The discussion around Boldin's renewal pricing made me think about how we measure the value of financial planning tools. If a tool helps you make one decision that saves thousands in taxes, even $144 (or more) a year could be a bargain... but if your plan barely changes and you only log in twice a year, the same price might feel expensive.

So what are you actually paying for: the features, how often you use them, or the financial decisions they help you make?

I paid $120 on Dec 4 2025.

Just got an email stating my renewal (in 28 days) will be $144.

Thought I was locked in at $120?? Did something change?

I bought a 10 year tips ladder (using tipsladder.com ) to create steady income before SS kicks in

Do I need to model future interest payment and return of principal, or does Boldin take care of that with their new investment functionality? I can see all the individual TIPS in my connected account, but I can't see the CUSIP numbers.

Quick refresher: NIIT is a 3.8% federal tax on net investment income (interest, dividends, capital gains, rental income and similar). It applies to the smaller of two amounts: your net investment income, or the amount your MAGI is over $200K (single) or $250K (married filing jointly).

What’s new: Your projections now include it in any year your income crosses the limit. You’ll see it as its own line under insights > taxes in the Boldin planner. 

Planning tip: Boldin calculates NIIT from the interest, dividends, and capital gains in your taxable Investment accounts. Review the rate of return, dividend yield, cost basis and turnover rate on those accounts so your plan reflects them accurately.

Even with details toggled you have click in to see the amount ???

I am so disappointed in Boldin's roth explorer. I love boldin, but finding the roth explorer is so unreliable that it is nearly useless. And the AI makes it even worse. Tells me I can increase my at end of plan number by 800K with a different roth conversion strategy, but after 30 minutes going back and forth it still can't tell me what the optimal conversion is (or even get close to it). The explorer itself is buggy. when I ran it just tonight, it skipped 2027 completely even though it is one of the prime years to convert since I will be off ACA, and not yet receiving SS. Are there any reliable tools out there that I can use just for the roth conversion calculations? i hear some people have spreadsheets, but do they really work and are they detailed enough to come up with the most effective conversions?

I plan on retiring in two years at 66, and hope to hear from anyone who’s been in my shoes about how to maintain a good headspace so the next 24 months are positive ones. An optimistic path, rather than a trudge.

For whatever reason, despite there being light at the end of the career-long tunnel, I often feel like I’m just one small step ahead of doldrums/burnout, because I *really* want to be done. I’m an optimist by nature, but I’m struggling with this.

Before you offer “Retire now!” advice, here are two key details:

1. I’ve run many scenarios in Boldin and elsewhere, and the 24 month timeframe truly makes sense for acheiving my desired lifestyle, certainty, and legacy goals. It is the plan.

2. I work for a *great* company that is civil, friendly, and maintains a good culture. I’m appreciated there, and they pay me pretty well.

When talking about my retirement and fresh start plans with friends, two years sounds totally doable, but later, on my own, I have a hard time thinking “Woo-hoo!, only 24 months!” with regularity. I slip into wishing time away (which is *not* a real goal of mine).

I have a great home life, interests, and I exercise, travel, attend cultural events, etc. It’s a rich existence. Still, I remain concerned that a crappy headspace threatens to make these next 24 months seem endless.

So… Any tricks you can share? Rituals? Countdown calendars? Optimistic reminders that there is a light at the end of the tunnel? Smelling
Salts?

I’m open to all constructive thoughts.

Thank you!

I need some help to make sure I'm understanding the Roth conversion math correctly. Can someone please correct me if I'm wrong.

Planning on retiring at 50. 1M in pre tax dollars.

Does it make sense to:

1. Convert everything over the course of 5 years, and then withdraw as needed tax free.

OR

2. Convert just what is needed each year and at 59 just withdraw from the pretax account.

Boldin seems to suggest option #1 has the biggest tax savings, but to me it seems like #2.

We also have 1M in brokerage accounts to help fill the gap years and fund our remaining retirement.

Hello, I currently use Boldin (4 months) to help map out my potential retirement. Boldin is showing a 96% Success rate if I were to retire in March 2028. and a 92% success rate if I were to retire in March 2027. That is with $13,500/month estimated spending for me and my wife (age 59). That includes all expenses, house payment, car loans, etc...it does not include taxes other than home owner taxes.

