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VENTURE CAPITAL & PRIVATE INVESTING
Recorded: Aug. 14, 2025 Duration: 1:02:21Space Recording
Short Summary
In a dynamic discussion on the Venture Capital Show, industry leaders explored the booming IPO market, the convergence of private and public investment strategies, and the rise of digital asset treasury companies. With significant fundraising efforts underway and innovative projects in the pipeline, the conversation underscored the vibrant growth and evolving trends within the crypto and venture capital landscape.
Full Transcription
Thank you. Thank you. yo good afternoon wolf crew welcome back to the vc show what's up, Kyle? What up, what up, what up? I'm hanging around in the background,
but I'm excited to listen in.
I know I've listened into one of these in the past
because I'm usually busy,
but I got another chance tonight.
So I'll be hanging around with y'all.
Awesome.
Yeah, no problem.
We've got a fantastic show to go over here.
And as we start to onboard everybody,
if you want to drop a post
or retweet what's going on here so that we can maximize the coverage, that would be awesome.
I'm going to do the same. And while we do that, it is a really exciting time to talk venture capital
and private investing. This really has been pretty cool, Jared. I see you're up here with me.
We have really seen the whole market flow through this 2025 year. From when we started,
we really hadn't seen any company's IPO yet. We hadn't seen this cycle really kick off. Bitcoin
had done well, but was still kind of trending upward. And now we're into August. We've seen
a booming IPO market for some of these tech stocks, all time highs across the board on the
markets, but not to mention crypto is ripping at least Bitcoin, Ethereum. And I think many people
are hoping and looking forward in anticipation for that to trickle into the broader venture ecosystem.
So I think there's a lot of things moving right now. We also have seen the AI space blow up,
and we've seen cycles around defense tech and things like that that have been trending in
different directions. So it's just been a really, really interesting year, and what a fantastic one
to be able to document here on the Venture Capital Show. We do this show every 5 p.m. EST on Thursdays. We took a week off last week, but this week
we are back and better than ever. So before we dive into everything, my name is Kyle Sondland.
I describe myself as a capitalist, if we're being honest. I'm a second generation family
office. We do a lot of investing. I'm a GP on a few different funds.
I've raised capital for my own businesses across my career, as well as syndicated capital,
meaning I bring other people together with me alongside into particular deals.
So I've done a whole host of different things with some interesting new things that I may
have coming down the pipeline that I can't wait to talk about in the coming weeks or months.
But with that, I want to kick it over to my co-host, Jared.
Jared, what's going on with your world?
Hey, hey, glad to be back.
It's a good day.
Glad to get into some topics here.
Definitely excited about it.
Thanks, everybody, for joining us. My name is Jared, and my connection to the VC space is I help founders grow their brands on X.
We've helped anywhere from companies that are pre-seed, pre-revenue,
all the way up to publicly traded companies and helped them grow their brands.
We've done over 3 million followers, billion and a half impressions for them.
And so the idea behind that is when you
have a bigger audience, you can market to more people and make more money. And so that's kind
of my connection, kind of how I got tied into this VC space. And I definitely am excited to
dive into the conversation today. I know we have Andy. Andy, I don't know if you're on stage yet,
and we have another speaker joining us as well. So if they're up there, then feel welcome to hop in.
But otherwise, Kyle, I'm definitely excited to hear about your exciting news that you mentioned.
Yeah, a lot of things going on right now.
And, you know, I've really spent a lot of my time paying attention to some of these digital asset treasury companies, which is continuing to just blend these trends. I mean, we've talked on the show quite a few times
about how the private and public markets continue to converge. And I think that we've seen how the
crypto market building venture-based companies that have liquid publicly traded instruments earlier and earlier
in their cycle has really caused significant ripple effects. And I think I could probably
talk about this for 30 minutes. So Jared, feel free to cut me off if I ever ramble too much.
But I just think it's fascinating how crypto has impacted a lot of investors by shortening the duration of a timeline that a lot of earlier stage investors are expecting returns on their businesses.
And I had some great conversations today. Actually, I'm in New York City for the week.
And I'm talking about the implications of that with a few family office managers that I've been able to speak with this week and the impact that
that's made on the market. And now we're seeing public vehicles that are investing in either
private assets or alternative assets and the implications of that through a lot of these
digital asset treasuries, which are also raising money from venture capital funds, who now venture
capital funds are investing in public market vehicles. And so we're really seeing just a fascinating trend and switch of all of these different things.
And I'm not sure what the future of this looks like, but it now seems like venture capital,
private equity, and hedge funds are all kind of doing the same thing.
And so I think that there's a lot of conversations that can be had around that.
That's really what I've been paying a lot of conversations that can be had around that.
That's really what I've been paying a lot of attention to recently, Jared.
I definitely think that's exciting. I definitely, that was one of the conversations I wanted to talk about. Friend of the show, Matthew, who's been on quite a few times, his fund is doing that Michael Saylor strategy, Tom Lee strategy, but with XRP.
And so he's a huge XRP bull.
So it's interesting to see how they're allocating funds and how more companies are continuing to move treasury there.
It's definitely interesting.
And I'm a huge proponent of it. I want to ask you, are there other assets as companies start to do this and maybe start to, they see the benefits, their balance sheet goes up significantly and they didn't have to sell any more products just because the asset they were holding instead of cash went up.
just because the asset they were holding instead of cash went up.
