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/