I'm surprised Monarch was missing transactions. I use it too and think it's a great way to track spending over time. I don't budget, but I do have a spending plan. Although I hate to break it to you...but when it comes to your withdrawal rate in retirement, taxes, operational expenses, construction of a second home, and capital improvements do all count as "spending!"
I do think you would be served to set up an ongoing monthly "paycheck" from your brokerage so you're not constantly having to decide how much to transfer and debate what kind of spending is too much. Inevitably that will be based on emotions not math and cause internal (and marital) conflict.
For the record though, most people feel cash crunched when they are buying or building a house no matter how rich they are. That's a tough thing to do while navigating the switch from accumulation to spending your wealth. Hang in there!
PS - I grew up skiing in Crested Butte every year with my family. Such wonderful memories!!
I was very surprised Monarch was missing transactions. It was actually Plaid, the “glue” used by Monarch and other apps to connect to your bank feed. Plaid was missing certain Chase and Ally transactions, no matter if I connected my bank to Monarch or Digits (a business grade accounting SaaS).
That’s why I’m now a big believer in reconciliation. Seemed like overkill at first but it’s so reassuring now and only takes a few moments to do using AI built-in to the software I’m now using.
Haha yes, all of it counts as total spending… but the home might become primary and our existing home sold, so there’s some complexity with accounting treatment in terms of modeling SWR. It would truly be a one time large expense, the construction, so I’m basically subtracting that amount from our net worth and using the remainder to calculate a long term SWR ballpark.
I like your idea of a brokerage paycheck. Tbh I think we need to get a little better understanding of our spending, and these “one time” post exit things, otherwise the paycheck is unlikely to cover our nut each month!
Reassuring your clients also felt cash crunched when building. It is a lot all at once but with young kids and the new geographic flexibility feels like we need (want) to take advantage of the magic window!
That’s crazy you grew up skiing CB! If we ever build that house would be insane if you stopped by someday. Now I have to ask, are you from Texas ;)
Actually my fam lived in Louisiana and later Alabama growing up. I live in Dallas now but I swear I’m not like all the other annoying Texans taking over Colorado…lol.
Yeah what you’re running into is the exact reason I discourage wealthy folks from worrying too much about the SWR; trying to nail it down becomes nearly impossible for many. Turns out there are large one time expenses pretty much every year! And periodic windfalls too. “Income” and “expense” become sort of nebulous concepts, which can keep spreadsheet junkies like us tied to their screens moving numbers around...
Weirdly this is the part so many of us miss! Understanding my spending has become super important to me, because a work optional life doesn’t work unless the amount I spend matches the amount I can safely withdraw. I can’t answer questions like “can we afford that?” Without that broader context. The work to build a historical understanding was difficult and took many days, but the ongoing maintenance (sorting into correct categories etc, running down what Venmo or Apple Pay transactions actually were) is just a monthly task now. I do have a budget but I try and think of it like I think of the word diet. Not as a plan to spend less or a plan to eat less, but as a plan to spend intentionally and to eat health, delicious nourishing food. It isn’t about restricting, it’s about making intentional choices and making sure they align with my values!
Yeah I agree with the budget not being about restricting, but allocating intentionally. My experience so far during setup mirrors yours - a lot of work to get the historical data and baseline, much easier (albeit still some work) to keep it updated.
Thanks for the comment! Great to meet you Jessica. Your business and writing is interesting. Following.
Tell me about it. I created a Codex (ChatGPT) skill to figure out and code the Amazon transactions from two separate Amazon accounts into our budgeting software. It works really well but is a bit fragile still. It helps to have the Amazon credit card because it puts the Amazon order ID next to every charge on the statement. That’s the lookup key.
In the budgeting system I use with clients I ask them to track spending for two months and beside each line item I have them answer the question “is this worth it?”
I think this takes away the stigma of spending on things that truly add value to your life as much as it helps you note where you’re getting the least ROI for your dollars.
Many of my higher income clients are surprised that by tracking they don’t end up spending any less but do feel more aligned and comfortable with their decisions.
Budgeting really doesn’t have to feel restricting! And it really does feel good to feel in control of monthly spending. I know I can take four months off as a self-employed person for maternity leave because I know how much my life costs month to month.
