This week on Sideways Rain, we sit down with Darryl Appiah, a small business loan officer with CDC Small Business Finance and Momentus Capital, to break down one of the most stressful (and misunderstood) parts of building a business: getting funding.

But this isn’t just a conversation about spreadsheets and credit scores — it’s about people. Darryl shares how his team looks beyond the numbers to understand the entrepreneur behind the idea, especially for first-time founders, startups, and those stuck between bootstrapping and scaling.

From building your first financials to why you shouldn’t write everything off on your taxes, this episode is packed with insights, education, and encouragement for anyone chasing a dream with limited resources.

Key Takeaways:

• What lenders really look for (and what they don’t)

• How to prepare a business plan and projections that get attention

• Common misconceptions first-time founders have about small business loans

• Why separating personal and business finances is non-negotiable

• How to build a financial “paper trail” even if you’re just getting started

CDC Small Business Finance Loan Highlights:

• No minimum credit score

• Loans from $30,000 to $350,000

• Startups only require 5% borrower injection

• No collateral required

• 10-year term, no prepayment penalty

• Available nationwide

• Acceptable use: working capital, equipment, debt refi, tenant improvements, inventory, commercial real estate (25-year term)

📞 Contact Darryl Appiah:Loan Officer, CDC Small Business Finance / Momentus Capital📍 Based in Washington D.C., Maryland & Virginia📧 [email protected]📞 571-541-0283🌐 cdcloans.com

This week on Sideways Rain, we welcome Mary Bellettieri—events industry veteran turned self-published author. Mary opens up about her bold mid-career pivot into writing, what it really takes to bring a book to life without a publishing deal, and why chasing your dreams isn’t just for 20-somethings.

We explore the creative process, imposter syndrome, and how her professional background in events helped shape her storytelling journey. Whether you’re dreaming of writing your own book, making a career leap, or just need a shot of inspiration—this episode is for you.

📚 Check out Mary’s work:

• Website: marybellebooks.com

• Amazon: Bella Vita

• Kickstarter: Is Today Tomorrow?

• Instagram: @mary.belle.books

• TikTok: @mary.belle.books

• Illustrator's Instagram: @loubydoobie_illustrator

In this episode, Kris and J.R. break down the often-overlooked phase of startup life: what happens after you launch your MVP (Minimum Viable Product). They dive into the real challenges of raising capital without revenue, building traction, and proving market fit—not just product viability. From managing feedback loops and investor expectations to getting into the right rooms and balancing multiple roles, this conversation is packed with hard-earned lessons and actionable insights for founders navigating the "funding desert." Whether you're a first-time entrepreneur or deep into your own startup grind, this episode offers relatable advice and a dose of reality.

This week, we sit down with McKenna Dressel, Associate Director of Global Meetings & Conventions – Ophthalmology at Regeneron, to talk about her journey from chemistry and manufacturing to high-stakes global event planning. She shares how managing teams on the production floor shaped her approach to leading cross-functional meeting teams, driving decisions without formal authority, and juggling logistics on a global scale. We get into the realities of event planning—leadership without titles, managing multiple personalities, setting expectations, and why planes are her sacred space. Packed with practical advice and real talk, this is one every planner, producer, and strategic partner should hear.

Connect with McKenna on LinkedIn

In this episode of Sideways Rain, we sit down with Naomi Tucker, strategic events consultant, high-performance coach, and founder of Planners on Purpose. Naomi shares her expertise on managing stress, avoiding burnout, and finding joy in the demanding world of event planning.

We discuss the struggles of balancing perfectionism with efficiency, why self-care is critical for high performance, and how event professionals can set boundaries while still delivering top-tier service. Naomi also shares insights on leading with curiosity, managing client expectations, and why leadership mindset makes all the difference.

Whether you’re an event planner, business owner, or leader in any industry, this episode is packed with actionable insights you won’t want to miss!

