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Josh Lowenthal Profile
Josh Lowenthal

@joshualowenthal

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⚖️Lawyer | 🧑🏻‍🧑🏼‍👧🏼 Dad/Husband | 🚀M&A | 💰 Tax Planning | Went to @Umich , @WashULaw | Ex- @KPMG & BigLaw

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Joined January 2010
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@joshualowenthal
Josh Lowenthal
2 months
Wow! Have a couple new fresh faces faces around here. So time for another re-introduction. Hello there! My name is Josh and I am M&A and tax attorney helping business owners, searchers, and taxpayers navigate business buying, business sales and taxes (I really like taxes okay?)
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@joshualowenthal
Josh Lowenthal
2 months
This is your monthly reminder that having a single-member LLC provide literally ZERO tax benefit on it's own.
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@joshualowenthal
Josh Lowenthal
22 days
Hey #TaxTwitter …..She back!
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@joshualowenthal
Josh Lowenthal
2 months
@Laura_W_Gieseke @clhubes If you really don't want to be on a plane with a crying baby…..charter you're own flight 🙄 Children are just that, children. I'm right there with you is I guess all I'm saying lol
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@joshualowenthal
Josh Lowenthal
5 months
@collin_ruth89 Honestly this ain't that crazy and shouldn't be contentious at all. Talk to any family lawyer, ever, and they will tell you to do a prenup without hesitation. It has zero reflection on the marriage or the prospect of the marriage.
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@joshualowenthal
Josh Lowenthal
4 months
@SAOliver_Atty Wow, this sent me down a bit of a rabbit hole that I didn't mean to trek down. TL;DR: Esquire = Dr. Or CPA designations. But the shortest and simplest version that I can track down is that despite its questionable origins, esquire is to lawyers as “Dr.” is to Doctors. While
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@joshualowenthal
Josh Lowenthal
4 months
Alright friends, help me understand this because this is an issue I run up against ALL the time. This is fraud. Full Stop. This would get picked up at audit, and with a stronger IRS referred over to IRS Criminal Investigations (you know those IRS Agents with guns). But help
@Tilmon_Brown
Tilmon Brown
4 months
@alexforbes__ Purchase the car through your business. 100% deductible/expensed. Put her on the payroll as a consultant. Have her lease the car from your business at the rate of the car note.
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@joshualowenthal
Josh Lowenthal
3 months
This is a hill I might die on: If you’re a tax preparer and think that every 1099-NEC requires its own schedule C, you shouldn’t be preparing tax returns.
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@joshualowenthal
Josh Lowenthal
4 months
More criminal tax cases are coming. Was having lunch with a friend yesterday. He has not one, not two, but THREE tax fraud cases that he received calls about this week. Most with conservation easements. Be careful out there folks.
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@joshualowenthal
Josh Lowenthal
22 days
@ItsMattsLaw Absolute insanity. Their mental gymnastics though is truly impressive.
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@joshualowenthal
Josh Lowenthal
2 months
@FUtwitZZZZZZ Exactly. It provide liability protection, but not much else.
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@joshualowenthal
Josh Lowenthal
3 months
@MikeSyl36625988 So she’s not on twitter I don’t think, but Nina Olson (the previousUnited States Taxpayer Advocate) talks about this a lot. She is a big advocate for opening up more TAS case early and often because it helps the US Taxpayer Advocate when they go to seek additional funding from
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@joshualowenthal
Josh Lowenthal
1 month
People who have tax advisors that tell them to put real estate in an S Corp. I just have to ask, why?
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@joshualowenthal
Josh Lowenthal
22 days
@petercnordberg Oh you missed some prime content from this person a few months back on TaxTwitter. She’s a “Sov Citizen,” just a lot of nonsense involved here from her.
