Masters of Moments

An active investor for 20 years, Jonathan has been involved in over $10 billion of real estate transactions worldwide in the hospitality, office, and residential sectors, focusing on hotels. Prior to founding EOS in 2017, he was with Northwood Investors from 2007 to 2016, where he served as a Managing Director from 2009 to 2016, overseeing the acquisition and asset management of its hotel portfolio. Jonathan oversaw the hotel investment process for Northwood Investors, which included over $940.0 million of equity.On this episode, Jake and Jonathan discuss: Finding and structuring deals Gauging risk Debt strategies Rate ceilings Strategy sessions Building a vertically integrated organization Setting incentives Links:EOS InvestorsJonathan on LinkedInGirls Like Us by Cristina AlgerThe Great Game of Business by Jack StackIsla Bella Beach ResortConnect & 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(00:02:01) - Jonathan’s career hospitality(00:05:52) - How are you finding and structuring deals?(00:10:05) - Gauging risk(00:14:18) - Succeeding in hospitality as an outsider(00:20:46) - Debt strategies(00:25:51) - Evaluating market supply(00:28:12) - Rate ceilings(00:31:50) - Why Jonathan chose hospitality(00:33:49) - Most important learnings about hospitality(00:37:49) - Rationalizing having a diverse portfolio(00:45:06) - Strategy Sessions(00:50:15) - Improving communication flows(00:57:20) - Building a vertically integrated organization(01:03:17) - Building EOS(?)(01:09:01) - Incentivizing people(01:14:38) - Where investments go wrong(01:17:13) - What is your favorite hotel?

As the CEO of BTI Partners, Noah brings over 30 years of real estate finance, construction and development experience to the table with over $3.5 billion in transactions across a wide variety of asset classes.On this episode, Jake and Noah discuss:- Spotting patterns in cycles to take advantage of- Debt positioning- Identifying great locations- Biggest makes for folks getting into the land businessLinks:BTI Partners: https://btipartners.com/Noah on LinkedIn: https://www.linkedin.com/in/noah-breakstone-97ba576/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(00:01:41) - Noah’s background and career in development(00:11:31) - Spotting patterns in cycles to take advantage of(00:14:43) - Hold periods and investment horizons(00:17:02) - Asset class approach(00:22:53) - Debt positioning(00:25:49) - Finding the right partners(00:27:51) - Why did you choose to only operate in Florida?(00:31:02) - Identifying a great location(00:32:50) - Long-term concerns for Florida(00:35:37) - Build for Rent opportunities(00:41:28) - Does education play a role when looking at land?(00:44:34) - Housing(00:56:30) - The impact of distribution centers(00:59:28) - Biggest mistakes people make getting into the land business(01:05:01) - How do you know if you’re overpaying or getting a great deal?(01:07:21) - Identifying a slow-down(01:16:47) ) - How has your leadership style changed over time?(01:21:25)- What’s your favorite hotel?

Hotel industry veteran John Flannigan shares insights on becoming a GM at 26, building great hotel culture, concepting new builds, and sourcing deals. They discuss rate ceilings, doubling revenue, making a great hotel website, and the importance of building a strong hotel culture.

Scott Lewis is the co-founder and Chief Executive Officer of Spartan Investment Group, LLC (SIG). As the CEO, Scott is responsible for the strategic direction of the company and ensuring it aligns with SIG’s mission to Improve Lives Through Real Estate. Prior to Spartan, Scott held positions as a regional sales manager for a biotech firm, various positions in strategic and project management for the federal government culminating at the GS 15 level, and was on active duty in the US Army as an Infantry Officer. On this episode, Jake and Scott discuss: Leadership in the military vs. business Scaling Spartan Holding people accountable Vertical integration The Self-storage landscape Links: Spartan Storage Scott on LinkedIn No Rules Rules by Erin Meyer & Reed Hastings The Great Game of Business by Jack Stack The 4 Disciplines of Execution by Sean Covey Scaling Up by Verne Harnish Scaling up tools PDF The Conrad Thailand   Connect & Invest with Jake: Follow Jake on Twitter: https://twitter.com/jwurzak Take the Hospitality Investing Masterclass: https://learn.jakewurzak.com/ Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo   Topics: (00:00:00) - Intro (00:02:17) - Scott’s military experience (00:07:27) - Leadership in the military vs. leadership in a company (00:10:51) - Getting into real estate (00:18:01) - Scott’s first deal (00:19:31) - Scaling the business (00:29:57) - Holding people accountable (00:36:08) - Meeting structures (00:39:43) - Mistakes made early in the business (00:42:33) - Vertical integration (00:46:13) - Hold strategies (00:46:53) - Scott’s $100m deal (00:52:00) - The Spartan Fee structure (00:57:40) - The self-storage landscape (01:01:58) - Adapting to the new RE cycle (01:07:50) - Investment and underwriting processes (01:11:54) - Scott’s book recommendations (01:17:12) - Advice for inspiring performance (01:20:54) - What is your favorite hotel?

