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Experiences of Repeat Entrepreneurs: Streamlined Approaches, Amplified Influence

Redefining my journey, the recurring realization is this: when facing situations a second time, it's not about doing more, but rather about doing less, yet with improved quality.

Experience with Multiple Startups: Fewer Actions, Greater Impact
Experience with Multiple Startups: Fewer Actions, Greater Impact

Experiences of Repeat Entrepreneurs: Streamlined Approaches, Amplified Influence

Milad Monshipour, a seasoned entrepreneur, has shared insights into the key differences between starting a first business and a second one. His journey, spanning from co-founding TAPSI, Iran's first tech startup IPO, to leading AIR, an AI-powered real estate brokerage in the UAE, offers valuable lessons for aspiring entrepreneurs.

The First Business: Ambition, Experimentation, and Uncertainty

Monshipour's first venture was marked by ambition, experimentation, and significant uncertainty. It was a period of trial and error, with the challenge of creating real value for customers and stakeholders. The process involved learning how to develop a desirable product and navigating the unknowns related to product-market fit and operational challenges.

The Second Business: Achieving Goals with Greater Efficiency

In contrast, the focus of the second business was on achieving goals with greater efficiency. Monshipour emphasizes better management of product development processes, more effective alignment of team capacity with project milestones, and a laser focus on areas that deliver maximum value. The feedback loop improves, enabling faster iterations and improvements based on useful data.

Impactful and Strategic Marketing

Another significant advantage when launching a second business is the existing relationships, reputation, and trust built from the first venture. This network accelerates momentum since it reduces the challenges involved in forging new connections and makes collaborating with individuals and the wider community smoother and more productive. Moreover, Monshipour found he was able to create more impactful marketing by learning which methods and timing yield the highest returns, thereby saving time and resources while avoiding mistakes.

Leveraging Established Networks

One of the most underestimated advantages of starting a second venture is the network and reputation the entrepreneur brings from their first business. Monshipour's second business benefited from a stronger and broader reputation, higher level of trust, and a better network of connections. This made recruiting new talent for the second business easier, and previous collaborators were able to be brought on board.

Experience and Evolution

Experience helps in second-time entrepreneurship, but it's not about repeating what was done before. It's about reinventing the approach with a sharper focus and a deeper sense of responsibility. Monshipour had a clearer understanding of the landscape in his second venture, and he was more attuned to the feedback process, knowing how to elicit honest and useful data to drive improvement.

Launching a Business: First Time vs. Second Time

Launching a business for the first time is fueled by ambition, experimentation, and uncertainty. The challenges don't go away when starting a second business, but the mindset, methods, and approach evolve. Legal structures in the second venture became a tool for momentum, not an obstacle. Well-designed legal and shareholding structures were approached with more clarity in the second venture.

In summary, while the first business demands learning and experimentation, the second business benefits from experience, refined execution, and leveraging an established professional network to create bigger impact more efficiently. This comparison is drawn directly from Monshipour’s reflections on his journey, offering valuable insights for entrepreneurs embarking on their own ventures.

  1. Monshipour's first business was marked by ambition, experimentation, and significant uncertainty, a period of trial and error that involved creating real value for customers and stakeholders.
  2. In contrast, his second business was focused on achieving goals with greater efficiency, with better management of product development processes, more effective alignment of team capacity with project milestones, and a laser focus on areas that deliver maximum value.
  3. Monsharepour found that his existing relationships, reputation, and trust built from the first venture were extremely beneficial when launching the second business, as it accelerated momentum and made collaborating with individuals and the wider community smoother and more productive.
  4. The network and reputation the entrepreneur brings from their first business can make recruiting new talent for the second business easier and enable the entrepreneur to create more impactful marketing by learning which methods and timing yield the highest returns.
  5. Experience in second-time entrepreneurship is not about repeating what was done before, but about reinventing the approach with a sharper focus, a deeper sense of responsibility, and a clearer understanding of the landscape, allowing the entrepreneur to be more attuned to the feedback process and drive improvement more effectively.

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