Confessions with Jess and Cindy

It's a Wrap! Why Sometimes You Have To Kill What You Love

After hundreds of episodes and countless conversations, Jess and Cindy are making one of the hardest business decisions: ending Confessions (for now). But this isn't just a goodbye episode - it's a masterclass in strategic decision-making and knowing when to let go of something you love for the sake of your business.In this candid conversation, they pull back the curtain on how they made this decision, why "it's fun" isn't always enough of a business reason, and how regular business evaluations led them to this crossroads. From Cindy's pivot to fractional work to the reality that successful consultants still face doubt and struggle, this episode is packed with real talk about business evolution.Whether you're holding onto something in your business that's no longer serving you or wondering how to make tough strategic decisions, this conversation will give you permission to choose growth over comfort.Highlights:Regular business audits are non-negotiable. What worked 12 months ago might not align with where your business is headed today."It's fun" isn't always enough. If something doesn't serve your business goals, it might be time to let it go - even if you love it.Your business should evolve with you. Cindy's shift from general nonprofit consulting to fractional specialization shows how niching down can clarify everything.Everyone struggles, even the "successful" people. Comparison truly is the thief of joy, and behind every confident consultant is someone who still has moments of doubt.Thanks for being part of this journey with us. Keep doing the important work - the sector needs you. ❤️🎧 What's next? Connect with Jess at Building Better Together (buildingbettertogether.co) and follow Cindy's fractional work at nonprofitfractionals.com/fractureConnect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Work: nonprofitfractionals.com/fractureLinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meBuilding Better Together buildingbettertogether.co LinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

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Stop Doing What You 'Should' Do: How Rachel Muir Built a Membership Business Model Around What She Loves

Aug 2100:34:51Tap to summarize

"I was so grossed out. I would send an email and want to go hide under my bed." That's how Rachel Muir, founder of League of Extraordinary Fundraisers, describes her old high-pressure launch strategy.Now? She's built a thriving membership business around the things she actually loves doing: monthly webinars and writing emails that people think are newsletters (spoiler: they're sales emails, just really good ones).In this episode, Rachel pulls back the curtain on her complete business model transformation during COVID, when her speaking revenue disappeared overnight and she had to choose: adapt or fail. Her choice? Build around what energizes her, not what she "should" be doing.Highlights:Stop forcing yourself into marketing channels that drain you. Rachel admits she barely posts on LinkedIn and doesn't have a VA—and her business is thriving anyway.The 80/20 split that works. Rachel spends 80% of her time marketing her membership and 20% delivering—and why that ratio makes sense.How to handle the "commitment issues" of subscription pricing. People assume they're locked in for a year. Rachel's messaging strategy addresses this head-on.Why scaling isn't always the goal. With twins heading to college, Rachel's choosing travel and flexibility over aggressive growth—and that's perfectly fine.Listen to discover how letting go of the "shoulds" and building around your natural strengths can create a business that actually works for your life.Ready to ditch some business "shoulds" of your own? Subscribe to Confessions for more real talk on building a thriving consulting business.Connect with Rachel:Rachel’s website: https://www.rachelmuir.com/ Membership website: https://www.leagueofextraordinaryfundraisers.com/ Find Us Online: https://www.confessionswithjessandcindy.comConnect with Cindy:Nonprofit Fractionals Network: https://www.nonprofitfractionals.com/ LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

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Self-Employed Maternity Leave Strategy: How to Take 4 Months Off Without Losing Your Consulting Business

Aug 700:42:49Tap to summarize

"I started thinking about having a kid as it related to my career long before I even started my business. And actually it was really the impetus to start my business." What do you do when you're self-employed and need to take four months off for maternity leave? If you're Sara Royf, you get ridiculously strategic about it.Most of us panic at the thought of stepping away from our consulting businesses for any extended period. What happens to our clients? Our income? Will anyone remember we exist when we come back? Sara faced all these fears when she got pregnant, and instead of spiraling, she created a plan that actually worked.Well, mostly worked. Because this is Confessions, and we're gonna talk about the stuff that didn't go as expected, too.Sara breaks down exactly how she pre-scheduled four months of content (yes, four months), managed client expectations, and kept her audience warm while she was away. She also gets real about the maternity leave waitlist that converted exactly zero clients and why she'd completely flip her communication strategy if she did it again.But here's what makes this conversation especially valuable—Sara's not just sharing theory. As a LinkedIn coach who teaches consultants how to get clients through authentic relationship-building, she literally practices what she preaches. Her approach to LinkedIn DMs is the opposite of gross sales tactics, and it works so well that clients book discovery calls with her while simultaneously telling her they hate DMs.Plus, she drops a confession that'll surprise anyone who follows her work: she's actually not that fond of LinkedIn. Plot twist, right?Highlights:Stop trying to optimize for everything when planning extended leave. Sara chose creative outlet and audience warmth over maximum revenue, and that clarity shaped every other decision she made.The 30-person waitlist that converted zero people immediately taught her that timing in business is everything. Sometimes your best-laid plans flop, and that's totally okay if you've layered your strategies.Make more noise about coming back than going away. Sara wishes she'd spent less energy announcing her departure and more energy announcing her return—your audience cares about when you're available, not why you're not.LinkedIn DMs work when you treat them like in-person conversations. The "would you say this at a conference?" test transforms how people respond to your outreach and makes it feel authentic instead of sales-y.Even the experts doubt themselves. Sara had to constantly remind herself she'd achieved exactly what she optimized for, proving that mindset challenges hit all of us—and why having good business friends matters.Don’t miss the end of the episode to find out how you can connect with Sara and get expert feedback on your LinkedIn profile—completely free.Connect with Sara:Linkedin: https://www.linkedin.com/in/sara-royf/ Find Us Online: https://www.confessionswithjessandcindy.comConnect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

