What to Do When Most of Your Net Worth Is in a Private Company

April 28, 2026

In this episode of EWA’s FIN-LYT Podcast, Matt Blocki, Jamison Smith, and Weston Conway break down what it really looks like when 80 to 95 percent of your net worth is locked up in a single private company. Weston, a long-time EWA client and COO of Closing Lock, shares his firsthand experience taking an 80 percent pay cut to join a two-person startup that has since grown to 100 employees, raised $50 million in venture funding, and services a significant portion of the U.S. real estate market.

The conversation covers the emotional and financial weight of being “rich on paper” with no way to access that wealth until a future liquidity event. Weston explains how the Jeff Bezos regret minimization framework shaped his biggest career decisions, why he took chips off the table when the opportunity came, and how he resisted lifestyle inflation even after a secondary sale. Matt and Jamison dig into the practical planning side, from exercising stock options and 83B elections to trust and estate strategies for younger founders and operators sitting on fast-growing equity.

For anyone evaluating a startup opportunity, the team walks through how to think like an investor when picking a company to join, including how to assess customer acquisition cost, net dollar retention, and product roadmap. They also explore when it makes sense for a private business owner to bring in outside capital and what to watch out for when venture or private equity investors enter the picture.

Whether you are a founder, early employee, or business owner with most of your wealth tied to a single illiquid asset, this episode offers a real-world roadmap for making smarter financial decisions at every stage. Be sure to like and subscribe for weekly conversations that help you align your wealth with the life you want to live.

Managing Director, Wealth Strategy

Episode Transcript

Speaker 1 – 00:00
If you could have a million dollars today or flip a coin for $10 million, which one would you do? Most people you
would ask that would say, no, I’ll take that million, because how terrible would you feel if you.
Speaker 2 – 00:10
Flipped it and lost Whatever that number is probably will help you make better decisions because you’re not so
stressed on the outcome of the business.
Speaker 3 – 00:17
You took that 80% pay cut that came with a potential, not a guaranteed upside. What made you ultimately make
the decision?
Speaker 1 – 00:25
A couple people have given me advice, but it really all falls into that Jeff Bezos regret minimization framework.
Speaker 3 – 00:30
What are the biggest concerns that you see or ramifications of having a financial plan?
Speaker 2 – 00:35
The biggest thing is you’re rich on paper and you’re kind of building a plan where it could be anywhere from 80 to
95% of your net worth is tied up in this. And even if the business is successful, you may not get any liquidity out of
it.
Speaker 3 – 00:46
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Some of the best founders and also operators are those that are already financially secure because they can do
what’s in the best interest of the company. For someone considering to join a startup company, what advice would
you give to.
Speaker 1 – 00:57
Them in terms of like just the basics of understanding a business? You know, there’s really a couple key factors.
Speaker 3 – 01:03
Foreign welcome everyone. Super excited for this episode. We’ve got a long term friend and client, Weston
Conway. Welcome Weston. Excited to share the conversation? Yeah, so the reason we have Weston’s been through
several iterations of a lot of clients that have a substantial amount of wealth that’s tied into a private company or
private stock. And so with that there’s a lot of ramifications. A financial plan that, you know, someone has 50% or
more of their net worth on the balance sheet on something that literally cannot be sold until some event happens
in the future can be exciting. It can be a game changer. Can also come with a lot of financial, emotional,
psychological decisions. So we’re going to talk through all of those.
Speaker 3 – 01:54
But if we can start, we also have Jameson who many of our listeners are very familiar with Jameson’s on most
episodes of our podcast here. But Jameson, you’ve recently had a lot of experience working with people with
private stock as well. So I know you’re going to bring a lot to this conversation. But I guess to start off, Weston, can
you share your background as you know, going back to the Dropbox days and then more traditional route and then
how we ended up in the not necessarily a startup because you guys have had tremendous growth on the closing
Lock today.
Speaker 1 – 02:27
Of course, of course. And thanks again for having me on. Matt and Jamison. So I’m originally from the Midwest,
I’m an Ohio guy. So I went to school in Ohio, but love technology and knew I wanted to be part of the kind of Silicon
Valley boom. So after I graduated school in 2011, moved out to the Bay Area to get into the tech ecosystem and
spent a little bit of time investment banking there and was always mesmerized by startups. I thought the kind of
opportunity to learn and grow at a company like that is fun. So happened to kind of luckily networked my way into
a company called Dropbox which was really big back in the 2000 and tens with kind of file storage in the cloud. So
was one of their first sales hires in 2014.
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Speaker 1 – 03:07
And that’s when I really started to understand kind of startups and equity and fundraising and company valuations
and how all that works. So was there for about five years. Kind of really grew my career and learned a lot. Also got
some awesome opportunity to earn equity in that business and solid ipo. So that was my first experience with a
liquidity event is seeing the Dropbox ipo which was a lot of fun and it went into a company called Procore, which is
construction software. Really cool business. Spent a couple years there, also was able to earn some equity and
then also they IPO’d as well. So really got the bug there of kind of growing companies, exiting companies,
understanding what drives value within a business and then what. What came to me was a really unique
opportunity. So closing Lock.
Speaker 1 – 03:54
My good friend Andy, who I’ve known for 10 plus years here in Austin, had founded the company, it was just him.
Had a really cool idea for the business and needed someone to help kind of grow the sales side. So he was giving,
he was asking me advice on hey, what do I look for in a sales leader? What are some of the early things I should be
paying attention to as I try to grow this? And I was just really intrigued by the opportunity and I said I think I can do
this. So. So ended up joining Andy. So left my position at Procore. My last day at Procore was literally the day they
went public. I went in, had a glass of champagne and handed him my laptop. Took a 80% pay cut to join Closing
Lock.
Speaker 1 – 04:34
Not even making enough money to pay my month to month bills, but just saw a lot of opportunity in it and thought
it was the right time to take the risk. So did that five years ago from my perspective.
Speaker 3 – 04:43
I remember getting the email like, hey, guys, can we talk? I’m thinking about taking this and the salary would be X.
