Prominent Investor Zack Onisko Hints at "Opening Day" for Summer Plans

Zack Onisko, a well-known figure in the tech and investment landscape and former CEO of Dribbble, has piqued public interest with a cryptic tweet suggesting an "opening day" for summer plans this coming Tuesday. The brief social media post, shared on June 27, 2025, simply states, "In case you haven't locked down your Summer plans, Tuesday is opening day." The announcement has left many speculating about the nature of his new endeavor.

Onisko, who transitioned from an operational role to becoming a seasoned investor and Managing Director at Enduring Ventures, is known for his contrarian approach to business and his focus on acquiring high-potential, cash-flowing companies. His career highlights include leading Dribbble to significant revenue and EBITDA growth without venture capital, and successfully growing Creative Market before its acquisition. He has also expressed a personal interest in real estate investments.

Following his departure from Dribbble in 2024, Onisko indicated a desire to shift towards an owner/investor role, actively seeking businesses to acquire. His current firm, Enduring Ventures, specializes in permanent equity holdings, operating more like a family office. This strategy aligns with his philosophy of building wealth through long-term ownership rather than traditional venture capital models.

Additionally, Onisko is involved with Hampton, a highly vetted community for high-growth founders and CEOs, suggesting his "summer plans" could also relate to an initiative within this entrepreneurial network. Given his background in scaling digital platforms and his recent pivot to strategic acquisitions, the "opening day" could signify a new business acquisition, the launch of a new real estate project, or a significant development within the Hampton community.

The lack of specific details in Onisko's tweet leaves the exact nature of this "opening day" open to interpretation. However, his track record of successful ventures and his current focus on strategic investments indicate that any new announcement from him is likely to be a significant development in his expanding portfolio. Further details are anticipated as the mysterious Tuesday approaches.