Pivotal Money Conversations that Transformed the Lives of 27 Women Leaders

Pivotal Money Conversations that Transformed the Lives of 27 Women Leaders

In recent years, money has increasingly become less of a taboo topic, partially due to the conversations boomers had with their millennial children about personal finance. This openness has made it easier to discuss salary, to negotiate raises and higher rates, and, for women especially, to benefit from financial transparency.

Take it from these 27 successful women, each sharing a significant money conversation that altered their careers and lives. From Lexi’s decision to remove emotion from any conversations about finances, to Charmaine’s breakthrough of effectively articulating her value, these stories highlight the power of talking about money.

If you’re thinking about rewriting your own money journey, you won’t want to miss learning about these financial epiphanies. While inspiring, these reflections are also a reminder to us all that open discussions about money can drastically and positively change the way we live.


Adebukola Ajao

Digital Marketing Consultant at B.D.Y. CONSULT, a marketing agency providing small businesses and badass brands with creative and efficient marketing services.

“A conversation with my colleague and now business partner about my finances changed my life. He showed me that I wasn’t broke, but rather I lacked a healthy financial profile. This realization prompted me to invest, use debt strategically, and leverage credit to grow my business. I now approach money as an investor, actively using it to generate more wealth!”

Julie Zhu

Fractional CMO at Julie Zhu LLC, a company helping early-stage entrepreneurs gain visibility and scale their businesses.

“I was pretty cautious about discussing money in my early days as a marketing strategist. A colleague once suggested I should just be upfront and ask if clients have a budget in mind. That advice was a game-changer for me. Now, I’m confident to have open chats about budgets and costs right from the start. It’s helped me tailor my services, set clear expectations, and build trust with clients. This simple shift in approach has been a major key in growing my business and building long-lasting client relationships.”


Lexi Hartmann St. Laurent

Founder and CEO of iHartContent, a bilingual, boutique content agency dedicated to empowering impact-focused founders and creators to own their digital narrative.

“When it came time to negotiate a salary for my first major leadership role, I was terrified. The fear of being rejected and undervalued was overwhelming. My husband was baffled. He couldn’t understand why a conversation about money would be emotional. This made me realize how significantly impostor syndrome was hindering my growth. I decided to be bold and ask directly for what I wanted without unnecessary explanations. To my surprise, they agreed. It became my first six-figure role. Now, I consciously choose to remove emotion from any conversation about money. This policy has led me to feel much more comfortable in asking for what I’m worth—and earning a lot more as well!”


Charmaine Green-Forde

Founder and CEO of Chapter tOO, LLC, an organizational and talent development optimization consultancy, leveraging data-backed people insights.

“I had a pivotal money conversation with a hiring manager who repeatedly asked if I was countering their initial job offer, which I hadn’t considered doing. This experience served as a wake-up call, highlighting the power of negotiating and articulating my value. It taught me the importance of knowing my worth and asking for what I want. Since then, I’ve approached money matters with a more assertive mindset. I’ve made it a mission to empower other women to do the same.”


Jessie Young

Global Head of Restricted Retail at Uber, changing the way the world moves for the better.

“In the early stages of my corporate career, a partner at my management consulting firm who wore dollar sign cufflinks told me, “No one ever saved their way to wealth.” It blew my young mind. I had gone from running my own yoga business, which was scaling on the side, to now taking a decent six-figure salary. I thought my salary was the key to wealth, but what I’ve since learned is that wealth is greater than money. Your wealth is a function of the value you hold. Money is a function of the currency you have. The equity I have in the yoga business is wealth, and the cash I make teaching a class is money. The latter will pay your bills, whereas the former will make you richer.”


Melissa Lohrer

Founder of Waverly Ave Consulting, partnering with creative agency founders to create sustainable and profitable growth strategies on their path to seven figures.

