Investing in Coffee, Private Capital, and Emerging Markets with Cole Shephard

In this episode of the DealQuest Podcast, I’m excited to welcome Cole Shephard, founder and executive chairman of Green Coffee Company and a partner at Legacy Group. With nearly a decade at PwC, Cole built a strong foundation in accounting, M&A advisory, and consulting across multiple continents—including the U.S., Bermuda, Hong Kong, and Beijing. A decade ago, he took a bold leap, moving to Colombia to pursue real estate and agriculture opportunities, eventually launching GCC.

Cole is an expert in private capital markets, emerging market economies, and the coffee industry. In this episode, he shares his journey from corporate finance to entrepreneurship, the unique opportunities in Colombian agriculture, and what investors need to know about high-growth markets. Whether you're an entrepreneur, investor, or coffee enthusiast, this conversation is packed with insights you won’t want to miss!

ADAPT TO DIFFERENT CULTURES TO SUCCEED IN BUSINESS

Cole Shepherd highlights the importance of adapting to cultural differences in international business. Cole’s experiences in Bermuda and Hong Kong taught him how cultural nuances can make or break a deal.

In Bermuda, he encountered variations in dialect and vocabulary despite a shared language, much like the differences between Mexican and Argentine Spanish. In Hong Kong, cultural etiquette became even more crucial—such as tapping the table after a tea refill as a sign of respect.

Successful business relationships require more than language skills; they demand cultural awareness. Even small missteps—like not knowing Japanese clients expect special pens for signing deals—can harm relationships. Adapting to cultural norms is essential for success abroad.

THE VALUE OF GLOBAL EXPERIENCE AND FLEXIBILITY

At 25, Cole Shephard took a leap, moving to Bermuda instead of following a traditional career path in New York or Chicago. The island’s financial services industry exposed him to a global talent pool, expanding his experience beyond the U.S.

By 28, he took an even bigger step, relocating to Hong Kong. Unlike Bermuda, where he worked with fellow expats, he was now immersed in a workplace with local professionals from Hong Kong, Mainland China, and across Asia. Adapting to new markets without prior experience in Asia was key to his success.

Cole’s journey proves that stepping outside your comfort zone and embracing global opportunities can fast-track career growth. Flexibility and a willingness to learn in unfamiliar environments open doors to unexpected opportunities, giving you a competitive edge in an increasingly connected world.

ADAPT TO BUSINESS PACE AND RELATIONSHIPS ACROSS MARKETS

In fast-paced cities like Hong Kong and New York, business is highly transactional—deals move quickly, and the focus is on results rather than relationship-building. However, in mainland China and Latin America, trust and long-term connections take precedence. In China, deals are often finalized before advisors are even consulted, while in Latin America, taking the time to build rapport is essential. Rushing the process can harm potential partnerships.

Understanding whether a market values speed or relationships is crucial for international business success. Adapting to these differences can help you build trust, avoid missteps, and close deals more effectively.

TURN MARKET INEFFICIENCIES INTO OPPORTUNITIES

Cole Shephard discovered that emerging markets often have inefficiencies that can be turned into profitable opportunities. In Colombia, he noticed that real estate prices were based on arbitrary “strata” ratings, which determined property values based on how desirable an area was perceived rather than actual market demand. Without a centralized listing system (MLS), buyers and sellers had limited access to comparative pricing data, creating inconsistencies in property valuations. Instead of seeing this as a challenge, Cole recognized an opportunity to invest strategically by leveraging these pricing gaps.

This ability to identify inefficiencies and turn them into advantages is key for success in emerging markets. Whether in real estate, finance, or other industries, markets that appear chaotic or underdeveloped often present room for innovation. By understanding these gaps and finding ways to navigate them, businesses can gain a significant edge and capitalize on opportunities before the market matures.

VALIDATE YOUR BUSINESS IDEA BEFORE SCALING

Early in his career, Cole didn’t have millions in funding or big backers. Instead, he took a more cautious approach, using personal savings, including money from his pension fund, to fund initial ventures. For example, when he entered the financial services and real estate markets, he kept his deals small and manageable, testing the waters to see if his business ideas could succeed in the real world. The key was not rushing into big, high-risk deals but proving the viability of his concept on a smaller scale first.

By starting small, Cole was able to build credibility and confidence in his ability to execute his ideas successfully. Once he demonstrated that his approach worked, he attracted the backing necessary to expand and take on larger, more lucrative deals. His experience teaches entrepreneurs that before seeking major investments or scaling their operations, it’s crucial to validate the business idea in a real-world context, ensuring it’s viable and can be executed effectively without relying too heavily on outside funds. This approach minimizes risk and increases the likelihood of long-term success.

LEVERAGE UNIQUE TRADE CORRIDORS FOR COMPETITIVE ADVANTAGE

While many entrepreneurs focus on mainstream markets, Cole saw potential in connecting businesses from regions others didn’t consider. For instance, he began building trade relationships between U.S. companies, Colombian businesses, and international markets like South Korea and Japan, focusing on commodities like coffee and fresh-cut flowers.

This trade corridor was largely untapped at the time. By identifying and exploiting these underutilized routes, Cole gained access to valuable opportunities others overlooked. This approach gave him a competitive edge and helped diversify his operations. His story demonstrates that thinking outside traditional markets and exploring unconventional connections can create unique growth and innovation opportunities.

BUILD LOCAL PARTNERSHIPS WHEN EXPANDING INTO NEW MARKETS

Cole Shephard’s journey underscores the critical role of local partnerships when entering unfamiliar markets. Early in his career, he moved into the Colombian real estate market with no prior experience. He quickly realized that navigating its complex, bureaucratic processes—like bankruptcy sales tied to local legal systems—was challenging without local expertise.