And I’m. Then I looked and I was like, I knew in my head, I was like, yeah, I wanted to say you’re. Yeah, you’re
dropping significantly down. So obviously I was like, okay, this is interesting. Weston’s a very smart guy. Why is he
taking this 80 pay cut? And so fast forward and obviously it was the right decision, but what. Yeah, I guess. What
was it like making that decision? We had to do lots of calibrations in the financial plan. You live in Austin, it’s
expensive city, obviously you have an amazing life that was supportive and was still, you know, working full time.
But yeah, I guess. What was that like?
Speaker 3 – 05:27
And what made you ultimately make the decision of like, here’s a very stable company that just IPO’d. You know,
we won’t talk specifics, but, you know, a traditional, very good salary and incentives to now taking this 80% pay cut.
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Speaker 1 – 05:43
A couple people have given me advice, but it really all falls into that Jeff Bezos regret minimization framework.
Like, in 10 years, what are you going to regret having not done more? And, you know, I learned a lot of Dropbox. You
know, I’m a fairly younger guy. I was young in my career. So actually when I, my first job and I moved from
investment banking to Dropbox, I also took a pretty good size pay cut, but knew I was going to learn a lot and grow
in that business. And then, you know, ended up working out, moving to Procore. It wasn’t like a huge financial uplift
for me, but it was a company I really believed in and again did well. And then.
Speaker 1 – 06:16
So I had luckily had some fortunate outcomes through those businesses and was still young enough to look at this
as like, hey, I’m making 10 year bets. And the decision that maybe makes sense for a week or a month or a year or
even a couple years can be different than the decision for 10 years. I’ve always wanted to start a business, own a
business. So I thought, you know, now’s the time to try it. And, you know, obviously in the short term, it can be a
little risky and painful, but, you know, what’s the worst that happens? You know, it doesn’t work out and then you go
find something else.
Speaker 3 – 06:46
Like I just to be clear, you took that 80% pay cut that came with a potential, not a guaranteed upside. You got some
equity, you know, in this company called closing Lock. And so you really believed in Andy. Like you say, he’s, you
know, personal friend. Can you just share with us, basically? What did Closing Lock do at the time that you joined? I
know it was like a pretty fresh startup at that point. And how, what role did you take on? How has the company
evolved since then? Both from a servicing offering, but then if you’re comfortable or allowed to share, you know,
what do the numbers look like? Like whether that’s revenue or client base or whatever you’re allowed to share.
Speaker 1 – 07:29
So when I joined Andy, it was just him. There was a kind of a bare bones product. So we’re in the real estate space.
So anyone who’s bought a house can tell you that, you know, homeownership is the American dream. Buying a
home is awful. It takes a long time, there’s a lot of paperwork. But the area that were most particularly interested in
was the movement of the money. So if you’ve ever paid for a babysitter, you probably used Venmo or if you bought
something online, use Apple Pay. When you buy a house, you’re typically writing a check or issuing a bank wire,
which is something that most folks who aren’t in the financial services industry have never done before. It’s very
1970s, 1980s.
Speaker 1 – 08:07
Like, you go to a physical bank branch, you take a long string of numbers, you key it in and you’re like, did that go to
the right place? And they’re like, we don’t know, we’ll let you know in a couple hours. So it’s a really cumbersome
process for anyone who’s done it. It’s also unfortunately very risky for fraud. So that’s what really started to pop up
kind of in the late 2010s was fraudsters had figured out, hey, I can just trick someone into wiring money to me
instead of to a title company thinking they’re buying their house, and then next thing you know, that money’s gone.
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So the whole payment system for real estate was terrible. So our original idea was just simply a portal where you
could securely share wiring instructions. So instead of emailing wiring instructions, you use a secure portal.
Speaker 1 – 08:49
So you feel a lot better that you know, you receive them from the right party and that they are, you know, the right
instructions to follow. And we would sell that for a couple dollars a transaction. So we had a modest couple
customers, enough revenue to kind of, to just again, pay two of us about 20% of what were probably worth in the
market. And from There we kind of grew, but the vision has always been to build a payments infrastructure that
supports real estate. So we call it like Venmo for real estate. Why can’t you buy a house from your phone easily,
securely, no risk of fraud? No. No wires, no checks, no, you know, physically driving, you know, a check to an office.
So, so that was kind of the goal.
Speaker 1 – 09:29
And we’ve really since now evolved into this platform that supports closing and protects really all the parties,
lenders, agents, buyers, sellers, title. You know, it has insurance, it has documents, it has communication. So it’s
really evolved into this secure closing platform and we’re continuing to try to modernize how homes are built. But,
but that was what was really exciting because I saw that the fraud is the obvious thing. If you talk to a title
company and you say, have you experienced fraud? Are you worried about fraud? The answer is always yes. So you
solve that problem. But then fraud isn’t really the problem. Fraud is the symptom of the problem that there isn’t
really a easy, secure way to move money in real estate.
Speaker 3 – 10:09
So remind me the date you joined or what year you joined.
Speaker 1 – 10:13
I joined in early 2021 and it was just the founder in me.
Speaker 3 – 10:18
So fast forward five years. What does closing lock look like today? Cause I followed your company and your
growth and it’s crazy. Obviously crazy growth, which is exciting.
Speaker 1 – 10:28
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Yeah, it’s great. So we’re now up to a hundred employees. We’re here in Austin, Texas. We service a, you know,
quite sizable amount of the US real estate market today. You know, we’re approaching a thousand customers,
which we’re really proud of and continue to grow. So we’ve raised, you know, we’re a venture backed business, so
we’ve raised now $50 million in a couple different funding rounds to grow and we’ve really been focused one, just
expanding our team to service more and more customers. But also we’ve invested a lot of money in R and D to
continue to build out this payments infrastructure because real estate is, it sounds easy. It’s like, hey, I can just pay
you like I, you know, pay my babysitter. But there’s a lot of complexity, a lot of compliance risk laws.
Speaker 1 – 11:07
So there’s a lot of stuff to do there and we’re trying to, you know, support all of the flow of funds. So it’s a lot of R
and D investment, but also just growing the business and it’s been a really Fun ride so far, I.
Speaker 3 – 11:17
Would say, Jameson, because you’ve had so many experiences recently with, I want to say, like, so Weston hired, I
know you were like the COO to start and still are as your role has evolved, 100 people. So if one of those hundred
people are listening to this podcast, let’s say it’s another startup. Jameson, you’ve recently worked with those
people. You know, what are the biggest concerns that you see or ramifications of having a financial plan and then,
you know, what questions you have for Weston that you think these people would love to know the answers of in
advance?
