An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.

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.

Counterintuitively, targeting significantly larger deals forces extreme focus. A $5 billion fundraising goal might involve only 10 conversations, whereas a $5 million goal could involve 1,000. This massive scale filters for serious professionals and eliminates the distractions common in smaller-scale endeavors, simplifying the process.

Fundraising isn't a single transaction. A top Japanese VC prefers to invest in founders he's known for over two years, valuing trust built through long-term relationships over a polished fundraising pitch.

Despite headlines about rapid-growth companies, the typical startup journey is slowing dramatically. The median time between Series A and B rounds is now close to 1,000 days (almost 3 years), creating a barbell market where a few companies raise quickly while the majority face a much longer path to their next milestone.

With fundraising rounds closing in weeks instead of months, investors can no longer conduct exhaustive diligence on every detail. The process has become more efficient by treating the current business model as table stakes and focusing limited time on underwriting the core thesis for future, non-obvious growth.

Thomas Mueller-Borja demystifies large-scale fundraising by breaking it down into a numbers game. To raise $2 billion with an average ticket of €50 million, you need 40 investors. Assuming a 20% conversion rate, this requires building and maintaining a prospect funnel of 200 global leads.

The founders of Free Soul endured multiple rejections, including literally being laughed out of rooms. They frame this brutal process as a necessary filter that weeded out misaligned VCs and ultimately led them to investors who were personally connected to their mission.

Instead of a formal roadshow, founders should let future lead investors invest small amounts months in advance. Providing them with regular updates and hitting stated milestones builds immense trust, making the actual fundraise a quick, targeted process that optimizes for partner over price.