If you’re ever curious about working together I’d be happy to chat (after I’m back from said maternity leave in Feb!)
Enjoy your leave. I love the “is this worth it?” question. Monarch-style personal finance apps should support that exact data entry field!
Tbh I’ve been getting a lot better at asking myself this question but as a complete household decision making system we have a ways to go. Let’s stay in touch... following!
Definitely start with an app that doesn’t miss transactions! And auto-categorizing each line item is the way to go to avoid having to bin everything manually (it has the added bonus of making you bin unusual transactions, which are the most likely ones to need a closer look).
I’m not hyper-focused on returns on our cash, so the HYSA dumps into the checking automatically and I just see the HYSA balance in the spreadsheet. Until COVID those transfers were limited to six per month, then 10, and now there is no limit so the transfer from savings to checking happens automatically.
Sounds like you have a system that works well for you. I also put a hysa in front of my checking account for a while. Fairly elegant. I moved to keeping cash in my brokerage account for a few reasons but it’s probably not broadly applicable:
1. In a brokerage, I can buy government bond ETFs like SGOV and their interest payments are state tax free. Plus the interest rate is consistently a little higher than even the best high yield savings accounts.
2. The cash also functions as margin collateral. I run a portfolio margin setup using interactive brokers. Will write more about this later.
We have looked into this with FREC but haven’t pulled the trigger. Our windfall event (an IPO, in our case) was very recent, so we’re overwhelmed with all the new divisions but already had systems in place for budget because of some very lean years leading up to the IPO.
I’d love to hear more. The Long Angle posts talking about margin intrigue me: margin for what? I don’t need margin now that I’m FIREd, right?
So glad we found each other. Substack must be doing something right, because if you’re recently FI from an IPO, you’re exactly who I’m trying to reach!
We probably have a lot in common. I also had many “leaner” years leading up to my liquidity event.
I’ve heard of Long Angle but haven’t joined yet. Have you found it valuable?
In terms of margin, it’s really just a fancy word for a loan. But even if you don’t want to borrow in the traditional sense, there can be some advantages to setting up your portfolio in a way that gives you built-in access to a very large, extremely low-cost line of credit.
I like it mostly because it provides flexibility and insurance.
For example, I might build a new home, and I could draw on it instead of taking out a significantly more expensive construction loan.
I can also draw on it temporarily to cover living expenses instead of selling securities. This can help with short-term liquidity or tax-related timing gaps, anywhere from a month to a year. Or if the market is temporarily down, I don’t necessarily have to sell into it. During the sharp drop in April 2025, for example, I just drew on my portfolio line of credit instead of selling my S&P 500 index fund that month.
There are some other interesting uses related to portfolio architecture too, like intentionally running a long-term cash deficit as part of a risk parity-style portfolio. Look up Ray Dalio’s “cash is trash” idea if you want to go down that rabbit hole.
Not saying you should do any of this, of course. But it’s an interesting option you may qualify for given your likely HNW post-IPO situation.
I’ll absolutely write more about it. I spent a long time learning and experimenting with this stuff, and there really isn’t much written for the self-directed, DIY, post-exit or post-IPO crowd.
You’d love Long Angle, and the free membership has been good enough for me. There are lots of private equity opportunities and people discussing investment options. The founders of many fintech companies are there, which means I get a personal answer when I have questions about long-short direct investing or tax planning, for instance.
There is a subgroup for entrepreneurs (on the free side; I don’t have access to the paid side). I use the subgroup on charitable giving. Plus you can go to local meet-ups. All this to say you should definitely join for free, and since you’re further into your journey you may enjoy the paid version because of all the things that provides: a small Trusted Circle, discounts on services, and an invite to the annual retreat.
I have a spreadsheet. A line for each month. First column I enter what we spent using the credit card (not the payment but what the credit card app tells me I spent in a given month). Second is what we spent using cash or ACH or check. Third column for what we gave the kids.
Then I do an average and it needs to average out to equal or less than the amount per month we have on auto withdrawal.
I don’t have anything looking at my bank accounts. Call me paranoid.