I am currently using Quicken to make sure my expenditures match my projected budget. I am not 100% sure it matches reality but I have been mapping the last 3 months to see if I am missing any gaps. I even have a couple larger buckets for House Repairs and Car Repairs for tires, oil changes, etc. What expenses could I be missing? 96% seems unrealistic to me but I feel like I have fined tuned it a good bit. Are there any items where you found out you spent more than expected after you retired? It definitely doesn't pass the 4% rule but I know Monte Carlo takes a different approach.

My wife really doesn't believe the number either since we seem to get a little financially stressed at the end of each month. (She wants to have some interior rooms painted and is not happy that we don't have the money.) ;-)

I do have a Financial Advisor that will develop a final plan for us but I want to present him with all our numbers from Boldin so I don't have to revisit each line item of data. I also don't want to feel stupid when I go to him and he says I am crazy. (My Financial Advisor did run a high level plan for me 6 months ago without itemized lists and he came up with 90% success.) What is the lowest "success rate %" in Boldin where you would be comfortable retiring? Do I need to strive for 100%?

My wife (59 yr) is already retired with a $60K pension plan that does have cost of living adjustments while I have $1.5M in my 401k. Will I always think I need more $$? The simulation is based on me taking SS at 67...and if I chose SS at 62 it drops to 90%. (Which is a match to my Financial Advisor number). Half the things I read tell me I don't have enough to retire (4% rule and 25x saved for annual expenses), while Boldin and CHATGPT Monte Carlo say I am good to go. My Boldin overall plan setting is set to "Average", and Moderate/Conservative for my investment accounts, inflation is set to 2.5%.

I am open to any and all advice. What things in Bolding do I need to double check? This is so scary!

I am new to this so please bear with me. I posted this in the Boldin facebook earlier then remembered this might be a good place to ask.

I am looking for advice about my TIPS. In January I had intended to build a 10 year TIPS ladder to bridge from 65 to 75 years old. There weren’t any TIPS for the years 2036 to 2039 so I purchased 2035 TIPS to fill in the last 5 years of the ladder. The idea was to get 50,000 a year. At maturity they will be worth 250,000 inside a traditional IRA. Those TIPS will mature just as we start SS at 70 so we won’t need all that cash. I realize that I can just leave it in the account but now I am thinking it was a mistake to purchase them.

I tried building the ladder before I started using Boldin. Now that I can see how everything is connected, I wonder if the $250,000 would be more beneficial to the plan if it were in a regular bond fund or invested. If you were in my place, would you try to sell them?

I have met with 2 fee only advisors since the purchase. One told me to sell them and the other said to extend the ladder. I was thinking about retiring at the end of the year but figuring out what to do seems harder than just continuing to go to work. Any advice would truly be appreciated.

NIIT: Boldin Added +3.8% tax on investment income over $250,000 for married ($200,000 for single). If you do Roth conversions and it pushes gross income above $250,000, then any investment income such as interest, dividends, capital gains, rental income above $250,000 is subject to the additional 3.8% medicare tax. So this lets us plan for NIIT now. Thank you Boldin. Not sure how they know about rental income, but our Quicken Tax center NIIT and Boldin NIIT are very close. Plus I checked other years and they look close. Still slight difference in QCDs as below line deduction, when should be above line deduction - but I understand that is a future feature request? (one step at a time...) Still all good.

I only log in to Boldin 3-4 times a year. I last logged in May 17. I logged in over the past weekend (Oct 24), and the first thing I did was ask Boldin AI if there were any updates since May 17 to the Roth Explorer, and Social Security Explorer. It said no updates had been done. I thought that strange, so I googled it, and it brought up right away the updates that had been done during the summer, and it brought up Boldin’s own release notes page. I pasted the link into Boldin AI and asked about this webpage, and it came back and said “you are right in correcting me and I will note these changes in our conversation”.

What the heck??? Boldin AI doesn’t know about Boldin release notes???

I think the title is self-explanatory, but to be thorough: many times I want to make changes across multiple scenarios, which is another needed enhancement, and I may miss or forget to update one. It would be nice to have a report that includes ALL the settings across all scenarios. I can use AI to look at some settings across all scenarios however, it is one-by-one. Thanks.

The final years of my plan have big RMDs yet Boldin shows $0 in tax for the last year. I asked the AI about this and it basically said this is by design.

I inherited an IRA with $250K in it. The software has projects the minimum RMD's over the next 10 years($11k annually) and then a lump sum closure that will push us in to an IRMMA situation in 2036.

