$re = '/(?<=[a-z\d])([A-Z$][A-Za-z]*(?: +\S+?)*):/m';
$str = '[[\'Company OverviewCompany: HowSector: SoftwareYear Founded: 2010One Sentence Pitch: Easily give and request low-quality feedback with your team to achieve more togetherUniversity Affiliation(s): Duke$ Raised: $240,000Investors: Friends & familyTraction to Date: 10% of monthly active users (MAU) are also active weekly\'], [[\'Company OverviewCompany: GrubSector: SoftwareYear Founded: 2018One Sentence Pitch: Find food you likeUniversity Affiliation(s): Stanford$ Raised: $340,000Investors: Friends & familyTraction to Date: 40% of monthly active users (MAU) are also active weekly\']]]
';
$subst = ", \1:";
$result = preg_replace($re, $subst, $str);
echo "The result of the substitution is ".$result;
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for PHP, please visit: http://php.net/manual/en/ref.pcre.php