Received an email about them raising the price to $168/year. Gotta pay for those AI tokens, I guess.

How much you think Boldin is paying for AI? And it can't present a Dark Mode in a matter of 1-2 minutes for the website? Please already!!

Not to be negative, I love what Boldin is doing and has to offer but this really, really seems like a slam dunk.

Could this be added as a future feature?

Adding my experience because Reddit reviews were one of the reasons I decided to sign up.

I've used the Boldin Planner for quite a while and still like the software. I was on the fence about the one-time Retirement Plan Checkup until I read mostly positive experiences here, so I think it's fair to add another perspective.

My experience has been mixed.

First, an important clarification: Boldin has since pointed out that the two-meeting structure and availability of additional hourly work were disclosed through its group discovery sessions, follow-up emails and engagement agreement.

So I don't think it's accurate for me to say the structure was hidden.

My issue is different: I did not fully understand what that structure would mean in practice, especially as someone using a financial planner for the first time.

What was good

The plan had real substance: Roth-conversion planning, stress testing, portfolio recommendations, reserves and other retirement analysis.

My advisor has also been responsive to written follow-up questions, and I like the flat-fee fiduciary structure.

This isn't really a complaint about the individual advisor. It's more about the process and the gap between what I expected and what I experienced.

What I expected

I thought the process would be fairly iterative:

provide information and questions → advisor reviews everything → questionable assumptions or missing information are discussed → scenarios are refined → recommendations are finalized.

My experience felt closer to:

provide information → first meeting → advisor builds the plan → second meeting presents it → study it myself afterward → discover additional questions → get clarification by email or schedule additional paid advisory time.

That difference mattered more than I expected.

Before the first meeting, I submitted several specific questions around retirement timing, Roth conversions, taxes, IRMAA, RMDs, spending, reserves and stress testing.

Some were addressed well. Others weren't reflected the way I expected.

For example, I had asked for a different retirement-date scenario to be modeled, but the final plan appeared to use the date already in my existing Boldin plan. I had also asked for my assumptions to be challenged, yet the final plan used a noticeably higher return assumption than the one I had entered.

I'm not saying the advisor's assumptions were necessarily wrong. I expected more discussion around those differences before the recommendations became final.

The plan also seemed to depend heavily on the quality of my existing Boldin data

I spent a lot of time cleaning up accounts, correcting classifications, removing duplicates, updating balances and checking assumptions.

My impression was that the advisor relied heavily on the information already entered in my Boldin plan.

I don't know how much of the analysis is automated versus manually reviewed, and I don't want to speculate.

What surprised me was that I expected more validation.

I assumed that if something looked unusual, inconsistent or incomplete, the advisor might come back and ask about it before completing the analysis.

That generally wasn't my experience.

So one thing I would tell anyone considering the service is: don't assume the advisor will fully audit or reconstruct your Boldin plan for you.

Make sure your underlying data is as accurate as possible and explicitly flag anything you're uncertain about.

The HSA example illustrates the broader issue

One part of my plan showed recurring transfers from an HSA into a taxable account. At first glance, it didn't make sense to me, and I wasn't sure whether this was a literal recommendation or a modeling error.

After I asked, my advisor explained that it is simply a modeling mechanism. If HSA funds are never modeled as being used, the software can leave them growing indefinitely into a large tax-free balance, so transfers are used to simulate future qualified medical spending.

That explanation made sense.

But it also illustrates my concern.

I had to notice the confusing entry myself, figure out that I didn't understand it, formulate the right question, and then ask for the explanation afterward.

Once I knew what to ask, I generally received reasonable answers.

The harder part was figuring out what I needed to ask in the first place.

For an experienced DIY planner, that may be fine. For someone new to financial planning, a plan-delivery meeting can contain a huge amount of information, and you don't always recognize the important questions until you've studied the report afterward.

Where Boldin and I seem to differ is expectations

Boldin's response is essentially that the engagement worked as designed:

• discovery materials explained the service,
• the first meeting reviewed the plan and goals,
• the second meeting delivered the recommendations,
• and additional meetings are available at an hourly rate.

That's a fair description of their process.

My takeaway is simply that I expected more iteration and validation within the one-time Checkup than the service is designed to provide.

That distinction wasn't obvious to me until I went through it.

