Latest / trading places / OpenAI $110B Raise, Stripe at $159B, and the Donor Money Tax Hack VCs Use | Trading Places Podcast E25
Transcript
- 0:00Personally, myself, I have booked more than $5,000,000
- 0:03worth of tax credits using this strategy in the past couple
- 0:05years. Donor advice funds are
- 0:07essentially twice as tax efficient.
- 0:10The tax deduction that you receive, depending on the asset
- 0:12can be upwards of twice as large compared to a private
- 0:15foundation. I think what's happening now is
- 0:18basically just the market is taking a maybe an overreaction
- 0:21to every new AI agents that comes out, whether it's Claude
- 0:25or someone else. Good morning and welcome to the
- 0:5025th episode of Trading Places, the world's most horrible,
- 0:54terrible, bad podcast. Aman, you're back from Italy,
- 0:58back from the Olympics. I've got a dog in my lap here.
- 1:02I see if sides now that the USA won.
- 1:05You, you bandwagon fan. You.
- 1:09No, Well, it's the benefits of being a dual citizen.
- 1:12You know, you can, you can root Canada and they're when they're
- 1:15favored. And now I'm flipping over to
- 1:16team US. And it's interesting.
- 1:18I was travelling as both a Canadian and an American because
- 1:21for hockey, I grew up in Canada playing hockey, so I was rooting
- 1:23for their Canadian team, but for everything else that was
- 1:26traveling as an American. So I'm back on back on team.
- 1:29It's a good, good week to be an American this week, Dave.
- 1:31Hockey wins and then you get the women's one.
- 1:35The Men 1 is just a good good week I think to be on TVUSA.
- 1:38Little bit of fact I'm on, it was a pretty good hockey player.
- 1:42And am I correct you actually played the Russians?
- 1:46As a junior, I think semi pro by hockey and play for a junior
- 1:50team. Canada at a time when the Soviet
- 1:52Union was just coming undone. The Soviets that we skated
- 1:56against where the the fastest, biggest, strongest players I've
- 1:59ever seen. I must break.
- 2:07You Aman what's been happening with open AI and fundraising.
- 2:12Kind of a big deal, huh? Yeah, I think on the fundraising
- 2:16side, they are dialing in a $110 billion raid. $110 billion, the
- 2:26biggest raise of all time. It's it's bigger than any public
- 2:31IPO. It's bigger than any private.
- 2:33Raise yeah up until now the the biggest fundraising round of all
- 2:38time it actually was open AI about a about a year ago when
- 2:41they raised 40 billion on 300, the biggest IPO of all time it's
- 2:46basically tied between Alibaba and Saudi Aramco.
- 2:49I think Saudi Aramco has the official record of a 25.6, but
- 2:52that was with the green shoe and some friends and family money
- 2:56coming from the the the Saudi world family and their friends.
- 3:00But that's 25 billion. This is $110 billion.
- 3:04And so it's going to be I did a 730 pre money.
- 3:08So I guess it's not put some like 840 post money.
- 3:10Biggest biggest fundraising of all time by probably an order of
- 3:13free acts breaking their old record and four times bigger
- 3:16than the biggest IPO. And like, basically more money
- 3:19than was entirely raised in venture capital a few years
- 3:23back, right? Like one deal is bigger than the
- 3:26entire year of venture up until like a few years ago, I guess,
- 3:30yeah. Amazing.
- 3:31I guess that's right. Although they're kind of they're
- 3:33kind of cheating because they're putting a lot of money in from
- 3:35strategic. So just to just to recap why I
- 3:38think this is such a big deal for opening AII think they're
- 3:40actually broadening their partnership base here.
- 3:43Up until October at 25, this was open AI was basically a wholly
- 3:47owned subsidiary of Microsoft. Microsoft owned at one time 49%
- 3:51of the equity. They they came down to 27% in
- 3:55late October and announced a whole bunch of agreements as
- 3:58essentially the primary frontier model partner for for open AI,
- 4:02including exclusive IP rights through 2032 and up until
- 4:07whenever AGI was announced or whatever, whatever the hell that
- 4:09is. But this is the new money coming
- 4:11in. It is not coming from Microsoft
- 4:14is actually this, these are the three big partners.
- 4:16It's Amazon for 50 billion. Now some of that's going to be
- 4:20in services, some of that's going to be in cash.
- 4:22It's not all committed right out of the gate, but in milestones.
- 4:24But it's going to make, I think by my math, Amazon is going to
- 4:27be a 7 to 8% equity owner in open AI.
- 4:30So they'll be right behind Microsoft in the low 20s and
- 4:33against the open AI foundation of the low 20s.
- 4:35Then you got some employees and you know, whoever, whatever Sam
- 4:38ends up owning, but Amazon's going to be a huge player.
- 4:41Inviga's in for 30 billion, Softbank's in for 30 billion.
- 4:44And I guess the good news is if you're, you know, if you're open
- 4:47AI, it's like, hey, I can raise a lot of money.
- 4:49But they, they leaked a bunch of financials as a part of a
- 4:52fundraising. And David, I think he and I have
- 4:54been in this board meeting before where somebody says, Hey,
- 4:57I'm going to double my spend. You know, in this case it's 665
- 5:00billion by 2030. But the good news is I'm in
- 5:03revenue and the revenue is 280 billion by 2030.
- 5:09But I don't know exactly. I'm gonna get there.
- 5:10I need the money now. I'm gonna give you the money
- 5:12later. The money later is gonna be some
- 5:14combination of consumer modernization search.
- 5:16It's gonna be it's hardware, it's ads, it's everything else.
- 5:21And they're also increasing their estimate cash burn to 111
- 5:23billion or by 111 billion now through 2030.
- 5:26So they're gonna raise a lot more money.
- 5:28They're spending a lot more money and they're promising a
- 5:30lot more on the back end. But this is, again, we've all
- 5:33been in this board meeting, right?
- 5:35I don't think I've been in this board meeting.
- 5:36I think that is like high stakes poker with a couple of extra
- 5:41zeros, like 5 more zeros than I've ever been in any board
- 5:46meeting for sure. Yeah, fair enough.
- 5:48But man, that is kind of amazing.
- 5:51So, you know, again, in any other Newsweek, that would be
- 5:55stories 1-2 and three and we would be done.
- 6:00But guess what? There's a lot more going on this
- 6:04week. And I think our next four
- 6:09stories are all going to be stories about anthropic.
- 6:15And so let's let's jump into perhaps the least interesting of
- 6:20the four stories, which is Anthropic, who recently
- 6:25completed a raise at 350 billion, is now kicking off an
- 6:29employee tender offer of $6 billion.
- 6:32And so employees in Anthropic are now going to be able to cash
- 6:37in five or $6 billion worth of their equity.
- 6:40Anybody who's been to the company for more than 12 months
- 6:43and they're certainly demand for those shares.
- 6:45So that's, that's not a problem. I think real estate prices in
- 6:49San Francisco just went through the roof.
- 6:52A lot of a lot of happy real estate agents in San Francisco.
- 6:56We're going to be very busy over the next six months, I think.
- 7:00How many? How many Decca millionaires did
- 7:03anthropic? I don't know.
- 7:05And you know, a couple of that maybe 10,000 Decca millionaires
- 7:09at at NVIDIA. That might be another, you know,
- 7:11anthropic and. Certainly hundreds, if not
- 7:15thousands of people are now going to be millionaires of some
- 7:20sort and may be correct, 10 millionaires.
- 7:21Perhaps. This is the least interesting
- 7:26anthropic story this week. And that's what's kind of crazy.
- 7:33So this was being threatened all week, but now it's official.
- 7:37The Pentagon has declared Anthropic a threat to national
- 7:42security, a supply chain risk. And Defense Secretary Pete
- 7:47Hegseth, who used to be a Fox News commentator, is now
- 7:51blocking all federal agencies and contractors from doing
- 7:54business with the company. And not only that, all other
- 7:57companies that have business with the military from doing
- 8:00business with Anthropic as well. And I'm not, I'm not sure I know
- 8:06all of the reasons here, but I think there was like
- 8:08commentation, comments about two specific areas that Anthropic
- 8:14CEO Dario Amaday was not OK with.
- 8:17One was mass surveillance and the other was autonomous use of
- 8:22weapons of mass destruction or at least significant weapons.
- 8:25So whether that's nuclear or other, my sort of on target
- 8:29there is that your read on the situation as well.
- 8:31Yes, I think so. There's an ongoing debate over
- 8:34the, I guess the use of Anthropic is this way.
- 8:37Anthropic is a major supplier of the US military, has been for a
- 8:40while, right? I think Dario has said, and he,
- 8:44he has said as a condition for continued use of Anthropic, he
- 8:47really, he drew those two red lines.
- 8:48In fact, the first one was mass surveillance of U.S. citizens.
- 8:51I believe it wasn't even mass surveillance, but just US
- 8:53surveillance. Specifically U.S. citizens.
- 8:55You're correct. Yeah, right.
