Bogleheads® Live 28: Meg Bartelt on RSUs, ISO, and IPOs

Ep>Episode

Su>Summary

Meg Bartelt answers questions on employer equity compensation, including restricted stock units (RSUs), private company incentive stock options (ISO), and initial public offerings (IPOs).

Sh>Show Notes

• Bogleheads® Live with Dan Egan: Episode 25
• Investment Policy Statement
• Bogleheads® Live with Dr. Sunil Wahal: Episode 6
• John C. Bogle Center for Financial Literacy
• Bogleheads® Forum
• Bogleheads® Wiki
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• Bogleheads® on Investing podcast
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The John C. Bogle Center for Financial Literacy is a 501(c)3 nonprofit organization. At Boglecenter.net, your tax-deductible donations are greatly appreciated.

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Transcript

>Transcript Jon: Bogleheads® Live is our ongoing Twitter Space series where the do-it-yourself investor community asks their questions to financial experts live on Twitter. You can ask your questions by joining us for the next Twitter Space. Get the dates and times for the next Bogleheads® Live by following the John C. Bogle Center for Financial Literacy on Twitter. That’s @Bogleheads.

[00:00:22] For those that can’t make the live events, episodes are recorded and turned into a podcast. This is that podcast. Thank you for joining us for the 28th episode of Bogleheads® Live where the do-it-yourself investor community asks questions to financial experts live. My name is Jon Luskin, and I’m your host. Our guest today is Meg Bartelt. Let’s start by talking about the Bogleheads®, a community of investors who believe in keeping it simple, following a small number of tried-and-true investing principles.

[00:00:51] This episode of Bogleheads® Live, as with all episodes, is brought to you by the John C. Bogle Center for Financial Literacy, a 501(c)(3) non-profit organization dedicated to helping people make better financial decisions. Visit our newly redesigned website at boglecenter.net to find valuable information and to make a tax-deductible donation.

[00:01:11] Before we get started on today’s show, a disclaimer. This is for informational and entertainment purposes only, and should not be relied upon as a basis for investment, tax, or other financial planning decisions. 

[00:01:20] Let’s get started on today’s show with Meg Bartelt. 

[00:01:23] Meg Bartelt, CFP®, RLP is the founder of Flow Financial Planning, LLC, a fee-only virtual financial planning firm dedicated to women in their early- to mid-career in tech. The firm specializes in pre-IPO (initial public offering) and IPO planning, and not making people feel bad about their finances.

[00:01:41] Meg Bartelt, thank you for joining us today on Bogleheads® Live. 

[00:01:45] Let me start with our first question that we got from username ‘JoeWoodstock’ from Bogleheads® Reddit, who writes:

[00:01:53] “I have a question on tax treatment of RSUs for Meg. I received an RSU grant with a four-year vest one year ago for $10,000 when the company’s stock price, let’s say CSP – he writes – was at $100. So, I should see a first-year vest of $10,000 divided by $100 divided by four equals 25 shares.

[00:02:14] If CSP is trading at $50 on the day of the vest, does that mean my taxable income from that event is $2,500 or $1,250? In other words, is the price on the day of the RSU grant used to determine the number of shares vested across the life of the grant, or is it also used to determine taxable value at each vest event?

[00:02:35] Jon Luskin, your Bogleheads® Live host, jumping in for a podcast edit. I already dropped some super-technical acronyms. Let’s break those down for those who aren’t equity comp nerds.

[00:02:50] The first one is RSU, which is short for restricted stock unit. Companies can compensate their employees with not just cash, but stock, too. Sometimes that’s via an RSU.

[00:03:07] Yet, it’s not as simple as a company giving stock to their employee. When it comes to RSUs, there are two important dates to consider. The grant date and the vest date.

[00:03:20] The grant date is the day when the company gives the RSUs to the employee. However, those RSUs aren’t fully the employee’s yet. They have to wait until the vest date for that to happen. 

[00:03:34] And now that we know what RSUs mean – and the difference between a grant date and a vest date for an RSU – let’s hear Meg’s answer to the question. 

