Sideways Rain

Season 2 kicks off with big energy as JR and Kris bring on startup and corporate attorney Pranav Gangele to talk about his sideways rain moment — leaving the comfort of Big Law to bet on himself at a smaller shop.

Pranav opens up about the golden handcuffs of guaranteed salary, the anxiety of taking risks, and the importance of support systems when the storm hits. He shares candid insights on what founders get wrong about legal work, why the billable hour is broken, and how tech is reshaping the future of law.

We also get into family life, real talk on networking, and yes — the eternal debate: corn dog vs. Pronto Pup.

Whether you’re a founder, a lawyer, or just someone navigating your own sideways rain, this episode is a reminder that the umbrella is often closer than you think.

In Episode 16 of Sideways Rain, JR and Kris sit down with Ben Illies, Senior Manager of Events at Polygon Labs, to talk about what it really means to build events inside an industry that’s constantly shifting.

Ben reflects on his move from leading shows at The 180 Group—including time in the pharma space—to the wild, unpredictable world of blockchain and Web3. What he found was a different pace, a different kind of audience, and a whole new way of measuring success.

This episode is a deep dive into:

• The volatility of tech budgets—and how to stay grounded when everything changes overnight

• What it means to produce with purpose and how to create real impact for the communities you serve

• The surprising differences between traditional corporate events and blockchain activations

• Why soft skills, flexibility, and empathy are the real power tools in today’s events landscape

• How Ben has kept evolving his mindset while staying true to what he learned in his early days at 180

Whether you're navigating a career pivot, trying to find stability in chaos, or just wondering what blockchain events actually look like—this one’s packed with perspective, humility, and a few laughs along the way.

#SidewaysRain #EventProduction #Web3Events #PolygonLabs #CareerPivots #StartupLife #PharmaVsBlockchain #EventProfs

How do you market a product that isn’t done yet—without misleading your audience or giving your competitors a head start? In this episode, JR and Kris get honest about what it means to market WIFT while still deep in development. They talk through the tension between transparency and strategy, the lessons they’ve learned from over-sharing, and why marketing early (with care) is essential. Whether you’re building tech or launching anything new, this one’s for the builders navigating the unknown.

In Episode 14 of Sideways Rain, JR and Kris sit down with product manager Kenny Corum (formerly of Axios, now at Oura) to unpack the reality of working in product—and what it really takes to break in.

From walking away from a steady job to building trust with skeptical customers, Kenny shares the twists, pivots, and risks that shaped his journey. They dive deep into the importance of listening, honest feedback, scope creep, and how customer success skills can become the backbone of a great product career.

Whether you’re in tech, building a startup, or just figuring out your next move, this one’s for you.

Topics include:

• Why Kenny quit without another job—and what happened next
• Product management vs. customer success
• The power of listening and honest user feedback
• Dealing with ambiguity, scope creep, and tough pivots
• What makes a great PM (and why it’s not what you think)
• Lessons from building WIFT, Oura Ring, and beyond

Links:

• Email: [email protected]
• LinkedIn: https://www.linkedin.com/in/kenny-corum
• Product Podcast: https://podcasts.apple.com/us/podcast/the-product-podcast/id1219400787
• Oura: https://ouraring.com/
• Lucky Buns: https://www.luckybuns.com/location/union-market-location-lucky-buns/

On Episode 13 of Sideways Rain, JR and Kris sit down for a raw, reflective, and at times surprising look back at the two-year journey of building WIFT—from a casual birthday-day LinkedIn message to beta pilots, tough pivots, missed timelines, surprise wins, and the resilience it takes to keep going.

They talk about what sparked the idea, the decision to go with a barber-recommended developer (yes, really), the highs of IMEX 2024, the sting of rejection from a major player, and why humility, patience, and persistence matter more than any pitch deck.

This one’s for anyone who's ever tried to build something from scratch—and kept going even when the shine wore off.

Topics covered:

• How WIFT started (and why it wasn’t supposed to be a tech company)

• Choosing the right partners (and what makes someone trustworthy)

• MVP missteps and how much it really costs

• The power of listening to your market

• Learning to celebrate wins—without getting too comfortable

In this special episode of Sideways Rain, we step away from entrepreneurship and tech to focus on producing with heart.

Recorded onsite at the Make-A-Wish Minnesota Wish Ball, JR sits down with Sydney Long, graphics producer at The 180 Group and sibling of a former Wish Kid, to talk about what it means to create an event that hits close to home.

Sydney shares their family’s Make-A-Wish story, the full-circle journey of giving back, and how personal connection can elevate not just the work, but the entire purpose behind it. Together, they explore the balance between professional execution and emotional investment, and why finding meaning in your work matters more than ever.

This one’s about hope, purpose, and producing with heart. No rain today. The sun is out.

Connect with Sydney on LinkedIn: https://www.linkedin.com/in/sslyy/

Donate to Make-A-Wish MN: https://wish.org/minnesota

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