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

Patrick Carroll is the founder and CEO of CARROLL, a prominent real estate investment company. From a young age, Patrick Carroll envisioned building a real estate company from the ground up. The ambitious entrepreneur leveraged what was initially a multi-family and retail assets company into a leading real estate empire. 

As CEO, Patrick helps define and implement strategic plans designed to further expand all facets under the CARROLL portfolio. As a disciplined investor, Patrick carefully balances acquisitions and dispositions, and has led to $12.1 B in acquistions and $8.8 B in dispositions of multifamily real estate producing an average gross IRR of 29%.

Founded in 2004, CARROLL marked the beginning of Patrick’s real estate investment and development career. Patrick’s early success in the industry came from residential investments and developmental projects across the Southeast, which, in turn, produced the opportunity to develop retail centers, mixed-use properties, and student housing.

In 2009, Patrick acquired three property management companies, creating the large-scale infrastructure for what CARROLL is today. Compounding on his experience with investment, property management, development, and construction, Patrick has taken a modest initial investment and cultivated that into a 30,000-unit portfolio.

Links:

Patrick Carroll - https://mpatrickcarroll.com/

Patrick on Instagram - https://www.instagram.com/patrickcarroll/

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  

(00:01:11) - Patrick’s Transition from House-Flipping to Multifamily  

(00:13:02) - What Was Your Deal Criteria Early On?  

(00:18:45) - How Were You Finding Deals?  

(00:22:38) - How Did You Scale?  

(00:31:18) - Building a Profitable Management Company  

(00:33:21) - Raising Capital & Getting Deals Done  

(00:49:14) - The Buy-Fix-Sell Strategy  

(01:06:57) - Pausing Deals Post-COVID  

(01:09:46) - Selling the Business  

(01:18:23) - Thoughts on the Market Today  

(01:26:22) - Mental Health  

(01:31:49) - What’s Your Favorite Hotel?

This episode originally aired on November 6th, 2024

In this episode of Masters of Moments, I sit down with Chris Hatch, Principal at Forza Commercial, to break down the high-stakes world of retail real estate development. Chris grew up in a real estate family, learning the business from the ground up, and those early lessons shaped how he approaches site selection, deal structuring, and scaling development projects today.

We dive into:

Chris also shares behind-the-scenes stories from working with national tenants like Starbucks, Dutch Bros, and Raising Cane’s, explaining what makes a high-performing retail site and how shifting consumer trends are influencing real estate decisions.

If you're interested in commercial real estate, retail development, or the business of site selection, this episode is packed with insights from someone who’s been in the trenches and built a highly successful development business.

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

Links:

Links:

Chris on X - https://x.com/chriswhatch

The Dirt Dog Podcast on Spotify - https://open.spotify.com/show/0EyUYpLUMbJKqEzprNuLPM?si=e48d7ffc5ddb48a0

Topics:

(00:00:00) - Intro

(00:00:56) - Chris’ Background and Career

(00:05:36) - The Magic of Drive-Thrus

(00:07:03) - Lessons from Early Real Estate Experiences

(00:09:41) - Navigating the Real Estate Market

(00:11:04) - The Evolution of Site Selection

(00:13:35) - Building a Real Estate Portfolio

(00:17:05) - Challenges and Strategies in Real Estate Development

(00:32:44) - The Appeal of Triple Net Leases

(00:40:53) - Retail Trends and Market Shifts

(00:41:34) - Diversification in Retail Investments

(00:43:38) - The Future of Gas Stations

(00:45:07) - Impact of Cloud Kitchens

(00:46:54) - Cap Rates and Popular Retail Tenants

(00:50:36) - Challenges in Retail Development

(00:58:38) - Managing Multiple Development Projects

(01:15:50) - Favorite Hotels and Closing Thoughts

Katharine is CEO and Co-Founder of Stuf, one of Fast Company’s World’s Most Innovative Companies in 2022. She was named to Inc. Magazine’s Female Founders 100 list in the same year. Katharine is passionate about reinventing consumer experiences in the physical world and leads the company’s strategic vision and overall strategy in transforming the self-storage industry. 

From 2015-2020, Katharine led supply growth at Industrious, the nation’s largest premium shared workplace provider. She built and managed a 20+ person team and oversaw the company’s rapid expansion while developing go-to-market strategies for new digital products and tenant experience services. As VP of Real Estate, Katharine pioneered an "industry first” 

asset and liability-light growth strategy leading to CBRE’s partial acquisition of Industrious in early 2021.  