Speaker 2 – 11:54
Yeah, I was gonna say, well, a few things there. Number one, like, when you talk about people in this situation, I
think some insight you can give Weston is like, we don’t need to get into details like the difference between, you
know, what’s venture backed, PE backed, etc, and I think what I want to highlight is like these people, they’re
wealthy on paper. So, you know, a publicly traded company has a live price to it every single, you know, as long as
the market’s open, you can see what that’s valued at. Something that’s in the private market is kind of is the
opposite of that. Whereas, you know, you don’t have to report, you don’t trade on the stock exchange.
Speaker 2 – 12:33
So it’s maybe once or twice a year the company does and could be more evaluation for a 9A and then that’s what
that stock is worth. And a lot of times that stock, you know, you can only get paid out if there’s an ipo, an
acquisition, sometimes there’s tender offers, you know, maybe the company will buy out some of the equity in
some situations, the company obviously would have the cash to do that. So I’d say, Matt, to answer your question,
the biggest thing is you’re rich on paper and you’re kind of building a plan where could be anywhere from 80 to 95%
of your net worth is tied up in this like home run asset that may hit and may not. And even if the business is
successful, you may not get any liquidity out of it.
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Speaker 2 – 13:12
So Weston, what’s like maybe give an overview without getting too into the weeds about like, you know, something
that’s venture backed, PE backed, what a liquidity event would look like, how that happens, you know, to kind of
speak on this like rich on paper reality.
Speaker 1 – 13:27
Yeah, no, it’s something I’ve really enjoyed learning a lot about. So we’re in the venture backed category there and
there’s a pretty clear goal there. So A venture investor is typically funding a company that’s in the early growth
stages with the goal of having a very large outcome with the company growing significantly. So they tend to have a
longer time horizon. Most early stage investors, you’re looking at five, seven, even 10 years from when they put
their money in to when they’re thinking about some sort of exit private equity, which we haven’t personally dealt
with, but that you tend to see that more in the later stages.
Speaker 1 – 14:02
It tends to be more focused on, you know, established businesses and they’re still looking to grow and improve the
profile of the business but it’s often something that’s a little more established and they might have a shorter time
horizon depending on the scale to either, you know, sell to another private equity firm, take it public. Oftentimes
private equity will take a group private and then, you know, merge it with another group and then take it public. So
they’re looking for more of the quick flip. Again they all have their own kind of flavors and investment profiles. But
yeah, the interesting aspect of venture is you’re often looking at 5, 7, 10 plus years until you have your major
liquidity event which is definitely something you need to consider from a, you know, personal financial standpoint.
Speaker 1 – 14:41
Especially with, yeah, like you said Jameson, my situation is the same. I have the vast majority of my, you know, on
paper net worth is in one illiquid asset. So certainly leads to a lot of pondering and sleepless nights kind of
thinking through the different scenarios and how they play out. But it’s just good to know, eyes open, going in, kind
of what you’re getting into.
Speaker 2 – 15:02
What’s like the emotional side of like. Because I’ve seen people in a situation where they get like super tied to this
outcome of like, you know, they don’t I guess take a step back. Our advice would, is generally like let’s participate in
the upside but let’s take some chips off the table so that you know, let’s find that floor of what do we want to
secure as far as goals? What’s that dollar amount we need, how do we get there? And then let’s leave enough
upside where you know, if the business succeeds, you can participate. So like talk about a little bit like the
emotional side of how you kind of don’t get too high, don’t get too low, don’t get too tied to the outcome. Like how
do you balance that?
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Speaker 1 – 15:38
Well, first of all, it’s hard. I don’t think I have like A great example of, you know, a certain meditation or something
that’s going to kind of work. But I do think it’s important to completely separate that as not really worth anything.
It’s, it’s just potential upside. You know, even just like very tactically, like if you’re looking at some sort of like you
have a personal financial app that calculates, you know, net worth or anything like that, don’t put anything in there
about your, you know, equity in the company. It’s only going to make you feel richer than you actually are. Like,
that’s complete funny money. You know, you kind of certainly think and hope and dream about what it could be.
Speaker 1 – 16:14
But I think it’s really risky to rely on some sort of outcome there because things can go, you know, in all different
directions, up, down, sideways, and then just you know, not really getting caught up in that day to day valuation.
Luckily, a private company isn’t on a stock exchange, so you’re not watching your stock price every day, but you
certainly know how the business is performing. So I think you just have to really kind of get that out of your head.
Now one cool thing that’s we’re seeing as a trend in the industry recently is this concept of like tender offers or
secondaries. So businesses that start to reach that series B, series C plus stage, you often have an opportunity to
take money off the table. And I’m fully of the mindset that you should do that.
Speaker 1 – 16:55
And it goes back to that regret minimization framework. Right. You know, let’s say you have, you know, a business
where if it does really well, you’re going to make 25, 50, $100 million. It doesn’t really matter if you made $5 million
less because you sold some upfront to take money off the table. Like, no, I don’t think you’re going to have an
outcome where you make that much money and you go, man, if only I had an extra 10% or 15% on top of this crazy
number, that would have been a huge difference maker. I could definitely tell you’re going to regret not having taken
some if the whole company goes south.
Speaker 1 – 17:30
So, you know, I, you know, an example someone told me once, which I think is interesting, is if you could have a
million dollars today or flip a coin for $10 million, which one would you do? And you know, on math, you can do the
Math, right? It’s 50%, $10 million outcome. That’s a $5 million value to flip it. So you flip it, right? But like most
people you would ask that would say, no, I’ll take that million, because how terrible would you feel if you flipped it
and lost? So that’s a good thing to think through in your head. And I think most people, if you haven’t had a huge
financial outcome, you’re probably taking that million. Now if you ask someone who is already worth 15, 20 million
dollars, they’re probably going to flip, right?
Speaker 1 – 18:11
But just think through that in your head and if your answer is, I’ll take the million rather than flipping that coin, then
you probably need to take some money off the table.
Speaker 2 – 18:19
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I’d say too. And that’s a really good analogy. It probably will help you make like having some of that security in
chips off the table, whatever that number is, probably will help you make better decisions because you’re not so
stressed on the outcome of the business.
