All investments involve risk, and Bitcoin is no exception. However, your view focuses heavily on the potential for success stories – those who've held Bitcoin since its inception and reaped significant rewards. This paints an optimistic but incomplete picture.
His views are focused on the success stories because that's the reward for hodling Bitcoin, and he's trying to establish a positive future for hodling Bitcoin which he isn't wrong because Bitcoin has proven numerous times that its hodlers never regrets that's why hodling will always be the best strategy to invest in Bitcoin. Bitcoin has its risk but when calculating the risk to reward ratio, Bitcoin is far more a better investment when you buy and hodl and not having a short time investment mentality. There's more success story when you hodl Bitcoin irrespective of how the market moves because at the end of the day, Bitcoin always reward its hodlers.
The "win-win" situation applies only with hindsight. For early investors, holding was a wise strategy. But for those who bought at the peak of a bull market, the wait for profits can be agonizing, especially during prolonged downturns.
The win-win situation doesn't apply only with a hindsight, you can know that hodling will give your profits from past investors. Bitcoin is no longer a new investment that doesn't have a history that you can look at. Those that are hodling end up being in profits so if you want to have a win win situation, you can just hold and not get bothered about the movement of the market. Those that bought at an early stage of Bitcoin (let say when Bitcoin was at its lowest) and those that bought at the peak of a bull run can all benefit if they hodl provided both investor have the patience to wait. The rollercoaster experience is part of the journey of investing in Bitcoin.