Private Equity & Family Businesses

As Succession Planning Falters, Chicago Becomes a Case Study in Crisis

Discover how Enventure, led by Ankit Shrivastava, is helping family-owned businesses in cities like Chicago navigate succession planning through innovation, strategy, and AI-driven tools.

Featured Image

Enventure and Ankit Shrivastava Are Tackling America’s Family Business Succession Crisis

Originally published by: Article.Rich 

 

America is facing a quiet but massive succession planning crisis—and family-owned businesses are at the center of it. According to private equity firm Enventure, 57–67% of U.S. family businesses are unsure how they’ll transition leadership. With baby boomers retiring quickly, this uncertainty threatens entire communities and local economies.

Chicago: The Epicenter of a Growing Concern

In cities like Chicago, where nearly 80% of businesses are family-owned, the problem is especially urgent. These companies form the fabric of neighborhoods—from food manufacturing to logistics—and now face a reckoning: who will lead the next generation?

Without solid plans in place, businesses risk decline, employee attrition, and a loss of legacy built over decades.

The Enventure Approach: Strategy Meets Heritage

Ankit Shrivastava, Founder and Managing Partner at Enventure, sees this as more than a leadership issue. “Succession planning must incorporate strategy, digital readiness, and innovation,” he says.

Enventure’s model blends strategic capital with operational guidance. Instead of replacing founders outright, their co-ownership approach allows seasoned leaders to stay involved while preparing the next generation to scale.

The Role of AI in Modern Succession Planning

One of Enventure’s most powerful tools is AI. “Artificial intelligence can streamline operations, reveal new market opportunities, and support smarter decision-making,” explains Shrivastava.

From supply chain optimization to forecasting and successor evaluation, AI helps systematize institutional knowledge—reducing over-reliance on founders and making transitions smoother.

Chicago’s Legacy Firms at a Crossroads

The Midwest—especially Chicago—offers both cautionary tales and success stories. From Ferrara Candy Company’s acquisition to logistics firms reinventing themselves digitally, the spectrum is wide. Still, many small and mid-sized family businesses remain under the radar, quietly struggling with succession.

The questions remain pressing: Who will lead? How do we grow? Can we preserve what made us unique?

Tradition and Transformation Can Coexist

Shrivastava emphasizes: “Succession isn’t an endpoint—it’s a pivot.” By merging legacy with innovation and leveraging technology, family businesses can evolve rather than dissolve.

Enventure is proving that the right blend of strategic guidance, tech adoption, and respectful transition planning can turn a looming crisis into a unique opportunity—especially in legacy-rich cities like Chicago.

But action is urgent. The window for successful succession is closing, and the choices made today will define the next decade of American entrepreneurship.