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@joshualowenthal
Josh Lowenthal
2 months
Been away for a hot minute here. Doing some family stuff 😁 Now that I am *slightly* more well rested and half of a person again. All I can say is that medical stuff with newborns, regardless of how mild or severe can be terrifying for any parent regardless of experience.*
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@joshualowenthal
Josh Lowenthal
22 days
@AMandoSchneides I’ve heard if you say something with enough conviction, it becomes true. 🧐
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@joshualowenthal
Josh Lowenthal
2 months
@anthony_ltd_ Sorry, should have been a little clearer (Twitter being twitter and all). I'll number these to help make responding a bit easier: 1. I'll concede that the "on its own" is doing the majority of work here, with the assumption that someone forming an SMLLC isn't making an S
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@joshualowenthal
Josh Lowenthal
9 days
@jennyrozelle Thank you for saying the quiet part aloud. I always get a good laugh, especially when I look at my friends in big firms and all I think about is, “Someone in firm admin sent an email out to remind people to nominate their coworkers.”
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@joshualowenthal
Josh Lowenthal
8 months
@SMB_Attorney There is a research based reason for this! Psychologist Robert Cialdini talks about this idea of “Reciprocity” - So when we get a gift psychologixally we feel obligated to return the favor. Ever get approached by a monk trying to give beads or a
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@joshualowenthal
Josh Lowenthal
12 days
A good lawyer will be able to give you an answer right away. A better lawyer is going to ask clarifying questions. There is so much that goes into giving the simplest of legal answers because there is never a "one size that fits all"
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@joshualowenthal
Josh Lowenthal
26 days
Be kind to others out there. We are all mostly figuring it out (with some very educated guesses along the way) Was talking with a colleague of mine: Worked in BigLaw, some major companies and now out on their own. They were telling me how nervous they were about giving a
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@joshualowenthal
Josh Lowenthal
2 months
While I am not the biggest fan of S Corps in general, here is one quick tip: If you've had an LLC and are converting to an S Corp, please for the love of god talk to a tax attorney. If you don't, I can *almost* promise you that you are converting to a C Corp, not an S Corp.
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@joshualowenthal
Josh Lowenthal
3 months
Consider yourself lucky if you can wake up most morning with a roof over your head, food in the fridge, and ready to take on the day. There are millions of people out there that aren't nearly as fortunate. Happy Saturday.
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@joshualowenthal
Josh Lowenthal
3 months
There can be a lot of questionable content on this app at times depending on where you find yourself. But the kindness and support you find here is also second to none. I have started to form some phenomenal professional relationships with so many people. In no particular
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@joshualowenthal
Josh Lowenthal
4 months
Talked with a potential client today. Spouse started a business and in year 1 did over $800k. When they found me they said, “look we’ve read all the blogs and articles but we wanted to talk to someone so this is done right and legit” 🤯 Unicorns DO exist.
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@joshualowenthal
Josh Lowenthal
29 days
Why do tax attorneys matter? We stop accidents from happening. Take for example a recent situation I had with a client where we were doing a basic restructuring of their businesses. One of the steps involved was to move one of the companies from State A to State B, it just
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@joshualowenthal
Josh Lowenthal
4 months
A common misconception that I get often is that people need a CPA over a tax attorney. This is a HUGE misconception that be a costly mistake for you and your business/HoldCo. Instead you need to have a team of professionals, business, tax, HR, consultants, etc. 1/
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@joshualowenthal
Josh Lowenthal
8 months
*Me, a Tax attorney, walking into the family holiday party* My family: “Oh there’s our little lawyer. What can I do to save on taxes from my W2 job next year?”
