Five Common Obstacles Entrepreneurs Face—and How to Overcome Them

Mention entrepreneurship to Rockford Weitz, and you will quickly discover that he thinks far beyond the next big startup. As director of the Maritime Studies Program and a professor of the practice at The Fletcher School and a self-described “serial entrepreneur,” Weitz approaches the term broadly, with a definition that encompasses nonprofit founders, policy innovators, and anyone who approaches challenges with agility and creativity.

“Entrepreneurship is problem-solving with limited resources and an unclear path forward,” he says. “That’s true whether you’re launching a cutting-edge app, starting a social impact nonprofit, or building a small team within a larger organization.”

His expansive outlook informs Fletcher’s new graduate certificate in business. The program blends global business perspectives with a focus on practical skills, and includes offerings like Weitz’s Entrepreneurial Leadership: Starting New Ventures course, which immerses students in developing ideas, refining business models, and pitching in real-world settings.

In his classroom, students’ ambitions may differ: some are ready to launch immediately, while others are preparing for the long term. But once they start putting ideas into practice, they confront the same kinds of obstacles. 

“Whether you’re looking to run a small nonprofit or to launch a big company, the challenges tend to be the same,” Weitz says. “And the skills to overcome those challenges are remarkably transferable.”

He speaks from experience. Over the past 25 years, Weitz has led private-sector startups, tech-oriented nonprofits, and what he calls “academic startups,” like the maritime program he runs at Fletcher. Those ventures have sharpened his understanding of the hurdles every entrepreneur faces and the best strategies for clearing them.

Weitz spoke with Tufts Now to share insights about those hurdles and to offer his advice for surmounting them.

1. Getting Started

The most universal roadblock? Taking the first step. “People say, ‘I’ll do it after I graduate,’ or ‘Once the kids are older,’” says Weitz. “But there’s almost no downside to starting while you’re in school” (except, he jokes, the risk of neglecting coursework).

For Tufts students, timing a launch to align with the Tufts New Ventures Competition creates a built-in deadline and a powerful motivator. In his fall semester course, Weitz guides students through a step-by-step process that turns a raw idea into a market-tested pitch by the time the competition deadline arrives in early spring.

That process is “a way of breaking a daunting project into manageable stages,” he says. “By the end, you’ve thought through your market, your customer, and your team, and you have something concrete to move you forward.”

2. Prioritizing for Progress

But once you’ve started, another challenge quickly takes over: finding enough hours in the day. Early-stage startups face endless to-do lists with tiny teams, notes Weitz. Small founding teams often have to work at the pace of much larger organizations with only a fraction of the resources.

The key, he says, is ruthless prioritization. Entrepreneurs have to decide what truly moves a venture forward in any given moment.

For most, that begins with developing a minimum viable product, the simplest version of an offering that will attract real customer feedback. “It doesn’t need all the bells and whistles,” Weitz says. “Get something in front of people, learn from it, and iterate. That’s the build-measure-learn loop of entrepreneurship.”

3. Managing Finances and Cash Flow

Prioritization can keep a young venture on track, but eventually, every founder runs up against the same reality, Weitz says: even the best ideas need money to survive.

Weitz offers one example from Peter Sacco, F17, who launched Adelante Shoes, a social impact footwear company, as a Fletcher capstone project several years ago. At first, the venture struggled to stay afloat. The founder tapped personal connections in Guatemala to source handcrafted shoes at fair wages, priced them competitively for U.S. buyers, and supplemented funding with help from people close to him. 

Now in his early thirties, he has built a thriving enterprise. “He found ways to make it work financially while staying true to his mission,” Weitz says.

That kind of resourcefulness is essential for any new venture, Weitz adds. No matter the field, money will be tight at the start, and the difference between surviving and folding often comes down to disciplined spending and creative problem-solving. “Can you get something for free through your network? Can a friend help set up your website? The more you extend your runway, the better your odds.”

4. Building the Right Team

Getting a venture off the ground also takes the right people, says Weitz. As he puts it, “the most successful startups are powered by small, diverse teams.”

Early-stage enterprises thrive with three to five co-founders whose skills complement each other, he explains. “You don’t want three salespeople. You want someone who can sell, someone who can handle operations, and someone with technical know-how.”

And team dynamics matter as much as skill sets. You have to get along, he says, stressing that getting along is a skill like any other. “It takes practice, and practice makes better—not perfect, better. Every project is a chance to learn how to recruit, collaborate, and manage effectively.”

5. Finding Allies and Partners

While resourcefulness and teams may launch a venture, connections often determine whether it grows. But, says Weitz, many entrepreneurs hesitate to reach out for support.

“Get past the hesitation and ask for help,” he advises. “If you think creatively about your network, you’ll find people with expertise who can save you time and money, and who are more than willing to do so. People like to help.” For students, that might mean leaning on mentors, classmates, or alumni; for seasoned founders, it might mean drawing on colleagues or collaborators in other fields.

What matters, says Weitz, is learning to view relationships as part of the venture itself. Allies bring not only advice or technical know-how but also the momentum that comes when others believe in your idea. It’s a lesson he hopes every student carries beyond Fletcher: entrepreneurship is never a solo act. As you’re charting your unclear path, you can turn your ideas into action, as long as you have the help of others.