A lot of advisors lead with the word "fiduciary." Corwin Davidson is more interested in what happens after that word is said. If an advisor claims to act in a client's best interest but has no access to real tax strategy, Corwin believes the promise is incomplete.
In this episode of Fiduciary Alchemy, Craig Andrews talks with Corwin Davidson, Wealth Advisor and Tax Strategy Nerd at Breakline Wealth + Tax, about the places where wealth planning and tax planning collide. They get into RMDs, Roth conversion strategies, high W-2 income, Social Security taxation, fee transparency, and why asking better questions may matter more than accepting industry labels.
The sharpest part of the conversation is around business exits. Corwin explains why selling a business may become the largest tax event of an owner's life, and why waiting until the deal is already on the table can leave too few options. Trust structures, 1031 exchanges, qualified opportunity zones, and charitable strategies may each play a role, but the real work is in layering them early enough to create liquidity, deferral, and possible tax elimination.
Craig and Corwin also talk about life after the sale. Money may solve the balance sheet, but it does not automatically create purpose on Wednesday morning after the business is gone. That makes exit planning bigger than valuation, bigger than tax, and bigger than the transaction itself.
Want to learn more about Corwin Davidson's work? Visit Breakline Wealth + Tax at https://breaklinewealthandtax.com/.
Connect with Corwin on LinkedIn at https://www.linkedin.com/in/corwindavidson.
Think you'd be a great guest on the show? Apply at https://fiduciaryalchemy.com/podcast/apply/.
Want to learn more about Craig Andrews' work? Check out https://fiduciaryalchemy.com/.
Key Points
[1:00] Craig introduces Corwin Davidson as a wealth advisor and tax strategy doctor with Breakline Wealth + Tax.
[2:26] Corwin explains how the tax strategy doctor brand came from Craig’s mastermind group and why it worked better than tax strategy nerd.
[4:13] Corwin describes wearing the lab coat at an event and how it made him stand out in a crowded advisor market.
[4:53] Corwin challenges the easy use of the word fiduciary and asks whether advisors without tax strategy access can fully live up to that promise.
[8:16] Corwin explains why fee transparency and clear product recommendations matter when clients ask how advisors are paid.
[10:28] Corwin defines required minimum distributions and why RMDs can turn retirement accounts into taxable income events.
[12:25] Corwin explains why high W-2 earners and business owners both need tax strategy, not just investment management.
[14:57] Craig and Corwin discuss Social Security taxation, retirement income, and why many people want purpose and activity after traditional retirement.
[18:22] Corwin explains why business owners need to know what Wednesday looks like after a sale, because money alone does not create purpose.
[21:29] Corwin frames the sale of a business as potentially the largest tax event of an owner’s life.
[22:56] Corwin explains qualified opportunity zones and why tax strategy may depend on patience with capital.
[24:16] Corwin describes stacking tax strategies such as trust structures, 1031 exchanges, qualified opportunity zones, and charitable strategies.
[27:56] Corwin recommends one to three years of tax and exit planning before a business sale, with three to five years as the broader sweet spot.
[30:14] Craig closes on the core lesson: how much you pay in tax is a choice, but the choice has to start before the deal table.
Episode Transcript
Speakers: Craig Andrews, Corwin Davidson, Compliance Choir
[0:00] Craig Andrews: You never know how much time you have.
[0:02] Craig Andrews: For me, that stopped being an idea and became reality on August 22nd, 2021.
[0:09] Craig Andrews: The doctors put me on a ventilator and told my wife to call hospice so she could prepare
[0:14] Craig Andrews: for the day they planned to pull the plug.
[0:17] Craig Andrews: Six weeks later, I woke up to an entirely different reality.
[0:20] Craig Andrews: I could not walk, I could not talk, I could not even lift my own arm, and I woke up realizing
[0:26] Craig Andrews: something else, I had not made the right preparations for my family.
[0:30] Craig Andrews: The plans I thought were pretty good fell through when it mattered most.
[0:34] Craig Andrews: That is why fiduciary alchemy welcomes voices that would have warned me about the holes
[0:39] Craig Andrews: in my plans.
[0:40] Craig Andrews: My hope is that you live a long and prosperous life, but I also hope you make better plans
[0:45] Craig Andrews: than I did.
[0:46] Craig Andrews: So tune in, take notes, and stay with us through the end when bluesman grindle and the compliance
[0:51] Craig Andrews: choir.
[0:52] Craig Andrews: Bring a word of caution.
[1:00] Craig Andrews: Today I want to welcome Corwin Davidson.
[1:02] Craig Andrews: He is a wealth advisor and tax strategy doctor.
[1:07] Craig Andrews: Yes, you heard that right, a tax strategy doctor with break-line wealth and tax.
[1:12] Craig Andrews: He helps high income and high net worth clients align investments, tax strategy, and long-term
[1:18] Craig Andrews: financial decisions.
[1:21] Craig Andrews: Today he is wearing a lab coat because guess what, helps a lot of people in the medical
[1:25] Craig Andrews: field, but not just them.