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@joshualowenthal
Josh Lowenthal
4 months
@MikeSyl36625988 Having dealt with Innocent Spouse cases and seeing the absolute horror stories involved on the controversy side, I always make it my practice to sit down with my spouse and explain to her our tax return BEFORE having her sign. It’s the responsibility of all spouses to handle
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@joshualowenthal
Josh Lowenthal
8 months
@CTW_SMB @SMB_Attorney Ha just go check out the Hobby Loss rules under Internal Revenue Code 183, an IRS favorite
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@joshualowenthal
Josh Lowenthal
2 months
@frankcowell I mean sure, you could have an LLC taxes as an S Corp. However, I would venture to suggest that most (including myself) would probably advise against that. At best, you're bringing down your SE tax, at worst you're sitting on a C Corp that you think is an S Corp. But still a
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@joshualowenthal
Josh Lowenthal
2 months
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@joshualowenthal
Josh Lowenthal
1 month
SMB Twitter professionals, take time to meet each other. There are some awesome people in this space who are well worth getting to know. Recently have had some great conversations with: @ryanraysr @patrickdichter @petercnordberg @mattrbowles Definitely worthwhile to reach
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@joshualowenthal
Josh Lowenthal
9 months
@LoganGrafTax Do it! While it's not necessarily tax prep, us lawyers take fees up front all the time. The one rec I'd have is treat the funds like a retainer. Create a separate “drip” account and move money over to your operating on completion.
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@joshualowenthal
Josh Lowenthal
3 months
Alright, I’ll be the one to say it. What is with conference pricing? Yes, I fully understand that conferences are a big production. However, for professionals, searchers, students, and everyone in between who are in growth stages, a $5,500 conference simply isn’t feasible.
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@joshualowenthal
Josh Lowenthal
19 days
I’m curious, how do people deal with “Client Emergencies?” It’s happened to me frequently when I have a lunch or other meeting scheduled with a colleague or peer that gets cancelled for client emergencies. Sometimes these are real and other times they are fabricated (which I
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@joshualowenthal
Josh Lowenthal
22 days
@cordes_tax neither do I, neither do I 🫠
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@joshualowenthal
Josh Lowenthal
21 days
Starting to get a lot of targeted ads on Instagram/facebook at the moment about all these tax planners. They claim to “help you find the loopholes that the rich don’t want you to know” This is just a friendly reminder that taxes are hard and there aren’t any “loopholes” out
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@joshualowenthal
Josh Lowenthal
3 months
Have you ever heard of materiality? If not let me give you a quick primer:
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@joshualowenthal
Josh Lowenthal
2 months
There are those that say the American Dream is dead. Personally, I disagree. The American Dream was never to move to the U.S. and work a 9-5. It has always been that ability of those with "less" to be able to build something greater than themselves for their children
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@joshualowenthal
Josh Lowenthal
9 months
Time for a brief re-introduction because it's been a while since I was really last on twitter (X? what is the consensus on what we are calling it these days?) I'm a dad, a husband, dog and cat owner, points & miles enthusiast (ask me about how I travel)
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@joshualowenthal
Josh Lowenthal
14 days
I’ll challenge anyone to find a place that is better than Northern Michigan during the summer.
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@joshualowenthal
Josh Lowenthal
20 days
Are you looking to grow your Twitter (or any social media following)? Engage with comments when you post! One of my minor pet peeves is someone who just constantly posts content but then never engages with the audience as people try to talk with them and comment on their
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@joshualowenthal
Josh Lowenthal
13 days
Do you know what’s in your Operating Agreement (OA)? Do you have an operating agreement? One common mistake that I see with entrepreneur’s is either not knowing what’s in their OA or having one at all. Each can have dire consequences. Take for example if you don’t know
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@joshualowenthal
Josh Lowenthal
2 months
@the_cat53 There are plenty of contractors that just run their businesses without any legal protection.
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@joshualowenthal
Josh Lowenthal
4 months
@howard_knudsen Oof I'm sorry to hear that. Sounds like you made the right decision! Those EITC and dependent audits weren't always a great look for the IRS. I understand why there was focus there, but at the same time it seemed to me like there was a much better use of resources elsewhere.
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@joshualowenthal
Josh Lowenthal
3 months
One common thread that I've found often get overlooked in M&A is tax due diligence. Most people know the impact of legal due diligence and financial due diligence. But tax due diligence is where the real magic happens. A 🧵
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@joshualowenthal
Josh Lowenthal
5 months
Alright #taxtwitter need your thoughts on a situation. Several irrevocable trusts (up to 11) were established by a family of taxpayers between 2012-2018. From date of establishment to now there has never been a 1041 filed for any of these trusts. Instead all income has been
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@joshualowenthal
Josh Lowenthal
3 months
Most SMBs would benefit from having a tax attorney in their corner. They just don't know it yet.