James Curnin, CEO and founder of Clara Homes, discusses risks in building spec homes, characteristics of a great contractor, reinventing luxury apartment living in Bay Harbor, and sourcing deals in Miami and Los Angeles.

Bryson is responsible for the overall strategic direction and executive management of Reaume Richardson. His knowledge was built from the ground up, as he worked in the trades for half a decade before moving into executive management. He's passionate about aligning the firm's vision, values, and targets so that Reaume Richardson can maintain the highest standards for their employees, partners, and clients. His long history in the industry and his service in the military have taught him the value of an honest day’s work and the importance of maintaining relationships, something he instills at all levels of the company. On this episode, Jake and Bryson discuss: How the construction landscape has changed over Bryson's career A walkthrough of a ground-up construction project Challenges in General Contracting Level 10 meetings and goal setting Building a development arm of the business   Links: Bryson on LinkedIn Reaume Richardson Construction The Cooperative LA The Roosevelt The St. Regis The Montage Deer Valley   Connect & Invest with Jake: Follow Jake on Twitter: https://twitter.com/jwurzak Take the Hospitality Investing Masterclass: https://learn.jakewurzak.com/ Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo   Topics: (00:00:00) Intro (00:03:07) The construction landscape over Bryson’s career (00:09:31) What are construction leaders doing to try and improve the bottom line for everyone? (00:12:01) What to know when considering Modular (00:15:03) Walkthrough of a ground-up construction project (00:17:24) Office-to-Residential conversions (00:21:06) Bryson’s background (00:28:01) Challenges in General Contracting (00:37:13) Deep dive into Pricing (00:43:49) Healthy margins to expect (00:45:24) Learnings from the GFC (00:52:54) Level 10 Meetings & goal setting (01:06:24) Building a development arm (01:22:37) What is your favorite hotel?

Sean O'Dowd built Scholastic Capital in order to buy SFR homes in elite school districts. On this episode, Jake and Sean discuss: Building Scholastic Capital Raising a fund for the business How Scholastic picks the right markets and their asset criteria Fundraising, leasing, financing, technology and more!   Links: Sean on Twitter - https://twitter.com/SeanODowd15 Sean's content and Scholastic Capital - https://linktr.ee/seanodowd Get in touch: Sean@ScholasticCapital.com   Connect & Invest with Jake: Follow Jake on Twitter: https://twitter.com/jwurzak Take the Hospitality Investing Masterclass: https://learn.jakewurzak.com/ Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo   Topics: (00:00:00) Intro (00:02:46) Sean’s career background (00:04:11) Lessons learned from Wharton and consulting (00:11:38) Applying these lessons to starting your own company (00:13:18) PE firms finding value streams (00:15:23) Building a team of A and B players (00:16:46) The decision to go into the RE business (00:19:46) Sourcing the first deal (00:23:12) The mission of Scholastic Capital (00:25:06) How to find a “good” school district (00:28:07) Supply (00:29:22) Value-add decisions (00:31:26) Requirements for a home in the right market (00:33:01) Fundraising (00:34:51) The SFR fund phenomenon (00:37:07) Future capital strategies (00:38:58) Picking a partner (00:42:04) Biggest surprises in starting the business (00:43:45) Structuring the fund (00:48:52) Facilitating monthly distributions (00:49:42) Building a team (00:52:48) Property management (00:55:10) Leasing & technology (00:59:17) The importance of the home’s age (01:00:29) Underwriting deals & what happens post close (01:06:15) Biggest challenges going forward (01:07:54) Financing (01:10:30) Target returns (01:12:44) What is your favorite hotel? (01:14:21) Twitter’s role in raising capital  