[00:03:45] Meg: The only time when the grant price of the stock matters is when your company is calculating how many RSUs to give to you in the stock grant. That’s the only time it matters. After that calculation is done, the grant price no longer matters with RSUs. 

[00:04:05] Specific to this person’s question, the day those RSUs vest, it is the price of the stock on that day that matters.

[00:04:16] I jotted down the numbers. He has 25 RSUs vest. And the price on the day that it vests is $50. So, he will receive 25 times $50. $1,250 worth of RSUs on that day. And that’s what he owes income tax on. 

[00:04:36] Ginger: My name’s Ginger and I actually have a follow up question regarding RSUs, specifically when it comes to private companies. My understanding is that for private companies, RSUs are all double trigger RSUs, meaning you don’t actually realize a taxable event until the company experiences liquidation – like an IPO or something. Is that true for all private company RSUs?

[00:05:00] Meg: And just to back up, because obviously the speaker knows what double trigger means, but make sure everyone else does: in a public company, when you have an RSU grant, typically what happens is the RSU grant says, “Wait around. If you stay employed at this company for a year, at the end of that year, a hundred shares of company stock will become yours, and you will own a hundred shares on that day and you will owe income tax on a hundred shares worth of value on that day.”

[00:05:28] All well and good. It’s a publicly traded company. You could sell the shares if you wanted to, especially if you want to in order to pay the tax bill that them vesting will create. But if you work in a private company, you can imagine a hundred shares of this private company stock vests in the same way, and all of a sudden, you’ve got a tax bill based on those shares of private company stock. But you don’t have any way to sell the stock. It’s a private company. Now you have this tax bill created by this private company stock and no ability to actually sell that stock to cover the tax bill. So, it’s a lot riskier for the employee. 

[00:06:03] What most companies in the tech industry do is they create two triggers before the RSU fully vests and becomes yours for income tax purposes. That first trigger is still the, hey, just keep your butt in your seat until the vesting date. Stay employed at the company. That’ll satisfy the first trigger.

[00:06:23] And the second trigger is some sort of liquidity event. We like to think of that as going IPO. It can be going public in some other way, could be a SPAC or be a direct listing. It can also be getting acquired.

[00:06:36] So, that is how most private companies do RSUs. They do it double trigger so that the employee doesn’t have a big tax bill until they are also able to sell the stock in order to cover the taxes. 

[00:06:50] So, no, it’s not true. It is not true that all private company RSUs are double trigger. Most of them are because it is just way easier for the employee and probably the company too, to wait until the stock is actually public or a liquidity event, like an acquisition. It’s way easier to deal with taxes if it’s a double trigger. 

[00:07:18] I have had one client who works at a now-public, but then-private big tech where they did have single trigger “normal” RSU vesting while the company was still private. And it was just a lot more work on the company’s and employee’s part to figure out how many shares of these RSUs need to be withheld for taxes so that the full tax bill can be paid without putting dollars out of my pocket into it. Or alternatively, if you actually want to retain more of the shares of the company’s stock, not have them withheld to pay the taxes, now you have to take money out of your pocket, put some of your existing wealth at risk in order to pay the taxes on that single trigger RSU vest. So, it’s rare. It creates a lot more complexity, but it does happen. 

[00:08:10] Lockup periods are generally associated with going public in some way. Going IPO or direct listing. Direct listings lean more in the direction of no lockup periods. Generally, when we’re talking about lockup periods, we’re talking about IPOs. Company goes public, and then you as an employee have to wait six months to do anything with your stock. This created a problem. Uber was a great example of this. These double trigger RSUs, they vested, they fully vested. The second trigger occurred on IPO day. So that’s the day that all these employees with RSUs incurred this giant tax liability because they incurred all this RSU income, but then they weren’t able to actually sell any of the stock for another six months. Which created problems in two ways. 

