1. When to raise? How much to raise?

TL;DR Committing to the equity financing process is a strategic business decision by the founder because of the nature of the ventures and the potential upside of “selling” equity at an early stage of the firm's lifecycle to achieve its competitive advantage.

a. “When you need or don’t need it.”

You may have heard both arguments, but there is no one-size-fits-all answer due to the nuances behind each perspective. The guiding principle is how venture capital money can help founders generate value.

There are three key scenarios of venture capital (or risk capital) that are the most effective in creating value for the ventures for founders:

1. To create a very novel or innovative product or business model with great conviction to succeed financially and
2. To accelerate growth when the revenue model is clear, market validation and acceptance of the product or service are established, and
3. Acquiring other ventures catalyzes growth when it is more expensive and slow to build or reinforces the venture's market position when it is more expensive and slow to do so yourself.

The least effective (or ‘expensive’) way to use venture capital money is to fund the runway of operations (bridging) because the rate of losing money is faster than the cash the business generates.

b. “When you can or as late as you can.”

Founders’ bargaining power always correlates to their ability to deliver venture performance and drive shareholder value. If you raise before traction, you don’t have much to say if you need the money to sustain - you might just take whatever is offered.

Ask yourself: Are you a founder who can still be equally motivated to run the ventures after giving out controls and equity away to finance the growth of the business in multiple rounds?

The answer lies in the ownership (actual share left and intrinsic motivation) you want to hold in counterbalancing the tradeoffs you get to grow the business.

2. What does a VC mean when they say they "bet on the founders / people, not the company".

Inherently VCs want to bet on great founders in a vast market.

Betting on founders is essentially saying “I am betting on someone I trust to return a great deal of money back to me”. This comes in the form of:

• track record of past success;
• history building companies or products;
• has domain knowledge, able to lead a team, sell and be likeable;
• able to do what they said they were going to do;
• great at finding solutions to problems, whether it's a money or people problem.

3. How important is a fundraising deck? Is it possible to raise money from VC just purely from a deck?

The fundraising deck is one of the many key materials you need to communicate your business and your ability to drive fast growth to investors (individual or institutional).

TL;DR It is very unlikely that you will raise a lot of money from a serious investor just from a 10-page pitch deck without any other forms of justification and supporting documentation to show that you can manage the money you are asking for.