I really don't have more than basic education in statistics, but to me it looks like a slight but constant upward trend until 100 investors contacted and after that we simply don't have enough data. If you think about what the diagram talks about getting a constant upward line or even more likely a square root shaped line is very likely. Getting a bell curve is unlikely, just from thinking about the topic. What should happen that contacting more than X investors would result in less meetings?
In the second diagram removing the two dots at $4.5m and the two dots above 200 investors met leaves us with 196 data points that show a fairly equal spread and that the amount of investors contacted might not influence that much how much money you get in the end. That's also good because it's expected to find that company evaluation depends on company value (customers, market, team, etc) and not on how many investors you contact.
You make the data more conclusive by removing data points that have a big impact on your results without the backup of other data points. That's what handling outliers is.
I would agree that cutting-off curve fitting at 100-150 investors would look prettier; the thing to do in that case would be either to not attempt to fit a curve and just show the data, or alternately to fit only the earlier part (so the red line stops half-way across the x-axis), but show all the data.
The only reason for doing a curve fit on this kind of data is to show that the data fit some prior model, showing that the model is likely correct, or to show where some statistical value lies.
Note that if the sample is large enough and selected uniformly, the need for the analysis on the entire population is unnecessary.
In this case, it does't apply, though.
The sample isn't particularly large, and we don't know the extent of possible selection biases. For example one obvious bias is that the sample is restricted to data sent through Docsend, thus likely does not represent a uniform sampling of all pitches.
In any case, there is no prior reason to exclude outliers; any large enough representative sampling of a Gaussian distribution would include "outliers".
The data presented is a sample, the "true" distribution might be different from what is shown, and if you start 'cleaning" the data based on subjective judgements, you might never discover the true range.