The Billion-Dollar Advantage of Cross-Border Capital | Dan Pascone with Aditya Sahai | Ep #17 Unlisted

Aditya Sahai is the managing partner at Silvermile Capital. He says he started in public markets at a young age, later ran long-short equities and derivatives strategies on behalf of family offices, and completed a master's degree along the way. While doing that, he says, he met people who pointed to an emerging opportunity in private technology companies. He started Silvermile "on the back of COVID" as a firm focused on cross-border transactions.

By his account, Silvermile works on private-market transactions in fintech, software and AI, mostly with emerging growth and middle-market companies that are venture- or sponsor-driven. He says target deal sizes are $20–$200 million and that the firm has transacted over $3 billion in financing across 4 years of operations. He also says its capital partners include sovereigns, pensions and direct growth equity and venture investors. [VERIFY: guest figures about his own firm] Dan noted that he shares a public-markets background and that Tailored Wealth has been creating more content on private markets recently.

Aditya says cross-border transactions are "a harder nut to crack" because due diligence and educating the counterparties take more effort. His view is that the payoff can be better economics and, in many cases, better partners, especially for companies that trade and transact globally. He says Silvermile works with a network of capital partners he describes as some of the top allocators to alternatives, and uses its deal-flow networks to find companies, help underwrite them and monitor them over time. [VERIFY: guest claim]

He says most of the firm's activity falls in 3 markets: North America, which is its core market for capital partners, Europe, and Asia, where he says most of the companies he works with are located, along with its sovereign partners. When Dan asked about the biggest challenges, he named 3:

• Regulation: Understanding the law of the land and the regulatory regime in each place, which he says is changing faster than ever.
• Due diligence: It gets more complex and takes longer when it crosses borders.
• Pace: Technology markets move fast and are competitive, so his team has to keep updating its understanding of business models and the competitive picture. He says the extra effort is worth it for the opportunities it opens up.

Aditya says sourcing comes from 2 places: warm introductions from existing backers, which can be individuals, institutions and sometimes families, and events, conferences and outreach campaigns based on his team's own analysis. Communication, he says, is a mix of in-person meetings, events and modern communication tools.

When he evaluates a company, he says he starts with the founder's "why." He asks whether there's a personal pain point or a gap in the market, whether the founder has an unfair advantage (maybe not yet, maybe in the future) and what will keep them going when things don't go their way. He also looks at life events that may have pushed someone to tap into extra potential. He says there have been companies with imperfect decks and metrics that his team pursued anyway because of how the founders articulated their ambition and passion.

Dan reflected that this works like a "resiliency metric," and said that in his experience as an entrepreneur, a person's life story can be a good indicator of how they'll handle the ups and downs.

Asked how the industry may evolve over the next 5–10 years, Aditya says technology is shortening timelines and raising output. He says it also offers new ways to position deals, find counterparties and resolve questions that come up in diligence. But he describes it as "still a hybrid world": people have to monitor what the technology produces and feed back into it.

He says his firm will keep relying on warm networks and hard-won relationships for origination, and expects technology to help more with later steps like analysis and benchmarking.

• Coffee or tea: Coffee.
• Cats or dogs: Dogs.
• Technology he can't live without: His car. Dan guessed a Tesla, and Aditya confirmed.
• Favorite quote or phrase: The power of compounding. Dan added the "eighth wonder of the world" line, which is often attributed to Einstein, though the origin is unverified. [VERIFY]
• Favorite book: Reminiscences of a Stock Operator.
• Personal hack: Watching Rocky Balboa movies to get into deep hard work mode.
• Bucket list item accomplished: Visiting 40 countries in the last 3 years, with Scotland standing out.
• Current milestone: Reaching a certain level of monthly net profits for his firm.
• Advice to his younger self: Focus on the people you spend time with and how you add value to them and gain value from them.

• This is largely an institutional market: The deals Aditya describes, at $20–$200 million with sovereigns and pensions as partners, aren't where most individuals invest. An executive usually reaches private markets, if at all, through a fund or platform, often limited to accredited investors and often with minimums, fees and lockups. Our post on private equity and alternative investments covers the trade-offs, and the SEC's investor bulletin on private placements under Regulation D explains how these offerings work.

