In this episode of Masters of Moments, Jake Wurzak sits down with Isaac Toledano for a wide-ranging conversation on his entrepreneurial journey, development philosophy, and deep commitment to Florida real estate. Isaac reflects on his early start in business at age 15 in Israel, how his risk appetite has evolved, and why partnerships are at the center of his approach. He offers a behind-the-scenes look at marquee deals like Fisher Island and Naples, sharing his methods for evaluating sites, structuring deals, and maintaining a lean, hands-on operation across 31 active projects. Isaac also dives into the importance of location, timing, and branding in condo development, and why he believes Florida remains the best place to live, work, and invest.

We discuss:

Isaac's primary focus centers on luxury residential properties, prime land holdings, office spaces, and mixed-use assets strategically positioned in prime locations. BH Group mitigates risk exposure by targeting large-scale, value-adding prospects within specialized markets while maximizing returns. BH Group has forged partnerships with leading real estate firms in the United States, successfully completing over 1,100 luxury residential units, with an additional 10,000 units in progress.

This episode originally released in August of 2024.

Links:

BH Group - https://www.bhgroupmiami.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

(00:02:33) - Isaac’s upbringing in Israel and career

(00:06:56) - Coming to the United States and the love for Florida

(00:12:38) - What are your partner’s perceptions of you?

(00:15:57) - How do you think about risk and diversification?

(00:17:39) - How involved are you in the deal process?

(00:20:11) - What have you learned about simplicity in complicated transactions?

(00:25:36) - A walkthrough of a condo development

(00:34:18) - Target returns & deal structures

(00:37:25) - How are you compensated for your work?

(00:39:57) - What area of Florida are you interested in investing in?

(00:42:59) - Timing construction with sales

(00:46:56) - Branding

(00:51:59) - The future of Florida

(01:00:09) - Isaac’s biggest mistake, marriage, and parenting

(01:02:41) - Negotiation

(01:05:04) - What is your favorite hotel?

Jeremy Sasson joins Jake Wurzak to unpack his obsessive, guest-first approach to hospitality and share how he’s built a thriving portfolio of restaurants without external investors or debt.

The conversation traces Jeremy’s evolution from a post-college startup grind to crafting some of Detroit’s most beloved dining experiences. He explains how design, service, and team alignment all flow from a single emotional driver: how a guest feels at every touchpoint. Jeremy also reveals how he builds restaurants through the lens of fashion, explains the overlooked costs of doing hospitality well, and offers rare insight into the operational decisions that separate great concepts from lasting brands.

We discuss:

Why every element of a restaurant must begin with how it makes guests feel

The core reasons he turned down the family real estate business to pursue hospitality

What he learned building his first restaurant with no industry experience

Why he avoids celebrity chefs and prioritizes team members who “pick him”

The importance of eliminating weak cultural fits—even when it hurts in the short term

This episode is a masterclass for anyone building hospitality experiences with purpose and longevity in mind.

Links:

Heirloom Hospitality - https://heirloomhospitality.com/

Jeremy on LinkedIn - https://www.linkedin.com/in/jeremy-sasson-a172b3195/

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:

(00:00:00) - Intro

In this solo Coaching Call episode of Masters of Moments, Jake Wurzak breaks down how to create investor reports that people actually want to read. Drawing from his experience in real estate and hospitality, Jake walks through the fundamentals of reporting with clarity, consistency, and purpose.

He shares the essential elements of an effective update, including what data to include, how to tailor content based on your relationship with investors, and how frequency and tone play a role in building trust. The episode also covers the importance of visual presentation, storytelling through numbers, and why transparency is key to long-term partnerships, especially when challenges arise.

Jake also touches on:

Balancing detailed metrics with high-level narratives

Common mistakes that turn investors off

How to use reports as a strategic communication tool

Structuring reports for quarterly, monthly, or ad hoc updates

Leveraging reports to reinforce your brand and vision

Whether you're raising capital or already managing a portfolio, this episode is a tactical guide to making your investor communication stand out.

Topics:

(00:00:00) - Intro

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

In this episode of Masters of Moments, host Jake Wurzak sits down with Greg Kennealey, CEO of Peregrine Hospitality, for an in-depth conversation on building and operating a diversified hotel platform with a focus on performance, alignment, and long-term value creation. With a career that includes time at Strategic Hotels and KSL Capital, Greg brings both institutional experience and an owner-operator mindset to the conversation.

They discuss the evolving landscape of hotel investment, from pandemic-driven shifts in demand and staffing, to the renewed importance of leisure travel, stress-testing models, and driving performance across both luxury resorts and extended-stay properties. Greg also breaks down the founding of Peregrine, their vertically integrated approach, and how alignment and talent are central to outperforming in any market cycle.

