The Entrepreneurial Marketer: Lessons from Innovators Who Took Bold Risks

In the world of marketing, the line between success and failure is often defined by one thing: risk. While most brands stick to safe, proven strategies, the ones that make a lasting impact are those willing to take bold, calculated risks. This entrepreneurial mindset, often found in the most disruptive marketers, is what transforms ordinary campaigns into extraordinary movements.

In this article, we’ll explore examples of marketers and brands that took risks—and how you can adopt an entrepreneurial mindset to push your brand forward. I’ll also share my own experience with City Delivery/FoodPanda and actionable steps you can take to embrace risk and innovate in your marketing strategy.

The Entrepreneurial Marketer Mindset

Entrepreneurship isn’t just about starting new businesses; it’s about thinking differently. The entrepreneurial marketer takes risks, not recklessly, but strategically, understanding that every risk comes with learning opportunities. Risk-taking fuels innovation and can lead to immense brand loyalty, especially when it resonates with your target audience.

Back in 2012, when I was leading the transformation of City Delivery, a call center-based food ordering company, into what eventually became FoodPanda, we faced a similar decision. At that time, the idea of food delivery through digital platforms was still relatively new in the Philippines. Most customers were accustomed to dialing a hotline to order food.

Recognizing the potential to streamline the service, I pushed to transform the company into a fully digital platform, introducing innovative features like rider tracking and app-based ordering—years before it became the norm. This was a risky move in a market that wasn’t quite ready for such a transformation, but I knew that taking this step would create a competitive edge, improve the customer experience, and set the company up for future success.

The risk paid off, and today, the digital-first model is standard across the industry, allowing brands like FoodPanda to dominate the market.

Case Study 1: Apple - Defying the Status Quo

Apple is perhaps the most well-known example of a brand that thrives on innovation and risk-taking. Steve Jobs’ decision to focus on premium, design-led products when the market was dominated by cheaper, mass-market electronics was a monumental risk. The launch of the iPod, iPhone, and later the iPad transformed not only Apple’s business but entire industries.

Apple’s focus on brand identity over short-term sales has resulted in one of the most loyal consumer bases globally. This risk-driven approach has led Apple to become the world’s most valuable company, with brand loyalty that other brands envy.

Key Takeaway: Don’t just follow market trends. Create your own. Take risks that align with your brand’s values and identity, even if it means swimming against the current.

Case Study 2: Gojek – From Ride-Hailing to Super App

Another prime example of bold, risk-taking in Southeast Asia is Gojek, the Indonesian ride-hailing giant turned super app. When Gojek started as a motorcycle ride-hailing service in 2010, it was taking on Indonesia’s chaotic transportation system. But their decision to rapidly diversify into food delivery, financial services, digital payments, and logistics was a monumental risk—especially in a fragmented market.

The company didn’t stop at transportation. Gojek’s pivot into becoming a super app allowed it to provide everything from food delivery (GoFood) to digital payments (GoPay) and even logistics (GoSend). While there were risks of overstretching the brand, Gojek succeeded in integrating various services into one seamless platform that catered to the everyday needs of its users.

A significant part of their risk-taking involved GoPay, Gojek’s digital payments system, which quickly became one of Indonesia’s most widely used e-wallets. The investment in GoPay was a risk, as it ventured into financial services, an area outside of Gojek’s original expertise. However, the risk paid off, with GoPay now contributing significantly to Gojek’s overall revenue and ecosystem.

Gojek’s willingness to expand aggressively, invest in multiple service verticals, and create an all-in-one app in a market that was still developing digital infrastructure is what led to its massive success.

Steps to Cultivate an Entrepreneurial Mindset:

Here are some actionable steps you can take to start thinking like an entrepreneurial marketer:

Challenge the Status Quo: Always ask, “Why are we doing it this way?” Entrepreneurs look for better, smarter ways to solve problems and don’t settle for doing things just because “that’s how they’ve always been done.”

Embrace Failure: Every risk carries the possibility of failure, but entrepreneurs see failure as a stepping stone to success. Learn from it, and use those lessons to refine your next move.

Be Customer-Centric: Focus on what your customers need, not just what’s easiest for the business. Entrepreneurs succeed because they solve real-world problems for their consumers.

Innovate Consistently: Innovation isn’t a one-time event. Cultivate a culture of continual improvement and iteration within your brand, constantly looking for ways to disrupt your industry.

The Reward of Risk: Brand Differentiation

The biggest reward of taking risks is brand differentiation. In today’s crowded market, consumers are bombarded with options. If your brand doesn’t stand out, it gets lost. But when you take risks—whether it’s through your messaging, your campaigns, or your products—you give consumers a reason to choose you over your competitors.

And here’s something important to remember: Consumers love bold brands. Brands that are willing to take a stand, be authentic, and push boundaries are the ones that earn brand loyalty. When you show your audience that you’re not afraid to be different, you build trust. And trust leads to loyalty.

To stand out in today’s crowded market, Filipino and Southeast Asian brands need to adopt an entrepreneurial mindset that embraces calculated risks. Whether it’s through bold product decisions, innovative brand voices, or disruptive marketing campaigns, the only way to leave a lasting impact is by daring to be different.

So, take a moment today to ask yourself and your team: What’s the next bold move our brand can take?