Across the United States, traditional small businesses—landscaping firms, plumbing companies, family-owned retailers—form the economic backbone of countless communities. Often passed down through generations, these enterprises are rich in local trust but constrained in scale, structure, and growth potential. In South Florida, one investor is changing that narrative.
Diego Acevedo, a veteran private equity professional with a track record of transforming mid-sized companies across Latin America, is now applying his expertise to the U.S. market. As Partner at Southern Cross Group, Acevedo is pioneering roll-up strategies that consolidate fragmented businesses into unified, scalable platforms—blending financial discipline with a deep respect for the human stories behind each company.
“Small businesses are the backbone of the U.S. economy, but many lack the scale to compete long-term,” Acevedo says. “Roll-ups allow us to combine these firms, leverage economies of scale, and build something sustainable that can thrive in a dynamic market.”
His approach, honed through transformative deals in Latin America, is now reshaping traditional sectors in Miami, where he leverages his Colombian heritage and 20 years of experience to unlock hidden potential.
Acevedo’s journey began in Bogotá, where he earned an Industrial Engineering degree from Universidad de los Andes before completing his MBA at Stanford. After early consulting roles at Booz Allen Hamilton and Booz & Co., he moved into private equity, leading investments across Latin America. At Southern Cross Group, he managed over $1 billion in assets, spearheading deals like the $100M Supermercados Xtra expansion and the $200M Esmax restructuring. These experiences shaped his ability to scale businesses amid complexity—a skill he now brings to the U.S. market.
“The U.S. is a different beast—larger, more liquid, and incredibly dynamic,” Acevedo notes. “But private equity principles remain the same: find undervalued assets, align stakeholders, and execute with discipline.”
In Miami, Acevedo focuses on traditional service businesses—landscaping, imaging centers, CPA and Tax boutiques—often owned by Hispanic or Latin families who built them over generations. As many of these owners near retirement and their children pursue different careers, succession becomes challenging. Seeing risk and opportunity, Acevedo steps in with a roll-up strategy: acquiring and consolidating these businesses into a unified, professionally managed platform. The result is stronger margins, greater scale, and long-term market resilience.
“There are a lot of businesses that are run by Hispanic or Latin families,’ He says: ‘they feel more rapport and feel more comfortable in business with someone like me that comes from Latin America, who understands their heritage. I think being in Miami now gives me a broader set of opportunities and an edge versus other people acquiring businesses.”
Ricardo Rodriguez, Founder and President of Southern Cross Group, has worked with Diego Acevedo since 2010, promoting him to Partner and observing his leadership across Latin America.
“Diego’s vision and leadership have enabled companies to scale, enhance operational efficiencies, and withstand economic volatility, solidifying his reputation as a leading expert in investment management and corporate growth.”
One of Acevedo’s current projects involves consolidating landscaping businesses in South Florida.
“Landscaping is fragmented, with many small players competing on price,” he explains. “By acquiring 10 or 15 firms, we centralize operations, improve procurement, and professionalize management, creating a regional leader with sustainable revenue.”
This approach mirrors his Latin American successes, where he scaled Supermercados Xtra from 10 to 40 stores. In the U.S., he combines his capital with the energy of young entrepreneurs, typically in their 30s, whom he mentors to execute the roll-up vision.
“Working with young managers is invigorating,” Acevedo says. “They bring the hustle, energy, and deep local knowledge of their industries. I provide the gray hair, 20 years of scars, and lessons learned from navigating complex deals and volatile markets in Latin America. It’s a powerful combination.”
His hands-on mentorship involves weekly calls and board-level guidance on acquisitions, recruitment, and strategy. This high-touch approach sets him apart from larger funds, often treating roll-ups as one of many investments.
“I’m not spread across 20 deals,” he asserts. “My focus is on a few businesses, ensuring we get every detail right— from picking the right targets to convincing owners to sell to us.”
Acevedo’s role goes beyond evaluation—he is a trusted advisor to founders navigating the challenges of scaling their companies. From mentoring the crowdfunding platform MESFIX to advising digital treasury startup COBREL and retail e-commerce platform INSTALEAP, he has provided guidance on funding strategies, governance, and long-term planning. His contributions to Endeavor reflect his broader commitment to entrepreneurship and ecosystem-building, using his experience to evaluate opportunities and shape the next generation of transformative business leaders.
Cultural fluency is a cornerstone of Acevedo’s strategy. In Miami, where many business owners are of Cuban, Colombian, or other Latin descent, his ability to connect in Spanish and understand their values gives him an edge.
“These owners want a caretaker for their life’s work, not just a check,” he says. “They trust me because I understand their heritage and how business is done in Latin America—more personal, less transactional.”
