Financial advice is highly attractive to career changers. September 27, 2026 PRESENTED BY Good morning and happy Sunday. Meaningful work and flexibility are among the top reasons people leave jobs for new careers in financial planning. But first, a word from our sponsor, Conquest . A man is only as good as his tools, they say. But plenty of advisors have been feeling short of a few lately, with 58% saying their financial planning technology is missing key features, functionality, or integrations, per Cerulli research. 1 If you’re an RIA, you’ve probably felt the pain this brings first-hand, as you spend hours building a financial plan from scratch for a client. With only so many hours in the day, you’re left having to choose and prioritize which households get your most in-depth work. While nobody is handing out more hours, Conquest has rebuilt the tooling for the tasks that are eating yours — and they’ve opened a waitlist for independent advisors to gain direct access. Strategic Advice Manager ® (SAM) , the firm’s verifiable AI engine, evaluates hundreds of strategies against a client’s actual situation and drafts a personalized plan in minutes, leaving you to then simply decide what to apply. Join the waitlist to try Conquest free for 14 days. FINANCIAL PLANNING The Outsiders: Why So Many Financial Planners Are in Their Second Careers Photo illustration by Connor Lin / The Daily Upside Emily Bandoni was teaching the Pythagorean theorem to a sophomore math class when a student asked her how the geometric principle would ever apply to real life. “I remember not having an answer,” she said. “That was definitely a moment for me of realizing that I maybe wanted to do something different that would be more helpful for a broader audience.” “Something different” turned out to be financial planning. After teaching high-school math in Boston for four years, Bandoni now works as a certified financial planner, director and wealth advisor at Gainline Financial Partners. She is among the 34% of CFP professionals who previously worked in unrelated fields, according to 2023 data from the CFP Board. That aligns with the 2025 Amplified Planning/Schwab Advisor Services research showing nearly 40% of new financial planners are career changers. About one-third of career changers come from a financially adjacent career, such as banking, insurance and accounting, said Lisa Davis, chief program officer at the CFP Board. Another 40% come from a broader category of public-facing or relationship management industries, which range from sales and marketing to retail and hospitality. “In some of the programming that we’ve been doing to specifically help career changers transition, we’re seeing just this broad array of careers,” Davis said. Anyone who has worked to become a CFP knows it’s a rigorous process. Advisors need a bachelor’s degree, coursework in financial planning (either undergraduate or a certification program) and 4,000 to 6,000 hours of experience; they also have to pass an exam and meet an ethics requirement. For July, the CFP Board reported a 66% pass rate . To help prospective CFPs, the board offers guidance and financial support. Since 2016, it has awarded $3.4 million in scholarships, Davis said. This year, CFP Board launched its first scholarship focused on career changers, the Cary Carbonaro Women & Wealth Career Changer Scholarship . It awards up to $5,000 per student seeking to complete a certificate-level CFP Board Registered Program and is designed to support the next generation of women financial planners. Prescription for Change The primary motivators to choose financial planning as a second career include a sense of purpose, helping people, greater work flexibility and being financially rewarded, Davis said. Those reasons resonated with second-career CFPs who discussed their transitions with Advisor Upside. Dr. Bryan Jepson , financial advisor, Targeted Wealth Solutions, transitioned from a 30-year career as an emergency medicine and clinical doctor. ER doctors have the highest burnout rate in medicine and work nights, weekends and holidays, he said. “If you’ve seen The Pitt , then you get it instantly,” Jepson said, referring to the HBO Max medical drama set in a Pittsburgh hospital. He enjoyed making a difference, but he was starting to feel burned out. He had always had an interest in personal finance and investing, and pursued it as a career change over three years ago. While still practicing medicine he received a master’s in finance and then became a CFP. He formally retired from medicine in February. Juggling a career in medicine while prepping to become a financial planner was challenging, but he loved it. “I found that even though I was busier during the process of starting this new career, I was more energized and less burned out,” he said. Flexibility was a big motivator for George Herr , wealth advisor with Mercer Advisors. He left a 30-year engineering career at Ford Motor Co. to join the field, in which he had become interested after working with a financial advisor following the 2008 crash. “My day never ended,” he said, explaining that he collaborated with coworkers and others in Europe and Asia. “When I had a spin class, I tried to do it at 5:30 in the morning. I couldn’t do it. There was a meeting. It was just ridiculous.” His current job gives him greater flexibility to manage clients’ needs, allowing a more nine-to-five career than what he was used to. Herr started on his own advisory path two years before a planned 2020 retirement from Ford by going to night school to meet CFP education requirements. ‘Daunting’ Effort to Become a CFP It wasn’t an easy transition, but the financial advisors are happy they did it. Herr, who has two master’s degrees in engineering, admitted some of the course work and exam prep was much harder than he realized it would be. “It was really daunting. Even as an engineer, it’s totally different,” he said. Bandoni found financial planning th

