Chaddha's process prioritizes deep relationship-building over transactional speed. He requires at least 10 hours of interaction, including dinners, to gauge a founder's character, respect, and long-term partnership potential, filtering out those just seeking quick money.
In a non-control deal, an investor cannot fire management. Therefore, the primary diligence focus must shift from the business itself to the founder's character and the potential for a strong partnership, as this relationship is the ultimate determinant of success.
Founders can accurately gauge an investor's future helpfulness by their actions during the pre-investment courtship phase. If an investor is unwilling to provide value when they are most motivated to win the deal, they are unlikely to be a helpful partner later on.
A compressed diligence process relies heavily on projections. A superior approach is building a relationship over 1-2 years, which allows an investor to witness the company's actual execution against its stated goals, providing far greater conviction than any financial model.
To predict the future health of a partnership, intentionally have difficult conversations before any investment is made. If you can't productively disagree or discuss serious problems before you're formally linked, it's highly unlikely you'll be able to do so when the stakes are higher post-investment.
To win highly sought-after deals, growth investors must build relationships years in advance. This involves providing tangible help with hiring, customer introductions, and strategic advice, effectively acting as an investor long before deploying capital.
Rather than imposing processes after investing, VCs can use frameworks like the "sales sprint" as a pre-investment litmus test. Sharing the approach and observing the founder's reaction reveals their mindset. A founder who is eager to adopt a disciplined, customer-centric process is a stronger bet than one who must be forced into it.
For proactive deal sourcing, the initial contact is a high-stakes sales call. F5's Andy Cohen invests 2-10 hours researching a target before the first outreach. This deep dive into podcasts, blog posts, and mutual connections enables a substantive, flattering conversation that builds immediate rapport and credibility.
Engaging with founders a month before Demo Day, even without a formal pitch, provides a vital baseline. Witnessing their spectacular progress over that month creates a powerful second data point on execution velocity, making the investment decision far easier and more informed.
Interviews can be misleading as founders are skilled at presenting well. Venture investor Naveen Chaddha relies heavily on extensive back-channel references to create an "X-ray" of a founder's history. He believes that while founders can craft a narrative, they cannot hide from their past actions and reputation.
The most effective fundraising strategy isn't a rigid, time-boxed "process." Instead, elite founders build genuine relationships with target VCs over months. When it's time to raise, the groundwork is laid, turning the fundraise into a quick, casual commitment rather than a competitive, game-driven event.