Chaos to Cultivation
How investors can nurture startup growth
Happy Thursday (and Happy New Year), 👋
In the world of startups, appearances can be deceiving. To outsiders, polished pitch decks, aspirational visions, and confident founders paint a picture of clarity and precision. But behind this facade often lies the chaotic and messy reality of startup life. For angel and venture capital investors, the ability to embrace and navigate this chaos can mean the difference between becoming a trusted advisor or a barrier to progress.
Being a supportive venture capital investor is much like being a good gardener. The goal is to create an environment where plants, or startups, can thrive by offering nourishment and removing weeds, but letting them grow at their own pace. Any seasoned gardener knows that pulling on plants doesn’t make them grow faster and often destroys the garden.
The Messy Reality Behind the Curtain
Most startups thrive on chaos. Their organizational structures are flexible, processes are frequently re-evaluated, and teams often adapt dynamically as needed. While this lack of formality may unsettle investors used to corporate discipline, it’s also the secret sauce of startups. Their ability to pivot rapidly, act decisively, and align around new ideas is precisely what fuels innovation.
However, this agility comes with a price. Standard operating procedures may be lacking, financial models could be unreliable, and internal communication might often seem chaotic rather than harmonious. Understanding and accepting this is the first step toward becoming a productive venture partner.
The Investor’s Role: Be the Gardener, Not the Guardian
Investors often feel an urge to impose order on the startups they support. The apparent chaos can seem like an obstacle to sustainable growth, particularly to those with backgrounds in larger corporations or consulting firms. But micromanagement can stifle the creativity that startups depend on to succeed. Instead, investors should aim to follow these principles:
🚧 Guardrails, Not Guardianship. Startups need boundaries to avoid catastrophic missteps, but within those boundaries, they must have the freedom to experiment. Investors can help define the edges such as legal compliance, financial prudence, and ethical practices, but should resist the urge to dictate every move. It’s often at the edge of chaos where startups discover breakthroughs.
👂 Listen More Than You Dictate. One of the most impactful things an investor can do is listen. In our conversations with startups, founders do most of the talking while we provide subtle guidance to refine ideas or highlight blind spots. The goal isn’t to provide all the answers but to serve as an experienced sounding board.
🤝 Focus on Team Dynamics. Observing how teams function can offer invaluable insights. When invited to company offsites or office visits, our aim is to remain mostly invisible while observing interactions. Are departments collaborating, or do silos dominate? Does the energy shift when leaders enter the room? These observations can reveal underlying issues that founders might overlook.
🚫 Highlight Big Issues Without Being Negative. Rather than getting bogged down in daily operations, focus on identifying significant gaps in strategy, operations, or culture. Help founders address these gaps without being overly critical. Often, teams are aware of the issues but lack the operational experience to implement solutions. Highlighting problems constructively can be transformative.
The Hidden Advantage of Startups’ Messiness
The disorganization within startups can be their superpower. Unlike established companies weighed down by bureaucracy, startups can pivot quickly. Limited financial runway creates urgency, forcing teams to make decisions rapidly and align with minimal friction. This nimbleness should be celebrated, even when it feels chaotic.
Consider Slack. Initially conceived as a gaming platform, the idea floundered. But with only a few months of runway left, the company pivoted to focus on its internal messaging platform. That pivot turned Slack into one of the fastest-growing enterprise tools in history. This success was only possible in an environment where experimentation and quick actions thrived.
Weed and Water
Venture capital operates on a long horizon. Startups don’t grow overnight and attempts to force growth can backfire. We often use a gardening analogy to describe our approach to portfolio companies:
Water and Nutrition: Just as gardeners provide water and fertilizer, startups need resources like capital, mentorship, and connections to thrive.
Weeding: Removing weeds from a garden also allows the plants to thrive. Helping eliminate obstacles, whether toxic team members, poor strategic choices, or market misconceptions, allows startups to grow stronger.
Patience: Pulling on a plant doesn’t make it grow faster; it often destroys it. Likewise, forcing startups to scale prematurely can do more harm than good. True growth takes time, and it’s the investor’s job to nurture the environment without micromanaging.
Final Thoughts: Comfortable Chaos
For venture investors, acting as a mentor and advisor to startups is both a challenge and an opportunity. Behind the perfect pitch deck is often a world of coordinated chaos. Adopting a gardener’s mindset by providing guardrails and allowing startups the freedom to grow is the key to fostering long-term success.
Startups don’t need someone imposing rigid order from above. They need partners who understand that growth is a messy, unpredictable process. By nurturing this process and ensuring ideas have the space to flourish, we as investors can help startups realize their full potential. Like a great garden, success takes time, patience, and care. Remember: pulling on the plants won’t make them grow faster.