Sip and Scale

If you’ve ever found yourself scrubbing floors at 2 AM, juggling guest messages, and wondering if scaling your short-term rental business is even worth it…you’re not alone.

The truth? Doing everything…

A reliable cleaner can make or break your short-term rental business.

And if you've ever dealt with a no-show or a messy last-minute handoff, you know exactly what we're talking about.

In this episode …

If you’ve ever stayed up chasing a signature before check-in—or worse, bounced between five apps just to welcome one guest—you’re not alone.

In this episode of Sip & Scale, I sat down with Michael O’C…

Most founders wait too long to make their first sales hire or worse, they hire the wrong one.

In this episode of Sip & Scale, I sat down with Mafalda Johannsen, a sales hiring expert who’s worked with…

Ever feel like you’ve got more to offer than what your job title says? I sat down with Mamai, one of our amazing virtual assistants at Delegate, to talk about that exact feeling—and what happens when…

Ever feel like networking is awkward, exhausting, or just plain ineffective? You’re not alone. In this episode of Sip & Scale, I sit down with Alice Huang, a fractional COO and expert in community bu…

In this episode of Sip and Scale, I sit down with Aviv Shalgi, founder of Solar Simplified, to break down why so many startups fail, and what you can do to avoid the same fate. Aviv shares how Solar …

In today’s episode, I’m chatting with Conrad O'Connell, a digital marketing expert who’s carved out a niche in the vacation rental space. Conrad shares how he made his way from helping his father-in-…

In this episode of SIP and Scale, I sit down with Ryan Levy, co-founder and president of Fuze Technology, to unpack his journey from the early struggles of entrepreneurship to steering a company towa…

In this episode of Sip and Scale, I sit down with Gregory Laskody, who shares how an unexpected entry into real estate turned into a winning career in South Florida’s commercial market. We dive into …

In this episode of Sip and Scale, I chat with Sam Dundas, co-founder of Besty AI, about his inspiring journey from hospitality to tech. We talked about how AI is transforming guest messaging for shor…

In this episode of Sip and Scale, I had a great chat with Evan Patterson, a marketing pro with an incredible journey from gaming to digital marketing. We talked about a lot of topics, from the power …

Summary:

In this episode, Don Spafford shares how he went from corporate finance to investing in RV campgrounds and build-to-rent communities. He talks about creating passive income, scaling a real es…

In this episode of Sip & Scale, I sit down with Brian Keen, a franchising expert, to dive into how AI is reshaping the way businesses scale. We talk about my journey with Delegate Co. and how AI, alo…

In this episode of Sip & Scale, I chat with Shannon St. Val, a pro in the vacation rental world. Shannon shares her journey from consulting to property management, revealing how being process-oriente…

In this episode of "Sip & Scale," I chat with Rohit Chaparala, co-founder of Hemingway, about tackling the chaos of dental scheduling with their all-in-one platform. Rohit shares his journey from sid…

In this episode, Louie Bacaj, former senior director of engineering at Walmart, shares his inspiring journey from corporate life to successful entrepreneurship. He emphasizes the power of making smal…

Alex Shapiro, CEO of CanMonkey, shares how the company scaled its vacation rental trash solutions through technology and quality service, expanding into pool cleaning and on-demand trash removal. Ini…

Jason Lopez, VP of Sales, Marketing, and Customer Success at Jurny, shares the evolution of Jurny from property management to software. His insights highlight the importance of mentors, data-driven s…

Join Blendi Muriqi and Caroline Ramos as they discuss her journey from renting out her own property to becoming CEO of Host and Keep. Caroline shares insights on starting a side hustle, the importanc…