Promote Yourself to CEO | Small Business Strategy for Women Entrepreneurs

You are the one everyone calls when something goes wrong, and you’re also the one who’s supposed to be growing this company. This is the full CEO Ceiling Assessment, recorded live on October 20th.
Score yourself green, yellow, or red across the five places capacity breaks in a service-based, relational business.
Grab a piece of paper before you press play. You’ll score:
 → Calendar & Buffer
 → Your Business HQ
 → Your Out-of-Office Plan
 → Feedback Loops
 → Marketing Strability
You’ll leave knowing which one is holding your ceiling in place, why your reds are connected, and how the 90 Day CEO Operating System® maps to each one. Then you can spend the next 90 days on the one that matters instead of trying to fix all five at once.
Ready to work on your reds? The CEO Collective® is taking 12 new members for November. Doors close Friday, October 30.
Want to talk with me? Jump on my calendar here! 
Connect with Me:
Instagram: @racheal.cook
TikTok: @rachealcookmba
LinkedIn: @rachealcook
YouTube: @the_ceo_collective
Website: The CEO Collective
Subscribe & Review:
If you loved this episode, please take a moment to subscribe and leave a review on Apple Podcasts!
🎤 Thanks for listening! I'll see you next week!

There’s a continuing education course in financial services where advisors get reminded to talk to both people sitting across the table from them. As in, actually have a conversation with the wife. That one reminder tells you a lot about the client experience women have been handed when it comes to their own money.
My friend and client Cris Caruso (who first joined me on the podcast here) came up in that industry, and she watched what happened on the back end of it. When a woman who never had a relationship with the advisor was widowed or divorced, she walked away. Of course she did. Nobody had ever bothered to build one with her.
The default setting, especially when it comes to money, is still that the man is the one who manages it, and an entire industry was built around that assumption.
So Cris built Savoire Financial here in Richmond, and it just turned four. It’s woman-owned and queer-owned, built for Gen X and elder millennial women who make the money decisions in their households, who are often the breadwinners, and who have never once seen themselves in the financial services industry.
She also brought a hospitality background into one of the most transactional industries out there. How? By building systems. When a client moves, a welcome-home card and a return address stamp with the family’s name show up from an Etsy seller her team has worked with for years. When her federal employee clients were carrying the weight of DOGE last year, her team sent care packages. And her practice grows primarily through referrals, because referrals only come when people feel cared for.
And then she took the entire month of August off. We started planning that sabbatical together in January, and she walks through exactly how her team and her clients were ready for it.
This conversation is part of The Matriarchy Would Never series, and it’s what the whole series has been building toward – a business where everyone at the table wins. Grab a notebook for this one, because you’re going to want to steal at least three of Cris’s ideas for your own clients!

