Breadwinning, Six Figure, Millionaire Moms – Hilary Hendershott

Good morning! I’m very excited today to have another amazing guest for my awesome breadwinning, six figure, millionaire mom series – Hilary Hendershott!

You might already know Hilary as the voice behind Profit Boss Radio, a wonderful podcast for women who want to create success in their financial life. I actually first heard about her on a different podcast (either So Money with Farnoosh Torabi or Her Money with Jean Chatzky-can’t remember now) and have been a listener since – if you haven’t listened before I would highly recommend you do. She’s had articles published in the Wall Street Journal, Forbes, and Investopedia (among others), and she’s currently prepping for a LIVE event in California next month! She runs a leading financial advisory firm focused on women (Hilary Hendershott Wealth Management), has been named a 40 under 40 in Silicon Valley, and is a TEDx speaker.  So I was very excited when she responded to my call for breadwinning mom interviews.

Without further ado, lets learn more about Hilary!

Tell us about yourself!

I’ve lived in San Jose, California, almost all of my life. San Jose is the Capital of Silicon Valley so there’s lots of tech talk here. It’s also one of the most expensive cities in the world to live in! I was never much into tech, though I love what some of it does for my life, but I did have a head for numbers.

I was mentored into the field of financial planning by my father and stepmother, and I can honestly say that I truly love and am fulfilled by what I do. I absolutely love working with my clients! I’m now proud to run a firm with a 3-person team and it’s really rewarding to be a job creator.

I named my company for me. I figured, men do it all the time, so why not? My firm is Hilary Hendershott Wealth Management and I also host a podcast called Profit Boss® Radio where I talk about things like investing, money psychology, and other money-related topics. I’ve also interviewed folks like Jean Chatzky and David Bach. I have a lot of fun with it, and it’s so meaningful for me when people write to me about how much of a difference the show has made in their lives.

In 2018, I’m hosting my first ever women’s wealth-building event, called Profit Boss® Live. It’ll be in San Jose on January 19th, 2018, and I’m excited and terrified at the same time! I’ve always wanted a safe and supportive space to talk about money, but I could never find that… so I’m creating it!


I’m married to a great guy named Robert. He is a university finance professor as well as a hedge fund manager and our firms share an office near the San Jose airport. We just bought a house here in May of 2017—and a fun fact about that house is that he rented the house five years prior to us buying it. Actually, we had our first date at that house! We lived at two other homes in between and then when “Miracle House” came on the market we were blessed to be able to buy it.

Robert and I were married on New Year’s Eve in 2013 and we had our first child, a gorgeous baby girl named Harlyn Simone, in June of 2016.

For fun, I enjoy spending time with my girlfriends, getting a massage, chilling out in the hot tub, and drinking tequila!

Let’s get some details – how much money do you make, and how long did it take you to get there? And are you a millionaire or are you on the way?

I’ve been in the financial services business for about 17 years. I started with a base salary of about $40,000, then up to $65,000, and pretty soon I was making about $110,000 per year. When I went out on my own in 2014, I had about $200,000 of revenue and now my firm has about a half million dollars of recurring annual revenue. Our household net worth is close to $3,000,000 and the value of my business, which is very sellable, is likely about $1,200,000.

How did you get started in the workforce?

I started in management consulting, hated that, went to work as a recruiter in a startup, dabbled in financial services and mortgage brokering, and then applied to law school. I was accepted to law school, but didn’t end up attending, felt very lost for a while, went back to financial services and fell in love with it.

How did you get from where you started to where you are now?

Well I think the most important thing I did that impacted my trajectory as a professional was I made the very tough choice to leave my father’s firm, where I was being mentored as the business continuation plan, and go out on my own. That was probably one of the most difficult conversations I’ve had in my life. Other than that, my “success”, is really just years of very dedicated hard work. Financial services is a very saturated industry and there are hundreds of advisors out there who would love to work with every one of my clients. I have to be “on” – in the know, charming, gracious and opportunistic at all times. I have to take risks and I have to hear “no” and I have to be okay with that. Really, it’s a mental game.

Where do you want to go in your career – and your financial life?

My current goal is to train and develop Associate Advisors to handle much of the day-to-day operations in the firm so that I can work a few less hours during the week. On the side, I coach and lead global leadership programs and I would like to excel at both—business and leadership—and still experience plenty of time and peace of mind. I’m very committed to developing women leaders! Our current mutual financial goal is a $20 million dollar net worth.

