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/

In this episode, Dr. Tiffany shares how her "faith walk" led her from feeling defeated in her corporate role to building HR Tailormade, a thriving consultancy serving as the virtual HR department for nonprofit organizations. She pulls back the curtain on her seven-year journey to clarity, how health challenges became the catalyst for entrepreneurship, and why it took finding the right marketing partner to finally get her messaging right.

From structuring retainer relationships that make HR expertise accessible to small nonprofits to building strategic partnerships through intentional LinkedIn outreach, Dr. Tiffany offers a masterclass in building a consulting business that aligns with both your strengths and preferences (hello, fellow introverts!) while delivering exceptional value to clients.

Highlights:

• Define clear service boundaries in your virtual practice. Tiffany is so beautifully clear about what her virtual HR department doesn't do (recruiting and payroll) and instead builds partnerships with others who excel at those services. What a relief to know you don't have to do it all!
• Simplify your marketing as a virtual consultant. After trying ALL the platforms, Tiffany realized her nonprofit clients were primarily finding her through LinkedIn and word-of-mouth. Sometimes less really is more when it comes to marketing your virtual services!
• Ask for what you need, always. As Tiffany wisely says, "a closed mouth doesn't get fed." She shows us how to request testimonials and website mentions in ways that feel comfortable and authentic - essential skills for growing a virtual practice.
• Be patient with your niche journey. It took Tiffany seven years to get completely clear on serving nonprofits as a virtual HR consultant. Business clarity emerges through experience, not perfect planning from day one.
• Build a virtual support community. I love how Tiffany intentionally reaches out to 10 LinkedIn contacts weekly, resulting in quarterly meetings with trusted peers. This business journey is too hard to do alone, especially when you're working virtually!

Resources Mentioned:

• HR Tailor Made: https://hrtailormade.com/
• Canva: https://www.canva.com/
• LinkedIn: https://www.linkedin.com/
• Women's Business Center (St. Louis area) https://www.wbdc.org/en/event/getting-to-know-the-womens-business-center-st-louis/

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

Connect with Dr. Tiffany:

• Website :https://hrtailormade.com/
• LinkedIn: https://www.linkedin.com/in/tiffany-e-slater

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: linke

"I'm gunning this year to get to double digit millions."

That's not something you hear every day. But Shannon Brome-Ward isn't just any financial coach. As a money mindset coach and financial educator, Shannon is on a mission to help consultants move from middle class to millions, and she's not shy about her own financial goals.

In this candid conversation, Shannon opens up about the mindset shifts required for consultants to build real wealth. She challenges the scarcity thinking that keeps so many of us (especially women) playing small with our pricing and financial goals. From explaining why "getting by" is no way to live, to breaking down exactly how to start investing with as little as $25 a month, Shannon brings practical strategies any consultant can implement immediately.

If you've ever caught yourself whispering about wanting more money or felt guilty about charging premium rates while serving nonprofits, this episode is your permission slip to think bigger. Shannon walks us through how creating multiple revenue streams can provide the freedom to weather economic storms, and why having millions isn't about luxury—it's about options.

Highlights:

• Women and money shame is real. Shannon reveals why female consultants often whisper about wanting more money, while men never express concern about being "too greedy"—and how to overcome this limiting belief.
• Millionaires have multiple paychecks. Learn why diversifying your income beyond your consulting business is critical for building generational wealth, and practical examples of revenue streams to consider.
• Starting expert to build wealth.
• Charge more, live on less. The simplest wealth-building equation: increase your consulting rates while becoming comfortable living on less than you make, and invest the difference.

Resources Mentioned:

• Podcast - From Middle Class to Millions: https://podcasts.apple.com/ca/podcast/from-middle-class-to-millions/id1781017144
• Website: https://www.thewholebudget.com/
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Find Us Online: https://www.confessionswithjessandcindy.com

Connect with Shannon:

• Instagram: https://www.instagram.com/thewholebudget/reels/
• TikTok: https://www.tiktok.com/@thewholebudget
• Facebook: https://www.facebook.com/TheWholeBudget/
• Website: https://www.thewholebudget.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/

If you've ever struggled to make a profit while serving nonprofits, you're going to love this conversation. Our good friend Rachel Bearbower is back to share how she went from running a membership that was literally losing money every month to commanding $30,000+ for her automation services. And yes, she's still serving the sector we all love!

Rachel opens up about the emotional journey of letting go of her Small Shop Strategies membership (it took her over a year to fully grieve it) and the scary but exhilarating process of building the Nonprofit Automation Agency through pure trial and error. In classic Rachel fashion, she doesn't hold back about the messiness - including the website crash mid-pitch webinar that accidentally led to creating a second business!

I'm still blown away by her transformation. The Rachel who once fought for every $100 membership fee now confidently tells prospective clients on sales calls: "We are very good at what we do" - and they believe her. And they should! She's gone from barely covering expenses to making more in two months than she did in all of 2023.