- 8:57And that's illegal, by the way. So by asking for something like
- 9:00that hey you if I if I can do to sell me you my technology don't
- 9:04use it to mass surveil U.S. citizens, which already is a
- 9:07violation of the law kind of a. Little bar, right?
- 9:09Don't. I'm going to hold the line at
- 9:12things that are already clearly illegal.
- 9:15Yeah, give me that one and then and then the second one I guess
- 9:19is maybe a bit more debatable on what is autonomous use of
- 9:22weapons and right, None by the way, if I'm Dario, it's not an
- 9:27unreasonable. Question to ask.
- 9:28I'm like, those two don't sound crazy to me.
- 9:31Like, hey, don't let robots control nuclear weapons and
- 9:34don't mass surveil the US public.
- 9:36I'm like, yeah, pretty low bar, OK, I agree with that.
- 9:40But DoD said no way man, you're being super woke.
- 9:44Really. Well, I think Pentagon
- 9:46reasonable, reasonable position would be we are buying your
- 9:49technology just like we buy technology from Boeing.
- 9:53Boeing doesn't tell us how to fly our planes.
- 9:54Let us you know, in the defense of democracy and freedom,
- 9:57freedom, use it the way that the military generals supervised by
- 10:01Congress and the commander chief were supposed to do it.
- 10:03But at the same time, you know, I think the, the, the, the
- 10:07unreasonable response is, well, if you're not, if you're going
- 10:09to sell me your technology with terms and conditions, you an
- 10:12American, you know, violator of the Constitution.
- 10:15You are. Blacklisting you and your supply
- 10:17chain risk? That does seem like hardball
- 10:20negotiations. I'm, I'm hoping that they come
- 10:21to some kind of reasonable, you know, that they maybe they're
- 10:24negotiating and that they're going to have the, some kind of
- 10:26deal here because I think the US military will work better with
- 10:28AI technology. In fact, I'm sure that will, we
- 10:30don't want to be, we don't want the military left behind in AI
- 10:32technology and adoption. But I think Anthropics had some
- 10:35very reasonable requests on how to use your technology and
- 10:37they're the experts where AI can go wrong, right?
- 10:38So you think you would, you'd think you'd have some
- 10:40accommodation and not, and not just, you know, blacklist them.
- 10:44But I, I don't know of all the insurance and outs on the
- 10:46negotiation. What's the dog's name?
- 10:52Max. Hey, Janelle.
- 10:55What's wrong with Wolfie? I can hear him barking.
- 10:58Is he OK? Wolfie's fine, honey, Wolfie's
- 11:00just fine. What are you the?
- 11:06First appearance are dead. Well, never one to miss an
- 11:10opportunity, Sam and Open AI are grabbing that bag.
- 11:15And so within hours of this announcement, Open AI has
- 11:19reached an agreement with Defense Department to pick up, I
- 11:23believe a $200 million contracts, which which sort of
- 11:26seems like chump change these days, right?
- 11:28We're talking like billions, hundreds of $1,000,000, like
- 11:30$200 million contract. Oh, yeah, like, like, that's
- 11:33nothing. But it is sort of like having
- 11:37one of the two major AI players flip over and take up that
- 11:42contract. I guess Sam.
- 11:44Sam must have been ready. What do you think?
- 11:47Daria, you've you've you've dropped the ball there.
- 11:49Are you here? Let me let me pick it up for
- 11:52you. Good for Sam, I guess.
- 11:54I mean, you think with a trillion dollar Pentagon budget
- 11:56this year, there's going to be you know, a lot of money spent
- 11:58on AI providers and it hopefully it's not just these two.
- 12:01Hopefully they've got, you know, many different vendors, but I
- 12:04wonder if Open AI is going to have the same requests.
- 12:07I guess not. I guess they're going to allow
- 12:08the attendant. To I thought, I thought they
- 12:10did. I thought Sam was kind of in
- 12:12other tweets agreeing with, with Anthropic's position on mass
- 12:18surveillance and autonomous use of of weapons, or at least
- 12:22autonomous use of nuclear weapons.
- 12:24But Sam seems to have been opportunistic in in saying, hey,
- 12:27you know what, we're going to step into the breach here.
- 12:30And I I think this kind of is harkening back to some, you
- 12:33know, woke, not woke positioning.
- 12:36Maybe I don't, I don't know if that's overplayed, but probably
- 12:40anthropic is a little bit more left of center and open the eye,
- 12:43maybe not right of center, but maybe a little bit more willing
- 12:46to play ball with the government.
- 12:48Is that your read? You know, it just may be a
- 12:51negotiating, it may be some name calling in a in a negotiation.
- 12:54I don't I don't really know how the ideology lines up here other
- 12:56than the same stuff that being opportunistic.
- 13:00I think he is, you know, I think the benefits of having multiple
- 13:03vendors in this game and I don't know where Brock is rather, but
- 13:06I would imagine having multiple players in this game are are
- 13:08good for the Pentagon and and that's what they would want to
- 13:10do. This is the procurement best
- 13:11practice. I've got to think some of the
- 13:13calling and the personal stuff is a little bit of Trump being
- 13:16Trump and a little bit of maybe negotiating back and forth.
- 13:19Yeah, And I think you're right. I think there was also some
- 13:22announcements earlier in the week about Grok being selected
- 13:26for a lot of Defense Department contracts as well, and that
- 13:29maybe Elon had the inside track on some of that.
- 13:32And certainly, you know, before when Elon was more engaged with
- 13:36the government, people thought, you know, he's going to have a
- 13:38lot more role with the government there.
- 13:41All right, our fourth story involving Anthropic this week.
- 13:47Couple things going on here. Anthropic has been releasing
- 13:49plug insurance that are category specific, industry specific.
- 13:54I think previously in insurtech and in wealth management and a
- 13:58couple other areas. And those resulted in public
- 14:01companies in those areas, stock prices getting crushed.
- 14:06And then this piece from Centrini Research came out about
- 14:09the 2028 global intelligence crisis.
- 14:11And I'm on maybe you can like give us a little bit of read
- 14:15between the lines about what's going on here.
- 14:18Is this about there being an AI bubble or not being a bubble or
- 14:21too much bullishness or bearishness?
- 14:23What's what's the Centrini memo all about?
- 14:26Yeah. Well, I think the let's ground
- 14:28it in some of the some of the facts on sort of the anthropic
- 14:31shake out that you described. So this is I think important
- 14:33because this is the it's driving market sentiment.
- 14:36And with the way that I would, we just talked about Anthropia
- 14:39being the left wing woke the nice guys in AI for a nice guy
- 14:43in AI. They're destroying the entire
- 14:45software sector market cap. They're wiping out probably 20
- 14:49to 30 billion in market cap. They don't doesn't sound very,
- 14:52very nice or sensitive. But so back on February 1, they,
- 14:56they announced a new plug in for Claude Cork, which is their AI
- 15:00agent. And it had some functionality
- 15:03for legal contracts. And you know, the sort of thing
- 15:06that I've been playing with this for six months.
- 15:07So this is not, it wasn't new. I've been playing with Claude
- 15:10'cause I do legal drafts and contracts.
- 15:12This was a feature functionality they had.
- 15:14They just sort of advanced it and super sliced it to this this
- 15:17API on February 1 and look at the share prices that and have
- 15:21you reacted between LegalZoom, Thompson, Reuters, LEXIS, Nexus
- 15:24and then Wolf with Kluwer? They were all down 2530% and you
- 15:28know, within a matter of like days after this new legal plug
- 15:32in went live. And then on the 20th, they they
- 15:34Claude put out new security features And again, the cyber
- 15:39and people knew this in advance. And so there was a little bit of
- 15:41a, a down draft and down trade, but Crowdstrike and Cloudflare
- 15:44and some of these high Octa, some of these high flying
- 15:46cybersecurity SAS companies, kind of, you know, kind of price
- 15:49for everything to go, right. They basically took a big hit in
- 15:52advance of that launch. And then the launch happened,
- 15:53they took another hit and they've kind of recovered since.
- 15:56But you can see the damage being done in these sectors from these
- 15:58new, you know, clawed features. And so I think what's happening
- 16:02now is basically just the market is taking a, the maybe an
- 16:06overreaction to every new AI agent that comes out, whether
- 16:10it's Claude or someone else. And then I think the most recent
- 16:13Citrine memo is essentially A doomsday scenario of what could
- 16:17happen in by 2028 turn course and speed with AI and the
- 16:22picture that it paints is 1 of radically increased
- 16:25productivity, but a lot of job losses, 10% plus unemployment in
- 16:28US concentration of wealth. The S and Pi think they have
- 16:32going down by 38% mainly because of what we just talked about,
- 16:35the 20% reduction of these SAS companies playing out over
- 16:38multiple years and profit is being destroyed.
- 16:41It's just it feels like an AI doomsday scenario.
- 16:43It's like the remember James Cameron's 1984 movie The
- 16:46Terminator. The if you look at the back
- 16:48story for that, you know, that's what it is.