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Stop Competing, Start Differentiating: Trevor Nelson's 7-Figure Strategy

Jul 2400:42:16Tap to summarize

"I'm not gonna do it like everybody else. I'm very stubborn. I'm very competitive. I do believe that differentiation is stronger than competition."That's Trevor Nelson from HGA Fundraising, and he's built something pretty incredible by completely ignoring what his competitors were doing. While everyone else was chasing the luxury market at the "tip of the pyramid," Trevor went straight for the base – working with smaller nonprofits that everyone else was overlooking.The result? A 7-figure consignment business with 24 employees, serving thousands of events.And they're just getting started.In this episode, Trevor pulls back the curtain on his anti-competition strategy and shares why trying to beat everyone else at their own game is a losing battle. Instead, he chose to be the best at something completely different, and it's working.Highlights:Stop trying to out-compete everyone else. Trevor looked at what his competitors were doing and deliberately chose the opposite path. Sometimes the best strategy is not to play the same game.Volume can be your friend if you're not afraid of it. With thin margins and a "make a little off of a lot" model, Trevor embraces scale instead of running from it. His mindset: "All I have to do is exactly what we're doing right now, just more of it."Family business isn't a dirty word. Against all conventional wisdom, Trevor built his company by hiring his sister, brother-in-law, and best friends. His take: "Those are the people you can trust and roll with."Relationships are your real equity. Trevor's entire business model is built on genuine connections – even talking prospects out of using their services if it's not the right fit. The long game always wins.Ready to stop competing and start differentiating? This conversation will shift how you think about positioning your consulting business in a crowded market.Connect with Trevor:LinkedIn: Trevor NelsonCompany website: hgafundraising.comPodcast: "Hey Nonprofits" (YouTube, Apple, Spotify)Find Us Online: https://www.confessionswithjessandcindy.comConnect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

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The "Oh Shit" Moment: When AI Finally Clicks for Nonprofit Consultants

Jul 1000:40:56Tap to summarize

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/brookerichiebabbageBrooke’s website: https://brookerichiebabbage.com/Find Us Online: https://www.confessionswithjessandcindy.comConnect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

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When Systems Crumble: Running a Values-Based Business in a Dumpster Fire World

Jun 2600:35:34Tap to summarize

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 MentionedConnect with Rachel:LinkedIn: Search for Rachel D'Souza or Gladiator ConsultingInstagram: @gladiatorrds (for cooking content with her kids!)Website: gladiatorrds.com (sign up for their monthly newsletter)Connect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

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When You're Drowning in Your Business: 5 Simple Fixes That Actually Work

Jun 1200:42:48Tap to summarize

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 doneThe 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 fatigueChange 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 againYour 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 packageThrow 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 itReady 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.comConnect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

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From Health Crisis to Niche Success: How Dr. Tiffany Built a Virtual HR Department

May 2900:43:26Tap to summarize

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.comConnect with Dr. Tiffany:Website :https://hrtailormade.com/ LinkedIn: https://www.linkedin.com/in/tiffany-e-slater Connect with Cindy:Cindy Wagman Coaching: cindywagman.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linke

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Middle Class to Millions: Seeking more than “enough” with Shannon Brome-Ward

May 15, 202500:39:41Tap to summarize

"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/ Find Us Online: https://www.confessionswithjessandcindy.comConnect 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.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

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From $100/Month to $30K Projects: How Rachel Bearbower Completely Transformed Her Business Model

May 1, 202500:45:32Tap to summarize

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.comConnect 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.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagmanConnect with Jess:Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

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All episodes

It's a Wrap! Why Sometimes You Have To Kill What You Love

Stop Doing What You 'Should' Do: How Rachel Muir Built a Membership Business Model Around What She Loves

Self-Employed Maternity Leave Strategy: How to Take 4 Months Off Without Losing Your Consulting Business

Stop Competing, Start Differentiating: Trevor Nelson's 7-Figure Strategy

The "Oh Shit" Moment: When AI Finally Clicks for Nonprofit Consultants

When Systems Crumble: Running a Values-Based Business in a Dumpster Fire World

When You're Drowning in Your Business: 5 Simple Fixes That Actually Work

From Health Crisis to Niche Success: How Dr. Tiffany Built a Virtual HR Department

Middle Class to Millions: Seeking more than “enough” with Shannon Brome-Ward

From $100/Month to $30K Projects: How Rachel Bearbower Completely Transformed Her Business Model