In June 2017, just days before stepping down as CEO of Uber, co-founder Travis Kalanick wrote to employees : “If we are going to work on Uber 2.0, I also need to work on Travis 2.0 to become the leader that this company needs and that you deserve.”

What does it mean for an entrepreneur to become a “2.0” version of themselves? As a business grows, the demands placed on its founder grow with it. The knowledge, skills and judgment needed to start a business may not be enough to lead it through its next stage of growth.

This is where entrepreneur development becomes important. If entrepreneurs don’t continue developing as their businesses grow, their own capabilities can eventually become a constraint on growth. They may become the very obstacle preventing their business from moving forward.

Research by former Harvard Business School professor Noam Wasserman , examining 212 American startups, found that fewer than 25% of founders remained CEOs by the time their companies went public. While founders step down for various reasons, the finding is revealing: Most founders in the study were no longer leading their companies by the time they reached this milestone.

Growing Alongside Your Business

The entrepreneur who starts a business is rarely the same entrepreneur who successfully grows it. They may be the same person, but as the business grows, they must become a more capable version of themselves.

Many entrepreneurs launch businesses without formal business training or extensive experience, relying on intuition and learning as they go. As their businesses become more complex, they face new responsibilities, from managing employees and finances to working with stakeholders and making increasingly consequential decisions.

Experience can be a powerful teacher, but it doesn’t guarantee development. Years of managing employees or running a business don’t necessarily make someone a better manager or financial decision-maker. Entrepreneurs must also make a conscious effort to develop the capabilities their businesses require.

As a solopreneur, you may be accustomed to doing everything yourself, from operations and marketing to finance and customer service. As the business grows, however, you may no longer have the capacity to manage everything alone. For entrepreneurs who have never managed employees, building a team requires new skills: hiring, training, delegating, giving and receiving feedback, motivating employees and managing performance.

But acquiring these skills is only part of the transition. Some entrepreneurs struggle to let go when they feel employees cannot meet their standards, often taking work back and doing it themselves. Overcoming this challenge requires developing the confidence to delegate, trust employees’ judgment and give them autonomy rather than dictating every aspect of their work.

Being a good leader doesn’t mean being better than your employees at everything. It means finding exceptional people and empowering them to do what they do best, often better than you could yourself. This allows the business to grow beyond your individual capabilities by drawing on the collective strengths of your team.

Developing Financial Capabilities

Many entrepreneurs start their businesses with limited financial knowledge, sometimes lacking even a basic understanding of financial management. They often learn as they go, from pricing products and managing budgets to understanding equity and negotiating investment terms.

As businesses grow, financial decisions become increasingly complex and mistakes more costly. While some entrepreneurs develop these capabilities through experience, others may struggle to acquire the financial knowledge their businesses require, even after years of running a business. Without that knowledge, they risk making decisions that could significantly harm their companies.

Intentionally developing financial knowledge and skills can better prepare entrepreneurs for these challenges and help them avoid costly mistakes.

A 2026 ⁠ analysis by CB Insights of failed venture-backed startups found that 70% ran out of capital. While running out of money is often the consequence of other business challenges rather than their underlying cause, the finding underscores the importance of financial capabilities in anticipating cash shortages, managing financial risks and maintaining financial stability.

Beyond Technical Skills: Developing Entrepreneurial Judgment and Mindset

Entrepreneur development goes beyond acquiring technical skills. As businesses grow, entrepreneurs must also develop better judgment: knowing whom to hire, which opportunities to pursue, when to say no and how much risk to take. They need to strengthen their interpersonal skills, build relationships with stakeholders and develop the ability to recognize emerging trends and opportunities that others may overlook.

Equally important is a shift in mindset. As their businesses grow, entrepreneurs must learn to move beyond managing day-to-day operations and take greater responsibility for shaping their companies’ future. This requires stepping back from immediate demands, thinking strategically and making decisions that support long-term growth. While operational responsibilities may still require their attention, their primary focus must increasingly shift toward providing strategic direction.

Making Entrepreneurial Development Intentional

Entrepreneurs need to be intentional about their development beyond simply gaining experience, recognizing the gaps between their current capabilities and what their businesses will require in the future.

One question every entrepreneur should regularly ask is: What will the next stage of my business require from me that I haven’t learned yet?

By asking this question, entrepreneurs can proactively seek the knowledge, training, mentors, advisors and experiences they need to prepare themselves for the next stage.

Ultimately, entrepreneur development is not simply about acquiring new skills. It’s about becoming a better entrepreneur—or, as Travis Kalanick might put it, becoming your own 2.0.