Masters of Moments

In this discussion, Ben Wolff, co-founder of Onera, shares insights from his journey in the unique stays industry, highlighting his experience developing a treehouse hotel in Texas. He unpacks the financial intricacies of his latest resort investment deal, emphasizing the importance of solid operating models and performance metrics. The conversation also delves into innovative fundraising techniques and strategies for attracting high-end guests while maintaining streamlined operations in the competitive Texas Hill Country market.

Oxford Capital Group is an award-winning international real estate investment, development, asset, and property management firm. Oxford Hotels and Resorts, LLC is its wholly owned hotel operating affiliate, which specializes in operating, managing, and branding distinctive, high-design lifestyle hotels, and food & beverage venues.John is also the Founder, Chairman, and CEO of its primary hotel operating affiliate, Oxford Hotels and Resorts, LLC., which specializes in operating, managing, and branding distinctive, high-design luxury lifestyle hotels and food & beverage venues including its proprietary lifestyle hospitality brands: Godfrey, LondonHouse, Julian, IO, ALK, SOMA House, Fiona, and GarrettOn this episode, Jake and John discuss:- Navigating economic black swan events- How John Built Oxford Capital Group- How Oxford operates in the luxury lifestyle hotel spaceLinks:Oxford Capital Group, LLC - https://www.oxford-capital.com/Oxford Hotels & Resorts, LLC - https://ohrllc.com/Connect & Invest with Jake:Follow Jake on Twitter: https://twitter.com/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8PwoTopics:(00:00:00) - Intro(00:02:32) - John’s RE career(00:08:05) - European mindsets in RE investing(00:16:53) - Black Swan event insights(00:31:16) - How are you thinking about making investments in markets that might be suffering politically in the short term?(00:44:51) - Building Luxury-lifestyle brands(00:51:04) - F&B mistakes(00:56:44) - The London House Chicago(01:05:39) - How do you reconcile challenges with losing management contracts or an investor’s desire to sell?(01:10:16) - How do you structure the organization?(01:12:46) - Are you opportunistic or strategy-driven?(01:15:39) - What are some key learnings from building this company?(01:21:50) - What is your favorite hotel?

As the Co-Founder and Co-CEO of BH3, Mr. Freedman oversees Investments, Financial Analysis, and Capital Markets across all BH3 transactions, and has expertise in financial analysis, credit, and underwriting. Before cofounding BH3, Mr. Freedman was a principal in a private lending company based in South Florida that financed bridge loans on commercial and residential real estate and oversaw capital markets relationships, loan/special servicing, and workouts.On this episode, Jake and Greg discuss: How to identify A-Players The best way to comp people in REPE Organization-defining deals Capital structures Links:BH3 ManagementGreg on LinkedInConnect & Invest with Jake:Follow Jake on Twitter: https://twitter.com/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8PwoTopics:(00:00:00) - Intro(00:02:48) - Greg’s career and background(00:14:41) - How to identify A-players(00:16:43) - What’s the best way to comp people in REPE?(00:19:47) - Recruiting talent(00:23:20) - Being both entrepreneurial and institutional(00:28:40) - Organization-defining deals(00:41:10) - The world of South Florida condo development (01:00:26) - Developing relationships(01:05:00) - Capitalizing deals(01:17:34) - Waterfall structures(01:22:16) - Buying debt(01:27:41) - What is your favorite hotel?

Chris Pronger is a former NHL MVP who played 19 years in the league before embarking on his journey into entrepreneurship with his adult beverage business.JRNY is a Canadian whisky created by the Brothers Sean and Chris Pronger with award-winning distillery Niagara Falls Craft Distillers Whisky. On this episode, Jake and Chris discuss:- Life in the NHL, mistakes, and lessons learned- Developing a professional mindset in athletics and business- Launching JRNY and competing in the beverage marketCheck out JRNY here: https://jrnyspirits.com/Topics:(00:00:00) - Intro(00:04:34) - How youth sports have changed(00:09:44) - Developing a professional mindset in athletics(00:12:01) - Misconceptions about leadership in pro sports(00:14:36) - What it takes to play 19 years in the NHL(00:16:37) - Transitioning back to civilian life(00:19:18) - Mentors & investing(00:33:32) - Discovering yourself after retiring(00:39:27) - Launching a whiskey brand(00:52:02) - Bouncing back from failure(00:53:24) - How to pick great partners in business(00:58:51) - Competitive advantages(01:01:17) - Brand inspirations(01:06:32) - Building relationships(01:08:57) - Chris’ real estate strategy & career reflections(01:24:56) - What is your favorite hotel?Connect & Invest with Jake:Follow Jake on Twitter: https://twitter.com/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Exploring Mark Brugger's journey in hotel real estate investing, learning from Marriott, transitioning to leisure assets, challenges of remote acquisitions, and the significance of off-market transactions in the hospitality industry.

Isaac French talks about crafting micro-resorts, selling Live Oak Lake for $1M per key, and founding Experiential Hospitality. Topics include building Live Oak Lake, naivety as an advantage, and future plans in the hospitality business.

In this podcast, Avi Brosh discusses his career in hospitality and Pali's approach to design. They talk about creating hubs for locals and transients, transitioning from residential to hospitality, and maintaining a fresh feel with each new project. Avi shares insights on mistakes made early on and the importance of brand identity in the hotel business.

