Somebody found out that
$$2^{N-1} + 2^{N-2} + \dots + 2^0 = \sum_{i=0}^{N-1} 2^i = 2^N - 1.$$
Apparently, the sum can also be expressed as
$$ \sum_{i=0}^{N-1} 2^i = \sum_{i=0}^{N-1} (a_i + \bar{a}_i) \cdot 2^i,$$
where $a_i$ is either $0$ or $1$ and
$$\bar{a}_i = \begin{cases}1 & \text{if } & a_i = 0 \\ 0 & \text{otherwise.} \end{cases}$$
We will denote $a_i$ as a binary coefficient and $\bar{a}_i$ as its complement.
Introducing $w = \sum_{i=0}^{N-1} a_i 2^i$ as a natural number in the range $0 \dots 2^N-1$, the first equation can be rewritten as
$$w + \bar{w} = 2^N - 1,$$
where $\bar{w} = \sum_{i=0}^{N-1} \bar{a}_i2^i$ denotes, again, $w$'s complement.
The above equation is equivalent to
$$-w = \underbrace{\bar{w} + 1}_{\text{two's complement}} - 2^N.$$
From my understanding, what happens next is a convention, namely agree upon that the $N$-th bit of a negative number is set to $1$, where the remaining bits are encoded as the two's complement of its absolute value.
If you are to subtract $w$ from another natural number $v$ in the range $0 \dots 2^N-1$, the two's complement allows you to express this as an addition:
$$v - w = v + (-w) = v + \underbrace{1 + \bar{w}}_{\text{two's complement}} - 2^N.$$
In case $v > w$, we have that
$$v + (-w) = (w + \epsilon) + (-w) = \epsilon + \underbrace{1 + w + \bar{w}}_{2^N} \underbrace{- 2^N}_{N\text{-th bit}} = \epsilon > 0, $$
and the negative bit vanishes due to overflow.
In case $v < w$, we have that
$$v + (-w) = (w - \epsilon) + (-w) = \underbrace{\underbrace{1 + w + \bar{w}}_{2^N} - \epsilon}_{<2^N} - 2^N = -\epsilon < 0, $$
and the negative bit remains.