[1:26] Craig Andrews: Really, it is any high earner who needs complex tax strategies to pay as little in tax because
[1:35] Craig Andrews: he says how much you pay in tax is a choice.
[1:39] Craig Andrews: Corwin, welcome.
[1:42] Corwin Davidson: Thank you, Craig.
[1:43] Corwin Davidson: Thank you.
[1:44] Corwin Davidson: It is great to see you, man.
[1:45] Corwin Davidson: It is good to see you.
[1:46] Craig Andrews: We should tell folks we know each other, we have a little mastermind group that we formed
[1:53] Craig Andrews: amongst ourselves.
[1:54] Craig Andrews: We do.
[1:55] Craig Andrews: So you are not some stranger, good friend, and the resident doctor?
[2:02] Corwin Davidson: Yes, the resident doctor, it is exciting, it is awesome to get on a guest on your podcast,
[2:09] Corwin Davidson: Craig.
[2:10] Craig Andrews: No, I have been looking forward to it, I have been looking forward to it.
[2:17] Craig Andrews: Why don't we start with this?
[2:18] Craig Andrews: Because this is something that happened in the mastermind group, how did the whole origin
[2:23] Craig Andrews: of the tax strategy doctor?
[2:26] Corwin Davidson: Yes, that was a really good, because I am in the processor, I was in the process at that
[2:34] Corwin Davidson: point of branding myself, and I brought it to the mastermind group, and I am a nerd
[2:42] Corwin Davidson: for tax strategy.
[2:44] Corwin Davidson: And so I brought it to the mastermind group, like, "Hey, guys, I'm going to brand myself
[2:48] Corwin Davidson: as the tax strategy nerd," and lo and behold, it was just like, "No, no, no, no.
[2:56] Corwin Davidson: Like how about you not do that?"
[2:58] Corwin Davidson: And think about tax strategy doctor, a more authoritative designation or branding for what
[3:09] Corwin Davidson: you do, and yeah, and it fit really well, and it got me here with the lab coat, right?
[3:15] Craig Andrews: Yeah, when you went to an event recently wearing a lab coat, which was kind of, that was a
[3:21] Craig Andrews: bold move, that was a little scary.
[3:23] Corwin Davidson: It was, it took some reinforcement from the mastermind group, and some outside folks,
[3:30] Corwin Davidson: one of the guys that I was going to sponsor that event with.
[3:35] Corwin Davidson: And so yeah, checked in with the mastermind group, and it was like, "Yes, full go, let's
[3:40] Corwin Davidson: do this," and so get over your own ego, Corwin, put on the physician's coat, and what a success.
[3:50] Corwin Davidson: You know, stuck out in that event, you know, stuck out in that event in the most positive
[3:56] Corwin Davidson: of ways.
[3:57] Corwin Davidson: You know, everybody came up wanting to talk to me, you know, saying, "Hey, you're obviously
[4:04] Corwin Davidson: a doctor," so like, you know, "What do you do?"
[4:07] Corwin Davidson: And so yeah, it was awesome results, and you know, it was great.
[4:13] Craig Andrews: Well, you know, one of the challenges in your field is there's 450,000 financial advisors
[4:22] Craig Andrews: in the US, and you all do, at a high level, you all do the same thing.
[4:27] Craig Andrews: And I see it as a marketer.
[4:30] Craig Andrews: I mean, one, I'm thankful because I help market in that field.
[4:33] Craig Andrews: I'm thankful that everybody says, "Oh, we're different, we're fiduciaries," or something
[4:40] Craig Andrews: like that.
[4:41] Craig Andrews: Like, nobody can tell the difference between you all, and I love the choice that you made
[4:46] Craig Andrews: because it really helps you stand out, helps make you memorable.
[4:51] Corwin Davidson: Yeah, no, I appreciate that.
[4:53] Corwin Davidson: And you know, in this space, you know, fiduciaries, one of my most critiqued words, you know, because
[5:03] Corwin Davidson: it really takes the essence of, you know, the way it's written, you know, Reg B, Reg BI,
[5:12] Corwin Davidson: and you know, what it says is, you know, act in every action and every thought process,
[5:17] Corwin Davidson: act in the best interest of the client.
[5:19] Corwin Davidson: And you know, one of the things that separates us is this tax strategy piece, but the vast
[5:28] Corwin Davidson: majority of the investment advisors, they don't have access to the tax strategy part.
[5:33] Corwin Davidson: And so, are they actually fiduciaries?
[5:35] Corwin Davidson: Is one of the big things that I fight with a lot, you know, when folks are, you know,
[5:40] Corwin Davidson: I constantly get asked, "Are you a fiduciary?"
[5:42] Corwin Davidson: And it just, it sets me down this path.
[5:45] Corwin Davidson: Yeah.
[5:46] Craig Andrews: Well, I first encountered this back in 2016 when I was working with a client.