- 16:50It's like AI is far more destructive and malevolent than
- 16:52it is positive. I think of technology as as it's
- 16:55a positive supply side shock like the railroads or like, you
- 16:58know, the telecommunications of competing revolution or you can
- 17:03go back to the automobile. There's always this job loss and
- 17:05profit creation that happens as a result of these things that
- 17:09that happened in tandem, losses and creation.
- 17:11And this just focuses on the negative.
- 17:13And I think the market's taken a very negative approach in the
- 17:15last couple of weeks. And this is just, you know, a
- 17:17manifestation of that. So 1 great question.
- 17:20If you're a founder right now or raising money in IPO, are you on
- 17:23Claude's shit list or not? Like if you, if your product is
- 17:27on a road map, I'm talking lovable or replit, if you're
- 17:30doing something that Claude can do, you better have a good
- 17:33answer for what happens when they launch a plug in or some
- 17:36kind of a feature. Because if you don't have that
- 17:38answer and why your why your business is defended against
- 17:42that kind of a move, then you're going to get discounted in the
- 17:44market by 20 thirty, 40%. Or, or more.
- 17:48Yeah, well, there was, there was a bit of a rebuttal to that
- 17:51Satrine memo by Citadel and I guess they were saying, hey,
- 17:55maybe not quite that bad. Rapid expansion of artificial
- 18:00intelligence unlikely to trigger mass job losses at least some
- 18:03concern that the AI driven labor disruption was really not
- 18:08happening quite just yet, right. And I don't know if I sort of
- 18:14believe the you know AI is going to kill everybody company, but I
- 18:17also don't necessarily believe hey, there's no impact there.
- 18:20I think somewhat notable this past week, Block CEO Jack Dorsey
- 18:24Block, which used to be called Square, is a public company and
- 18:27he announced layoffs of 40% of the company because he said not,
- 18:34hey, we're not doing bad. We because we can't, we can lay
- 18:38off 40% of the company because AI is going to make us so more
- 18:42productive, so much more productive.
- 18:44And I believe the stock price jumped 15 or 20%, maybe more
- 18:47than 20% as a result of those moves.
- 18:50What do you think about that? Who's right on this?
- 18:53Like how much of like job losses is AI related or just like AI is
- 18:58the fall guy for all these job losses and people are just
- 19:01trying to be more productive and, you know, look, cut
- 19:04expenses. Well, you hear a lot of
- 19:06anecdotal evidence about the use of these AI specifically, but
- 19:10maybe just, you know, technology and automation to make the work
- 19:15more efficient. And you hear, you know, Amazon
- 19:17laying off a few thousand here, Alphabet laying off a few
- 19:20thousand there. So far it's been like 1235
- 19:23percent of the workforce at most.
- 19:24It hasn't been anything quite so severe as the 1020 Thirty 40%
- 19:29Doomsday scenario 40. Percent is a lot, right?
- 19:3240% is like, hey I can run my company on half the people.
- 19:36Yeah, exactly. This is the second time I think
- 19:38I've heard something real. Like the first time was Elon
- 19:40Musk at at Twitter and he laid off some of the 580% and the
- 19:44site didn't go down. The one piece of contacts that
- 19:46say just before we get into the who's right or wrong is just as
- 19:49a reminder, let's take block. This is their headcount going
- 19:52back to the last few years. So they hired look at 2018
- 19:56nineteen. They basically tripled the size
- 19:59of the workforce between 2019 and 2023.
- 20:02So all through COVID. They basically hired way ahead
- 20:06of their plan, way ahead of their revenues.
- 20:08And I think there's been a couple years now of just going
- 20:10from that over hired bloats to now, you know, significant
- 20:13reduction. So I don't want to minimize the
- 20:14reduction, but I just say in context, there's a, there's a
- 20:16lot of fat in these organizations that's going away.
- 20:19The overall unemployment rate, it's the point Ken Griffin makes
- 20:22in Centadel. The overall unemployment rate in
- 20:23the US is 4 point, what, 3%? Back in the 80s and 90s when I
- 20:27learned economics, that was full employment, like that was
- 20:30supposed to be a kind of condition of a Golden State or a
- 20:33paradise. Anything below 5% was amazing.
- 20:37So we have a very low unemployment rate.
- 20:38We have software jobs are actually going up, not going
- 20:41down. Anthropic is hiring right now
- 20:43for AI engineers. They're paying according to a
- 20:45million and a half million in starting salaries.
- 20:47So there's a lot of job creation and a lot of jobs that are being
- 20:50that are coming into being. There's also a lot of
- 20:52offsetting, you know, decline and destruction.
- 20:55I think Dorsey's maybe on the more extreme example of what's
- 20:57what is happening or what will happen.
- 21:00But I think on the whole, there's going to be a lot of
- 21:02positive creation over the next five years that we don't yet
- 21:04have our arms around. Just a lot of anxiety around it.
- 21:06But I think that's going to be the that's a positive supply
- 21:09shock that when you get productivity going up, people
- 21:11can do a lot more things, things become a lot more cost
- 21:13effective. And so people find jobs to do.
- 21:15It just hasn't, you know, and it's not showing up the, the AI
- 21:18job description scenario isn't showing up in the macro stats at
- 21:21least at least not yet. So I tend to be on the
- 21:23optimistic side. I think, you know, I think
- 21:25Citadel's got a point and I think the the doomsdayers are,
- 21:28are probably overstating it. Jesus, you're going to kill that
- 21:34guy of. Course, I'm a Terminator.
- 21:37All right, another amazing, but you know, still kind of lower
- 21:41down on our list here. Byte Dance recently valued at
- 21:44550 billion, that's up from where we were looking at it,
- 21:48maybe, I don't know, 3-4 months ago.
- 21:50And it was only valued at the $300 billion evaluation.
- 21:53I think at the time, we were wondering why it wasn't valued
- 21:57more. And I guess now the market is
- 22:01recognizing that and and valuing it appropriately.
- 22:05So $550 billion, that's, that's right up there.
- 22:11I'm on that. Isn't that #4 now #3 on our
- 22:14list? I guess number three behind
- 22:15SpaceX will be #1 right? I guess open alley will be #2.
- 22:19Yeah, the other week. Story, but they're they're the
- 22:22number three most valuable private company in the world.
- 22:25They're they're last round and we covered them in our valuation
- 22:27corner about six months ago. They were at a $330 billion
- 22:32valuation we thought based on the summer parts.
- 22:34Oh, that's gotta be, that's gotta be a buy if you think
- 22:37there's any value to TikTok. And I guess the way I think
- 22:39about the valuation, this is just a, a snapshot of social
- 22:44media companies in both the US and in China.
- 22:48And you can see where Meta is, right?
- 22:49The big, the big blocks are Meta, which is the $101.5
- 22:52trillion social media giants. But on the Y axis is the growth
- 22:56rate and the X axis is the revenues for the company.
- 22:58So you can see where Meta is. And when Bytedance did its
- 23:01evaluation right before evaluation corner, you can see
- 23:04where it landed. It was a much smaller
- 23:06evaluation, but similar revenue and higher growth.
- 23:09So pretty, pretty attractive and if you look at their valuation
- 23:12now, I think they're much closer to where you would think it
- 23:16would be based on the chart. They're you know, they're
- 23:18basically at or maybe a little bit growing faster than than
- 23:21Meta. Their revenues are probably
- 23:23right on top of Meta's now probably 200 billion this year
- 23:25versus 200 billion for Meta, but higher growth rate for Byte
- 23:28dance. I think the one adjustment you
- 23:30have to make now is with the spin off of TikTok that is no
- 23:33longer part of the business, although they own 20% of that
- 23:35U.S. business. So if I, if I pro forma them
- 23:38right back to take out the US business and just go with what,
- 23:42what they have in the rest of the world's and the attribution
- 23:45to the USI think they're right on top of Meta now.
- 23:48They've now revalued exactly what you'd expect them to based
- 23:50on comparables and based on, you know, a, a business that is 1/3
- 23:55the size of Meta in terms of evaluation, but has the same
- 23:58revenues as about half as profitable, maybe 2/3 as
- 24:01profitable, has exposure to the US still has that the benefits
- 24:04of the tech talk license agreement.
- 24:06So this one now feels like this is where I would have, you know,
- 24:08I would have expected this to be the the the valuation.
- 24:11Right, OK, I, I decidedly lower valuation tender is fintech
- 24:16company Plaid. Plaid revealed that it had
- 24:19completed a tender offer to employees at a valuation of 8
- 24:23billion. That's up from a $6 billion
- 24:25valuation back in April of 2025 when it did a previous tender
- 24:30offer, down from maybe the 13 billion in 2021 when they had
- 24:35previously been valued. And I guess they they had turned
- 24:39down an acquisition offer or something had been blocked.
- 24:42I I believe with Visa correct? So Visa maybe acquisition offer,
- 24:47I think that was the $5.3 billion acquisition regulators,
- 24:50you know, I'm sure had a bunch of conditions on how that would
- 24:53go forward. I think it's and Plaid and then,
- 24:55you know, then the business began to pick up in 2020 because
- 24:57the during the pandemic a lot of the Plaid benefited from the
- 25:01mobilization of commerce. So they've had a bit of a, you
- 25:04know, rocky road stance. So when since their evaluation
- 25:06got reset, they went as high as 13 billion in 2021, they got
- 25:11reset to six after the crash. So this is invested in 390
- 25:14million in revenue. So it's about a 20 times
- 25:17multiple based on the latest round.
