Episode 23 - Building Flexibility and Optionality with Amy Rosenow

Today we welcome Amy Rosenow, founder of Bold Vision Financial in Chicago. Amy's career started on the floors of commodity and equity options exchanges, spent years at JP Morgan and Morgan Stanley advising, served as COO of a billion-dollar hedge fund for over a decade, then pivoted into software (founding Juggle, a tool for working parents). During COVID, she earned her CFP® and launched Bold Vision. She's also co-founder of the Josephine Collective (democratizing angel investing for women) and co-founder of the Advice Only Planners Association.Her through-line isn't the roles themselves—it's the principle of optionality. At each career step, Amy asks not "Is this my final destination?" but "Does this give me optionality for multiple paths forward?" That mindset, combined with her unique vantage point across investment management, entrepreneurship, and financial planning, gives her a rare lens on what makes financial advice actually work for smart, accomplished people.Key Topics Covered:Optionality as a Career North Star - Rather than chasing a single end goal, build skills and networks at each step that create multiple future pathways; this flexibility has enabled Amy's seemingly divergent career pivotsThe Conflict-Free Clarity of Advice-Only - When you're not managing assets or earning AUM fees, you sit on the same side of the table as clients; you can freely recommend rolling money out of accounts, owning concentrated stock, or not buying insurance without financial pressureThe Cash Bias in Female Clients - Women clients hold significantly more cash than similarly situated men and more than they need; while feeling safe, this means missing years of taxable investing—a major wealth-building tool over the past decadeAngel Investing as a Wealth-Building Tool (at the Top of the Pyramid) - Angel investments are high-risk, high-reward personal investments in early-stage startups; the Josephine Collective model lets accredited investors participate with as little as $1,000 per deal (vs. typical $10K-$50K minimums) by pooling capital; "power law" returns mean most wealth comes from a tiny fraction of companiesThis episode offers insights for advisors on how to position advice-only as a trust mechanism and for clients on a counterintuitive barrier to wealth-building that many successful women share."The goal is not to be like Scrooge McDuck and die with a swimming pool full of gold coins in your backyard, but to really understand what makes a good life for you and align your financial life with that vision." – Amy Rosenow