Wingman Doesn't Accept Trading History

Here's why! Hint: starting today is a way better experience (for you, and us).

You may want to upload a lot of history to get performance analysis right off the bat.

I totally get the value of that!

But here's why we chose to only accept trading history going forward.

1. Arbitrary starting points make it hard to get your current positions up to speed When you upload trading history, you have to choose an arbitrary starting point, such as "YTD". And positions in Wingman are only built up from opening orders. Often, this can make things very messy.

You can be missing opening orders that were responsible for positions you still have open (and therefore would never get imported, and no position would get created in Wingman). Or you only get a fraction of the position. Then you'd have to reconcile all the positions and start manually adjusting things by tracing back what your cost basis was etc.

This is why we take the Positions CSV approach when creating the account — it snapshots your current holdings and associated cost basis, which guarantees your current holdings are up to speed with minimal review/reconciliation. This also means transactions going forward will nicely match up with existing positions. Read on...

2. Uploading a lot of history is overwhelming and prone to errors If you wanted to go all the way back to your account opening, it would be so much history to comb through, that it would lead to an overwhelming reconciling/review experience that is error-prone. With hundreds or thousands of transactions, you're looking at dozens of possible oddities in the data from the brokerage that could be confusing, may require customer support (a lot for us to handle being such a tiny team, and a burden for you), or require deleting certain data, which would skew your analysis anyway.

3. History would duplicate the data that is baked into your position snapshot in the system When you added the account, you imported your current positions, which is a direct reflection of your trading history in a cumulative sense. Uploading history would duplicate the information already there and "overrun" it. So, it would require deleting all of that position data, or uploading it into a separate account, then comparing/reconciling the two, and merging them accounts together. Not a pleasant experience.

A positive outlook on starting fresh

The bright side to this is that you get to start with a blank canvas. You've signed up for Wingman and committed to track and improve your trading in a sustainable way. This is a great opportunity to only record your performance under this new approach, and to be very intentional about using custom tagging for personal bucketing, which will make your Analysis reports higher quality and more relevant to your present-day self as a trader.

This is like adding traffic analytics to a website — there's no way get the data historically before you added the tracking to your site, but you can measure it well going forward.

If not being able to upload history is a dealbreaker for you, I'm really sorry Wingman isn't a good fit! This is a tradeoff we feel makes sense overall, but definitely is a sacrifice to some. Having said that, there's no better time to start building up the trading activity/history than now! You have 30 days in a free trial to figure out whether Wingman can work for you going forward — we know it takes time to get through a trading cycle and give the software a fair try. Hope you come back tomorrow for your next transaction import!