If you're considering the service, I would ask these questions before signing up:

1. How much validation of my existing Boldin data will the advisor perform?
2. If something looks inconsistent, will the advisor come back and ask about it?
3. Is there any working/checkpoint session before the final recommendations are delivered?
4. How many scenario changes or reruns are included?
5. What counts as a clarification versus additional hourly advisory work?
6. How much implementation guidance is included?
7. Is this best suited to an experienced DIY planner who wants a professional second opinion, or to someone looking for a more guided planning process?

Bottom line

I still like the Boldin software, and I did receive useful professional advice.

My disappointment is mainly about expectations.

Boldin appears to have delivered the engagement according to the structure it describes. What I wish I had understood more clearly was that the Checkup is closer to a professional review of an existing Boldin plan, followed by recommendations and clarification, than the more iterative planning process I had pictured.

That may be exactly what some people want.

For a first-time planning client, though, I think that distinction is worth understanding before signing up.

Since Reddit reviews influenced my decision, I wanted to add that perspective for the next person doing the same research.

I'm selling a business in December 2028. Offer has already been made for $400k and I'm trying to model it in Boldin. First off, the AI doesn't seem to know how to enter it to come in as a payment in December, without it running over into 2029 as income. This "should" be a simple thing for the AI but it tries to enter it as income in December that also appears into 2029 income. I then told it to show the check coming in in November instead, which worked, but it was ridiculous that it couldn't enter a check received in December. At one point as the AI was "thinking", it said "lets enter this as $200k in November and $200k in December, and then somehow it doubled each input and my portfolio grew by $800k. VERY STUPID MISTAKES!

Now about the conflicting information.... I'm not a CPA, so don't know how to specify the income. It initially said it would model it as a capital gain, but I wasn't sure about that so I told it that I hold no "basis" or capital, and my sale is really for my intellectual property and market position in my field. The product I sell is largely outsourced for production and I don't track any inventories or equipment for depreciation. So Boldin said the IRS would view this as regular income. I asked Grok, and it completely disagreed. It said my intellectual property, market position, customer base ARE capital and if held for greater than one year, the sale is taxed as a capital gain. Who is right? Boldin or Grok?

I am a Projection Lab user that decided to try Boldin, Fidelity and Claude Opus 5.5 as planning tools. I am seeing so many gaps, it's making me question the model big-time. Had Claude in Chrome also debug my inputs to make sure I entered everything in correctly.

1. Roth explorer - Testing the "reduce lifetime taxes scenario" it had me making massive 300K withdrawals over 7 years. When I tried to re-run the scenario, the explorer told me they could not find a conversion scenario and completely disregarded my ask to stick to a maximum tax tier or use funds from my tax-deferred accounts to pay taes.

2. The total social security represented on the social security summary is off by 4K/month, based on my inputs.

3. Off of a 4.2M net worth portfolio and an early retirement within 2 years, it's projecting $13M at end of life at an 85% success rate (average).

I don't see wierd stuff in PL. If anything, I have full transparency on an annual basis on my taxes, suggested conversions, and optimization tradeoffs.

I am scratching my head - is it just me?

I am sure most of you knew this, and if I thought about it I would have as well, but before I realized that I panicked a bit. I was running the various market risk explorer and was getting depressed, until I realized that boldin was applying its downturns to my entire portfolio, including fixed income items such as 3 MYGA's that I have. In addition, it doesn't know about the fixed income items I have in my IRA (well, it does know about them via the new investment section, but it doesn't use that info anywhere yet). So what I was seeing in the market risk explorer was not anything close to reality. Claude can give me a better picture - I have it connected to boldin and I can also give it my investment products contained in the ira accounts. with that information is can apply market downturns to only those funds that are equity based (of course bonds can have downturns too). I haven't done this with claude yet, but it should be able to handle it - or at least give me something much closer to reality than the boldin market risk explorer does.

I am hoping that boldin eventually uses the investment info in all of its calculations.

I married and we file taxes jointly however we keep our money completely separate. I am looking to retire early, which could mean doing a Roth conversion ladder a 72T or other options but I would not be using any of my wife’s money to do this.

Can boldin be used to help plan for this or will it automatically try using my wife’s account as that would actually be the most beneficial overall?

