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 investorDue diligence on potential acquisitionsHow to incentivize management teams and CEOsHow Enduring integrates into an acquired companyLinks: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 SomeraRoadMicro-neighborhoodsHaving local expertise at a national scalePlacemaking and Hospitality in Office and Hotel assetsConnect & 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?

If you raise capital or invest - this is for you. I discuss:(00:00:00) - Intro(00:04:34) - Promoted Interest(00:06:00) - What’s a waterfall?(00:08:28) - How to build a waterfall(00:15:04) - Advanced structures(00:18:59) - Nuances(00:26:44) - Crystallization(00:30:06) - How we structure our deals(00:34:34) - Mistakes we’ve made(00:38:11) - Q&ALinks:Join the CommunityThe BoardroomCasey Lynch on Masters of MomentsBen Wolff on Masters of MomentsConnect & 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

Jordan Breck has been in the real estate investment business for over 10 years and is the President and co-founder at MRP. His primary responsibilities include the structuring and analysis of investments and overseeing the company’s growth strategy. Jordan has been personally involved in over $600 Million worth of transactions.MRP Capital Group is The nation's largest owner of Walmart Shadow Centers in small-town America. Their current portfolio is comprised of nearly 2.6 million square feet across 100 properties in 26 states.On this episode, Jake and Jordan discuss:What makes a great Shadow Strip CenterMRP's portfolio and transaction activityOptimizing the acquisition processDeveloping the right culture at your companyRaising capitalLinks:MRP Capital GroupJordan on LinkedInPlacer.aiConnect & 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(00:03:46) - Jordan’s experience building a real estate company(00:08:25) - Why most folks don’t transition from being a deal shop into a real estate investment firm(00:10:35) - Shadowing Walmart strip centers(00:14:35) - What makes a great shadow strip center?(00:17:34) - Where have you found ways to gain a competitive advantage?(00:22:48) - Jordan’s portfolio and transaction activity(00:25:18) - Defining the criteria for a deal(00:31:27) - The purpose of capping the number of retailers(00:33:06) - New Supply (00:38:42) - Optimizing the acquisition process(00:42:51) - What are your long-term goals for the business?(00:46:27) - Why a REIT would be interested in something as complicated as these deals(00:50:28) - What strategies are you identifying right now?(00:59:04) - Mistakes made(01:05:37) - How to develop the right culture at your company(01:15:45) - Raising Capital(01:26:45) - What’s your favorite hotel?

Affordable Upstate is a real estate investment firm focused on redeveloping and redefining naturally occurring affordable housing in the Upstate of South Carolina. In 2017 Mario co-founded Affordable Upsate, a small real estate investment firm, at the time with 63 units, that redevelops energy-efficient, multifamily apartment units. Since 2017 we have placed over $50MM of investor equity into socially responsible, environmentally-enhanced workforce housing investments.On this episode, Mario and Jake discuss:The housing shortage in the southeastMario's work in affordable housingBuilding a vertically integrated companyRaising capital & deal structuresConnect & 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:Affordable UpstateMario on LinkedInTopics:(00:00:00) - Intro(00:03:51) - Greenville: The new Austin?(00:06:57) - The housing shortage in the southeastern United States(00:13:22) - The opportunity in Class B multifamily(00:16:09) - Mario’s work in affordable housing(00:20:47) - How are you assessing risk?(00:25:47) - Mario’s journey into real estate(00:28:10) - What advantage do you have investing in the market you live in vs. outsiders?(00:29:36) - Making the entrepreneurial leap(00:37:23) - Mario’s first deal(00:41:36) - Value add(00:43:07) - Becoming vertically integrated(00:46:09) - What innovative ways have you chosen to run the operating business?(00:49:56) - What’s a mistake you made when building the PM company?(00:52:12) - Investing through Gps & building trust with investors(00:55:41) - Deal structures(00:57:56) - Raising capital(01:01:30) - What is your competitive edge?(01:03:31) - Construction & renovations(01:08:48) - What’s your weekly work cadence?(01:10:43) - What drains your energy?(01:11:43) - What are your 3-year goals?(01:14:00) - What is your favorite hotel?