In this video, I explain why founders should plan for multiple fundraising and growth scenarios from the moment they raise a round. Plan A assumes hypergrowth toward unicorn status, attracting VCs focused on rapid revenue expansion. Plan B prepares for market downturns, emphasizing unit economics, cash conservation, and profitability, which appeals to a different investor set. Each plan requires distinct forecasting, metrics, and investor targeting to ensure readiness for shifting market conditions.

Founders often overlook team readiness when raising Series A or B rounds. Early-stage companies are typically founder-led, with founders handling all functions. However, to secure downstream funding, investors need to see a scalable leadership team in place—sales, marketing, operations, and especially finance. A strong head of finance or operating CFO is critical, serving as both operator and strategic partner. Top-performing companies with complete, capable teams raise faster, secure better terms, and attract stronger investors. At the expansion stage, VCs prioritize backing proven leadership teams over solo founder-led operations, making team readiness a decisive factor in fundraising success.

Founders raising a Series B must show 2–3 consecutive quarters of strong, sustainable go-to-market execution—not just a single standout quarter. Missing a quarter resets investor confidence, as they want proof of a scalable engine. The biggest red flag is overselling KPIs—misrepresenting growth or retention damages trust once diligence reveals the truth. Instead, be transparent, especially about weaknesses and how you’re addressing them. Investors value honesty and solutions over perfection, and openness often builds more trust than hiding problems. If metrics are strong, lead with them; if not, show progress and a credible plan to improve before scaling.

A strong pitch deck should clearly communicate your big vision, the problem you’re solving, why your team is uniquely qualified, and how your approach is truly differentiated. Treat the deck as a narrative, not just slides of metrics—start by outlining the story you want to tell from beginning to end, then build slides and data to support it. The goal is for investors to leave understanding your vision and wanting to learn more. Test the narrative with friendly audiences, gather feedback, and refine to ensure your message stays consistent and compelling throughout the pitch.

A well-structured data room is critical in fundraising, but timing and content control are key. Ronny Chatterjee advises a two-stage approach: a light data room after the first meeting to gauge interest, and a full data room only once investors are qualified, engaged, and moving toward deeper diligence. Avoid oversharing early, as unqualified VCs may collect data without progressing. Conversely, withholding too much from serious investors can stall momentum. Enhance your data room with context—such as Loom videos explaining key metrics—to guide investors through the story behind the numbers, making your company’s strengths clearer and more compelling during diligence.

This video outlines how to strategically build investor relationships and create a targeted investor list. First, founders should identify their company profile—hypergrowth or capital-efficient—and match with investors whose fund size, check size, and industry expertise align with their needs. Prioritize investors where your company will be important to their portfolio. For companies with top-tier metrics, share high-level updates over time to build trust and momentum. Avoid revealing weak metrics too early to prevent negative first impressions. Structure outreach with tiered lists: Tier 1 (aspirational), Tier 2 (primary targets), and Tier 3 (friendly feedback) to refine your pitch before approaching top choices.

In fundraising, momentum drives competition. Tier investor targets: Tier 3 for early feedback, Tier 2 for setting the pace in diligence, and Tier 1 for aspirational firms to approach once momentum builds. Begin with Tier 3 and Tier 2 to refine the pitch and advance deals, then introduce Tier 1 when multiple firms are in diligence. <br><br>Always notify other investors when someone advances to the next stage to spur urgency and weed out slow movers. Multiple term sheets create leverage, enabling better negotiation on valuation, terms, and selecting the right long-term partner.

In Step 8, Control the Process, we emphasize that successful fundraising requires founders to be proactive and structured. From the first meeting, clearly communicate your fundraising timeline—initial meetings, diligence, partner pitches, and term sheet targets—so VCs know what to expect. <br><br>Avoid giving data without genuine interest and scheduled next steps. Each meeting should have a clear ask and follow-up action. <br><br>Don’t wait for investors to drive the process; instead, maintain momentum through regular check-ins, calls, and trust-building. <br><br>The best founders outline the process early, keep control of pacing, and ensure every interaction moves the deal forward.