import Foundation
let pattern = #"(?<=[a-z\d])([A-Z$][A-Za-z]*(?: +\S+?)*):"#
let regex = try! NSRegularExpression(pattern: pattern, options: .anchorsMatchLines)
let testString = #"""
[['Company OverviewCompany: HowSector: SoftwareYear Founded: 2010One Sentence Pitch: Easily give and request low-quality feedback with your team to achieve more togetherUniversity Affiliation(s): Duke$ 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']]]
"""#
let stringRange = NSRange(location: 0, length: testString.utf16.count)
let substitutionString = #", \1:"#
let result = regex.stringByReplacingMatches(in: testString, range: stringRange, withTemplate: substitutionString)
print(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 Swift 5.2, please visit: https://developer.apple.com/documentation/foundation/nsregularexpression