• A strong story isn't a result: Weighing founder resilience is reasonable, but it's hard to measure and it doesn't guarantee an outcome. Early-stage companies can and do fail, and investors can lose everything they put in.

• Cross-border adds layers of risk: Currency swings, different legal and regulatory regimes and different disclosure standards can all matter. Private company valuations are estimates, not market prices.

• Compounding cuts both ways: Compounding was Aditya's favorite money idea. Fees, taxes and losses compound too, and a long lockup means you can't move the money elsewhere if your plans change.

This hypothetical is for illustration only. All figures are assumed, aren't projections or recommendations, and ignore fees, taxes and timing of capital calls.

Assume an executive with $600,000 in household income and $2,000,000 in investable assets is invited to invest in a private technology fund that holds companies in several countries.

• Option A, a $100,000 commitment (5%): If the investment loses 40%, the loss is $40,000, or 2% of the $2,000,000 portfolio.
• Option B, a $500,000 commitment (25%): The same 40% loss is $200,000, or 10% of the portfolio, and $500,000 could be tied up for 10+ years.
• Currency: If a $100,000 position is denominated in a foreign currency that weakens 10% against the dollar, that's $10,000 less in dollar terms before any investment result.

The 40% decline is an assumption chosen to show how size changes the stakes, not a forecast. The same investment can be a small bet or a plan-defining one depending on how much you commit.

