Episode 217 – Aaron Rubin

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[00:00:00] Richard Matthews: Hello and welcome back to the Hero Show. My name is Richard Matthews. Today I have live on the line, Aaron Ruben. Aaron, are you there?

[00:00:06] Aaron Rubin: I am here.

[00:00:08] Richard Matthews: Awesome. Glad to have you here. I know you’re calling in from the San Francisco Bay area, is that right?

[00:00:13] Aaron Rubin: Yeah, yeah. Actually, I’m in San Francisco right now. So I live in just south, but but my office is here.

[00:00:20] Richard Matthews: That’s awesome. My family, we travel full time. We’re in Florida right now, but when we were in San Francisco. I had two of the craziest things I’ve ever seen in my life happen in San Francisco. One of them.

[00:00:31] Aaron Rubin: Shocking. Go ahead.

[00:00:32] Richard Matthews: Yeah. Yeah. One of them was we got Ninja rolls attacked by a lady who looked like she was maybe 130, 140 years old on on a bike.

[00:00:42] And we were getting ready to go on like a mass transit thing cuz that’s what you do in San Francisco is you get on the cool little trolley cars and we’re waiting to get on one. And this lady who like, I swear, just so old, she comes flying up to us on her bike and just like runs the bike into the curb right where we’re at, and Ninja rolls off the front of it and then pops up in front of us and is like, you have the cutest baby in the whole world.

[00:01:08] And just that was like, I don’t know how she was like standing up because she looked like my grandmother’s grandmother.

[00:01:15] Aaron Rubin: Well, you know, I’ll tell you what. You know, being in the city, I can just tell you this Mets a heck of a drug. And there may have been some substances involved. Even for those who are in their hundreds.

[00:01:30] Richard Matthews: The other one which was even funnier we were in downtown by that big pointy building.

[00:01:35] Aaron Rubin: Yeah, Transamerica, right?

[00:01:36] Richard Matthews: Yeah. That one. The Transamerica building. And there’s this little grassy patch where people would walk their dogs.

[00:01:43] And there was a gentleman there who was dressed up like a dog walking in the grass patch, which is, that’s not the crazy part. I mean, you know, some people like to dress his dogs. He had his poodle holding a leash, standing on the sidewalk, walking him. So he was being walked in the dog park by his dog and I was like, that’s something you only see in San Francisco right there.

[00:02:07] Aaron Rubin: You know, I’m hoping there was a camera somewhere and that it was like one of the art students, you know, from the university art that was like trying to like do something cuz that is the human zoo on display for sure. So, yeah, welcome to San Francisco. I’m glad you had an authentic experience. Yeah. Sounds like you had a good time.

[00:02:29] Richard Matthews: Like San Francisco, other than those two things was actually really awesome. We got to have like, you guys are famous for the the sourdough bread and the clam chowder and like, was it Pure 39, where they have like the mall on the picture. It was all super cool. The kids loved it and we found like an ancient video game museum that they all got to go and play in.

[00:02:46] Aaron Rubin: Yeah. That’s, you know what’s funny? In my family, I just stumbled upon that one just a year or two ago, and we were like, where’s, we had no idea. Did you try the arm wrestling one?

[00:02:59] Richard Matthews: We did. We tried all of them. We spent like 60 bucks.

[00:03:01] Aaron Rubin: Oh my gosh. Oh my gosh. I injured my hand trying to do the arm wrestling one. My wife thought to be hilarious if I did like one.

[00:03:11] Richard Matthews: Yeah. So anyways, I was like, San Francisco is absolutely worth visiting, but it comes with both fun and crazy is my point.

[00:03:20] Aaron Rubin: Yeah. No, that’s cool. It’s an awkward description.

[00:03:24] Richard Matthews: So what I wanna do before we get too far into this, is just a brief introduction of who you are, and then we’ll just dive into your story.

[00:03:28] So you are an attorney, a CPA, and a certified financial planner. And you run a wealth management practice, integrates tax financial planning and investing. You help your clients minimize their tax liability and keep more of their equity compensation so they can support the people they love and the causes they care about the most.

[00:03:45] So what I want you to start off with Aaron is, why don’t you tell me what it is you’re known for, what you do, who you serve, what you do for them?

[00:03:52] Aaron Rubin: Yeah, so we’re known for our pre IPO stock compensation planning. So for people who are at companies who are not yet public but are still issuing stock to their employees there are lots of different choices to make and it’s confusing at times and there are often issues with deadlines that people don’t know about.

[00:04:16] And so when people have questions about tax or strategies surrounding buying or selling their company stock that isn’t readily sold they come to us and, that’s who we help. So people who are, and usually they’re in their C or their D round of financing and they’re usually.

[00:04:36] You know, senior engineers, that sort of thing. Sometimes, you know, getting into the C-suite are founders, but again, everyone sort of needs a little help cuz it gets confusing quickly.

[00:04:46] Richard Matthews: Yeah, that’s interesting. I have a friend of mine actually, who just got I don’t know what the word is in Silicon Valley was it like sniped or something from one company to another with a giant free IPO stock package.

[00:04:56] And he was just telling me they’re getting ready to IPO at the end of the year. So that might be like a good referral for you. Right.

