A more risky investment doesn't necessarily need to have a downside as in loss, just the possibility of earning less than a less risky asset.
Let's walk through a simplified example - please tell me which parts are not clear.
Suppose we have a choice of two investments. The "riskless" investment costs $1 now, and is certain to be worth \$2.50 in 1 year. The "risky" investment is known to have a 1/3 probability of being worth \$1.50 in 1 year, and 2/3 probability of being worth \$3. in 1 year.
(Of course in real life you have a choice of many investments more or less risky; some can actually lose money; but you don't really know the probabiliy of their having any particular return. The possible returns may or may not even be bounded above or below.)
Since we're given these made-up probabilities, the well-known formula for the "expected value" of this risky investment worth in 1 year is 1/3 * \$1.50 + 2/3 * \$3. = \$2.50 - same as the riskless asset (I made up the numbers to make them match).
So, what should the risky investment be worth today?
This is not a math or finance question. Rather it's a human psychology question. A pretty common job interview question is some version of "Suppose we throw a 6-faced die. If 1 comes up, you pay me \$2. Else (if 2..6 comes up), I pay you \$4. How much would you pay to play this game?" You can see that the expected value of the payoff is $-\frac{1}{6}\times 2+\frac{5}{6}\times 4=1$. But how much someone would be willing pay depends on their risk aversion.
Depending on the circumstances, including the size of the investment, the risky asset may be trading at lower or higher price than the riskless investment with same expected value. For example, in case of lottery tickets, lots of people pay a dollar or two for a lottery ticket whose expected value (the probability of winning $\times$ the jackpot) is less than the cost of the ticket (except for rare large jackpots). Likewise, many people have good time gambling at casinos, knowing that their winnings are likely not offset their losses. Under these circumstances, the investors are willing to pay more for a small chance of winning more money than keeping a riskless dollar in their pocket would.
"Negative" risk premium means that the risky investment trades at a higher price than a riskless investment with the same expected value in the future. Or equivalently if the risky and the riskless investment trade at the same price, then the expected value of the (smaller) risky investment in the future is less than that of the riskless investment.
Conversely, "positive" risk premium means that the risky investment trades at a lower price than a riskless investment with the same expected value in the future.
Lottery tickets are usually sold with negative risk premium, except for rare periods when no one wins for a while, and the jackpot becomes huge, and the risk premium becomes positive, and people who don't usually play lottery begin to buy tickets - but the price of the ticket does not change. Another example, if you drive through Connecticut, you may notice billboards advertising casinos on reservations featuring "loosest slots around" with 98% payout. Not a winning investment, even if you're comped all you can eat buffet and hotel room in consolation for losing money. What is the dollar value of a watery "free" drink from a cute underdressed cocktail waitress at a casino? I don't know, but some people seem to overprice it a lot.
But in other circumstances, the investors prefer certainty, and are averse to the possibility of earning less than the riskless investment, so the riskless investment is trading at a lower price than the risky one. This is an empirical observation. When people actually "invest", rather than "gamble" for entertainment purposes, they prefer positive risk premium. The larger the amount, the more risk averse they get. But concepts like "large" and "my utility of knowing that I won't earn less than the riskless investment" and "my utility of a chance to earn more than the riskless investment" vary for different market participants.
For example, insurance companies' business model is to find mispriced risks and to take the view that they are mispriced. E.g. most homeowners prefer buying fire insurance to self-insurance. They're willing to pay more for fire insurance to an insurance company than the expected value of self-insurance. A single fire event is traumatic and catastrophic for an individual home owner, but business as usual (meh) for a large insurance company.
For example, put options on stock indices usually trade at negative risk premium because investors buy them as hedge/insurance for tail risk, not as investment.