We use Life-Driven Planning, a 6-phase plan covering Cash Flow, Retirement & Hybrid Retirement, Risk, Expense & Goal, Tax and Legacy. A private investment touches several of those phases: your cash flow, your risk, your tax picture and how flexible you want your later career years to be. Our post onAnnouncer: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life. Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions. Welcome to another episode of the Making Sense of Your Money podcast. Dan: This is episode number 17. I'm your host Dan, founder and CEO of Tailored Wealth. And each episode features a trusted voice in the financial world, someone who works directly with high-level professionals to simplify the complex and turn strategy into action. Dan: And today I'm excited to introduce our special guest, which is Aditya, who is the managing partner at Silvermile Capital. Dan: And he and his firm have great expertise and a really strong background in M&A work and capital raises. And I'm excited to have you. So, Aditya, thanks so much for joining me on the Making Sense of Your Money podcast. Good to have you today. Aditya: Thanks for having me here and look forward to the conversation, Dan. Dan: Yeah, likewise. Likewise. Dan: So, I know there's a lot that our audience is going to want to hear from you, especially given your unique expertise. So, let's start off, if you could just give like a 90-second overview of what you and your firm do, how you got into the space, and the types of folks that you work with. Aditya: Absolutely. So, you know, we do mostly cross-border transactions within private markets with a deep focus on technology companies, specifically fintech, software, AI. Aditya: We play in the emerging growth and the middle market layers, typically venture- and sponsor-driven companies. We typically target deal sizes between 20 to 200 million. We've transacted over 3 billion in financing so far across four years that we've been operational. Aditya: And what got us into this was largely a focus and an interest in how capital works for innovation and specifically how cross-border capital movements can have, you know, large outcomes with ambitious founders. So that's what got us going. Aditya: Right now, we work with a variety of capital partners including sovereigns, pensions and, you know, direct investors on the growth equity as well as the venture side and work very closely with a great set of founders who are building very cool stuff and, you know, us having a direct kind of seat alongside them in terms of their rocket ship just makes us very excited about the kind of work we do. Dan: Very, very cool. Yeah, that's very cool. There's obviously a big market for what you do now. Dan: How did you get into the business to start? Let's talk a little bit there. How did you get into this space to begin with? Aditya: Right. So, you know, my background is I was originally in public markets and it kind of started off pretty young. So, I was doing that for a number of years. Aditya: That eventually evolved into doing it on behalf of certain family, you know, family offices. So, we were doing long-short equities, derivatives, that kind of thing. I had a good enough outcome there, did my masters, and, you know, while I was doing that I came across a number of interesting folks who talked about this emerging opportunity within private markets, specifically tech companies. Aditya: So, it was their foresight that I kind of thought that there's something in it really and decided to take the plunge and, you know, it was just on the back of COVID that, you know, we decided to start up Silvermile Capital as a firm focused on cross-border transactions. So that's what got me into it. Aditya: You know, things kept happening, people we met, different kinds of folks, and eventually landed up some interesting transactions mostly in the software and the tech-enabled platform side, and that gave us enough conviction that there's a lot of, I guess, you know, depth in this market for us to carve a niche and that's where we are, you know, that's our origin story here. Dan: Very cool. Very cool. Thank you for sharing that. Dan: So my audience knows this because I talk a lot about private markets. We've been doing a lot of content on private markets recently. So, it's well timed that we have you on the show and I too have a background in public markets and while we sort of diversify with our clients and do a little bit of everything, we've been very, very keen on private markets as of late. Dan: So, you've mentioned cross-border transactions. I want you to educate us a little bit on what that means and what's the value there. Aditya: Absolutely. Okay. So look, I mean cross-border transactions in itself are a harder nut to crack and, you know, logically speaking it's because due diligence, the ability to educate the counterparties and all of that. It's just, the bar is a bit higher. Aditya: But it all makes sense because your optionality and your, you know, ability to drive better economics as well as in many cases better partners kind of increases. This is very true for companies that trade globally, transact globally and have avenues to, you know, access global markets. Aditya: The way we kind of go about this is, you know, we have this wide rolodex of capital partners which is described as being some of the top allocators to alternatives. So what we do is, you know, when there's a deal to happen in terms of, you know, any asset class or let's just say any category that they're interested in and they're looking at some of the best companies or category-defining companies, then we go out there, leverage our, you know, deep access and proprietary deal flow networks to find them relevant stuff and help them underwrite those companies, you know, find the best way in and then kind of work, monitor, and grow those, you know, opportunities into outlier events. Aditya: That's the ambition, that's the way we kind of go about these. Aditya: Most of our stuff typically happens within three broad markets. So that's obviously North America, which is our core market for capital partners, alongside, you know, Europe, and most of the companies I work with also happen to be in Asia along with our sovereign partners. Aditya: So it's