Robotaxis like Waymo are upending the traditional gig economy. September 27, 2026 PRESENTED BY ORACLE NETSUITE Good morning and happy Sunday. The self-driving future has arrived at your doorstep, at least if you live in cities such as Austin, Los Angeles or Phoenix, and the meter is running. Robotaxis cruising the streets in full force are upending a gig economy that human workers have grown to rely on for fast and easy income streams. What that means for the world of tomorrow and its workers is the subject of today’s deep dive. But first, a word from our sponsor, Oracle NetSuite . Back in the 1990s, basketball legend Michael Jordan collected headlines, sneaker deals and scoring titles for the Chicago Bulls. His eccentric teammate Dennis Rodman scored comparatively little. His specialty was chasing down missed shots and shutting down opponents, which never earned him the headlines but helped win five NBA championships over his career. Sound familiar? Every team has one. They’re the specialist everyone turns to when problems get hard and whose expertise is difficult to replace . And because they rarely look like future executives, they often go unnoticed in succession plans until they resign . Jack McCullough of the CFO Leadership Council argues losing one can actually do you more damage than losing an executive (the Rodman Paradox). In this new guide from Oracle NetSuite , he shows how to spot these individuals on your team, and how to keep them. Read the guide and find the players you can’t afford to lose. ARTIFICIAL INTELLIGENCE The Gig’s Up: Robotaxis, Delivery Drones Reshape the Side-Hustle Market Photo illustration by Connor Lin / The Daily Upside, Photo by Chanakon Laorob via iStock Last week, DoorDash agreed to a $131 million settlement with New York City to resolve a probe that found it not only underpaid many delivery workers but also paid them late. The workforce of the future, however, may be much less insistent on getting its due, not needing to worry about paying the rent or buying food. Whether it’s self-driving robotaxis, flying delivery drones or four-wheeled courier robots, Silicon Valley is rapidly turning to an automated fleet to perform jobs long held by gig workers. Whether the droids will ultimately replace their human counterparts, or merely supplement them, is a question being answered in real time. One study from George Washington University found that the transition to robotaxis could “decrease frontline jobs by 57% to 76%.” The disruption of the gig economy’s informal social safety net is putting Waymo robotaxis at odds with everyday people driving for Uber and Lyft. While almost everyone agrees that some AI displacement is inevitable, experts told The Daily Upside that gig work is more likely to evolve rather than die off entirely. Margin Call Sharing the road with autonomous cars may already feel like the new status quo to the people of cities such as Austin, Los Angeles and Phoenix. Businesses like Uber, Alphabet-owned Waymo, Tesla and others, meanwhile, are trying hard to bring the rest of the world onto the robotaxi route. “Uber is looking to drive out the margins in the business, and what’s the biggest cost to driving a passenger from Point A to Point B? It’s the driver in that equation,” Brian Jackson, emerging technology analyst and principal research analyst at Info-Tech, told The Daily Upside. “If you cut out the driver from it, the cost goes way down.” And put enough robotaxis on enough roads in enough cities, and the economics of driving humans from Point A to Point B suddenly and dramatically change at scale, fueling an explosive expansion in the taxi industry’s potential market. As Uber COO Andrew Macdonald recently put it , a mass fleet of robotaxis that can reliably, cheaply and quickly ferry passengers anywhere they want to go at any moment could disrupt the personal car ownership industry. That world would have just as little utility for driver’s ed instructors as it would for Uber drivers. Robot Economics Such a future could mean a $415 billion global market for robotaxis by 2035, according to a recent Goldman Sachs report , with the US share at $48 billion. How large robotaxi fleets must be to achieve that is an open question. Ditto, how much the cost-per-mile metric must fall. The current cost of owning and operating a personal car in the US comes out to as little as 77 cents a mile, per Goldman, while a typical human-driven rideshare costs about $2 per mile. Robotaxi firms have been opaque about specifics of their still relatively small fleets so far, but most estimates peg current robotaxis as operating somewhere in between the two figures. “To surpass traditional rideshare margins, AV fleets must drive down unit operational costs” by optimizing network planning and routing, reducing human operational support, and minimizing downtime tied to charging and maintenance, Third Bridge analyst Natasha Nair told The Daily Upside. Tipping Point In the present, robotaxis still represent a hair of a sliver of the overall taxi industry. Waymo has rapidly expanded its rollout this year, and now operates about 4,000 robotaxis in 15 cities, completing about 500,000 rides per week . Uber, with its massive army of human gig workers, reported 300 million trips per week globally, including deliveries, in its past quarter. In other words, the great displacement has not yet begun. By most estimates , it’s still at least a couple of decades away. But don’t tell that to drivers in robotaxi-heavy cities. While hourly gross wages for Uber and Lyft drivers increased 1.8% nationwide from the previous year in the last quarter of 2025, wages fell in AV-heavy markets such as Los Angeles (down 3.7%) and San Francisco (down 1.7%), according to rideshare tracking platform Gridwise . “Full displacement may be decades away, but wage pressure is already here,” Veni Dhir, director of corporate venture capital at ADP, told The Daily Upside. “Automation gives platforms option