Are they going to start once more and more companies start to see this?
Is this going to expand further out into other asset classes to become more mainstream?
I know some companies do already, but I would love to get your take on that, Kyle.
And then, Andy, I do want to pass it to you if you have any insights you want to add in here
and if you want to give yourself a quick intro.
Andy, if you want to intro first and ensure any thoughts, feel free before I go on a little
diatribe here.
Yeah, listen, first of all, thank you for the invite.
I always feel like I'm the first grader in the high school class every time I come in
in the high school class every time I come in here.
here.
I love helping.
I love helping.
My experience is for 35 years,
I've done project management, program management,
organizational change.
Every time there's a big investment
and the projects go sideways
and they're like someone's gonna get fired,
a VP's gonna get fired,
the chairman's gonna end up in the newspapers.
They usually hire me or my firm to come in and help save the projects and move things over. So
I'm not on the front end, even though I've done a lot of procurements and a lot of that piece,
I'm on that backend when, when, you know, when the rubber hits the road, when, when they try to
merge the companies and it, uh, you know, the vision doesn't necessarily match the reality.
So that's, that's where, where my experience comes in. I've done lots of that all over the
world, billions of dollars worth of projects. And most of them have been, you know, impacting 40
million users, like an entire country, like the entire state of California, like half the U S
like, you know, the, the whole country of Egypt or the whole country of Turkey.
Crazy, crazy big implementations like that.
So I'm on that. I'm on the interesting side of the front end of the vision of where that PE and VC money comes from.
And then they hire me to come in and help them fix it and make it work.
So that's what I bring. And I love being in this room.
I'm very grateful, but I also feel like a first grader most of the time. So I'm here to help.
You guys have any questions, feel free to ask me. And I've done a couple of hundred hours and a
couple of hundred episodes of AI and business and how all that works. So I'm happy to help
share as much as I can. I love your perspective and Andy, and I mean this in the most respectful way.
No question's a bad question here. I think that sometimes I can get a little carried away, but it
is why I try to be verbose in my perspective, because I hope that by providing the context
and kind of uber explaining without using too much jargon, while it isn't necessarily the quickest explanation, hopefully it makes it an easier one to comprehend for the listeners.
And so part of part of this conversation today, not only do I really love to to hear your expertise on some of these topics, whether they're crypto related or if we just go into general markets commentary in the private markets. Would love to hear your expertise.
But on the other side, if you have a question on something,
I guarantee you that there are probably people in the audience that also have similar questions.
So I'd love for you to be that kind of voice of the people
and feel free to ping or follow up or double click on things that either don't make sense
or do you have questions around or even if I'm wrong or Jared's wrong
and you have contradictions or ideas that that's what makes for a good
conversation. So really appreciate you being here. Yeah. I love, I'm happy to carry the torch
of asking the stupid questions. I'm not, I am not offended, right? I'm totally okay with saying,
what the hell are you talking about? So, all right. I'll, I'll try to do that. I won't disrupt
the conversation though, but I appreciate it. No. No problem at all. Feel free to either jump in whenever or put your hand up and we'll make sure.
But yeah, to take that conversation a step further, Jared, around the digital asset treasury angle, I do think it's interesting.
Part of the problem with crypto, and I think that this may be refreshing to hear for some people in the audience, is that it doesn't actually own anything, right, as we've talked about.
And you can justify the value proposition like a Bitcoin or an Ethereum. I think there's probably a decentralized coder network and a decentralized compute of actual computers that are running
these softwares that are validating and verifying the math behind the system. And there is value
that is, I think, hard to necessarily hold with your hand, but it is valuable within a computer
network when you're building software.
There is value there for individuals and for companies that can be maybe quantified more effectively.
The problem is that that I think is heavily skewed towards the largest tokens and the
most used tokens within a blockchain ecosystem. I struggle to validate the same, I would say, underlying value for, let's call it the 50th or 100th most valuable token in the, you know, if you went to coinmarketcap.com or whatever to look up these tokens.
And I think the same probably applies for the 10th largest token.
And I think the same probably applies for the 10th largest token.
It's probably pretty elastic as you go down that top chart from number one down to even
number five or number 10.
It's probably significantly less as a weaker network effect and a value proposition from
my perspective.
And I think a lot of people may agree or disagree with that.
But the reason I'm bringing that up is actually more to go back to the digital asset treasury
argument.
And so I've been advising a few of these companies and just watching these markets a lot.
And there's kind of two approaches to a digital asset treasury company from my perspective.
One approach is the kind of the all in, all chips on the table. We could call it the you only live once, the YOLO strategy, which is the argument that,
hey, I think that fiat currencies like the U.S. dollar or the euro or the Japanese yen,
the Chinese renminbi, I think that the global world order of today, the fiat system is broken and we are not going to be able to stop this inflation train that keeps coming down the tracks.
I think that the U.S. is going to have to keep inflating.
And because they set monetary policy for everybody else, everybody else is going to have to keep inflating.
And so therefore, I don't think that crypto is going to go down ever.
Therefore, I don't think that crypto is going to go down ever.
And so if you have that mindset, which I don't for the record, but if you did, you would
just buy as much of these assets as possible, assuming that from a correlation perspective,
it almost doesn't matter which token you own.
