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Hey all. Second-time technical founder here (ex-CTO, raised ~$16m from a16z for last startup). Currently building in legal tech
I'm looking to chat with a litigation partner or firm owner. I'm stuck on a specific piece of customer psychology and could use a sanity check before I burn 6 months building the wrong thing.
I'm building against massive incumbents that users openly hate but never leave. My product is superior (solving the specific accuracy gaps that force them to use Excel), but I'm realizing that "better product" might not be enough to overcome the inertia.
I need a sanity check on my go-to-market motion. I'm trying to figure out if I can actually win on product superiority here or if I need to pivot the entire sales pitch to fear/liability to force a switch. I feel like I'm bringing a Ferrari to a tractor pull and need someone to tell me how to actually sell it.
Hey! I am neither, but as a fellow poster. I’m more than happy to take a look just out of interest and the at the off chance I can provide insight!
If you like travel, travel in your youth as much as you can barely afford to.
I recently completed a milestone trip with old friends. A repeat of a trip from 30 years ago made then on the most shoe-string of budgets.
Now, better circumstances. Better lodging. Good food.
Yet…
Half the folks couldn’t do two-thirds of the activities because of mobility issues. The other half couldn’t eat three-fifth of the menu because of dietary issues. And the third half, I suspect memory and acuity issues at play.
The light of Eärendil is fading…
Die with zero is a pretty good book that covers this sentiment in depth, totally agreed.
While I fully support that shoestring traveling in your youth is its own great experience, there is something to be said for having a deeper understanding of what you are seeing and why it is interesting other than simply exotic.
100%. Experiencing the true magic of being young, broke, and on your own 10,000 miles from home really does have a time limit.
(Reposting here as prev post was removed )
32M, married, first kid on the way. Live in a HCOL West Coast area.
Careers: I’m a software eng in big tech (10 years), wife is in healthcare.
Household income: ~$500K currently
Liquid net worth/stocks: ~$5m. 401k is about 10% of that.
Current spending: ~$170K/year (expected to increase with kid obviously ). We’ve lived under means for years home wise and as of now save 10-15k a month easily.
Existing condo 1 bed would rent out roughly break-even.
We’re looking at buying a ~$2.5M home, with about 40% down. Feels like the opportunity cost of the down payment is really high. Leaning towards no.
Financially it’s doable if we maintain our jobs and general trajectory, but I want to be thoughtful about the long-term impact on flexibility and FIRE goals.
For those who are farther along the FI/FatFIRE path or have made similar decisions:
Would this seem reasonable at this stage? If you bought a higher-end “long-term home” before full FI, did you feel it helped or slowed things? Any considerations you wish you weighed earlier when upgrading housing and lifestyle? How long would you wait to buy the house and how would you finance it?
Appreciate any high-level perspective.
I’m in the same boat - mid-30s, similar NW, comparable budget for the upgrade, and expecting our first kid soon.
My main strategy is to delay buying for as long as possible. We think we can comfortably stretch our current 3B house for at least another 2–3 years. When we finally do pull the trigger, the plan is to aggressively pay down the mortgage in the years following.
My reasoning is simple: a much larger house is just more expensive to maintain across the board (higher property tax, interest, insurance, and general maintenance costs). We also may need to move right before the kid hits school age, which makes choosing the location impossible right now.
I know there’s a risk that housing prices jump significantly, but I’m betting that the huge increase we saw during the pandemic was a once-in-a-lifetime event.
(Btw I'm pretty curious how your accumulated 5M in 10 years. Did you have some very successful investments?)
More of your assets in personal use real estate simply slows down your path to FIRE. It is short term consumption instead of leaving the money appreciating. So if FIRE is your goal, dont upgrade until you have reached your FI number.
I bought my house 5 years ago for $1.7M with $650k down payment when my NW was $3M liquid.
Now my NW is $7.3M liquid and my house has appreciated to $2.5M.
And I live in a beautiful house with a view of the ocean a few blocks away, entertain here, and feel a part of the community.
So my experience has been great.
5 years ago what was the interest rate? Your investments did really well regardless so nice job, but your opportunity cost of your down payment must be similar high in that case
Opportunity cost? Not sure I understand. I’ve made 125% on my 650k. The S&P 500 has done about 95% during that period. Leverage means a 40% rise in housing value triples considering I only put down a fraction of that. And keep in mind the house is an asset -I can rent it out, swap it, take out a line of credit etc.
And the cost is fixed while rents in my neighborhood are double my mortgage and still rising.
I don’t think you computed your opportunity cost on the house properly but ok. If you didn’t buy the house and saved and invested instead, do you think you’d have achieved 5-7m liquid faster an now afford a better home? Again, liquid outside of paid off home in my option matters more than NW.
I’m curious what’s your recommended way of buying a permanent house. Should one focus on FIRE and wait until they have enough liquid assets + cash to buy the permanent house in cash? The only downside is that it could a long time and you wouldn’t be able to enjoy the utility of a nice house during that period. Renting is an option but rental houses are either as expensive as mortgage or in very poor conditions.
Wait so you haven’t been able to contribute to your liquid investment much because 3M without any contribution would be like 6M today?
Yeah haven’t been able to contribute as much, maybe $750k the last 5 years…just haven’t had the big paydays ( I’m in tech sales so hit or miss) and also paid a ton in taxes.
And keep in mind it was only $2.2M after my down payment and some house improvements.
Hey all, I’m a mid-30M doing reasonably well in my corporate job, making around 1-1.5M annually. I started in tech after grad school 6 years ago, and my net worth is just over 4M, with 90% in the S&P500. It feels decent, but growing up with overachieving peers, I know people from similar backgrounds whose wealth and income have skyrocketed.