They also cover:

How the best hotel companies earned loyalty by prioritizing staff during COVID

Lessons from KSL on underwriting, capital planning, and long-term investing

The rise of experiential and independent resorts—and where they see opportunity

Why owner-operator models outperform in today’s capital environment

The critical role of KPIs like labor margin, guest satisfaction, and revenue flow

Designing phantom ownership structures to retain and reward top hotel talent

Building a culture of accountability and innovation from the ground up

This episode is a masterclass in hospitality execution, told through the lens of someone who has scaled both iconic resorts and margin-driven select-service portfolios—and believes the best teams win every time.

Links:

Peregrine Hospitality - https://www.peregrinehg.com/

Greg on LinkedIn - https://www.linkedin.com/in/greg-kennealey-946b715/

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:

(00:00:00) - Intro

(00:01:32) - Resilience and Challenges in the Hotel Industry

(00:03:12) - Investment Strategies and Stress Testing

(00:04:59) - Balancing Leisure and Corporate Travel

(00:08:21) - Operational Challenges and Innovations

(00:34:13) - The Role of Location in Hotel Success

(00:38:51) - Conviction in Hotel Investments

(00:41:07) - The Complexity of Hotel Ownership

(00:41:48) - The Owner-Operator Model

(00:44:49) - Sales Strategies and Exit Timing

(00:47:21) - Rapid Acquisition Challenges

(00:50:12) - Building an Entrepreneurial Venture

(00:54:24) - Operational Oversight and KPIs

(00:58:40) - Managing Labor Costs

(01:01:26) - Investing in Experiential Resorts

(01:09:02) - Food and Beverage Strategies

(01:15:52) - Future Goals and Favorite Hotels

In this episode of Masters of Moments, host Jake Wurzak sits down with Hunt Rose, co-founder of TruCore Investments, to dive into the business of Class B industrial real estate and what makes it one of the most resilient, overlooked asset classes in today’s market. Drawing on his experience in brokerage and acquisitions, Hunt explains how TruCore’s national platform finds value in under-managed, substitutional assets and why a fragmented ownership base presents a unique opportunity for investors with a focused strategy.

They also discuss:

The risk-adjusted appeal of Class B industrial assets in infill markets

Sourcing deals through local brokerage relationships across 150+ U.S. markets

How TruCore approaches marking rents to market with legacy tenants

The business case for converting gross leases to triple net structures

Functional criteria they use to quickly screen new acquisitions

Their “100 questions” underwriting playbook and due diligence process

Fund structure, capital raising strategy, and investor communications

This episode is a practical, inside look at how a lean team is scaling a national industrial platform by sticking to fundamentals, staying disciplined, and building trust with tenants and investors alike.

Links:

Hunt Rose on X - https://x.com/nnn_industrial

Hunt Rose on LinkedIn - https://www.linkedin.com/in/hunt-rose-9229694b/

TruCore Investments - https://trucoreinvestments.com/

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:

(00:00:00) - Intro

(00:00:38) - Landing a deal from a Podcast

(00:03:04) - Where are you investing?

(00:06:37) - Is sub-institutional scalable?

(00:09:00) - The business case for Class B Industrial

(00:13:00) - What’s the business plan when you acquire a property?

(00:15:42) - Why are rents often times below market?

(00:18:23) - Lease renewal approaches

(00:22:21) - Converting gross deals to NNN deals

(00:24:47) - Where do things go wrong on these deals

(00:27:25) - What kills a deal for you?

(00:30:30) - Making the entrepreneurial leap

(00:36:02) - How have you fine-tuned the acquisition process?

(00:38:35) - What do you do differently as an owner that the tenant would recognize?

(00:42:14) - The advantage and disadvantage of being the money from out of town

(00:45:35) - Are there any tenants you refuse to have on a property?

(00:47:54) - Holding strategies

(00:49:58) - Establishing a Fund

(00:54:09) - Raising capital

(01:03:36) - Reporting and investor relationships

(01:08:51) - What is your favorite hotel?

(01:09:55) - Get in touch with Hunt

In this episode of Masters of Moments, host Jake Wurzak sits down with Brian Harper, co-founder of 11North Partners and former CEO of RPT Realty, to discuss leadership, reinvention, and the enduring relevance of retail real estate.

With a background spanning General Growth Properties, Rouse Properties, and RPT, Brian brings decades of insight from navigating some of the most complex moments in the retail sector—including corporate bankruptcies, public-to-private transitions, and large-scale portfolio transformations.

