Confessions with Jess and Cindy

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.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/

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.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/

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

Ashley Rose, a systems expert and ADHD advocate, shares her journey in scaling a consulting practice using just Airtable and automation. She reveals how her ADHD diagnosis inspired her to develop systems that enhance efficiency. Ashley discusses the financial realities of entrepreneurship, including her experiences with debt and decision-making. Listeners can expect practical tips on using Airtable to manage everything from client experiences to sales tracking, highlighting the importance of having a system as your first hire.

In this engaging discussion, Chris McMartin, an expert in building authentic business connections, shares her captivating journey from public speaking dread to networking mastery. She emphasizes the necessity of setting clear goals before attending events and finding energizing environments to foster genuine relationships. Chris also discusses the power of personal branding through unique styles and the transition from traditional networking to modern digital interactions. Her actionable insights will transform your approach to making unforgettable connections!

Ever wonder what it really takes to build a consulting business that aligns with your values AND makes great money? This week's guest, Rachel D'Souza, founder of Gladiator Consulting, reveals how a Netflix binge and a supportive brother helped her build a consulting business that now hovers between $750-900K in annual revenue.But here's what makes this story interesting - Rachel doesn't chase RFPs, doesn't compromise on her values, and actually turns down clients who don't align with her vision for transforming the nonprofit sector. And the surprising result? More success, not less.Rachel opens up about how she went from charging "nonprofit sector rates" to confidently pricing at $500/hour, thanks to some tough love from her business coach. She shares the mindset shifts required to charge premium rates while still ensuring her services remain accessible to grassroots organizations.We dive deep into how she structures her team (hint: it's a mix of core staff and carefully selected contractors), her approach to equitable compensation, and why she's not afraid to have hard conversations about money with potential clients.But perhaps most compelling is Rachel's candid discussion about showing up with courage in the sector, even when it means potentially losing business. She shares how being vocal about equity and justice has actually attracted more of the right clients, not fewer.Key Takeaways:1. Your pricing structure can reflect both your values and your worth. Rachel breaks down how she prices differently for different organizations while ensuring everyone on her team gets paid equitably.2. Business development doesn't have to mean constant hustling. Building authentic relationships and being selective about clients can actually lead to more sustainable growth.3. Success often means redefining what "enough" looks like. Rachel found her sweet spot isn't about maximizing revenue but about maintaining the right balance of impact and income.4. Getting comfortable with premium pricing takes practice. Start by understanding what you and your team need to thrive, then work backwards from there.Find Us Online:  https://www.confessionswithjessandcindy.comConnect with Rachel:Gladiator Consulting Website: http://www.gladiatorrds.com/ LinkedIn: https://www.linkedin.com/in/gladiatorrds/ Instagram: https://www.instagram.com/gladiatorconsulting/?hl=en 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/Resources:Rachel’s Website: www.gladiatorrds.comPurpose First Advisors :https://www.purposefirstadvisors.com

Why Was Jess’s Black Friday Bundle Such a Hit?How do you turn a seemingly overwhelming launch into a profit-packed success story? In this behind-the-scenes episode, Cindy and Jess spill the tea on Jess’s wildly successful Black Friday Bundle launch. With 35 contributors, 408 sales, and over $24,000 in profit, Jess breaks down what worked (spoiler: waitlists are game changers!) and what she'd tweak for next time. But it’s not just about the money—Jess shares how this strategy helps nonprofit consultants build email lists and collaborate effectively. From the tech challenges (opt-in overload!) to discovering sales unicorns on her list, you’ll get a transparent look at what it takes to pull off a project like this. Ready to up your marketing game? Tune in for all the juicy details, and don’t miss this blueprint for bundling success.🎧 Listen to the full episode now and take notes—you’ll want to steal these ideas!5 Key Takeaways:A Waitlist Strategy Pays Off Building anticipation with a waitlist led to double the day-one sales compared to the previous year, with a 75% conversion rate.The Power of Collaboration By partnering with 35 consultants, Jess leveraged collective networks to drive sales and list growth for everyone involved.Email Frequency is Key Sending 12 emails in 8 days helped maintain momentum and boosted conversions, proving reminders are a kindness.Opt-In Flexibility Matters Allowing customers to choose which items to opt into gave them control, balancing convenience with quality engagement.Swipe Copy Simplifies Selling Providing ready-to-use marketing materials made it easy for contributors to promote the bundle effectively.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/Resources:Brooke Richie Babbage: https://www.linkedin.com/in/bjrichiebabbage Fractional Shift Summit: https://www.nonprofitfractionals.com/ 