Speaker 1 – 18:35
Because the other situation you can run into is when you raise money, you can run into diverging incentives. So you
know, if you’re a founder, early employee and you’re well into the money and your net worth on paper is substantial,
you really want to press and risk that business to make it 4, 5, 10 times the value that it is. Maybe not. But if you’re
the venture investor, you maybe do. So I think it is win to take some money off the table because then you now
both have the incentive to play aggressively with what’s left versus you’re a little more risk averse if all of it is tied
up in that and you’re trying to avoid that complete zero outcome.
Speaker 3 – 19:10
For sure. I totally agree with you, Weston. And some of the best founders and also operators are those that are
already financially secure, you know, because they can do what’s in the best interest of the company, what’s the
team members of the clients. You have to balance those three things together. Right. I remember having
conversations with you. You’re just taking this 80% pay cut. There’s probably a lot of people in your shoes that
have, you know, done something maybe not that drastic that was a little crazy. No offense, but it obviously panned
out for the best. So 80% pay cut and then you had opportunity that you know, you andy just hit the ball of the park
early on. Massive growth in the first couple years. I can’t remember exactly, you did have the opportunity to take
some chips off the table.
Speaker 3 – 19:50
And I remember having the conversations of exactly what you talked about. Regret, min. Regret minimization is
what Got you this job and now regret minimization is basically how much you let continue to ride versus how,
remember the conversation. You have young kids, you know, you’re obviously in Austin. It’s not a, a cheap place to
live. And you know, what would money mean today where your kids are under your roof versus not knowing when
this was in a cell? And what would more money mean when, you know, maybe your kids are older? Some of the
opportunities and memories of being in a nice house. And so, you know, walk us through that decision process
from your lens because I, I can talk about it from a financial planner’s view because I was involved in those
conversations.
Speaker 3 – 20:32
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But I think our audience is doing much better looking at, you know, what were the stress or all the stresses and
what ultimately made you pull the trigger on taking some chips off the table, knowing everything was going so
well. And looking back, it was like, well, everything did so well. So you didn’t necessarily extract every dollar you
could have out of the company by any means.
Speaker 1 – 20:57
So yeah, I was fortunate enough. We raised a round of money in early 25 and the investor had given us an
opportunity to sell some of our shares in a secondary sale in that scenario. So that’s a delicate balance because
when they ask you that, you’re, you know, you’re kind often thinking, is this a trap? If I’m, if I’m trying to sell a bunch
of it, are they going to think what this person has no confidence in it. So had a couple conversations with them.
They, they gave kind of a rough range of, you know, what they would be comfortable with us selling. And, and we
actually, you know, I came in at about half of what they said would be kind of the top limit. So it’s enough to, no
matter what happens from here on out, feel like this was worth doing.
Speaker 1 – 21:38
And you know, I’m not like, you know, I’m not sweating kind of day to day money, but it wasn’t so much that I’m
going to, you know, regret if this company continues to grow and do well having sold a lot. So I think, yeah, it gives
you a lot of comfort to, you know, pay off a mortgage, buy a new house, you know, kind of take care of kids, school,
like all the things you’d be doing in a more traditional career kind of saving up. And then it eliminates kind of the
month to month stress of worrying about, okay, I need to be saving X dollars per month, you know, to hit some
certain goal.
Speaker 1 – 22:08
It really does kind of Knock out some of those kind of, you know, big early wins that you would typically focus on if
you’re kind of doing personal financial planning. Yeah, house, cars, debt, kids, you know, and then, you know,
obviously were sensitive to not raising our lifestyle substantially. Like I, I felt like we had, you know, taken enough
where and invested it wisely. So if, like, if we just kept going how we’re going, like it’s, you know, we could do it for a
good amount of time and not feel like we had to move it because that’s the hard part. I’m sure you guys know this.
You talk to clients all the time. Like moving your lifestyle backward would be extremely painful. So were very
careful to not use it necessarily to increase lifestyle, actually. Joke.
Speaker 1 – 22:50
You know, of our 100 employees, I drive the crappiest car. I have a 2013 Toyota Corolla. It’s totaled from hail
damage, its engine light is on, and that’s fine. So I, I, I didn’t go out and buy like a super nice car. I didn’t, you know,
go out and buy like a crazy house. Like I, I basically just said, all right, this is my risk mitigation. You know, it’s
enough that no matter what happens the next few years, I’m going to look back on this and say this was worth
doing. And then, you know, whatever I get, you know, next will kind of allow me to grow my lifestyle. But I didn’t
necessarily use it to kind of put me on a path where I would need additional money from this to continue to live
how I live.
Speaker 3 – 23:28
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Yeah. Looking back, I think it almost a framework that I think would be helpful for people to think about is you
know, we took enough as like, okay, there was, we don’t have any regrets for doing. Even if something, God forbid
happened at that point, that 80% pay cut up for those four years was worth it. What you would have been able to
save in that higher paying traditional job. You’re back on track to where you would have been and we’re more on
track than we ever would have been. Now there’s a second psychological pivot that I think would be really helpful
because at this point now it’s like, okay, the company has just crushed it. And so you have this, you know, you’re
back on track. Let’s say it’s more accelerated on track than you ever would have been.
Speaker 3 – 24:12
Now you have this, we’re living this conservative lifestyle, but now we know that the company has, you know,
whatever 10x. And so now you have this big asset. You can’t touch it. How. What’s the framework in your mind of
like, okay, are we going to have regret now if this, if I don’t get this money five or ten years from now, and we should
we be increasing our lifestyle knowing that’s likely. How, how are you balancing those decisions where it’s like,
okay, if I don’t get this money till later, it’s like, why, you know, why did I drive this Toyota corolla for these 10 years
when now I have more money than I’m ever going to spend? So how does that decision framework work on your
mind right now?
Speaker 1 – 24:56
Yeah, that’s tough. You know, I think the cool thing about being in the position I’m in is you do meet a lot of other
people in similar situations, so you form this kind of community. And then you also meet a lot of people who have
been through that where they have received a large amount of money. And you know, the thing, you hear this all the
time and I think no one believes it, but having talked a lot of people, I do believe is like, it doesn’t change your life
that much. Like, if, you know, if one day you get a check and, you know, your net worth goes from like, modest to
$50 million, like, I don’t think you’re going to be a different person or a lot happier.