[00:05:02] Aaron Rubin: Yeah, no, that’s perfect. Although, I’ll tell you what, I have not talked with anyone and I’ve talked with a different level, different numbers of C level executives, and everyone’s saying 2023.

[00:05:14] So if your guys going 2022, that’s great.

[00:05:17] Richard Matthews: Oh, I have no idea.

[00:05:18] Aaron Rubin: Just joined then he.

[00:05:20] Richard Matthews: They just said it was like the end of the year or maybe early next year, so I’m not sure when it’s happening.

[00:05:25] Aaron Rubin: Yeah. The, again, everyone’s talking about 2023, but if your friend just joined, he probably doesn’t have any stock to sell, cuz there’s probably a lot of it’s not vested yet.

[00:05:35] Richard Matthews: Yeah. I have no idea. I didn’t get that far into the discussion with him.

[00:05:40] Aaron Rubin: But obviously with the with the pre IPO thing, when you go IPO usually there’s six months before you can start selling your own stock.

[00:05:50] Or sometimes they’ll let you sell a little bit up front, but most of it you gotta wait anyway. So even if you joined six months ago, he may have some that window opens up for him. He might have some availability to get some liquidity.

[00:06:06] Richard Matthews: Absolutely. And it’s a really specific niche to be in pre IPO stock planning. So, what I wanna find out is like, how did you get into that space for financial planning? Right? I know on this show, we talk about the your origin story. Every good comic book hero has an origin story. How they Became the hero they are today, and we wanna hear that story. Were you born a hero or were you bit by a radioactive spider that made you want to get into pre IPO stock planning and wealth management?

[00:06:29] Or you starting a job? How did you get here? Essentially, what was your story?

[00:06:34] Aaron Rubin: Yeah. Bitten by a radioactive spider for sure. .And although I’ll admit something up front. The very first stock that I bought for myself was Marvel back in 1993. It was awesome until they went bankrupt.

[00:06:47] And then, I lost everything. So, talk about, you know, a good way to start an education. So yeah, I didn’t get into this sort of on purpose. And I guess that’s where the radioactive spider comes in. I went to law school and while I was in law school, I met my wife and after we decided to get married her father said, you know, do you want to do what I do?

[00:07:09] And. I was like, I don’t know. And he said, well, you know, I help people with their investments. And I said, Oh, I mean, I didn’t know anything other than my Marvel experience. So, you know, in my mind you buy a stock and then it goes bankrupt. But yeah, which apparently isn’t the plan.

[00:07:25] But I said, sure. You know, that sounds good to me. You know a lot of the people that I knew who were in accounting, I mean, they were buried in tax season. Their hours were terrible. They didn’t see their family for months on end. And I thought, that doesn’t sound like it’s for me.

[00:07:43] Same thing with my lawyer friends. My lawyer friends, you know, working crazy, getting paid nicely, but working crazy hours and not really seeing their families. And I thought that isn’t for me. And so I had this opportunity and he said, well, that’s great. I can’t take you on now, so why don’t you spend some time in public accounting.

[00:08:00] I said, sure. At that point, I didn’t have my CPA yet, but I had a degree in accounting and I worked for three years and and then joined him in late 2009 or mid 2009. And it’s been fantastic. I’ve really enjoyed helping everyone working with like the smartest people in the world, it’s been great and yeah, I wouldn’t trade for anything.

[00:08:23] Richard Matthews: So it’s something you sort of almost fell into is helping people do their tax planning for pre IPO stuff, is the pre IPO sort of niche, just sort of because of where you’re located, because you’re in the tech valley, that that’s the people who are experiencing that sort of problem are just readily available?

[00:08:41] Aaron Rubin: A lot of them are here, there’s a lot all over the place. A lot of people are moving outta California. Some are going to Florida. You know where you are right now a lot of going to Texas and anywhere else where the taxes aren’t as horrendous as they’re here.

[00:08:58] You know, when we first started out, or when I first started out, we were not that specific of a firm. As time has gone on, you know what happened, happened. The reason why we got into this was because of Zoom. And this was pre Covid. So we got a referral from an attorney whose client was at Zoom and they needed some help on some of the tax and financial issues.

[00:09:21] And so they came, they talked to us and we gave them some good information and they were like, Oh, that’s really helpful. And all of a sudden we had four or five Zoom people become clients. And you know, before then we were sort of what I call a generalist, where we were looking at, you know, anybody who had a pulse and, you know, $500,000 or a million dollars, whatever it was, they could feel free to join.

[00:09:46] And we were kind of targeting everyone. And then, we went through this whole thing with Zoom, and at that time we were actually considering closing down our tax practice because it’s so labor intensive. And after the whole Zoom thing, you know, I sat down with, you know, my partner who were working on these Zoom clients with, and I said, you know, we do this like really well.

[00:10:08] Like we’re really good at this. This is what we should be doing. Like, not, we should forget about the other stuff. Yeah, we ere right, we discover superpower. And so from then on we said, all right, that’s it. So whenever we talk to people, we’re gonna talk about pre IPO stock options, and we’re gonna reorient our website to talk about pre IPO stock options.

[00:10:29] And we’re gonna reorient our blog to talk about pre IPO, I mean, this is what we are going to be. And and it’s been awesome. I’ve loved it. You know, I think before when I was telling people what I did as that generalist, like what I found was I wasn’t compelling to myself. Like, I mean, I’d sit there, and as I was talking, I’m like, I’d be like, Oh my, I’m so boring.