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@joshualowenthal
Josh Lowenthal
4 months
Regardless of where you are at in your career, 40 years is too long to sit in a cubicle waiting for permission to retire. If you're working for someone right now take a serious look at where you want to be in the next 5, 10, 15 years. Does that make you happy? If not, change it.
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@joshualowenthal
Josh Lowenthal
22 days
@zplerhop She’s got us!
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@joshualowenthal
Josh Lowenthal
8 months
@LoganGrafTax As a tax attorney this is the thing that gets me ALL. THE. TIME. Talking to a taxpayer to scope a resolution issue and before our meeting he says, “he so I haven't filed by taxes for 2018-2020 and have no receipts or copies of my 1099s,” can you give me an idea of what this
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@joshualowenthal
Josh Lowenthal
6 months
Factually correct and 100% misleading. While your capital gains tax rate is 0% for a couple filing MFJ up to $94,000 for 2024, this is also incredibly misleading. That 0% tax bracket is based on you TAXABLE INCOME, I.e, all your income, not just your income from the sale of
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@joshualowenthal
Josh Lowenthal
3 months
The secret to real financial freedom isn't shooting to become the next Unicorn. It's striving to buy a business that generates $500K in Gross Profit every year.
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@joshualowenthal
Josh Lowenthal
6 months
So tried something different this week. Living in a more “rural” area in Alabama we don't get nearly as much good bread as we used to living in other parts of the country. So thought I'd try my hand at sourdough. Definitely have a ways to go, but you need to start somewhere.
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@joshualowenthal
Josh Lowenthal
22 days
@lwgowin @petercnordberg 👆Haha exactly. I honestly can’t engage with these individuals (and if you know me I will talk with a LOT of people). Everyone is entitled to their opinions, even if they are just wrong. And they are just wrong. Where I struggle is how to best approach these situations where
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@joshualowenthal
Josh Lowenthal
1 month
Ever get frustrated when lawyers talk about terms in a deal? Think your lawyer is going to kill your deal? This week i’m sharing with over 200+ SMB owners, searchers, and professionals about reps and warranties (I know, I know, not super exciting but extremely important).
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@joshualowenthal
Josh Lowenthal
4 months
Friends! Who are our SMB/ETA folks in Birmingham, AL?
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@joshualowenthal
Josh Lowenthal
9 months
@Budgetdog_ Out of curiosity, what markets are you seeing irrevocable trusts for a few hundred dollars?
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@joshualowenthal
Josh Lowenthal
13 days
While you should never let the tax tail wag the dog, you absolutely need tax professionals, like Laura, involved in your deal. What might seem as a "simple" mistake by a CPA could lead to a VERY costly cleanup (be it attorney fees or filing fees with the IRS to request a PLR).
@Laura_W_Gieseke
Laura Wilhite Gieseke
13 days
Tuesday Tax tip! If you are planning to make a tax election that affects how your deal is taxed, it is in your best interest to have a tax specialist - whether that's a tax attorney or a CPA who specializes in M&A - take a look at it. Many of these elections have specific
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@joshualowenthal
Josh Lowenthal
2 months
@claywelch Ugh yeah let's not even talk about CA 😭
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@joshualowenthal
Josh Lowenthal
3 months
Absolutely unreal meeting so many great twitter people IRL. Big shoutout to @thesmbrecruiter for pulling together a great meetup.