Daniel has more than forty years of specialized experience worldwide in hospitality-related: real estate appraisals, economic feasibility evaluations, investment counseling, asset management, receivership, and transactional services of hotels, resorts, conference centers, casinos, mixed-use facilities, spa & wellness properties, and timeshare/fractional ownership properties. On this episode, Jake and Daniel discuss: The Hospitality Investing environment in 2023 Approaches to underwriting deals What deals make sense as we enter a new cycle Links: LW Hospitality Advisors Daniel on LinkedIn Four Seasons Anguilla   Connect & Invest with Jake: Follow Jake on Twitter: https://twitter.com/jwurzak Take the Hospitality Investing Masterclass: https://learn.jakewurzak.com/ Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo   Topics: (00:00:00) Intro (00:02:29) Daniel’s journey into hospitality (00:07:19) What’s changed operationally and in investing over the past 40 years in hospitality? (00:09:50) What was the most impactful thing you learned from your time in Switzerland? (00:10:42) The Customer is always right (00:12:07) How do you get people comfortable with the operating side of hospitality? (00:16:29) A walkthrough of advising someone buying via auction (00:20:52) How do you think about Brand Managers? (00:22:15) What are the characteristics of a great hospitality investor? (00:24:50) What hospitality deals could be replicated as we enter a new cycle? (00:29:19) How do you view hotel REITs? (00:30:13) Are you seeing any shifts in how people are investing in hospitality? (00:34:08) What are the major considerations when underwriting a 10-year vs. 5-year hold? (00:38:05) Are you seeing shifts in new investors coming into the market? (00:40:35) What has been most surprising to you about this industry? (00:44:03) What are the most important things when owners are bringing in 3rd party management? (00:46:49) What are the most common frictions between managers and owners? (00:47:55) How do you think about investing in your assets on an ongoing basis? (00:49:54) What are you seeing in experiential hospitality? (00:53:26) Are there certain categories that you view as more challenging in experiential? (00:56:35) Tailwinds from the Pandemic & Airbnb’s shadow supply (01:02:30) If you had $100m right now, how would you deploy it? (01:06:18) What is your favorite hotel?  

Gabe has led more than $50mm of multi-family investments in metro Denver, across more than 500 apartment units in Denver, Lakewood and Aurora. Gabe is also the co-manager on over $25mm of multi-family investments (164 units) in Los Angeles. On this episode, Jake & Gabe discuss:  Going from Wall St. into Real Estate Building Generational Wealth Raising Capital Executing Value-Add Strategies   Links: Gabe on Twitter Tekton Group   Connect & Invest with Jake: Follow Jake on Twitter: https://twitter.com/jwurzak Take the Hospitality Investing Masterclass: https://learn.jakewurzak.com/ Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo   Topics: (00:00:00) Intro (00:01:48) Going from Wall St. into Real Estate (00:09:38) The desire to create generational wealth (00:11:14) Balancing raising capital while building wealth in assets (00:14:26) What are some key principles you abide by to protect you against being a forced seller? (00:20:15) Waiting for the Fat Pitch (00:25:46) Can you define sub-institutional real estate and what are some market inefficiencies you see around the asset class? (00:30:43) How do you find deals? (00:34:07) A walkthrough of a deal that closed 2 weeks later (00:39:01) How do you execute quickly on your value-add strategy? (00:43:03) What’s the structure of your fund and why did you decide to have a fund? (00:47:48) What did you learn from the first and second funds that you’ll implement in the third? (00:59:18) Have you thought about deals that you never want to sell? (01:02:28) What have you learned from your worst deal? (01:06:23) Getting tenant feedback for Capex (01:08:26) Gabe’s philosophy around 3rd party managers (01:12:15) What are your goals over the next 3 years? (01:17:12) What is your favorite hotel?

Jamal "Monster Mash" Mashburn played 12 years in the NBA and was an All-Star who averaged 19 points over his career. In his post-NBA life, Jamal has built an impressive portfolio of investments that include restaurants, car dealerships, hospitality, waste management and transportation.  In this episode, Jake and Jamal discuss: Jamal's operating portfolio Finding jockey's for businesses Jamal invests in Developing a growth mindset Underwriting, acquiring, and exiting businesses Connect & Invest with Jake: Follow Jake on Twitter: https://twitter.com/jwurzak Take the Hospitality Investing Masterclass: https://learn.jakewurzak.com/ Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo    Links: Jamal on Twitter Topics: (00:02:14) Jamal’s first inklings for entrepreneurship, playing in the NBA, and operating portfolio today (00:13:54) Doing a deal with Outback Steakhouse (00:16:28) Finding a great Jockey of a business and being part of the foundation of an investment (00:20:42) Developing a growth mindset (00:34:55) Choosing Kentucky for college (00:38:12) What are some of your major insights in your career post-NBA? (00:44:04) How do you communicate that you don’t know everything without feeling pushed around? (00:47:51) What have you learned from operating over multiple business cycles? (00:51:17) Finding success in the car business (01:00:29) How do you think about exiting a business? (01:04:23) How difficult has it been with labor in some of these businesses? (01:10:28) How do you keep a pulse on all of the businesses you’re involved in? (01:15:03) How do you underwrite a small business? (01:22:43) Are there any niche sports teams or industries that would be interesting to acquire? (01:32:51) What is your favorite hotel?