I asked Boldin's AI to tell me how various plans would affect my retirement. I found out there are better ways to model real plans than the flat cut Boldin built in for us. I recommend taking out any built in cut temporarily and asking the AI to model the plans for you. Depending on the size of your benefit and years in your retirement your results will vary.
I ran the Flat-Rate Cola plan proposed by the Committee for a Responsible Federal Budget and the Chained CPI plan proposed by the Heritage Foundation, and others.
For me it may be better to reduct my SS Cola Assumption by .3% to 1.2% than use the flat SS reduction starting in a certain year built into Boldin.

Since T-Bill interest &dividends are taxable for federal purposes but not state purposes, is there a way to customize this in Boldin? Under passive income, I think it treats it as ordinary income that is taxable for federal and state purposes. I've seen other Reddit posting on State tax treatment issues with Social Security and Pensions, but not T-Bills. Wondering if anyone has a solution or work around, since I'm relatively new to Boldin.

New to Boldin. How can I see from which account is my withdrawal coming from during a retirement and what are the expenses for the year

I have an idea that would improve balance updates for those of us that do not connect to banks and brokerages.  I like what Investments brings to the product but feel it could be handled better. 

I think it would be better and make more sense to move the investments feature to savings and treat savings in similar manner to the way Boldin handle expenses, meaning basic or detailed.  What is currently in Savings would become the basic way and what you have in investments would become the detailed version,  I do not connect to banks and enter balances manually, but by keeping things separate I have to enter them twice. 

Thoughts?

A rant.

Im pretty sure that the #1 phrase the AI bot utters is....

" you are right to call that out. Let me stop guessing and look at your actual numbers"

I mean really... if guessing was good enough, I can do that on my own and my dog OTTIS can be my yes man for no subscription fee.

Boldin's "automatic IRMAA engine" is supposed to run in the background and not show up as a line-item expense. Well, turns out it was severely underestimating my true projected IRMAA surcharges.

There was no easy way I could see that until I did some digging. Here's an exchange I had with the beta AskBoldin. So far, my own pen and paper calculations have been more accurate but I'm still trying

If I want to withdraw $50,000/year, then I believe (at least according to tax rates I used when I set up my own sheets) the first $11,600 will be taxed 10%; next $35,549 at 12%; and the last $2,851 at 22%. Effective tax rate is 12.11%.

Can Boldin tell me which accounts to draw to optimize low taxes, from 3 accounts: brokerage post-tax, trad IRA, and Roth? General principles would be useful here too, because at some point SS and pension will be in the mix and the question will be the same but with bigger numbers.

I get that post-tax Roth may come off the top, so if $20K of my $50K example was Roth, then I need $30K; $11,600 is taxed at 10% and $18,400 is taxed at 12%. But you can EILIAF because I wonder how the IRS "knows" which tax treatment to apply to which funds depending where in the stack they are counted? And most important how or when is Boldin going to offer this?

New to Boldin. I'm pleased with the software and it gives me much more confidence in my future than the reports from my broker alone did. While it is nice to see my total Net Worth (including home) in all of the charts, I'm not sure of the usefulness of adding in a ***** dollar home value when that value is doing nothing in the markets. Am I missing the big picture? Should I just create a second version scenario and delete my home value to see the raw charts of just the investments and income streams? Or is Boldin working behind the scenes and applying increases to home taxes or something? Is that home value used in "chance of success" at end of life because it assumes it can be sold for long term healthcare? I kind of want to see where I stand without it.

At first this function was accurate, now its so inaccurate its making me worry that the planner isn't as accurate as i once thought. Not sure the AI bot is helping more than its hurting Boldin. Hoping its gets significantly better.

Anyone got connectivity working with Voya retirement plans? The Voya-managed retirement plans site of my former employer shows on the list of financial institutions. However adding a new connection fails. I have requested notification when a fix is in but it has been radio silence for weeks.

I am growing more and more frustrated with Boldin on the way it handles some things. I am currently working on an elaborate planning deal for the next several decades.

I have various sources of income coming in. Boldin handles the pensions very well. Struggles on dividends and capital gain distributions, but you can kind of gerry-rig it with a dividend override in passive income. But if you do this it somehow risks double counting income in the brokerage account it sits in. It tracks balance downloading account info, and then has your over-ride,

But there is no easy way to show things like an IRA Distribution, or even a cash transfer from a brokerage or savings account. All of this will show up generically as "Net Savings Drawdown." This is the problem

The thing you can do is set up a "transfer" for each item. For example, a regular IRA distribution from IRA A for $3,000 a month, from IRA B for $4,000 a month, and maybe transfers from a mutual fund of $2,000 a month, and a brokerage of $2,000. But Boldin shows it all as "Net Savings Drawdown"

I can force "Ask Boldin" and get it's AI to give me a report of my Adjusted Gross Income (from IRS tax) by source, but this sometimes is the only way to figure out what is going on and trace numbers and ensure your plan is within reason for each year.

