Macro Investing for Smart Wealth: AI + Risk Parity | Dan Pascone with Joseph Gradante | Podcast #25

In this episode: Dan talks with Joseph Gradante, co-founder and CEO of Alio Capital, about using AI-powered macro strategies and risk-parity style portfolios (inspired by Ray Dalio’s “All Weather” concepts) to bring institutional-style investing to everyday investors. They cover why traditional 60/40 portfolios struggle in today’s geopolitical and macro-driven world, how Alio’s “behavior-led UX” teaches people to build smarter portfolios in minutes, and why fintech 2.0 plus better regulation and technology are reshaping how regular people can invest.

Who this is for: Busy professionals who want smarter, macro-aware portfolios without day trading; “failed traders” who are tired of losing money on trading apps; and anyone curious about how AI, top-down investing, and better UX can help them build more resilient wealth over the long term.

• Alio Capital brings institutional-style macro investing to retail. They use their patent-pending Altitude AI to build portfolios that look more like what big institutions use (risk-parity / all-weather style) instead of simple stock bond mixes.
• Two paths for investors:

  • “Do it for me” answer a few questions and let Alio manage a macro portfolio on autopilot.
  • “Teach me as I go” build your own top-down portfolio in minutes with guardrails, learning macro concepts through the UX.


• Behavior-led UX teaches by doing. Instead of reading dense macro books, users learn through the interface: choosing asset classes, sectors, regions, and industries in a logical top-down flow and seeing how that shapes their portfolio.


• Top-down vs. bottom-up. Classic Graham-style fundamental analysis (bottom-up stock picking) is different from macro (top-down) investing. Joseph argues most people should start with asset classes, sectors, and diversification before ever picking individual stocks or options.


• Guardrails are built in. The app won’t let you build a “portfolio” with only one or two positions. It forces a minimum number of holdings and checks them against your risk profile so you can’t accidentally take on extreme risk that doesn’t match your answers.


• Ideal users fall into two main camps:

  • “Failed traders” who’ve tried Robinhood/Webull-style apps, have some market interest, but keep losing money and now want something sustainable.
  • Busy high earners (tech, lawyers, doctors, etc.) who want cutting-edge tech and institutional-quality thinking managing their money without having to do the work themselves.


• Fintech 2.0 is finally here. Joseph sees a new wave of fintech driven by friendlier regulation, deregulation in key areas, crypto focus, and more supportive policy. He argues finance has lagged other industries in tech adoption, but that’s changing quickly.


• Macro investing as a response to systemic risk. With high debt levels, inflation risk, and recurring crises every decade or so, Joseph believes macro-aware portfolios are essential, e.g., questioning whether a classic 60/40 with heavy bonds still makes sense.


• Alio is more about process than product. Instead of just offering the same ETFs as everyone else, they focus on a different way to build and allocate, top-down, risk-aware, AI-supported, designed to avoid the “dumb tail end” of trades that retail often gets stuck with.


• Joseph’s background shaped his worldview. Growing up in Manhattan, seeing 9/11, graduating into the Great Recession, and watching fintech emerge all led him towards building Alio, especially after COVID, money printing, and new macro books highlighted big structural shifts.

