The Curious Case of Apples, Oranges, Monkeys and Cadillacs
Photo by Jamie Haughton
When Success Becomes Your Greatest Challenge
Every iconic business began with a singular focus. Amazon sold only books. Apple had just one computer. McDonald's offered a simple menu of hamburgers, fries, and shakes. In these early days, the path forward was clear—perfect that one offering, expand your customer base, and establish your brand and market position. Success was defined by doing one thing exceptionally well.
But success breeds opportunity, and opportunity leads to expansion. Restaurants adds a breakfast menu to utilize morning capacity. Software companies develop complementary applications. Manufacturers create variations to serve adjacent markets.
As the business grows, each addition to the menu of products and/or services might seem logical in isolation. Yet somewhere between five and fifteen offerings, the clarity that drove your initial success becomes clouded by competing priorities, resource allocation debates, and increasingly complex operations.
This evolution from focused startups to more complex business operations happens so gradually that most business leaders fail to recognize the moment when at-the-time-it-made-sense decision-making is no longer adequate.
The symptoms of a complex portfolio are clear. Offerings that once contributed substantially to business growth plateau or decline. New offerings cannibalize rather than complement established ones. Marketing messages become confusing or watered-down across too many fronts.
The businesses that thrived because of their original simplicity now struggle with complexity, and what began as healthy diversification transforms into a chaotic mix of offerings that drain resources and attention from your best performers.
What Exactly is an Optimal Portfolio
When your business portfolio is firing on all cylinders, every product and service contributes meaningfully to your success. Each offering fulfills a strategic purpose—whether generating consistent cash flow, capturing market share, establishing brand position, or exploring future growth areas. Nothing coasts along or drains resources unnecessarily. Regular portfolio reviews ensure you're investing appropriately across your lineup, eliminating friction points, and making timely adjustments as market conditions change. Like a finely-tuned engine, this balanced approach delivers maximum power with minimum waste, driving your business forward with synchronized precision.
But consider this: What if the products you're pouring resources into are actually your least profitable? What if your marketing budget is being wasted on offerings with minimal growth potential while the winners receive insufficient support?
Through deliberate portfolio management, companies like Apple, Procter & Gamble, and Amazon regularly prune underperforming offerings while doubling down on their stars—a practice that compounds their competitive advantage year after year. The businesses that make portfolio optimization a regular habit don't just enhance short-term profitability; they systematically build resilience against changes in the markets they serve and position themselves to capitalize on emerging opportunities before your competitors can react.
Case Study: Fruits, Furs and Fenders
Your current mix of products and/or services may not be as chaotic as we find in this case study, but read on to determine if some fine tuning might be necessary to better posture your business for profitable growth into the future.
Asher started his business “Fruits, Furs and Fenders”with an unusual mix of products: apples, oranges, monkeys, and Cadillacs. You might wonder how his business moved in this direction but his reasons were reasonably straightforward and based on principles he’d learned as a child, “When opportunity knocks, answer the door”.
The Case for Apples and Oranges
Asher inherited a small apple orchard from his grandfather and decided to start a business selling fruit. The initial investment was low, the harvest was seasonal but predictable, and his grandfather had several friends who also owned small fruit and citrus groves. Over time, Asher added oranges thinking fruit buyers will want variety. Through his grandfathers friends, he developed access to supply and the seasonal differences provided income during the previously lean months.The Case for Monkeys
Asher’s brother-in-law worked at a zoo and suggested exotic pets as a high-margin business opportunity. Asher soon confirmed the opportunity and markup potential, but possibly underestimated the substantial complexities including government requirements for specialized licenses, caring for exotic animals, unpredictable supply/demand, and cost of insurance. Sales were infrequent and the cost of maintaining full time staff and their habitat consumed most of the profit.The Case for Cadillacs
When a dealership on a nearby town closed, Asher purchased three Cadillacs at auction based on the potential for large one-time profits. He liked driving a Cadillac, and now he owned the local dealership. It wasn’t long before he realized how much of his limited resources were tied up in inventory. The demand for luxury cars was sluggish, the cost of building an elaborate showroom was substantial and managing the dealership was a full-time job.
His business portfolio evolved over time and, looking back, the decisions to introduce each product line made sense … at the time. What he didn’t admit as readily, is that he had let his emotional attachment to these products trump business logic.
After two years his business was barely surviving, employee morale was low, his attempts to market and grow the business produced mixed results, and his business had become somewhat of an oddity in the eyes of his customers.
Establishing the Baseline
Before making any changes, Asher decided to dig a little deeper into how each product was contributing to his problems. He called a couple like-minded peers to ask if they would help him look at his business results objectively, and make changes as necessary.
Here’s what they found:
Asher’s portfolio analysis revealed untapped potential in what he had dismissed as a mundane fruit operation. Fruit sales shared similar distribution channels, customer bases, and storage facilities. They offered complementary seasonality, helping to balance revenue throughout the year and maintain consistent cash flow. And they required similar expertise and business knowledge, allowing Asher to develop deeper competencies rather than spreading his knowledge thin across unrelated fields.
His fruit business presented opportunities to expand into complementary offerings such as premium varieties, other fruits, and value-added products like juices. All of these allowed Asher to strengthen his market position while increasing profit margins—moving from simply selling commodities today to creating a distinctive specialty produce business with sustainable competitive advantages in the future.