[00:08:57] One, you’re taking tremendous investment risk because now so much of your net worth is invested in this single stock and you’re unable to get out of it. So, you’ve already incurred this tax liability, and you are just crossing your fingers hoping that the stock price doesn’t drop in the next six months before you can diversify a bit. And also, in Uber’s case, it went public in, I think December. So, before the end of the tax year. April 15th rolls around. If you had a lot of RSU income, let’s say $1,000,000 of RSU income, your remaining tax bill is probably hundreds of thousands of dollars. But you’re still not able to sell the company’s stock. So, now you’ve got to come up with cash out of your existing wealth to pay that bill because the lockup for actually selling the company stock doesn’t expire for another month.

[00:09:43] What I’ve seen in IPOs in the last few years: companies still had a six-month lockup, but had these trading windows inside that six-month lockup. Stockholders had, for example, seven days immediately following IPO day in which they could sell a certain percentage of their shares. Up to 15% of your shares. And then three months later there was another constrained trading window. So, you could get some, but not all liquidity before the six-month traditional lockup expired. 

[00:10:13] Jon: Let’s talk about a case study. I was working with a gentleman this past Monday and he had a whole bunch of Facebook, aka Meta RSUs, and they had decreased substantially since they were vested, as with a lot of stocks I would imagine right now. What would you say to him in helping him make the decision to keep or sell those RSUs? 

[00:10:39] Meg: That’s painful. Meta has been particularly hard hit even before the 2022 decrease in tech stocks in particular. But that is a position that a lot of our clients and just a lot of people in tech find themselves. And yes, we will talk about some sort of mental framework. But, just starting with this person is absolutely not alone. Most people are probably in his situation and it just sucks, right? Because we cannot help but wish, ah, “if only I had sold my RSU shares when they vested or a year ago,” or what have you. 

[00:11:10] I would say one thing that comes out of this conversation is, if we harken back to a year ago, or in Meta’s case maybe a year and a half ago, people who held Meta stock, the reason you were holding it is because you thought that the stock price was going to continue to go up.

[00:11:27] We had no conception that the stock price was going to fall, especially not this much. That’s what got us into this situation is believing we knew what the stock price was going to do, and then having reality just spank us. 

[00:11:41] The same logic applies today. We do not know. We cannot know what is going to happen to Meta stock in the future. Is it going to continue to fall? Maybe. It’s still worth a bunch of money. It could lose some of that value. It could recover. It could go on to do the Facebook equivalent of the iPhone and become 10 times what it’s worth today. We just don’t know. We can’t know. 

[00:12:05] So we have to focus on what we do know. And what we do know is our own personal financial situation and our own desires for what our life is and what it will become. And this might feel a little squishy or ‘woo,’ but honestly, that is the way you make your best decisions about these technical issues that are otherwise unknowable.

[00:12:33] So you’ve got three decisions that you can make about the stock. You can sell it all now. You can hold it all now, or you can sell some of it.

[00:12:41] That sounds dumb to break it down that way, but I find that oftentimes that simplistic of a framework really does help people think through their options. And, I think the reason to sell things now, if you have goals in your life that this money could now fund – they could either fully fund it or get you within spitting distance of it – if you want to.

[00:13:07] For example, we work with Jon, as you mentioned, a lot of women in their early to mid-career. This is prime home-buying-time. If buying a home is really important to you and if it’s not just like swapping another financial goal, it’s really important to you. If it’s really important to you, and selling your vastly decreased in value Meta stock right now could get you into that home, that’s a really strong indicator that you should consider selling your stock. Because regardless of what the stock does later, even if it ‘10X’ed, you would have already locked in this aspect of your life that is truly important to you. You have honored this value, this ideal life desire – all of the verbiage – with this stock. And that’s something you can know, whereas we cannot know what the stock price will do later. 

[00:13:58] If you don’t have any pressing goals that you can put a dollar amount on and you have an otherwise healthy, robust financial situation: you’ve got a good cash cushion, you’re saving enough for retirement, you’re saving to your 401(k), and if you make a really high income probably saving in addition to your 401(k) – so you’re saving enough for your long-term financial independence, and you’re already actively saving enough outside of this Meta stock, then in my opinion you can take a little more risk with it. Because if it goes to zero – which, yes, not likely, but let’s remember Enron – if it goes to zero, you will still be fine.

