Ever roll your eyes when someone tells you AI will "revolutionize your business"? Yeah, our guest Brooke Richie-Babbage felt the same way. She was firmly in the "I don't need some tool to write weird poems" camp until one conversation completely shifted her perspective.

Now? Brooke has built an AI-powered business advisory system that's replaced expensive professional services, streamlined her financial reporting, and gives her marketing insights that used to take days to compile. And she's doing it all without becoming a tech guru or spending hours crafting perfect prompts.

In this candid conversation, Brooke pulls back the curtain on exactly how she went from AI skeptic to power user, sharing her specific systems for training custom GPTs that actually know her business, understand her clients, and deliver actionable insights she can trust.

Whether you're curious about AI but haven't found your use case yet (hi, Jess!) or you're ready to move beyond basic content creation, this episode breaks down practical applications that can actually transform how you run your consulting practice.

Highlights:

• Stop starting from scratch every time. Brooke's custom "Business Advisor" GPT is trained on 15+ business frameworks, her specific goals, and detailed customer insights—so it gives advice that's actually relevant to her business model.
• Turn raw data into actionable insights. Those monthly P&L reports and Google Analytics downloads you avoid? Brooke uploads them to AI and gets comprehensive business analysis in 15 minutes instead of spending three days doing it herself.
• Your clients need this too. The same AI systems Brooke uses for her own business are helping the nonprofit leaders she works with get strategic insights without hiring expensive consultants or drowning in spreadsheets.
• Training matters more than prompts. Forget perfect prompt architecture—the real game-changer is giving AI the right knowledge base to draw from, whether that's business frameworks, customer feedback, or your own proven methods.

Resources Mentioned:

Connect with Brooke

• LinkedIn: https://www.linkedin.com/in/brookerichiebabbage
• Brooke’s website: https://brookerichiebabbage.com/

Find Us Online: https://www.confessionswithjessandcindy.com

Connect with Cindy:

Cindy Wagman Coaching: cindywagman.com

Fractional Fundraising Network: fractionalfundraising.co/

LinkedIn: ca.linkedin.com/in/cindywagman

Connect with Jess:

Out In the Boons: outintheboons.me

LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

What do you do when the world feels like it's falling apart and you still have a business to run?

In this raw and powerful conversation, Rachel D'Souza from Gladiator Consulting opens up about navigating one of the most challenging years in recent memory. From losing a third of projected revenue when Black-led clients had funding pulled, to making the choice to double down on values instead of backing down, Rachel shares what it really looks like to lead with courage when everything feels impossible.

But this isn't just a story about surviving crisis—it's about the radical decision to choose community over competition, transparency over pretense, and love over fear. Rachel breaks down the practical strategies she's using to keep her team together, the emotional toll of leadership during unprecedented times, and why she believes "community is survival."

Whether you're struggling with how to show up authentically in your business right now, wondering if you should tone down your values to protect revenue, or just need to hear that you're not alone in feeling like the world has gone completely sideways, this conversation will remind you why doing the right thing—even when it's hard—is always worth it.

Highlights:

• Crisis reveals your true values—and that's your competitive advantage. When Rachel's business faced significant revenue loss, doubling down on equity and justice messaging didn't hurt her business—it attracted clients who specifically sought them out because they trusted Rachel's values and approach.
• Radical transparency builds stronger teams. Rachel's weekly staff meetings include discussions about cash flow, revenue projections, and the reasoning behind difficult decisions. This vulnerability has created a team culture where people proactively find solutions and support each other through challenges.
• Business development timelines are longer—plan accordingly. What used to be predictable revenue streams now require patience and relationship-building. Rachel went from knowing her full year's revenue by May to having conversations in June about work that won't start until January.
• Community over competition creates sustainable growth. Instead of hoarding opportunities, Rachel actively refers work to other values-aligned consultants and builds referral networks. This collaborative approach has created a stronger pipeline for everyone involved.
• "Enough" is a business strategy. Rachel's commitment to having "enough" rather than maximizing profit has allowed her to make decisions based on values rather than pure financial gain—from taking compensation cuts to ensure team stability to closing for three weeks every summer for rest and family time.

Resources Mentioned

Connect with Rachel:

• LinkedIn: Search for Rachel D'Souza or Gladiator Consulting
• Instagram: @gladiatorrds (for cooking content with her kids!)
• Website: gladiatorrds.com (sign up for their monthly newsletter)

Connect with Cindy:

• Cindy Wagman Coaching: cindywagman.com
• Fractional Fundraising Network: fractionalfundraising.co/
• LinkedIn: ca.linkedin.com/in/cindywagman

Connect with Jess:

• Out In the Boons: outintheboons.me
• LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

Ever feel like you're working harder but not necessarily smarter? In this candid conversation, Jess and Cindy pull back the curtain on the simple but game-changing strategies they use to stay productive, focused, and sane while building six-figure consulting businesses.

From Cindy's "CEO weeks" that give her massive chunks of uninterrupted deep work time to Jess's 90-minute screen detox that flattened her afternoon energy crashes, this episode is packed with practical hacks you can implement immediately.

Whether you're struggling with boundaries around your time, looking for ways to generate content ideas effortlessly, or just need permission to throw money at problems (hello, summer childcare!), this episode will give you the permission slip to experiment with what actually works for your life and business.

Highlights:

• Stop living in meetings if you want to grow your business. Cindy's CEO weeks—alternating between meeting-heavy weeks and deep work weeks—has been a game-changer for actually getting needle-moving work done
• The first 90 minutes of your day set the tone for everything. Jess's screen detox (no screens, no caffeine before food) eliminated her afternoon energy crashes and helped with adrenal fatigue
• Change your environment to change your energy. Sometimes the simple act of getting out of your house and walking to a different workspace can make you feel human again
• Your best business ideas won't come at your desk. Jess generates weeks of content ideas during weighted vest walks—combining exercise, inspiration, and productivity in one efficient package
• Throw money at the problems you can solve with money. From hiring summer babysitters to getting salads delivered, sometimes the best productivity hack is just paying someone else to handle it

Ready to try CEO weeks? Start with just one protected week and see what happens.

Resources Mentioned:

• Brick: https://getbrick.app/?srsltid=AfmBOoo4tU7sTn04-E9A8rU8cxTkCwCBZoPF5OLMltu9ysX44DM3F_Jc
• Diary of a CEO: https://www.youtube.com/TheDiaryOfACEO
• IFC Conference: https://www.resource-alliance.org/event/ifc-2025/

Find Us Online: https://www.confessionswithjessandcindy.com

Connect with Cindy:

Cindy Wagman Coaching: cindywagman.com

Fractional Fundraising Network: fractionalfundraising.co/

LinkedIn: ca.linkedin.com/in/cindywagman

Connect with Jess:

Out In the Boons: outintheboons.me

LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/