This app was mentioned in 2 comments, with an average of 1.50 upvotes
I usually use a Garmin to track my rides but I've used this too when I've just wanted to use my phone. It lets you start strava from the pebble
https://play.google.com/store/apps/details?id=com.giovannizilli.pebblestrava.app
Edit : you said iPhone! Doh.
Maybe you'll be the only person who sees this, but I found an app for controlling Strava. It can only do start/stop, but that is all I really need in a Pebble app.
Which podcast app do you use? How is the functionality with the Pebble? I feel like my phone in my bag, a smartwatch and wireless headphones are a complicated way of making things easier. If I can work out the kinks I think it should work really well.