If you like to ‘get your fingers dirty’ (metaphorically) then you may prefer Tiller over Monarch… (we use both) because Tiller puts it in Sheets or Excel (you choose) and naturally you can do whatever you want with the transaction data at that point. Cashflow analysis, simulations, whatever you need… and with Claude or CoPilot doing the hard part of coming up with the simulations… anyway, it may not be how you want to spend your time.
I would also agree with Elizabeth regarding Monarch missing transactions. Tiller uses two sources for transactions, not just plaid.
I tried Tiller for about a year pre-exit. I liked the flexibility of a spreadsheet based personal finance tool in theory, but found it still lacked two key features:
1. Reconciliation
2. Double entry ledger
I also found the lack of a traditional database made it tough in years 2,3,4 when you started to have more transaction data and many years of tinkering, rules, etc in a single spreadsheet.
But I understand why it might be a great solution for a lot of people.
Yep, it's not double entry. For better or for worse :)
But the other disadvantages have solutions I believe, through evolution of the product. Cool that you tried it... and that community keeps expanding (I know of others with your use case that are deep into it). Moving on...
If you haven't used Boldin you may want to dive into that (deep) pool. It is literally the monte carlo simulation capability bolted to a database of your personal finance data, and you can run all kinds of simulations. It keeps evolving, and the capabilities are amazing. It can also suck up a fair amount of your attention with the subtle issues that scale over years/decades, hotly debated in Reddit by similar post-retirement (and post-exit) types.
Thanks for the Boldin suggestion. I’ll check it out. I like Monte Carlo and have used it a lot through Portfolio Visualizer but you gotta know its limits. Otherwise as you said, Reddit rabbit holes in your future.
Appreciate your thoughtful comments.
Re: double entry, I thought it was overkill for the longest time but with some of these new AI ledgers it’s not bad to maintain.
Personally I find all the workarounds with other personal finance tools harder than just “doing it right” with a true double entry ledger. More on that soon.
I'm surprised Monarch was missing transactions. I use it too and think it's a great way to track spending over time. I don't budget, but I do have a spending plan. Although I hate to break it to you...but when it comes to your withdrawal rate in retirement, taxes, operational expenses, construction of a second home, and capital improvements do all count as "spending!"
I do think you would be served to set up an ongoing monthly "paycheck" from your brokerage so you're not constantly having to decide how much to transfer and debate what kind of spending is too much. Inevitably that will be based on emotions not math and cause internal (and marital) conflict.
For the record though, most people feel cash crunched when they are buying or building a house no matter how rich they are. That's a tough thing to do while navigating the switch from accumulation to spending your wealth. Hang in there!
PS - I grew up skiing in Crested Butte every year with my family. Such wonderful memories!!
I was very surprised Monarch was missing transactions. It was actually Plaid, the “glue” used by Monarch and other apps to connect to your bank feed. Plaid was missing certain Chase and Ally transactions, no matter if I connected my bank to Monarch or Digits (a business grade accounting SaaS).
That’s why I’m now a big believer in reconciliation. Seemed like overkill at first but it’s so reassuring now and only takes a few moments to do using AI built-in to the software I’m now using.
Haha yes, all of it counts as total spending… but the home might become primary and our existing home sold, so there’s some complexity with accounting treatment in terms of modeling SWR. It would truly be a one time large expense, the construction, so I’m basically subtracting that amount from our net worth and using the remainder to calculate a long term SWR ballpark.
I like your idea of a brokerage paycheck. Tbh I think we need to get a little better understanding of our spending, and these “one time” post exit things, otherwise the paycheck is unlikely to cover our nut each month!
Reassuring your clients also felt cash crunched when building. It is a lot all at once but with young kids and the new geographic flexibility feels like we need (want) to take advantage of the magic window!
That’s crazy you grew up skiing CB! If we ever build that house would be insane if you stopped by someday. Now I have to ask, are you from Texas ;)
Actually my fam lived in Louisiana and later Alabama growing up. I live in Dallas now but I swear I’m not like all the other annoying Texans taking over Colorado…lol.