- 25:18I think that's pretty good. Their growth rate in 2023 had
- 25:21really slowed down to low teens, 12% revenue growth back in 2023
- 25:27and then we accelerated to 27% more recently.
- 25:29So I think they did have a reset after the the bubble pops, but
- 25:34you know this is to that $6 billion number.
- 25:37But I think everyone got reset and and payments and this is now
- 25:40a much better reflection of where they are a 20 times sales
- 25:42multiple. I think for them is actually
- 25:43quite, quite a quite a big win. I think we'll end this week with
- 25:47one last story of the secondary market.
- 25:50Robin Hood launched a billion dollar pre IPO stock fund giving
- 25:55the retail market opportunity to sort of cash in on private
- 25:57companies. I guess you would say Kathy
- 26:00Woods arc fund does a little bit of this little known public
- 26:04company called Destiny XYZ, which has some SpaceX did this.
- 26:09I think we're seeing aqueous anime be forged offering similar
- 26:13things. So our retail markets coming to
- 26:16secondary Aman are we are we going to be out of business here
- 26:19as a secondary fund because the retail market jumps into these
- 26:22vehicles? I hope not, I guess is the
- 26:24answer. But between the machines coming
- 26:25on one side and my mom and retail coming on the other side,
- 26:28maybe maybe you know, the question is what's the play,
- 26:31What's the, what's the space you occupy?
- 26:34I guess think of it this way in, in public markets, you have
- 26:36institutional money and retail money, right?
- 26:39You've got pension funds and hedge funds and insurance
- 26:42companies making smart bets and taking significant ownership
- 26:45positions on allocation strategies.
- 26:47And that's what VCs ought to be doing.
- 26:49I think Robin Hood and I guess to some extent Kathy Wood are
- 26:52opening the playing field to retail money.
- 26:54We're just going to go after stocks, but without that
- 26:57institutional discipline or governance or oversight.
- 27:00And that's probably good for the market and hopefully good for a
- 27:02lot of investors. But I don't I don't think it
- 27:04displaces institutional capital. At least I hope not.
- 27:08Well, I hope you enjoy your hockey game and I'm off to New
- 27:11York next week. I'm going to go check out the
- 27:14East Coast and get a little snow and ice, I guess, while I'm
- 27:18there. Hope you have a great week and
- 27:22we'll see you back in the markets.
- 27:30All right, what's what's new with Stripe this week?
- 27:33And let's break down the valuation now.
- 27:35They're up substantially from, I guess, just a year ago, right?
- 27:39Yeah, just a year ago, they've been doing a tender offer every
- 27:42year, more or less February, March of every year for about 3
- 27:45years now. They've really systematized it
- 27:47and I think that a really good job of recruiting and pulling in
- 27:50new investors every step of the way.
- 27:52A year ago they were at 91.5 billion.
- 27:55They were rumored at the start of this year to be at 140
- 27:57billion, which would already make them the most valuable
- 28:00payments company in, in the world and probably, you know, 2
- 28:03times over versus anyone, anyone else.
- 28:07I think they were oversubscribed and they're now operating at
- 28:09$159 billion valuation. So very big step up from a year
- 28:14ago. Their last primary around they
- 28:16haven't even raised money as a primary company for three years
- 28:19now. The last prime around was three
- 28:20years ago at a $50 billion evaluation.
- 28:22So we'll talk a bit about their metrics and you know how we, how
- 28:25we see that shaping up. This is a company generating
- 28:27about 20 billion in top line revenue, total revenue.
- 28:31There's an important concept we're going to dial in on which
- 28:33is net revenue for any payments provider.
- 28:35We're just taking money in from merchants.
- 28:37You're paying a bunch of fees and processing costs.
- 28:39You should always look at the net of that.
- 28:41At PayPal where we worked, we would just call that the gross
- 28:44profits. The way that the way that Stripe
- 28:46shows it in their financials, they call it net revenue.
- 28:49I think that $5 billion net revenue number is really a much
- 28:52more important way to benchmark them versus any of the other
- 28:55payment companies. So, you know, just a pro tip for
- 28:58anyone investing in a payments company, just to recap now where
- 29:02they are in terms of their valuations.
- 29:03This chart shows in the green how much they've raised and then
- 29:07the blue line shows where the valuation was.
- 29:08So going back to 2000, 2020, one, they were pretty much
- 29:11raising every year, not a lot of money, but you know, enough to
- 29:14run the business. They then raised a fair amount
- 29:17in 2021, their business dramatically accelerated.
- 29:20They got a big increase in their secondary valuation and they
- 29:23didn't need to raise money. They turned the turn the corner
- 29:25profitability and didn't need to raise a lot of money had a bit
- 29:28of a reset in 2223 when the market tanked.
- 29:31They, like everyone else, got reduced by about they went from
- 29:34an A 95K an hour valuation to about 50.
- 29:37So almost got cut in half, raised a lot more money.
- 29:41That's the green. And then every year since
- 29:43they've had steady up for the right progress on resetting the
- 29:46valuation to the secondary market higher.
- 29:48So I think just a really good, you know, a plus performance and
- 29:51how to manage tender offers. One of the crazy things to think
- 29:54about in, in terms of the valuations is look at the
- 29:57multiples now on strike. They're at a 25 X multiple on
- 30:01net revenue. Take Audion, which is very
- 30:03familiar in terms of payment volume.
- 30:05Now they're Audion is only a $30 million valuation.
- 30:08There's seven times sales and then PayPal and Block are at
- 30:12basically one times sales. Kind of crazy to think about.
- 30:15How is it possible that you know, stripes it in such a
- 30:18premium to all these other companies and the team across?
- 30:22What's all that magic sauce about?
- 30:23Why is that such a big difference?
- 30:26Well, I think what it comes down to is let's talk about
- 30:29valuations and you know how you think about valuations.
- 30:31So on the Y axis I want to chart something called EBITDA margin
- 30:35multiplied by your growth rate, OK, So take your revenues and
- 30:39your multiplied by your profit margin that gives you your
- 30:42profits or EBITDA cash flows. That's really what payment
- 30:44processor should be tracking to and then look like that by the
- 30:48growth rate. It's a bit of a hack.
- 30:51It's a shorthand formula just to simplify some important concepts
- 30:54down to one metric, but it's basically growth and
- 30:57profitability. And any discounted cash flow
- 30:59analysis you do will focus on growth and profitability.
- 31:03Different ratings, they will matter differently in the
- 31:05valuation depending on the rate of growth, on the amount of
- 31:08profitability, the terminal value, quote UN quote.
- 31:11All that isn't in a textbook you can buy online, but just
- 31:14simplify it now to this one metric on the left hand side of
- 31:17the chart and then on the on the X side of the at the X axis.
- 31:20Now it's just going to be the EV to 25 sales.
- 31:23So what is your enterprise value divided by your sales?
- 31:25Well, let's start with tracking certain payment processors like
- 31:29we just talked about PayPal and block Fiserv Western Union.
- 31:33You can see where they fit on kind of a a line of best fit.
- 31:36Visa is way off to the right. Much higher growth, much higher
- 31:39multiple payment processors like MasterCard and Visa are going to
- 31:42be because of their the network effects they have and their
- 31:45established market position are getting premium multiples.
- 31:48But it kind of makes sense given premium growth.
- 31:50A couple of others want to add in ADP and paychecks.
- 31:53These are payroll processors. So they are payment processors,
- 31:55but they have some lock in effects because they're working
- 31:58with your payroll provider. Tough to switch away from those
- 32:00guys. So a little bit higher multiple,
- 32:03but also higher growth rate. Well, let's see now where Stripe
- 32:07and IDM fall and you can see where they land right on that
- 32:10line of best fit. So they they are getting a
- 32:13premium multiple, but it is a reflection of very, very rapid
- 32:15growth rates in their underlying business being able to
- 32:18demonstrate now profitability, extending profitability.
- 32:21And so you know, that kind of justifies the devaluation.
- 32:24So I think based on this new round, as long as it can keep
- 32:27delivering these kinds of numbers, it feels like Stripe
- 32:29was probably being fairly valued.
- 32:32One thing I do want to I'm kind of concerned about that.
- 32:34I'm now hearing rumors about Stripe buying PayPal or maybe
- 32:39acquiring their way into some other businesses, Right.
- 32:42Any time you're worth 159 billion, I think there's that
- 32:44temptation. PayPal in one time was worth 300
- 32:47billion in the pandemic. They're now down something like
- 32:5085% from that peak to only 45 billion.
- 32:53I know there are a lot of people at who are now thinking about
- 32:56PayPal being an acquisition target and strike as a natural
- 33:00acquirer for PayPal could be a big benefit if they do buy them.
- 33:04I can think of three advantages that that strike get right away.