[00:10:52] This is Terrible. Like, I mean, how is anyone gonna differentiate me from anybody else in this space? And so having found that niche, right? I love talking about it and I get excited talking about it. And people think of me when they hear someone with stock options.

[00:11:12] And that’s exactly what we want. So I mean, that’s how we came into it. So that’s sort of the whole long core story.

[00:11:19] Richard Matthews: It’s really interesting because like the first thing that came popped into my head when you said what you did was like, I know people who are in that situation that makes you easy to refer.

[00:11:28] Aaron Rubin: Right, Right.

[00:11:29] Richard Matthews: If you’re like, I just do tax planning or, you know, wealth management, like, it’s too general for just like people in my head that I know their stories, for me to just fit you in somewhere, but you’re like, I do pre IPO stock planning. I’m like, I know someone who’s doing that right now, so like I can refer them. That makes you like stand out in the crowd.

[00:11:50] Aaron Rubin: Yeah, well when I talk to someone, I’d say, Hey, Oh yeah, my name’s Aaron Rubin, and I help retirees and pre retirees and people who are coming into money from either divorce or inheritance, you know, plan for their wealth.

[00:12:04] I mean, that didn’t speak to anybody, yeah, no, it’s been fantastic.

[00:12:10] Richard Matthews: So I’m want to talk then a little bit about your superpowers. Right? So every iconic hero has a superpower, whether that’s their fancy flying suit made by their genius intellect or their ability to call down thunder from the sky. In the real world, heroes have what I call a zone of genius, which is either a skill or a set of skills that you’re born with, where you developed over the course of your career that really allow you to slay the villains in your client’s life, so to speak and come out on top on their own journeys.

[00:12:33] And your superpower, the way I like to frame it for my guests is probably there’s a common thread in all the skills that you’ve developed over your career, and that common thread sort of ties everything together, and that’s where you probably locate your superpower. What do you think your superpower is in this business of wealth planning and tax management?

[00:12:54] Aaron Rubin: Sure. I’d say it’s understanding a system and manipulating it, that’s it, whether that’s the tax system, right? And everything that goes behind that. And it’s not just, oh, here’s your tax bill. It’s how do we lower that tax bill? What are the different strategies that we can take that maybe we don’t think about as tax necessarily, but that have tax effect that can help us out?

[00:13:20] So for instance, you could say, well, I have a client who is really into charities and he had a big payday from an IPO, and he definitely wanted to give to charity. And it’s about thinking about, well, okay, with that goal in mind, where can we pull from, from estate planning, from tax, from the investment side, where can we do all these things and, where they all harmonize together and then bring them together to get the best effect for the client.

[00:13:53] So in that case, the client said, well, I’m really passionate about, you know, it was autism research. And I said, okay, well, we could, you know, why don’t we start a family foundation, you know, where you can control a lot of disasters. So sort of all, anything you put in the foundation, right?

[00:14:10] You still control. It’s not like it’s, you know, being run by somebody else, you know? Oh, and by the way, you know, if we use a charitable trust vehicle, you know, we could actually get a huge tax deduction in your income tax and save you a bunch of money there.

[00:14:23] Oh, and by the way, we can also use that same vehicle to create tax losses to put on your tax return in the future, so you pay less tax in the future too. And so that superpower is saying, okay, you know, I know these different parts exist. How can we get them together to get the effect that we’re looking for or to maximize the effect we’re looking for.

[00:14:46] Richard Matthews: So I’m gonna try and put this in super dumb math and hopefully it’ll make sense and you can correct me where I’m wrong. But I wanna make sure I’m understanding this, but like, so let’s just assume you have a tax bill, easy math, a hundred thousand dollars that you owe the government.

[00:14:59] And what you’re talking about is being able to say, hey, instead of just paying the government a hundred thousand dollars, if we create like a tax foundation or use some sort of charity thing and you take a portion of that money and put it into the foundation that lowers your tax liability, right? So you have less tax liability. You’re still not putting that a hundred thousand dollars in your pocket, but at least portion of it is going to something that’s a good cause and not necessarily going to the government, if that makes sense. Am I understanding that correctly? Or am I close?

[00:15:32] Aaron Rubin: You’re close. But it’s even better than that because, with this client’s, what’s gonna happen with this client is trust is being run. The money is going from the trust to his foundation where he gets to spend the money for the causes he really cares about.

[00:15:44] Now, the trust as it’s running. We have a portfolio in there and it’s generating capital losses inside of the portfolio. Because the way we structure the trust, those capital losses from the portfolio, which we’re intentionally trying to grab, they’re actually coming under his personal tax return.

[00:16:03] So not only is that foundation getting its money and it is, the guys also getting additional capital losses to offset future capital gains. But wait, there’s more. And when that trust is done paying out the foundation over it’s a 10 year trust. Whatever’s left over inside of the trust comes back to him.

[00:16:26] So it’s sort of like he lent the cash to the foundation for like 10 years and what’s ever left over after investing, he gets to take the money back. So it’s a super powerful way to go about giving money to charity.

[00:16:41] Richard Matthews: So you get to give money to charity and you get to realize losses that reduce your tax burden every single year for the entire duration of the trust. And then whatever’s left over, you get to take back. So it’s like compounding money.