[00:14:44] So basically by keeping it, you’re gambling. Like if this works, boom, I’m going to change my life qualitatively. But if it doesn’t work, which is a much more likely outcome, then I’ll still be okay, and I will not have endangered or sacrificed anything that’s core importance to me. 

[00:15:04] And I find that when our clients make decisions about equity compensation, regardless of what the question is, but when they’re making those decisions driven by, “Okay, what money do I need, when, in order to fund my ideal life,” they very rarely regret those decisions because regardless of what the stock does, they’ve already created for themselves the kind of life they want.

[00:15:30] Jon: I think about the actual case study. And that was a very specific goal of the gentleman that I worked with. He wanted to buy a house. So, naturally selling some of that employer stock for that home purchase, that could help him get closer to that goal.

[00:15:47] Meg, should I withhold 22% or 37% on my RSUs when my company goes public?

[00:15:55] Meg: AirBNB offered this option when it went public, and we helped lots of people through the AirBNB IPO. We have clients who elected the 37% withholding and definitely kicked themselves in the butt afterwards because AirBNB listed at $68. And so, all of those shares were withheld at the $68 price and then immediately popped to $150. If they had only withheld 22%, they would’ve had an extra 15% of shares that they could’ve sold at a much higher price.

[00:16:26] So that’s one risk: you choose the higher withholding, and if the stock price pops after IPO, then you’re missing out on the extra value that those withheld shares – that 15 percentage points more of withheld shares – could have gotten you. 

[00:16:43] Now, let’s say you withhold only 22%. And you’re in the 37% tax bracket. You’re still going to owe 15 percentage points more in federal taxes on the RSU vest. What happens, as in the case of Uber, the stock price falls. That doesn’t change your tax liability from the vesting.

[00:17:02] Let’s say it’s $1,000,000 worth of RSU income. You still owe $150,000 on all those RSUs that reach their double trigger the moment it IPOed. You’ve got to come up with that $150,000 somewhere. Are you now going to sell these vested RSU shares at a much lower price than they vested at? Are you going to come up with extra cash and keep the company shares in the hopes that it’ll go up?

[00:17:31] So either choice you make has a risk. One is a risk of losing money. That’s if you only withhold 22% and still owe an extra 15 percentage points. The other risk if you withhold 37%, the risk there is not that you’ll lose money, but you’ll lose out on money, if I can introduce that nuance. You will not get the extra gains. You’ll miss out on gains on those certain percentage of your shares. That’s the risk, and possibly the questioner understood that those were the two risks.

[00:18:03] Now what you have to do again is go back to your understanding of your own personal financial situation. Cause what you don’t want to do is open yourself up to a risk that would be catastrophic for you: catastrophic to you in general, or to a specific goal you have.

[00:18:21] Let’s say you withhold only 22% and you owe 37%, and the stock price falls afterwards. How are you going to cover the tax bill? If you’re already wealthy, if you’re already on track to meet all of the most fundamentally important goals in your life and that this extra tax bill that you’d have to pay out of cash or out of vastly decreased-in-value company stock, if that would suck but not be catastrophic, okay, maybe that’s a risk that you can afford to take in an effort to gamble that the company’s stock price will rise.

[00:18:55] The one client I’m thinking of who at AirBNB, withheld 37% and kicked herself afterwards because the AirBNB stock price rose. She was fine financially, but her emotional relationship to money was so anxious that if she had chosen the opposite way and the AirBNB stock price had fallen, she would have been a wreck. The way she went, she regretted the choice, but she wasn’t devastated by it in the other way she would have been. So that’s a question that you have to really familiarize yourself with your own relationship to money is: how much risk are you willing to take on?

[00:19:32] And then the other direction is if you withhold 37% and the stock price ends up popping up and you lose out on all that extra value. Think to yourself, how will that missed out on money impact me? Will it really? Because for a lot of people it won’t really. Yes, it’s nice money, but if you’re 35, as long as you have enough money to buy your home or to take next year as sabbatical, everything else you can make up over the next few decades.

[00:20:02] That’s a really elaborate way of saying “it depends,” but you have to understand the risk of each decision and whether your emotions and your financial situation and your financial goals can withstand that risk if it comes to fruition. 