- 33:071 is scale. PayPal has got a lot of
- 33:09customers and a lot of consumers.
- 33:10The second is the cost advantages.
- 33:12PayPal was able to process volume from their balances and
- 33:15bank accounts. That's all technology that Dave,
- 33:17you and I helped to build, right?
- 33:18And then consumer. Paypal's got consumers all over
- 33:21the world. The challenge of getting into an
- 33:23acquisition, though, where I do feel like Strike might get
- 33:26distracted. 1 is there's a lot of technical debt with PayPal.
- 33:32What do I mean by that? They were built 25 to almost 30
- 33:35years ago now. So Stripe is all APIs.
- 33:38It's very cutting edge technology.
- 33:40They're going to have to figure out how to either acquire,
- 33:43integrate or more probably deprecate probably billions of
- 33:46dollars of technical R&D that PayPal has invested in network
- 33:50that won't integrate with what Strike does.
- 33:52So that's one concern. And Stripe is never a lot of
- 33:54acquisition history, right? They've only made a couple of
- 33:56acquisitions in their history. The most recent one was like no
- 34:00more than a couple of billion dollars.
- 34:01So they don't have a lot of expertise in acquiring and
- 34:05integrating companies. The second concern is if they do
- 34:08go after someone like PayPal, I know that they will not think
- 34:12the last bitter capital bond will jump right in.
- 34:14Probably JP Morgan Chase will jump right in and start bidding
- 34:17up the asset. PayPal shareholders won't want
- 34:19to let it go aside for some huge, you know, without a huge
- 34:21premium to where the where the market is right now.
- 34:24We know from our past experience Google and Apple have designs on
- 34:27payments. Apple has a pretty good project,
- 34:29but left PayPal and then Meta and Amazon.
- 34:32I don't know that they've given up on their payment dreams.
- 34:34They've they've sunk 10s of billions now into payments with
- 34:38not much to show for it and they still want to be in the game.
- 34:40So I do kind of worry that Stripe might get distracted with
- 34:43their increased market cap in a acquisition war.
- 34:46It also complicates the IPO story if you start making
- 34:49appositions. But if you set aside
- 34:51acquisitions and potentially those opportunities, I think
- 34:53Strife is right where they're supposed to be given, you know,
- 34:55organic business profitability growth and have clearly
- 34:59established themselves now as the most successful payments
- 35:02leader with the best technology, probably a top five private
- 35:05company in in the world now based on its latest valuation.
- 35:08And I think the very likely IPO candidate if you want to do it
- 35:10and you know, 2020, six, 2027. So I'm kind of bullish on
- 35:14Strife. I think this is a good, you
- 35:15know, reflection of the progress they've made.
- 35:18Small anecdotal story, I I met Patrick Collision probably over
- 35:2110 years ago. He was then I guess one of the,
- 35:25you know, best companies that came out of YC and was kind of a
- 35:28darling at the time we had the opportunity to invest.
- 35:31In fact, Patrick asked us when we were running 500 to invest.
- 35:37And at the time, you know, I think Stripe was already a
- 35:40billion dollar company, 500 was mostly investing in early stage
- 35:44I think because we had exposure to a lot of international
- 35:47markets. That's why Patrick was
- 35:48interested. He actually spoke at a
- 35:50conference that we organized called Commerce ISM way back
- 35:55about e-commerce. We ended up putting a small
- 35:58amount of money into the company when they think they were only
- 36:01valued at between 1:00 to $2 billion.
- 36:03And that ended up being one of our best investments.
- 36:06That's actually why we have a position in Stripe also was we
- 36:09bought secondary in one of 500 funds that held that Stripe
- 36:12position. I, I wish I'd bet bigger on
- 36:16Stripe at the time, Patrick always seemed like a pretty
- 36:19amazing leader as well as his brother John Collision also.
- 36:23So one thing I think you maybe have overlooked there, you talk
- 36:28about that technical debt issue. I think that that's going to go
- 36:31away as an, as a problem because of AI.
- 36:34And I think we've already been hearing that there's now AI
- 36:37that's going to go in and recode a bunch of COBOL for IBM and all
- 36:40these old folks. So I think the technical debt
- 36:43issue is going to get solved by AI much quicker than maybe
- 36:47anybody realizes. Sort of seems like Stripe and
- 36:50and maybe Apple would be the more natural acquirers.
- 36:53I, I don't know about the other financial providers that you
- 36:56mentioned, but it does seem like something's going to happen
- 36:59there in the near future and that we do have a, a new set of
- 37:03kingmakers in the payments world.
- 37:06Yes, I feel like Paypal's on the block.
- 37:08I think you're right about Apple.
- 37:10And we know that you remember Google Pay.
- 37:13Maybe not because they they try that.
- 37:14Yeah, and then a bunch. Of people from PayPal, but it
- 37:18never really got off the ground now.
- 37:21Meta, we know friends that we know LTS and our fund and
- 37:25friends of the of the company who've run payments at Facebook
- 37:28and it just hasn't really gone anywhere.
- 37:30The only concern to have the technical that point is well
- 37:33made. The only concern to have is
- 37:34someone like Stripe because they don't have a history of
- 37:38acquiring they're builders. Yeah.
- 37:40And I think that's now where we were we were builders, eBay was
- 37:44an acquirer and it was just different skill sets, different
- 37:46DNA. We botched more acquisitions to
- 37:48be to be successfully integrated, but you know, having
- 37:52the discipline to walk away from a company that has has technical
- 37:55deck where you have to fix it, where you have to integrate it
- 37:57is that's an important, you know, trait of the collisions.
- 38:01I think where if they make the bets, they really know how to
- 38:03they have a good product plan on how to build it and integrate
- 38:05it. And if you, you don't get
- 38:06distracted by, you know, by some of these other companies that
- 38:09seemed good on paper, but just turned out to be culturally
- 38:11weird or, or hard to integrate. So I trust their judgement on
- 38:15it. I just think you, you could
- 38:15easily get into a bidding war with someone like PayPal, a very
- 38:18different culture. All the PayPal folks are ex
- 38:20investment bankers now and they come from heart associations and
- 38:24Stripe came from a a they'll come from a different cloth.
- 38:26And so I worry about things like cultural and integration, But I
- 38:30think the business is fantastic and would would also if they can
- 38:34fix a technical debt issue with PayPal, it could be a good
- 38:36synergy there. I think you're right to mention
- 38:39Facebook or Meta as a as a potential acquirer also, I think
- 38:42they are one of the few that could maybe handle and manage
- 38:45that. And there is a lot of PayPal DNA
- 38:47that went over to Facebook and Meta.
- 38:49So strikes strikes me that Apple, Apple or Stripe and
- 38:53possibly Facebook or Meta, Facebook and Meta would be the
- 38:57other acquires that would be natural fits.
- 38:59I guess we'll we'll see what happens.
- 39:02All right, I'm on. Well, thanks for the valuation
- 39:04corner and go USA. Yo, USA, thank you, Dave.
- 39:11See you next time. Mom, are you OK?
- 39:17Mom. Come with me if you want to
- 39:21live. All right, Well, thanks for
- 39:36joining us this morning. I'm Dave McClure, founder and
- 39:39Managing partner at Practical Venture Capital.
- 39:41And Daniel Blake, who's the founder and CEO of UI
- 39:44Charitable, is also with us. And we're gonna tell you guys
- 39:47how to save millions of dollars in taxes.
- 39:50And that's not just a crazy pitch.
- 39:53Personally, myself, I have booked more than $5,000,000
- 39:56worth of tax credits using this strategy in the past couple
- 39:58years and probably a little bit more in the next few years as
- 40:01well. So this is a real strategy and
- 40:04we'll give you actual case studies of people who have saved
- 40:07six and seven figures by using this method.
- 40:10Dan, could you give us a brief introduction to yourself and UI
- 40:13Charitable and then maybe we can talk a little bit about who
- 40:16we're talking to today and what we're going to try and explain?
- 40:18Yeah, absolutely. Like Dave mentioned, my name is
- 40:20Daniel Blake. I'm the CEO here at UI
- 40:23Charitable. UI Charitable, we, we really
- 40:26think of ourselves as a philanthropic back office for
- 40:29high net worth individuals and institutions.
- 40:32And so we focus on making sure that you're giving is structured
- 40:37in the most tax efficient way possible as well as making sure
- 40:41that you accomplish the charitable outcomes that that
- 40:43you care about. So like Dave mentioned, we're
- 40:46going to run through a couple of strategies that are very well
- 40:51documented strategies, but aren't very well known.
- 40:55So that the IRS has very clear rules on how these strategies
- 40:59work. And there's a tremendous amount
- 41:01of value being left on the table specifically for investors and
- 41:05founders. So we're we're just going to go
- 41:07ahead and jump right into it. So the the problem that we're
- 41:11looking at is for individuals that have privately held
- 41:16illiquid assets, these can be very difficult to sell.
- 41:21The value of the asset on paper is generally going to be very
- 41:25different than what you can actually sell it for.
- 41:28Currently we're seeing assets like these LP interests, you
- 41:32know, founders equity, if it's sold in a secondary transaction,
- 41:37it's often times sold at a very steep discount.