[00:16:56] Aaron Rubin: Right, and you got a tax deduction when you put the money into the trust first time. So in your example, you know, you owe a hundred thousand dollars, let’s say you would use this strategy for a lot bigger size.

[00:17:11] Richard Matthews: Larger sums of money, just easy math hundred thousand, it’s easy to hold in the head.

[00:17:15] Aaron Rubin: Yeah. Right. And again, I don’t want anyone be like, oh, I’m gonna go get a charitable trust. You know, again, the legal costs would eat you up on this, right? So you’d wanna make sure it’s sizable, and let’s say you put $10,000 into, you know, this charitable trust, you then turn around and put $10,000 deduction on your tax returns.

[00:17:34] So you recognize a hundred thousand dollars of income, less $10,000, you know, means you have $90,000 of income for the IRS. Along the way that $10,000 generates another thousand dollars of capital losses, which you use on your tax return. And then at the end, after it’s done paying out the charity, however much it’s supposed to pay out, whatever’s left over from that original $10,000 comes back to you.

[00:17:58] I mean, it’s crazy thing.

[00:18:02] Richard Matthews: That’s awesome.

[00:18:02] Aaron Rubin: Yeah, you get the benefit several times, but you have to think about things in terms of not just charitable in a state, but also income tax and investing. So once you get your mind around all those three things and how they all work together, you can create some really interesting situations.

[00:18:19] Richard Matthews: That’s why people call you because you know how to do that.

[00:18:24] Aaron Rubin: Yeah, I mean, don’t get me wrong, I leverage, you know, I’m an attorney, but I for sure leverage my relationships with other attorneys and I don’t do the illegal work cuz it’s so difficult. And you gotta have a team in place that knows what they’re doing.

[00:18:39] You have to have your Justice League or your Avengers. Right?

[00:18:44] Richard Matthews: People that make it happen.

[00:18:46] Aaron Rubin: Yeah. You can’t go it alone. There’s no way.

[00:18:49] Richard Matthews: So where is the dollar amount level of like, tax burden that starts becoming an interesting thing to entertain?

[00:18:58] Aaron Rubin: Yeah. You know, I think it’s general rule. You know, if you have a million dollars that you wanna put into, you know, a charitable trust that I think it around a million is when it starts making sense.

[00:19:08] Richard Matthews: So that’s how much money, was that your tax burden, if your tax burden is over a million dollars, or the amount of money you wanna put in is million dollars?

[00:19:16] Aaron Rubin: No, you sort of gotta, if the money you’re gonna put into, so I would say you really wanna be in the highest tax bracket, whatever it is. And so today, you know, the taxable income on the highest tax bracket I think starts 570 some, I mean, I’d have to go back and look at it, but you know, once you get over half a million dollars of adjusted gross income now using some of those charitable planning tools makes sense. And again, the bigger the number, the more it makes sense.

[00:19:42] Richard Matthews: Yeah. Because they’re, I imagine the costs to run it don’t change that much if the number goes up a lot cuz you have your team already.

[00:19:52] Aaron Rubin: Right. So That’s absolutely correct. If it’s a $5 million trust or a $10 million trust, the tax return is gonna be about the same cost.

[00:20:00] The prep of the documents is gonna be about the same cost. You know, you’re right. That’s exactly correct.

[00:20:07] Richard Matthews: Yeah. So, the amount of money that you’re going to put into it goes up, it just gets more attractive.

[00:20:13] Aaron Rubin: Right. Right. Be because as a percentage of what you’re using, it goes down. Right. So, it makes way more sense.

[00:20:19] Richard Matthews: That’s really cool. Yeah, I’d never even like, consider any of those things. Like my goal is to get into that tax bracket at some point. You know, in the next or so, we’re not there yet, but it’s useful to know. So I wanna talk about the the flip side of your fatal flaw, right?

[00:20:34] So your superpower is one side. The flip side of that coin is your is fatal flaw. Just like every Superman has a cyptonite or Wonder Woman can’t remove her bracelets of victory without going mad. You probably have a flaw that’s held you back and growing your business, something that you struggled with.

[00:20:45] For me, it was perfectionism for a long time, sometimes still is you know, it keep me from shipping product. Or the other one was a lack of self-care that I struggled with for good five years at the beginning of my career where I didn’t have good relationships with boundaries for my clients or good relationships with boundaries with time.

[00:20:59] So I would just work myself death. I once tried not sleeping for three days. That’s not a good idea. Just in case you were wondering. But the question essentially is like, more important than like, what the flaw is is how did you work to, or how are you working to overcome it so that it doesn’t hold you back and you can now continue to grow.

[00:21:15] Aaron Rubin: Yeah. So for me it’s, I always have lots of ideas and I’m always talking to clients about different things that we want to do. And my problem is I talk so much about them that I often, like, I lose track. And so losing track of things and sort of letting balls drop has been an issue with me.

[00:21:37] And the way that we’ve kind of gotten around that is one, I leverage technology as much as I can to remind me of like, Hey, you know, blinking light, you know, you said this, you need to perform on this. Or, you know, we just hired someone in a new role for our company and she’s fantastic.