About Cris Caruso
Cris Caruso is the founder of Savoire Financial, an independent financial planning practice in Richmond, Virginia, built for Gen X and elder millennial women who are the financial decision-makers in their households, and for LGBTQ+ clients who were taught that money wasn’t for them. She has been in financial services since 2004, and she builds her practice around education, behavioral decision-making, and relationships.
Cris is a twice career changer, with an associate’s degree in hospitality management and a bachelor’s degree in education, and she worked guest services and concierge in high-end hotels and on a cruise ship before she found her way into financial planning. She launched Savoire Financial in 2022, grows primarily by referral, and is a member of The CEO Collective®, where she plans her year (and her sabbaticals) on the 90 Day CEO Operating System®.
Connect with Cris Caruso
Website: savoirefinancial.com
LinkedIn: Cris Caruso on LinkedIn, where she posts about current market events, financial news, and behavioral decision-making
What You’ll Learn in This Episode
→ Why financial advisors still have to be reminded to talk to the wife, and what happens to that relationship the day she’s widowed or divorced
→ How Cris brought a hotel concierge mindset into financial planning, including the welcome-home system that takes her team about five minutes
→ The two premises Cris opens every new client conversation with, and why that’s the foundation of a referral-based business
→ Why shame-based money advice keeps people from ever calling back, and how Cris delivers bad news in a way that is clear and kind
→ How Cris planned a full month off this summer, from the decision tree for her team to Monday morning office hours (and why August was the only month that would work)
→ What it means to work for enough instead of a never-ending more, and why some of her clients are saving so much for retirement that they aren’t living their lives today
Key Concepts from the Episode
Money Is Intimate, So Start With No Judgment. Cris opens every new client relationship with two premises. Money is personal and carries a lot of emotion and money stories, and there is no judgment, just facts. Whatever happened in the past gets named and owned, and then the work is the next smart decision.
Nobody makes good decisions in shame. Name what happened, own it, and move forward from where you are today!Hospitality Is a System. The handwritten notes, the welcome-home cards, and the care packages aren’t Cris remembering to be thoughtful on a good day. Her team knows exactly what to send, when, and who to order it from, so every client gets the same care without it living in her head.
It doesn’t take an overwhelming effort. Pick one life moment your clients go through and decide ahead of time exactly how you’re going to show up for it.Be One of the Calls When Life Happens. Pregnancy, divorce, a death, a job change. Every life event has a money decision attached to it, and Cris builds her relationships so she’s in the top five or ten people her clients call when one of them happens.
Referrals come from how people feel when life gets messy. Build the relationship long before they need you!Plan Time Off Around Your Business Cycles. Cris looked at the rhythm of her practice and saw that August was her quietest month. Capitol Hill shuts down, her clients are on vacation or in back-to-school mode, and nobody wants to talk to their financial planner anyway. She started planning in January, told clients in June, and gave her team a decision tree for what they could handle.
Don’t wait until you’re burned out or there’s an emergency to take time away. Find your quietest season and start planning for it now.Work for Enough, Not for More. Cris knows what her household needs, what her future needs, and what it takes to pay her people, and she works for that. Enough includes maxing out retirement, and it also includes living a life you love today.
More never comes when you haven’t defined it. Decide what enough looks like for your LIFE, and build your business toward that.Resources Mentioned
Unreasonable Hospitality by Will Guidara. The book Cris recommends for anyone who wants to understand how the little things make people feel seen. If you’ve ever wondered how to bring a five-star hotel feeling into a service business, start here.
Clear is kind. Unclear is unkind. Brené Brown’s line that Cris leans on every time she has to deliver hard news to a client.
How Cris Caruso Built a Financial Practice for GenX Women and LGBTQ+ Communities. Cris’s first time on the podcast, when Savoire Financial was just getting started. Listen to the two back to back and you’ll hear exactly how much has grown.
Cris’s CEO Collective success story. How Cris built her first year with a foundation-first plan, in her own words.
The CEO Ceiling Assessment replay. A free 50-minute workshop where you score the five areas that decide whether your business can run without you holding all of it.
The CEO Collective®. Where Cris and I mapped out her sabbatical, quarter by quarter, starting in January.
The On-Demand CEO Retreat. The same planning process we walk through together at the retreat, on your own schedule.
The Matriarchy Would Never Assume You Are The Safety Net. Where the series started, with the underlying assumption that someone else is handling LIFE.
The Matriarchy Would Never Sell You Patriarchy in Pink. Why girl boss culture changed the vocabulary and not the structure.
The Matriarchy Would Never Shut Down Your Critical Thi
Connect with Me:
Instagram: @racheal.cook
TikTok: @rachealcookmba
LinkedIn: @rachealcook
YouTube: @the_ceo_collective
Website: The CEO Collective
Subscribe & Review:
If you loved this episode, please take a moment to subscribe and leave a review on Apple Podcasts!
🎤 Thanks for listening! I'll see you next week!