Learn more about Naomi Tucker and Planners on Purpose:https://www.plannersonpurpose.com/

Recommended Reads from This Episode:

• Unreasonable Hospitality by Will Guidara: https://tinyurl.com/yckhjbwa

• Dare to Lead by Brené Brown: https://tinyurl.com/536wp6r3

• Never Split the Difference by Chris Voss: https://tinyurl.com/3epwunv8

Big news is shaking up the meetings and events industry—overnight tariffs on Canada, Mexico, and China are about to drive costs through the roof. In this episode, we break down the real impact: skyrocketing AV costs, hotel rate hikes, and catering price spikes that will hit corporate events hard. But it’s not all bad news—we’re tackling how to pivot, adapt, and outmaneuver these new challenges. If your business touches live events, travel, or hospitality, you can’t afford to miss this one.

Work-life balance. Everyone talks about it, but is it actually real when you're running a business? In this episode, J.R. and Kris break down the myth of balance, sharing their personal experiences juggling business, family, and life’s unexpected challenges.

They dive into:

• The chaos of balancing work and family—J.R. raising two daughters while leading The 180 Group, and Kris managing multiple jobs, moving states, and a flooded home.
• When work completely took over—the hardest moments and what finally forced a shift.
• Lessons on prioritization, delegation, and avoiding burnout.
• What work-life balance really looks like—and why it's more about making the right choices than achieving perfect harmony.

They don’t have it all figured out—but if you’ve ever struggled with too much work and too little time, this episode is for you.

Let us know: What’s one thing in your personal life you’ve been neglecting because of work? What’s one small change you can make this week?

In this episode of Sideways Rain, J.R. is flying solo to share his journey from rolling cables on show sites to becoming the CEO of The 180 Group.

It wasn’t a straight path—there were pivots, challenges, and a whole lot of sideways rain along the way. He’ll take you behind the scenes of:

• How J.R. started in high school working for his dad, doing the grunt work of live event production.
• The transition from producer to CEO, and the massive learning curve of managing people, systems, and finances.
• The growth of The 180 Group—from a small family business to scaling up, adjusting to industry shifts, and focusing on the pharma, medical device, and healthcare sectors.
• The constant professional development that shaped me—Vistage, books, HBS courses, and countless strategy sessions with my team.

If you’re a business owner, leader, or just someone navigating career growth, this episode is for you. Tune in for an honest look at what it takes to build something, adapt, and keep learning along the way.

In this episode ofSideways Rain, we sit down withSean Sanusi, a software engineer and tech consultant who has worked across startups, corporate innovation, and even government projects. We dive into the unpredictable world oftechnology development, from building software under tight deadlines to managing unexpected pivots and keeping up with the rapid evolution of AI.

In this episode, we cover:
🔹 The reality of software development—why things rarely go as planned
🔹 Common mistakes startups make when building tech products
🔹 The impact of AI and how entrepreneurs should prepare for what’s next
🔹 How to move from idea to execution in a way that actually works

If you’ve ever wondered how to take a tech-driven idea from concept to reality—or just want to hear war stories from the trenches of software engineering—this episode is for you.

Reach Seun on LinkedIn: https://www.linkedin.com/in/seun-sanusi-b59277140/

In this episode of Sideways Rain, we dive into the wild and unpredictable world of public relations with Joe Krasean, a PR pro with a global perspective, based in Germany and freelancing with companies like Black Unicorn PR. Whether you're a startup navigating fierce competition or a growing business trying to stand out, PR can be the difference between thriving in the storm or getting washed away.

Joe breaks down who needs PR, affordable strategies for young companies, and how to position yourself as a thought leader without breaking the bank. We also explore how PR mitigates crises, the value of authenticity, and how founders can leverage their personal stories to build credibility. Packed with actionable insights and real-world examples, this episode is a must-listen for entrepreneurs and business leaders alike.

Next week, we’ll dive into the tech side of business as we chat with Sean, the lead developer behind the WIFT app, to explore how innovation and AI are shaping the future of event tech. Stay tuned!