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@Jer_Car
Jeremy Carter
3 months
Highly recommend meeting Twitter friends IRL. Lot of good energy tonight at the SMB Takeover. Thanks for organizing @thesmbrecruiter
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@joshualowenthal
Josh Lowenthal
3 months
When sending an LOI make sure you know the difference between a 338(h)(10) and a 336(e). If you don't know the difference, consider not including it in your LOI
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@joshualowenthal
Josh Lowenthal
22 days
@SuaSponte2020 Been banging my head against a brick wall all night. This is the stuff that just infuriates me as a lawyer. But also makes me incredibly sad because a lot of these folks slip through the cracks and dupe perfectly innocent people into believing their nonsense
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@joshualowenthal
Josh Lowenthal
3 months
@BSeptak yes, that’s exactly what you should be doing. The tax preparer in question reported each 1099 on its own Sch. C because their tax prep software asked, “Do you want this on a Sch. C?” which they then thought each required its own schedule 🙄
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@joshualowenthal
Josh Lowenthal
3 months
Some handy advice: If your lawyer or your accountant doesn't know the difference between a sole proprietorship and a single member LLC there's a good chance you need a new lawyer or accountant.
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@joshualowenthal
Josh Lowenthal
5 months
@rledbetterCPA Maybe never send anything in Word to the IRS. PDF that stuff!
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@joshualowenthal
Josh Lowenthal
2 months
Don’t confuse busyness with productivity. Being busy shouldn’t be a badge of honor for an entrepreneur, but invariably it is. Instead, we should be encouraging owners to do less through: systems, delegation, 80/20, and focusing in on the important work. This frees up time to
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@joshualowenthal
Josh Lowenthal
1 month
If there’s one thing I’ve learned from owning my own business, it’s that once you call the shots: about the clients you work with, about your schedule, about the tech, and about the business; it makes it a heck of a lot harder of a sell to go back to work for someone else.
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@joshualowenthal
Josh Lowenthal
8 months
Law schools ... normalize launching your own law firm. Walk into any T25 law school today and there is rarely a class on law firm ownership, accounting for law firms, or sales and marketing.
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@joshualowenthal
Josh Lowenthal
4 months
MBAs looking to find one of these 10,000+ boomers/day that are retiring.
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@joshualowenthal
Josh Lowenthal
2 months
Let's talk about QSBS for S Corporations. What? Huh? I thought QSBS is only for C Corporations.... Well technically, you are right, but there are still ways to structure for QSBS in an S Corp. 1/
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@joshualowenthal
Josh Lowenthal
2 months
Colin hits this on the head. Avoid shiny object syndrome and make use of 70-80% of the tools you already have in your stack. I can bet that most use maybe 10-20% of each tool they have in their stack. I’m definitely guilty of this too.
@Clevy_Law
Colin S. Levy
2 months
Make better use of existing tools before turning to new ones. You likely are underutilizing the tools you already have at your disposal.
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@joshualowenthal
Josh Lowenthal
21 days
@LegalFockery Right right, got it. But let's stay on topic for just a moment because my question was just a point of a clarification about lumping satanic demons and "you people" together. You see, I have a bit of a theological issue because I don't really believe in satan or demons.....
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@joshualowenthal
Josh Lowenthal
1 month
Me showing my wife 23 reels that I sent her on Instagram while sitting right next to her on the couch.
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@joshualowenthal
Josh Lowenthal
26 days
@Eli_Albrecht Every. Single. Time. Don't know how it seems to happen, but the second I go on vacation EVERYONE needs something right this moment.
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@joshualowenthal
Josh Lowenthal
2 months
TL;DR: Theres a better way when it comes to F Reorgs for S Corp targets in m&a if the IRS adopts these comments and expands its guidance. Until then use a good tax lawyer. @JoshuaASiegel , @Laura_W_Gieseke , and I often talk about the need to have good tax counsel on deals here
@JoshuaASiegel
Joshua Siegel
2 months
The ABA is asking the IRS to provide guidance that would further streamline certain F Reorganization transactions. Please reach out if you have any questions ⁦ @Albrecht_Law
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@joshualowenthal
Josh Lowenthal
3 months
Every LOI is going to have a tax angle, whether intentional or not. Have a lawyer who understands taxes review before sending your LOI. This will help avoid making you as a buyer look like you don't understand your own deal.