Spicy Take Sunday 🌶️ 🥛 HYPE could rival ETH ⚔️ Spicy Take Sunday 🌶️ Rohit Chauhan GM. This is Milk Road, the crypto newsletter hotter than a validator's server room in August. Here’s a taste of this week’s menu: 🔥 Ethereum and Base are NOT AT WAR. 🥵 Every company will have its own chain. 🌶️ Galaxy has a secret money printer. HOT TAKES OF THE WEEK 🔥 Base and Ethereum aren't getting divorced 💔 Crypto Twitter is at odds yet again over a technical detail regarding account abstraction, the technology that enables the building of Web2-like user account management systems for Web3. Binji (Founding Member at Ethlabs) is pushing back against the drama after Ethereum and Base gave up on building a shared account-abstraction standard. His take is that Facebook building its own website doesn't mean it has divorced itself from the internet. His analogy: Ethereum is New York, and if every neighborhood were Tribeca, he'd never go. Plus, Base has billions in ETH sitting on it and is consuming blobs "like nobody's business." 🎙️ Listen to the full episode here . Every company gets a chain 🔗 Karl Floersch (Co-founder & CTO of OP Labs) says we're heading to a world of a million chains, where every company has one, just as every company ended up with a website. More than 50 organizations are already running L2s on the OP Stack, and they processed ~6B transactions last year. He says we’re still early, with less than 1% of the global financial system onchain. Karl also said the new SEC/CFTC rulemaking might actually be better than the CLARITY Act, since the bill was full of compromises. 🎙️ Listen to the full episode here . Galaxy's secret money printer 🖨️ Kyle Reidhead (Head of Research at Milk Road) already has 10% of his portfolio in Galaxy, and he's itching to buy more. The market hates Galaxy's crypto business because it was supposed to help fund the AI data center buildout, but Kyle's pointing out that crypto just ran 30%, and nobody remembers how profitable crypto businesses get when volumes come back. His bet is that the crypto side starts printing, that cash funds the data centers, and the flywheel gets massive. 🎙️ Listen to the full episode here . How 2M+ Professionals Stay Ahead on AI What’s the secret to staying ahead of the curve in the world of AI? Information. Luckily, you can join 2,000,000+ early adopters reading The Rundown AI — the free newsletter that makes you smarter on AI with just a 5-minute read per day. HOT TAKES OF THE WEEK (P2) 🔥 Hyperliquid is coming for the #2 spot 🥈 Eliezer Ndinga (Head of Research at 21Shares) is doubling down on his call that Hyperliquid can become the second-largest crypto asset behind Bitcoin. At ~$24B, HYPE trades at 30x+ its gross revenue, and Eli says the Kraken/Payward deal (which opens regulated U.S. access) helps justify that premium. He calls Hyperliquid the "Google of price discovery," with open interest at an all-time high of $18B+. Fun fact he threw in: Google was roughly the 21st search engine, so being early doesn't mean winning. 🎙️ Listen to the full episode here . The market is sleeping on IREN's power 🔋 Martin Toman (Lead Analyst at Milk Road) thinks Wall Street is valuing IREN only on its contracted business and missing the 5GW of secured power it has locked up. For context, Galaxy is in second place with 1.6GW, and demand runs into the tens of gigawatts. IREN's first Microsoft building is already generating ~$1B in revenue, and Martin expects all four buildings (~$4B in total) to be online by year-end. The catch is that IREN needs ~$25B in funding next year, so Martin is modeling 20% dilution and waiting a week or two before he buys. 🎙️ Listen to the full episode here . BITE-SIZED COOKIES FOR THE ROAD 🍪 If you hold HOOD, read this. Robinhood has grown into an all-in-one platform for stocks, crypto, IRAs, prediction markets, credit cards and advanced trading tools.** 21Shares Head of Research says Hyperliquid will eventually trump all competition. Is shielded Bitcoin on the horizon? Polygon burns 100M POL tokens but remain net inflationary. **this is partner content. This content is for educational purposes only. Read full disclaimer Interested in reaching smart readers like you? Sponsor Milk Road Update your email preferences or unsubscribe here © 2026 ImpactDM Inc. operating as Milk Road 1257 Dundas St W Toronto, Ontario M6J1X6, Canada