- 41:40And I could attest to that as your greedy buyer of secondary
- 41:44shares. We are tough negotiators and
- 41:47many cases the discounts that we're buying individual equity
- 41:50in companies is 30 to 50% for fund interest, GP and LP
- 41:54interest. Sometimes that could be as high
- 41:56as 50 to 70%. And so part of the strategy is
- 41:59really just to show you that by doing a tax, by doing a donation
- 42:03and tax reduction, depending on what state you live in and what
- 42:07tax rate you're paying at, often times you can save more money in
- 42:10taxes than you would get from trying to sell a tough interest
- 42:15on the secondary market. And so the thing that most
- 42:17people don't realize is just how easy it is to donate those
- 42:21privately held complex assets. By donating those assets, you
- 42:26get a, a tax deduction based off of the fair market value.
- 42:30You avoid capital gains when those assets are sold.
- 42:34And this is a fantastic way to increase the funding for your
- 42:37charitable goals. So, and that's a a great segue
- 42:41into this next section on donor advised funds.
- 42:44Dave just gave a a great explanation of donor advice
- 42:48funds. So a donor advice fund really is
- 42:52an alternative to a private Family Foundation.
- 42:55It's like having your own charitable investment account.
- 43:00You donate to your donor advice fund, you receive an immediate
- 43:04tax deduction. The assets in the donor advice
- 43:07fund can grow tax free and then you can give out of that donor
- 43:12advice fund overtime to any nonprofit or most social
- 43:17ventures. It is important to call out that
- 43:21a donor advice fund is a separate public charity.
- 43:25That's how you receive your tax deduction.
- 43:28And so you you are the donor advisor and the individual donor
- 43:33advice fund is going to have specific rules and guidelines
- 43:37that they follow. So it's really important to
- 43:38understand who is your donor advice fund host and do they
- 43:43have any additional restrictions above and beyond what the IRS
- 43:46allows? At UI Charitable, we really
- 43:49pride ourselves on giving donors all of the flexibility that's
- 43:52afforded to them by the the IRS. And the the power of a donor
- 43:57advice fund really is around the separating the timing of your
- 44:02tax deduction from the timing of your charitable giving.
- 44:05And by separating those two things, you're now able to
- 44:08optimize for both of those. I just wanted to point out
- 44:12something that Dan mentioned on that previous slide.
- 44:15Dan, if you could go back one second there.
- 44:16So you mentioned this is an alternative to setting up a
- 44:19Family Foundation. That's a really important point.
- 44:22And let me just tell you that setting up a Family Foundation
- 44:25is much more of a pain in the butt and a lot more challenging.
- 44:29There's a lot more reporting. I'm saying this because I've
- 44:32done both and I wish I had not set up the Family Foundation.
- 44:37I wish I just gone straight to set it up the DAF and it's a lot
- 44:40easier to manage a lot of this within DAF.
- 44:44Also for a personal Family Foundation usually doesn't make
- 44:47sense unless you have at least $1,000,000 or more to set up a
- 44:50Family Foundation. Dafs are much easier to set up
- 44:54on a much lower dollar a month. Dan, I don't know what the
- 44:56smallest DAF you've ever managed to set up, but I believe it
- 45:00could be less than, you know, $10,000 if people want it.
- 45:03We have Dafs that are as small as, you know, thousands of
- 45:06dollars. Yeah.
- 45:08And I think the other thing that to mention here is although the
- 45:12shareable grants are emphasized, you can still manage investments
- 45:16inside your DAF in any type of, you know, vehicle that you want.
- 45:21And we'll talk later about you could even transfer in crypto
- 45:25assets and hold and invest crypto assets.
- 45:28I've personally made startup investments and even fund
- 45:31investments out of my DAF. You can put those in normal
- 45:35public stocks or indexes. You could do any kind of
- 45:39transaction for most parts that you can do within a normal for
- 45:42profit vehicle. Just that this is happening
- 45:44within your your charitable entity.
- 45:48The only thing that I would add to that donor advice funds are
- 45:51essentially twice as tax efficient.
- 45:54The tax deduction that you receive depending on the asset
- 45:57can be upwards of twice as large compared to a private
- 46:00foundation. So not only is it easier to set
- 46:03up, easier to manage, but donor advice funds are generally far
- 46:08more tax efficient than a private foundation.
- 46:12Most people also don't realize how flexible donor advice funds
- 46:17can be and everything that you can donate into a donor advice
- 46:21fund. When most individuals that
- 46:24already have a donor advice fund, you know, they, they are
- 46:27contributing cash, they're donating public securities and
- 46:32you know, that's, that's fantastic, you should do that.
- 46:34But they don't realize that you can donate private company
- 46:37stock, GPLP interest, precious metals, cryptocurrency, real
- 46:41estate, essentially any asset that you can have appraised by a
- 46:45third party you can donate into a a donor advice fund.
- 46:49And so when individuals. Look to for one second and I
- 46:53would just say you're actually telling a little bit of a lie
- 46:56there. Not every donor advice fund can
- 46:58accept these and in fact, most donor advice funds will not
- 47:02accept private company stock, GPLP interest in the fund and
- 47:05cryptocurrency. So that's a particularly a
- 47:09special attribute of UI charitable.
- 47:12I guess I'm, you know, selling here because I am a customer as
- 47:15well, but you know, contributing private company stock and in
- 47:20particular holding it in the same form after you made the
- 47:23donation into your donor advice fund and sent the new GPLP
- 47:26interests and crypto is not typical for most donor advice
- 47:29fund. So although we can saying here
- 47:31that you can do this into a DAF, you should check which DAF
- 47:35platform or sponsor you're talking to you whether they
- 47:37allow that. Many of them do not.
- 47:40Many of them won't accept illiquid assets and many of them
- 47:43will force you to sell those liquid assets if they do accept
- 47:46them. So that's really a particularly
- 47:48important point that we're talking about here for UI
- 47:50Charitable is that they allow illiquid asset contributions
- 47:54like stock or fund interest or crypto, and they allow you to
- 47:57hold them in that same form after you've contributed them to
- 48:00your DAF. Yeah.
- 48:02No, that's a great call out there.
- 48:04There are hundreds and hundreds of individual donor advice fund
- 48:09platforms, donor advice fund sponsors, and they they all do
- 48:13have very different rules and additional constraints that
- 48:16they've placed on themselves. Again, at UI Charitable we think
- 48:19it's really important that if, if the IRS allows you to do it,
- 48:23you should be able to do it. And so again at UI Charitable we
- 48:28will allow you to donate essentially any type of asset
- 48:32that can be appraised by a third party.
- 48:34And that requirement of having the the asset be appraised by a
- 48:38third party is simply because that's the IRS requirement for
- 48:43non public securities. I need your clothes, your boots
- 48:51and your motorcycle. You forgot to say please.
- 49:04So what does this mean for founders and employees?
- 49:09Again, I think there's a tremendous opportunity here.
- 49:13So if you are a founder, if you're an employee of a high
- 49:17growth startup, you are going to be holding a tremendous amount
- 49:21of illiquid wealth and on occasion you are going to have
- 49:27very meaningful liquidity events and those liquidity events
- 49:30create a one time tax planning opportunity.
- 49:34If we go back to the the first example that I shared of you
- 49:38know the, the business selling for $10 million, that doesn't
- 49:41happen everyday. That's a large transaction.
- 49:44You have to get the timing right if you want the tax savings.
- 49:48So if shares are donated in kind prior to a sale, you receive a
- 49:54tax deduction in the year of the donation and that's based off of
- 49:58the fair market value of the asset.
- 50:00And then you also avoid capital gains on the shares that were
- 50:05donated into your donor advised funds once.
- 50:09I should mention in, in a special case, Dan, that might
- 50:12not just be capital gains, that might be ordinary income.
- 50:15And for many people in the Bay Area who are going through
- 50:18secondary sales tender offers or selling those shares themselves,
- 50:22especially if they have to exercise their shares and sell
- 50:25them in a short period of time, you're going to have a very
- 50:28large tax bill to pay. And sometimes people aren't
- 50:32aware that that, you know, they'll be paying it.
- 50:34The maximum, you know, ordinary income rate, which might be
- 50:383940% of the federal level, could be 1010% or more if you're
- 50:42living in California, New York or Massachusetts.
- 50:45So sometimes half of your gains will end up going to taxes if
- 50:50you're not doing tax planning carefully.
- 50:51But you could probably cut that by half, at least at the federal
- 50:54level, if you do plan ahead. The the opportunity is massive,
- 50:59but the timing is so, so important.
- 51:02I mean, if, if you miss the the window around timing, if you
- 51:07don't do this in kind and you, you sell your ownership, you've
- 51:11booked the ordinary income capital gains that's
- 51:14irreversible, you now owe taxes. So the order of operations here
- 51:18really matters. So, and again, it's a super
- 51:23simple process, donate the the non public shares in kind to
- 51:27your donor advice fund. It maybe takes you two or three
- 51:30minutes to set up a donor advice fund.