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@joshualowenthal
Josh Lowenthal
3 months
If you can dedicate 8 hours a day to building someone else’s dream, imagine what 2 hours a day can do for launching your own.
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@joshualowenthal
Josh Lowenthal
1 month
@Laura_W_Gieseke but but Laura…..you’re telling me that we SHOULDN’T love S Corps? I elected S years ago and it’s saved me bajillions in taxes 😂🤣😂
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@joshualowenthal
Josh Lowenthal
7 months
@JWellsCFO Could just slap a sales tax on everything….BOOM simplified 🤣
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@joshualowenthal
Josh Lowenthal
2 months
A common saying that gets thrown around in the tax world is: "Don't let the tax tail wag the dog." Taxes are important and play a large role in M&A. However, at economics should always rule at the end of the day. If a deal doesn't make good economic sense, don't pursue it.
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@joshualowenthal
Josh Lowenthal
2 months
@JohnLWheaton1 Yes, I don’t disagree. There are plenty of non-tax benefits to forming an LLC. I’m mainly suggesting that those who do it solely for tax purposes are forming their entity for the wrong reason.
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@joshualowenthal
Josh Lowenthal
3 months
If you want to super-charge your career, business, or relationships, then get together with people in real life. That is where the magic happens.
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@joshualowenthal
Josh Lowenthal
4 months
Alright so I full well recognize that I am posting this one of the two social medias, however I am curious: What is the better platform to build a law firm? What is your reasoning?
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@joshualowenthal
Josh Lowenthal
22 days
@suetheob I’m sure there’s a few who definitely would too. It’s the promoters that are the biggest issues imo. Because they fool innocent people into believing this nonsense.
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@joshualowenthal
Josh Lowenthal
1 month
Have you ever talked to someone about putting real estate in an S Corp? Today I am talking to my subscribers about the risks of using S Corps for real estate investing (hint: they aren't worth it) Check it out in my newsletter: Empire Builders which goes out today at 4:00pm CT
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@joshualowenthal
Josh Lowenthal
2 months
If you liked this post, you might also enjoy my *mostly* weekly newsletter: Empire Builders. You can check it out here ➡️
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@joshualowenthal
Josh Lowenthal
3 months
Invest in good coffee and good coffee making gear. It will change you're morning routine.
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@joshualowenthal
Josh Lowenthal
4 months
There's something uniquely satisfying about finishing yard work; especially as a professional service provider where 99% of my work just never seems to end.
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@joshualowenthal
Josh Lowenthal
3 months
Entrepreneurs love their LLCs and frankly so do I. But not everything needs to be it's own LLC off the bat. Just like you shouldn't be talking about "HoldCos" until you buy your first business. Sometimes you don't need an entity until you make money.
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@joshualowenthal
Josh Lowenthal
2 months
Estate planning is NOT Elder law.
@jennyrozelle
Jenny Rozelle
2 months
I just left a meeting involving 4 attorneys (5 including me) + our Medicaid paralegal, where we discussed the changes to Indiana's Medicaid rules. It reminded me to say this: Not all estate attorneys are elder law attorneys! If Medicaid (for home health care or long-term care)
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@joshualowenthal
Josh Lowenthal
4 years
The countdown is over! I would like to announce my newest venture! After months of preparation, I am ready to help you! As a business, tax, and estate planning attorney, my priority is my clients. Connect today to get started!
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@joshualowenthal
Josh Lowenthal
21 days
@LegalFockery So just so that I am clear, are the satanic demons different from “you people” or are they the same?
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@joshualowenthal
Josh Lowenthal
22 days
@Ptwarg When you figure it out can you let me know? 😂
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@joshualowenthal
Josh Lowenthal
6 months
Starting M&A negotiations? While price sparks the conversation, the real game-changer is transaction structure. Assets or stock? The choice has major legal and tax implications. A 🧵
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@joshualowenthal
Josh Lowenthal
3 months
Professional service providers, whatever you’re charging right now, chances are you’re too cheap. Take your fee and double it.
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