Core Insights - The article discusses the biggest money regrets people have shared with personal finance expert Ramit Sethi over his 20 years in the industry, emphasizing the importance of timely investment and financial decision-making [1][2]. Group 1: Investment Regrets - A prevalent regret is not investing soon enough, driven by fear rather than timing the market; Sethi encourages starting small to benefit from compound growth [3][4]. - The regret of not investing in cryptocurrencies like Bitcoin is highlighted, with Sethi warning against speculation and emphasizing the importance of a diversified portfolio [6][7]. Group 2: Housing Decisions - Many individuals regret purchasing homes that are too large, leading to financial strain; Sethi advises potential homeowners to assess affordability, including additional costs like taxes and maintenance [4][5]. - The average monthly housing costs can reach $3,500, which constitutes 49% of the median gross monthly income for first-time homeowners aged 25 to 44 in America, indicating a significant financial burden [5].