Speaker 1 – 25:30
Like, you know, and oftentimes in this stage of life, if you’re kind of in your 30s or 40s and you know, you have kind
of roots somewhere, you don’t necessarily want to, like, up and move to a new neighborhood and buy this huge
house. So it’s almost just like minimizing, like, what effect that is going to have on you. Like, I, I hope it works out
so I have the chance to, like, take care of my friends and family, of course, enjoy a lot of nice vacations, but, like, I
don’t have my eye on some like, huge mansion and like, crazy lifestyle and private jet and like, because one, I mean,
that may not happen. And then two, it’s just, I don’t know that’s going to make you happier. So it’s almost like
completely reorienting your relationship to money is like, it’s a tool.
Speaker 1 – 26:08
It, you know, it buys comfort, it buys a lot in your life. But, like, I don’t think it’s healthy or I’m not trying to live a life
where like, for the next five or ten years, I’m like, oh, man, as soon as this happens, then I’m going to be happy.
Then I’m going to feel like I need it because I just think that’s a terrible way to live those five or 10 years. And I think
you’re going to be really underwhelmed once you hit that.
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Speaker 2 – 26:28
I think that’s like a great lens to view that through. And so, like, how do you. So that the people that I’ve seen do
this, kind of navigate this? The most successful have been like, super, intentional, thoughtful, deliberate about, like,
what are your values? What are your goals? What do you find purpose in? What’s your meaning? And then kind of
using that to reverse engineer what you want the money to, how you want the money to support that. So, like, it
sounds like you’ve done a lot of that thinking. Like, when you have kind of thought through this over the last, like,
five years, like, what have you boiled down to? Like, hey, this is the most important thing. I want to make sure, like,
these things are secured. Like, how have you thought through those goals?
Speaker 1 – 27:04
I mean, first for me is family. I have two kids and a wife. I want to make sure that, you know, no matter what
happens, that they are going to be okay and they’re going to be safe. Whether that’s, you know, an untimely kind of
death by me or the business goes, you know, belly up. Like, I first made sure they’re okay. So, you know, making
sure their education is fully funded, making sure that we don’t in a situation where we’re going to owe a bunch of
money on a house or have a bunch of other debts or obligations. So, you know, that foundational stuff is taken
care of and then just enough saved away that, you know, and then adding, you know, insurance. I think insurance is
a unique angle here.
Speaker 1 – 27:35
Like, you might need a little more insurance if you’re in this situation and you don’t have a ton of liquidity to make
sure that, you know, they’re taken care of. But just first making sure the foundation is there, and then from there,
you know, we prioritize our spending on stuff that makes our lives easier. Because the other thing people don’t talk
about is, you know, the time and stress that goes into a building a business is a lot higher than it is, you know, for, I
think, your kind of more traditional kind of corporate job. So we, you know, where we spend luxuriously is. It’s one.
It’s stuff that’s month to month. It’s not stuff we’ve bought.
Speaker 1 – 28:12
So instead of buying a nice car, instead of buying a nice boat, you know, we’re doing things like paying for, you
know, cleaners and laundry service and you know, health and wellness and you know, helping with getting meals
prepared. A lot of help with watching kids. Like these are things that, you know, make our life today easier, but
they’re also like not long term financial commitments. Like if we needed to reduce those, we could at any point in
time. I don’t have to scramble and sell a vacation home or a boat or you know, I’m not like, you know, I’m not
financially beholden to these. But that’s so, that’s so foundation and then just making life as easy and stress free
as possible. You know, part of that is candidly like and having people to manage your money and finances.
Speaker 1 – 28:51
Like I, I, I really, I view my liquid net worth, it should be boring and automated. Like I’m not getting like, I’m already
like cranked up enough day to day at work. Like with the wins and losses of building a business. Like I don’t need
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to be checking like Bitcoin or like stock prices. I’m not trying to like, you know, you think about in the framework,
like why would you try to make asymmetric wealth there? Like you’re not good at it. You already have this other bet,
like have it boring, have it automated and focus all your time and energy on something that is, you know, you can
control and then maybe don’t seek some of those other things outside of it. I think is how I’ve approached the
money so far.
Speaker 3 – 29:27
Weston, any advice you’d have for someone considering a, that has an opportunity to join a startup company,.
Speaker 1 – 29:37
You know, maybe.
Speaker 3 – 29:38
Take a pay cut, but then had equity offered to them, what advice would you give to them? Both from a decision
process for them individually, but then also evaluating the company that they’re joining and the upside. How would
you look at those two frameworks?
Speaker 1 – 29:53
Well, so from a decision process I do think you need to be comfortable with worst case scenario. So if you’re
joining an early stage company, a lot of my friends have done this. I’ve been lucky. Everything, you know, you can
do all the homework you want and it can’t work out. So you just have to be comfortable with, you know, that risk.
Now what I will say giving advice to people who are maybe a little more reluctant is when it fails, it typically fails
fast. So what’s the worst that happens like, okay, you go there, you spend three months, six months, 12 months
and it doesn’t work out. Like, okay, you learned a lot. You know, those skills are extremely valuable. I mean, as we
hire people at Closing Lock, like we’re looking for people that have taken big swings and failed.
Speaker 1 – 30:32
So I, I think this whole concept of like, oh my gosh, you left your job like you’re totally screwed, you’re never going to
get to go back. Like, you could easily go back and get a job probably at a level based on all the things you learned
in the risk taken. So, but you need to, you need to be comfortable with like, yeah, like this might not work out from a
company perspective. This is also something I’m really passionate about is, you know, you need to be a really good
company picker. So in a way you are an investor, but instead of investing money like a venture capitalist, like you’re
investing your time and energy. So you need to really understand what is this company, who is running it, you know,
realistically, what is the outcome that you could see.
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Speaker 1 – 31:10
And then you want to also match the amount of money they’ve raised to what you think they’ll have to do. So you
see a lot of these companies in the news and they raise a lot of money at a high valuation. It’s super exciting. But
you should know going in like, hey, like people that put a lot of money to a company want a lot of money back. So if
you’re joining a company that has, you know, billion dollar, multi billion dollar plus valuation, super exciting but like
that you’re going to need to grow that 5, 10x to really see return. And like, is that realistic? So you know, when I
joined a company, you know, no funding, so you know, no funding, modest funding that comes with its own risks.
