Worried about cash flow? You’re not alone. In this episode of The Overlap Podcast, Sid Sexton and Keith Glynn dive into the all-too-familiar anxiety of lean seasons in business—when the invoices are out but the payments aren’t in. Whether you’re a seasoned entrepreneur or a scrappy startup, they break down a practical playbook for managing the pressure, keeping your team aligned, and staying afloat without losing your mind.

From real talk on invoicing and receivables to creative ways to boost cash and retain clients, this episode is your sanity-saving guide to riding out the revenue rollercoaster with confidence.

What You’ll Learn:

• How to forecast and manage your cash flow with clarity

• The art of collecting money without burning relationships

• Why overcommunicating with your team is a leadership superpower

• Smart ways to cut expenses without hurting your business

• How to use prepayment strategies to your advantage

Key Topics Discussed:

• Sid’s Dirty Dozen method for staying on top of slow payers

• How to reduce anxiety with a 13-week cash forecast

• When to ask for deposits—and how to do it without flinching

• Why trying to “hide” your lean times can backfire with your team

• The overlooked financial danger of treating prepay money like profit

• Why selling with urgency (and collecting with intensity) is crucial during cash crunches

• How bundling services or offering prepaid discounts can fuel short-term cash and long-term loyalty

Quotes Worth Remembering:

“You are not your customer’s bank.” — Sid Sexton

“Intent has a smell—and your team can sniff out when things are off.” — Sid Sexton

“Cut fat, not muscle. Protect what keeps the engine running.” — Sid Sexton

“Your creative time has value—get the deposit.” — Keith Glynn

“Being the squeaky wheel is the most important job when times are tight.” — Sid Sexton

Sponsor Spotlight: Content Fresh – Experts in social media growth and engagement, helping businesses scale visibility by over 2,000%. Visit Content Fresh Barranco & Associates – Sid’s trusted accountant for over 7 years, offering more than tax prep—providing financial strategy and peace of mind. Visit Barranco & Associates C2 Wealth Strategies – Holistic financial planning focused on long-term success and client relationships. Visit C2 Wealth Roadmap for Growth – Online course for small service businesses ready to scale with systems and strategy. Visit Tree Business

Resources & Links:

• Learn more or connect with sponsors: overlaplife.com/sponsors

• EP175 (companion episode): The Cost of Winning – How pressure and burnout impact scaling

Conclusion: Tight cash flow doesn’t have to mean sleepless nights. With the right systems, communication, and strategy, you can weather the lean times and come out stronger. If your business feels like it’s running on fumes, this episode gives you a practical, real-world approach to getting back on solid ground—without losing your cool.

Enjoy the episode? Leave a review, share it with another business owner, and subscribe to The Overlap Podcast for more real talk and tactical tools every week.