Advertise on podcast: Confessions with Jess and Cindy

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/fracture Connect 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/

"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.com Connect with Cindy: Nonprofit Fractionals Network: https://www.nonprofitfractionals.com/ LinkedIn: ca.linkedin.com/in/cindywagman Connect with Jess: Out In the Boons: outintheboons.meLinkedIn: linkedin.com/in/jesscampbelloutntiheboons/

"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.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/

"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.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/

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.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 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/

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.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/  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.comFractional Fundraising Network: fractionalfundraising.co/LinkedIn: ca.linkedin.com/in/cindywagman Connect with Jess: Out In the Boons: outintheboons.meLinkedIn: 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 promisesAudience 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 firstOvercoming 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 originalityThe 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 himResources Mentioned: Fundraising Coach - Marc's blog since 2003Concord Leadership Group - Umbrella company for Marc's brandsThe Nonprofit Academy - Low-cost, CFRE-accredited training programAsk Without Fear - Marc's first book on fundraising"The Surprising Gift of Doubt" - Marc's book on leadershipGallup Strengths Finder - Marc mentioned having "Maximizer" as one of his strengthsQuadrant Three Leadership Coach Certification - Program that Marc and his wife runFind 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/

In this high-energy replay of the finale to our Fractional/Shift summit, entrepreneur Vivian Kaye (founder of KinkyCurlyYaki and operations coach) introduces us to "The Chadacity" – a mindset framework that teaches nonprofit consultants how to show up with bold confidence in their businesses. After bootstrapping a multi-million dollar business as an immigrant, college dropout, and single mother, Vivian shares how adopting just a fraction of the unapologetic confidence that mediocre “Chads” often display can transform your consulting practice. This isn't about being someone you're not – it's about stepping into the fullest, most confident version of yourself. From imposter syndrome to pricing strategy, Vivian challenges nonprofit consultants to stop playing small and start demanding what their expertise is worth. Through hilarious examples and practical advice, she demonstrates how confidence isn't something you wait for – it's something you build by taking bold action, even when (especially when) it feels uncomfortable. Highlights: Stop Questioning, Start Claiming Your Worth: Your expertise isn't a luxury – it's valuable. Vivian demonstrates how mindset shifts around money and worth are essential to scaling past six figures. "Common sense is not common – there are people who will gladly pay for what you think is simple."Take Bold Action Before You Feel Ready: The confidence muscle only develops through practice. Start with one bold move today (not tomorrow), whether that's raising your rates, adding a client even when you feel at capacity, or launching a service you've been hesitating on.The "What Would Chad Do?" Framework: When facing decisions or opportunities, ask yourself what an overconfident person would do in your situation – then do it (minus the jerk behavior). This simple reframe helps bypass self-limiting beliefs that keep consultants stuck.Take Up Space Unapologetically: Whether through your personal brand, communication style, or physical presence at events, stop minimizing yourself. Vivian notes how she intentionally wears bright colors and makes direct eye contact to be memorable in professional settings.Confidence Without Compromise: True confidence isn't about stepping on others to get ahead – it's about showing up authentically while uplifting those around you. Use your "Chadacity" to create positive impact and inspire the nonprofit community.Resources Mentioned: Connect with Vivian Kaye on Instagram: @VivianKayeVivian's website: VivianKaye.comFractional Fundraising Network: https://www.fractionalfundraising.co/ Vivian's business coaching: Operations coaching for entrepreneursFind 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/

Okay, so you know how Jess has been bugging Cindy FOREVER to host a summit? Well, she finally did it! In this fun behind-the-scenes chat, Cindy spills all the tea on her first-ever Fractional Shift Summit that absolutely crushed it with 1,400+ registrations and $24K in revenue (and yes, she's got the Airtable data to prove it — you should see how happy spreadsheet data makes her!). Cindy opens up about why she finally felt ready to "take up space" as THE fractional expert, how she convinced practically every sponsor she approached to say yes (only three said no!), and why she thinks the nonprofit world needs way more time to make decisions than those "launch in 3 days" gurus will tell you. If you've been on the fence about hosting your own signature event, this episode is your permission slip to either go all-in or wait until it feels right. As Cindy says, it's definitely a "high effort, high reward" project — but now that she's built it once, she can rinse and repeat next year with half the stress. Highlights: The moment Cindy knew she was ready to claim her spot as THE thought leader on fractional roles (and why she's glad she waited)How she crafted a "curated approach" to partnerships that made sponsors feel like they were getting the golden ticket (and they funded all her speaker fees!)Why she started promoting a full two months before launch (and why LinkedIn delivered even better than her email list)The hilarious reality of launching her Academy right when the nonprofit world was in crisis mode (and what she'll do differently next time)Her secret weapon named Christine who made the whole thing possible (because let's be real, no one does this alone!)Breaking News Alert! Jess and Cindy also drop the bomb that they're hosting in-person masterminds this year in Toronto (May 21), Boulder (August), and possibly Atlanta (October). Listen to the end for details! 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 of Confessions, Jess and Cindy chat with Caroline Danks, a UK-based fundraising consultant who runs Lark Owl with her partner. Caroline shares her journey from traditional consulting to developing multiple revenue streams, most recently transitioning her email newsletter to a monetized Substack publication called The Nest Egg. Caroline discusses how she began as a freelancer in 2016 after being made redundant, then discovered the potential of online business beyond selling time for money. After initially creating and selling online courses for several years, she faced email deliverability challenges in 2023 that prompted her to rethink her business model. This led her to Substack, where she now monetizes her weekly newsletter directly, charging £6/month or £60/year. Caroline shares her marketing strategy, focusing on LinkedIn for discovery, Substack's recommendation feature for cross-promotion with other writers, and consistently producing high-quality content that people naturally share. She also discusses her decision to retire her online courses and workshops in favor of a simpler business model that prioritizes what she truly enjoys. Key Takeaways: Monetize What You Already Love Doing: Caroline found success by turning her passion for writing emails—something she was already doing weekly—into a revenue stream. As she puts it, "there's a simplicity in being able to monetize a thing that you would be doing anyway and a thing that you probably would do if nobody paid you for it because you love it so much."Quality Content Is Your Best Marketing Tool: Caroline emphasizes that creating genuinely valuable content is central to her strategy. Each piece helps her clarify her own thinking on important topics while providing tactical advice to readers, which naturally encourages sharing and word-of-mouth growth.Simplify for Sustainability: By retiring her online courses and reducing workshops and affiliate marketing, Caroline created a more streamlined business model that reduces overwhelm and focuses on her strengths. This intentional simplification helps maintain quality while preventing burnout.Alternative Revenue Models Require Patience: Caroline is transparent about the "slow burn" nature of subscription models, noting that a low-cost product requires higher volume to be significant financially. She's comfortable with this gradual growth because it aligns with her lifestyle needs and desire for business simplicity.There's Power in a Weekly Commitment: For five years, Caroline has consistently published content every Tuesday at 10am without fail (except for planned breaks in August and December). This consistency has been crucial to building trust and a loyal audience that's willing to pay for her expertiseFind Us Online:  https://www.confessionswithjessandcindy.com Connect with Caroline: LinkedIn: Caroline Danks: https://uk.linkedin.com/in/caroline-danks-ab54b921 Substack: The Nest Egg: https://larkowl.uk/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/