• 00:02 – Intro to the show and mission: helping business leaders make smart, confident money decisions.
• 00:27 – Dan introduces the episode and guest Joseph Gradante, co-founder and CEO of Alio Capital.
• 01:16 – Joseph explains Alio’s core idea: using AI to power macro portfolios and bringing institutional-style risk parity/all-weather investing to retail.
• 01:48 – Why geopolitics matter as much as fundamentals now, and why macro is the right lens for this environment.
• 02:09 – Two main user paths in Alio: fully managed vs. build-it-yourself with guidance.
• 02:48 – The “failed trader” problem: trading apps have huge user bases but most users lose money; Alio aims to give them a more robust, top-down framework.
• 03:27 – “Behavior-led UX”: users learn macro by doing, choosing assets by category (asset class, sector, geography, etc.) like a guided buffet.
• 03:56 – Top-down vs. bottom-up: why most people should learn to pick sectors and asset classes before individual stock picking or options.
• 05:11 – Two ideal profiles: failed traders looking for something sustainable and busy pros who want better tech & macro thinking managing their wealth.
• 06:22 – Why older mean-variance models (like 1990s-style portfolio optimization) are like putting a decades-old engine in a modern car.
• 06:51 – The app experience: mobile, questions-based onboarding, and routing users to either managed or DIY macro portfolios.
• 07:18 – Example of the guardrails: the app won’t let you build a two-asset “portfolio” or take on risk inconsistent with your answers.
• 08:12 – Joseph’s view on “Fintech 2.0,” regulation, crypto policy, and why he thinks the current environment is favorable for financial innovation.
• 10:06 – Macro vs 60/40: questioning heavy bond allocations in a world of high debt, currency risk, and inflation.
• 11:31 – Joseph’s backstory: Manhattan, 9/11, Great Recession, and seeing traditional finance shrink while fintech emerged.
• 12:19 – Watching fintech grow as mostly nice UX, not deep investment substance, and why he wanted to bring more gravitas.
• 13:06 – COVID and massive money printing as the final push to build an AI-driven macro solution for regular investors.
• 14:03 – Joseph describes his team: CTO, UX lead, AI lead, and a recent hire from Citadel.
• 14:42 – Where to find Alio: website and app stores.
• 14:56 – Lightning round: coffee, chicken parm, AirPods, Ray Dalio quote, favorite book (Zero to One), and personal hacks.
• 16:09 – How Joseph uses ChatGPT day-to-day (including as a second pair of eyes on written messages).
• 16:28 – Bucket list: skiing black diamonds in the Cascades and why he moved to the Pacific Northwest.
• 17:07 – Current milestone: raising Alio’s Series A round.
• 17:26 – Advice to his younger self: don’t obsess over elite school pedigrees, leverage the tools and information on the web and focus on what you do afterward.
• 17:50 – Dan closes the episode and reminds listeners to prioritize their version of a rich life.

In this episode of Making Sense of Your Money, Dan sits down with Joseph Gradante, co-founder and CEO of Alio Capital, to talk about how macro investing and AI can help everyday investors build smarter, more resilient portfolios. Joseph explains that Alio uses its patent-pending Altitude AI to implement macro strategies similar in spirit to Ray Dalio’s “All Weather” and risk-parity approaches, ideas that are widespread among institutions but rarely accessible in a user-friendly way to retail investors.

Alio is designed around two main user journeys. For busy professionals who don’t want to manage portfolios themselves, Alio offers a fully managed option: answer a short set of questions and let the team’s macro engine handle the rest. For those who want more control but are tired of losing money on trading apps, the platform enables users to build their own top-down portfolios in just a few minutes, guided by guardrails and AI.

Joseph introduces the concept of “behavior-led UX,” an interface that teaches macro investing while users interact with it. Instead of reading dense books on macro, users select asset classes, sectors, geographies, and industries step by step. The app enforces basic diversification (e.g., a minimum number of holdings) and cross-checks choices against the user’s risk profile, preventing them from building overly concentrated or misaligned portfolios.

The conversation walks through why macro investing and risk-parity concepts matter more in today’s world. Joseph argues that recurring systemic shocks, 9/11, the Great Recession, COVID, and large-scale money printing, plus high debt levels and inflation risk make it dangerous to rely solely on traditional 60/40 stock-bond portfolios. Geopolitics and macro factors have become as important as corporate fundamentals. By starting with asset allocation and risk management, Joseph believes investors can create strategies that better withstand volatility.

Dan and Joseph also talk about “fintech 2.0.” Joseph describes how fintech’s first wave brought improved UX and access but lacked deep portfolio substance. Now, he sees a more supportive regulatory environment for innovation, especially around crypto and financial technology. He believes finance has lagged other industries in adopting modern tech but is poised for a catch-up phase where AI and better design can close the gap between institutional and retail investing.

Joseph’s own background, growing up in Manhattan, seeing 9/11, graduating into the Great Recession, working in traditional finance at firms like Merrill, and then transitioning to the West Coast and tech, shaped his conviction that macro, AI, and better UX could help regular investors navigate a more complex world. He credits books like Piketty’s Capital in the Twenty-First Century and Ray Dalio’s work on changing world orders for influencing his thinking.

