Heartland Ventures: This $75 Million Venture Firm Connects Startups With New Customers In The Midwest

By Amit Chowdhry ● Aug 7, 2023

Heartland Ventures is a venture capital firm that connects high-growth startups with new customers in the Midwest. Pulse 2.0 interviewed Heartland Ventures Managing Director Max Brickman to learn more.

Max Brickman

Max Brickman is the Managing Director of Heartland Ventures, which he founded in 2016.

Max has always been entrepreneurial. At age 14, he purchased his first investment property, a rundown duplex in northern Wisconsin, using money from a small landscaping company he had started. Over the years, he grew the single property into a 450-residential unit portfolio. Later, while studying Finance and Entrepreneurship at Indiana University, he invented and patented an academic software product.

Today, he is a venture capitalist with a passion for expanding technological innovation into smaller, underrepresented heartland communities. He closely follows and analyzes Midwestern business trends to gain insights into pain points, tech needs, and operational opportunities. He manages the fund’s relationships with other venture capital partners and oversees key investment decisions with the Heartland team.

He was recently named to the Forbes 30 Under 30 list, an Executive of the Year by Columbus Business First, and a Future 50 Member by Columbus CEO, to which he credits the hard work of the Heartland team and all its portfolio companies.

Evolution Of Heartland Ventures’ Thesis

How has Heartland Ventures’ thesis evolved over time? Brickman shared:

“The reality is, our thesis has remained remarkably consistent since the day we were founded. Heartland exists to bridge the gap between America’s heartland corporations and the country’s hubs of technology innovation. By connecting private, often rural, and mostly multi-generational business owners and operators (our Limited Partners) with tech startups, we are giving business leaders a voice in the tech transformation happening in their industries.”

“We have seen a great need for this venture model, and Heartland has effectively formed the largest network of mid-market tech buyers in the Midwest.”

Significant Milestones

What have been some of Heartland Ventures’ biggest milestones? Brickman cited:

“Raising and fully investing out of our Fund I was an important milestone for proof of concept. We validated Heartland’s thesis by first assembling a robust network of mid-market businesses with an appetite for investing in R&D and innovation. Then, we identified and funded ten startups solving real-world business challenges for our LPs and introduced those groups.”

“Last year, we successfully closed our second fund, which, at $52 million, is 3X the size of our debut fund.”

“To date, we have invested in 16 high-performing portfolio companies.”

Investment Success Stories

Upon asking Brickman about some investment success stories, he highlighted:

“Workstream, a mobile-first hiring and onboarding platform for the deskless workforce, is among the success stories from our debut fund. Last year, the San Francisco-based company completed a $108 million Series B funding round, at a $460 million valuation.”

“Desmond Lim, Workstream’s co-founder and CEO, credits Heartland’s Midwest partnerships with validating the scale of the opportunity—both the service industry and blue-collar jobs, all across America—and massively expanding its total addressable market.”

“In another example, we introduced Crawford Hoying, a Limited Partner that develops and manages real estate, to Parkade, a Fund II portfolio company that optimizes parking experiences for landlords and their tenants. The app-based parking solution has allowed Crawford Hoying to more easily manage parking and created a new revenue opportunity from underused spaces. Crawford Hoying even saw an increase in parking revenue of 46% at one of their properties.

“To date, Heartland has supported two portfolio companies that were acquired.”

Assets Under Management

Upon asking Brickman about the firm’s assets under management, he revealed:

“We have around $75 million under management, including sidecar investments dedicated to specific portfolio companies.”

Industry Focus

What are some of the industries that Heartland Ventures is focused on? Brickman noted:

“We focus on the built environment and infrastructure, which encompasses manufacturing, construction, logistics, and real estate. These industries are strong in America’s heartland and each has challenges that can be solved with technology.”

Differentiation From Other Firms

What differentiates Heartland Ventures from other firms? Brickman pointed out:

“The way we connect our LPs and portfolio companies is what makes our model special. For mid-size corporations based in the Midwest (Heartland LPs), we serve as a sort of outsourced R&D, introducing these business operators to high-growth technology startups based in traditional tech hubs like Silicon Valley. On the other side of the coin, startups are being introduced to their first customers, which helps to find product-market fit and scale based on real-world demand.”

Future Goals

What are some of Heartland Ventures’ future goals? Brickman concluded:

“We are focused on the “blocking and tackling” for each of our LPs and portfolio companies, making connections and providing operational guidance and support, day in and day out. If we execute at this micro level, then we can help close America’s innovation gap between the coasts and the heartland. Our ultimate goal is to connect industry and innovation, regardless of geography.”

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