It’s Not Failure, It’s Intentional Iteration

Intentional Iteration

There’s an old catchphrase that entrepreneurs are supposed to fail early and often. In order to be innovative, entrepreneurs are told they must not only celebrate success, but also expect and embrace failure. There’s an important lesson in this, but one that gets lost in translation. Businesses will fail. Accepting this and learning from others about the experience of crashing a company are central components of being an entrepreneur.

The predominant use of the word failure frames another important aspect of entrepreneurship that’s little understood and discussed in entrepreneurial circles. The entrepreneur experience is rarely smooth or predictable. It requires intentional iteration and experimentation. Yet, the language given to describe this aspect of the experience is centered around the concept of failure: setbacks, false starts, wrong turns, and mistakes. Many entrepreneurs are just not wired for intentional iteration.

Past educational or corporate experiences do not help them prepare for, learn from, or respond to taking a venture creation step. At its core, iteration is a cyclic process of prototyping, testing, analyzing, and refinement. It’s a way of building knowledge through experimentation. Try something, see what happens, learn from it, and then adapt or pivot. Framed as failure, entrepreneurs develop fear for this part of the experience. Reframing it as intentional iteration allows entrepreneurs to develop the skills needed to respond to the uncertainty they face.


Recognizing that ingrained behaviors may not be of help to an entrepreneur is the first step toward adopting the right mindset. Unlearning habits from prior educational or corporate experiences is necessary, especially when these previous habits conflict with the fast, iterative nature of the entrepreneur experience.

For instance, Michael, an entrepreneur working in San Francisco, has spent most of his professional life working in corporate software development. With his new venture, a mobile app development platform, he’s realizing that tendencies and habits from his prior experience might be preventing him from launching with anything but the perfect product.

Michael worked next to a younger entrepreneur who went from initial idea to a first, and admittedly imperfect, product launch within three months. He realized he’s struggling to unlearn these habits and to manage the tension of wanting to do it right and launching early to get feedback.

Planning to Pivot

Every venture starts off with an idea that will change and develop. A major pitfall is the temptation to overly commit or stick with a particular idea even in the face of certain setbacks.

Entrepreneurs often talk about the importance of identifying a mission that is likely to stay consistent. Scope changes as the venture grows, as customers engage with it, and as it is influenced by the ecosystem. Developing a mission and guiding vision that is malleable enough to anticipate inevitable pivots is critical for success. All ideas change, and entrepreneurs need to keep an open mind toward their capacity to pivot.

Rajiv’s Rhode Island venture started as a local nonprofit focused on raising awareness around health and wellness. It became a for-profit venture that offers social employee wellness platforms to Fortune 500 companies across the country. From his perspective, they’ve always had a commitment to a basic vision, yet how they execute and achieve that vision is still an open and ongoing question.

“You go out there and start something,” Rajiv said. “You know you’re in the right space. We wanted to be in health and wellness; we wanted to be in community development, bringing people together. Along the way you find you start to move down a pathway and identify opportunities.”


Laura, founder of an online marketplace for Twitter tools, described de-risking as a primary business failure strategy. De-risking helped her learn about her product and market iteratively. She identified all the ways her venture might fail, recognized which of these she had some control over, and then incrementally working to address those issues.

“An entrepreneur’s job is to dive headfirst into a really, really risky undertaking and systematically de‑risk it,” Laura said. “Identify what are the six main ways this could fail, and what can I do about. … OK, three of them I can’t control, but these three I can. Let me make progress toward that. … And so, I just kept working all the angles of, well, I can’t do anything about this risk, but I can do something about this.”

The Bootstrap Model

Bootstrapping is more than just shorthand for not seeking outside funding. It centers on constant iteration and leveraging constraint to fuel innovation. The VC model includes writing a business plan, raising capital from investors, growing quickly, and then aiming for a relatively fast exit. In contrast, bootstrapping focuses on shorter cycles of iteration that enable business models to emerge from the process itself. It’s a slower, more organic approach that fully embraces experimentation as the core of the entrepreneur experience. As a methodology, it reframes failure as an essential and productive activity.

While bootstrapping is often seen as an alternative to the VC model, in truth most entrepreneurs, both historically and at present, are in fact bootstrappers. They don’t take outside money, are constantly working with significant resource constraints, and are always iterating and experimenting with their business model.

Leo, a serial entrepreneur based in Austin, Texas, works a full-time job while he steadily iterates his new venture toward launch. He is creating a donation site that allows people to round up purchase costs and donate money to selected social organizations. Leo understands that change in his product and business is inevitable, and he plans for it.

“A very large percentage of what I start with changes,” Leo said. “We refined the strategy. Interviewed donors. Got educated. Got (the) idea out there. Got feedback. Incorporated the feedback we think is important. Circled back to make sure new ideas are the right ones. We know what we launch will need to change again. … You adapt. You grow. You listen.”

Portfolio of Opportunities

Another form of intentional iteration was seen in entrepreneurs who are developing a portfolio of ideas. Instead of focusing solely on one idea, there are individuals actively advancing multiple ventures simultaneously. In other cases, entrepreneurs are designing ventures that create the working conditions and infrastructure for developing a portfolio of ideas centered on a particular space or industry.

For instance, Mike, the founder of a civic software development company in Seattle, describes his venture as a laboratory that is opportunity driven. He intentionally nurtures a culture of experimentation, so that while they’re focused on civic software they’re free to identify and respond to a host of social problems within that space. Mike notes: “If we find the opportunity or there’s some gap in the market that we can get a strong ROI on our particular development skills, consumer Internet skills, then we’ll go jump at that and scale it.”

“There’s a difference between building a product and a company,” he concludes. “A company is a machine that you’re building that can listen to the market and adapt and change from the original ideas.”

About This Research

The Babson Entrepreneur Experience Lab is a partnership between Babson College and the Business Innovation Factory. It is a research platform that puts the voice and experience of real-world entrepreneurs at the center of an ongoing effort to design, develop, and experiment with new education and support solutions that will help shape future generations of entrepreneurs.

More than 250 entrepreneurs launching ventures in the United States were interviewed, offering a glimpse into their everyday lives. We hope their experiences will begin to evolve our understanding of entrepreneurship—to tell new stories that can shape new realities for entrepreneurs of all kinds.

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