The episode wraps up with a lightning round where Joseph shares his love of coffee, chicken parm, AirPods, Ray Dalio’s quote about simplicity, and Peter Thiel’s Zero to One. His personal hack: always run messages through ChatGPT to clean them up before sending. For a current milestone, he’s focused on raising Alio’s Series A. His advice to his younger self, and to listeners, is not to obsess over elite credentials but to leverage the tools and information available online, because “the world and the web are your oyster” if you use them well.

Transcript edited and condensed for clarity and flow.

Narrator: 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 make smart, confident money decisions.

Dan: I’m your host, Dan, founder and CEO of Tailored Wealth. Each episode we bring on a trusted voice in the financial world, someone who works with high-level professionals to simplify the complex and turn strategy into action.

Dan: Today I’m excited to welcome Joseph Gradante, co-founder and CEO of Alio Capital. His firm is doing some really interesting work in the macro investing space. Joseph, thanks for joining us, I’m pumped to have you today.

Joseph: Happy to be here, Dan. Thanks for having me.

Dan: We’ve got a lot to cover and I know our audience wants your perspective on a bunch of topics. Let’s jump in. Give us a high-level overview of what Alio does, and a little bit about your background and how you ended up here.

Joseph: Absolutely. At Alio, we use AI, specifically our patent-pending Altitude AI, to power macro portfolios. The idea is to bring something that’s standard on the institutional side to everyday investors. Think of strategies pioneered by people like Ray Dalio, risk parity and all-weather style portfolios.

Joseph: You can either let our team manage everything for you if you’re not interested in the details, or you can learn to build a macro portfolio yourself in under 90 seconds. In the environment we’re in, where geopolitics can influence returns as much as fundamentals, I think macro is the only way that really makes sense.

Dan: So if I’m an average investor coming to Alio, what’s the experience like?

Joseph: There are two main paths. Path one is for people who are busy and don’t want to learn investing in-depth. They just want a professional solution. You answer a brief set of questions and you’re basically done in under 30 seconds if you move quickly. We handle the rest.

Joseph: Path two is for people who want some control and don’t want to pay asset management fees but have struggled with trading. If you look at the space, trading apps have big user bases but over 90% of users lose money. We built a path for people who have tried those apps, learned a bit, realized it’s not working, and now want a structured, long-term approach.

Joseph: On that second path, you can build custom, top-down portfolios, selecting negatively correlated assets, in just a couple of minutes. The interface is set up like a guided buffet. We call it “behavior-led UX.” It’s organized by asset class, sector, industry, and geography. You move through those choices and a portfolio gets constructed in minutes that you can then manage passively and still aim for alpha.

Dan: “Behavior-led UX” is a cool term. What does that mean in practice for the average investor?

Joseph: There’s an ed-tech element. There are a lot of macro books out there, but most people don’t have time to read them cover to cover. Instead, we let them learn by doing. When they build a portfolio in our app, they’re learning what top-down investing looks like choosing asset classes, then sectors, then industries and regions.

Joseph: In finance, there’s the bottom-up approach, Benjamin Graham-style fundamental stock picking, and then there’s the top-down approach, which leans more on macro, geopolitics, and technicals. For most people, it’s much easier to start from the top-down view, think about asset allocation and diversification first. If you can’t pick asset classes or sectors, you’re not ready to pick individual stocks.

Joseph: Once you understand sectors, then you can drill into individual equities and, eventually, options. But most people do the reverse, they start with options or meme stocks, and that’s why so many fail.

Dan: That resonates. People start at the end instead of the beginning.

Dan: Let’s talk about your ideal clients. You’ve described two profiles, set it and forget it, and the more hands-on investor. Walk us through those archetypes a bit more.

Joseph: Sure. Without diving into detailed personas, one big group we see is what I’d call “failed traders.” They’ve used Robinhood, Webull, a bunch of different trading apps. They care about the markets, maybe follow them closely, have four or five finance apps on their phone, but the results haven’t been good. They’ve realized pure trading isn’t working and are now looking for something that can actually get them to their goals.

Joseph: That’s where the custom macro path fits: it lets them build better-structured portfolios with support and guardrails.