The stranger side of your portfolio... September 27, 2026 Presented By James Clapham Editor’s note Good morning. It’s time to finally dust off the binder of Pokémon cards that’s been under your bed since 2002. Welcome to Alternative Investments Brew, a special edition all about financial assets other than stocks and bonds. We’re talkin’ private markets, trading cards, fractional horse ownership, domain names, and more. So, close the Stocks app and open your horizons to some very different kinds of investing. setting the scene Kids these days are so alt(ernative investments) Unsplash Put your money in an index fund? And then what? Wait around for 50 YEARS?? That’s still one of the most common ways to invest, but there are others. Alternative investments that historically were reserved for rich people or sophisticated investors have recently attracted more retail investors—especially young ones. But like Pokémon card and private credit payouts, nontraditional investments can present big risks for the uninitiated. Follow the money: Alternative investments, or alternatives, can include a wide range of assets like crypto, meme stocks, real estate, and collectibles as well as private, pre-IPO stocks. And high-net-worth investors aged 21 to 45 are flocking to them: About 67% of Gen Z and millennial investors believe that stocks and bonds can’t deliver above-average returns anymore, according to this year’s Bank of America Private Bank Study of Wealthy Americans. Younger generations’ distrust of traditional institutions plays another big factor in the rise of alternatives, according to the study’s 2025 results. Nearly 20% of millennials’ investment portfolios consist of alternatives, compared with Gen X’s 11% and boomers’ 6%, according to Goldman Sachs data. High risk, maybe high reward Banks and retail trading platforms have scrambled to offer wealthy, younger clients a smorgasbord of new investment options like private equity, real estate, and credit. But the line between the “democratization of investing” and straight-up gambling has never been blurrier with the rise of meme stocks and private-market investments that lock your money in during times of turbulence. There’s a reason these investments were once reserved for teams of institutional investors with deep pockets and time to comb through the fine print: The potential big wins often come with a higher possibility of major losses and less transparency. So, why are alternatives now courting everyone else? Their traditional investors (massive endowments, hedge funds, and pensions) already have about a fifth of their portfolios invested in the asset class, so it’s unlikely they’ll want to toss more money towards alts. Meanwhile, individuals have just 7% of their portfolios allocated to alternatives with plenty of room to grow, according to the 2024 Bank of America Survey.— MM Sponsored By GLOBAL X ETFS Built for the build-out Roads are cracking, grids are aging, and broadband is still waiting to be invited into every household. Independent assessments have been rather blunt about how much needs to be fixed or replaced and the demand that work will create. As it happens, the funding is locked in , thanks to major US policy acts committing historic dollars to infrastructure, setting up a build-out that could run for years. PAVE isn’t betting on just one piece of this story. It invests across the full chain , from the companies pulling stuff out of the ground to the ones running the big equipment. Holdings sit close to the builders, weighted toward industrials and materials. This is a chance to grow with America’s blueprint. Explore PAVE . ball street bets Gen Z sees sports betting as an investment Michael Reaves/Getty Images Why try to figure out how an earnings report will affect a stock when you can figure out how an injury report will affect a sports team? That’s the attitude that some—including a wide swath of Gen Z—are taking when it comes to how to grow their money. One in five Americans view wagering on sports as an investment tool , and for Gen Z, it’s two in five, according to a recent Bank of America survey. And they’re acting on those feelings: A Betterment survey of 1,000 investors found that 52% of Gen Zers redirected money intended for investing into sports betting instead. All this is despite the odds and history screaming to do the opposite: There’s a fee built into the odds of wagers called a vig . The vig is how sportsbooks ensure they make money, and it turns bets with a 50/50 outcome into one where bettors must put down $110 to win $100, which means even if you win 50% of those bets, you will still lose money long term. Meanwhile, the stock market has delivered an average annual weighted return of 10% over the past century, according to research from a professor at Arizona State University’s Carey School of Business. But what if Gen Z is picking winners? They’re not! Almost no one is! That’s why sportsbooks are billion-dollar businesses, and you’re asking your mom for $20 to load into your FanDuel account. That BofA survey found Gen Z is the most successful sports betting generation by recovering 80 cents for every dollar wagered (that’s still fancy bank-speak for losing). There’s likely to be more: Football season, which began on the pro and college levels a couple of weeks ago, typically drives more users to place bets. Last season saw a 22% increase in first-time users year-over-year, per BofA. —DL credit curious Private credit faces highly public questions Getty Images You know your corner of the market has made it to the big leagues when JPMorgan honcho Jamie Dimon cautions that it might bring about the next financial crisis—as he did with private credit earlier this year. Of course, not all the attention private credit has gotten has been negative—or has compared it to a “ cockroach ,” as Dimon memorably did following the collapse of two private credit-backed firms. So, what is it? Basically, private credit means loa