[5:53] Craig Andrews: And you know, they wanted to promote, now, the main sales guy in the account came from,
[5:58] Craig Andrews: I'm not going to say their name, but you've seen the little graphic I made mocking.
[6:01] Craig Andrews: I call it King Fisherman Investments.
[6:03] Craig Andrews: I got you.
[6:04] Craig Andrews: You know, for different, we're fiduciaries.
[6:06] Craig Andrews: And but he came from that organization and he really wanted to put on the website, we're
[6:12] Craig Andrews: a fiduciary.
[6:13] Craig Andrews: And we kept writing in the compliance, you know, and complaining, "You can't say that.
[6:16] Craig Andrews: You can't say that."
[6:19] Craig Andrews: And she smugly threw an 80-page document at me and said, "You need to read this."
[6:24] Craig Andrews: And thinking it was just, "I'd never read it by a Reddit," and I came back and I asked
[6:29] Craig Andrews: her, I said, "If I quote the SEC Chairman, would that be compliant?"
[6:35] Craig Andrews: And she said, and she kind of paused thinking it was a trick question.
[6:38] Craig Andrews: And she's like, "No, that would be compliant."
[6:41] Craig Andrews: Well, right there in that SEC document, the Chairman of the SEC said, "In some A-words,
[6:47] Craig Andrews: the term fiduciary is meaningless because it's defined so broadly.
[6:51] Craig Andrews: You know, the way I put it, these are my words, these are not his words, compliance don't
[6:56] Craig Andrews: get upset with me.
[6:57] Craig Andrews: I'm just claiming these are my words."
[6:59] Craig Andrews: It was written so broadly, you could drive a bus through it.
[7:03] Craig Andrews: And I had the SEC Chairman saying that, so we actually put an exact quote of that on the
[7:07] Craig Andrews: website and said, "But here's how we do it."
[7:11] Craig Andrews: And I think that's something everybody needs to think about.
[7:14] Craig Andrews: They get hung up on this term fiduciary.
[7:17] Craig Andrews: It's a meaningless term, and that's not my opinion.
[7:20] Craig Andrews: That's what the Chairman of the SEC said.
[7:22] Corwin Davidson: Yeah, I agree with you there.
[7:25] Corwin Davidson: Again, getting asked that question so frequently, I usually start the answer to that with, "Alright,
[7:33] Corwin Davidson: so this is my favorite and least favorite question at the same time, and go through,
[7:41] Corwin Davidson: what does that actually mean to you?"
[7:42] Corwin Davidson: And I think it's important from an advisor's standpoint to have a firm-wide definition.
[7:50] Corwin Davidson: What does this mean to our firm as opposed to what is being put out in regulation?
[7:56] Craig Andrews: Yeah, and that's exactly what we did.
[7:59] Craig Andrews: We say, "Here's what the Chairman of the SEC said, here's how we put it in practice."
[8:02] Craig Andrews: And I think that's the question everybody needs to ask, "How do you handle that?"
[8:06] Craig Andrews: If somebody wants to buy an insurance product that has a commission, how do you handle it?
[8:13] Craig Andrews: And let me just ask, how do you handle that?
[8:15] Corwin Davidson: Oh, yeah, so I mean, full transparency with fees is really important, and so a lot of
[8:24] Corwin Davidson: our clients will ask us, especially at the outset, and even in our presentation, our
[8:28] Corwin Davidson: initial proposal presentation, this is how we get paid, this is what it looks like specifically
[8:35] Corwin Davidson: for you as we've gone through and detailed everything that you've told us, to everything
[8:41] Corwin Davidson: that you've sent over in documentation as we put this proposal together, but I think
[8:45] Corwin Davidson: transparency in fees is really the best policy.
[8:49] Craig Andrews: Yeah.
[8:50] Craig Andrews: Yeah.
[8:51] Craig Andrews: Yeah.
[8:52] Craig Andrews: And I think almost any situation of importance, you just kind of ask questions, and boldly
[9:03] Craig Andrews: ask questions of whoever you're working with, whether it's your doctor or your tax strategy
[9:08] Craig Andrews: doctor.
[9:10] Corwin Davidson: I completely agree.
[9:11] Corwin Davidson: Well, that and the part of not every product is blanket should be recommended across the
[9:21] Corwin Davidson: spectrum of clients.
[9:22] Corwin Davidson: And so really having a detailed approach to discovery, to data collection, and to initial
[9:30] Corwin Davidson: proposal build, to make sure that there's nothing in a plan that doesn't link specifically
[9:36] Corwin Davidson: back to a goal or objective, whether that be short term or long term.
[9:43] Craig Andrews: Yeah.
[9:45] Craig Andrews: So let's talk a little bit about the, let's talk a little bit about the tax strategy.
[9:51] Craig Andrews: Yeah.
[9:53] Craig Andrews: And yeah, so I see a lot of, I see a lot of firms that don't have a strong tax component.
[10:02] Craig Andrews: They pull in someone, we had a prior guest that at one point, he decided to start doing
[10:11] Craig Andrews: taxes for his clients.
