About Fearless Financial

What would being financially fearless mean for you?

Going After Your Dreams?

Being There For People & Moments That Matter?

Living Life Full Out?

Fearless Financial delivers advice-only financial planning for those who see wealth as a vehicle to living a more fulfilling, fearless life. They have big dreams and know smart financial planning can get them there!

We work with women, families, and entrepreneurs in their earning years who juggle multiple financial concerns and responsibilities.

We meet you where you are, analyze you where you are, and prioritize your financial activity to get you on track for your goals. And we make the process fun too!

Let’s Define What Wealth Means to You.

Wealth means different things to different people.
For some people, it means vacation homes and fancy cars. For others, it means early retirement, opening a new business, or having enough money to take a few years off for a sabbatical or family adventure. It could mean building a wing onto a hospital or making a sizeable donation to your favorite nonprofit. Or paying for your grandchildren’s education.

Everyone’s definition of wealth is different, and you can’t pursue it until you define it.

We’re the ones who ask the tough questions to help you define what wealth means to you and then achieve it through a robust, dependable financial plan.

So, what’s your definition of wealth? Tell us and let’s make a plan!

Why Work With An Advice-Only Planner?

Our advice-only model is atypical in the industry. We do not earn commissions on your investments, pressure you to move your money to certain institutions, or hawk any financial products. Instead, we offer advice and a solid, fearless financial plan for you to do great things with your money…and your life!

We are not Commission-Based Advisors who get paid to sell you a financial product (like an insurance policy, investment product, or annuity). Our model prevents the opportunity for product sales to create misaligned incentives.

We also are not Fee-Based Advisors. They receive both fees AND commissions.

We are different from typical Fee-Only Advisors, who generally charge clients a percentage of their Assets Under Management (the AUM Model).

Instead, we are part of a small but growing group of Fee-Only advisors who choose to provide Advice-Only. In our opinion, it’s the best way to help clients review their situation holistically, and empower them with rewarding financial recommendations to reach their dream goals. We can then serve as an accountability partner and sounding board to help you navigate your financial goals over time.

If you are looking for an ongoing relationship with a financial advisor to help you work towards your goals to greater wealth, we’d welcome the opportunity to speak with you.

Meet Amy Rosenow, CFA, CFP®

Entrepreneur, financial industry veteran, hedge fund and angel investor, accomplished speaker, passionate working mom, and philanthropist.

I’m Amy, and I founded Fearless Financial because I’m passionate about helping people build wealth as a way to fuel their personal dreams. I’ve earned my clients’ trust through a life lived in the financial world as a working mom and entrepreneur, financial industry veteran, hedge fund and angel investor, philanthropist, and a source of financial wisdom and guidance for those closest to me.

I want to learn how you define wealth in your life and help you work to create enough to live your most fearless life.

I founded Financial Fearless in 2021 after working in financial services for more than twenty years. After graduating from Cornell University, I worked on Wall Street for JP Morgan, Bear Stearns, and Morgan Stanley before I became Chief Operating Officer, Chief Compliance Officer, and Partner at Sheffield Asset Management, L.L.C., a Chicago-based investment management firm. In my decade there I was responsible for operations, client service, investor relations, marketing, risk management, compliance, and technology.

After Sheffield, I founded Jugl, a software startup focused on streamlining scheduling for working parents. I currently serve as President of both RUOK Management investment partnership and Kaplan Rosenow Family Foundation. I am also the founder of Authentic Capital LLC, which provided outsourced COO services to growing start-ups, and am a mentor at 1871, Chicago’s Center for Entrepreneurship and Technology. In addition, I co-founded the Josephine Collective, which helps women collaboratively become angel investors.

Courtesy of Gregory Rothstein, 1871

Beyond that, I live in Chicago with my husband, two daughters, our chocolate Labrador retriever, and our newly rescued Labrador mix puppy. I love reading, live music (especially Billy Joel), travel and sports. I have adopted some Chicago teams while staying loyal to my NY roots and thus cheer for the Yankees and Cubs, Rangers and Blackhawks, Knicks and Bulls, Giants and Bears (but I do work with Mets fans and both kinds of Sox fans, too!)

Want to talk about developing a financial plan fearless enough to take on your greatest dreams? Set up a time using the link below. Let’s figure out what wealth means to you and how we can get you there!

Our PromiseWe Work to help you stay true to your financial goals.

Our work is anchored by our long-held belief that helping you achieve wealth, as YOU define it, will lead to a happier, more powerful, and flexible life.

We’re All About You!

There’s no minimum asset level required to work with us and you can keep your investments wherever you want. We offer a judgment-free zone as you determine what wealth means to you. There are no stupid questions, shame, or “crying over spilled milk.”

We’re All About Living Life With Financial Freedom!

We believe you can have fun today, including thoughtful splurges, and still save for tomorrow. We want to help you live your most authentic, exquisite life by growing the resources you have.

We’re About Honest Conversations

Difficult conversations lead to more confident financial decisions. Then you can explore new options without fear.

We’re About Integrity

Our reputation is our most valuable asset, so we’ll try our very best to do what we say we will. We set reasonable expectations and strive to exceed them, with responsive feedback and support to our clients.

We’re About Progress, Not Perfection

Major goals take time, so along the way we celebrate the small wins as well as the bigger ones. If your goals change, we adjust the plan, and keep learning and improving. Sometimes the world will change and we’ll need to adjust. That’s all part of the process. Persistent small steps lead to amazing progress!

We’re About Empowering Your Financial Future

We believe that taking an active role in your finances gives you the power to grow and dream. When two partners are involved, we work towards aligning financial goals. Financial power creates options and flexibility to lead your most dreamed-about life, while protecting the things most important to you.

Professional Affiliations