Our Approach

Operator DNA with a playbook for growth.

How We Are Different

Dragonfly invests in, develops and expands portfolios of scalable companies that currently may have strategic or operational needs but have the potential to lead their industries or be a key component of a larger competitor through acquisition.


Creator and


Investment Focus

Sample Target Subsectors

  • Niche and Next-Generation Content and the Technologies That Power It
  • Entertainment / Sports Technology
  • Mixed / Augmented Reality
  • Existing and New Distribution: Mobile, OTT, Online, Broadcast, Cable, Satellite, Publishing, etc.
  • Intellectual Property & Copyrights

Investment Criteria

  • Exceptional management teams, high integrity & commitment
  • Geographic, product or service expansion potential
  • $0-25 million in revenue
  • Path to profitability or EBITDA preferred, minimal debt
  • Influential minority ownership; control investment considered in special situations
  • Headquarters in U.S. or Canada
  • Strong gross margins
  • Ability to partner on larger compelling opportunities
  • Trend lines need to show extractable value (M/M & Y/Y, Growth RPU, etc.)
  • Strong LTV and CAC positioning


Dragonfly Group LLC is a diversified, privately-held advisory and investment firm based in Chicago that is focused on platforms of content, distribution and technology. We build, advise and invest in businesses & management teams that are reimagining how content, media and entertainment engage with their audiences.