I often wonder if I’m taking enough risks in both my career and investments. I read a lot about index fund investing when I started working, so whenever my RSUs vest, I liquidate them and buy S&P500. But talking to others, this seems uncommon. If I had just kept the RSUs, my net worth would be 50% more. Career-wise, I’ve stayed at the same company because I thought my trajectory was good, and I worried that trying something new would “reset it.” Meanwhile, some friends jumped into AI early through job hopping or startups and are now thriving. (I work in an adjacent field, so it’s not too hard to switch, but I feel it’s too late to enter.)
Rationally, if I keep climbing the corporate ladder, there’s a good chance that I could hit 8-figure net worth by 40. But I can’t shake the feeling I’m not taking the best approach. Should I be more aggressive with investments? Should I worry less about my career path and explore more opportunities in my 30s? I’m posting here because I figure many of you had a pivotal moment that led to a sizable fortune. Would love to hear your thoughts!
Keep doing what you are doing and stop comparing to others. You are doing great compared to most people. There will always be someone with more or with a better, more exciting role. Learn to ignore than noise and have gratitude that you are making 7 figures in your mid 30s with a bunch of money saved already and on track to 8 figures by 40. If you don’t think that is enough, more money or titles won’t solve your problem.
Thanks for the comment. I usually only compare myself to others to see if I’m actually maximizing my own potential. What triggered this thought recently is the booming of AI. It feels kind of stupid not to pivot into that field, especially since I already have about half the skills needed for those roles. But part of me always wants to play it safe. AI is super competitive, and if I try and fail, I risk losing the stability I have now. Also, why bother pivoting when I already have a low risk but slow path to an 8-digit?
Just map out your reasoning.
Correct,also map out what happens if the AI bubble bursts and now none of the AI skills are needed...
As others said, you already have a bunch.
And what's the worst if you switch and it does not work out. You have years to go. As long as you don't squander what you have, do what you are passionate about and also have a good chance of excellence. Money will come, or compound
Hey - I'm launching an accountability cohort in January. :)
New to this sub-reddit. Looking to get my portfolio into a better state where I am less exposed to tech stocks, can better control my income each year and better manage taxes. I have more than enough capital to FatFIRE, but now I'm more focused on having a good hedged portfolio. I sold a large amount of tech stocks this year (but still a drop in the bucket) and I'm looking for a safe place to stash it that won't generate taxable income so that in future years I can take advantage of the $96,700 tax free capital gains point for a married couple. I'd also like to be less exposed ifs there is a significant market crash. My thought is a good tax-exempt bond fund like Vanguard Core Tax-Exempt Bond ETF (VCRM). Low risk, a return not too dissimilar from a HYSA -- but tax free so it won't lower my tax free capital gains point. Any thoughts on this strategy?
The easiest way to reduce volatility in your portfolio is to add bonds, particularly T-bills. You get the risk free interest rate, and the price of the bonds will rise if interest rates are lowered (unlike an HSA). Unfortunately that will create taxable ordinary income, but if you take just a tiny bit of more risk you can buy tax exempt bond funds. Look for one that is tax exempt in your state. The value of these funds will also rise if interest rates fall, which is better than a HYSA.
The tax free level is actually $125k after you include the standard deduction, so keep that in mind.
On the equities side, you can also re-allocate to high dividend ETFs which are going to have lower concentration of tech companies due to the tech companies having such high growth prospects that dividends make little sense.
Expecting first baby in April. Trying to understand the best strategy for 529 funding. We live in NYS. Initially, I thought we'd have my mother (68 y/o) open the account in her name w/ my partner as the beneficiary and start funding this calendar year to get the tax deduction, but now I'm realizing that only the account owner can claim the deduction in NYS. Wondering how others have gone about this in similar circumstances.
Not seeing the issue. Just open it in your or your spouse as the owner, and the other spouse at the beneficiary if the deduction is important to you. Having the younger person the owner is better anyway in case they change the rules about multi generation 529 transfers. But, you can also move the ownership later. If it is above the annual gift limit when you change the ownership, you can just report it and have it come out of your lifetime gift limit.
Open a 529 in your name now and add 38k, open one in baby’s name in May once you get social security and add 200k. Then you’re good as you’ll transfer yours to baby later.
No need to ninja it, value is in tax free growth not the little savings when you contribute.
I feel like people are way overfunding their 529s. $238k growing at 6% for 18 years is $680k in todays dollars. That's just way too much.
Yeh but real return is a lot lower bc of increase school costs. Lots are 95k/year already and only increasing
Can roll 35k into Roth IRA later or use for grad school
I think there’s zero chance that tuition growth over the next 20 years looks like it did in the previous. We’ve already seen tuition stall or even go down in real terms in the 2020s.
Curious why you posted in fatFIRE where 529 is probably not very important to most people here?
Curious why you didn’t just scroll past my comment and move on with your life.
Sorry, should have rephrased my question. Is there something about 529 that the fatFire group should pay attention to?
Hello everyone! I want to retire early, fat and happy. Any advice helps!
I am 27 years old making around $200k a year
I’ve got around $90k in checking/savings $90k in 401k (I am maxing from here on) $30k in stocks $14k in Roth IRA (maxing going forward) $300k in equity on a house Will likely be married in 2-3 years (spouse makes less than 100k)
I am fairly happy at my job, don’t love it. But my priority is to retire early or start something that I have a passion for (no passions yet)
Wanted to poll all you smart folks and see what recommendations you’d have for me
At your age I would focus on increasing the income and maybe not tracking the numbers so closely since the current numbers will quickly become insignificant. If you don’t love your job, treat it as a trade: are you really willing to exchange your valuable 20s and 30s life for $200k a year?
While $200k at 27 is a very healthy earned income, growing that over the next decade by doing two company changes with say 30% increase for each of them is going to make a massive difference in your long term wealth creation.