They also discuss:

* The principles behind great retail: hospitality, curation, and community

* Lessons from navigating the GGP and RPT turnarounds

* Why physical retail is far from dead—and what’s driving its resurgence

* Building culture in public companies vs. founder-led ventures

* How personal experiences, including raising a son with autism, have shaped Brian’s leadership style

* The founding vision behind 11 North Partners and their thesis on long-term, durable retail

This episode offers a grounded, values-driven look at how great retail gets built—and the personal moments that shape the leaders behind it.

Links:

11North Partners - http://11northpartners.com/

Brian on LinkedIn - https://www.linkedin.com/in/brian-harper-5431265/

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:

(00:00:00) - Intro

(00:01:08) - Brian’s career and background

(00:12:19) - Is retail becoming un-investable?

(00:14:52) - Experience and hospitality as an opportunity to save retail

(00:16:45) - Brian’s experience at GGP and Rouse

(00:23:55) - The collapse of bad malls

(00:27:17) - Positioning malls for success

(00:37:06) - What makes a spectacular open-air center?

(00:40:36) - What retailers are picking the best locations?

(00:42:40) - What goes wrong in retail centers?

(00:44:26) - Building 11North

(01:03:01) - Raising a child with autism

(01:17:26) - What is your favorite hotel?

Channeling a passion for the hospitality industry, Mitch Patel established Vision Hospitality Group in 1997 on a foundation of values that guide the organization to this day.  

With an unwavering commitment to excellence, Mitch oversees every aspect of the company, from investment procurement to the seamless execution of daily operations. Additionally, he oversees strategic development and implementation that has propelled Vision Hospitality Group to garner numerous awards within the industry.

Links:

Visionary Hospitality Group - https://www.vhghotels.com/

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:

(00:00:00) - Intro

(00:00:55) - Mitch’s career and background in hospitality

(00:20:40) - What did you learn about risk in the early days of your company and why did you only focus on the hotel asset class?

(00:31:39) - How much do you attribute your success to your ability to develop vs. operate?

(00:39:15) - How are you able to develop 10 hotels at once?

(00:59:05) - Mitch’s passion for experiential and lifestyle hotels

(01:20:06) - What are the non-negotiables you put in independent hotels?

(01:29:54) - What concerns do you have for the future of hospitality?

(01:44:10) - What is your favorite hotel?

This episode originally aired in May of 2024

In this episode of Masters of Moments, host Jake Wurzak sits down with Micah Lacher, founder of Anchor Investments, for a deeply personal and wide-ranging conversation about real estate, entrepreneurship, and the power of second chances. From growing up in a struggling household in North Memphis to building a respected investment and development firm in Nashville, Micah’s story is both gritty and inspiring.

They begin with Micah’s early exposure to real estate, sparked by a life-changing move that took his family from an unsafe neighborhood to one of the best public school districts in Memphis—secured through an unlikely deal involving two Delta Airlines plane tickets. That experience set the tone for a life shaped by faith, hustle, and resilience.

Throughout the episode, Micah shares how he transitioned from a brokerage role at Cushman & Wakefield into real estate development, thanks to the mentorship of Bob Tull, a former Walmart developer. He recounts launching Anchor in the depths of the 2009 financial crisis, raising capital deal-by-deal to purchase distressed assets when few others had the conviction to buy.

They also discuss:

- The high-stakes risk of personal guarantees during the Great Financial Crisis  

- How Micah structured deals, underwrote for worst-case scenarios, and still found upside  

- The transition from broker to principal and the influence of early mentors  

- Raising children without entitlement while building wealth  

- Using his business as a platform for purpose and service to the community  

Micah’s outlook is rooted in gratitude and long-term thinking, with a focus on character, consistency, and building something that matters. This episode is a must-listen for anyone navigating the intersection of values, leadership, and real estate.

Links:

Micah on LinkedIn - https://www.linkedin.com/in/micah-lacher-1366151/

Anchor Investments - https://www.anchorinv.com/

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:

(00:00:00) - Intro

(00:01:14) - Micah’s upbringing

(00:08:03) - Early career

(00:13:19) - Mentors, marriage, and breaking phone addiction

(00:19:17) - The fear of raising entitled children

(00:22:16) - Learning the brokerage game

(00:30:14) - Transitioning from broker to principal

(00:39:24) - Developing “Walmart shadows” and experiencing the GFC

(00:45:06) - Raising capital in 2009

(00:51:51) - Thoughts on RTO

(00:53:42) - How do you think about your business today, given how you started?

(00:57:30) - Using the business to effect change

(01:10:37) - Establishing a competitive edge

(01:13:08) - Developing hotels in Nashville - and giving away the profits

(01:23:11) - The Nashville market

(01:27:34) - What’s your favorite hotel?