A CPA once looked at how I run my business and said, “You spend way more per client than most other people running these types of businesses.” And I said, “Yep, I’m fine with that.” That one exchange is what a values-driven business looks like on a spreadsheet.
After four episodes of The Matriarchy Would Never taking apart the standard playbook (the safety net we’re all expected to be, patriarchy in pink, the persuasion tactics, and leaving yourself out of your own plan), you’ve probably been thinking, “Okay, Rach, what do I actually do with this information?”
So I’m going first. I’m walking you through five decisions I made inside The CEO Collective®, one in each area of the 90 Day CEO Operating System® (vision, values, leadership, team, and client experience), and exactly what each one cost me.
Saying no to conferences and travel when my kids were babies and toddlers. Paying my team as generously as I can when so much small business advice is about finding the cheapest person for the job. Staying in the delivery of my programs so every single question gets answered, instead of cherry-picking during the live Q&A.
Every one of these decisions cost me something – revenue, sales, sometimes credibility with people who measure success differently than I do – and they’re the reason I’m still here almost 20 years in.
Because when a business runs on the patriarchal default, someone always absorbs the cost when things go wrong, and it’s usually whoever has the least power. Your team member. Your client. Or you, in the years you can’t get back.
This isn’t a template (your business is not my business!). It’s my thought process, so you can take the questions instead of my answers, starting with the one I now run on every big decision: who absorbs the cost if this goes wrong?

What You’ll Learn in This Episode
→ Why I walked away from the typical MBA career track in 2008, and how I defined success for my life before I ever started this business
→ How I revisit my vision every few years by asking what season of life and business I’m in (including the season I had to take care of my mom), and why my growth trajectory will never be growth at all costs
→ The five core values we use as decision-making criteria inside The CEO Collective®, right down to our policies and terms and conditions, and why I credit Erica Courdae and India Jackson for teaching me how to build values you can run a business on
→ Why we work exclusively with women (all women), and what happened every time I let men into the room
→ How I stopped over-functioning at work and at home, and why saying no more often is how I make time for my hobbies, my health, girls’ trips, and my family
→ Why I pay my team as generously as I can, a lesson I learned from my dad, who has run his business for over 45 years
→ Kitchen Party Vibes: how I design my client experience like a host, and why I’m always involved in delivering my programs
Key Concepts from the Episode
Define Success for Your Life Before You Build the Business. In 2008 Racheal had every outside marker of success and a front-row seat to the men 20 years further down the same track, working 80-hour weeks with no idea who their kids’ doctor was. So she defined success across life and lifestyle, health, relationships, fun and creativity, and spirituality before she started, and she revisits it every few years as the season changes.
If an opportunity is only kind of a fit, it’s not a fit. Run it against your definition of success, and if it’s not a hell yeah, it’s a hell no!Values Are the Rules of the Road. Your vision is where you’re headed. Your values decide how you behave and how you make decisions on the way there. Racheal’s five values are public on her About page, and every policy, the terms and conditions, and the whole client experience gets run through them.
If your values only live on your website, they’re not doing their job yet. Pull them out the next time you make a big decision or write a new policy, and ask if it’s in alignment!Stop Over-Functioning and Start Protecting the Asset. Women are trained to do more than they need to, at work and at home, which shows up as scope creep, a maxed-out calendar, and carrying the whole mental load. Self-leadership starts with better boundaries, fiercely protecting your time and energy, and saying no a lot more than you say yes.
Protect the asset – the asset is YOU. Making sure your needs are met isn’t taking anything away from anyone else, it’s how you keep meeting their needs, too.Pay Your People Like You Value Them. Asking how little you can pay someone to get your needs met is an extractive mindset, and people can feel it. Paying as generously as you can attracts more qualified, more talented people who stay for years and bring their best work.
When you take care of people, your people take care of you. If you’re shopping for the cheapest person you can find, don’t be surprised when nobody sticks around!Host Your Clients Like a Kitchen Party. Most programs pour everything into getting people through the door. Racheal designs from the other end: orient people, build the container with clear expectations and onboarding, connect them to each other, and only then start the transformation work.
Don’t spend all your energy marketing and selling to get people through the door and then forget to be a good host once they’re inside your house.Resources Mentioned
The CEO Ceiling Assessment. If you heard the over-functioning section and thought, that’s me, this is where we find out exactly where your buffer is missing. Fifty minutes, live and free, and you score five capacity domains green, yellow, or red as we go. Tuesday, October 20 at 12PM ET, and you get the replay if you register.
Our core values. All five values Racheal walks through in this episode, life before business, we are the new economy, in women we trust, we are stronger together, and human first, always, are public on our About page.
Our AI statement. The newest value, and the clear guidelines behind how we will and won’t use AI in a relationship-driven business.
Erica Courdae and India Jackson. The two people Racheal credits with teaching her how to build values that work as real decision-making criteria, not words picked from a word bank.
The On-Demand CEO Retreat. If you want to take the vision work from this episode into an actual plan for your next 90 days, the on-demand version is the place to start.
The CEO Collective®. The membership where service-based, high-trust, relationship-driven business owners install the 90 Day CEO Operating System®, inside the kitchen-party culture you heard about in this episode.
The Matriarchy Would Never Assume You Are The Safety Net. Episode 1, where the series starts, and the safety net Racheal comes back to in the leadership section.
The Matriarchy Would Never Sell You Patriarchy in Pink. Episode 2, on business advice sold back to women in the language of empowerment.
The Matriarchy Would Never Shut Down Your Critical Thinking. Episode 3, the persuasion playbook and the line between marketing and manipulation.
The Matriarchy Would Never Leave You Out Of Your Own Business Plan. Episode 4, with the definition of success exercise Racheal refers back to in the vision section. If you haven’t done it yet, grab a pen and start there!