- 51:33We will help you craft the the legal documents to transfer the
- 51:38assets into your donor advice fund.
- 51:40We'll walk you through the process there.
- 51:44Once those assets are in your donor advice fund, you can
- 51:47either hold them like they've mentioned or you can sell them.
- 51:50If you do sell them, the assets are sold tax free and then you
- 51:54have cash available to support the charitable causes that that
- 51:59you care about. So again, most people just don't
- 52:01appreciate how simple this process can be to donate non
- 52:05public shares in kind prior to a liquidation event.
- 52:12So that's founders and employees.
- 52:14There's also a tremendous opportunity for investors.
- 52:19You know, this is if you are AGP or an LP.
- 52:22This is also true if you have a direct investment in a company.
- 52:27So when donated, the IRS determines the value of your tax
- 52:32deduction based off of the fair market value, which is going to
- 52:35be determined by a third party appraisal.
- 52:39That is often times very different than what you can
- 52:42actually sell the asset for. So, you know, and Dave, do you
- 52:47want to talk about kind of the the.
- 52:49Discounts, you're being pretty subtle here Daniel, but the
- 52:52scenario is you could offer you get that fair market value
- 52:55appraisal at a much higher number than the market will buy
- 52:58that asset for from you. And in some cases there really
- 53:02may not be a buyer at all for the asset.
- 53:05Again, I can speak from personal experience here, you know, not
- 53:09to mention any particular companies or funds.
- 53:11Many of us might be holding investments in overvalued
- 53:15companies, busted unicorns from you know, four or five years ago
- 53:19where the on paper value might be a billion dollars of the
- 53:23actual value of that company might be a lot less than that.
- 53:27In fact, I would say again, you, you might have a price for a
- 53:31company that's half that on paper value or less for fund
- 53:35interests. It could be 1/3 of the on paper
- 53:39value, it could even be 0 because there are there are no
- 53:41buyers. So something we often say in
- 53:44JASP, it's really true, the IRS is always a secondary buyer of
- 53:48last resorts. And what we mean by that is you
- 53:52can get a third party appraisal and often times that will be at
- 53:55the on paper value as reported by the company and their most
- 53:58recent financials or by the fund manager in their last quarterly
- 54:01report. You would go to a third party to
- 54:04get that appraisal. That's a fairly quick process
- 54:07and usually done within 30 days, sometimes even faster.
- 54:11And if you've ever watched the 1800 Cars for Kids commercial or
- 54:15if you've ever donated clothes to Goodwill, often times those
- 54:19folks will give you a receipt for your donation.
- 54:23That's a very optimistic value for your car or your clothes.
- 54:27That's not any different from what we're talking about here.
- 54:30I'm not asking anyone to miss reports or to try to play games
- 54:34with the IRS. But as long as you get a third
- 54:36party fair market value assessment, they will probably
- 54:40use that last reported public funding round or privately
- 54:44reported quarterly financial statements as their initial
- 54:47place to start beginning their homework.
- 54:49And sometimes you can get it for 100% of that value on paper.
- 54:53That might be a lot more than you would get in trying to sell
- 54:57it on the public market and certainly for fund interest.
- 54:59That's that's true. Dan, I think you probably have
- 55:02some math on the next slide that explains that.
- 55:05Yeah. I I just want to hit on this
- 55:06point one last time. For the tax deduction, the
- 55:10assets are valued at the fair market value that is locked in
- 55:14when you make your donation. So whatever happens after that
- 55:19is independent of the the value of the the tax deduction.
- 55:23So that asset may rise or fall in pretty significant ways after
- 55:29you've made that donation. If it increases in value, you
- 55:33don't get an additional tax deduction.
- 55:35Again, the tax deduction was locked in based off of the third
- 55:39party appraisal in the fair market value.
- 55:41If the value decreases for whatever reason, again, it
- 55:44doesn't change the the value of that that tax deduction.
- 55:48So this is a very simplistic model.
- 55:53So two options. You have a GPLP interest.
- 55:58On paper it's worth $1,000,000. You can go get that appraised
- 56:03and donate that to your donor advice fund.
- 56:06You're going to receive $1,000,000 tax deduction based
- 56:09off of that fair market value. If you sell it inside the DAF,
- 56:14you avoid capital gains. It's another 20% savings versus
- 56:18selling that in a secondary secondary transaction, you might
- 56:22be selling that for $0.50 on the dollar, $0.30 on the dollar.
- 56:26If you sell that, you know your $1,000,000 LP position.
- 56:30There might not be a buyer, there might not be a buyer, and
- 56:33the value you could get is essentially 0.
- 56:36Yep, absolutely. So, you know, maybe here we're
- 56:39being optimistic. You sell it for $300,000, you
- 56:42know it's a 3X increase and in many cases it's going to be
- 56:48significantly larger than than that.
- 56:51So again, this is there are hundreds of thousands of dollars
- 56:56that's all employees, all founders, all GPS, all LP's are
- 57:01leaving on on the table by not understanding this, this
- 57:05strategy. Broke my arm.
- 57:11There are 215 bones in the human body.
- 57:14That's one. Well, maybe just talk
- 57:16personally. Again, from my experience, there
- 57:18are probably 2 scenarios, 1 where you have some assets that
- 57:21you think are probably optimistically valued or you
- 57:24know, maybe going to go lower in value in the future.
- 57:27You can have certainty by donating those assets into your
- 57:30donor advised fund and locking in that tax deduction at the,
- 57:34you know, most optimistic value that you can get from a, from a
- 57:39third party fair market value assessment.
- 57:42It might go up, it might go down.
- 57:44If it goes down, you've locked in your, your tax deduction
- 57:47savings at the point of donation.
- 57:49If it goes up, worst case scenario is you have more money
- 57:51in your philanthropic pocket to give for charitable causes or to
- 57:55invest, which isn't the worst thing.
- 57:57So again, I want to make the, the station here, you're not
- 58:00necessarily giving this to someone else at that point of
- 58:03donation. You're giving it to your own
- 58:05donor advised fund. It's still under your direction
- 58:08to some extent and control. It's not your personal money,
- 58:11but it is part of your philanthropic accounts and you
- 58:14can still hold that asset if you think it's going to appreciate,
- 58:16You don't have to sell that right away.
- 58:19So you might optimize for, you know that potential upside
- 58:21within your DAV. Absolutely.
- 58:25A couple of details just worth calling out.
- 58:28The deductions of a illiquid private asset are capped at 30%
- 58:33of your adjusted gross income. If the deduction value exceeds
- 58:38that 30%, the excess tax deduction can be rolled forward
- 58:42for up to another five years. And so, again, just a lot of
- 58:46flexibility here when it comes to tax planning.
- 58:49The things that you do want to consider, regardless of, you
- 58:53know, if you are a founder employee, GPLP, this only works
- 58:59in this particular case if you have AUS tax exposure.
- 59:03There are things similar to Dafts in other countries, but if
- 59:08you don't have any U.S. tax exposure, this isn't going to be
- 59:11a strategy that you should be pursuing.
- 59:14And then you also need to make sure that you can get the GP or
- 59:17management consent to actually transfer your ownership interest
- 59:21into the donor Advice fund. I have gone through hundreds and
- 59:25hundreds of these transactions and I can maybe think of a
- 59:30single transaction where we couldn't get the GPU or
- 59:34management consent to to make the transfer.
- 59:38The the process again is much simpler than people realize.
- 59:43You select the asset, we will then help you do due diligence
- 59:48on that asset. The due diligence really is
- 59:50around the consents needed to do to make the transfer.
- 59:55We will then help. We will then craft a gift
- 59:58agreement that takes into account any of the consents that
- 1:00:03you need to make the transfer. You then execute that gift
- 1:00:08agreement. You need a third party appraisal
- 1:00:11to determine the fair market value of that tax deduction.
- 1:00:16When you file your taxes, you're going to file what's called a
- 1:00:19Form 8283. You sign it, the appraiser signs
- 1:00:24it and your donor advice fund is going to sign it.
- 1:00:29And that's, that's really the entirety of of this process.
- 1:00:34It is, again, like I mentioned, just much simpler than most
- 1:00:37people realize. Dave, you've done this now,
- 1:00:39what, half a dozen different times?
- 1:00:41At least our generally say it takes between two to four weeks.
- 1:00:44Most of the time is really getting the appraisal scheduled
- 1:00:48and lined up with the with the party to do it.
- 1:00:50For more complex assets, it might take a little bit more
- 1:00:53time. So a fund interest might take a
- 1:00:55little bit more due diligence and appraisal than a single
- 1:00:58asset. If it's a single asset with the
- 1:01:00company and you have a recent, you know company financial or
- 1:01:04quarterly statement, it's probably fairly straightforward
- 1:01:07to do that that process. And again, yes, I've done this
- 1:01:11personally at least three or four times.
- 1:01:13We've done it with some of our clients multiple times as well.
- 1:01:17And this this is. Going.
