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/

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: @VivianKaye
• Vivian's website: VivianKaye.com
• Fractional Fundraising Network: https://www.fractionalfundraising.co/
• Vivian's business coaching: Operations coaching for entrepreneurs

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/

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 expertise

Find 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/

Ever wonder how to scale your consulting practice without a huge team or complex tech stack? In this episode, Ashley Rose from Systems Over Stress reveals how she built and manages her business using primarily Airtable and strategic automation. A self-described "systems nerd," Ashley opens up about how her ADHD diagnosis led her to create systems that work with her brain instead of against it – and ultimately helped her build a thriving consulting practice.

But here's what makes this conversation particularly valuable: Ashley isn't just sharing theory. She breaks down exactly how she uses Airtable as her "first team member," managing everything from client experience to launch tracking with just two part-time VAs. She also gets refreshingly honest about the financial reality of scaling, including a recent $43,000 business loan and her journey to more intentional business spending.

Whether you're drowning in spreadsheets or trying to figure out how to scale without sacrificing client experience, this episode offers practical insights on building systems that actually work. Ashley shares specific examples of how she automates everything from sales tracking to content management, and why the right systems can help you make better business decisions.

Highlights:

Your Systems Should Be Your First Hire - Before bringing on team members, invest in systems that can automate routine tasks and provide clear visibility into your business metrics. A good system is like having an extra team member for just $24/month.

Data-Driven Decisions Change Everything - When Ashley ignored her data and followed industry trends, her template shop made $23,000 compared to her group program's $422,000. Having clear metrics helps you make decisions based on what actually works in your business, not just what everyone else is doing.

Scale Without Sacrificing Experience - The right systems let you maintain high-touch client experiences even as you grow. From automated check-ins to progress tracking, you can use technology to enhance rather than replace personal connection.

Simple Can Be Sophisticated - Ashley manages her entire business with primarily two tools: Airtable and strategic automation. You don't need a complex tech stack to build a successful consulting practice.

Resources Mentioned:

Airtable: https://www.airtable.com/

Kit (Email Platform): https://kit.com/

Thrivecart: https://thrivecart.com/

Systems Over Stress: https://systemsoverstress.co/

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

Connect with Ashley:

Website: https://systemsoverstress.co/

Instagram: https://www.instagram.com/systemsoverstress/#

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/

"I used to hate speaking publicly and going into rooms full of people I didn't know. It was an absolute nightmare." Now Chris McMartin's superpower is building authentic connections that drive real business results.

In this episode, Chris shares her journey from dreading events to becoming a master connector, and reveals why playing small at events is costing you opportunities. She pulls back the curtain on her transformation and gives practical, actionable insights on becoming unforgettable (without feeling sleazy).

From her signature red power suits to the specific goals she sets before walking into any room, Chris breaks down how to show up authentically while driving real business results. She also tackles the exhausting reality of networking (spoiler: even extroverts need recovery time) and provides a fresh perspective on building relationships that actually convert.

Whether you're ready to uplevel your presence at in-person events or trying to figure out how to stand out authentically in a crowded space, this conversation will transform how you think about networking.

Key Takeaways:

1. Stop going to events without clear goals. Whether you want to meet 20 new people or connect with one specific person, having measurable objectives changes your results and your confidence.

2. Trying to network in spaces that don't energize you is a waste of time. Find the environments, people and conversations that light you up - those are the relationships that will drive business growth.

3. Being memorable doesn't mean being someone you're not. Whether it's a signature accessory, a conversation starter, or just your authentic way of showing up, find what works for you and own it consistently.

4. The "would you say this in person?" test is the fastest way to determine if your online networking strategy is effective. If you wouldn't walk up to someone at an event with that opener, don't use it in their DMs.

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

Connect with Chris:

LinkedIn: https://ca.linkedin.com/in/chris-mcmartin

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

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/

Resources:

Dotty Clothing: https://dotty.ca/

Cheekbone Beauty: https://www.cheekbonebeauty.com/