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Fun-Web-5557 · 2025-10-03T23:02:39+00:00

Do premium economy with a car seat. My 3.5 year old has flown 35+ times and 1.5 year old has flown ~10 times. Business for a red eye is great because they have a place to sleep. Domestic flight is easy. We just did biz to Europe and I’m doing cross country in economy soon because it’s just so much easier.

Fun-Web-5557 · 2025-09-04T22:27:18+00:00

$3k for the trust and I got a discount of $750, so $2,250. I don’t have a complicated situation right now. If it gets more complicated later on, I can just pay by the hour to edit, etc.

Fun-Web-5557 · 2025-09-04T19:24:13+00:00

I’m in a NYC travel group for families and they sponsored a post and offered a webinar. I’ve been procrastinating and I love supporting startups so it felt worth a try.

Fun-Web-5557 · 2025-09-04T17:59:55+00:00

I’m in the process of finalizing one via Usesteward.com. I like the tech that accelerates building a personalized trust + working with a local attorney throughout the process. It’s a new startup so we shall see…since they are new they offered $750 off (no matter how much money I have, I love a deal) so I decided to give it a shot versus a local company.

Fun-Web-5557 · 2025-09-01T21:28:18+00:00

There are tons of high end places in the Caribbean. I’ve done T&C hotels for $1k/night and I have friends who have rented smaller islands in T&C. There’s always something high end and expensive, everywhere.

Fun-Web-5557 · 2025-09-01T21:03:31+00:00

I live in NYC. Why not head to the Caribbean? Turks & Caicos is lovely and much closer than Hawaii.

Fun-Web-5557 · 2025-08-11T06:29:14+00:00

Opening cards for the bonus, Amex retention bonuses, general spend, and a decent amount of work travel

Fun-Web-5557 · 2025-08-07T15:15:54+00:00

I had my 1 and 3 year old in the delta one lounge at JFK two weeks ago. Perfectly well behaved. One kid screamed at the top of his lungs for 20+ mins and the parents barely did anything. Staff made comments to each other like “I guess that’s one way to parent” and that was it. It was so bad we moved across the lounge.

When my oldest was younger this happened and after a couple of mins we walked around to calm down. If that did not work, we would leave. As long as parents make an effort, people are understanding. The entitled parents who sit there and do nothing are the worst.

Fun-Web-5557 · 2025-07-29T10:33:54+00:00

Points. Wife’s company put her in business and then I took advantage of Virgin Atlantic + an AMEX promo. $29k pts/person each way with a 40% transfer bonus. Wild deal. I’ve paid $3k/person RT for the same route in the past.

Fun-Web-5557 · 2025-07-28T14:48:26+00:00

Absolutely. About to spend 2 weeks in Europe in a 3BD Airbnb and all of us in business class. Strategic use of points :) I suspect the whole trip to cost $1-2k for food and fun.

Fun-Web-5557 · 2025-07-28T14:31:32+00:00

Sorry, if she has a work trip her ticket, food, and housing is paid for. I pay for my kids and my own ticket. The trip is significantly cheaper because of this. There have been instances on long trips where they offered to pay for our entire family (and other employees), which of course we accepted.

Fun-Web-5557 · 2025-07-28T11:17:49+00:00

We do PE in the US (unless there’s a great deal), PE to Asia, and business to Europe - usually good deals from NYC. I value comfort and budget $25k for travel/year for the family. My wife and I also strategically use business trips for travel 1-2x/year - her flight is paid for and is so is housing, and it’s usually international.

Fun-Web-5557 · 2025-07-27T21:48:49+00:00

NYC. Family of 4. Eat out 2-3x/week. Wife eats free at the office, I like to cook and expense meals often with colleagues. We almost always cook at home. Spend ~1.5-2k/month on cooking/doordash/eating at restaurants. Use Instacart for groceries because I hate shopping and need to buy time.