Ever feel like you're so busy serving clients that you never have time to work ON your business? In this episode, gathering expert Tes Cohen reveals her systematic approach to building reflection into her consulting practice. From annual "personal offsites" to monthly reset days, learn how intentional pauses can lead to better business decisions and sustainable growth. Plus, Tes shares her "confession" about finally updating her unwieldy client tracking system during one of these reflection periods—proof that sometimes we need to slow down to speed up.If you've been running your consulting business on autopilot, this conversation offers a practical roadmap for incorporating strategic reflection into your routine. Discover why taking time away from client work isn't just self-indulgent—it's essential for business growth. Learn how to structure your reflection time, what questions to ask yourself, and how to turn insights into action. Tes shares candid examples of how these practices have shaped her business evolution, from revamping basic systems to making major strategic pivots.👉 Ready to build more intentional reflection into your consulting practice? Listen now and connect with Tes at gatherbetter.co!5 Key Takeaways:Schedule Deep Work Time Block off regular time for business strategy and improvement, whether it's monthly, quarterly, or annuallyCreate Clear Structures Use consistent frameworks and questions to guide your reflection processBalance Review & Planning Look back at what's working (and what isn't) before planning future movesImplement Simple Systems Focus on manageable improvements that you'll actually maintainConnect Personal & Professional Include both business metrics and personal wellbeing in your reflection practiceFind Us Online:  https://www.confessionswithjessandcindy.comConnect with Tes:  Transformative Gatherings: http://transformativegatherings.co/ LinkedIn: https://www.linkedin.com/in/tescohen/ 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/Resources:The Art of Gathering by Priya ParkerHustle and Play PlannerCanva Google Workspace Building Better Together Community

Ever find yourself in the middle of a client project thinking "How did I end up here?" In this candid conversation, nonprofit transition specialist Naomi Hattaway shares how she learned to stop taking on work that drained her energy and started building a practice true to her expertise. From setting "riverbank boundaries" that protect your time while maintaining flexibility, to transforming her communication style with 20-minute meetings and voice messages, Naomi offers practical strategies for consultants ready to level up their business boundaries. Plus, she opens up about her journey to finally paying herself formally after 10 years in business, driven by a powerful personal mission.If you've ever struggled with saying no to work outside your zone of genius or worried about damaging relationships by setting limits, this episode is your permission slip to reshape your consulting practice. Learn why your reputation isn't built on saying yes to everything, but rather on being known for specific, high-value work that energizes you. Naomi shares actionable examples of how to communicate boundaries professionally, refer work strategically, and build a business that serves both you and your clients better.5 Key Takeaways:Define Your Lane Clearly Your reputation grows stronger when you're known for specific, focused work rather than trying to be everything to everyoneSet "Riverbank" Boundaries Think of boundaries like riverbanks—firm enough to keep things flowing but flexible enough to adapt naturallyCommunicate Limits Upfront From 20-minute meetings to asynchronous communication, set expectations early about how you work bestMake Strategic Referrals Build relationships with other consultants who can handle work outside your zone of geniusProtect Your Reputation Be intentional about which projects you take on—they shape how others talk about your workFind Us Online:  https://www.confessionswithjessandcindy.comConnect with Naomi:  Naomi’s Website:https://www.naomihattaway.com/ LinkedIn: https://linkedin.com/in/naomihattaway Podcast: https://www.naomihattaway.com/podcast 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/Resources:Hood Wellness by Tamela J. GordonHeal Your Way Forward by Prentis HemphillDiary of a CEO PodcastBuilding Better TogetherAlison Davis’ Monthly Sales Roundtables

Are you tired of superficial networking that feels more like a chore than a game-changer? In this episode, Cindy and Jess challenge the traditional "coffee chat" approach to building professional relationships, revealing how to create connections that naturally lead to business growth. They dive deep into the often-overlooked distinction between how men and women approach networking, and why combining both strategies might be the secret sauce to your success. If you've ever wondered how some consultants seem to effortlessly build thriving networks that lead to tons of business while others struggle to get beyond small talk, this episode is your roadmap to transformation. From handwritten notes that leave lasting impressions to the art of being memorable when you're not in the room, Jess and Cindy share the strategies that have helped them build six-figure consulting businesses. They also reveal why chasing "big names" might be holding you back, and how to find your true business besties who will champion your success.5 Key Takeaways:Relationship First, Business Second The most profitable networking happens when you focus on building genuine relationships rather than immediate transactions.Be Memorable Between Meetings Success isn't about how many coffee chats you schedule—it's about being the person people think of when you're not in the room.Strategic Gratitude Matters Taking time to acknowledge and appreciate your connections during "lull seasons" can lead to unexpected opportunities when you least expect them.Community Drives Revenue Building Better Together shows how combining authentic community with strategic business mindset creates powerful financial results.Find Us Online:  https://www.confessionswithjessandcindy.comConnect with Cindy:Fractional Shift Summit registration: https://www.nonprofitfractionals.com/ 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/Resources:Fractional Shift Summit Registration: nonprofitfractionals.comBuilding Better Together Community: https://buildingbettertogether.co/