Sip and Scale

Hustle works… until it doesn’t. In this episode of Sip & Scale, I sat down with Reed Hansen , CEO of MarketSurge, to talk about what actually breaks when a business starts to scale and why “working harder” quietly stops being the answer. Reed breaks down what he sees every day working with growing companies: founders grinding nonstop, marketing getting noisier instead of clearer, and teams rel...

If you’re running your business like a one-person army—doing the emails, the onboarding, the follow-ups, the hiring, the fires, the midnight “urgent” messages—you already know the truth: You’re not running your business. Your business is running you. In this special Thanksgiving episode of Sip & Scale , I sat down with two of the people who keep Delegate running behind the scenes every single...

Ever find yourself spending hours on work you know someone else could do—yet you still do it anyway? I’ve been there, and so has my guest, Ben Coleman . In this episode of Sip & Scale, Ben opens up about how he went from doing everything himself—marketing, guest messaging, operations—to finally realizing that delegation wasn’t optional if he wanted to grow. We dig into how he built a system th...

If you’ve ever thought “I’m the only one who can do this right” —this episode is for you. I sat down with Leslie Sonnier , founder of Cortiva Collections , who shared her raw story of trying to do everything herself while growing her short-term rental business. Leslie believed no one could run things the way she did…until 80-hour workweeks and burnout forced her to face reality. We talked about th...

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 yourself feels cheaper… until it costs you your time, your energy, and your ability to actually grow. In this episode of Sip & Scale, I sat down with Mariam Avetisyan , Airbnb Host and Co-Founder...

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 of Sip & Scale , I sat down with Cristina Vascil , Director of Partnerships at Turno, to unpack one of the biggest bottlenecks STR hosts face when trying to grow: cleaning. We talk abou...

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’Connell , founder of Happy Guest , to talk about the real headaches behind guest management—and how short-term rental hosts can stop doing everything manually and actually scale their operations w...

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 early-stage startups across Europe and the US. We talked about why founders struggle with sales (especially if they’re product people), the top mistakes made in the hiring process, and why grea...

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 you finally get the chance to step up and show what you’re really capable of. In this episode, we unpack what it’s like to go from a structured corporate job to the unpredictable, fast-moving world o...

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 building, to break down how to make networking work for you, even if you hate it. Alice shares her journey from Vancouver to Austin and how she’s built thriving communities by focusing on real, mea...

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 Simplified is flipping the traditional solar model on its head, the biggest challenges in customer education, and how data-driven decision-making is the key to business growth. We also dive into mar...

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-law’s fishing charter business to building a thriving agency that specializes in marketing vacation rentals. We dive into what makes promoting vacation properties different from traditional busin...

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 toward global expansion. Ryan shares the hard-earned lessons from fundraising, navigating COVID-19’s curveballs, and building a strong team culture. Whether you're a founder, an aspiring entrepreneu...

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 everything from real estate cycles to tech’s role in the industry—and even how giving back has been a game-changer for him. Takeaways: Gregory’s start in real estate was unexpected but ultimately tra...

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 short-term rentals and the key strategies behind scaling a successful startup. Takeaways: Sam’s shift from hospitality to founding Besty AI Besty AI automates guest communication for short-term rentals W...

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 of personal branding and how to really make LinkedIn work for you, to the differences between sales and marketing (which people often confuse). If you’re in a startup or looking to connect with influen...

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 estate business, and finding unique opportunities for high returns. Don also dives into building a team and the importance of staying open to new ideas. Takeaways: Focus on creating passive income strea...

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, along with effective delegation, is helping companies streamline operations and grow faster. We also explore the future of AI, the role of remote staffing, and why adapting to these changes is key fo...

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-oriented and delegating tasks to overseas talent has fueled her success. We dive into her strategies for empowering remote teams, managing multiple properties, and the importance of networking and quality...

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 side projects to leading a Y Combinator-backed startup, emphasizing the importance of understanding customer needs and integrating feedback. Tune in to discover how Hemingway is revolutioni...

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 small bets, diversifying income streams, and building a loyal audience through valuable content and authentic connections. Takeaways: Transitioning from a nine-to-five job to entrepreneurship requires ris...

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. Initially growing via word of mouth, CanMonkey overcame hiring challenges and improved customer service by transitioning from virtual assistants to in-house support. Takeaways: CanMonkey started as a sol...

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 sales, and effective marketing strategies. Jason also discusses leveraging overseas talent, developing a strong company culture, and balancing business with family life. Highlights: Having mentors and...

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 importance of delegation, and building a strong team to scale a short-term rental business. Takeaways: Take the leap and start a side hustle while still working a full-time job Have a clear vision and plan for...

Steve Cummings , founder of Misfit Homes , transformed from graphic designer to successful Nashville short-term rental operator. His journey underscores the crucial role of streamlined operations in scaling Misfit Homes and delivering exceptional guest experiences. Highlights: Automation and AI can greatly streamline operations and marketing in the short-term rental industry. Social media marketin...