As many have suggested in the comments, it might be hard, if not impossible, to find an investment that gives positive returns with certainty. However, you might consider a metric such as
$$R=\underset{s\in [0,T]}{\min}r_{0,s}$$
where $r_{0,s}$ is the portfolio return between the initial investment point $0$ and $s$. $R$ gives the highest share of seed money lost between $0$ and $T$. Then you could try to find an investment that with high probability has a good $R$.
You can affect $R$ through dynamic trading. As in this paper, the optimal strategy seems to increase risk after positive returns. So you would start investing in the risk-free asset and gradually increase risk after that. This way it might in theory be possible to guarantee positive returns for initial investment, though not sure how well this works in practice.