Yeah what you’re running into is the exact reason I discourage wealthy folks from worrying too much about the SWR; trying to nail it down becomes nearly impossible for many. Turns out there are large one time expenses pretty much every year! And periodic windfalls too. “Income” and “expense” become sort of nebulous concepts, which can keep spreadsheet junkies like us tied to their screens moving numbers around...
Weirdly this is the part so many of us miss! Understanding my spending has become super important to me, because a work optional life doesn’t work unless the amount I spend matches the amount I can safely withdraw. I can’t answer questions like “can we afford that?” Without that broader context. The work to build a historical understanding was difficult and took many days, but the ongoing maintenance (sorting into correct categories etc, running down what Venmo or Apple Pay transactions actually were) is just a monthly task now. I do have a budget but I try and think of it like I think of the word diet. Not as a plan to spend less or a plan to eat less, but as a plan to spend intentionally and to eat health, delicious nourishing food. It isn’t about restricting, it’s about making intentional choices and making sure they align with my values!
Yeah I agree with the budget not being about restricting, but allocating intentionally. My experience so far during setup mirrors yours - a lot of work to get the historical data and baseline, much easier (albeit still some work) to keep it updated.
Thanks for the comment! Great to meet you Jessica. Your business and writing is interesting. Following.
The worst part is trying to find out whose Amazon purchase are whose 🫠 glad to be connected!
Tell me about it. I created a Codex (ChatGPT) skill to figure out and code the Amazon transactions from two separate Amazon accounts into our budgeting software. It works really well but is a bit fragile still. It helps to have the Amazon credit card because it puts the Amazon order ID next to every charge on the statement. That’s the lookup key.
In the budgeting system I use with clients I ask them to track spending for two months and beside each line item I have them answer the question “is this worth it?”
I think this takes away the stigma of spending on things that truly add value to your life as much as it helps you note where you’re getting the least ROI for your dollars.
Many of my higher income clients are surprised that by tracking they don’t end up spending any less but do feel more aligned and comfortable with their decisions.
Budgeting really doesn’t have to feel restricting! And it really does feel good to feel in control of monthly spending. I know I can take four months off as a self-employed person for maternity leave because I know how much my life costs month to month.
If you’re ever curious about working together I’d be happy to chat (after I’m back from said maternity leave in Feb!)
Enjoy your leave. I love the “is this worth it?” question. Monarch-style personal finance apps should support that exact data entry field!
Tbh I’ve been getting a lot better at asking myself this question but as a complete household decision making system we have a ways to go. Let’s stay in touch... following!
That’s great to hear! And thank you so much!
Definitely start with an app that doesn’t miss transactions! And auto-categorizing each line item is the way to go to avoid having to bin everything manually (it has the added bonus of making you bin unusual transactions, which are the most likely ones to need a closer look).
I’m not hyper-focused on returns on our cash, so the HYSA dumps into the checking automatically and I just see the HYSA balance in the spreadsheet. Until COVID those transfers were limited to six per month, then 10, and now there is no limit so the transfer from savings to checking happens automatically.
Sounds like you have a system that works well for you. I also put a hysa in front of my checking account for a while. Fairly elegant. I moved to keeping cash in my brokerage account for a few reasons but it’s probably not broadly applicable:
1. In a brokerage, I can buy government bond ETFs like SGOV and their interest payments are state tax free. Plus the interest rate is consistently a little higher than even the best high yield savings accounts.
2. The cash also functions as margin collateral. I run a portfolio margin setup using interactive brokers. Will write more about this later.
We have looked into this with FREC but haven’t pulled the trigger. Our windfall event (an IPO, in our case) was very recent, so we’re overwhelmed with all the new divisions but already had systems in place for budget because of some very lean years leading up to the IPO.
I’d love to hear more. The Long Angle posts talking about margin intrigue me: margin for what? I don’t need margin now that I’m FIREd, right?
So glad we found each other. Substack must be doing something right, because if you’re recently FI from an IPO, you’re exactly who I’m trying to reach!
We probably have a lot in common. I also had many “leaner” years leading up to my liquidity event.
I’ve heard of Long Angle but haven’t joined yet. Have you found it valuable?
In terms of margin, it’s really just a fancy word for a loan. But even if you don’t want to borrow in the traditional sense, there can be some advantages to setting up your portfolio in a way that gives you built-in access to a very large, extremely low-cost line of credit.