[10:13] Craig Andrews: He brought in CPAs because he kept bumping into CPAs that were given his clients bad advice,
[10:21] Craig Andrews: you know, tied to RMDs.
[10:24] Craig Andrews: First off, what are RMDs and why would, you know, why would that confuse CPAs?
[10:28] Corwin Davidson: Well, RMDs are required minimum distributions, they happen in retirement accounts, not including
[10:35] Corwin Davidson: Roth accounts, but they happen in, you know, tax deferred retirement accounts, starting
[10:39] Corwin Davidson: at age 73.
[10:41] Corwin Davidson: And so the reason tax strategy comes into, into that conversation is because once the
[10:48] Corwin Davidson: IRS starts forcing money out of these tax deferred retirement accounts, they, those dollars
[10:55] Corwin Davidson: they get forced out of the accounts show up as earned income to those, to those account
[11:02] Corwin Davidson: owners in the year that they receive them.
[11:04] Corwin Davidson: And so the older you get, the more the IRS forces out.
[11:09] Corwin Davidson: And so it's essential to make sure that once those RMDs start happening, especially if,
[11:15] Corwin Davidson: you know, the retirement accounts haven't been utilized, you know, maybe the client has
[11:21] Corwin Davidson: had a ton of outside assets and was just saving the retirement accounts for inheritance.
[11:27] Corwin Davidson: But once you get to that RMD age, they start kicking these, you know, income taxor, this
[11:33] Corwin Davidson: income out that is followed by taxes.
[11:36] Corwin Davidson: And it's something that you should as a, you know, as an advisor be able to control whether
[11:41] Corwin Davidson: that be between, you know, the between the relationship of the CPA or the, and the advisor,
[11:46] Corwin Davidson: or you know, be awesome if the advisors got tax strategy in house.
[11:52] Corwin Davidson: Yeah.
[11:53] Corwin Davidson: What, what are some of the complex issues?
[12:01] Corwin Davidson: So I know, you know, I know you specialize in, in higher net, you know, higher income
[12:08] Corwin Davidson: professions.
[12:09] Corwin Davidson: Yeah.
[12:10] Corwin Davidson: You know, like, you know, some medicals, one, you mentioned construction.
[12:15] Corwin Davidson: What are some of the unique challenges that those folks run into because in terms of not
[12:20] Corwin Davidson: only their wealth strategy, but their tax strategy?
[12:24] Corwin Davidson: Yeah.
[12:25] Corwin Davidson: So I'm going to give you both a couple of sides of it.
[12:28] Corwin Davidson: So, you know, from the high W two earner, and this is something, you know, when we, when
[12:34] Corwin Davidson: we think about the tax code, the tax code in our team's opinion was not designed to
[12:39] Corwin Davidson: generate revenue.
[12:40] Corwin Davidson: It was designed to control investor behavior.
[12:44] Corwin Davidson: And a lot of people think that that's a, you know, it really suits the business owner
[12:48] Corwin Davidson: most.
[12:50] Corwin Davidson: And it's simply not true.
[12:52] Corwin Davidson: The tax strategy is for both W two employees and business owners, whatever structure they
[12:57] Corwin Davidson: run for their business.
[12:59] Corwin Davidson: But particularly W two income is without tax strategy for high earners is basically a
[13:07] Corwin Davidson: goldmine for the IRS and most W two earners don't understand that there are options available
[13:14] Corwin Davidson: to, you know, place money in this, you know, in this area or this area of the economy and
[13:21] Corwin Davidson: get tax breaks for it, reduce income and reduce taxes on the other side of that.
[13:26] Corwin Davidson: And we'll just take kind of a one off position of somebody who, you know, a business owner
[13:33] Corwin Davidson: and employee who's done an amazing job at funding tax deferred retirement accounts.
[13:39] Corwin Davidson: And now they're looking at this, you know, huge piece of their wealth that every time
[13:44] Corwin Davidson: they take a dollar out, it creates attacks.
[13:47] Corwin Davidson: And so using strategies like a discounted Roth conversion to be able to place money in
[13:54] Corwin Davidson: an area where the IRS is designated for, you know, for a tax deduction and actually convert
[14:00] Corwin Davidson: at a discounted value from an IRA to a Roth IRA and ultimately pay less tax through that
[14:07] Corwin Davidson: conversion.
[14:08] Corwin Davidson: Yeah.
[14:09] Corwin Davidson: And there's plenty more areas that, you know, we could get into, but high level, those
[14:15] Corwin Davidson: are two really impactful pieces that I think on the W two employee side that just a lot
[14:21] Corwin Davidson: of people don't know is available to them.
[14:24] Corwin Davidson: And on the side of highly accumulated wealth in retirement accounts, there is a relief
[14:31] Corwin Davidson: valve available.
[14:33] Craig Andrews: Yeah.
[14:34] Craig Andrews: And so some things I've heard is if, if your RMDs, you know, your acquired minimum distributions
[14:42] Craig Andrews: are high.
[14:43] Craig Andrews: Yeah.