“At my first job, I was promoted from receptionist to executive assistant with no salary increase. I had other executive assistant friends in the company, so I knew roughly what I should be making. I got the courage to ask if they would consider a $2,000 increase to account for my increase in responsibilities. I was told I’d have to wait at least a year before I could be considered for that kind of raise. One month later, I quit. The best part is that on my last day at that company the replacement I spent two weeks training decided to quit. They offered me a $20,000 raise to stay. Long story short, I declined and my career took off.”


Zahra Yarahmadi

Founder and CEO of BG Financial Consulting Group, a fractional CFO service that provides strategic financial consulting services for scaling technology startups.

“My dad is a successful entrepreneur who always told us two things: focus on increasing your income rather than stressing over cutting costs, and getting a big piece from a whale is better than chasing thousands of fish.”


Evan Sargent

Founder and CEO of Leap_year Branding, building great brands fast for visionary organizations and serial founders.

“I spent a significant portion of my 401(k) in the early days of my first business. My husband was upset when I told him, but I didn’t understand. I think as a woman I clung so tightly to the idea that this was my hard-earned money. I was resentful that he was earning less and wasn’t appreciating the financial value of his work as a stay-at-home parent. It opened up the lines of communication about money and our relationship is stronger for it.”


Danielle D’Agostaro

Partner at WVV Capital, an early-stage joint venture fund targeting transformative innovations in the areas of healthtech, manufacturing, building tech, fintech, and insurtech.

“In my family, money wasn’t one conversation; it’s a frame of mind. From a young age I was told about money: how to make it, and, most importantly, how to save and spend it wisely. That started with getting a debit card, learning how to write checks, and building credit at the age of 16. All those conversations paid off. Being confident in my finances has led me to be an even stronger, independent woman today.”


Jessica Alderson

Co-Founder and CEO of So Syncd, a dating app that matches compatible personality types.

“Prior to setting up my own business, I worked in finance. Being surrounded by people who were constantly striving for more money made me realize that your bank balance doesn’t determine your happiness. One day, I had a conversation with a colleague who told me about the pressure he constantly felt despite earning a high salary because his lifestyle had expanded to match his income. This conversation changed my perspective on money and how I viewed success. I started reading about minimalism and saw how living with less can actually bring far more fulfillment in life.”

Ronit Menashe

Co-Founder and CEO of WeNatal, the first comprehensive prenatal vitamins for her and him, backed by science and mama-approved.

“One money conversation that significantly impacted my life and career occurred during my MBA when I secured an internship opportunity at Nike alongside a male MBA student. Coming from a culture in Israel where people are direct about money, I openly discussed our salaries with him. To my surprise, despite my greater experience, he was offered a higher salary. This experience prompted me to challenge the initial offer and advocate for a salary match, which I successfully achieved after confronting HR. It was a valuable lesson that taught me not to settle for the status quo.”


Marnie Rabinovitch Consky

Founder and CEO of Thigh Society, the leading direct-to-consumer brand of size-inclusive long leg undergarment solutions to sweating, chafing, and modesty.

“One game-changing money decision I had as an entrepreneur was about setting the right prices for our products from day one. Mentors advised me to set prices that were high enough to cover our product and shipping costs. I really honed in on what made our unique undergarments special, did market research to understand what similar products were priced at, and built in room to cover marketing and other operational expenses. Since my company is bootstrapped, I started with the goal of being profitable. This still guides all budgeting, investments, and long-term financial plans for the business today.”


Kelly Hubbell

Founder and CEO of Sage Haus, helping busy moms have it all without doing it all through a series of digital courses and resources.

“The most life-changing conversation I had about money was with my spouse. I made an exhaustive list of all the things I was doing to keep our household running. I sat down with my husband and had a conversation about this list, the value of my/our time, and how we could work hiring and outsourcing into our budget. Five years later, with two more children, we have a team of superstar humans who help us run our household. It’s the best money we’ve ever spent.”


Dr. Leslie Dobson

Clinical and Forensic Psychologist at Dr. Leslie Dobson Psychological Services, working to empower women and educate on setting healthy boundaries with toxic people.