[00:20:17] Jon: Hey, plan for the worst case. What could possibly happen for a given outcome? How are you going to feel about that? Then maybe it makes sense to pick the opposite. Know yourself. Understand your personal goals first before moving on to those technical details. Amazing framework to help folks decide what’s appropriate for them.

[00:20:34] Let’s bring it over to the transition from private to public. My company is going public. What should I be thinking about? 

[00:20:42] Meg: Going IPO is a huge transition because it can result in such a windfall for you. The best thing you can do for yourself going through any transition or preparing for any transition is to know yourself. Know your current financial situations or the quantitative, the objective, the factual. But also do some self-work, man. Talk with a therapist or a friend or something about what really matters to me. Because once those big dollar signs start popping up, it’s really easy to get distracted and just zero in on maximizing after-tax dollars.

[00:21:22] That is the whole goal of any of this: maximizing after-tax dollars. And it’s just not. The goal of all of this to fund a fulfilling or meaningful life. Now, sometimes that overlaps with the idea of maximizing after-tax dollars in the long-run, but it doesn’t need to. But the ultimate goal is to fund a life that feels meaningful and fulfilling and ideal to you.

[00:21:46] So that is what you need to get straight on first. Honestly, the clearer you get on that, the easier the technical decisions just drop out of it. They’re not some big, “oh, should I, shouldn’t I? Let me construct some pivot tables.” No, it just becomes really obvious a lot of the times what you should be doing. So self-work, super important. First step, honestly, it’s the first step in any sort of meaningful financial decision. 

[00:22:13] Second step is to understand how the IPO is actually going to work. All IPOs work differently. Sometimes they’re minor differences. Sometimes they’re major differences as I was referring to earlier when AirBNB went public. And they were going to offer this seven-day trading window starting immediately at IPO day. That was, I think literally the first time that it happened.

[00:22:36] You need to understand just the technicalities of the actual IPO. Now, a lot of these you cannot find out until maybe two days before it happens. Your company files their S-1, which announces, “hey, we’re going to go public via an IPO,” but you won’t actually know which specific day it’s going IPO, and what the list price is going to be until maybe two days ahead of time.

[00:22:59] So some of these things, you have to wait. Some of them, (and if your company’s good), they will give you as much instruction as possible ahead of time. How to navigate the financial institution’s website interface? Is Fidelity the one who’s administering your IPO? Can you familiarize yourself with the website? How do you sell stuff? Where will you actually see the shares on the Fidelity website? So, you need to spend some time figuring out, clicking here, navigating there, selecting this thing, blah, blah, blah.

[00:23:29] Third, I would say write down a plan for when and how many shares you are going to sell. And you can base this on, “how much money do I actually need for my goals – for pressing goals?” Do I not have a cash cushion yet? Cool. I am going to make sure that as soon as I can, I sell enough shares to create a cash cushion for myself. Do I want that down payment? Do I want the money to take a year-long sabbatical? Those are going to be your most pressing sales. 

[00:23:59] And beyond that, the idea really devolves into diversification. The sort of boring, intellectual, statistically driven, okay, I know concentration in a single company stock – regardless of the company, not just my company – is really risky. And statistically it will not pay off on average. 

[00:24:17] So create a schedule for when and how many shares you are going to sell. And the reason a schedule is the right way to go is because you can create that before all the fervor and emotional excitement and chaos and stress of the IPO actually happens.

[00:24:33] Because once that starts, IPO day is going to be insane. You and all your coworkers are going to be constantly refreshing Yahoo! Finance to see if the stock has finally started trading. Quite possibly the financial institution’s website is going to crash. You’re not going to be able to get access; it is just going to be stressful and chaotic.

[00:24:53] You do not want to be making any decisions in the midst of that emotional fervor. So, if you can create a strategy ahead of time that is reasonable – and I say reasonable because there’s almost never a right answer to this; there are many reasonable answers. You can just start executing that strategy like a dumb animal. You’re not making decisions. You’re just clicking buttons based on what this already-written strategy says. 