[00:21:55] And her job is to make sure that nothing falls with the crack. So she’s sort of on meetings with me, and when I say things to the client, like, Oh yeah, you know, this is what we should be doing. We need to look at, you know, we’ll have to get back to you on this. You know, she’s the one that will email me for two days from then be like, hey, did you ever deliver this?

[00:22:12] You know, was this done? And it’s like, ah, okay, great. And whatever I can delegate to her, she’ll do, and then whatever I need to do, you know, she’s on top of me being like, No, you need to do this.

[00:22:21] Richard Matthews: That’s awesome. Yeah, I just hired someone in a very similar role cuz we run a podcast production agency. And one of my problems with that agency is I was still doing a lot of the customer communication back and forth between like my production team and the client. And I would miss things because I’m busy trying to grow the company. And I was like, I need someone whose job is to be the customer advocate, so to speak.

[00:22:44] That everything that the customer asks for or needs to do gets communicated clear to the team and back and forth to the customers. Anyways, have that person in place now and is really wonderful. So, I always tell people, or at least myself is you gotta either hire or have tools that show up your weaknesses, right? Not necessarily that you have to fix them, but you have to have some way to mitigate them.

[00:23:09] Aaron Rubin: Yeah. And whenever I meet with a new client or client with her on there, you know, it’s like, Hey, I just wanted you to know this is our person. She’s there to make sure that you have a good experience. And no one’s ever been like, you know, Oh, I don’t know about that. Everyone wants a better experience. So, you know, it’s, it’s been great.

[00:23:26] Richard Matthews: I’ve taken to calling her in our position the customer advocacy or customer advocate. I was like, She’s your advocate in the company that like she’s on, like, not that we’re on different sides, but her job is to just make sure you have a great experience. So yeah, that’s a cool hire.

[00:23:43] Aaron Rubin: Yeah. Maybe she needs to be an ombudsman who were they sort of represent, you know, the people. I always was fascinated with the word. So there we go.

[00:23:55] Richard Matthews: Yeah. That’s awesome. So I wanna talk then a little bit about your common enemy. Right. And every superhero has an arch nemesis, right?

[00:24:02] And it’s a thing that they constantly have to fight against in their world. And in the world of business, I like to put in the context of your clients, and it’s a mindset or a flaw that your clients come to you with that if you had a magic wand and you could just pop them on the head as soon as they signed on the dotted line and not have to deal with that.

[00:24:19]What is the arch nemesis or the common enemy, so to speak, that you have to fight to overcome with all of your clients as they come in.

[00:24:27] Aaron Rubin: Yeah, so I like to think it’s the IRS, you know, truthfully, you know, I think oftentimes I think we demonize the IRS more than we should. Cuz honestly, I mean, the IRS doesn’t pass the laws.

[00:24:41] They actually, they do enforce them and they do write regulations under the Department of Treasury. Really to meet congress is the enemy, but it’s hard to mobilize against Congress. The IRS people understand. So I mean, for me, a lot of it is the complexity surrounding the tax code.

[00:25:02] Now of course if it wasn’t as complex, then I would be out of a job. But to me, we’ll say the common enemy is the IRS or maybe the Department of Treasury. Maybe I’ll feel better about the Department of Treasury. .

[00:25:16] Richard Matthews: It’s interesting too, cuz like our tax system. I think, the support system that exists to help people do their taxes is something like a $4.6 billion a year industry or something less last time I looked at it, which is massive. And it just speaks to the complexity of our tax code. And I’ve always been one of those, on the political side of the scale.

[00:25:38] There’s gotta be a simpler way to run taxes, than what we have because it is really complicated and doesn’t seem to have a lot to do with how much someone actually consumes in the economy and the structures that we’re using. And it seems very arbitrary and I feel like it could be a lot simpler, but I don’t know how to fix that. So that’s not a discussion I have a lot. I just think it’s complicated.

[00:26:00] Aaron Rubin: Yeah. You know, I don’t know a lot about comparative tax systems, but you know, again, I do know that there’s pretty heavy taxation. If you look at countries like Europe and, and the VAT which is, you know, again, I think more of a consumption type of tax. So yeah, it’s a tough one.

[00:26:17] Richard Matthews: Yeah. I wanna talk about the flip side then, right? So if you’re common enemy or the arch nemesis is the IRS and the tax code, the driving force is what you fight for, right? So just like Spider-Man fights to save New York, or Batman fights to save Gotham, or you know, Google fights to index and categorize all the world’s information.

[00:26:31] What is it that you fight for with your tax practice and your wealth management services?

[00:26:37] Aaron Rubin: Yeah, so what we’re really trying to fight for is for an individual to keep more of their own wealth so that they can make the world a better place, however they see fit. And you know, for a lot of our clients that’s philanthropy.

[00:26:55] And we’re happy to support that. And for some it’s, you know, taking care of kids or grandkids or again, a lot of time they do wanna do good in the world. So I always tell them, you know, and sometimes I think some clients are a little bit. I don’t know, they don’t feel good about, oh gosh, I’m getting outta tax.

[00:27:13] I’ve made so much money, you know, I should be paying in, and that’s true to an extent, but you know, to me it’s, you know, who knows what to spend their money on bettering the community. Is it the US government? Or state of California, or is it you? And so if you wanna go out there and make an impact, and I give an example of autism research.

