You have to understand first the context and that is the biased view that Fred has based on the companies he / Union Square Ventures invests in - and for where he'll see the most data from.
Also, you have to define success - and success for who? If you take a larger Series A, that likely means founders are diluting more - and possibly previous investors. The idea being that if you can take as little as possible and find other means to grow and continue to develop product - other than throwing more money at it - then you'll be more 'successful' - whatever success means to you.
If how much you sell a company for is your what you care about, and not how much equity you have out of it - then cool - but 40% of something worth $100 million, is better than 10% of something worth $300 million.
Also, you have to define success - and success for who? If you take a larger Series A, that likely means founders are diluting more - and possibly previous investors. The idea being that if you can take as little as possible and find other means to grow and continue to develop product - other than throwing more money at it - then you'll be more 'successful' - whatever success means to you.
If how much you sell a company for is your what you care about, and not how much equity you have out of it - then cool - but 40% of something worth $100 million, is better than 10% of something worth $300 million.