[14:44] Craig Andrews: If you're counting on social security at all, and that most high earners probably aren't,
[14:49] Craig Andrews: but if you are, I've heard social security gets taxed at like some insane rate.
[14:55] Corwin Davidson: Yeah.
[14:56] Corwin Davidson: Yeah.
[14:57] Corwin Davidson: And this administration actually tried to ease that for social security earners.
[15:04] Corwin Davidson: But in general, if you're making more than I believe, you know, 18,000, 18,500 dollars
[15:10] Corwin Davidson: once you go on social security, the moment you go over that threshold, 85% of your social
[15:16] Corwin Davidson: security becomes taxable. And so it's really important, especially now, because there's
[15:22] Corwin Davidson: a, there's really a trend over the last 10 years where, you know, folks are understanding
[15:28] Corwin Davidson: that retirement, you know, American retirement, you know, live off your assets and, you know,
[15:34] Corwin Davidson: don't do anything anymore. You know, I've finished my work and career. That program doesn't necessarily
[15:41] Corwin Davidson: work for the vast majority of people now. And they're wanting to stay active. They want
[15:46] Corwin Davidson: to stay with their groups. They want to continue, you know, if they're, you know, had the, you
[15:51] Corwin Davidson: know, occupations where they worked with their brain, work part time, be involved in philanthropy.
[15:58] Corwin Davidson: But you know, staying active in your older years is really popular now. And in a lot of
[16:04] Corwin Davidson: cases, you know, people want to generate an income off of the time they spend doing that.
[16:09] Corwin Davidson: And so making sure that one, you know, the rules, but two, that there are assets outside
[16:16] Corwin Davidson: of the social security system that you are, you know, either supplementing, or, you know,
[16:22] Corwin Davidson: in best case, yeah, you know, that's where the vast majority of your retirement income
[16:27] Corwin Davidson: comes from, would be, you know, would be really advantageous in this kind of new realm of retirement.
[16:34] Craig Andrews: Well, I had somebody put it to me one way, they said, you know, during your working years,
[16:40] Craig Andrews: you know, the highest spend day of the week is Saturday. You spend more money on Saturday
[16:45] Craig Andrews: than any other day of the week during your working years. During your retirement years,
[16:50] Craig Andrews: every day is Saturday. Yes. And there's this mindset that, hey, when I'm retiring, my costs
[16:59] Craig Andrews: will go down and in reality, people end up spending more in retirement because every day is Saturday.
[17:04] Corwin Davidson: And that's actually there's a there's a there's a model or a trend model on that where that
[17:12] Corwin Davidson: lasts for about the first three years, you know, somebody, you know, a couple goes into retirement,
[17:17] Corwin Davidson: and you see this kind of like sweeping bell curve before it comes back down of figuring out how to
[17:25] Corwin Davidson: exist seven days a week without, you know, without an occupation. And for me, like in inside of me,
[17:34] Corwin Davidson: I believe purpose is one of the most amazing things a human can have, you know, whether that's
[17:40] Corwin Davidson: purpose and working purpose and giving back purpose in spending time with the family,
[17:46] Corwin Davidson: whatever that looks like hobbies, woodworking, making sure that you've got a purpose in every day
[17:54] Corwin Davidson: so that you get out of bed, and you've got a drive to go with not necessarily achieve something,
[17:59] Corwin Davidson: but achieve something for that day. Yeah. It is so important to really longevity.
[18:05] Craig Andrews: Yeah. Well, I keep hearing stories about people who retire and then die in a few years.
[18:11] Craig Andrews: And and I think unfortunate. I think it's what you're talking about. It's not that their bodies
[18:17] Craig Andrews: wore out. It's that they, I think what you're saying is they lost their purpose. Yeah. And so,
[18:22] Corwin Davidson: you know, we talk with, you know, we work with a lot of business owners and some of the business
[18:26] Corwin Davidson: owners we work with, they're like, hey, I want to sell my company. The first thing, the first
[18:31] Corwin Davidson: question I'm going to ask him is, all right, you sell it tomorrow for the amount of money that
[18:35] Corwin Davidson: you want for it. What does Wednesday look like? Like, what does two days from now look like when
[18:41] Corwin Davidson: you wake up, what are you going to do? And most of the time, they can't answer that question.
[18:47] Corwin Davidson: They've never experienced what that looks like. And so, you know, in one case, you know, a couple
[18:53] Corwin Davidson: of years back, gentlemen actually answered the question, he said, hey, you know, I've always loved
[18:58] Corwin Davidson: woodworking. I was like, have you ever done it? He said, no, I was like, well, you've got the means
[19:03] Corwin Davidson: and you've got the shop. I was like, go, you know, go get what woodworking tools that you would,
[19:08] Corwin Davidson: you would want to have to be able to do what you want to do with woodworking. And, and let's come
[19:14] Corwin Davidson: back six months from now and let's see how things are going. So we meet back up six months from then.
[19:19] Corwin Davidson: And I was like, so how's woodworking is like, I hate woodworking.