[00:27:36] You know, I have another client who’s really passionate about L G B T homelessness. And so they’re growing out there making really big differences. And you know, for me that’s awesome. Love doing it.

[00:27:49] Richard Matthews: Yeah. So I have a framework you might be able to share with clients on that. And I call it first party spending, second party spending, and third party spending. And so first party spending is when you have money that you’re going to spend on something for yourself. And when you do that, you care about both the price and the value.

[00:28:07] Second party spending is when you’re going to spend your money on something for someone else. And that means you care about the price, but you don’t necessarily care about the value as much cuz it’s not something that you’re gonna use. And third party spending is when you’re gonna spend someone else’s money on something that’s not for you. So you don’t care about the price or the value.

[00:28:26] And all government spending, by definition is third party spending. So they don’t care about price or value. So they will never put the same care and thought into spending that money as you will in deploying it.

[00:28:42] Aaron Rubin: Yeah, absolutely. No, that’s great. That’s absolutely true too. Yeah, it’s one of those things that was like, because I’ve had that discussion a few times with people like, well, you know, if you earn more income, why would you want to reduce your tax burden? And I’m like, because the government is just always going to be third party spending it because it just has to be by definition and just human nature says that it’s not ever going to be spent as well or as efficiently as someone who’s deploying it themselves for things that they care about. So it’s just a better use of resources.

[00:29:14] Yep. No, I totally agree. That’s great. Great way to think about it.

[00:29:18] Richard Matthews: So I wanna talk about some practical things. I call this the hero’s tool belt. And just like every superhero has a tool belt with awesome gadgets like their batarang or their super hammer they can spin around and fly with.

[00:29:30] I wanna talk about the top one or two tools that you use every day in your business. Could be anything from your note pad to your calendar, to something you use for your marketing tools or something you use to actually do your service delivery. Something you think is essential to getting your job done on a daily basis.

[00:29:45] Aaron Rubin: So, I mean, email is my big thing and so I am one of those people that use their emails as also their to-do list. So again, I talk about leverage technology to make sure things don’t fall off my plate again, I definitely use email like that. So my inbox is what I live by.

[00:30:06] We’re also, right now, we’re making really big enhancements to our CRM, our client relationship manager. So we’ve adopted Salesforce, which is this huge, vast pit for which you can spend endless amounts of time, but we’re spening a lot of time, and we we’re getting help on it too.

[00:30:30] And that is gonna be huge for us cuz this is where we’re gonna keep our notes. This is where, you know, we’re gonna be able to have business continuity. And I’m super, super excited about it and tracking projects and it’s gonna be amazing. But we’re just starting to use it. We’re just starting to leverage it the right way and it’s gonna be so good.

[00:30:48] Richard Matthews: So we just did something very similar. We’re using Click up in the same way. Click Up is a similar type system, and so we’re using it as a CRM and a project management and process documentation. And we’re moving it from where we had it all sort of in like disparate systems all into, like this one, we went from being like all of our delivery was, you know, like just on time kind of thing to like, we’re a week or two weeks ahead on everything and everything’s getting documented well and we can keep track of everything and there’s a lot of continuity.

[00:31:13] My only point in saying that is just that like it’s a wonderful thing to finally get a system, whatever it is, whether it’s ClickUp or you know, Salesforce in place to sort of track everything that’s going on. It had a huge impact on my business. I hope it has the same for yours as you get it implemented.

[00:31:26] Aaron Rubin: Yeah. It’s funny, I was, you know, I was just at Saster last week which is a trade thing for softwares and service companies. ClickUp was there and very popular. So yeah, you are not alone in your ClickUp party.

[00:31:40] Richard Matthews: They are. And it’s an impressive piece of software. And they’re doing good to work with it. So, you know using it as a CRM is a bit of a stretch for like their use case. But it does work well. And they’re making some changes to it, I think in their, whatever their next version is that’s coming out.

[00:31:55] They’re gonna take their, I guess, the baseline of their database and change a little bit of its structure. So it’s not all task focused, and you can have them be, you know, represent people instead of representing a task or represent a company instead of representing a task. But right now we’re just like, I’ve modified their structure to use a task to work as a CRM.

[00:32:16] But anyways, it’s like a lot of people are doing that, so they were like, hey, maybe we’ll just make that part of the core.

[00:32:23] Aaron Rubin: Right. When your customers are telling you something, maybe, you know, you start to listen, I guess.

[00:32:27] Richard Matthews: Absolutely.

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[00:33:56] And now back to the Hero Show.

[00:33:58] So I wanna talk a little bit about your own personal heroes, right? Every hero has their mentors, just like Frodo had Gandalf or Luke had Obi Wan Kenobi, or Robert Kiyosaki had his rich dad, or even Spider-Man who had his Uncle Ben, in the newest movie, it’s his Aunt. May. Who were some of your heroes? Were they real life mentors, you know, peers, couple years ahead of you?

[00:34:14] Or maybe authors or speakers? And how important were they to what you have accomplished so far in growing your practice?

[00:34:21] Aaron Rubin: Yeah. You know, I’d say, you know, I’ve had great mentors, to be honest with you. Going back to when I was in college. But, you know, I’d say, my father-in-law has been a huge mentor for me.

