Raising Capital as a First-Time Founder: Lessons from Orbit
If you’re contemplating venture fundraising, you’re likely seeking practical guidance grounded in real-world experience. Drawing from my time at Orbit, here are insights that surprised me and may provide useful context as you navigate the process.
Yes Means Yes; Everything Else Is No
A core takeaway is understanding how venture capital firms operate—the psychology and signaling that accompany a fundraising push. VCs often display strong enthusiasm for a deal up until they formally decline or go quiet. If they appear lukewarm, founders can lose momentum and competitiveness in a crowded process.
This dynamic can create emotional whiplash for founders who invest in a relationship that seems to be progressing well. Early in our journey, we allowed perceived excitement to inflate our confidence. We later learned that genuinely interested investors will either opt in immediately or lay out a clear path to the information they need to decide.
Phrases like “Keep me posted on progress” or “Follow up as the round comes together” sound courteous but are not guarantees. It’s important to prioritize attention and energy on the conversations that show clear momentum, and to adjust expectations when early enthusiasm does not translate into commitment.
We chose to attribute this behavior to game theory and incentives rather than cynicism, focusing on the human factors rather than assigning blame.
VCs as Information Hubs
In many meetings, a quick read would reveal whether an investor was inclined to pass. Rather than winding down, some would continue the conversation to extract more information about the market, competitors, or strategic approach.
Before Orbit, my cofounder Josh and I ran a developer relations consultancy. We brought firsthand experience in this space, and we likely educated several VCs about challenges familiar to portfolio companies. Sharing our expertise is valuable, but it’s essential to recognize that access to information is a strategic advantage for VCs—both when compared to other investors and to founders.
Be intentional about what you share and mindful of others’ motivations when they request your time and mental bandwidth.
Your Deck Is Never Finished
A practical method for refining storytelling is to update the deck based on every meeting. Each pitch helped clarify the narrative, reveal confusing wording or charts, and surface supporting data or quotes from investors. We committed to iterative updates, sometimes even en route to the next meeting.
The goal was to remove unclear slides and sharpen core messages. By the end, we had a deck poised to address objections and present a compelling story.
A conversational approach often proved more effective than delivering a memorized pitch. Ongoing edits did not compromise delivery.
Operationally, we maintained multiple internal versions of the deck and used a document-sharing workflow that kept everyone aligned. While some investors still prefer a PDF via email, a centralized link to the latest version prevents outdated references and conflicting conversations.
Strategic note: for some investors, a simple PDF is preferred. Be prepared to accommodate preferences while ensuring the most current version is accessible.
Emotional Rollercoaster: Staying Grounded
Fundraising can elicit a range of emotions. In one stretch, momentum built with two firms—let’s call them A and B. Firm A moved quickly and was later outpaced by Firm B. An accelerated schedule culminated in a strong partner pitch at Firm B, followed by news that Firm A would pass, and then Firm B did as well. The day-to-day pace and the anticipation of competing term sheets can be intense.
Shortly thereafter, a new term sheet from a company you’re excited about arrived, and the overall course of the round shifted dramatically. Maintaining perspective is essential: stay excited about progress, but avoid over-attachment to any single outcome.
Practical strategies included prioritizing exercise, adequate sleep, and a focus on long-term goals rather than daily fluctuations. Keeping perspective helps manage the emotional impact of fundraising ebbs and flows.
Key takeaways for fundraising resilience include building routines that support well-being and emphasizing the broader, strategic path of the company.
Final thoughts
Every fundraising journey is unique, but the patterns above can help you navigate navigating momentum, information dynamics, and storytelling. By staying disciplined, protecting your energy, and iterating thoughtfully on your narrative and materials, you can approach a first-time fundraising effort with greater clarity and resilience.