a great combination we've managed to ramp up over the years in terms of transacting across the pond in Europe, North America as well as in Asia. Dan: Yeah, that makes a lot of sense. I could see where your expertise and value lays there. Dan: What are some of the biggest challenges that you see, Aditya, when it comes to cross-border transactions? Aditya: I think the first thing would be just the understanding of the law of the land and the regulatory regime. So that's number one. How do you navigate those? The world's changing faster than it was, you know, ever before. So that is one of the main things. Aditya: The second thing is, you know, you have a whole host of due diligence. It just gets a little more complex and elongated when you're doing it more on a cross-border side. So that's second. Aditya: As fast-paced a market as technology is and, you know, just the level of competition that you see in these markets, you have to be, you know, constantly at it in terms of how much you understand businesses, business models, the changing competitive environment and that kind of thing. So it needs a lot more effort, but I think all of that is worth it in the end in terms of the outcome and the opportunities that you can access and harness. Aditya: So I think those are the most challenging parts of our work as well as the most exciting parts of our work. And as you can imagine, you know, because you need to keep track of different jurisdictions and deal activity and momentum and stuff like that, you know, the onus is on us to be constantly on our feet in terms of, you know, making sure that we're well informed, you know, we're data-driven and we're keeping our network up to date and it's working for us as well as for who we kind of transact and work with. Dan: Yeah. So, I know your space relatively well and I know there's a lot of moving parts when it comes to deals like this. Dan: Tell us a little bit about what you do, what you look for in deals, how you source them, and then talk a little bit about like the communication workflows that you have, because there are a lot of different parties involved obviously, right? Aditya: So I think, you know, our sourcing is predominantly twofold. We either rely on closed warm intros which can come from a subset of existing backers. Those could be individuals, institutions, sometimes even families. So that's the important part. Aditya: The second would be, you know, any kind of events, conferences, as well as outreach campaigns that we might do based on our judgment and analysis. So that's typically how top of the funnel works for us. Aditya: In terms of communication, again, you know, it's a combination of in-person meetings, you know, events, as well as some of these modern communication tools for, you know, engaging with different sets of people. Aditya: I think what we're very interested in is just looking at the why, you know, why someone started it out. Is there a personal pain? Is there something they've identified which acts as a big gap in the market, etc., as well as, you know, is there any unfair advantage, maybe not now, maybe in the future, which those guys might have which will, you know, because in any case there's things that fall apart, there's things that don't go your way. So what will keep you ticking in those times when there's uncertainty? So what gives, you know, power to your resilience? Aditya: And I think I also look at, you know, has there been any event in your life which just makes you tap into that, you know, extra potential that every human has. So that's something that I, that's why I kind of look at your personal story as well very closely, someone who's kind of starting it out, you know, doing this. Aditya: So those are important things that I kind of look for, you know. In many cases there have been companies whose decks haven't been perfect, whose metrics haven't been perfect, but it's just, you know, something about them in terms of how they articulate or, you know, their ambition and passion that kind of speak for itself which makes us say, okay, there's something in it, that's something that the market and the public will see eventually, and I think that's something we should go after. Aditya: So we do, you know, have a lot of those instances where we believe that there's, you know, someone who's identified a trend ahead of time or there's, you know, a certain way a market could potentially evolve and how do we bring those ideas and opportunities to our, you know, captive institutional client base. Aditya: So those are some of the reasons why, you know, people stick with us and look at us for bringing them some interesting innovative ideas that can fetch, you know, some interesting outcomes. Dan: Yeah, that's very cool. Dan: Well, I love what you said there about sort of digging even beyond the metrics and beyond the pitch deck to sort of understand the founder, the team, the why. And then, you know, what I heard you say was, you know, evaluating their resiliency factor, right? If you almost had like a resiliency metric that you could evaluate, because any of us that have been entrepreneurs know that that is absolutely critical and, you know, sort of your life story helps to frame that and is a pretty good indicator in my experience of, you know, how you will perform across ups and downs which, you know, if you are an entrepreneur for long enough you will certainly have many of both. Dan: So I thought that was really, really insightful and I appreciate you sharing that. Dan: Aditya, tell us a little bit about where you see your industry going. Obviously, there's so much that's happening right now relative to technology and AI and you're investing in a lot of that, but tell us a little bit about your industry and how you see it evolving over the next 5 to 10 years. Aditya: I think technology is taking over a lot of the things that we used to do. So, timelines are getting cut. I think output is more or less, you know, getting ramped up. Aditya: We're also seeing different ways of making a deal happen by way of, you know, interesting ways of positioning or finding counterparties to work with as well as just, you know, resolving any queries that eventually turn up in the diligence phase. Aditya: So there's different interventions