retirement-planning
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Manulife Had $1.3 Trillion - and One Missing Piece
The insurance-born money manager already had global reach, retirement distribution, and deep private-market roots. Its next act is a practical lesson in filling capability gaps without pretending scale solves everything.
Empire Life Spent 100 Years Selling Certainty. Now It Has to Sell Speed.
The Kingston insurer has C$20.8 billion in assets, a century of claims history and a fresh digital mandate. Its most interesting product is not another policy - it is the attempt to make old-fashioned reassurance feel fast.
Manulife Is Turning a 139-Year-Old Insurer Into a Health-and-Wealth Operating System
The Canadian insurer spent years untangling yesterday's promises. Now it is betting that the same customer needs protection, investing, banking and help living longer - and that one global balance sheet can serve them all.
Formations Turns the Freelancer Tax Scramble Into a $350-a-Month Operating System
The Kirkland fintech bundles entity setup, bookkeeping, payroll and tax strategy into one annual commitment. For the right business of one, the prize is predictable taxes; for the wrong one, the cure can cost more than the headache.
The $1.7 Billion Wealth Firm That Sold the Plumbing - and Kept Its Name
US Financial Services spent three decades building a planning practice around life transitions. Then it made a counterintuitive succession move: join a larger platform, preserve the local brand, and turn the firm itself into a home for other advisers.
PlanScout Bought a 13-Year-Old Planning Engine - Then Turned 15 Hours of Advisor Work Into 3
Financial advisors have plenty of software and too little time. PlanScout's answer is a hybrid: buy the planning engine, add a human service layer, and return a client-ready plan in days.
The $4 Billion Freedom Bet: How XML Financial Group Built a Wealth Firm by Refusing to Build Alone
XML Financial Group escaped the big-bank playbook, then discovered that independence works better with infrastructure. Its repeatable trick is equal parts personal advice, succession planning and culture-first M&A.
The Startup That Chases Down America's $2.1 Trillion in Forgotten 401(k)s
Americans leave 401(k)s behind every time they switch jobs. Capitalize built a business on the phone calls, notaries and paperwork nobody wants to deal with.
The $160 Billion Middleman That Made Outsourcing Its Edge
Hartford Funds built a large investment business by deciding it did not need to do every job itself. Now Wellington Management plans to buy the platform it has helped power for four decades.
The $143,000 Bet That Turned a Basement IMO Into Advisors’ Back Office
Advisors Excel began with three friends, a dentist-office basement and their pooled savings. Two decades later, its real product is not an annuity - it is the machinery that lets an independent advisor run like a much larger firm.
The $1.7 Billion Reason Guardian Life Still Believes in an Old-Fashioned Idea
Guardian Life has spent 165 years selling protection against life’s worst timing. Its mutual structure now pairs a record policyholder payout with the less glamorous work of making benefits, claims and leave easier to use.
The Life Insurer That Would Rather You Stay Alive
At 164, John Hancock is recasting the oldest bargain in insurance: instead of waiting to pay after death, it rewards customers for living better now. The experiment links life insurance to wearables, cancer screening, longevity research and a growing stack of health technology.
The Discount Broker That Became Wall Street's $13 Trillion Operating System
Charles Schwab spent half a century making investing cheaper. Now its harder trick is making a brokerage, bank, adviser, custodian and trading machine feel like one calm place to keep a financial life.
IRA Financial
IRA Financial built its name helping retirement savers buy the things ordinary brokerage menus leave out. Now it is stitching real estate, crypto, private companies and public markets into one account - while asking customers to take on the judgment that freedom requires.
Advanta IRA
Advanta IRA gives retirement savers a way to put houses, private loans, gold and startup stakes inside tax-advantaged accounts. The freedom is real - and so is the paperwork.
Horace Mann
Horace Mann built an 80-year business by studying one customer more closely than most insurers study a market. Its wager is that understanding the financial life of a teacher - from the school parking lot to retirement - can still be a durable advantage.