The expense of keeping monkeys fed and entertained was substantial. They also required a separate physical space that resembled a zoo and required a dedicated, highly trained staff.
After all the expense of caring for a small troop of monkeys, however, profits from this part of his business were relatively low and supply/demand was unpredictable. The complexity of specialized licensing for non-native animals was significant and the potential liability of an exotic pet seriously injuring a potential buyer (and his business reputation) kept Asher up at night.
Selling Cadillacs presented several challenges. For starters, selling luxury vehicles required automotive sales expertise completely unrelated to his other product lines. Sales were infrequent, required an expensive showroom and specialized equipment for service. Asher’s inventory of Cadillacs tied up enormous capital, took up a substantial amount of storage space and after accounting for all the overhead expenses, Asher was surprised to learn net proft was barely measurable.
To make matters worse, Asher was forced to install an elaborate security system after several cars were damaged by vandals. All these factors made Cadillacs a poor fit within Asher’s diverse business portfolio.
At this point, Asher had some difficult decisions to make. No doubt there’s a viable business model for exotic pet breeders, luxury car dealerships and fruit stands. Asher’s problem wasn't that these products couldn't be profitable—-it was that he was trying to market and sell them alongside completely unrelated products.
‘Fruits, Furs & Fenders’ becomes ‘Heritage Harvest”
A more consistent product line delivers value far beyond mere operational efficiency. When your offerings are naturally aligned, customers develop stronger mental associations with your brand, simplifying their decision-making process and building loyalty.
Perhaps most valuable is strategic clarity. A consistent portfolio provides a better framework for evaluating opportunities and making resource allocations. Rather than chasing every potential revenue stream, a business can confidently decline poorly aligned opportunities, freeing capacity to pursue initiatives with genuine strategic value.
As you might have guessed, this case study ends with Asher rebranding the business into a specialty produce company with substantially higher capacity for profitability and a new identity which his customers had struggled with the in past.
A Few How-to’s
Here are a few suggestions for finding the winners and losers.
Start by examining the hard numbers for each of your offerings. Track how much revenue and profit each generates compared to the resources it consumes. Ask yourself—-is demand growing or declining?
Next, evaluate how your products interact with each other. The strongest business portfolios contain items that create natural synergies. Look for products that attract similar customers, share production resources, or create cross-selling opportunities. Products that require completely different expertise, equipment, or marketing approaches may be spreading your focus too thin.
Finally, categorize your offerings into actionable groups: Stars (high-growth winners), Cash Cows (reliable profit generators), Question Marks (unproven potential), and Dogs (underperformers). This classification makes it easier to develop specific strategies for each category – whether that means increasing your focus and investment, maintaining steady operations, testing improvements, or planning for withdrawal.
And remember: sometimes the best business decision is removing products that drain resources, even if they generate sales. Your goal is creating a focused collection of offerings that complement each other, maximize resource efficiency, and position your business for sustainable growth.
Sometimes Less is More: Time to Count What Counts
Portfolio optimization isn't just about eliminating obvious losers; sometimes it requires making difficult choices between good options and better ones. The most successful business managers understand that portfolio alignment sometimes means saying goodbye to perfectly viable products that simply don't fit your business’ future direction.
As you consider your own business portfolio, remember that the most important decisions rarely involve obvious choices like removing monkeys from a fruit stand. Instead, they require the courage to evaluate even successful offerings against your strategic objectives and to make the difficult calls that will ultimately determine your business's future.
What would happen if you were completely honest about the "monkeys and Cadillacs" in your current product set? Are there any products or services you are holding onto for emotional reasons rather than business logic? What would your business look like if you focused only on your top three performing offerings?
Branding a Business with Multiple Personalities
For the storm chasers and adrenaline junkies, read on.
If you’re going to offer a mix of things, own it. Don’t let your business feel like different hustles stuck together. Instead, create a story that brings it all under one roof. These businesses are typically known as destinations, where your customers might come to buy something, but stay for other reasons.
One of my best examples is a local sporting goods store where the average length of time their customers stay is an average of >3 hours! They offer all the normal sporting goods but also feature quite a few other attractions that reflect a broader goal of connecting people with nature and promoting environmental stewardship.
Take, for example, a motorcycle sales and repair shop that also runs a coffee bar and hosts live music on the weekends. On paper, that might sound scattered. But in practice, it creates a space where motorcycle riders and buyers, creatives, and the curious all feel welcome.
The coffee shop gives customers a reason to stay while they wait for service or want to feel part of the community. The live music creates buzz and a reason to visit. The bikes give the place its edge and identity. Together, they form a vibe. The shop isn’t just buying or fixing motorcycles—it’s about culture.
Turning a mixed business into a true destination can be exciting and memorable, but it comes with real challenges. Owners must create a consistent brand that ties the offerings together, manage complex operations across different offerings, and market the business as a unified experience rather than separate services.
Warning: Time, staffing, and resources can quickly become stretched thin, and it’s easy to confuse customers if the business doesn't clearly speak to a well-defined audience. Success depends on having a strong core identity, clear systems, and a strategic focus on the customer experience that makes the mix feel intentional, not random or accidental.
Contributed by Richard Talbot | April 2025