They're all going to be worth more than the fiat currency that backs them.
worth more than the fiat currency that backs them. And so in that type of future, in that path,
Jared, your question, I think, is a reality, which is you're going to see digital asset
treasury companies for every token going down the line. And if you're going to have some for
Bitcoin, you're going to have some for Ethereum, you're going to have some for Solana, you're
going to have some for Ripple, you're going to have some for the next guy and the next guy and
the next guy and the next guy. the next guy and the next guy.
The problem for me is that I don't think that that's the future.
A, I think that our global economic system is probably here to stay for a little bit longer than what some of the bears might point to.
And despite the fact that it may cause increases in Bitcoin or Ethereum or some of these other
ones, I don't think that that's necessarily going to trickle to the entire equation. So therefore, there is a second path for digital asset treasuries,
but I'm going to pause there because I see your hands up. So before I go into the second side of
the equation and the one I think is more sustainable, let's talk through that first
bit a little bit. Jared, I see your hand is up. Yeah, I have one follow- up that I want to ask on that. I do want to get to a separate topic here with Andy. But one question on the Treasury side here is, as stable coins become more and more of a thing, Scott Bessens talked about it.
You can say what you want about somebody like Tom Lee or Michael Saylor.
They're doing what they're doing essentially to, in some ways, as chairman, they're kind
of legally shilling their stock.
You could make that argument.
Somebody like Scott Bessent talking about stable coins, he doesn't necessarily have
the same upside, I would say, of shilling like that.
So there's probably a little bit more believability
to it, if you want to say. And so as stable coins continue to become more and more of a thing,
and nation states and everybody starts using them, does that force more and more public and
private companies to adopt ETH or whatever blockchain that the stable coins are on,
but let's just say ETH because that's going to be more than 50% of them.
Does that force these companies to start holding ETH?
Not necessarily because they want to do the whole Tom Lee strategy,
but more so because they need the stable coins to,
one, secure the network. And because they're transacting so much with stable coins that they
then by default have to use the layer one. It's a really interesting question. I think
potentially on the surface, the answer might be yes. and I think that your mind is going the right way. The question is that we saw just this week two pretty significant blockchain announcements
came out in this topic line, and they were both doing something similar.
And that was that Circle and Stripe, Circle being the second largest stable coin, as you
mentioned, which is a dollar pegged crypto.
It trades a dollar all the time.
Circle is the second largest, largest U.S.-based company that does this.
They've got tens of billions of dollars of stable coins outstanding.
Them and a company called Stripe, which many of you have probably surely heard of,
which is one of the largest payment processors in the world, one of the largest private companies in the world.
Both of these companies individually and separately announced they were launching their own blockchains.
And so presumably that is going to rival Ethereum with respect to payments, both of which I would expect are going to be using
stablecoins. Obviously, Circle will because they already have their own. And Stripe will either
use some of these stablecoins from existing sources. But if Circle is launching a competitive
product on their own blockchain, presumably Stripe is not going to get the approval,
but maybe they will. So either way, it does provide an interesting question of,
okay, are those blockchains going to take the same strategy of ETH where you need to pay for
gas fees, using the native currency and all of these things, which may end up having ripple
effects, as you mentioned, Jared. because if you can use Stripe's blockchain
and use Stripe's stablecoin that has the same impact from a virtual economy perspective
as an Ethereum-based stablecoin, but I don't have to take exposure on ETH as a crypto,
I don't need to pay the gas fees in ETH as a crypto, I don't need to pay gas fees at all,
or if I do, they're paid in transaction fees on dollars or whatever it is that could present an interesting change in my
projection, just based off of which blockchain is the one that a lot of these merchants choose to
use. I think that the question that you're asking is definitely the one that Ethereum wants you to answer with yes.
Yes, if you are going to use a stablecoin on Ethereum,
then you should want to have exposure to the underlying blockchain of Ethereum
by owning the Ethereum cryptocurrency.
But I'm not so sure that that's going to be the case over the long term.
So that's kind of my short answer is it certainly depends on which chain you use.
And some of the newer blockchains that have been announced may kind of turn this model
on its head because of the fact that they may choose to go in a different direction
than what we've seen from the existing solutions from Ethereum and some of the other ones of
the legacy system.
Well, I was throwing some thumbs down there because when I hear the word stripe right
now, it's a trigger word for me.
I got debanked from stripe here recently and I was like, come on, man.
What's going on?
So I'm bearish on stripe right now just on the aspect of not personally happy with them.
But it'll definitely be interesting to see how all that plays out.
I know we could talk the Treasury stuff all day long.
I'm super interested in this.
It's been something I've been looking at a lot here recently.
But I do want to kind of shift topics here and bring Andy in on this.
Andy, I know you've done a ton of work
with different companies, like you mentioned earlier, and you mentioned user acquisition
on large scale models. I'm very curious to hear what you've seen just in your experience of what makes products stick as far as acquiring users and where do people go wrong when having trouble acquiring users for their companies.
Because one thing I see a lot, and not even just with clients, but just talking to a lot of people and listening to a lot of people reading a lot of things is people struggle with client acquisition.
You know, they might have a good product or they might have a really bad product, but
one, it doesn't really matter if nobody knows what it is.
