How to Make Your Startup Pitch Compelling: Insights from Leland’s Fundraising Panel

September 27, 2025

Fundraising is one of the hardest—and most misunderstood—parts of building a company. Founders often assume success comes down to flashy slides or the right introductions. But in reality, the most compelling pitches go deeper.

That was the central theme of a recent webinar hosted by Leland, featuring Louis Carrington, Co-founder and Marketing Director at Windfall Bio (a company using microbes to convert methane into fertilizer), and Jimmy Monaco, founder of Caserta and former Harvest Global professional. The discussion, moderated by Nick Van Slooten (ex-YC/Relay, now with Leland), offered practical insights into what investors actually look for—and how founders can prepare.

What Makes a Pitch Stand Out

Investors, the panelists stressed, care far less about polished theater than about clarity of execution. A compelling pitch includes:

• Roadmap clarity. Show how you’ll execute, not just what you dream of.

• Team strength. A strong, credible team often outweighs an early, imperfect idea.

• Authenticity. Passion resonates more than jargon; tell a personal, memorable story.

• Differentiation. Unique framing, demos, or even language can help you stand apart.

• Investor alignment. Tailor your pitch to the specific interests of each fund or partner.

  
  

Louis summarized it well: leave investors with “one clear, memorable message” that they can easily repeat when discussing your startup afterward.

Building Investor Relationships

Fundraising is not just about the pitch—it’s about relationships. Louis encouraged founders to expand their “surface area for luck” by networking widely and sharing openly. Jimmy emphasized intentionality: targeting the right investors, focusing on those who can bring strategic value, and building genuine partnerships.

Misconceptions About Fundraising

One of the most valuable parts of the discussion was the debunking of common myths:

• Myth: You must have everything fully planned. Louis argued adaptability matters more than rigid plans.

• Myth: Fundraising is a quick step. Jimmy countered that it’s a full-time job—and that “maybe” from an investor almost always means “no.”

  
  

Both agreed: raising capital isn’t inevitable. Bootstrapping, seed-strapping, or raising only when capital is essential (especially in hardware-heavy businesses) can be smarter than defaulting to a funding round.

The Realities of Diligence and Term Sheets

For early-stage founders, diligence doesn’t mean assembling a full data room—but it does mean having models, unit economics, and projections ready. Later stages require more structure.

Jimmy also cautioned founders to look carefully at term sheets, particularly super pro rata rights, board control shifts, or excessive reporting requirements. The advice was unanimous: invest in strong legal counsel to avoid future traps.

Handling Rejection

Rejection, the panelists reminded, is inevitable. Louis advised treating “no” as data, not defeat. Jimmy reinforced the importance of resilience: it only takes one “yes” to move forward. But if rejection is consistent, founders must be brutally honest and pivot.

The Big Takeaway

Fundraising is never just about the numbers or the slides. As Jimmy put it, “People remember how you made them feel more than what you said.” A founder’s ability to tell a credible, authentic, and personal story—backed by solid execution—remains the most compelling pitch of all.

Sources

• Leland Webinar: Fundraising Lessons and Investor Pitching (Panel with Louis Carrington, Jimmy Monaco, moderated by Nick) – Leland

• Wasserman, N. (2012). The Founder’s Dilemmas. Princeton University Press.

• Graham, P. (2008). How to Pitch Startup Investors. Y Combinator Essays