“I’ve always struggled to put a value on therapy or psychological services. I once had a lawyer explain to me that people are not just paying for that hour but paying for your years of education and experience. He said lawyers don’t have a problem charging for 15-minute increments, so why would a psychologist feel guilty charging for an hour? Understanding how other people manage money was extremely insightful to my finances and my practice. Understanding my worth was even more important.”


Amanda Hofman

Co-Founder and CEO of Go To Market, looking to change the way the world handles swag by revolutionizing the way companies think about branded merchandise. 

“Early in my corporate career, I experimented with allowing for silence in my money conversations. In my annual reviews, when asking for raises, my instinct was to immediately rush in with caveats and apologies. Taking a moment of silence and getting out of my own way was frightening but ultimately allowed my confidence to grow. So many women can benefit from this accessible but powerful tip!”


Emilie Mascarell

Founder and CEO of Emilie Consulting, specializing in fragrance and beauty product strategy and development, helping companies in bringing their vision to life.

“A friend highlighted that my client pricing isn’t solely based on the time spent in a 30-minute chat, but that it also reflects over 15 years of experience in the fragrance and beauty industry. This experience allows my clients to save time and money, steering clear of costly mistakes and ensuring successful product launches in the market. Now, I approach discussions about money with more confidence, understanding the true worth of my expertise and ensuring fair compensation for the tangible benefits my clients receive.”


Annie Franceschi

Founder of Greatest Story Creative®, helping coaches, consultants, and service business owners confidently brand and grow their businesses.

“The day I discovered simplified pricing was a game changer. A systems strategist showed me a competitor in the branding space who was charging X payments of Y for her services. I’d been quoting odd numbers like $3,675. My prices were lower than this competitor for similar services, even though I had stronger credibility. Seeing this simpler pricing in action inspired me to both raise and simplify my packaged services for done-for-you branding and business coaching. Now, my high-ticket offers are always provided in the context of X even payments of Y. This way, clients can easily do the math and see the value. This simple shift has grown my revenue an average of $50,000 year over year and empowered me to break free of the hourly pricing trap!”


Amy Schultz

Co-Founder of Bolder Money, helping women build financial confidence with a financial coaching community that offers personalized, compassionate guidance. 


“The money conversation that changed my life the most was when I told my partner I was emptying my 401(k) to start a business helping women build financial confidence. I knew it was a risky move, and I knew it wasn’t something I would recommend to anyone else. I also knew nothing was going to stop me from fulfilling this dream. The feeling that I had options and potential to build something great because I had access to that money is the same feeling I try to give women now.”


Dawn Scott

Founder of The Empowered CPA, helping small business owners, gig workers, side hustlers, and everyone in between have access to reliable accounting and tax information.  

“About three years into my business, I was working like a crazy person and my revenue looked more like I was spending my days doing nothing. I was talking to my husband about my workload. He plainly looked at me and said, ‘Are you running a not-for-profit? Because it feels like you are.’ I realized I was doing a majority of my work pro bono because I was worried about how my fees would strain my clients. After a day or so of stewing, I knew he was right—this wasn’t sustainable. Before I take on any projects now, I look at the client, the associated fees, and decide if it is worth taking time away from my family.”

Tiffany Coyle

Co-Founder and CEO of Twinning Pros, a marketing agency helping brands of all sizes attract, convert, and retain customers with a powerful online presence.

“An old coworker of mine taught me to go into any conversation about money confidently and to understand that it’s a two-way street. They will ask you all day long what your salary requirements are or what your quote for the project is. And you shouldn’t be afraid to ask them what their budget is. I can better assess whether the opportunity aligns with my financial goals and whether there’s room for negotiation. It’s about finding the right fit for both parties involved. Now, when I enter into money conversations, I feel confident and empowered.”


Stephanie Loewenstern

Founder of BrightLink Talent, a woman-owned recruiting firm that places top, diverse talent for high growth startups and technology companies.