Sieva Kozinsky is the Managing Partner and co-founder of Enduring Ventures, a long-term holding company dedicated to buying and building beautiful businesses and stewarding them with exceptional, values-driven leadership.On this episode, Jake and Sieva discuss: Pivoting from being an operator to an investor Due diligence on potential acquisitions How to incentivize management teams and CEOs How Enduring integrates into an acquired company Links:Sieva on XEnduring VenturesConnect & Invest with Jake:Follow Jake on Twitter: https://twitter.com/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8PwoTopics:(00:00:00) - Intro(00:03:33) - What is a holdco and why are they so popular?(00:07:20) - Sieva’s focus on private companies(00:14:54) - Pivoting from being an operator to an investor(00:17:13) - Starting Enduring(00:20:41) - How did you make UpCouncil a profitable business?(00:23:52) - VC Turnaround work(00:26:58) - What kind of due diligence are you doing to get you to a quick yes or no?(00:30:56) - How do you interview management teams to determine if they will stick around?(00:37:16) - What’s the best way to incentivize CEOs?(00:39:18) - What’s the best way to integrate Enduring into an acquisition?(00:46:10) - How do you keep a pulse on all 21 companies within Enduring?(00:49:13) - Are there any outstanding ideas or processes from a CEO within Enduring that you wanted to apply to all the companies?(00:54:20) - Do you get more energy from finding deals or making an acquisition flourish?(00:58:54) - Acquiring platforms vs. businesses(01:03:17) - The Enduring Ventures organizational structure(01:15:10) - Finding the balance for doing what’s best for an individual business and the portfolio(01:16:31) - How does the financing for doing a deal work?(01:27:10) - What scares you most about growing a business?(01:30:05) - What is your favorite hotel?

Ian Ross founded SomeraRoad in 2016, bringing a fresh, entrepreneurial approach to opportunistic real estate in growing secondary cities nationwide. He has since led the firm’s rapid expansion, overseeing nearly $2.5 billion in acquisitions of 25+ million square feet in more than 70 unique markets. Ian has also augmented SomeraRoad’s core value-add business, building new verticals in industrial net lease, distressed debt, and opportunity zone investing and creating a robust ground-up development practice. Today, SomeraRoad is arguably the fastest-growing commercial real estate investment and development company in the USA.On this episode, Jake and Ian discuss: Building SomeraRoad Micro-neighborhoods Having local expertise at a national scale Placemaking and Hospitality in Office and Hotel assets Connect & Invest with Jake:Follow Jake on Twitter: https://twitter.com/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8PwoLinks:SomeraRoadIan on LinkedInTopics:(00:00:00) - Intro(00:03:50) - Ian’s entrepreneurial journey(00:06:27) - Biggest lessons learned on someone else’s dime(00:08:37) - Do local operators tend to miss out on macro trends?(00:15:09) - Early decisions to make when considering entering a new asset class(00:20:05) - Raising capital & funds(00:28:47) - Focusing on neighborhoods instead of cities(00:31:13) - Setting up local offices(00:34:36) - How has your thoughts on placemaking changed?(00:41:45) - What’s your approach to hospitality?(00:46:23) - How much do you think about competitors in your local market?(00:50:58) - 1 Hanover Square(00:56:51) - Keeping teams interconnected and hiring, (00:59:39) - How do you keep the pulse on whether you’re hitting goals?(01:00:45) - The industrial net lease space(01:02:26) - Where do you get inspiration?(01:04:41) - What are your goals for the next 5 years?(01:05:29) - What’s been your favorite deal?(01:08:27) - What’s your favorite hotel?

Brian Rosen is the founder of the Growth Beverage collective of brands, which includes Sprout Beverage, InvestBev, BevStrat, and Algoma Capital. The Growth Beverage ecosystem serves independent beverage brands at every stage of their growth journey - from inception through exit.On this episode, Jake and Brian discuss:- Growing the family business to over $100M- The reality of Private Equity- Advice to early career folks- The 101 of what makes a great alcohol brandLinks:Brian on LinkedIn - https://www.linkedin.com/in/briandavidrosen/InvestBev - https://www.investbev.com/Connect & Invest with Jake:Follow Jake on Twitter: https://twitter.com/jwurzakTake the Hospitality Investing Masterclass: https://learn.jakewurzak.com/Learn How to Invest with DoveHill: https://bit.ly/3yg8PwoTopics:(00:00:00) - Intro(00:04:25) - Brian’s family legacy in the beverage business(00:08:15) - Taking the business to $100 million(00:10:39) - The struggles of joining a family business as the 3rd generation(00:24:20) - Selling the business to Private Equity and buying out the rest of the family(00:25:28) - Operating in a highly regulated environment(00:26:23) - Life under PE(00:30:47) - Advice to early career folks(00:32:47) - How the liquor business has changed(00:36:55) - Buying back the business(00:39:45) - InvestBev(00:41:16) - Titos: How does an overnight success take 20 years?(00:43:27) - The power of celebrity marketing in new beverage brands(00:49:10) - How do you approach investing in brands?(00:52:52) - Do you consider incubating your own brands?(00:57:00) - The distillery world(01:01:11) - Optimal hold periods of brands(01:02:34) - Raising a fund(01:12:48) - Advice for those looking to overcome a challenge in their track record(01:15:43) - How has your fund structure changed now that you’re on your fifth?(01:17:34) - What’s your competitive edge?(01:20:33) - How big is the cannabis-beverage market?(01:22:32) - What would you have preferred to do more or less of in your career?(01:25:00) - 3 year goals(01:28:48) - What’s your favorite hotel?