Connect with Me:
Instagram: @racheal.cook
TikTok: @rachealcookmba
LinkedIn: @rachealcook
YouTube: @the_ceo_collective
Website: The CEO Collective
Subscribe & Review:
If you loved this episode, please take a moment to subscribe and leave a review on Apple Podcasts!
🎤 Thanks for listening! I'll see you next week!

When you sit down to set your goals for the year or the quarter or even the month, do you make sure that YOU are in the plan too?
After years of running the 90 Day CEO Retreat, there’s one major planning mistake we see again and again. Women who invest in resourcing their businesses without blinking struggle to spend that same time, energy, and money resourcing themselves, because spending on the business reads as ambition and spending on yourself reads as indulgence.
That’s exactly why it feels impossible to actually follow through with that plan you so carefully mapped out for your business.
We tend to set big business goals and write plans for a version of ourselves that doesn’t exist. The version that has unlimited time and energy, and more importantly, the version that never has to take time off to take care of a sick kid or help your parents downsize into senior living. So when there is a glitch in the matrix, and someone else needs you to step in to handle something (because guess what – you’re the safety net for everyone else), there isn’t any buffer in the plan.
This is the episode where The Matriarchy Would Never Series shifts from deconstructing a patriarchal approach to business to building something that actually works for you and your real life – starting with redefining what success on your terms actually looks like for you. I promise you’ll want to grab a pen so you can go through this series of questions before you create your plan for 2027!
About an Hour and a Pen
What You’ll Learn in This Episode
→ Why you need to create your own definition of success by looking at your life & lifestyle, health & wellbeing, family & friendships, creativity & fun, and spirituality & connection to self (and why I don’t measure success by my business first)
→ Why I always consider the season of life and business I’m currently in, including how this actually looks in my real life day-to-day
→ Why women entrepreneurs have an easier time spending money to resource their business than spending money to make their daily life significantly easier.
→ Why I almost lost it when my husband asked me for a list to ‘help out’ – and the solution that has been a game changer both in our marriage and working together in the business.
→ How I realized that I inherited impossible standards that were making everyone in my home miserable and how relaxing those have dramatically improved my quality of life.
→ Do you know exactly how many hours you actually have in a typical week to work on your 90 Day Plan? I share exactly how many I plan for that helps me avoid putting too much on my plate.
Key Concepts from the Episode
The Engine, Not a Destination. Business is deliberately missing from the five areas of your definition of success. Ambitious women default to working all the time when the other areas are left vague, and the business outcompetes everything else because it is the only area with a clearly defined scoreboard.
If you lack a clear definition of success for your LIFE, your business will always take over because it’s the only thing you can clearly meansure!

The Season of Life & Business Is a Design Input. Before you set a goal, name the season your life and your business are in. Mine right now is teenagers getting ready to leave the nest, caregiving for my dad, and a business ramping back up after a year on cruise control while I took care of my mom.
Seasons come and go. There will be seasons where life demands more of you and business needs to adjust accordingly.

