David Cummings

Last week, I caught up with an entrepreneur who shared one of his recent lessons learned about the unintended consequences of throwaway comments as a founder. In the early days of a startup, everyone is involved in everything—from frontline tactics to strategic initiatives. However, as the startup grows, more team members are brought on, and specialization gradually increases. Over time, teams and individuals are assigned to implement and manage different projects within the organization.

This transition—from everyone doing everything to a more mature, scalable organization—requires founders to pay closer attention to their comments and ideas. It’s easy to be the loudest voice in the room, especially in a small team, but this often leads to other team members holding back their thoughts or feeling that enough has already been said. Over time, this dynamic can escalate. Eventually, founders may find that their casual comments or quick ideas are taken as urgent directives, leading to unnecessary or premature actions.

I’ve experienced this myself. For instance, I might casually say, “Why don’t we try this approach?” or “We should add this feature,” without fully thinking it through. A week or two later, the team might come back with the suggestion implemented, and I realize I didn’t weigh the pros and cons carefully. What I thought was an offhand remark turns into completed work—work that may not have been the best use of time.

This disconnect often happens because expectations weren’t clearly set. To address this, I’ve learned to encourage team members to speak first and make a point to speak last in group settings. Additionally, when I share ideas or suggestions, I preface them by saying they’re just ideas, part of a brainstorming session, or potential directions to explore. Over time, I’ve become more mindful of setting expectations—clarifying whether I’m sharing an idea for consideration or giving a directive that requires action.

Of course, how and when these distinctions are communicated may vary depending on the personalities and work styles within the team. Repetition and consistency are often necessary to ensure clarity. As a founder of a growing organization, it’s inevitable that a throwaway comment will sometimes be taken as a high-priority order. This makes it all the more important to communicate clearly and distinguish between brainstorming and actionable plans.

In the early days, throwaway comments might not seem like a big deal. But as the company scales, founders need to be deliberate in communicating their ideas and recommendations, ensuring their intentions are understood. A clear distinction between casual brainstorming and actionable directives helps the team prioritize effectively and avoid wasted effort.

Last week, I was talking to an investor about an entrepreneur he really enjoyed working with. Hearing the joy in his voice, I inquired about what made the experience so delightful. He said it was the quality of the entrepreneur’s interactions.

This idea has been on my mind ever since: the quality of interactions. After asking more questions and exploring the idea myself, here are a few examples of quality interactions between an entrepreneur and an investor:

1. Timeliness of Response

Whether it’s a phone call, email, or text, responsiveness matters. Of course, there’s always a lot going on, but some people manage their responsiveness better. Even if they don’t have time for a full conversation, a quick message like, “I’m tied up for the next few hours (or the day), but here are some good times to catch up,” or “I’ll get back to you by [specific time],” goes a long way. Quick, clear communication builds trust.

2. Thoughtfulness on Unknown Questions

Investors frequently ask entrepreneurs questions they might not immediately know the answers to:

What does this customer cohort look like? How has this spend changed over time? Where is the market headed in this sub-segment? It’s normal not to have all the answers. However, some entrepreneurs try to answer everything, even when it’s clear they don’t know. It’s much better and more thoughtful to respond with something like, “Great question. I don’t know the answer to that, but I’ll research it and get back to you.” Acknowledging what you don’t know and committing to follow up shows maturity and professionalism.

3. Enthusiasm and Passion

While entrepreneurs are generally optimistic—sometimes to a fault—those who demonstrate genuine passion and excitement are more enjoyable to interact with. That said, entrepreneurs shouldn’t fake enthusiasm, but ramping up energy and excitement within a natural spectrum of authenticity can make a big difference.

4. Effort in Materials

Investors often request board decks, data room access, financial models, etc. Everything an entrepreneur sends to an investor reflects their leadership, even if they didn’t create the document themselves. Typos, grammar mistakes, or low-quality work can reflect poorly on the business. With today’s AI tools, it’s easier than ever to ensure high-quality output. Taking the time to deliver polished, accurate materials builds credibility.

5. Rhythm of Communication

Investors value reliability and consistency in communication. Regular updates, such as a weekly email or monthly snapshot, can keep investors informed and confident in the business’s progress. Unfortunately, most entrepreneurs don’t take this proactive approach, leaving investors to request updates. Entrepreneurs who develop a consistent communication rhythm—showing transparency and reliability—provide peace of mind and demonstrate that these habits will continue as the business grows.

People like to work with others who are thoughtful, conscientious, and care about the quality of interactions. This dynamic is especially important in relationships between entrepreneurs and investors, which often span many years or even decades.

Recognizing the importance of timeliness, thoughtfulness, enthusiasm, effort, and consistent communication can significantly strengthen these relationships. Entrepreneurs would do well to evaluate their current level of interaction and look for opportunities to enhance or improve it.