[00:25:24] Jon: Check out Bogleheads® Live Episode #25 of the podcast where Dan Egan talks about the importance of putting together a plan that’s going to help you avoid making emotional decisions in the moment. 

[00:25:42] Meg: And then also, understand that no plan is actually going to survive the IPO actually happening. Because who knows what the price is going to do. Is it going to pop? Is it going to plummet? Is the website going to crash? Just know that that day and possibly that week of the IPO is just going to be insane. Try not to expect yourself to actually get anything done at work that week. 

[00:26:02] There’s a ton more. I’ve written so many blog posts about going through an IPO that I could go on and on about all the nuances of it. But I hope that at least gets you to IPO day well enough.

[00:26:14] Jon: Kudos to all of Meg’s phenomenal blog posts on the subject. Great resource to learning about equity comp on her website.

[00:26:23] Meg, your point about having an investment plan is spot on for selling out of your employer stock. And it’s going to be the same thing for any investment plan. Crafting an investment policy statement is going to help you stick to your goals. And in the show notes for our podcast listeners, I will link to the Bogleheads® Wiki page that talks about putting together your own investment policy statement.

[00:26:44] Ginger has a speaker request. 

[00:26:46] Ginger: This is less of a technical question and more of a personal one. For all intents and purposes, it would be the right year for us, tax wise, to exercise my husband’s ISOs. But I find myself unable to take my own advice. Because at this point we are stretched a little thin and we would have to take out a loan in order to fund the purchase of those ISOs.

[00:27:10] What other things should I be considering here, both personally and technically in helping to make this decision? And do you have any resources for equity loans and your thoughts on loans for people who need them to exercise ISOs? 

[00:27:26] Jon: ISO is an abbreviation for incentive stock option. An ISO is a stock option provided by an employer as a form of compensation. And that ISO he has very special tax treatment. The idea behind an incentive stock option is that you’re generally able to buy company stock at a lower price than its trading at, or what it’s worth. For example, you can buy Company X stock at $10 per share, even though it’s trading at $20 per share or is valued at $20 per share. And then to qualify for better tax treatment, you’ll need to hold those shares for quite some time. 

[00:28:07] Yet, you need cash in order to buy the stock. And that gets to the root of Ginger’s question. Using her cash to buy private company stock means likely depleting her cash reserves, possibly even her emergency fund.

[00:28:22] And because it’s private company stock – not easily sold as is the case with publicly traded stock – Ginger has fewer options to sell that private stock, replenishing her cash reserves. 

[00:28:36] Meg: What I zeroed in on, Ginger, in your description is if you were to exercise your ISOs this year, while it might be an optimal year tax-wise, if you used all of your own money, it would leave you in a precarious position. 

[00:28:52] Exercising ISOs is probably one of the most complicated decisions to make, especially in private companies where there is no guarantee that you’ll ever be able to sell that stock for any particular value. 

[00:29:04] And I’m talking about private companies, right? Cause if it’s a public company, you could exercise and sell shares immediately in order to pay the tax bill. So, you wouldn’t need to incur any risk in that regard. 

[00:29:15] There are definitely organizations out there who will say, “Look, I will lend you the hundreds of thousands of dollars to exercise ISOs in your private company in exchange for a percentage of the upside. So basically, X percent of your shares now belong to us. And if and when this company does go public and the shares do become liquid, we own those shares.” So, there is some way of actually financing the ISOs if you decide you want to do them this year. 

[00:29:40] In my world, the first rule of financial planning is don’t put yourself in a position where you’re risking something important. So, it sounds like you’re sort of already there and that you’re talking about taking a loan to do this. So, in a way you’re not taking on any risk. You’re using their money. 

[00:30:00] One of the risks is a lot of these loans, if the loan gets forgiven it counts as income to you. You owe taxes on the amount of the loan. And that can be meaningful. Like if you get an extra, you know, few hundred-thousand dollars of loan and it gets forgiven, your tax bill could be tens of thousands of dollars. So that is not without risk.