that technology, you know, finds its applications across the deal lifecycle which I think for most parts is just, you know, making it more efficient and making it more worthwhile for folks like us to, you know, focus on getting the job done, which is interesting. Aditya: I think the onus is still on the human side to make sure that technology is giving what you need and how you want it to work as well as any evolution loops and feedback cycles that it goes through has to again pass through to a human, you know, kind of monitoring it. So it's still a hybrid world that we see with growing applications and we'll continue to use different technologies as they get developed or as they kind of make themselves available to us for our, you know, deal making while still focusing on the fundamentals. Aditya: You know, because we will not rely on origination for, you know, technology to do anything of that. We will still focus on our warm networks and, you know, the hard work we've put in to build those channels out but maybe, you know, steps that follow, whether it's analysis or benchmarking and some of those stuff, that's where technology will help us. Dan: Love it. Yep. Makes a lot of sense. Makes a lot of sense. Dan: All right. So we're going to switch gears now. We're going to focus a little bit on you and let the audience get to know you. So this is always a really fun part of the podcast. I call it the lightning round. Dan: I never tell guests about it ahead of time because we want it to be super organic and natural. I'm going to give you some questions and then all I ask is that you give us the first thought that comes to your mind. It could be a one-word answer. It could be, you know, a deeper explanation on it. You ready? Aditya: Sounds good. Dan: All right, let's do it. Coffee or tea? Aditya: Coffee. Dan: Cats or dogs? Aditya: Dogs. Dan: What's one tool or piece of technology, so it could be hardware or software, other than your computer or your phone that you can't live without? Aditya: Can I say my car? Dan: Yeah, sure. We can. Let me guess. You're a Tesla driver. Aditya: Yes. Dan: All right, we got it. Dan: Do you have a favorite quote or phrase about money or success? Aditya: I think it would have to be on compounding, the power of compounding. Dan: Yeah, compounding interest. Albert Einstein said it long ago. The eighth wonder of the world, right? Aditya: Mhm. Dan: Love it. All right. Dan: Do you have a favorite book on finance or business? Aditya: Yeah. There's one actually, Reminiscences of a Stock Operator, which is pretty good, you know, about a guy who kind of used instinct to, you know, trade stocks and stuff like that. That was interesting. Dan: Very cool. I like it. I like it. I'll have to check that one out. Dan: Do you have a personal hack that you could share with us? Aditya: Ability to, you know, get into, I guess, deep hard work mode by watching Rocky Balboa movies. Dan: Now you're speaking my language. All right. So, we're going to watch Rocky to get into deep hard work mode. I like that. I like that. Dan: Usually makes me want to like go run through a wall or work out, but I like that. That's a good one. Really good. I haven't heard that one before. That's good. It's good. Dan: What's one bucket list item that you've already accomplished? Aditya: You know, stepping into 40 countries in the last three years. Dan: Forty countries in three years. All right. Very cool. Anyone stick out for you? Aditya: I would say Scotland. Dan: Scotland. That's on my list, actually. Very cool. That's on my list. Dan: What's one business or financial milestone that you're working towards? Aditya: A certain echelon in terms of monthly, you know, net profits for our firm. Dan: Very cool. Very cool. Dan: And lastly, if you could give one piece of advice to your younger self, what would it be? Aditya: I would say focus a lot on the people who you spend time with and how you add value to them and gain value from them. That's the most important thing. Dan: Yeah, I love that. We're always trying to add and gain value from people around us and put more people around us that can add value and we can add value to. That's well said. Dan: All right. And Aditya, if our listeners want to connect with you, collaborate with you, potentially work with you, how and what's the best way to reach out to you? Aditya: I'm very active on LinkedIn and email. So, you know, you can find me on LinkedIn as well as my email, which is at silvermile.uk. Dan: Very cool. Very cool. We'll put that in the show notes. That's great. Dan: Well, listen Aditya, thanks for coming on. I really enjoyed the discussion. Thanks for your insights today and that's it for another episode. Dan: As always, keep your strategy sharp, your goals clear, and your money working as hard as you do. Cheers. Aditya: Thanks, Dan. Take care.Retirement explains the idea of stepping back gradually instead of all at once.

Life Driven Investing (LDI) builds a portfolio backward from your life using the Four Liquidity Bands: 0–2 years, 3–5 years, 6–10 years and 10+ years. Private, illiquid investments belong, if at all, in the 10+ year band, and money you need in the next 0–2 years shouldn't go there. Our video on how to invest for your life, not just returns walks through the framework. If you hold private-company equity or other awards, our Equity Compensation Playbook, a set of structured rules for RSUs, options, ESPPs and related tax issues, helps us plan around concentration before adding anything illiquid. Under our Quarterly Strategy Rhythm (ongoing plan updates, decision reviews and rebalancing), we revisit whether each position still fits. This episode is educational and isn't an endorsement of Silvermile Capital or any company, strategy or investment discussed.

This episode is for corporate executives and senior professionals in their 40s and 50s with $500k+ in household income and complex compensation who want to understand how private markets and cross-border deals work, and what questions to ask before putting money into anything illiquid.

If you're a high-earning executive weighing private investments against the rest of your plan, we'd be glad to talk it through. Book a free Wealth Strategy Call with us, and we'll look at your situation together.