But then once you get them to download, how do you get them to go from a free user to
a paid user and to get them to stick so your churn, so you have low churn?
So Andy, I'd love to get your take on
this from somebody who's seen that at a large scale. Okay, so you're going to laugh. You know
what the most important thing is to retain customers? Captive market. So if you're the
only one that provides a Medi-Cal system for the California Medi-Cal application, guess what?
20 million users.
There you go.
If you're the only one who's providing cell service in the Eurasia area between Turkey and Greece, your app's going to win. If you're the only one, it's like the Nokomo, I forget it, the Japanese cell phone company.
They're the ones that, captive market is how you get those big giant things.
And those are the kind of activities that I've worked on.
But to answer your question directly, the most important thing is, what are you solving?
Are you solving their problems, right? Think of a crazy thing like just the cell phone technology.
Cell phones came out and they were in doctor's cars and they were in a Mercedes in the handheld
piece. And then they became a big block, and then they became smaller,
and they became smaller, and smaller, and smaller, and then they became more functional,
more functional, more functional. And today, homeless people get their food stamps using
a cell phone and an app. Because it's cheaper. I mean, the technology that we have available to us is so pervasive and so inexpensive relative to everything else that $100 a month for a cell phone to get unlimited service and unlimited phones and unlimited data is achievable by almost anybody.
by almost anybody. And so that giant scale is why we have huge levels, a huge group of Android phone
users and a huge group of iPhone phone users and not much else. So those things are there.
As far as acquiring users, the best way is to find an audience and, you know, just the whole VC thing.
Find a company that has a good product and a good thing, roll it up into something else.
Acquire that company, acquire their customer, acquire their IP, and then use that to integrate
and apply more and more and more.
And that was the Microsoft model.
IBM did that too, but Microsoft really, back in the day, made that
everything. Every single tool you have on Microsoft was an add-on that they purchased from somebody
else. Hardly any of it was homegrown developed. It was brought in, integrated, and then pushed
stuff out to all of their users. And the utility and functionality is where you win.
I mean, it's the same valuation
if you're looking at a company
as if you're looking at a user base.
If there's only one user and it's 90% of the business
and the user goes away, the business goes away.
So the same criteria you use for acquisitions
is the same criteria you use that somebody else uses
to figure out how to retain customers and
how to do that. It's a challenge no matter which way you do it. Hope that answered the question.
No, that's definitely some good insight. And obviously the monopoly aspect is
anytime you can create a monopoly, you know, like Apple and Samsung have done,
like Apple and Samsung have done, you're going to win.
And obviously, that's a huge place to, huge reason why that makes sense.
But what about the markets that are maybe more competitive or maybe you're trying to
make something just a little bit better?
Like, how do you get started?
Obviously, once you get going and you have something that nobody else has and that everybody
needs, it's easy to sell.
But I feel like a lot of times startup founders are just trying to take something that already exists
and make it just a little bit better.
How do they go about making it a little bit better
and getting people to believe that it is a little bit better to acquire those people over?
One place I see it a lot is with a lot of different investing startups
or finance startups. There's a million different places and ways and strategies you can invest.
So why should we work with you with this tool? Or why should we work with you on your app? What
makes your app different from the next one? There's a million different ways to budget and to invest, to plan out your finances. What
are different things that separate categories that are fairly niche-based already?
Okay, so you asked like three questions. The last question, what's the most unique thing and
how do we do that? The only truly unique thing that I've seen in the last 20 years is AI.
Everything else is a rehash or a rebrand of some functionality or some utility that we currently had.
You know, phones have been out for years, whatever.
But AI, just literally 34, 35 months ago, was when it became pretty much publicly available and adopted.
And now there's 700 million people using ChatGPT.
So it's crazy.
But I think to answer your other question, which was, if you're a founder and you have
some new thing or some whatever, I'm not an expert in the marketing side, but what I see
is that ideas are easy.
Shark Tank is on every night and they have a hundred ideas, but that doesn't mean they're
any business at all.
Business is different than the idea.
I kind of feel, maybe it's just me, but I kind of feel like a good businessman can take
an average idea with an average company and make it into a powerhouse.
And somebody who has no idea about business could have the golden goose and still screw it up.
I think that's a really good, really good line right there.
And I think there's a lot of importance behind that as well.
No doubt about it. Another question that I want to pose here for both of you, Kyle, maybe your perspective as an investor side.
And so I guess I'll pose that first is one thing I've seen a lot. We talk about the separation
of companies. One thing that I feel like separates a lot of the different companies that I talk to
and that I've seen a few different times with just talking to different people is how people allocate capital.
I think a lot of times founders, they get, you know, maybe they're pre-revenue, maybe
they have revenue, but, you know, they get a big round, they get a bunch of millions
of dollars to basically deploy however they see fit. And
maybe how they spend that is not super thought about maybe in depth just because they have a
bunch of money and they say, yeah, what the heck? What's another 20 grand here or there kind of
thing? Or, oh, that's only a hundred grand. I could probably get it for 50, but I like this. Let's just go for it. And we see that a little bit with Cluelly, and I'm not
saying that's wrong, but those guys, I think a lot of it's satire, but they talk about spending
a million dollars here, a million dollars. They're paying people to set other employees up on dates
and stuff like that, where traditionally you'd be like,
that doesn't make any sense. But as far as for, so to get to the question, Kyle,
when companies start to get money as an investor, how much does it matter to you
how they're allocating that capital and what that looks like. So I'll pose that from the VC side for you, Kyle, and then Andy.