Highlights:

• Done-for-you is a game-changer. Rachel realized that nonprofit leaders don't want to learn automation - they just want someone to handle the "hot mess of tech" for them. And they'll pay premium prices for it!
• Real talk on following up. Rachel followed up with one prospect for 109 days before they signed. Her secret? She BCCs herself on every proposal email, then snoozes it weekly as a reminder to check in. Don't assume silence means "no"!
• Your referral network is gold. A whopping 44% of Rachel's revenue comes from referrals. She pays 10% commission to fellow consultants who send clients her way - making it a win-win for everyone.
• It's okay to not have it all figured out. Rachel built this incredibly successful business by flying the plane while building it - no grand strategy, just constant iteration based on what worked with real clients.

Resources Mentioned:

• Nonprofit Automation Agency: https://www.nonprofitautomationagency.com/
• Kit (formerly ConvertKit): https://kit.com/?gad_source=1
• "Letters to Randy": http://letterstorandy.com/

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

Connect with Rachel:

Website: https://www.nonprofitautomationagency.com/

Linkedin: https://www.linkedin.com/in/rachelbearbower

Instagram: https://www.instagram.com/smallshopstrategies/

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/

Marc Pitman is a DELIGHT. The CEO of Concord Leadership Group joined us to spill all the tea on what it actually takes to keep a consulting practice alive and thriving for over two decades.

Marc took us on his journey from bow-tie-wearing "Fundraising Coach" to running multiple brands under his company umbrella. And yes, we finally got him to admit the truth about "passive income" (spoiler alert: it's completely made up!).

If you've ever felt like everyone else has it figured out while you're still flying by the seat of your pants, this episode will make you feel SO MUCH BETTER. Marc's old-school approach to marketing (dude literally picks up the phone and calls people every day) combined with his willingness to evolve makes for a masterclass in consulting longevity.

Highlights:

• The "Jeremy Bearimy" approach to marketing: Marc focuses on activities he can control (like making daily phone calls) and trusts that business will come—but not in the linear, trackable way modern marketing promises
• Audience building then and now: From early blogging in 2003 to navigating today's "walled-off" social platforms, Marc shares how he's consistently adapted his approach while maintaining his core focus on serving first
• Overcoming the comparison trap: Marc explains how he stops himself from second-guessing content when he sees others covering similar topics, and how finding your unique voice matters more than originality
• The consulting long game: Even with multiple revenue streams (speaking, coaching, books, etc.), Marc shares that the goal isn't to sell the business but to be "used up" when he dies—living up to all the potential entrusted to him

Resources Mentioned:

• Fundraising Coach - Marc's blog since 2003
• Concord Leadership Group - Umbrella company for Marc's brands
• The Nonprofit Academy - Low-cost, CFRE-accredited training program
• Ask Without Fear - Marc's first book on fundraising
• "The Surprising Gift of Doubt" - Marc's book on leadership
• Gallup Strengths Finder - Marc mentioned having "Maximizer" as one of his strengths
• Quadrant Three Leadership Coach Certification - Program that Marc and his wife run

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

Connect with Marc:

Website: https://marcpitman.com/

Linkedin: https://www.linkedin.com/in/marcapitman/

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 find yourself doing work you swore you'd never do?

You're not alone! When Brittny Wilson launched her consulting business in 2021, she quickly found herself saying yes to everything – especially event planning, which was literally on her "absolutely not" list.

In this chat with our friend Brittny, she opens up about her journey from reluctant event planner to confident recruitment agency owner. The turning point? When her kids flat-out told her she wasn't "nice" during event season (ouch!) and when looking at her actual numbers showed her that what felt risky – walking away from steady event clients – was actually more profitable.

Brittny gets real about the emotional rollercoaster of pivoting her business, the game-changing moment at Jess's conference when she started introducing herself differently, and how she's navigating the feast-or-famine nature of client work. Plus, she shares the exact pricing structure that's working for her now.

Whether you're feeling stuck in work that drains you or trying to find the courage to specialize, Brittny's journey will remind you that sometimes the scariest business decisions lead to the most aligned (and profitable!) outcomes.

Highlights:

• Your gut knows when something isn't working. When Brittny's kids pointed out how stressed she became before events, it confirmed what she already felt – this work wasn't sustainable for her wellbeing.
• Saying something out loud makes it real. The confidence to call herself a "recruitment agency" came before she felt 100% ready – and that declaration helped others see her differently.
• Your pricing can protect your mission. Brittny's three-phase approach ensures clients don't skip critical elements like onboarding support – the key to her mission of keeping good people in the sector.
• Systems save sanity. Working with a systems-focused contractor and implementing Airtable automations allowed Brittny to create a repeatable process that doesn't depend solely on her.

Seasons are normal. Six clients in fall, crickets in January – Brittny reminds us that business ebbs and flows are totally normal (even when they're nerve-wracking!).

Resources Mentioned:

• Airtable - https://www.airtable.com/
• Ashley (Airtable expert) - https://systemsoverstress.co/about
• LinkedIn - https://www.linkedin.com/login
• Shannon Bowen - https://monsoonleadership.com/about/

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

Connect with Brittny:

Website: https://www.brittnywilson.com/

Linkedin: https://www.linkedin.com/in/brittnywilson/

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/