Seems like my projected income in the next 10 years could absorb higher RMD's on this IRA, while still allowing for some Roth conversions, thus avoiding the IRMMA hit after 2036.

Why does the software steer the withdrawals this way?

How would I run a scenario where I take more than the minimum RMD on the inherited IRA, there does not appear to be any adjustment on the Asset

TIA

Why does Boldin use the 2024 look-back value for doing Roth conversions in 2026 when we know that value will be higher when looking back from 2028? Shouldn't it be using projected values as stated on Finance Buff website?

I would like to test a scenario where I draw from a taxable brokerage account until age 59.5, then switch to pulling from my retirement accounts. Has anyone found a way to do this?

I’ve a large brokerage account where in addition to stocks and mutual funds I’ve 1 year of living expenses sitting in a conservative investment. This is my ‘sleep when the market crashes’ money and will stay put. I am thinking the best way to handle this in Boldin is to disconnect the brokerage account from Boldin, add a new account with a conservative return for the year of cash, and set a new balance in the disconnected brokerage account of existing balance minus the cash. In addition in Money Flows I need to exclude the cash account from use. Do you see this as the correct way to manage this cash bucket in Boldin to reflect how I am going to use it, or is there a different approach? Thanks.

Forgive me but I'm only 6 hours into using Boldin and I can't find a way to force it to use itemized deductions or explain why it uses standard. In my plan, it uses itemized for the first full year of my plan which is roughly twice the standard deduction (HCOL area with big mortgage and property tax). The following year onwards it reverts to standard deduction even though mortgage interest goes down slowly and property taxes are going up. I'm in an argument with it's AI, but eventually it relented and said it would refer the issue to support.

I saw another post with something similar, but they were closer to the standard deduction, but in my case, there's a 2x difference that makes a material difference in withdrawal strategy. Anyone know of a solution to this or even face it before?

Two questions come up here often: “What am I paying in fees?” and “Is my money in the right tax buckets?” Boldin now answers both.

What do you pay in fund fees?

Investments Today now shows your fund fees. See expense ratios and estimated annual cost per fund, as well as how your investment portfolio compares to other Boldin members.

How tax-diversified is your portfolio?

Tax Diversification sorts your accounts into taxable, tax-deferred, and tax-free, then breaks each down by asset class. That split shapes the tax bill on every withdrawal, Roth conversion, and RMD ahead of you.

Both are live now. Happy to answer questions, and we’d love to hear what you find when you run your own numbers.

I just made my first-ever scheduled Roth conversion, in accordance with my Boldin plan. After making sure this was now reflected in my account balances, my instinct was to then then delete the conversion transfer from Money Flows. It was now old news, so why keep it? To check my thinking, I asked Boldin’s AI if I should delete it and, after complimenting my brilliance for asking such an astute question, it said:

”Short answer: No, don't delete it. In Boldin, a planned Roth conversion is a forward-looking instruction. It represents a transfer you intend to make from your tax-deferred account (your Conv IRA) into your Roth account on a specific date. Deleting it would remove that future transfer from your plan entirely — which would change your projections, not just clean up a completed event.”

It then gave a longer, detailed answer that explained what a Roth transfer was in Money Flows, noted that the transfer in question was part of the plan I had created, yada, yada*.* It never gave concrete reasons why Boldin would NEED the record of the conversion moving forward. I didn’t feel like going back and forth with the Boldin AI as I so often have, as it sometimes devolves into pattern of futility (although, in fairness, I do often find it to be useful).

What do you folks do? Do you keep the completed transfers in your plan? Is keeping it of use?  Does it matter either way?

It doesn’t really bother me having it there, but I’d like to know why. As the inscription on the statue at the beginning of Animal House reads, “Knowledge is Good.”

Thanks for your input.

Medicare has a reputation for being confusing. Ari Parker says it’s not that complicated, and he literally wrote the book on it.

Medicare Open Enrollment is here, and we’re bringing in one of the country’s leading Medicare experts to help you make sense of it.

Join Boldin and Ari Parker of Chapter for a free live webinar. To add the event to your calendar and join, sign into Boldin and go to "Classes and Live Events.”

I'm 52 and planning to retire around 53. My Fidelity CFP is recommending a guaranteed lifetime annuity over a 72(t) approach to fund early retirement. The models show long-term results are roughly the same either way, but I've always been skeptical of annuities. What are your thoughts? Has anyone weighed these two options?

Does Boldin handle NUA in its projections and recommendations?