Sallie Krawcheck
CEO, Ellevest
Sallie Krawcheck is the CEO of Ellevest, a digital financial advisor for women, and a former Wall Street executive.
Global Business / Economy
Should You Tell Your Employer You Have a Side Business — or Is That Conversation Always Riskier Than It Seems?Should you tell your employer about your side business? There is no universal answer. Disclosure can strengthen trust and prevent future conflicts, but it can also create unnecessary scrutiny if your business has no connection to your employer. The deciding factors are your employment agreement, the nature of your side business, and whether it creates actual or perceived conflicts of interest. In many cases, the safest approach is neither automatic disclosure nor automatic secrecy—it is understanding your obligations before deciding.
Credit & Personal Finance
Should You Trust a Bank's Own Financial Planning Tools — or Are They Designed to Sell You Products You Wouldn't Otherwise Choose?Bank-provided financial planning tools have become increasingly sophisticated, offering budgeting, savings projections, retirement calculators, and personalized recommendations within the same apps consumers use every day. While these platforms can improve financial awareness and make planning more accessible, they also operate within institutions that have products to sell. The key question is not whether these tools are useful—they often are—but whether users understand the incentives behind the recommendations they receive. Used thoughtfully, bank planning tools can serve as valuable starting points, provided consumers recognize where objective guidance ends and product marketing begins.
Credit & Personal Finance
Is Chasing a High Credit Score Optimizing Your Financial Life — or Just Making You Better at Playing a Game You Didn't Design?Nearly 70% of Americans say their credit score is vital to their financial health — but is obsessing over that number actually building wealth, or just making you better at a game the financial system designed for its own benefit? Sallie Krawcheck, Robert Kiyosaki, and Jean Chatzky debate what a high credit score is actually worth.
Credit & Personal Finance
Should You Automate Every Financial Decision You Can — or Does Removing Yourself From the Process Make You Worse With Money Long-Term?Over 50% of Americans say they feel anxious about their financial future — and automation promises to take the stress off your plate. Sallie Krawcheck, Carl Richards, and Robert Kleiman debate whether automating your finances builds good habits or quietly disconnects you from the skills you need to manage money well long-term.
Credit & Personal Finance
Should You Pay Off Your Student Loans Aggressively — or Is That Money Better Spent Building Your Career Instead?Student loan debt in the U.S. has topped $1.7 trillion — so when extra cash comes in, should it go toward crushing that debt or building career skills that could pay off even more? Sallie Krawcheck, Farnoosh Torabi, and Jean Chatzky debate where young earners get the best return on their money.
Global Business / Economy
Should You Pay for a Financial Plan Upfront — or Is a Free Consultation All You Really Need?Only 30% of Americans feel confident in their financial decisions — so when you sit down with an advisor, should you pay for a full plan or start with a free consultation? Sallie Krawcheck, Michael Kitces, and Jean Chatzky weigh in.
Credit & Personal Finance
Is Life Insurance a Smart Financial Tool for the Self-Employed — or an Unnecessary Expense?For the self-employed, there's no employer picking up the tab on life insurance. So the question falls entirely on you — is it a smart financial tool or money better deployed elsewhere? A financial educator, a CEO, and a CPA disagree sharply. One verdict.