Madeline Reeves spent more than four hours building a custom proposal. Her company, Fearless Foundry, had already completed the client’s branding, website, and marketing launch. Now the client wanted the team to take over everything. Madeline reviewed the new scope step by step and heard no objections. Then she sent the agreement and received a startling reply: “Is this your PITA fee?”
PITA meant “pain in the ass.” Madeline’s first thought was, “Would you feel like you could say that to me if I were a man?”
In Episode 37 of She Counts, host Nancy McClelland and guest Madeline Reeves examine the complicated expectations that can arise when women work with other women. Both have experienced far more support than harm. Still, they argue that supporting women can’t mean expecting discounts, unpaid expertise, or unlimited access. Lasting generosity requires clear agreements, honest conversations, and respect for boundaries.
An unpaid invoice affects a real person
Madeline says the only clients who repeatedly pay her late or ignore invoices are women. It’s happened three or four times, and the largest unpaid balance was more than $30,000. One client received over $200,000 of work through an installment plan, then missed the final three invoices. Collections and demand letters didn’t fix it.
That loss didn’t disappear into a corporate reserve. Fearless Foundry is founder-led, and Madeline is a single mother. The money came out of her pay, bills, retirement savings, and kids’ college savings.
Madeline doesn’t claim women are worse clients. But she’s worked with early-stage, founder-funded companies with uncertain cash flow and funding. Her experience suggests a few practical safeguards:
- Ask where the project funding comes from
- Discuss the client’s budget before preparing a custom proposal
- Set firm payment terms throughout the engagement
- Get written approval for work outside the original scope
And yet, money is only one form of currency in a professional relationship.
The giver decides what counts as a gift
Nancy points out that currency also includes time, expertise, attention, advocacy, introductions, access, and reputation. Each has value, even when an invoice isn’t involved. “The person giving decides what’s a gift,” Nancy explains. “The recipient doesn’t get to decide that for her.”
Madeline demonstrated that kind of freely chosen generosity in 2019. Frustrated that accounting conferences kept featuring the same 10 to 15 men in a profession made up mostly of women, she created a speaker directory called “Women Talk Money”, which later became “We Talk Money”. She offered weekly coaching and monthly training without earning a dollar from the project. Eventually, she had to stop because she couldn’t keep funding it while supporting her family.
That volunteer effort was her choice. Client work involving two-to-six team members, contracted deliverables, payroll, and cash-flow forecasts was different. Recognizing that difference, again,starts with an honest conversation.
Saying the words prevents resentment
Nancy described preparing to negotiate with a close friend whose project price was much higher than expected. She knew that silently accepting the price and becoming resentful later would damage the relationship.
Madeline recently faced the other side of that situation. A colleague she’d known for more than five years needed a higher rate than her team had budgeted. Her chest tightened when he asked to talk, but she called him. He apologized for not explaining his requirements earlier, and they found a way forward. As Madeline puts it, “We’re firm on our value. We’re flexible on our timeframes.”
Useful ways to begin these conversations include:
- “What’s the ballpark we’re playing in?”
- “That’s beyond our budget. Is there a smaller scope?”
- “Something changed. Can we extend the payment schedule?”
Madeline also requires every job candidate to negotiate something because negotiation is, at its core, a communication skill. That skill also helps us distinguish fair negotiation from financial pressure.
Your bank account isn’t a limiting belief
A friend once asked Madeline to evaluate a $25,000 mastermind program. The friend was at a low point and couldn’t afford it. Instead of respecting that limit, the program directed her to a financing company that charged interest. Other programs use similar pressure, suggesting that clients use credit cards or overcome their supposed mindset problems.
“Your bank account is not a limiting belief,” Madeline confirms. Warning signs include:
- Pushing past a stated financial or personal boundary
- Treating reasonable discomfort as a mindset failure
- Encouraging debt instead of offering a smaller option
- Delivering something different from what was promised
Madeline experienced that final problem herself. She joined a six-month program costing $2,000 to $2,500 per month. It was presented as live coaching with the program leader, but Madeline received prerecorded videos and access to other coaches instead. The profitability lessons also promoted outsourcing labor for $5 or $10 an hour. After paying $6,000, she canceled because the program wasn’t delivering on its promise.
The same respect for boundaries should guide everyday requests for professional help.
Ask before assuming someone has capacity
Madeline is often happy to give someone 30 minutes or an hour. Repeated requests, however, become coaching, and coaching is paid work. One former client handles this by asking, “Does this fall within the bounds of coaching? Is this okay? Do you have the capacity for this?”
Introductions deserve the same care. Rather than copying two people on an email and creating an instant obligation, ask whether both people want the connection. Capacity also changes. During a divorce, multiple moves, parenting demands, and a struggle to stabilize her company, Madeline had to say no more often. That didn’t make her less generous… She was being honest about what she could give.
For accountants, bookkeepers, and tax professionals, it’s essential to discuss budgets early, put payment and scope terms in writing, ask before requesting unpaid expertise, and treat “no” as a complete answer. These choices may feel small, but they shape the culture we create together.
Nancy closes the episode with a reminder from Adrienne Maree Brown: “What we practice at the small scale sets the patterns for the whole system.”
Listen to the full episode to hear the rest of the conversation about protecting generosity without turning it into entitlement.