When you're going in and helping businesses, how much of that
is making sure that they're allocating capital correctly?
And do you see anything where
places where CEOs and founders have definitely mismanaged
money? What does that look like?
It's a fascinating question.
You know, it's really tough right now, despite the fact that, you know, there's a blend in kind of these private market investment verticals in a way that I think it was previously segmented when I'm talking about venture capital, which traditionally was private equity investing in the earliest stages of businesses. Often they
were not profitable businesses. Often it was structured as equity investments as opposed to
debt-based investments, which eventually at its furthest points was actually even pre-revenue at
all in the earliest phases of investing in venture capital. Then you've got private equity,
which was much more about giving existing businesses, even if they were in tech or
whatever, but revenue producing businesses, giving them additional capital to scale
a proven business model. Or that could be extrapolated into the latest phases, which might even be acquisitions of
existing businesses and either rolling up a set of businesses in the same vertical,
or it could be doing some sort of other play in terms of taking the company public or changing
the course or direction of the company by reducing costs and then selling off to a
different conglomerate firm in the same vertical. And then also the hedge fund style of business,
which typically or traditionally was very much a public markets only investment structure where
you were taking a lot of risk, but you were only really using stocks and public
market investments in your strategies, but just using aggressive setups, using options and
derivatives products and maybe taking aggressive bets on risky companies, but they were all public.
Whereas now these things have blended together in a lot of ways such that I think in the earliest stage of business, to answer your question, Jared, as a VC, it seems like much of the discussion now is much more I have this perspective, it's one that I've seen
over the last couple of years now, is that almost all of venture is now just about, well, who else
are you going to be able to get in on this round? Even in companies that are comfortable potentially
leading a funding round, that still does not have the same conviction that I think it would have had to be a follow-on check
from previous iterations, previous generations, previous vintages of startup funding. It seems
like in this current meta, it is all about lining up multiple funding rounds at the same time. Hey,
we're doing our pre-seed now, but we're also going to be raising our seed at this valuation in the future and potentially having your IPO plans set up for down the line.
I mean, even if some stuff is crazy, it's like Perplexity, who's a late stage startup at this
point, makes a bid for a part of Google's business in terms of Google Chrome at a 1.5
times valuation of their entire company, right? Like we're seeing this kind of early stage,
you know, capital market stuff just completely changing from what it was before, which was,
hey, I need $500,000 to build an MVP for my company. I think I can make revenue from this.
That's no longer something that's very attractive for a lot of these venture firms because of the attractive returns of, you know, I think you see a lot of funding style structure where you're investing in this company,
but you're not actually buying 13 and a half million in stock.
You're buying 13 and a half million of exposure into their yield generation strategies,
knowing that you're likely going to take that principle back out or keep that principle
to deploy into other things in the future.
And so it's a really weird time in venture.
And I could certainly maybe burn the crops down by calling out the conviction of early stage
venture capital fund managers in this process. But I'm not maybe going to go that far today,
or at least unless you guys really push me for it. But I definitely think
that's the biggest component right now for early stage venture is they're really trying to make
sure that you're not going to be insolvent. And so figuring out as a founder, how you can convey
a narrative that you have plans to raise additional capital and scale this business over time,
especially in the earliest phases,
is now absolutely something that's expected. And I guess that makes sense to some degree because
of a lot of the AI slop that's coming out. One thing that AI still has not been able to do is
build a lot of those relationships. So, so much of venture capital fundraising these days is
networking, much more than it is making pretty decks and making pretty deal rooms
and even building MVPs on Figma or things like that. Right now, the meta is traveling to where
the money is, building relationships with those individuals and getting them all to kind of
coordinate together into your business and figuring out how you are going to be the winner
in your particular vertical. Because the one other side that's tough for a VC right now is
that these portfolios have become so big that a lot of VCs are hesitant to invest in companies
that may be competitive to businesses within their existing portfolio. So if you're going to
an A16Z, they may have four investments in your vertical.
And so even if you think that you have a better solution, they're very heavily incentivized against participating in that deal solely because it may take market share from deals
that they've already invested in.
They've already written up that equity and they're already expecting that to return for
their portfolio.
So I think being very mindful of where you sit in the vertical stack, such that you can
get a lot of participation from a lot of these different investors and individuals is really
a lot of the game right now.
So funny enough, it has kind of become political in a lot of ways, which I think a lot of founders
aren't typically used to and aren't typically prepared to do in this space.
And again, not necessarily saying that's a good thing,
but really just commenting on the state of the market right now.
Awesome. Definitely appreciate those takes. Andy, I saw your mic come off. I'll let you go ahead. The way I, the, the, where they bring me in is after they've, after they've made the decision to do the acquisition, uh, and then they put together whatever package they do and they bring in some software or some consulting team or whatever.
Uh, that's when they, that's when they bring in me and my company. And they basically say, work on behalf of us.
Make sure they don't screw it up.
Make sure that they fix everything.
Tell us what's going wrong.
And the reason that they do that is all risk mitigation.
It's all basically like Warren Buffett's number one rule. Yeah, don't lose money.