To overcome these hurdles, Cole built a team of local experts who understood the market's nuances. This local knowledge allowed him to navigate the system effectively, spot opportunities, and adjust his strategies for better decision-making.

Cole’s experience shows that strong local partnerships are key when expanding into new markets. They provide insights into cultural, legal, and logistical factors that can make or break a business. Without these relationships, businesses risk struggling or even failing. So, invest in local partnerships to set the foundation for long-term success.

MOVE BEYOND AN ASSET PLAY TO BUILD A FULL ENTERPRISE

In the coffee industry, Cole initially focused on maximizing returns by buying estates and improving agricultural processes. However, he soon realized that long-term success required more than asset transactions.

He pivoted to building a sustainable business by investing in infrastructure, people, and processes, aiming to lead both nationally and globally. This transformation, including vertical integration, helped his company grow and stand out. The key takeaway: true business growth comes from creating value beyond short-term profits, focusing on long-term goals and building a well-rounded enterprise.

GET ACTIVELY INVOLVED IN BUSINESS OPERATIONS

Cole Shephard learned the importance of being hands-on in business operations. When he first started his coffee business in Colombia, he focused on attracting investors and structuring deals, leaving day-to-day operations to his team. But as the business grew, he realized he needed to take a more active role.

Cole transitioned from a passive investor to an active partner, holding weekly meetings and guiding decisions on marketing, acquisitions, and vertical integration. For example, he became involved in daily green coffee strategies, something he hadn’t anticipated initially.

This shift enabled him to make faster, more effective decisions and gain a deeper understanding of the business. For entrepreneurs and investors, active involvement is crucial to shaping long-term success.

OVERCOMING MISPERCEPTIONS AND BUILDING INVESTOR TRUST

When Cole launched his coffee business in Colombia, he faced skepticism from U.S.-based investors due to concerns about the region's safety and reputation. In 2017, many investors questioned whether they could trust Cole with their money, given Colombia's past with drug cartels and political instability.

Cole's challenge was to build trust by addressing these concerns head-on. Instead of just selling the business opportunity, he worked to establish credibility through transparency, sound business strategies, and consistent growth. Over time, as both Cole's business and Colombia’s reputation improved, investor questions shifted from concerns about trust to inquiries about ROI, IPO potential, and business scaling.

This shift highlights the importance of proving your reliability through effective, transparent business practices. Entrepreneurs entering new or misunderstood markets must actively address investor concerns to build trust and credibility.

EMBRACE A BROADER VIEW OF BUSINESS OPPORTUNITIES BEYOND TRADITIONAL M&A

Cole Shephard highlights options like joint ventures, strategic partnerships, licensing agreements, and affiliate deals. For example, Cole’s company entered into a licensing deal with the Juan Valdez brand to expand into the U.S. and Canada— a move that didn’t involve the complexities of M&A but still offered significant growth potential.

The key takeaway is to remain flexible and evaluate all opportunities that align with your business goals. Whether it’s licensing, joint ventures, or strategic alliances, considering diverse options can help you expand without relying solely on M&A.

VALUE PATIENCE AND CULTURAL SENSITIVITY IN NEW MARKETS

Many investors shy away from markets like Colombia due to negative stereotypes surrounding its past, but Cole saw potential where others saw obstacles.

He understood that to succeed in Colombia, he needed to build strong local relationships and navigate bureaucratic hurdles. The local market had been suppressed for years, with many businesses being family-run and lacking innovation. This created a unique opportunity for foreign investors who were willing to take the time to build trust and introduce fresh ideas.

The key takeaway is that when entering markets with cultural or historical complexities, it’s essential to be patient, culturally aware, and open to new ways of doing business. This approach can uncover valuable opportunities that others may overlook.

EXPLORE CREATIVE SOLUTIONS TO BUSINESS PROBLEMS

Many entrepreneurs assume that traditional methods, like mergers or acquisitions, are the only way to solve business challenges. Business owners should think beyond these conventional approaches and explore creative solutions. For example, when facing challenges like talent recruitment, rather than relying solely on traditional hiring processes, consider alternatives like an acqui-hire—acquiring an entire company for its team, not its financials. This can be a more efficient way to quickly bring in skilled employees without going through the lengthy recruiting process.

SEEK INVESTMENT OPPORTUNITIES BEYOND DEVELOPED MARKETS

Cole Shephard emphasizes the value of exploring investment opportunities in emerging markets like Colombia, which are often overlooked by investors focused on developed countries. While these markets can be challenging, they offer unique and profitable opportunities, particularly in private equity and venture capital.

In developed countries like the U.S., investors often target early-stage companies that haven’t turned a profit yet. In contrast, emerging markets like Colombia offer more mature companies, sometimes at Series C or D, with less risk. By investing in these markets, you can access businesses that are further along and more stable for a fraction of the cost.

Emerging markets present untapped potential with lower competition, offering higher returns at a lower price. The smart investors of today recognize the value of looking beyond traditional markets to discover high-growth, undervalued opportunities that provide greater returns with lower risks.

Tune in to this episode to hear Cole Shephard share his insights on navigating private capital, investing in emerging markets, and seizing opportunities in the coffee industry.

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FOR MORE ON COLE SHEPHARD
Cole Shephard’s LinkedIn
Juan Valdez Coffee


FOR MORE ON COREY KUPFER
Corey Kupfer's LinkedIn
Corey Kupfer's Website

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!