Raymond James
A firm that started in a downtown St. Petersburg apartment now watches over $1.92 trillion - and it still measures itself one advisor and one client at a time.
Oppenheimer & Co. Inc.
A 140-year-old Wall Street house that never grew into a giant - and turned staying mid-sized into the whole pitch.
Mercer
Mercer built an 80-year business around decisions companies cannot afford to guess at - what to pay, which benefits to fund, how to redesign work and where to invest retirement money. Now its vast store of workforce data is becoming a product in its own right.
Equitable
Equitable has spent 167 years selling certainty. Now it is redesigning itself around advice, assets and a proposed merger that would put $1.5 trillion under one roof.
Principal Financial Group
Principal began by selling affordable life insurance to bankers in 1879. Today, its quiet advantage is a workplace-to-wealth pipeline that reaches millions of people before they ever choose a financial brand for themselves.
Vanguard
For fifty years, Vanguard turned a strange ownership structure and a suspicion of fees into an investing machine for ordinary savers. Its next act mixes index discipline with advice, AI tools and private markets - without losing the low-cost bargain that made it matter.
Sun Life
Sun Life spent 160 years learning how to price the future. Now it is turning that patience into a three-part business spanning protection, workplace health and global asset management.
Zoe Financial
Zoe Financial is a New York-based wealthtech company that connects individuals and families with vetted, independent fiduciary financial advisors while giving those advisors an all-in-one platform to run their practices. Founded in 2018 by former J.P. Morgan executive Andres Garcia-Amaya, Zoe pairs a rigorous advisor-matching service - it screens out roughly 95% of applicant advisors - with wealth-management software that handles account opening, funding, automated rebalancing, tax-efficient investing, direct indexing, and commission-free fractional trading. The company raised a $29.6M Series B in 2025 led by Sageview Capital, bringing total funding to about $45M.
Boldin
Boldin (formerly NewRetirement) is a Mill Valley, California fintech that makes comprehensive financial and retirement planning software affordable and self-directed. What began as a spreadsheet built to help founder Steve Chen's mother draw down her retirement savings has grown into a platform where more than 350,000 people have built plans covering over $300 billion in assets. Boldin sells a low-cost consumer subscription (PlannerPlus) plus a free planner, live classes, coaching, and CFP advice, and licenses its planning engine to enterprises like Nationwide and RTX.
Ellevest
Ellevest is a New York-based financial company built by and for women. Co-founded in 2014 by former Wall Street executive Sallie Krawcheck and Charlie Kroll, it launched a gender-aware digital investing platform in 2016 designed around the realities of women's financial lives - longer lifespans, earlier salary peaks and the persistent pay gap. After selling its automated-investing (robo) business to Betterment in 2025, Ellevest now focuses on wealth management and financial planning delivered by an all-women team of advisors for clients investing $500,000 or more.
HerMoney
HerMoney is a digital media company founded in 2018 by longtime personal-finance journalist Jean Chatzky to give women judgment-free money guidance. It publishes the HerMoney podcast and newsletters, runs the FinanceFixx budgeting and InvestingFixx investing-club coaching programs, and partners with employers and financial institutions to close the gender wealth gap.
Waterlily
Waterlily is a San Francisco-based startup that uses AI and more than 500 million data points to predict when and how a person will need long-term care, what it will cost, and how to pay for it. Built primarily for financial advisors and insurance carriers, its software turns one of retirement planning's most avoided questions into a concrete, personalized plan - from care projections to matching families with optimal long-term care insurance policies in under a second.
Chapter
Chapter is an AI-native Medicare advisory platform that helps older Americans choose the right Medicare and retirement healthcare coverage. Instead of acting as a commission-driven marketplace, Chapter reviews plans from every insurance carrier nationwide and pairs that data with licensed, independent advisors to deliver unbiased recommendations. Founded in New York in 2020, the company has supported more than 500,000 enrollees and crossed $100 million in annual recurring revenue.