But you don’t have to have this huge home run.
Speaker 1 – 31:46
You know, you can start to kind of grow and buy time and then you start to get money when things are working.
That’s I guess what I would say is like you use money to double down on what’s working. Using money to kind of
dabble and find out what works is dangerous because if you don’t find it, then you know you’re kind of screwed. So,
and then in terms of like just the basics of understanding a business, you know, there’s really a couple key factors.
So you know, one is obtaining customers. Sorry, I’ll start there. So how easy is it to obtain a customer? How much
does it Cost to obtain the customer and how much is the customer worth to you? So in the industry terms that’s
called customer acquisition cost. And then the value of the customer is called lifetime value.
Speaker 1 – 32:31
So, you know, is it hard to get a customer? Is it easy to customer? How long does it take? How many
conversations, how many people, like, just really understanding the level of money and effort it takes to acquire
them. And then the next one is how well do they retain customers? That’s probably the number one stat. I used to
joke because, you know, when I would interview for jobs, you know, back when I was at Dropbox or whatever, like
most recruiters, you know, when they’re talking to prospects, they’ll ask things like, well, what’s their healthcare like,
what’s the office like? My first question was always like, what’s their net dollar retention? And they’re like, what?
Speaker 1 – 33:01
So that’s the concept of like when a customer, you know, is when you have a customer in the business, are they
sticking around and are they paying you the same money, more money or less money than when they started? So
net dollar retention, you want to see customers that join, you want to see them stay because that means they’re
continuing to get value. And then you want to continue to add, you know, goods and services that they’re willing to
pay you more for. So that’s called net dollar retention. So if you can acquire a customer, again, this is regardless of
what industry and tech services, if you operate a cleaning service, right, you’d say, okay, how hard is it to find
someone whose house I can clean? And then on average, how long do they keep my services?
Speaker 1 – 33:39
So you want to ask those questions. So customer acquisition costs and net dollar retention are probably the most
important. And the last one, I think is just looking at product roadmap, like, what else can you build? And then
realistically, is that something that kind of, you know, because you do the service you do today, does that allow you
to do something else? So for closing Lock, you know, our original product was software that helped securely
exchange wiring instructions. So it’s a natural extension. If people are getting wiring instructions from us to say,
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hey, do you want to just pay? You’re already downloading basically a PDF document with instructions on how to
pay. Do you want to just pay right here? Like, that’s a natural extension.
Speaker 1 – 34:14
If closing market was like, hey, we’re now going to start selling T shirts, it’s not really a natural extension like people
that are getting wire instructions, there’s not really an unfair advantage for us to Sell them a T shirt. But like, you
want to kind of understand the evolution there.
Speaker 3 – 34:27
I’d buy a T shirt though. Just FYI anyways, though.
Speaker 1 – 34:32
So, yeah, so if you believe all those things, if, you know, if you can acquire a customer, if they’ll stick around, and
then if you have kind of a realistic way that you can, you know, build more value for those same customers, like,
that’s where the flywheel starts running and that’s how you can really grow.
Speaker 3 – 34:44
Because advice to business owner that’s privately held. No, venture, no, PE hasn’t. What, what considerations
would you give to them of, you know, why you should or shouldn’t sell? Take some chips off the table by selling.
And what have you noticed been the differences between when you were, you know, before funding came in versus
after? Yeah, just a, a transparent conversation around that I think will be super helpful.
Speaker 1 – 35:14
So we talked earlier in this conversation about different flavors of investors, private equity, venture. We did, you
know, what’s called a friends and family round and angel round. So that’s kind of, you know, individuals that are
usually your friends or family or they joke the friends, family fools. But the first thing is you need to have aligned
expectations of what this investor wants from this investment. A lot of investors, when they put money in, they
want to see it used to grow. So they’re going to want to see you put it into the business to again, acquire more
customers, build more products, grow the business. Others may be comfortable just saying, hey, I’m going to buy
from existing investors. And you don’t really have to change anything about your business. Just keep operating it
as is.
Speaker 1 – 35:54
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So that’s the first thing is like, who is this investor and what are they going to want out of this? And does that align
with what you want? Because you can end up in a weird situation where they’re going to want you to aggressively
grow, raise more money, you know, candidly burn money. Like a lot of companies that raise venture money are
losing money every month. I remember explaining that to my parents because they were, you know, an early
investor. And, you know, they’re like, how’s the business going? I’m like, great. And we talk through kind of the
financials. Like, wait, you lose money every month? I’m like, oh, yeah, we lose a ton of money and I hope we lose
more because we’re pouring it into growth. Right. But that’s.
Speaker 1 – 36:26
If you don’t understand that, if an investor doesn’t understand that, they may be the opposite. They may say, hey,
stop Spending money, stop trying to grow. Like, I, I’m expecting monthly or quarterly checks. While, while another
investor might say, you know, jokingly, we would talk to venture investors and you know, if were like profitable or
near profitable, they’d be like, this is insane. Like spend way more money and grow. So it’s, it is, it’s fascinating how
they have different lenses. So you really want to make sure that, hey, Mr. Mrs. Investor, like, what do you want out
of this investment? Like, where do you kind of see the business going? And then make sure that’s something that
you’re comfortable with and aligned as well.
Speaker 1 – 36:59
And then like I said earlier, I do think taking as much money as you can responsibly take off the table is just a
smart move. It does, it’s not an indication that you don’t believe in the business. It only sets you up for kind of
longer term success. So I think most people kind of look at like 15 to 30% of the chips you can take off the table. I
think that’s a really healthy range. So whatever you have liquid, I would look at, you know, 10, 15, 20% easy, maybe
even up to 30% depending on how long you’ve been doing it. And, and that’s just a smart move.
Speaker 3 – 37:31
That’s just smart with, for a business owner that’s already financially independent, already has those chips, let’s
say, you know, not. Because obviously tech is completely different and it’s, you know, you need a large amount of
money that typically a founder is not going to have until the company sells to get this thing, you know, up and
running. But let’s say someone has a conservative amount of liquid net worth that is separated from the business.