Acevedo’s governance expertise ensures these roll-ups succeed post-acquisition. Drawing on his experience with Supermercados Xtra, where he resolved family governance issues and implemented a professional management structure, he creates frameworks that balance growth with stability.
“Governance is the glue that holds a roll-up together,” he explains. “You need clear incentives for managers, transparent reporting, and a board that keeps everyone aligned.”
His landscaping roll-up, for instance, operates with a centralized management team that oversees day-to-day operations across all acquired firms. By integrating functions like finance, HR, and procurement, the platform reduces redundancies and improves decision-making. Standardized performance metrics—tracking everything from customer retention to route efficiency, ensure accountability and drive profitability across the board.
The results speak for themselves. Acevedo’s roll-ups create businesses with higher margins and stronger market positions that are attractive to future buyers like private equity firms or strategic investors.
“A well-executed roll-up can transform a $2 million business into part of a $50 million platform,” he says. “That’s life-changing for the original owners, who often see the biggest liquidity events of their lives, and it creates real career paths, job stability, and benefits for employees who might have previously worked in less structured environments.”
His focus on traditional sectors also boosts local economies, particularly in Hispanic communities where these businesses are rooted.
Acevedo’s playbook has three pillars: disciplined acquisition, operational integration, and stakeholder trust.
“Buying well is half the sale,” he quips, echoing a principle honed over years of deal-making in Latin America. “If you acquire the right business at the right price, you’ve already solved a big part of the equation. It sets the foundation for everything that follows, operational improvements, strategic growth, and ultimately a successful exit.”
Mauricio Osorio Sánchez, President of Crezcamos S.A., began working with Diego Acevedo in 2017 when Southern Cross Group invested in the microfinance company.
“Mr. Acevedo’s leadership was critical in expanding our financial offerings, successfully guiding the company through a complex regulatory transition… His deep financial expertise and strategic oversight were critical in securing regulatory approvals.”
He rigorously evaluates targets, discarding those with red flags and focusing on firms with defensible niches. Integration involves streamlining operations—standardizing equipment, negotiating bulk contracts, or implementing technology—while preserving the local expertise of acquired firms. Trust, built through cultural alignment and transparent communication, ensures owners and managers stay committed.
His emerging markets experience gives him a unique edge in the U.S. “Latin America taught me to expect the unexpected,” Acevedo reflects. “Currency crashes, political crises—you learn to stay calm and find opportunities in chaos. That resilience helps me navigate the U.S. market’s complexities.”
His ability to manage risks, like economic downturns or labor shortages, ensures his roll-ups remain robust.
Mentorship is another hallmark of Acevedo’s approach. Having guided over 20 investment professionals at Southern Cross, he now mentors young entrepreneurs in Miami, helping them scale their ambitions.
“I tell them to under-promise and over-deliver,” he says. “It’s one of the core values I emphasize with every team I work with. When you manage expectations realistically and then exceed them, you build lasting trust—with investors, employees, and clients.
His mentees—many of whom now lead the day-to-day operations of his roll-up ventures—credit Acevedo not only for his strategic insights, but also for his accessibility and willingness to guide them through complex challenges. Whether it’s navigating an acquisition, restructuring a team, or refining a growth strategy, he remains a hands-on partner.
Alberto Calvo, Chief Executive Officer of Supermercados Xtra, worked closely with Diego Acevedo from 2017 to 2021 during Diego’s tenure at Southern Cross Group, when they led the transformation of the company.
“Under his direction, Supermercados Xtra underwent a massive transformation that yielded extraordinary results… revenue soared from $5000 million to $800 million, while EBITDA nearly doubled from $32 million to $60 million… His financial expertise, strategy, and ability to drive complex transformations set him apart as one of the leading investment professionals in the region.”
As he continues to expand his footprint across the U.S., Acevedo’s vision for roll-ups remains clear: to build sustainable, scalable businesses that honor the legacy of their founders while implementing the systems, governance, and efficiencies needed to thrive in today’s competitive market.
“Traditional businesses don’t need to stay small,” he insists. “With the right strategy, structure, and support, these companies—many of which have been built with grit and determination—can scale up, compete with the big players, and leave a lasting legacy.”
Acevedo’s focus on traditional businesses is refreshingly grounded in a market obsessed with tech unicorns. His roll-up strategy, blending private equity discipline with cultural savvy, is a masterclass in value creation.
“The art of the roll-up is about seeing potential where others don’t,” he concludes. “It’s identifying overlooked businesses with strong fundamentals and bringing them together in a way that creates real synergy. It’s not just about buying companies—integrating them thoughtfully, improving operations, and unlocking value that wasn’t visible before.”
