The phrase "riskier pick" means choosing something or someone that has a higher chance of not being successful or causing problems compared to other options. Full definition
Admittedly this is a slightly risky pick — taking a raw prospect from a small school is always a gamble — but the upside here is just too much to pass up. (sbnation.com)
As he outlines on his stats website, figure out who your competition is picking and pick the opposite, making riskier picks the bigger your pool is. (sciencenews.org)
The second part is called the «dividend growth stock addition» where I might ignore one of the metrics mentioned in principles # 1 to # 5 for a greater upside potential (e.g. riskier pick as well). (dividendmonk.com)