When the Cookie Jar Goes Around … Take Twice

Striking the Right Balance and the Cookie Jar Principle

As an experienced entrepreneur who has navigated the startup landscape, I’ve had my fair share of encounters with the fundraising dilemma. I’ve seen both sides of the coin – startups raising funds when they desperately need it and those raising capital when they don’t necessarily need it. The truth is, there is no one-size-fits-all approach to fundraising, and the right balance depends on your startup’s unique circumstances. In this post, I will discuss the pros and cons of both perspectives and introduce the Cookie Jar Principle to help you make an informed decision.

The Cookie Jar Principle

Imagine a cookie jar being passed around at a party. When it comes to you, you have the option to take one cookie, two cookies, or none at all. In the context of fundraising, taking one cookie represents raising just enough funds to meet your current needs, while taking two cookies signifies raising extra capital as a buffer for future growth and potential challenges. Opting for no cookies means bootstrapping your startup and relying on your resources.

This principle highlights the importance of striking a balance between raising funds when needed and being strategic about securing additional capital for future growth and stability. Let’s delve into the pros and cons of both perspectives to understand how the Cookie Jar Principle can guide your fundraising decisions.

When You Really Need the Capital


  1. Access to funds allows you to execute your growth plans and expand your startup.
  2. Investors can provide valuable connections, resources, and expertise to help your startup succeed.
  3. Raising funds can boost your credibility and signal confidence in your startup to potential customers and partners.


  1. Dilution of ownership and control – as you raise more funds, you might give up a significant stake in your startup.
  2. Increased pressure to meet investor expectations and deliver high returns.
  3. The fundraising process can be time-consuming and distracting from your core business operations.

Raising Capital When You Don’t Necessarily Need It


  1. Having a financial buffer allows you to take calculated risks, pursue new opportunities, and weather unexpected challenges.
  2. Raising capital at a time when you don’t need it can give you better negotiating power and potentially secure more favorable terms.
  3. Access to additional funds can enable you to scale your business faster and more aggressively.


  1. Raising funds when not needed might lead to complacency and poor financial discipline.
  2. The dilution of ownership and control can still be an issue, even if you’re raising funds from a position of strength.
  3. There’s a possibility of attracting investors who may not be the right fit for your startup.

Striking the Right Balance with the Cookie Jar Principle

The key to striking the right balance between these two perspectives lies in understanding your startup’s unique needs and circumstances, and considering the Cookie Jar Principle as a guide. Ask yourself these questions:

  • Do I have a validated product-market fit and traction to demonstrate to potential investors?
  • Is my startup’s growth potential limited by a lack of capital?
  • Am I prepared to give up some control and ownership in exchange for funding?
  • Do I have a plan in place for how I will use the funds to drive growth and create value?
  • Am I in a position to take two cookies from the jar, securing extra capital for future growth and stability?

By reflecting on these questions and considering the pros and cons of both perspectives, you can make an informed decision about whether or not to raise funds for your startup. The Cookie Jar Principle serves as a reminder to be strategic and forward-thinking in your fundraising approach. Remember, there is no one-size-fits-all solution, and the right balance depends on your unique situation. Stay humble, learnfrom your experiences, and remain adaptable as you navigate the complex world of startup fundraising. Embrace the Cookie Jar Principle to strike the right balance and set your startup on a path to success.

In conclusion, the fundraising journey for startups is a delicate balancing act. It’s crucial to recognize that every startup’s situation is unique, and the right course of action will depend on several factors. The Cookie Jar Principle is a valuable tool to help guide your decision-making process, allowing you to determine the right balance between raising capital when needed and being strategic about securing additional funding for future growth and stability. By carefully considering your startup’s needs, growth potential, and current circumstances, you’ll be better equipped to make informed decisions that will benefit your venture in the long run.

Stay humble, and always be open to learning and adapting as you navigate the ever-changing landscape of the startup world.