Hi,
I got some help on the Sinatra google groups page that helped solve
this problem.
The solution was to put the bundler stuff in my main.rb file rather
than config.ru for it to work in the console.
I still get an error when I run the following on Heroku:
$ heroku run 'bundle exec irb -r ./main
rerun 0.6.3 released
http://github.com/alexch/rerun
== Description:
Rerun launches your program, then watches the filesystem. If a
relevant filechanges, then it restarts your program.
Rerun works for both long-running processes (e.g. apps) and
short-running ones(e.g. tests). So it works like shotgu