Ambition Versus Indulgence. Investing in the business feels like ambition because it promises an ROI. Investing in your own capacity reads as indulgence, so women keep adding support at work and keep none at home: no home success team, no personal success team, nothing scheduled for their health or their people.
As your business grows, you naturally resource the business with more support, more team, more systems so you can stay in your role as CEO. You need to resource your life the same way so you can spend your time and energy on what is actually important to you!

Hand Over the Category, Not the List. “How can I help? Just give me a list” hands somebody the execution and leaves you holding the planning. Hand over the whole category instead, the way dinner five nights a week (planning, shopping, and cooking) and every email from the kids’ schools now belong to Jameson.
Handing over tasks isn’t enough. Stop delegating to-do lists and start giving people OWNERSHIP over the entire category.

Plan for ONLY Seventy Percent. If your entire calendar is back-to-back, then you have no buffer to actually handle things that come up unexpectedly. Planning for just 70% means that you intentionally leave 30% buffer.
Before you plan your business, plan your life! This will help you see what capacity you actually have instead of attempting to life around your business.

Resources Mentioned
The CEO Ceiling Assessment.If you ran this exercise and something came back empty, this is where we find out why. Fifty minutes, live and free, and you score five capacity domains green, yellow, or red as we go. Tuesday, October 20 at 12pm ET, replay if you can’t be there live. 
The Get Paid Calculator. The $47 tool I mention in the life and lifestyle section. It works out what you need to pay yourself to live the life you want, then reverse engineers the revenue goal from that number, which is the right order. 
The CEO Collective®. The membership where service-based, relational business owners install the 90 Day CEO Operating System® and plan from their real capacity instead of an imaginary one. It is why Thursdays on my calendar belong to the members.
The Matriarchy Would Never: Assume You Are The Safety Net. Episode 1 of the series, on the business advice that quietly assumes somebody else is handling life at home. This episode is the build that answers it. 
The Matriarchy Would Never: Sell You Patriarchy in Pink. Episode 2, on who is selling entrepreneurship to women and the personas built to make you trust them faster. 
The Matriarchy Would Never: Shut Down Your Critical Thinking. Episode 3, on manipulative marketing tactics and the one question that tells you which side of the line a tactic is on. It ends by promising this episode. 
Connect with Me:
Instagram: @racheal.cook
TikTok: @rachealcookmba
LinkedIn: @rachealcook
YouTube: @the_ceo_collective
Website: The CEO Collective
Subscribe & Review:
If you loved this episode, please take a moment to subscribe and leave a review on Apple Podcasts!
🎤 Thanks for listening! I'll see you next week!

Robert Cialdini went undercover at used car lots, telemarketing rooms, and fundraising offices, taking notes on how compliance professionals move a person from no to yes, and he did it because he kept getting talked into buying things he did not want and wanted to know how it was being done to him. The book Influence: The Psychology of Persuasion was the result. He wrote it as a self-defense manual for regular people against manipulative sales tactics.
It barely sold. Then marketers and salespeople found it.
An entire industry picked up a book written to protect buyers and turned it into the field guide for converting them, which is how reciprocity, social proof, authority, scarcity and the rest ended up in a sales training I sat through years ago, handed over as a set of tools with the promise that once you understood them you would never struggle to sell anything again. Nobody in that room mentioned where any of it came from or the original intent Chialdini had with his work.
Understanding these principles is important for small business owners because this is how people making buying decisions. It’s still important to share deadlines. It’s important to let people know when something is almost sold out. And we all use marketing to build that know, like, and trust with potential clients.
This episode is about where the line sits between that and the manipulative marketing tactics taught right alongside it, and about the one question I run on any tactic to work out which side of the line it is on. If you have ever sat in a training, been handed a script, and felt the ICK about a tactic, that was not a money block or a mindset issue. That was data. And by the end of this episode, you’l have more clarity on how you can use these principles in a more aligned, honest, and authentic way for your business.