What’s the biggest challenge in being a breadwinning mom? What’s the best part?

I was pretty naïve before the baby was born. I was so sure I wasn’t going to be one of those moms who felt guilty about working. And I don’t feel guilty about working, per se, but I do feel torn about how I spend my time. I miss my daughter a lot during the day and I can’t help thinking I ought to be spending more time with her. But I also love my work and want her to grow up with a powerful female role model in her life. Honestly, I’m torn.

Have you ever experienced issues in the workforce because you’re a woman? What did you do in response?

Oh goodness, yes, I’ve experienced “issues” because I am a woman! I’ve been sexually harassed at multiple firms I worked for, I’ve been told what to wear and what not to wear and been made to feel less than. What did I do in response? Well, at the time I dealt with it as effectively and honestly as I could, but ultimately I escaped from corporate America and founded my own firm!!

Chief Mom Officer is primarily a personal finance blog – tell us about your saving and investment strategy

I am a professional investments manager, so this is what I do for a living, but unfortunately the federal government says that also means anything I say about investments can be construed as investment advice. So, while I cannot say anything specific about investing, I can say that my husband and I both work hard to max out tax-deferred savings every year, he saves in a Profit Sharing Plan and next year I’ll have a company 401(k) plan where my employees and I can save. I use low-cost, globally diversified stock investments and I am extremely happy with the returns! If you’re interested, I talk about my investment strategy here.

I’m very passionate about encouraging women to invest successfully to build wealth. Too many of us sit on the sidelines in cash, for fear of making a mistake, but we all need the momentum and growth power afforded by the investment markets to grow our nest eggs and fund our futures.

What’s the top three pieces of advice you’d have for someone just starting out in the workforce, struggling with their career, or just looking to improve how they handle their money?

First, be careful what you say—it tends to come true.

Second, the skills to build wealth are not mysterious or out of reach. If you dedicate yourself to learning the basic principles, and are consistent in your efforts, you can produce the results you want in life.

Third, the world is full of free resources designed to help you get ahead! Get connected with good, reliable sources of information to power your success. My podcast, Profit Boss® Radio, is just one way I give back to the community of women by sharing the best of what I’ve learned—for free!

Where can people connect with you?

Profit boss logo.pngMy website: Hilary Hendershott Wealth Management

The podcast: Profit Boss® Radio

Women’s wealth-building workshop: Profit Boss® Live

Transformational wealth coaching: The $50K Wealth Multiplier Experience

Call me: 877-569-5508

Email me:

CMO Here Again

Thanks so much to Hilary for coming by to share her story! I love how she decided to name her firm after herself, and hearing about her decision to start her own firm. That must have been a scary leap into the unknown, and she’s doing an amazing job at it!

I can so relate to feeling torn between my kids and my work. I love to work – I love my job, and I would go crazy as a stay at home mom. I also want to be a good role model for my three boys, so when they get older, marrying a strong and successful woman would be “no big deal” for them. But at the same time, I miss them during the day, and I do sometimes get jealous of my husband (a stay at home dad) getting to go on so many adventures with the little guy. So being torn is a familiar feeling for me.

Be sure to leave Hilary a comment below, and don’t forget to check out her site, podcast, and some information about that live event if you’re in California!

Want to connect with other money smart women? Join in my Breadwinning Women or Women on FIRE Facebook Groups and find other money smart women like yourself.

If you haven’t already, be sure to swing by my one-stop shop page for Breadwinning moms, featuring all my prior articles and interviews (plus some updates on prior interviewees!). Know someone that would be perfect for this series, or is that you? Hop over to my “Be Featured!” page to access the request form.

Be sure to follow my blog for more great posts via e-mail or WordPress, or connect with me on Facebook or Twitter and say hello! You can also check out what I’m buying or baking on Instagram,  what I’m pinning on Pinterest, or the latest books I’m reading (or want to read) over on Goodreads.

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1 thought on “Breadwinning, Six Figure, Millionaire Moms – Hilary Hendershott”

  1. I resonate with the aspect of not feeling “guilty”, but feeling a bit “torn” at times. I find the being a working mom is a constant balancing act both in my work and family life, but also in my personal feelings and mentality.

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