology will soon meet your demands. 😀