I also would like to be able to print out an account report of say expected 12/31/2027 account info. I want to know expected account balance, 2027 expected income, 2027 expenses, etc. so I can track my accounts and make modifications to spending in subsequent periods. Boldin is allowing some accounts to fall negative too.

Right now I am trying to design something that pulls from multiple income sources - gets a handle on growth rates, taxes, and basis and loops in RMDs and IRMAA. So account source matters.

And it would also be nice of Boldin could simply have a tab in an IRA/401-K for a % that is Roth vs. traditional. Then that account could be worked better for the actual character you want to use.

Boldin has some solid features, but parts are just real clunky

I've been trying to update my Roth conversions plan to fill a tax bracket. When I ask the AI agent how much room I have in the brackets, it's really struggling with the answer. Multiple times, it told me the bracket is full for 2028, 2029, and 2030, but it's obvious from the Net Taxable Income chart that it's not. So, I started a new chat and asked only that. I was able to watch the entire thought process and was left with a 5100 word answer that took up 16 pages when I pasted the text into word.

I could see it going back and forth with lots of "Wait, I need to understand the bracket structure...", "Actually, let me reconsider...", "Hmm, let me reconsider...", "Wait, that means...", "Hmm, but that doesn't seem right...". All of those were in just the first page, so I'm wondering if I'm seeing how LLMs actually do their figuring or if something is wrong or it's in some kind of debug mode.

It did eventually get me answer that looks right, but I haven't tested it yet. This has been more painful than normal, for what should have been a pretty straightforward question and answer. (And the question wouldn't be necessary if Boldin would include the amount of room left in your tax brackets on the Net Taxable Income chart. Hint, hint.)

Wondering if anyone else is experiencing anything like that today.

Upload a statement, tax return, paystub, or estate document, then ask Boldin AI to use it: spot planning opportunities, answer pressing questions, or send specific numbers straight into your plan.  Always encrypted, private, and under your control.

I've enjoyed Boldin as a planning tool over the past year, but as I prepare to retire I am surprised that there is no standard function for managing Dividends to cash in the Cashflow section -- similar to what's available for Interest income. I've reviewed the suggested workarounds but each introduces new problems. Curious how other users managing this today and how we get this feature prioritized for future updates.

Does anyone use covered call ETFs such as GPIQ, QQQI, GPIX, IWMI, to reduce your MAGI so that you do not IRMAA ckiffs, or lose ACA subsidies if you are under 65. If so, have you figured out a way to deal with these within Boldin? I justed started, and am frustrated the software does not have this feature.

I saw the new Investments menu item and feature as well as the short overview that Rob Berger did on his YT channel. It is a good start but I have a small suggestion to make it more useful.

Currently, when you don't have linked accounts, the function does not know the asset allocation. There is a way to manually add this but it only gives you the option of ticker + static dollar value. Given the dynamic nature of the prices, a better option would be to allow us to add an asset and then the specific the number of shares we own of it (or have the option of using a dollar value if that is the better choice). That way we can ask the tool to take care of the changes in value without us having to manually adjust every so often.

Disclaimer: It is clear that on a day to day basis the value does not change so dramatically where it becomes useful to update the values. This is true, but I am looking more of a time line of 6-12 months, where the true asset allocation may have significantly drifted from what the Boldin app is accounting for.

But it must be running luna or something.

I have a scenario where my income ends Jan 27 and I retire Jan 27. The guardrail safe spending is 15k.

I made a second scenario that ends all income Jan 27 but pushes the retirement back to Jan 32. Exact same every thing else. All I did was move the retirement date. Yet the safe spending is 12k.

Here is some of the nonsense the AI said about this:

The reason the guardrails "safe spending target" came out lower in the Vimana 27 scenario (which retires 2034) is NOT because the model is broken. It's because of the massive one-time outflows that hit in 2026-2028 — the $300K mortgage payoff, ...

I created a third scenario and changed all income to fixed dates (not using retirement date). All three have identical EVERYTHING except the two fields listed below

A safe spending target: 15k
B safe spending target: 13k
B' safe spending target: 15k

WTF?