What You’ll Learn in This Episode
→ The book that was originally written as a consumer protection guide to help regular foks protect themselves against manipulative sales and marketing tactics – that got used against us the moment marketing and sales professionals started using it as a playbook.
→ The #1 question I use to determine how to use a principle of persuasion in an ethical and honest way.
→ Why getting the ICK over a marketing or sales tactic isn’t a money block or mindset issue – it’s essential information about how you actually want to use these tactics.
→ Why manufactured authority can be dangerous and how just being ‘a couple steps ahead’ has launched an entire industry of fake experts.
→ How I think about using real, honest urgency and scarcity (including thinking about internal vs external urgency and scarcity) within my own sales and marketing.
→ Why I don’t just focus on testimonials and case studies that are the biggest revenue wins (in fact – focusing only on revenue misses so many other incredible wins and results that my clients experience).
→ Understanding what an honest approach to using the principles of persuasion costs you up front and the long-term benefits of putting PEOPLE and relationships over short term profits.
Key Concepts from the Episode
The Self-Defense Manual, Resold as a Weapon. Cialdini wrote Influence so that regular people could recognize persuasion tactics while they were being run on them. It sold badly until marketers and salespeople found it, at which point it became the bible of the exact thing it was written to defend against.
A book meant to hand people their power back got resold as the system for taking it.

Information or Interference. Every principle in the book can be run honestly or run to shut down critical thinking, and the tactic itself will never tell you which one is happening. The question does.
Is this giving me what I need to decide, or is it making it harder to think?

The Ick Is Information. A woman says a script does not feel right to her and gets told the feeling is a money block, a mindset issue, a lack of commitment. The feeling is reading something real about the tactic, and training her out of it is the point.
Your discomfort is the only thing in that sales training nobody is being paid to sell you.

Manufactured Authority. Looking three steps ahead of someone and calling it expertise, then creating a Mess to Success entrepreneur origin story is not real authority on the subject. True expertise requires deep work and study, education, and hands on experience.
Being just 2 steps ahead is not real expertise. 

Who Absorbs the Cost of a Wrong Yes. When the tactics shut down critical thinking, the buyer carries the entire cost of the bad decision, the money and the time and a little more of her own self-trust. When they do not, the seller carries part of it, in the form of the sales she turned down on purpose.
The difference between a transaction and a relationship is who is holding the bill when the decision turns out wrong.

Resources Mentioned
The CEO Ceiling Assessment. Free live diagnostic on Tuesday, October 20 at 12pm ET, with a replay for anyone who cannot make it. Five areas where your capacity is quietly maxed out, scored green, yellow, or red, so you leave knowing which constraint is actually in your way. theceocollective.com/ceo-ceiling-assessment
Influence, by Robert Cialdini.The book at the center of this episode, written as a psychological self-defense manual for buyers and adopted by the people it was warning them about.
The principles of persuasion, explained in about ten minutes.The video Racheal promises on air as a plain-English walk through all seven.
The CEO Supper Club.Racheal’s quarterly restaurant takeover in Richmond, Virginia with a local chef, thirty women entrepreneurs, and conversation that goes further than “so what do you do?” The thirty two seats are the legitimate scarcity example in this episode. 
The CEO Collective®. The membership where service-based, relational business owners install the 90 Day CEO Operating System® and learn to sell without borrowing anybody’s pressure tactics.
The Matriarchy Would Never: Assume You Are The Safety Net.Episode 1 of the series, on the invisible labor built into almost every piece of business advice in circulation.
The Matriarchy Would Never: Sell You Patriarchy in Pink. Episode 2, on who is selling to you and the personas engineered to make you trust them faster. This episode is the companion piece on how.
FTC Endorsement Guides. The federal rules on testimonials and typical results that Racheal references in the social proof section.
 

Connect with Me:
Instagram: @racheal.cook
TikTok: @rachealcookmba
LinkedIn: @rachealcook
YouTube: @the_ceo_collective
Website: The CEO Collective
Subscribe & Review:
If you loved this episode, please take a moment to subscribe and leave a review on Apple Podcasts!
🎤 Thanks for listening! I'll see you next week!