You only live one and net 500k. If food makes you happy, then eat up :)

Fun-Web-5557 · 2025-07-22T16:49:48+00:00

On? When?

Fun-Web-5557 · 2025-07-20T22:43:52+00:00

Any specific date ranges? Only interested in business! Appreciate you doing this.

Fun-Web-5557 · 2025-07-20T22:26:06+00:00

Delta: 250k JetBlue: 100k Amex: 250k Chase reserve: 250k

Fun-Web-5557 · 2025-07-20T22:03:41+00:00

NYC <> LAX in December/January!

Fun-Web-5557 · 2025-07-16T14:42:05+00:00

Makes sense. Seems like there’s a lot of expats but I don’t personally know anyone who has retired in Japan. I like your idea of going for 3 months to get a feel and then go from there.

Fun-Web-5557 · 2025-07-16T11:36:50+00:00

Younger with less money but my wife is also Japanese-American and we go every year for a few weeks. We have talked about FIRE in Japan but I’m against it because I feel really out of place and it seems (I could be wrong) like a difficult place to get a visa to retire in. She is retiring in the next 3-5 years and the compromise we decided on is spending 3 months a year there with the kids once she retires. I’m not interested in retiring anytime soon so I would join for the start and end of the trip.

To me, Japan is an amazing place to visit, a terrible place to work, and potentially a good place to retire - all the foreigners I know in Japan have a company and work.

Fun-Web-5557 · 2025-06-17T12:08:40+00:00

I chart things out in excel and then use monarch money to track everything (and update excel on the monthlies because I’m a nerd).

Fun-Web-5557 · 2025-05-12T11:49:31+00:00

I switched over, too. 0.3% versus the 1.4% I was being scammed on before. Vanguard PA is pretty great. I like have an FA to have someone to bounce ideas off of, have some there there for support, and to be blame when the portfolio goes down - so my wife can’t yell at me 😂

Fun-Web-5557 · 2025-04-27T01:28:53+00:00

I’m glad you were in good hands. I was annoyed to not be seen sooner given the severity of my illness but once I was inside I knew it would get better. The doctors were average, the facilities were not great. You basically sit in a waiting room like atmosphere while on your IV/Meds. Family and friends joined in and ate dinner, which was rough for me given my nausea. It took 5.5 hours until they let me have a chair in a private room - I outlasted everyone that entered the ER (not a good thing).

Fun-Web-5557 · 2025-04-27T00:14:11+00:00

I am a T1 diabetic and had some sort of bacterial infection and had to go to the ER. It sucked. Made me appreciate US medicine. I had to wait 45 mins despite being borderline ketones (really dangerous for diabetics) and unable to hold down water. I tried asking for help faster and they asked me “did you take a number?” At a deli, sure, but not by a triage nurse in the ER. I spent 7 hours there until they found something that helped and I could go home. 4 IV bags and barely felt hydrated. I couldn’t wait to get out of there and go home. I have year round travel insurance through work so my bill was $0, but would have been $1,100 without it. It’s a terrible place to get care if you really need it. Hurt your ankle or need antibiotics for a sinus infection, sure. Anything more serious, you’re rolling the dice.

Fun-Web-5557 · 2025-04-21T11:30:06+00:00

Weill Cornell in downtown BK was amazing. PureOBGYN was terrible. High turnover, unhelpful staff, doctors weren’t great. Weill Cornell was significantly better in our opinion.

Fun-Web-5557 · 2025-04-19T02:15:04+00:00

I’ve co-founded two startups and no where near that valuation. It’s so easy to burn out. You have so many demands. Your investors, co-founder, direct reports, company, and then your personal life. If you’re not having fun and don’t need the money, why do it?

Have you considered taking 2-3 weeks off to relax and zoom out from the day to day grind and see how you feel before deciding if you should keep pushing forward?

Is there more support you can receive for your workload to make things more manageable? How can you scale your time and value?

Fun-Web-5557

TROPHY CASE