[19:22] Corwin Davidson: I was like, all right. But the concept still rains true is, you know, if you find out you don't
[19:29] Corwin Davidson: like woodworking, so you're woodworking tools. And what's next? Yeah, I was hoping you were going
[19:35] Craig Andrews: to say he loves woodworking, because I have some antique molding planes I'm trying to get rid of.
[19:41] Craig Andrews: And they, I've only used them as decoration. I've never used them for real work. But for,
[19:46] Craig Andrews: but they're like extremely scarce. And there's a part of me that can't throw them away. Yeah,
[19:52] Craig Andrews: for historical reasons. But no, that I mean, that makes so much sense. And I don't know. I mean,
[20:03] Craig Andrews: for me, I don't know what retirement's going to look like. I, I don't, I don't, I don't see myself
[20:11] Craig Andrews: as a retiring type. And I hear, you know, Karen and I've made some friends here in, in Bastrop,
[20:18] Craig Andrews: where he was, he was the executive chef at Apple. The dude has prepared meals for Steve Jobs. Yeah.
[20:28] Craig Andrews: And, which I figure was kind of like feeding the king, you know, you feed the king something you
[20:33] Craig Andrews: don't like off with your head. And, but he, he obviously did very well and he retired.
[20:40] Craig Andrews: And then he got bored. So he got a job as executive chef at UT. They retired from that. They got
[20:48] Craig Andrews: bored again. And, and, you know, he discovered that retirement, you know, he needs to do something.
[20:55] Corwin Davidson: Yeah, he has the means to do nothing, but he has the need to do something.
[21:00] Corwin Davidson: And that's one of the big pieces of especially business owners in that exit phase is it doesn't
[21:09] Corwin Davidson: matter if you sell it for exactly the amount of money you need or 10 times that amount of money.
[21:16] Corwin Davidson: Money is not going to fill your time. Money is not going to give you purpose. You have to have,
[21:21] Corwin Davidson: that has to come from the heart. That has to come from desire. Yeah.
[21:25] Craig Andrews: Well, let's talk a little bit about when somebody sells a business because if somebody's built up
[21:33] Craig Andrews: a business and they sell it, this is about to be their biggest tax event in their life. Hopefully.
[21:37] Craig Andrews: And it's easy to feel like, well, hey, if I sell for 10 million, you know, the IRS is going to take
[21:47] Craig Andrews: four or five or whatever they're going to take. Yeah. Is that true? That is true. That's about
[21:54] Corwin Davidson: and depending on, you know, especially depending on how you sell it and what state you sell it in
[22:00] Corwin Davidson: will differ pretty tremendously. But in the state of California, I think you can get up to a 52
[22:10] Corwin Davidson: or a 54% effective tax rate selling a business, you know, selling a business for cash.
[22:17] Corwin Davidson: And, you know, there are a lot of opportunities available to the business owner. Now, this isn't
[22:24] Corwin Davidson: something where you sell the business in, you know, December 1st of any given year and try to go
[22:29] Corwin Davidson: figure out the tax strategy or the tax plan, you know, after you sell the business, this is
[22:34] Corwin Davidson: definitely going to need, you know, pre-planning. But there are strategies available to pay, you know,
[22:43] Corwin Davidson: really as much of the tax as you want, depending on how patient you can be with capital.
[22:48] Craig Andrews: Okay. All right. What's that mean? That I got, yeah, I got you. And so
[22:56] Corwin Davidson: between trust structures between 1031 exchange, charitable donations, there are particular tax
[23:08] Corwin Davidson: strategies that lock money up for specific periods of time. Let's talk about qualified
[23:13] Corwin Davidson: opportunity zones for a second. So you move, you move the assets, you know, that's now cash from
[23:20] Corwin Davidson: your sale of your business into a qualified opportunity zone investment. Well, if you hold
[23:26] Corwin Davidson: that investment for 10 years, all of the taxes are forgiven. Huh, but you got to hold the, you got
[23:33] Corwin Davidson: to hold the investment for 10 years. And so what we typically see is that there's not a silver bullet,
[23:39] Corwin Davidson: you know, a single silver bullet for tax strategy. We're really layering different tax strategies
[23:46] Corwin Davidson: on top of each other to make sure that maybe half of, you know, depending on what the, you know,
[23:51] Corwin Davidson: depending on what the monetary value of the sale is and how much of that you need immediately
[23:59] Corwin Davidson: will really dictate what we're doing in terms of layering tax strategies. But between trust
[24:04] Corwin Davidson: structures 1031 qualified opportunity zones and charitable, charitable donation strategies,
[24:11] Corwin Davidson: you know, we can provide not only liquidity and access, but long term tax deferral, long term tax
[24:20] Craig Andrews: elimination through this stacking of tax strategies. And so let me ask a question just listening to
[24:28] Craig Andrews: what you're saying. And, you know, and for the sake of compliance, you know, none of this is