[00:34:34] You know, he’s been in the industry for 40 plus years. And, you know, said, okay, you know, starting in 2009 when I joined him he said, okay, now you’re gonna be sitting in my meetings for the next couple years and that’s what we did. And I learned a lot from him.

[00:34:52] And he introduced me to the whole thing. So he wrote a book a long time ago that ended up getting several new editions with new authors on it. Called the Prudent Investors Guide to Investing and gave me that book when I was my third year of law school and one weekend I read through the whole thing and it was like eye opening and amazing.

[00:35:15] So it was sort of that this, whoa, this is how it actually works. And it was crazy. It completely blew my mind. As someone who’s only experienced previously that had been bankrupt, Marvel Stock . You know, I was like, ah, okay, that’s how that works.

[00:35:33] Richard Matthews: Okay. You’re like, Oh, I get it now. That’s awesome. And you know, I’ve always been a big fan of just sort of understanding the people that have an influence on how you do what you do, because every hero has their mentors. And it always reminds me to think this, like, those people don’t always even know that you would think of them as a mentor.

[00:35:51] So I was like, there’s probably people out there who look at me and think of me as their hero, and I always think to myself, am I acting in a way that’s worthy of that?

[00:36:02] Aaron Rubin: Yeah. Well, I’ll tell you, so I wrote a book a couple years back called Financial Adulting. And for sure put, you know, it was so good that some actual authors stole my title just last year and used financial adulting where, I guess, they wrote their own book on it, but they actually had like a real publisher. So you know, I was just self-publishing.

[00:36:23] But in my version of the book, in the true version as I like to call it it I definitely thanked him acknowledgement and you know, all that good stuff. So he knows. He should know. He should know.

[00:36:35] Richard Matthews: So I wanna talk to you about some of your guiding principles, right? One of the things that makes heroes heroic is that they live by a code. For instance, Batman never kills his enemies, he only ever puts him in Arkham Asylum. So as we wrap up the interview, I wanna talk about the top one or maybe two principles that you live your life by, run your business by. Maybe something you wish you knew when you first started out in this business.

[00:36:57] Aaron Rubin: Oh, okay. So also, I’ll say two. The first is you have to be honest at all times, at all times. Because if you try to start making stuff up, you’re gonna destroy your reputation, right? It’s that old adage, you know, reputation takes a lifetime bill in a minute to destroy.

[00:37:16] So you really have to be careful, you know, make sure that you are really telling the absolute truth on everything. That’s a must. I would say the other thing that I had kinda learned, it took me a while to get to was you have to be yourself at all times as well. And so when I first started doing this advisory thing, after spending three years in public accounting, you know, for the first several years I spent much of my time trying to be what I thought was the right advisor instead of being myself.

[00:37:50] And so, you know, I spun my wheels a lot, trying to be something that I wasn’t. And then eventually I was like, wait a second. Being yourself means that, you know, there’s many people who aren’t gonna like you, and they aren’t gonna work with you because of that.

[00:38:06] But people can sense authenticity, and people would much rather be someone who’s authentic than not.

[00:38:13] Richard Matthews: Yeah, yeah. And the people who aren’t gonna like you weren’t gonna like you anyways. And they weren’t your clients.

[00:38:19] Aaron Rubin: There you go. There you go. But I think, I think when we’re younger in our careers, I think we’re always trying to play the part. And then at some point we get to, oh, hey, I just gotta be myself. So when get there it’s much easier.

[00:38:35] Richard Matthews: Yeah. It’s easier to be yourself, so you don’t have to try, you just be you.

[00:38:42] Aaron Rubin: Yeah. I totally agree.

[00:38:44] Richard Matthews: And I know with the honesty thing, one of the things that has struck me is like that we’re on episode like 230 or some number like that with this show.

[00:38:52] And I would say probably roughly 80 plus percent of the people I asked that question to have some form of answer that comes back to honesty or integrity. Which always has struck me as really interesting because culturally we have this view that entrepreneurs are villains. And it’s actually why we run this shows because I’m at the superior thought opinion that entrepreneurs are the heroes and they’re the ones that are changing the world to make it better.

[00:39:13] And it’s just interesting to me how common of a thing that entrepreneurs like, they’re very actively thinking to themselves and running their business by a foundational principle of integrity and honesty.

[00:39:26] Aaron Rubin: Yeah. Yeah. Well, I think we’ve all had the experience where we weren’t dealing with someone like that. And that isn’t the experience we wanna give anybody else. And I mean, unless we’re really jerks.

[00:39:39] Richard Matthews: So I have a theory, a friend of mine, I’ve been talking about this, about why it’s so pervasive culturally to think of entrepreneurs as villa villains.

[00:39:47] Cuz like you can’t turn on a kid’s TV show without the bad guy being some version of entrepreneurs spills oil on ducks for money, right? And I think the reason why that is the case is because it’s not normal. And normal doesn’t make good story telling. Things on opposite ends of the spectrum makes for good storytelling and because it makes good storytelling to have an evil entrepreneur or a really good entrepreneur one way or the other you have to have the extremes for the good storytelling that you know, storytelling and movies and TV shows and books and everything makes it sort of be this like cultural perception that entrepreneurs are the bad guy and that’s really just not the case.

[00:40:26] So that’s my theory. I don’t know if it’s true or not, but that’s my theory and why that happens.