They’ve been disciplined savers and they have the business and it’s still privately held. What are now. So there’s not
the need to take the chips off the table, but the bigger the company gets, the more stuff that could go wrong where
those chips may have to come back in because you’re, you are the business and you’re funding it. That’s a lot of
the clients we work with.
Speaker 3 – 38:15
What would be your decision matrix or decision process for still taking chips off the table? What would the venture
capital pe, what would you be looking for them to bring to the table at that point?
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Speaker 1 – 38:26
Yeah, well, they’re going to bring industry expertise. So you want an investor that understands your business, that
has invested in something similar and then you’re obviously going to want them. You know, you’re going to Want to
talk about what you know, how much of this money is going to taking chips off the table versus investing in the
business. So I, I think that’s, everyone kind of has to make that personal decision because the other thing you run
into is if you own, if it’s a private business, it’s your business. Like there is a luxury in owning it and not having
anyone to an to if you have investors there’s often a lot of, you know, rights and covenants that they have. So you
need to make sure you’re reporting correctly to them. You make sure you have like a robust financial plan.
Speaker 1 – 39:01
So you really do kind of give up some control there. So if you, if you want more liquidity, if it’s going to help you
from your life or you know, you think it’s going to unlock some stuff, then you should do it. But it’s not as it often
comes with a lot more hooks than you think.
Speaker 3 – 39:14
Sometimes it’s a no brainer necessary. Sometimes people should, you know, reconsider is what I’m hearing.
Depending on your industry and your personal financial situation and what’s the goal of the company and you
know, is growth the most important thing or do you have a customer base that you’re happy with supporting as
best possible, etc.
Speaker 1 – 39:31
You know, people in the investing community use this term lifestyle business and it kind of comes across
condescending. But like I think those are the best businesses. Like you have the ultimate flexibility and control, you
know, so I think you really need to think hard before you give up a business that you control completely, that is
cash flow positive because you’re, you are going to take a lot more risk, you are going to have a lot more people to
answer to and the upside’s there. But again like at some point, you know, the incremental dollar you earn isn’t as
valuable. So it goes back to like what is money View? You know, if you have a couple million dollars, what does 10
million get you that you don’t have now? What does 20 million get you? And like is that really worth it?
Speaker 1 – 40:07
Like you know, you really got to think about that.
Speaker 3 – 40:10
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Absolutely. Well Jameson, what are some, you know, from your recent conversations with some of our the clients
that have private wealth, what are some other questions you think would be most highest impact for you know,
listeners? Either business owners thinking about making the transition to a partner of a private equity or venture
capital or on the flip side, an employee that’s making or you know, a high income or that’s thinking about making a
high risk career switch to a startup like this. What, what are some of the questions that we can leverage Weston’s
expertise?
Speaker 2 – 40:39
Yeah, just say one thing that I think especially if you’re, if these types of people are younger, so let’s say 20s, 30s,
40s versus you know, if you’re in 50s, 60s and later stage of life, like trying to balance like so you have this big, this,
these assets that could grow tremendously. How do you balance like keeping. We’re going to get a little bit
technical here but like as far as estate planning, like I hear this a lot from businesses or business owners or we’ll
say like let’s take some of this asset and move it outside of your estate into a trust. And you know, the benefit of
that is if it hits, you’re avoiding a ton of estate tax. It’s asset protected, credit protected.
Speaker 2 – 41:20
But I’ve seen with younger business owners, key employees, it’s really hard to wrap your head around that because
like you’re, you have such a long Runway of your life and you don’t really know what’s going to happen. So like how,
and I believe you guys have thought through that with some of the closing lock stuff. So what, like how have you
thought about that and what advice could you give to people? And a lot of what I hear is like, I don’t want to give up
control of the asset. I want to still be able to like use it and control it. So how have you framed that decision?
Speaker 1 – 41:51
So the great thing about early stage companies is they’re virtually worthless on paper. So you can do a lot of stuff
there to, you know, take advantage of, you know, mitigating tax risk. So you know, one is, you know, a lot of times
the compensation or the equity you’re going to get is in the form of a stock option. So you need to understand, you
know, 83B elections, 409A’s, what is the fair market value of that? Because oftentimes when the shares are issued,
the spread between, you know, the strike price and the fair value is zero. So exercising them has a lot of
advantages because you start the clock on longer term capital gains. So you definitely want to talk to an advisor to
understand that and then trust.
Speaker 3 – 42:33
Yeah, Weston, I think you’re really like a poster child for like all of these steps along the way in your 20s, you know,
with Dropbox, the Exit and then Procore, you were a discipline, you lived a good lifestyle. But you were a saver.
Definitely would categorize you as a saver over a spender. And I think that was really a catalyst into, you know, your
biggest hopefully already in. In the future will be closing lock just because you got in from literally ground zero. And
so I don’t think an average person would have been able to take on that amount of risk. So you had to do good
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planning leading up to that 80% pay cut, which you did. So that’s the importance of. Sometimes people think, I’ll
save later.
Speaker 3 – 43:15
No, Saving in your 20s puts you in the position to take risk because I would say you took the biggest risk of your
life, not when you were that young. And so I think a big misconception is like be risky when you’re young, older.
Well, if you look at your trajectory, a sales job, it drop. It was no brainer to take that. But it was like you took the
most risk actually in your, I would say right now in your 30s. But what you did in your 20s really set that up for
success where now in that risk you’re able to also do all these advanced techniques. We took some chips, but, you
know, there’s a lot of steps and anchoring that had to happen to get you here.
Speaker 3 – 43:53
A person that hadn’t done that planning probably would have had to take a lot more off the table than you do. So I
just want to reiterate, good planning, even if you’re not at this stage, can be a huge catalyst to when you do have
this type of opportunity to really do the right planning at the time.
Speaker 1 – 44:11
Yeah, it’s so much easier. I mean, I’m lucky to have parents. That kind of, you know, taught me the value of saving.
It’s so much easier when you’re younger. I know you don’t make as much money, but like, you don’t have kids.