It's the number one rule.
So if a smaller company is expending money
to buy a larger company or the other way around,
when they try to merge those two cultures together,
there's always, always problems.
And they only hire people like me
when things are challenging.
If it's smooth sailing, they don't need help like that.
They can get anybody.
They can do whatever.
But if you're fighting between Deloitte's doing this and Accenture's doing that, and then you're trying to merge these two companies and combine all of these, you know, software products and user bases.
And that's where it gets just absolutely sideways.
And the reason is because it's political.
Nobody wants to go to the board and say, you screwed up when you acquired these two things. Somebody sold you a bill of goods where you thought it was a really good idea or the CEO thought it was a good idea to acquire
this other something here and you thought it was a bolt-on and it's not. And so it is political.
And it's ironic that as the portfolios grow, the politics and the risk profiles and the risk
mitigation get higher. And they get higher to a
point because they don't want to screw up when they bring things together because, you know,
that's a career limiting move. Not only is it career limiting because that whole thing's going
to fall apart, that whole set of expectations is going to fall apart, all the promises that you
made is going to fall apart, but you're probably going to get fired and then you're out. And, uh, you know, the whole world you guys live in and the whole
stuff that we help support and build. Yeah. It's, you don't get a lot of chances, right?
You do a lot of really good deals. Everybody loves you. You do a bad deal. Hmm. You know,
not so much. And I've seen that happen too, where, you know, meetings with the board, meetings with
the president, that sounds something like this.
I know we're doing X.
Make sure we don't end up in the papers.
Okay.
So been there, done that.
Been there, done that.
It's not always fun.
It's not always fun.
A follow-up I'd like to ask, I guess, for both of you is you talk about second chances and opportunities.
A lot of times in anything, you kind of have one shot to make something happen, whether it's a time window, whether it's an introduction window, whether it's a business window with the way the market's set up,
whatever it is, sometimes you've got one shot to make it happen.
So what have you guys seen as far as that second opportunity
or what is your likelihood to do a second deal with somebody
or make a second introduction for a founder or something like that if the first time it doesn't quite go as planned for whatever reason?
Interesting question.
I definitely think that the whatever reason part is doing a lot of heavy lifting there.
I definitely think that the whatever reason part is doing a lot of heavy lifting there.
To be honest with you, I think it really does matter what the reason was that something didn't happen.
I do say to people that if you can get one deal done with someone or with a firm, then you're probably going to be able to get a thousand deals done.
Just because so much of the the difficulty is
just kind of working through logistically how things happen and it
is amazing that once once people start making money together once you can build
a business vertical out of something once you can start allocating budgets
towards things how much smoother the process can be doesn't necessarily mean
that there aren't other issues with scale, but I think that everybody becomes consciously more directed and dedicated towards trying to
solve those problems because the light at the end of the tunnel is there. You know that, hey, look,
if we solve these problems, we know that we're going to be able to succeed here because we've
done it in the past. And you can kind of point back to those things. So on the flip side of that,
back to those things. So on the flip side of that, I do think it is interesting. And I certainly
have, you know, when I make intros from somebody to someone else, I often can vouch for someone's
character. But I have said on multiple occasions, look, this is a really good person. And I think
that they're a killer. But, which is the classic word, I haven't gotten a deal done with that before, right? And I think
that that is a relevant piece of information for any particular connection you might have,
is it's like, look, if we haven't gotten a deal done together, then, you know, you have to discount
a little bit of what everybody brings to the table, because, you know, it's only true if you've really been
put to the test. And I don't necessarily want to say that that makes me discount somebody because
I'm sure that there's plenty of people in my network that would describe me the same way.
I work on a lot of deals and the close rate is not 100%. You might work on 100 deals and might
only close three. And I work in venture. So if you close three deals, it's worth the time of
putting in 100 deals because of the fact that return is going to be significant. So I think that it's not
necessarily as much as a knockdown on somebody that you haven't gotten something close with,
and more about building up that the people that I do close deals with the people that that have
been successful alongside me in raising capital, in closing big deals for revenue, in scaling
opportunities or syndicating deals. Those are individuals that I try to keep really close.
And I generally will have a lot more commitment to even when things aren't working well,
because as I mentioned, you have that point of reference to say, yeah, look, well, I do know
this person, they've got it when the pressure's yeah, look, well, I do know this person,
they've got it when the pressure's on. And so therefore I want to back them further when
things aren't going great. I think that it's easier to move on to something else or someone
else or a different firm when you haven't actually had something closed successfully.
So that's generally the way that I look at it. I mean, trust is obviously a huge one for me. So if
I can't trust you or can't rely on you, that's a much bigger knock on you as an individual than if just, hey, the market didn't turn out or we weren't able to bring people together.
But we all put in the effort.
We all gave it our best shot.
But there were some extraneous circumstances that happened.
I don't feel like I can judge someone for that in particular.
In fact, you may be able to build that bond stronger because you know you're both in the trenches together.
So there's definitely an it depends style of answer.
But I certainly think that the answer is more about how much more valuable it is to have relationships with which you've closed deals.
because I think it gives everybody more faith that it can happen again in the future.
Because I think it gives everybody more faith that it can happen again in the future.
I was alongside a project.
I was on a project where a big international company
was trying to do individual credit card transactions in China a couple decades ago.