I like it mostly because it provides flexibility and insurance.
For example, I might build a new home, and I could draw on it instead of taking out a significantly more expensive construction loan.
I can also draw on it temporarily to cover living expenses instead of selling securities. This can help with short-term liquidity or tax-related timing gaps, anywhere from a month to a year. Or if the market is temporarily down, I don’t necessarily have to sell into it. During the sharp drop in April 2025, for example, I just drew on my portfolio line of credit instead of selling my S&P 500 index fund that month.
There are some other interesting uses related to portfolio architecture too, like intentionally running a long-term cash deficit as part of a risk parity-style portfolio. Look up Ray Dalio’s “cash is trash” idea if you want to go down that rabbit hole.
Not saying you should do any of this, of course. But it’s an interesting option you may qualify for given your likely HNW post-IPO situation.
I’ll absolutely write more about it. I spent a long time learning and experimenting with this stuff, and there really isn’t much written for the self-directed, DIY, post-exit or post-IPO crowd.
So glad to have you here. DM or email me anytime.
You’d love Long Angle, and the free membership has been good enough for me. There are lots of private equity opportunities and people discussing investment options. The founders of many fintech companies are there, which means I get a personal answer when I have questions about long-short direct investing or tax planning, for instance.
There is a subgroup for entrepreneurs (on the free side; I don’t have access to the paid side). I use the subgroup on charitable giving. Plus you can go to local meet-ups. All this to say you should definitely join for free, and since you’re further into your journey you may enjoy the paid version because of all the things that provides: a small Trusted Circle, discounts on services, and an invite to the annual retreat.
How sad for you…a full time nanny…sure you are struggling just like the average American.
I have a spreadsheet. A line for each month. First column I enter what we spent using the credit card (not the payment but what the credit card app tells me I spent in a given month). Second is what we spent using cash or ACH or check. Third column for what we gave the kids.
Then I do an average and it needs to average out to equal or less than the amount per month we have on auto withdrawal.
I don’t have anything looking at my bank accounts. Call me paranoid.
You’ve found a simple, elegant solution that works. All that matters is you’re doing it. Good for you.
If you like to ‘get your fingers dirty’ (metaphorically) then you may prefer Tiller over Monarch… (we use both) because Tiller puts it in Sheets or Excel (you choose) and naturally you can do whatever you want with the transaction data at that point. Cashflow analysis, simulations, whatever you need… and with Claude or CoPilot doing the hard part of coming up with the simulations… anyway, it may not be how you want to spend your time.
I would also agree with Elizabeth regarding Monarch missing transactions. Tiller uses two sources for transactions, not just plaid.
Agree with the virtual paycheck concept.
I tried Tiller for about a year pre-exit. I liked the flexibility of a spreadsheet based personal finance tool in theory, but found it still lacked two key features:
1. Reconciliation
2. Double entry ledger
I also found the lack of a traditional database made it tough in years 2,3,4 when you started to have more transaction data and many years of tinkering, rules, etc in a single spreadsheet.
But I understand why it might be a great solution for a lot of people.
Yep, it's not double entry. For better or for worse :)
But the other disadvantages have solutions I believe, through evolution of the product. Cool that you tried it... and that community keeps expanding (I know of others with your use case that are deep into it). Moving on...
If you haven't used Boldin you may want to dive into that (deep) pool. It is literally the monte carlo simulation capability bolted to a database of your personal finance data, and you can run all kinds of simulations. It keeps evolving, and the capabilities are amazing. It can also suck up a fair amount of your attention with the subtle issues that scale over years/decades, hotly debated in Reddit by similar post-retirement (and post-exit) types.
Thanks for the Boldin suggestion. I’ll check it out. I like Monte Carlo and have used it a lot through Portfolio Visualizer but you gotta know its limits. Otherwise as you said, Reddit rabbit holes in your future.
Appreciate your thoughtful comments.
Re: double entry, I thought it was overkill for the longest time but with some of these new AI ledgers it’s not bad to maintain.
Personally I find all the workarounds with other personal finance tools harder than just “doing it right” with a true double entry ledger. More on that soon.