[24:34] Craig Andrews: legal or tax advice. This is just educational. Yes, but what you just talked about with that
[24:40] Craig Andrews: opportunity zone. So let me go back to my example. If I'm selling a business and I sell it for 10
[24:45] Craig Andrews: million dollars, you know, I was on the hook for, let's say, 4 million in taxes. But instead,
[24:53] Craig Andrews: I decide to take 5 million of the 10 and put it in one of these opportunities zones. And I say,
[25:00] Craig Andrews: you know what, I'm going to take whatever the post tax of the remaining 5 million
[25:07] Craig Andrews: and live off that for the next 10 years, then I get 10 years out. That remaining 5 million is
[25:15] Corwin Davidson: potentially untaxed. Correct. And then even in the 5 million that you keep using a 1031 strategy,
[25:26] Corwin Davidson: if that's available based on the sale that you make, using a 1031 strategy to generate an income
[25:33] Corwin Davidson: off of a portion of that 5 million so that you can kick the big tax down the road indefinitely
[25:40] Corwin Davidson: inside of that investment. And it's still kicking off an income where you're paying a smaller tax,
[25:48] Corwin Davidson: but the principal hasn't been taxed yet. And then so maybe you do 2 and 1/2 million for, you know,
[25:53] Corwin Davidson: just taking numbers and splitting them in half here. And on the initial run, we're going to take
[26:01] Corwin Davidson: 2 and 1/2 million of that $10 million sale and pay taxes on it. And so then what we've done is
[26:10] Corwin Davidson: essentially, we've paid a quarter of the tax that was due on the 10 million. And we've deferred,
[26:17] Corwin Davidson: we've deferred the tax. And in the opportunity zone, we've deferred it to a possible tax free
[26:26] Corwin Davidson: after that 10 year period on 7 and 1/2 million of the 10 million dollars worth of taxes.
[26:34] Craig Andrews: Wow. Yeah. Okay. Now, tell me about this opportunity zone again. What is an opportunity zone,
[26:40] Corwin Davidson: what would an investment that look like? Yeah. So there are several different investments
[26:46] Corwin Davidson: inside of Opportunity Zones. Opportunity Zones are federally designated areas in the country
[26:52] Corwin Davidson: that are ripe for development, that the US wants to see development in those areas. And so what
[27:00] Corwin Davidson: they do, and usually it's based off a zip code. And so what you do is you'd find an opportunity
[27:05] Corwin Davidson: zone or an investment inside of an Opportunity Zone and several different, you know, investment
[27:11] Corwin Davidson: firms, private equity firms have these investments. But what they're doing, whether it's real estate,
[27:18] Corwin Davidson: whether it's, you know, one of them, one of them that we really like is Wyoming Reserve.
[27:23] Corwin Davidson: They're the third largest precious metals vault in the world. They just so happen to be located
[27:29] Corwin Davidson: in an Opportunity Zone. And so there's a lot of different types of investments, but as long as
[27:34] Corwin Davidson: they are domiciled in an Opportunity Zone, they get to take advantage of this portion of the tax code.
[27:40] Craig Andrews: So if I'm selling my business, how long does it take to plan to put, you're already said,
[27:46] Craig Andrews: don't start the planning after the sale, start the planning before the sale. Yeah.
[27:51] Craig Andrews: How long does it take to do this planning?
[27:56] Corwin Davidson: One to three years, depending on how complex it's going to be. You know, and I'm a big advocate
[28:03] Corwin Davidson: of exit planning as well, like get ahead of your exit on your business and make sure that you
[28:09] Corwin Davidson: create transferable value, you know, and know that you've got it. And so that's like one piece of it.
[28:15] Corwin Davidson: But along with the exit plan comes the tax plan. If you know you're going to sell a business
[28:19] Corwin Davidson: for 10 million bucks, you then know you're going to have a tax problem. And so creating your exit plan
[28:28] Corwin Davidson: and your tax plan for that exit, I think those two go hand in hand.
[28:34] Craig Andrews: Yeah. Yeah. And I just, you know, I keep hearing stories about people that decide to sell their
[28:41] Craig Andrews: business, somebody made them an offer. And they're like, sure, I'll take that. And then they hope
[28:46] Craig Andrews: that they can put everything together in the two or three months before the business closes.
[28:51] Corwin Davidson: Yeah. And that can be, you know, it can be totally doable. It can be very stressful.
[28:58] Corwin Davidson: And in the, you know, short term planning, and that's why we talk about this, you know,
[29:03] Corwin Davidson: for exit planning, that three to five year sweet spot of get ahead of it,
[29:08] Corwin Davidson: is because, you know, get a professional in there and make sure that, you know, when it comes to
[29:14] Corwin Davidson: value drivers for businesses, you know, delivering transferable value, that you got all your ducks
[29:20] Corwin Davidson: in a row and that your business will sell at or at multiples of what you think it's worth.
