Getting started: a few questions

Hi everyone. I have high hopes for this app! I am from Portland Oregon where I run a small theater company. I write and perform solo shows (as well as run workshops and events).
I would like to get to a place where i understand money! I have been afraid of tracking my income for a long time (because every time I do, the situation seems dire. If i just stick my head in the sand, I don’t have to deal with it).
I feel like i might have an undiagnosed learning disability when it comes to money. I have a really hard time understanding spreadsheets and accounting. I just kind of go blank when talking about the concepts of bookkeeping (I tried taking a class on Quickbooks and the double accounting thing just fried my brain).
I put a post on FB a while ago asking for suggestions for bookkeeping and financial tracking apps. I tried a few (like Rocket Money) but Tiller was the one that felt the friendliest and most accessible.
I am determined to learn how to use this thing!
My skill level with spreadsheets is NIL.
I have never used a tool that helped me understand money. (I’ve tried, just with no success). I used Turbo Tax to do my taxes (and that often ends up in tears).
I spent 25 years in the restaurant industry and dealt with cash. I never learned budgeting or tracking (but it’s never too late!)
I want to understand where my money goes (spending), how much I’m making (income) and start paying down debt. Eventually i would like to attempt a budget.

So, i have started my tiller journey. I have set up my accounts. I have imported the transactions for the last 4(?) months (since Dec. 2023).

Here are a few of my questions -

How do I import all of 2023 so I can itemize transactions and figure out my deductable expenses?

PAYPAL- sometimes Paypal uses the money IN the paypal account, and sometimes it transfers the money from my bank account into paypal to pay for an item. Which makes for two entries - a debit and a transfer. I set up an autocat for paypal transfers, but then I realized they differ, depending on where the money comes from. Is there a way to autocat a certain kind of paypal transaction?

COLLECTING MONEY - I have been collecting money in Paypal for a birthday gift for a friend (as a fundraiser). When people donate, it shows up twice - both as a debit and a credit, and I’m not sure why. I don’t want to include it as income, so I am not sure how to catagorize it (I suspect I have to make it income and then hide it?)

SHARED EXPENSES - sometimes I pay the rent and then my housemates pay me, and sometimes I pay them. How to i catagorize their payments to me? Income (and hidden?)

UNKNOWN EXPENSES - I have transactions i can’t find the origin for. Generally these show up in my bank statement as a paypal charge (with no other info). But I can’t find the transaction in paypal, just in my bank statement.

CATAGORIZING MULTIPLE TRANSACTIONS AT ONCE - I sometimes sell tickets through paypal. Which is a LOT of transactions. Is there a way to highlight a group and make them all one catagory? (even though they are different buyers)

I would LOVE to hire a knowledgable person who could walk me through all of this and I could ask my very basic questions and not feel like an idiot. I saw that there is a person in this community who offers this service, but I think for me it’s overkill (they start at 4 sessions for $1600).

I looked at fiverr and Upwork for people who have tiller listed as a skill. I found a woman in Pakistan who I am considering hiring, thought I am not sure how it will work. I would like to have a synchronous conversation, not just send someone my spreadsheets and have them try and figure things out.

Sorry for the extrememly long into - I am doing my best to commit to this process, and apparently had a lot to say. I am going to go watch the intro webinar, which i just discovered. Hope every has an awesome weekend!

Hi @EleanorO and welcome,

You may get more answers if you post each of your questions as a separate topic.

But I’ll take a stab at the first question, which was

How do I import all of 2023 so I can itemize transactions and figure out my deductable expenses?

Try logging in to the website for each of your accounts. Look for an option to download past activity. Your goal is to end up with a file, ending in .csv, in your downloads folder for each of your accounts. Once you have those files, follow the instructions here: How to Manually Import Your Bank Data | Tiller Help Center

If you get stuck at any point, start a new topic. There are plenty of folks here who can help.

thanks so much! I appreciate that tip and link for downloading and importing csv files.

I am a little afraid to post a question because I am worried that it’s too basic and someone has already asked it or it’s been answered a million times but i don’t know how to search for it.

I think you’ll find people are happy to help.

I’ve found that I get the best results when I search for keywords in the box on the main Community page:

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Yes, this seems to be a very helpful community. The challenge for me is sometimes I don’t know how to articulate the problem, so I’m not sure what keywords to use. For example, in the “how to split the rent” question - i want’ sure i should look up expense sharing, splitting, how to catagorize repayments, etc.

UPDATE - I did hire someone to help me off of Upwork. A woman in Pakistan! So excited to have help in real time. I’ll keep you posted as to how it turns out.

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Do you need to import last years data? If your afraid of getting overwhelmed , starting from scratch and looking at only a few transactions may be the best.

As you learn more you can add more accounts and if you want add the historical data

Also you may want to look at YouTube for Google sheets videos. As having some basic spreadsheet skills is helpful.

Good luck and remember the community is always here too.

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