[00:40:30] Aaron Rubin: Yeah. I think that’s viable. I think also that it’s hard to be an entrepreneur, right? It’s hard to wake up with that mission every morning and, you can’t let anything go.

[00:40:47] And I think for people who don’t necessarily have that mentality, and they see a very successful entrepreneur. I think part of it is when you see someone who’s super successful, you have to ask, everyone has to ask themselves, why aren’t I as successful as they are?

[00:41:09] And I do this, right? I mean, like, I’m not as successful as Jeff Bezos is. I don’t think I’ll ever will be. You know, and I think if you are an entrepreneur, you understand, you know, that people like Jeff Bezos, like he, man, he risked everything. Meaning, he had a mission and he wouldn’t stop.

[00:41:29] I mean, I don’t think his personal relationships are anything to write home about. Meaning, he either documented things about him. But people like that are just, you know, they’re a different breed. And I think it’s a shortcut, I think for people who aren’t as entrepreneurial to be like, well, they must be doing something wrong.

[00:41:54] Or they’re bad or I mean, it’s ill begotten in some sense. I don’t know. I mean, for me, I’m just like, I’m not willing to do the things that Jeff Bezos was willing to do. And I’m not as smart as Jeff Bezos, but that’s okay. You know, and he’s gonna do his thing and I’m gonna do mine.

[00:42:17] Richard Matthews: Yeah. And you both bring value.

[00:42:21] Aaron Rubin: Yeah. And, you know, I love the life I’ve created and I’m fine with it.

[00:42:28] Richard Matthews: Absolutely. And I think that is a great place to wrap our interview too. So I do finish every interview with a simple challenge. I call it the hero’s challenge. And I do this to get access to stories I might not otherwise find on my own. Cause not everyone is out doing the podcast rounds like you and I might do. So the question is simple. Do you have someone in your life or in your network who you think has a cool entrepreneurial story?

[00:42:45] Who are they? First names are fine. And why do you think they should come share their story with us here on the Hero Show? The first person that comes to mind for you.

[00:42:54] Aaron Rubin: First person that comes to mind with me is, so his name’s Bryce Emo. He Just founded a company few months ago called Side Car Finance. And what he does is he helps people who are at Pre IPO companies Find the right partners with, to sell or otherwise get liquidity for their shares, their private shares.

[00:43:18] And so he started with a lender you know, several years ago and, you know, helped them raise tons of money. It was super successful and now he’s out there sort of on the opposite side of the transaction, helping people at the company is negotiate against sort of his former employer and their employer as a group as well.

[00:43:42] And again, I don’t wanna demonize the lenders, right, because they’re super important. But he’s sort of now on the side of the little guy who’s now negotiating against the lenders. So he’s flipped his side, which I thought was super cool.

[00:43:56] And he’s got a really awesome business model. I mean, he’s great. He’s so smart. He’s awesome. Total man crush right here.

[00:44:06] Richard Matthews: That’s awesome. We’ll see if we can reach out afterwards and maybe get an introduction to him. Get him on the show. They don’t always say yes, but sometimes when they do, we get cool interviews and get to hear how some different businesses are founded, so I appreciate that.

[00:44:16] But in comic books, there’s always the crowd of people at the end who are cheering and clapping for the acts of heroism. And so our analogous to that on this show. Where can people find you if they need your help in the future? Where can they light up the bat signal, so to speak and say, hey Aaron we’d like to get your help with our pre IPO stock.

[00:44:29] And I think more importantly, or who are the right types of people to reach out and actually light up the bat signal and ask for your help.

[00:44:34] Aaron Rubin: Yeah, so we are everywhere. So we’re at Twitter WRPAdvisory. We’re on Facebook, WRPWealth. We are on TikTok, I tell you, IPOGraphs is our handle at TikTok.

[00:44:49] And of course, LinkedIn there as well. Our blog is phenomenal. If you have any questions of information on 83(b) elections or if you don’t know what 83(b) elections is, and you wanna know, that’s where you had our blogs have our chocolate great information.

[00:45:04] And if you wanted to, you could schedule an appointment with me on our website . So, you know, in terms of, people who come see me, usually it’s people, those who are in their D round of financing maybe, and again, maybe even beyond, sometimes the C round makes sense. But again, when, especially if you’re moving jobs.

[00:45:25] You know, you’re coming to a new space and you have choices with your stock options. It’s a good idea to talk to someone, even if from a wealth perspective it doesn’t work out. Our tax team can almost always help you too. So again, we have a pretty great offering.

[00:45:40] Richard Matthews: Awesome. Well, I do appreciate you coming on and sharing your story with us today, Aaron. It was been fascinating. I’ve learned quite a bit. Hopefully our audience did as well. Do you have any final words of wisdom for my audience befire I hit this stop record button?

[00:45:50] Aaron Rubin: Yes, Yes. I have to have something. Yeah, no, my final words of wisdom are seek tax help. Don’t try to do it alone because it’s complicated and you don’t wanna mess it up. And there’s some choices you can make early on that could really affect, you know, how much you get to keep later down the road. So once you get some stock options, you know, more than, let’s say, 20, 25,000 shares of whatever, you know, go see a tax professional, it’s worth awhile.

[00:46:19] Richard Matthews: Awesome. Thank you very much, Aaron. Appreciate it.