Joseph: The second group is busy professionals, tech folks, lawyers, doctors, who don’t want to spend their time managing portfolios but also realize that many robo-advisors aren’t generating a lot of alpha. Most robo platforms don’t use truly modern tech under the hood. A lot of them are still driven by old-school mean-variance optimization, a kind of regression analysis that’s been around for decades.

Joseph: It’s like putting a 1990s engine in a brand-new sports car. Would you want a ’90s engine in your car? Probably not. So why would you want that powering your money? Those professionals prefer cutting-edge technology and institutional-quality thinking, which is what we’re trying to deliver with the managed path.

Dan: Is Alio purely app-based? And are the actual investment options similar to what other platforms offer, or different under the hood?

Joseph: It’s a mobile app, and the experience is tailored based on how you answer the onboarding questions. If your answers suggest you’re a managed client, we emphasize that path. If you fit the DIY macro learner profile, we highlight that instead. You can still choose, but we guide you.

Joseph: One of the things that sets us apart is how the UX and AI work together. For example, if you try to build a “portfolio” with just two ETFs, the app won’t allow it. Based on your risk profile, it knows that’s not diversified enough. We require a minimum number of holdings so people experience what a proper portfolio feels like.

Joseph: The AI also evaluates whether chosen assets are consistent with your stated risk tolerance. If they’re not, it will flag that and stop you from building something misaligned.

Joseph: Over a multi-decade investing horizon, avoiding big mistakes and excessive fees can make a huge difference. If you can take a little time to learn the process, you might avoid paying asset management fees that could eat away a quarter or more of your long-term compounded returns.

Dan: That makes sense.

Dan: Where do you see this industry going? What’s the future of fintech and platforms like yours, and how do they change investing for the average person?

Joseph: I’d call this “fintech 2.0.” When I first got into fintech, everyone was talking about the next wave, but then we had a long risk-off period, tight regulation, and not much M&A or innovation.

Joseph: Recently, policy shifts, things like deregulation in some areas, new crypto frameworks, and a more open stance toward fintech, have started to change that. We’re seeing new laws and guidance that are more supportive. That opens the door for more aggressive innovation in financial services.

Joseph: If you think about it, tech has transformed almost every other industry. Finance has been relatively slow, especially in things like cross-border payments and legacy banking systems. There’s a lot of room to modernize.

Joseph: At the same time, we’re dealing with big macro issues: high government debt, inflation concerns, monetary system questions. I think fintech especially macro-focused solutions like ours, can offer a better way to navigate those challenges.

Dan: When people go through your UX and questionnaire, are they just being steered to the same ETFs and assets as everywhere else, or is there something fundamentally different in what they own?

Joseph: It’s less about offering exotic products and more about a superior process. There’s an idea called the “odd-lot theory,” which basically says that retail investors are often on the wrong side of the trade, the last ones in after institutions have moved.

Joseph: We want to invert that by focusing on macro and top-down allocation first. Instead of defaulting to a 60/40 portfolio with 40% in bonds in an environment of high debt and potential currency/inflation issues, we ask: what mix of asset classes makes sense given the macro backdrop?

Joseph: Our approach is very common on the institutional side, macro, risk parity, diversified risk exposures, but we’re using Altitude AI and behavior-led UX to bring that to individuals. So yes, we might use familiar ETFs and instruments, but the way we allocate and manage risk is different.

Joseph: Our mission is to innovate at multiple levels: the process (macro, top-down), the tech (AI instead of only old-school optimizers), and the UX (teaching people how to build and understand portfolios instead of just dumping a list of tickers in front of them).

Dan: Love it. Let’s talk about you for a second. What’s your background, and how did it lead you to starting Alio?

Joseph: I grew up in Manhattan and saw 9/11 firsthand. I had family who worked at Cantor Fitzgerald. Later I interned there. Those events left a mark.

Joseph: I graduated college during the Great Recession, which was another huge shock. It felt like every 10 years there was some kind of systemic black swan event that shook the financial system.

Joseph: I went into traditional finance and spent time at places like Merrill. I remember management talking about how they could retain grandparents and parents as clients but were having trouble connecting with younger generations, there was a big trust and cultural gap.