“My approach to money transformed when I understood the power of mindset and energy, combined with hard work and being present. I’ve learned to believe that my thoughts and beliefs shape my reality, leading me to envision myself as worthy of a six-figure salary. This shift from a scarcity to an abundance mindset changed my life. I’ve learned that wealth and financial success is not just about effort, but it’s also about aligning belief, presence, and action.”


Lori Sussle Bonanni

Communications Consultant at elssus, LLC, building and growing companies’ reputations to increase awareness and business results.

“Early in my career I realized I was underpaid by about $10,000. I was annoyed but gave my boss and the company the benefit of the doubt. I scheduled a meeting, brought piles of research, and, within a few days, secured myself a $10,000 raise. That experience early in my career gave me the confidence to make the ask in other roles throughout my career. If you don’t ask, the answer is definitely no.”


Marissa Joy Pick

Founder of Marissa Pick Consulting LLC, providing strategic consulting focused on digital transformation, content marketing, social media strategy, personal branding, and more.

“Be free from emotion and set an agenda. My mentor once told me to always communicate clearly and set the grounds as to the reason for the discussion, the outcome you desire, and the discussion points you plan to cover. Before an important conversation, always remember to take a deep breath and set your intention. Make sure you’re very clear in your own mind before the other person is present.”


Kimberly C. Tara

Certified Tax Coach at The Tara CPA Firm, LLC, the go-to elevated experience for CEO mom service providers who want to keep more money in their pocket and build wealth.

“One of my very first business coaches had me write out my ‘money story’ when we started working together. I thought it was silly, but I humored her and did the exercise. What I learned was that I was letting the past generations of ‘you have to work hard to earn money’ stop me from charging my worth. I was on a hamster wheel literally working harder, so I could make more money. Now, years later, I know the value I bring to my clients. Allowing ease and white space in my life has created much more abundant growth!”


Sydney de Sherman Arenas

Founder and CEO of Montie & Joie, connecting customers to a global community of talented artisans and revolutionizing the fashion, homegoods, and interiors industry.

“In my mid-20s, I faced a pivotal moment in a business negotiation for my ethically-driven online marketplace. I had such a strong desire to make a positive impact that I unwittingly granted my business partner undue influence, not realizing the power imbalance at play. The business crumbled due to her fraudulent actions. This left me to reevaluate the level of influence and control I would require in future businesses. I now regularly take time to reflect and evaluate my influence in my businesses. This helps me to balance control, encourage growth, and ensure my impact aligns with my world-changing aspirations.”


KK Hart

CEO of Hart Marketing & Communications Inc, a multi-disciplinary business advisory and marketing company.  

“I struggled for years with the idea of being a working, professional mom and was genuinely worried I would regret it. The best money advice I was ever given was to focus on enjoying the balance in life. Using that advice, I intentionally sought out and spoke to highly successful momprenuers to better understand the highs and lows of motherhood, specifically as a longtime entrepreneur. I had many conversations that were super authentic and challenged my thinking. It ultimately created a complete breakthrough in this stuck point of my life. I felt compelled to pursue growing my businesses at the same time as my heart for family. I approach money as a way to add stability and support, but I don’t make it the be-all and end-all of who I am and how I view myself.”


Jamie Ruden

Founder of Be Spotted, a pet marketing program for pet businesses to learn how to best market online and create digital products generating thousands every month.

“As a solopreneur, generating revenue is always top of mind. You only make money when you put the effort in and set up systems for success. My biggest concern at the start of my entrepreneurial journey was to ensure I had enough money to be comfortable. But someone once told me, ‘You know you’ve made it when you go to the grocery store and don’t need to check the price tag.’ Since then, having that marker has helped me stay in check and not stress about hitting crazy financial goals.”



All individuals featured in this article are members of Dreamers & Doers, an award-winning community that amplifies extraordinary women entrepreneurs, investors, and leaders by securing PR, forging authentic connections, and curating high-impact resources. Learn more about Dreamers & Doers and get involved here.

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