Daycare is expensive. You know, you need a bigger house when you have kids or a family, you know, you’re not just
thinking about yourself, you’re thinking about your partner and you know, your future. So it just, you have. And then
obviously the compounding. So like it does, it’s a sequence of steps. So if you really want to take this path, you
have to start early. I don’t think many people. I certainly couldn’t have taken that huge pay cut if I hadn’t taken those
steps early to feel comfortable.
Speaker 1 – 44:45
And you know, I talked to my wife and you know, we had this kind of mental model of like, let’s one year like, we can
handle this for one year. And if in a year it goes belly up or it doesn’t really show promise, then no harm, no foul,
we’ll go get another job. You know, you lost a year of savings, right? But like that was fine. We, so I think that’s a
good framework for other people. Like you can give it a good honest year and if things haven’t really moved
material in a year, then you probably need to start thinking about, you know, other scenarios. But like that’s long
enough to really see if something’s going to work. It’s not going to obviously, like you’re not going to get money
back in a year.
Speaker 1 – 45:20
But like you’ll be like, okay, like it’s growing materially, we’re heading in the right direction. But you have to set
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yourself up to be able to take that risk. And you know, I was able to do that with, you know, working with you guys
and just being kind of frugal in my 20s so that I could take this risk because I did know from a very early age that I
wanted to do this. But if you’re, if you don’t set yourself up for that, then you just, it’s a risk you can’t afford to take.
Goes back to the at point flip.
Speaker 3 – 45:44
Well, Weston, you’re batting 100. You’re three for three now. Dropbox Pro Core and now closing blocks already. You
know, the success he has had already call it a huge success no matter what happens from here. So
congratulations. But one other thing as a closing point I’m gonna, because Weston’s a perfect example for this, is
that when you take this path that’s maybe not a traditional path where you have, if younger or older, if you have a,
you’re accepting this lower salary for this equity, the people that close and locker and a startup you know, are
recruiting. If you already have startup experience, you’re almost indispensable because, you know, look at you,
Weston. Procore hired you probably because your Dropbox experience. Andy saw what you did at Dropbox and
Procore was like, he’s a no brainer because he’s seen everything at this point.
Speaker 3 – 46:35
And so the skill set you get in a big established corporation is going to be very limited. If you’re number 10 at a
startup company, whether you like it or not, your job description isn’t going to be exactly what it is. You’re going to
be doing a lot of things for every department, you’re going to be doing everything and so you could view that as a
bad thing. Like, I’m not, I’m already getting underpaid, I’m. Or you could view that as, hey, if whether this works out
or not, I’m going to be able to provide so much value to any startup that’s out there because I’ve seen it all. And
that I think is in, that’s going to be worth depending on the person, if you’re early in your career, more than any
equity would be worth is getting that under your belt.
Speaker 3 – 47:14
Because all of our other clients we’ve seen is like the client that was like one of the first hires at Stitch Fix, you
know, who they IPO’d and with a couple of those. And now they’ve, they’re constantly getting recruited for these
new startups and getting equity like immediately offered. Like it’s, this isn’t. They’re interviewing for the job. Like
these startups are begging them and recruiting them, throwing these big dollar amounts and big equity, you know,
equity percentages at them to get them because they bring that knowledge base. So highly encourage. It’s not as
big of a risk as you think because that skill set, you know, Weston’s a perfect example of that, you know, really
carries forward.
Speaker 1 – 47:51
So it’s not just your money that compounds, it’s your knowledge. And you know, you, I, you probably heard the
cliche of like, you know, first third is learn, second third is earn. Last third of your life is give, right? So if you’re
under 35, you know, even 40, like you should be prioritizing. Am I learning? Am I, am I growing my skillset? Am I
meeting awesome people? And then, you know, once you have that skill set, then you’re in the earn phase. But if
you’re trying to prioritize, like I’m going to move jobs because it’s another 5 or 10k and you know, earnings or you
Meeting Title: EP 5_ What to do if most of your net
worth is in p…
Meeting created at: 22nd Apr, 2026 – 11:49 AM
20 / 22
know, that’s just, that’s, it’s very short sighted. Like you need to, I really like.
Speaker 3 – 48:25
That, that this third, third. That’s awesome. Weston, any closing thoughts? We appreciate your time and your
expertise that. Yeah. Any closing thoughts for the audience?
Speaker 1 – 48:35
The mental burden that we touched on earlier is the biggest piece. So you just have to shift your mindset. You have
to have like kind of opposing, you know, thoughts at the same time, which is like, this is going to work, but also like
I’m having fun along the way and it doesn’t really matter what the outcome is. If you can. If you can. It’s a. It’s a
little bit of a paradox. But if you can think both those things at the same time, that, hey, this doesn’t really matter
how this plays out. I’m having fun, I’m learning. And then also. But like this. But this is going to work. Like, I think
that’s a really great place to be.
Speaker 1 – 49:01
If you, if you have in your head that, like, I’m not going to be happy or, you know, content until this works, I think it’s
going to be a miserable ride and you also risk, you know, feeling like a total failure. So I think you really have to
strike that balance and just view it as a journey and you’re having fun. And again, I would really recommend you, if
you get into that community, talk to some of these people. Everyone you talk to who’s gone through an exit, they
miss the good old days. Like, they’re not. They’re not as happy as you think. I’m sure they went and had a couple
great vacations and drank a couple margaritas, but life is not all rainbows and sunshine.
Speaker 1 – 49:31
So I think you have to really appreciate the journey you’re on and just have fun along the way because you’re. You
will be miserable and it’s not going to be what you. What you think it’s going to be.
Speaker 3 – 49:38
When you have the exit, no question. Well, thank you, Weston and Jameson, for joining. And for those of you that
weren’t familiar with Closing Lock, they’re on all, you know, social media platforms. They’ve got an awesome
website. Definitely check them out. Very exciting. They’ve done a good job of documenting their journey and are
very transparent of, you know, how they’re growing and how the team’s growing and clients and stuff like that. So
really cool to follow. So definitely check that out if you have the time. So thank you, Weston.
Speaker 1 – 50:04
Meeting Title: EP 5_ What to do if most of your net
worth is in p…
Meeting created at: 22nd Apr, 2026 – 11:49 AM
21 / 22
Appreciate it. Thank you both.
Speaker 3 – 50:05
Thank you, Matt.
Speaker 1 – 50:06
Thank you, Jamison. Really fun conversation.

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