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 mad...

"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&ap...

"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...

"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 p...

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...

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 inst...

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-minut...

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 ma...

"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 op...

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 jou...

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&qu...

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 re...

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...

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 open...

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 201...

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 again...

"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...

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 d...

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...

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 sha...

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...

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...

In this episode of the Confessions Podcast, we sat down with Racheli Edelkopf, the mastermind behind Pedal Marketing - a consulting biz that helps nonprofits up their marketing game. Racheli talked about her journey as a program director and how that led her to start her own business. Racheli has valuable insights into the realm of marketing and specifically attraction-based  marketing, which is t...

Building a thriving consulting business can be a challenge, but what if the key to success lies in embracing joy and redefining growth? Meena Das, CEO of Namaste Data, shares her refreshing "anti-capitalistic" approach to building a thriving consulting practice. She emphasizes the importance of finding joy in your work, redefining growth on your own terms, and utilizing AI tools strategi...

In this episode of we're rolling out the red carpet for 'Layne, the Auctionista.'' Layne is a master of the gala stage. They shared serious confessions about the thrilling yet demanding live fundraising world. Or should we say, philanthrotaining. Yes, you read that right! Now - think for a minute - if you’re business was centered around taking the stage at live fundraising even...