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/ 

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.com

Connect 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.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:

Rachel’s Website: www.gladiatorrds.com

Purpose 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.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/

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 annually
• Create Clear Structures Use consistent frameworks and questions to guide your reflection process
• Balance Review & Planning Look back at what's working (and what isn't) before planning future moves
• Implement Simple Systems Focus on manageable improvements that you'll actually maintain
• Connect Personal & Professional Include both business metrics and personal wellbeing in your reflection practice

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

Connect with Tes:  

Transformative Gatherings: http://transformativegatherings.co/ 

LinkedIn: https://www.linkedin.com/in/tescohen/ 

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:

The Art of Gathering by Priya Parker

Hustle and Play Planner

Canva 

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 everyone
• Set "Riverbank" Boundaries Think of boundaries like riverbanks—firm enough to keep things flowing but flexible enough to adapt naturally
• Communicate Limits Upfront From 20-minute meetings to asynchronous communication, set expectations early about how you work best
• Make Strategic Referrals Build relationships with other consultants who can handle work outside your zone of genius
• Protect Your Reputation Be intentional about which projects you take on—they shape how others talk about your work

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

Connect 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.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:

Hood Wellness by Tamela J. Gordon

Heal Your Way Forward by Prentis Hemphill

Diary of a CEO Podcast

Building Better Together

Alison 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.com

Connect with Cindy:

Fractional Shift Summit registration: https://www.nonprofitfractionals.com/ 

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:

Fractional Shift Summit Registration: nonprofitfractionals.com

Building Better Together Community: https://buildingbettertogether.co/ 

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 the approach she has taken to build her business.

Highlights:

• Racheli's transition from the nonprofit sector into marketing consultancy
• Attraction-based marketing strategies
• The balance of working on your business vs. in your business
• How to leverage your strengths and find a marketing strategy that suits your abilities and business style.

Connect with Racheli Edelkopf:

Pedal Marketing:  https://www.thepedal.co/

Instagram: https://www.instagram.com/thepedal.co/?hl=en

LinkedIn:  linkedin.com/in/racheli-edelkopf-0484a81a3

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

Connect with Cindy:

Cindy Wagman Coaching https://cindywagman.com/

The Good Partnership https://www.thegoodpartnership.com/

Connect with Jess: 

Out In the Boons: https://www.outintheboons.me

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 strategically. 

If you're ready to break free from the traditional consulting mold and create a business that truly lights you up, tune in to this episode. Get ready to redefine success, embrace joy, and build a business that aligns with your values.

Key Highlights:

• Embrace joy as a driving force in your business, infusing your offerings with authentic passion to connect meaningfully with your audience.
• Redefine "growth" through an anti-capitalist lens, measuring success by your ability to sustain your desired lifestyle while centering fulfillment.
• Strategically leverage AI as a supportive tool for content ideation, social media planning, and as a logical "thought partner" voice.
• Nurture an abundance mindset by reflecting on past successes and tracking personal wins, cultivating self-trust during entrepreneurial ebbs and flows.

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

Connect with Meena:

LinkedIn: https://ca.linkedin.com/in/meenadas 

Website: https://www.namastedata.org/ 

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/jesscampbelloutintheboons/

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 events, the last few years probably have been pretty brutal. 

But Layne has navigated that and found success in this changing world.

Entertainment Meets Philanthropy: Layne, the auctionista, underscores the substantial role entertainment plays in galvanizing gala guests and maximizing fundraising efforts. They shed light on how other nonprofit service providers might integrate entertainment into their work to form deeper, more authentic connections without resorting to pressured sales pitches.

Valuing Authenticity Over Desperation: We all agree—connection beats a sales pitch any day. Layne talks authenticity and building relationships in fundraising, capturing the essence of how we too believe in connecting with our clients for success in nonprofit consulting.

Self-Care Isn't Optional: Layne shared the essential role of self-care, especially after the heightened stimulation of event fundraising. They've mastered the art of working hard, then unwinding equally hard. As consultants, it's crucial we follow suit, remembering that recovery is just as important as the grind.

Scaling with Stories: Layne candidly discusses how embracing personal storytelling, especially their experiences as a non-binary person, has enhanced their keynote speaking engagements. Their upcoming Impact Workshop focuses on gender identity and creating inclusive workspaces, which is already garnering uplifting responses and inspiring the younger generation.

Layne's episode is a masterclass in personal branding, storytelling, and authentic engagement. These are essential tools for anyone consulting!

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

Connect with Layne: 

Layne (Linkedin): linkedin.com/in/laynetheauctionista

Layne (Facebook): https://www.facebook.com/TheAuctionistaLayne 

Layne (Instagram): https://www.instagram.com/TheAuctionista 

Layne (Twitter): https://twitter.com/The_Auctionista 

Layne Talent Inc. o/a The Auctionista (Website): auctionista.ca 

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/jess-campbell-outintheboons