[29:26] Craig Andrews: Yeah. Well, we've talked about a lot of specifics here. And so I just, again, you know,
[29:32] Craig Andrews: we won't emphasize, you know, we got a cool song. If you're listening, listen to, to the end,
[29:37] Craig Andrews: it's called the compliance blues. It's a cool song. But one of the things that say, you know, we,
[29:42] Craig Andrews: none of this is tax legal or financial advice. This is just kind of educational. And anybody
[29:49] Craig Andrews: who's listening should, you know, seek a professional and, and get, you know, qualified advice. So I
[29:59] Craig Andrews: just, just saying that for the record. But this is, this is fascinating. I mean, it's,
[30:07] Craig Andrews: for me, it helps me see some of the, you know, some of the pathways to, you know, one, how
[30:14] Craig Andrews: complicated next it can be. But it reminds me of something you said, you said how much you pay in
[30:20] Craig Andrews: tax is a choice. And you have to start making that choice sooner rather than later. Yeah.
[30:28] Craig Andrews: To get the desired result and, you know, to your point, every case is different.
[30:35] Craig Andrews: Every, you know, in a lot of cases, every state is different. And so making sure that
[30:40] Craig Andrews: what you believe to be true is true is the best path forward. And if you're right, awesome. It's,
[30:48] Craig Andrews: you know, the planning fees will be less. But if you're wrong, you don't want to find up,
[30:53] Craig Andrews: find out at the deal table. Yeah. Well, Corin, you're, you're a fount of knowledge.
[31:01] Corwin Davidson: How can people reach you? Find me on LinkedIn, find us online, break line wealth and tax.
[31:08] Corwin Davidson: Those are probably the two best ways to get ahold of us.
[31:13] Craig Andrews: Excellent. Well, thanks for coming on fiduciary alchemy. Yeah. Thanks for having me, Craig.
[31:18] Craig Andrews: Thank you for tuning in to fiduciary alchemy. The coolest financial podcast you're likely to find.
[31:27] Craig Andrews: We go looking for voices like the one you just heard, because I want you to dodge the mistakes
[31:32] Craig Andrews: that I made and learn it without the coma, without the drama, without nearly paying the man.
[31:37] Craig Andrews: I don't know why I lived. When so many others die, that part's still a mystery.
[31:43] Craig Andrews: Now some folks ask, Craig, what is it you do? Well, I'm telling you now that's no mystery at all.
[31:48] Craig Andrews: We solve hard marketing problems in crowded markets. So good folks like our guests can rise
[31:54] Craig Andrews: above the noise, become visible, memorable, irresistible and grow like never before.
[31:59] Craig Andrews: If organic growth is your problem, reach out, call me. Let's make a plan and bring your next steps
[32:06] Craig Andrews: into the light. But don't leave yet, stick around a minute more and listen to bluesman
[32:11] Craig Andrews: grendel and the compliance choir deliver a word of caution just for you.
[32:25] Compliance Choir: This podcast is for information, education that is all.
[32:40] Compliance Choir: It is not financial tax or legal advice to guide your call.
[32:45] Compliance Choir: Nothing here's an offer, nothing here's a buy or sell.
[32:53] Compliance Choir: No recommendation, no solicitation. I'm saying it plain and well.
[33:10] Compliance Choir: [Music]
[33:15] Compliance Choir: Past performance ain't no promise of what tomorrow brings.
[33:21] Compliance Choir: Markets turning people loose on all kinds of hopeful things. Every investment carries risk.
[33:34] Compliance Choir: Prince of pork and fade away, what works for one won't fit us all.
[33:40] Compliance Choir: That truth is here to stay, fade away, fade away, hear to stay, yeah that's the compliance
[33:55] Compliance Choir: blues. Lord the compliance blues. Get your own financial tax and legal help before you make your move.
[34:07] Compliance Choir: That's the compliance blues.
[34:19] Compliance Choir: Fire, your situation's yours alone. Your needs are not the same, different facts and different goals
[34:32] Compliance Choir: can change the whole damn game. So talk to somebody qualified before you choose your role.
[34:44] Compliance Choir: Because the weight of every money move is your own load, your own load, your own load, your own load.
[34:58] Compliance Choir: That's the compliance blues. Lord the compliance blues.
[35:06] Compliance Choir: Get your own financial tax and legal help before you make your move. That's the compliance blues.
[35:36] Compliance Choir: [Music]
[35:50] Compliance Choir: Get qualified financial tax and legal advice.
[35:54] Compliance Choir: That is right for you.
[36:06] Compliance Choir: [Music]
This podcast is provided for informational and educational purposes only and should not be construed as investment, legal, tax, or other professional advice. Nothing in this episode constitutes an offer, solicitation, or recommendation to buy or sell any security, investment product, or financial service. Any opinions expressed by the host or guests are their own as of the date of recording and are subject to change without notice. Any examples are for illustrative purposes only and are not intended as a guarantee of any future outcome. Past performance is not indicative of future results. All investments involve risk, including the possible loss of principal. Individual circumstances vary, and listeners should consult their own qualified financial advisor, tax professional, and legal counsel before making any investment, tax, legal, or estate planning decisions.
