Description

Company: Online Optimism
Owners: Flynn Zaiger
Year Started: 2012
Employees: 26-50 (Medium)

Starting a business is already a little crazy. Growing one with a strong culture and team might be even harder. In this episode, Flynn Zaiger, founder of Online Optimism, shares what he wishes he knew at 22, including how listening, trust, and transparency became his agency’s competitive edge. If you’ve ever struggled with hiring, hybrid work, or leading a growing team, this one’s for you.

Key Takeaways

• The early hiring move that saved Flynn from founder burnout
• Why building trust starts with listening (and how to do it right)
• How hybrid culture can work, if you’re willing to invest
• The danger of ignoring feedback (and the rule that changed everything)
• Why his team pushes back and why he encourages it

Details for an agency planning workshop event November 10th and 11th 2025.