And I was working on the delivery fulfillment side of it
and my partner and another lady from, well, she was from KL from Kuala Lumpur. And those two,
they worked out the deal between, I forget which Chinese bank it was, and this big company, the big corporation we're working with,
to allow for credit card transactions.
And the only reason, the single reason it went through
was because it was the big company,
and so the Chinese bank believed that the big company,
no matter what, would cover whatever the costs were.
That's the only reason it went through. It was because the power behind that big giant company.
But the amount of effort and time it took to build that trust was immense. I mean,
I mean, you know, two heavy hitting consultants with big payrolls and big teams working for months to get meetings so that they could say, we want to do this thing.
And then it worked and it was successful and all the transactions went through and everything was paid.
Open the door for those
kind of transactions to happen. And today, now we have Stripe and we have all kinds of things that
we can, those payment processors are there. But back then, we built that by hand, right?
So, and it was all 100% trust based on the people who were building all of the relationships.
So there was no second chance in that.
If you screwed that one up, we would have been hammered from both sides.
So as far as executives, so just half the time when people hire me and my company to do these kind of jobs and roles and provide this kind of support for projects, I know half the time they're just setting me up in case it goes bad that I'm going to be the one that gets the hammer.
And my company's going to yell that and they're going to say, oh, it was his fault.
It was the consultant's fault.
Half the time you're brought in on these kind of deals,
half the time, if you succeed, you're a hero.
And if you don't, you are there to save somebody's career.
That's just the way it is.
And that's okay.
You get paid handsomely for it.
So to follow up on that, Andy,
you're saving somebody else's career. We talk about the whole reputation thing and how does that impact your business?
If you're basically signing up knowing that half the time you're going to be the fall
guy even when it's not your fault, how does that impact your business? Every single person whose career has been
saved by any of the work that I've done is the very best reference you could
ever get for me. Think about that. I came in, I created a shield, I put barriers
and buffers in place, I saved their career. Every single one of those people
gave me the most glowing awesome review you could possibly imagine. Not even Andy could make it work.
He came in with his team. We did all these amazing things. And you know what? It just
didn't work out. But that guy, he's a solid guy. It's all how you position it.
Well, I would say that that makes sense.
No doubt about it.
We got about 10 minutes here.
And so if you're in the audience and you're new to the show, we host this venture capital private equity space every Thursday, 5 p.m. Eastern.
We talk about a range of topics.
Sometimes we talk about more current event stuff.
And sometimes, like this week, we just kind of let the conversation flow based on where the conversation's going.
And so I thank you for being here.
And if you ever have any questions, feel free to drop them in the comments, send us a DM,
or if you have people you recommend to be a speaker, we'd love to hear from them as well.
One question I want to ask as we got about 10 minutes left here, I just want to ask both of you guys, what is something that you're working on now, whether it's a company you're talking to
or an industry that you're doing a lot of research in, what is something right now that
you're really excited about in the space or that you're working on?
Something really interesting that I'm working on. Um, well, first off, I want to give Andy the
chance to, to, to answer this. If you have anything that, that you wanted to talk about
that you're working on. I'll do. Actually, I, I have, um, I've recently secured a couple of overseas VC firms that have given me some commitments to deals they're looking for.
I found some commercial property that they're kind of starting to get interested in.
But I also have put together a plan to build a board and create a very low-level fintech basically all
around bookkeeping. And you'd be surprised. Yes, you won't be surprised about it. But
the more problems people have, the more they're willing to get them solved, right? And one of the
main problems right now is financial education. but everybody in the world's teaching financial education. But this plan that we're putting together is actually going to fix some things or allow for a small subscription cost to have all of that managed and supported so that at the end of the year, they don't just get slammed by taxes and all the other compliance issues that you have for both small businesses and individuals. So I've got a team of people
working on that and secured a bunch of funding from some other VCs. So exciting.
Well, that's pretty exciting. And for a guy who says he doesn't do a lot of work with VCs,
that sounds pretty VC to me. That's definitely cool. You mentioned
everybody's teaching financial education and I agree with that. I work with a lot
of people in this space. Wolf Financial, they work with a lot of people in
this space. We understand that. The one thing
I think that is really interesting that I don't hear as many people talk about
is the taxes side.
And I'm a big believer that schools should be teaching basic financial literacy.
You know, they don't have to be teaching people, you know, how a blockchain works.
Actually, they probably should, but they don't need to be teaching people how to stake, you know, ETH or how to be using, you know, different DEXs or anything like that.
or how to be using different DEXs or anything like that.
But some basic things like taxes, how taxes work,
how self-employed taxes work,
and what's the difference between an LLC and an S-Corp.
I think all that's really important.
I'll be honest, I'm going through and doing my taxes right now.
I got an extension and I need to get working on that.
To be honest, just because I was maybe
one, procrastinating it, and two, maybe a little scared of what I might have to pay.
You mentioned the real estate side. That's probably next for me here this year, later this
year, start diving into that. I'm not as scared as my tax from my taxes. So that's definitely interesting.
One thing that I want to share a good highlight in the VC space for me is I recently made an
introduction to a from a founder to another founder. But the second founder also has his
own VC fund. And that one introduction brought a $500,000 investment. Just setting
up a group chat and say, hey guys, you're both cool guys pretty much. And that was pretty
cool to just as simple as setting up a group chat and got the founder I know $500,000 for his company.