- 1:01:18Down. One thing I wanted to go back to
- 1:01:20on the previous slide, just for calculation purposes, Dan, you
- 1:01:24mentioned 30% of your adjusted gross income rolled over five
- 1:01:28years. So the basic calculation you
- 1:01:29should probably make is how much money you're going to make in
- 1:01:32the next 5 years, both in terms of ordinary income and
- 1:01:35investment income. Add those numbers up for five
- 1:01:39years multiplied by 30%, and then go find an amount of assets
- 1:01:43equivalent to that amount that you can donate so you can
- 1:01:47maximize and and hopefully not pay any taxes for the next 5
- 1:01:50years, at least at the federal level.
- 1:01:53Well, that's, that's great. Thank you, Dave.
- 1:01:55We've talked a lot about investors, founders, you know, a
- 1:02:00private business interests, GPLP interests.
- 1:02:02I also want to call out just cryptocurrency.
- 1:02:06This is another asset that you can donate to a donor advice
- 1:02:09fund. Again, you should donate it in
- 1:02:12kind. There are many donor advice
- 1:02:15funds that will accept cryptocurrency.
- 1:02:20The vast majority require you to immediately liquidate that
- 1:02:24cryptocurrency. We're different and we in the
- 1:02:28fact that we allow you to hold whatever token, whatever token
- 1:02:34it is that you have. And then we are also very unique
- 1:02:38in that we are currently the only donor advice fund that will
- 1:02:41allow you to grant it out in kind as well.
- 1:02:46And so you are able to stay on chain for the entirety of the
- 1:02:50life of your donor advised fund. Far more flexibility here than
- 1:02:54many people realize. I think this is important for
- 1:02:56folks who might have been early in crypto and are sitting on top
- 1:03:00of a really large taxable event. If they ever sell it where they
- 1:03:04could donate a portion of that not have any gains and and all
- 1:03:08of a sudden you know, then they could sell it within their donor
- 1:03:10advised fund for cash or hold it, but they can start doing a
- 1:03:14lot of other investing or charitable getting with those
- 1:03:18proceeds. Absolutely.
- 1:03:21Again, process is very simple. Go through, identify what token
- 1:03:25it is you want to donate. You move that into your donor
- 1:03:28advice fund. You receive an immediate tax
- 1:03:30deduction. You can then decide, do you want
- 1:03:33to continue to hold in kind? Do you want to liquidate and
- 1:03:36diversify or do you want to donate that to, you know,
- 1:03:40whoever your preferred charitable causes, they've
- 1:03:44mentioned this at the very beginning.
- 1:03:46Not all donor advice funds are created equal.
- 1:03:49We, we pride ourselves again on giving donors all the
- 1:03:54flexibility that's afforded to them by the IRS.
- 1:03:57So we will accept far more complex assets than the typical
- 1:04:03donor advice fund. We will allow you to continue to
- 1:04:07hold those complex assets where appropriate.
- 1:04:10If you'd like to sell them, you can.
- 1:04:13Once those assets are in the the donor advice fund, Dave alluded
- 1:04:18to this, but there's a tremendous amount of flexibility
- 1:04:20in how you invest those assets. If you want to invest in public
- 1:04:25securities, that's fantastic. If you want to continue to
- 1:04:30invest in Private Securities, you can.
- 1:04:33We have a couple. We have one really interesting
- 1:04:35case study where a a donor donated their employee equity
- 1:04:44and then invested it in kind into another fund.
- 1:04:47So just a tremendous amount of flexibility in how you manage
- 1:04:50those assets and then again, a lot of flexibility and the
- 1:04:54charitable causes that that you support.
- 1:05:02I'll be back. Let's look at two different case
- 1:05:09studies. So this one was a former
- 1:05:13executive they should say at a major social media company.
- 1:05:17This was pre IPO. So this, this executive was
- 1:05:21looking at his holdings and decided he wanted to sell some
- 1:05:27portion prior to the the IPO as as they were going through that
- 1:05:33transaction, they were doing their tax planning and decided
- 1:05:36in addition to selling their shares, they should also set up
- 1:05:41a donor advice fund to reduce the overall tax burden.
- 1:05:45So they donated $5,000,000 worth of their employee stock into
- 1:05:49their donor advice fund. They then went through a
- 1:05:55secondary transaction. They sold, you know, a large
- 1:05:59portion of what they owned personally in addition to
- 1:06:02everything that they had donated into the donor advice fund given
- 1:06:08kind of the quality of the asset.
- 1:06:10This was sold at a 0% discount, which I candidly I think is
- 1:06:14pretty rare. And so they had $5,000,000 cash
- 1:06:20go back into the donor advice fund.
- 1:06:22And so the individual received a $5,000,000 tax deduction when
- 1:06:27they made the donation and then avoided capital gains on the
- 1:06:31full $5 million that was sold within the the donor advice
- 1:06:36fund. They now have $5,000,000 cash
- 1:06:39that they can grant out to whatever charitable activity
- 1:06:42that they would like. The benefit of a donor advice
- 1:06:46fund is there are no annual requirements around how much you
- 1:06:54have to give. So if you want to give
- 1:06:56everything away in one year, you can.
- 1:06:57If you want to give nothing away in a year, that's also OK.
- 1:07:01So just a tremendous amount of flexibility there.
- 1:07:04And this second one, a founder of a $800 million tech company.
- 1:07:10This company had raised, you know, 100 plus $1,000,000 in
- 1:07:14capital. Founder donated $1,000,000 worth
- 1:07:17of shares in kind to their deaf. They received a the $1,000,000
- 1:07:22tax deduction for that donation. And then the thing that I think
- 1:07:26is really creative here is they took those shares and invested
- 1:07:30them in kind into a fund so that they could have greater
- 1:07:34diversification. In this particular instance, it
- 1:07:38was invested at a 20% discount. Given that all that was done in
- 1:07:42the structure of a donor advised fund, that was all a tax free
- 1:07:45transaction. Assuming this fund does really
- 1:07:48well, it's going to return more than $1,000,000 into the Donor
- 1:07:52Advice fund, which again will appreciate in value.
- 1:07:55All tax free. I think one of the other things
- 1:07:58to note here, I'm I'm pretty sure I'm familiar with both of
- 1:08:01these two examples, although they're anonymous.
- 1:08:03I, I think I was the referrer about these folks to you.
- 1:08:06I in, in the first case, not only was that, you know, cash
- 1:08:12within the fund given to chair was also used to make individual
- 1:08:16startup investments. And I've done that myself as
- 1:08:19well, both startup investments and my funds and funds.
- 1:08:23And in the second case, I'm pretty sure that was invested in
- 1:08:27our fund. But one of the things I would
- 1:08:28point out was whether you invest in our fund or another one, you
- 1:08:32can still get diversification benefits as well.
- 1:08:34So one of the things that is typically the case that
- 1:08:37someone's donating a single company position is it's a
- 1:08:41highly concentrated asset. And so just like they might want
- 1:08:45to get diversification benefits in their for profit pocket in
- 1:08:48your donor advice line, you might also want to diversify
- 1:08:50that position. So you might sell to get cash,
- 1:08:53but you also might, you know, transfer it into a fund in a
- 1:08:56more diversified portfolio and you know, hopefully get some
- 1:09:00benefits from the other portfolio positions there as
- 1:09:03well. But I think it's really unique
- 1:09:05specifically with UI that you can manage and hold these assets
- 1:09:10in the original form. You can transfer them into other
- 1:09:13fund interests. You could do other, you know,
- 1:09:16crypto investments or deployment.
- 1:09:19You could even do startup and VC fund investments within your
- 1:09:23donor advice fund. And again, personally I've done
- 1:09:25more than $3,000,000 worth of investments in startups and
- 1:09:29funds and even fund to funds within my donor advised fund.
- 1:09:32One of the things that I will mention that's a an example that
- 1:09:36I talked to someone recently about is many people hold their
- 1:09:39options unexercised and if they are leaving a company then they
- 1:09:44have a limited time frame to exercise those options.
- 1:09:46So cards correct, they might need to, they might need cash to
- 1:09:50do that exercise otherwise they would lose those shares.
- 1:09:54If they want to have a lower tax rates on the shares, they might
- 1:10:00exercise and hold in order to then get capital gains treatment
- 1:10:04if they hold for more than 12 months instead of ordinary
- 1:10:07income treatment. So if you if you exercise and
- 1:10:10sell your shares right away, you're probably not going to
- 1:10:12qualify for capital gains. And that would typically be at a
- 1:10:15very high tax rate, sometimes the maximum tax rate at the
- 1:10:18federal level as well. Well, we are happy to answer any
- 1:10:22other questions that that people have otherwise, like Dave
- 1:10:26mentioned, you know, also happy to jump on individual calls with
- 1:10:30people if you have specific scenarios that you'd like us to
- 1:10:34walk through and explore with you.
- 1:10:45Well, once again, been kind of a slow Newsweek.
- 1:10:48Hardly anything has happened here in Silicon Valley or in the
- 1:10:50rest of the world. I just don't know if we're going
- 1:10:53to have enough news items to cover every week.
- 1:10:55Come on. I'm sure we'll come up with
- 1:10:58something, Dave.