Joseph: Around that time, fintech started emerging. I saw these new apps expanding access and improving UX, which was exciting. But when I dug deeper, a lot of it was surface-level, beautiful interfaces with less depth in risk management and portfolio construction.

Joseph: I kept an eye on it, did market research, and started learning to code. Eventually, I moved to the West Coast and got closer to tech. Then COVID hit. The scale of money printing, economic disruption, and social tension was a wake-up call.

Joseph: Around the same time, books like Piketty’s Capital in the Twenty-First Century and Ray Dalio’s work on changing world orders were getting a lot of attention. Even political movements across the spectrum, though very different, were all in their own way pointing at the same underlying economic stresses.

Joseph: I came to the conclusion that macro investing is a key part of dealing with this fourth turning-type environment. That’s what made me passionate about building a product that gives regular investors better tools to navigate macro forces.

Dan: How long has Alio been around, and tell us a bit about the team and how people can find you.

Joseph: The team is incredible. Our CTO, Chris, brings a huge amount of technical experience. Benjamin leads the behavior-led UX we’ve talked about he’s responsible for making the app feel intuitive. Adam is behind the Altitude AI technology that drives our macro engine. And we recently brought on Nico, who came over from Citadel.

Joseph: People can find us at aliocap.com, and in the Apple and Google app stores. Just search for “Alio Capital.”

Dan: Awesome. Thanks for that background, Joseph.

Dan: We’re going to shift gears now into one of my favorite segments: the lightning round. We don’t tell guests about this ahead of time, we want it real and off the cuff.

Dan: I’ll ask a question, you give the first thing that comes to mind, one word or a longer thought, up to you. Ready?

Joseph: Ready.

Dan: Coffee or tea?

Joseph: Coffee.

Dan: One meal for the rest of your life, what are you picking?

Joseph: Chicken parm.

Dan: Nice. Now I’m hungry. What’s one tool or piece of technology, besides your phone or computer, that you can’t live without?

Joseph: AirPods.

Dan: Good one. Do you have a favorite quote or phrase about money or success?

Joseph: One from Ray Dalio sticks with me “Any fool can make things complex; it takes a genius to make things simple.” That’s what we’re trying to do with macro investing, make it accessible and simple without dumbing it down.

Dan: Love that. How about a favorite book on business or finance?

Joseph: For pure business and not economics, I’d say Zero to One by Peter Thiel.

Dan: Do you have a personal hack you can share?

Joseph: ChatGPT. Don’t send out an important message without running it through ChatGPT first. Take the extra 30 seconds. When I don’t, there are usually typos. Time is valuable, but that small step can make your communication much sharper.

Dan: Love that. What’s one bucket-list item you’ve already checked off?

Joseph: Skiing black-diamond runs in the Cascades. I grew up in Manhattan but I love skiing, that’s a big reason I moved to the West Coast.

Dan: Very cool. What’s one financial milestone you’re working toward right now, personally or for the business?

Joseph: Raising our Series A round.

Dan: Best of luck with that. Last lightning question, if you could give one piece of advice to your younger self, what would it be?

Joseph: I’d tell myself not to obsess over traditional education and brand names. I used to beat myself up for not going to certain schools. Now I realize it’s what you do afterward that really matters.

Joseph: There are incredible tools and information available online. If you make good use of them, the world, and especially the web, is your oyster.

Dan: Well said. I might borrow that line.

Dan: Joseph, this has been great. Thanks for sharing your story and giving us a look into Alio Capital. For listeners, if you want to learn more, check out Alio online and connect with Joseph on LinkedIn.

Dan: That’s it for today’s episode. As always, keep prioritizing your version of a rich life.

• Watch this episode on YouTube
• Alio Capital – Official Website
• Connect with Joseph Gradante on LinkedIn
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If this episode got you thinking about your own portfolio, here are two simple moves you can make:

• 1. Audit your current allocation. Look at your real asset mix (not just what you think it is). How much is in equities, bonds, cash, alternatives? Does it line up with your risk tolerance and time horizon in today’s macro environment?
• 2. Learn one macro concept and apply it. For example, research “risk parity” or “all-weather portfolio” and ask your advisor how those ideas might (or might not) fit your situation. Even a small tweak in how you diversify risk can have a big long-term impact.