[00:30:16] Another thing to think about is if you exercise some of the ISOs, is there a private secondary market for these shares? Well, let’s say you exercise 10,000 shares. Could you go to a Forge Global, for example? Is there a buyer through the Forge Global marketplace where you could sell some of those shares and use that money to pay the tax bill on the ISOs? Again, not putting any of your own money at risk, just giving up some of the shares in order to protect yourself from that risk.

[00:30:41] I would also say that just because it is tax wise, the best year to exercise your ISOs doesn’t mean you should do it. There are other considerations. The only reason to exercise ISOs now versus later is because you think you’re going to get a lower tax rate. It doesn’t mean you’re going to lose out on the stock value, just buy at a higher tax rate. It is okay to pay a higher tax rate. If you can eliminate risk by paying a higher tax rate, that is a legitimate choice. You are concerned about your after-tax money. And if you can get sufficient after-tax money to fund the life you want, all the while protecting yourself from downside risk, cool! That is a really good strategy to pursue. 

[00:31:31] Without knowing more details about your personal situation, I would say that just because it’s tax wise doesn’t mean you have to do it this year. You can delay until you can do it in a less risky manner. Or if you’re like, “no, I want to do it this year, it’s meaningful taxes that we’d save,” then maybe investigate some of those financing companies where you can really minimize the amount of your wealth that you’re putting at risk and basically foist that risk onto some third party in exchange for giving up some of the upside because some of the shares will now belong to that third party.

[00:32:05] One of the perspectives to think about is this idea of regret minimization. How do I make a decision now that’s going to minimize my regret in the future? This often comes out to, “Oh, I’ll do a compromise. I won’t exercise all my ISOs,” or “I’ll keep some of them unexercised,” or “I’ll exercise them all, but I’ll give some of them up either through a financing option or selling them through a Forge Global in order to pay the tax bill.” 

[00:32:33] If the company hits it big in the future, woohoo! I do have some of these shares that I’ve owned for several years now. I get the long-term capital gains tax rate, yay! But also, if the company implodes, I haven’t risked a catastrophic amount of my own wealth doing it. 

[00:32:50] And then of course you’ll be surrounded by people who swung for the fences and exercised all their ISOs and put all their money into it. And if the company does really well, you’ll feel like an idiot next to those people. But that’s hindsight. That is 20/20. Your decision was still the right one to make, even if it didn’t end you up with the most after-tax dollars. 

[00:33:09] Jon: Any final thoughts before I let you go?

[00:33:11] Meg: I think I made it pretty clear that internal values life work really has to be the driving force behind all of this technical work. And I will also say if you do go through an IPO or a tender offer or something that creates a windfall for you, that that is a hard psychological transition to make.

[00:33:33] We work with a lot of people in their thirties who were $200,000-aires before the IPO, and now they’re multimillionaires. But, their identity is still that of a $200,000-aire. But now they have risks and complexities and opportunities available to them that they never did before. And just give yourself some grace and really a lot of time to transition into that new identity of someone who has wealth.

[00:33:58] Jon: That’s going to be all the time that we have for today. Thank you for Meg Bartelt for joining us today, and thank you for everyone who joined us for today’s Bogleheads® Live. Next week we’ll have Hozef Arif answering your questions about investing in bonds amidst high inflation. That’s going to be a really timely topic.

[00:34:14] Until next week, you can access a wealth of information for do-it-yourself investors at the John C. Bogle Center for Financial Literacy at boglecenter.net. For our podcast listeners, if you could take a moment to subscribe and to rate the podcast on Apple, Spotify, wherever you get your podcasts. 

[00:34:28] And thank you to those who have left reviews so far, including Matthew P., who left a review on Apple Podcast writing, “Very informative and excellent podcast.” Thank you, Matthew.

[00:34:38] And a thank you to one of our volunteers, Jeremy Zuke, for transcribing Episode #6. That’s one of my favorite episodes that explores the hidden costs of mutual fund investing. Folks can check out Episode #6, our interview with Dr. Sunil Wahal, and the transcript that’ll be available for that.

[00:34:55] Finally, I’d love your feedback. If you have a comment or guest suggestion, tag your host @JonLuskin on Twitter. Thank you again, everyone. Look forward to seeing you all again next week. Until then, have a great week.