So that's one of those deals where you get somebody $500,000 when they're looking for capital just like that with one introduction.
You know, you're in good terms with them for quite a while.
So that was pretty cool to be able to do that.
So that's one win I would share.
Kyle, do you have any you want to share?
Yeah, I think we actually helped one of the founders we had on our show one time with some investor introductions. I think it was a really cool opportunity here on the VC show, bringing on investors, hearing their perspectives and seeing that all the way through the life cycle. So I can relate to a lot of the things
that you're describing there
in bringing these things together.
And I guess the question back to you, Jared,
is when you made that introduction,
have you put any thought
or were you able to think about
how you personally would get compensated
for those types of things?
Or was it more of just doing a friend a favor
and he's going to buy you dinner for life?
Well, actually, he did end up paying me.
I didn't ask for it, but he said, hey, I want to make it right.
Maybe that's not always the smartest thing to do,
but I do kind of like that aspect of you just help somebody just to help them
and know it'll come back to you and know that they'll be solid
to you. And so he did end up paying me for that, I guess, as a bonus. But actually, both of those
founders are actually clients of mine. So it's pretty cool that I have clients who are in
different sectors and they kind of have complementary needs,
I guess you could say, or services.
And one guy was looking to invest money in a certain type of company and the other client
was that company.
And so that introduction helped.
And so for me, a big part of that was let me make myself more valuable to my client and this is what
he wants, not something I necessarily advertise as a service that I sell, but that's what
he needs.
I can help him there.
Part of my goal is too is if I can help them get more money and be more friendly to them, then that covers the cost of my service for quite a long time where I can continue to get paid on renewals of contracts and stuff like that.
So I didn't necessarily have black and white terms as far as that introduction other than just wanting to help them out and knowing that at some point it would come back to me.
And it came back pretty quick.
That's awesome. I love that.
And talk about a value add for some of your clients
to be able to help them with fundraising.
That certainly, I think to your point,
makes them a much more likely client of yours for the foreseeable future.
So that's awesome, man.
Yeah, I appreciate it.
It was definitely cool to be able to do it.
And also, you know, kind of stepping maybe a little bit into a different role in the VC world
and just gaining a little bit new experience and to get a learn a little bit more about how those conversations work.
Obviously, you know, you can you can hear about them one thing, but then to actually be involved in conversations like that.
Oh, sorry.
Hey, I lost you.
You there, Jared?
Or was it my connection?
I lost him, too.
Sounds like you had a phone call.
Oh, yeah, that always happens.
Jared, you there?
All right. Well, maybe not. So I think that, you know, we got one minute left
here. So I want to give Andy one last kind of opportunity. If you have anybody in the audience,
you know, we've got a bunch of people in here, over a hundred people are listening right now,
let alone we have, you know, close to a thousand at the very least people that tune in on, on the listens throughout either throughout this hour or in retroactively
listening, who are you looking for? How, how can,
how can the crowd be helpful for you? What's the main focus for you?
Well, right now I'm looking to, to just build more of an audience.
So I really appreciate the fact that you guys even gave me the mic to come up
here and speak. I appreciate it. I'm here to help. I'm here to share whatever crazy stories
I have from the past and apply them to the crazy new world we have today, whether it's AI or
politics or banks or whatever I've worked in the past. So I just appreciate the fact that you guys
are here. I'm honored to be invited and I'm happy to come any other time you need me. Thanks again.
Awesome stuff. So it's six o'clock. So I'm going to close this out here with, you know,
thanks everybody for listening and tuning in this week to another awesome episode of the
Venture Capital Private Markets X Spaces. As I mentioned, we do this every Thursday at 5 p.m. Eastern time.
So you can tune in and talk. So anybody in your network that is in the venture capital space that
you feel like would be a good fit for the panel, definitely reach out, whether that's to Wolf,
whether that's to me, whether that's to Jared, or comment in the thread below, or any questions,
topic ideas, anything like that, we'd be happy to run any of those things through the conversation.
This has been an awesome experience, and I'm really happy to be here.
So, Jared, if we have you, feel free to close out the show
and hand it off to Emp or to the Wolf account.
Otherwise, we'll just let them take it from here and close it on out.
Absolutely.
Sorry, everybody.
I got technical difficulties got kicked there,
but love the conversation today. Andy, appreciate you joining us.
Kyle, always a pleasure. Jordan, I'll kick it to you and let you finish it off.
A great space, guys. I always love listening into these.
I don't get to very often, but it's always a great conversation.
I love listening to you guys go back and forth and love the thoughts on taxes towards the ends there, too.
Jared, I think that's
a super important thing to talk about and something we all don't talk about enough,
especially in the trading industry as well. I would love to have more conversations about that.
So really good stuff. If you're in the audience, make sure you follow this amazing panel. We do
this conversation every week. So we'll see you guys next week, but we're going to close it out
for now. Everybody have a great night. We'll be back on the Wolf Trading Link bright and early in the morning
for some more live trading to close out the week. So stay tuned with that. We'll be live at 915
Eastern and yeah, we'll close out the week and get onto a great weekend.
Everybody enjoy the night. We'll see you bright and early. Thank you.
