In this special Collab Week episode of Wantrepreneur to Entrepreneur, eight founders come together to answer one deeply honest question:

Take us back to a lean season in your business. How did you get through it, and how do you prepare differently now?

Some are in a lean season right now. Some are still learning from their first one. Others have watched their busy seasons and slow seasons flip on them. It’s a wide-ranging episode about relationships, pipelines, cash, self-care, and why the best time to prepare for a lean season is before you’re in one.

For any wantrepreneur or entrepreneur wondering what to do when the pipeline goes quiet, or bracing for the next slow stretch, this episode is for you. You’ll walk away with practical ways to stay steady, stay visible, and keep building when business isn’t moving at the pace you want.

✨ What You’ll Take Away

In this episode, you’ll learn:

Why lean seasons can be financial, human, or about impact, and how self-care keeps you steady through all of them
Why doing more is the wrong instinct when cash gets tight, and how to decide what to cut before you have to
How to build relationships before you need them and use slow periods to reconnect and strengthen your processes
How to map your clients’ seasonal patterns so you can ramp up new channels before your own slow stretch
Why a single point of dependency is risky, and how low overhead buys you time to adapt
How to treat building the business as the work, even when the calendar is empty (or too full)

🎙️ Meet the Collab Week Contributors

Kacy Webster — Profit Quiver

Kacy Webster is a Business Transformation Strategist and Certified AI Consultant who helps leaders aim precisely at what matters most: people first, then technology. With 30+ years of executive leadership across higher education, workforce development, and enterprise transformation, she has held senior roles including Regional Market President, Campus Academic Dean, and Senior Director of Market Strategy & Insights for a nationally recognized assessment organization. Through Profit Quiver and The PrecisionX System, Kacy partners with leadership teams using her 12 Domains of Human-First AI Adoption, a framework that starts with culture, alignment, and readiness, not just technology.

Connect with Kacy: https://www.profitquiver.com/

Drew Dorenfest — Client Magnet CRM

Drew Dorenfest is a marketing expert who has worked with global brands such as Netflix, Apple, Warner Bros., and the NFL as a video editor. Today, through Client Magnet CRM, he helps small business owners get found online with SEO, GEO, and automation. That means more clients, more 5-star reviews, and more sales without having to create social content nonstop.

Connect with Drew: https://clientmagnetcrm.com/

Anne Gillaspie — Fix & Form

Anne Gillaspie is a global keynote speaker, truth disruptor, and creator of SHARE YOUR FEAR™, a movement making fear less scary and truth easier to tell. A 12-year entrepreneur, CEO and founder of Fix & Form Branding Firm, and host of the top-ranked OnlyFounders podcast, she’s also a brand therapist to founders and executives. Through provocative storytelling, unexpected dance, and radically human experiences, Anne helps audiences stop performing who they think they should be and start telling the truth about who they actually are.

Connect with Anne:

Rami Akeela — Nera Systems

Rami Akeela is the founder of Nera Systems, a confidential AI company that helps enterprises use AI on their most sensitive data. With 20+ years at the intersection of hardware, software, and cryptography and PhDs in electrical and computer engineering, Rami is a deep-tech builder with a record of solving problems before the market knows it has them. He previously founded DZK, the first company to build zero-knowledge proof systems.

Connect with Rami: https://nera.systems/

Heather Waisanen — Coastal Maverick

Heather Waisanen is the founder of Coastal Maverick, a woman-owned, boutique out-of-home advertising agency helping brands stand out beyond the screen. With more than a decade of experience across the client, agency, and media owner sides of advertising, she launched Coastal Maverick after being laid off from her role as a senior media planner. Now in her fourth year of entrepreneurship, Heather leads nationwide campaigns while staying deeply involved in Jacksonville’s business community. She’s a JAX Chamber Small Business Leader of the Year and a member of the inaugural 2026 Visionaries 200 class.

Connect with Heather: https://www.coastalmaverick.com/

Drew Mehta — ThinkFraction

After 20+ years in corporate, Drew Mehta founded ThinkFraction to help owner-operated businesses fix the leaks in their back-end workflows and bring AI into their day-to-day in a practical way. His approach pairs advisory with implementation and education, with no hype, to grow revenue, lower costs, and improve quality. He’s also learning to be an entrepreneur himself, and he’s in his first full year of running his own business.

Connect with Drew:

https://www.linkedin.com/in/dhroovmehta/
Website: ThinkFraction.xyz

Sara Reece — Workmind

Sara Reece is the CEO and Co-Founder of Workmind, where she helps organizations use practical, operations-first automation to eliminate friction and grow without adding headcount at the same pace. Over the last seven years, she has designed and implemented automation with organizations ranging from nonprofits and small businesses to franchise systems and Fortune 500 enterprises. Her career has spanned journalism, television broadcasting, environmental research, and technology. Sara is the author of The Practical Path to Operational Automation and has appeared on Wantrepreneur to Entrepreneur, It Starts with Joy LIVE, and Level 10 Leadership. She has also presented at The Business Show Miami and Akerman’s Global Franchising Summit in Denver.

Connect with Sara:

Mike Gross — Michael J. Gross LLC

Mike Gross is a trainer, training provider, consultant, and auditor who helps organizations make sense of ISO standards and apply them in a practical way. With over 35 years of experience, including steady growth into executive leadership roles, he focuses on building understanding through training first, then supporting organizations as they refine and improve their systems. He started Michael J. Gross LLC and Management System Certification Training Solutions about seven years ago after finishing his corporate career. As a committed solopreneur, his approach is straightforward: build on what already works, keep it practical, and leave people more capable than when he started.

Connect with Mike: https://mj-gross.com/

1595: How do you get through LEAN SEASONS in business? (COLLAB EPISODE)

Wantrepreneur to Entrepreneur | Start and Grow Your Own Business

1595: How do you get through LEAN SEASONS in business? (COLLAB EPISODE)