Usually means: Taking risks with bold confidence.
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We found 11 dictionaries that define the word venturesomely:

General (10 matching dictionaries)
  1. venturesomely: Merriam-Webster
  2. venturesomely: Oxford Learner's Dictionaries
  3. venturesomely: Collins English Dictionary
  4. venturesomely: Vocabulary.com
  5. venturesomely: Wordnik
  6. venturesomely: Wiktionary
  7. venturesomely: Dictionary.com
  8. venturesomely: Webster's 1828 Dictionary
  9. venturesomely: FreeDictionary.org
  10. venturesomely: TheFreeDictionary.com

Business (1 matching dictionary)
  1. venturesomely: Legal dictionary

(Note: See venturesome as well.)

Definitions from Wiktionary (venturesomely)

adverb:  In a manner that is bold and willing to take risks; adventurously.

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