In this episode of Masters of Moments, host Jake Wurzak sits down with Jesse Rack, founder and CEO of Rack Electric, to unpack one of the most impressive and unconventional entrepreneurial stories in the home services industry.

Jesse shares his journey from Queens, New York, where he played college football and briefly pursued the NFL, to running a fast-growing business empire focused on electrical work, energy, and infrastructure across Florida. After stepping away from coaching football and returning to Florida to support his family, Jesse took over his father's small electrical business with a bold vision: to build a brand, not just a company.

What started with one truck and a handful of employees is now a multi-vertical operation with over 200 employees, five divisions, and specialties that include generators, propane delivery, solar installations, and EV charging infrastructure. Jesse breaks down how he's scaled the company by hiring for attitude, investing in operational systems, and acquiring other trades businesses through strategic M&A.

This episode covers:

- Jesse’s sports background and how it shaped his leadership style  

- Building Rack Electric from a local business into a state-wide brand  

- Creating a training pipeline for tradespeople and launching in-house licensing programs  

- How to buy, turn around, and integrate struggling home service companies  

- Why customer experience and honest communication are non-negotiables  

- The power of handwritten letters in sourcing acquisition opportunities  

- Lessons in grit, recruiting, and the value of walking the job site  

If you're interested in trades entrepreneurship, home services, or building a real business with staying power, Jesse’s story is as real and raw as it gets.

Links:

Rack Electric - https://www.rackelectric.com/

Jesse on LinkedIn - https://www.linkedin.com/in/jesse-rack-488185171/

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:

(00:00:00) - Intro

(00:01:02) - Jesse’s background

(00:06:16) - The importance of trades and education

(00:08:56) - Challenges and growth in the electrical business

(00:16:35) - Marketing and expansion strategies

(00:20:33) - Current state of Rack Electric

(00:25:54) - Service excellence and customer experience

(00:31:41) - Leadership and team building

(00:44:08) - Navigating private equity and future goals

(00:45:15) - Importance of people and purpose

(00:47:44) - Negotiating debt and bulk buying

(00:50:24) - Asset purchase strategy

(00:56:21) - Building relationships and recruiting

(00:59:19) - HVAC business expansion

(01:12:27) - Future goals and vision

(01:16:55) - Favorite hotel experience

(01:21:04) - Closing remarks

In this special “Coaching Call” Jake Wurzak goes solo to share everything he’s learned from over a decade of raising capital in real estate. Drawing on personal experience—from his first $7 million deal with no clear path to funding, to building DoveHill into a hospitality investment platform—Jake walks through the real, unfiltered playbook for getting deals financed.

This episode is packed with insights on how to approach high-net-worth individuals, build trust with investors, and create compelling deal collateral that actually converts. Jake also breaks down how he structures investor communications, designs pitch decks and memos, leverages tools like Juniper Square, and uses short personalized videos to bring deals to life. It’s the same method he’s using today to raise preferred equity for a current hotel redevelopment project in Savannah, Georgia.

Key lessons include:

- Why raising money for a single deal is easier than launching a fund

- The importance of being honest, conservative, and clear with investors

- How to use storytelling, design, and delivery to drive commitments

- Tips for building investor databases, managing follow-ups, and closing deals

- Real talk on sharing upside, walking away from bad capital, and learning through failure

Whether you’re about to raise your first $1 million or scaling to institutional capital, this behind-the-scenes coaching call gives you a candid, detailed roadmap for how to actually get it done.

Connect & Invest with Jake:

Follow Jake on X: https://x.com/JWurzak

1 on 1 coaching with Jake: https://www.jakewurzak.com/coaching

Learn How to Invest with DoveHill: https://bit.ly/3yg8Pwo

Topics:

(00:00:00) - Intro

(00:00:38) - More on DoveHill

(00:05:05) - Jake’s First Deal and Lessons Learned

(00:08:57) - Raising Capital: Strategies and Tips

(00:14:44) - Creating Effective Investment Memos

(00:16:59) - Designing Investment Decks

(00:35:26) - Engaging Investors with Video Pitches

(00:40:21) - Investor Intake Process

(00:44:01) - Negotiation Tips

(00:45:09) - Q&A: Meeting Potential Investors

(00:48:59) - Q&A: Handling Design and Pre-Development Costs

(00:53:06) - Q&A: Capital Structure and Investor Profiles

(00:56:22) - Q&A: Overcoming Appraisal Challenges

(00:59:28) - Q&A: Partnering in New Markets

(01:02:06) - Q&A: Preferred Equity and Fund Structures

(01:17:58) - Q&A: Subscription Process and Investor Relations

(01:22:27) - Unexpected Investor Stories