Prior to Industrious, Katharine worked at Equinox as Manager of Development, supporting the company’s national expansion of luxury fitness clubs. She previously worked at L&L Holding Company and PGIM Real Estate (Prudential).  

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

Links:

Katharine on LinkedIn - https://www.linkedin.com/in/katharinelau/

Stuf - https://www.stufstorage.com/

Topics:

(00:00:00) - Intro

(00:01:06) - Katherine’s career in RE/Hospitality

(00:07:36) - Advice to young people in RE + AI

(00:11:06) - Insights learned from development at Equinox

(00:13:51) - Niche vs. expansive real estate

(00:15:27) - Inside building a successful coworking space

(00:29:40) - remote work philosophies

(00:33:36) - Starting and building ‘Stuf’

(01:12:00) - What would you like to be doing more or less in 3 years?

(01:13:14) - How do you compete with your larger competitors?

(01:15:19) - What was the most surprising thing you’ve gotten wrong in building Stuff?

(01:23:08) - What’s your favorite hotel?

In this episode of Masters of Moments, I sit down with Adam Guy to explore his unconventional path from Missouri to multi-industry success. Adam’s journey started early—performing illusion shows at just seven years old—which soon evolved into a full-fledged business, booking corporate gigs across the Midwest.

His entrepreneurial instincts didn’t stop there. After a stint in basketball and communications studies at the University of Missouri, Adam dropped out to launch a wristband company, capitalizing on the craze sparked by Lance Armstrong’s charity bands. That venture turned into a profitable exit, leading him into the hospitality space, where he transformed a small bakery and café into a $150 million-a-year powerhouse.

Now, Adam is redefining luxury travel with Exclusive Vacations, creating a high-end vacation rental experience built on exceptional hospitality and premium amenities. We break down his strategic approach to real estate investment, property management, and business scaling, along with the mindset that has fueled his success across multiple industries.

If you're passionate about entrepreneurship, hospitality, and game-changing business strategies, this episode is packed with insights you won’t want to miss.

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

Links:

Adam on LinkedIn - https://www.linkedin.com/in/adamguyceo/

Four Seasons: The Story of a Business Philosophy

Topics:

(00:00:00) - Intro

(00:00:46) - Adam’s background and career

(00:06:53) - Setting up a factory in China

(00:09:38) - Dropping out of College to pursue a career in the food industry

(00:25:38) - Evolving the business from restaurants into food services

(00:33:53) - Learning how to acquire a food-services business

(00:50:09) - Life working for fraternities and sororities

(00:58:58) - The impact of delivery apps on in-house food services

(01:00:46) - The operations side of the business

(01:11:23) - Adam’s hospitality side-hustle

In this episode of Masters of Moments, I share my experiences in hospitality and real estate investment, from raising $6 million for a preferred equity deal to handling unexpected challenges in hotel management. I also discuss the shift toward experiential and lifestyle hotels and why smaller investment opportunities can offer strong returns.  

I also discuss how technology improves hotel operations, makes it easier to manage boutique properties, and the potential benefits of incorporating residences into hotel projects. I also break down key strategies for building strong investor relationships and navigating market trends.  

Other topics include:  

- Finding value in overlooked investment opportunities

- Revenue strategies for hotel profitability

- Lessons learned from setbacks in hotel operations

Whether you're new to hospitality or a seasoned investor, this episode offers practical insights on building and managing successful hotel projects.

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

(00:00:51) - Exploring Estelle Manor: A New Hospitality Trend

(00:02:46) - Insights from the Lodging Investment Conference

(00:04:13) - Opportunities in Small Deals and Private Equity

(00:06:54) - The Shift in Hospitality Preferences

(00:08:06) - Challenges for Traditional Hotels

(00:09:08) - The Rise of Experiential and Lifestyle Hotels

(00:09:50) - Case Study: The Breakers Hotel

(00:11:01) - The Middle Market's New Options

(00:20:16) - Automating Small Hotels: A Success Story

(00:28:24) - Scaling Challenges in the Hotel Business

(00:28:56) - Dealing with Hotel Incidents

(00:31:41) - Balancing Occupancy and Revenue

(00:33:30) - Strategies for Managing Hotel Rates

(00:37:55) - The Rise of Experiential Travel

(00:43:47) - Incorporating Residences in Hotels

(00:46:50) - Fractional Ownership and Real Estate Strategies

(00:53:16) - Creating a Unique Hotel Brand

(00:55:26) - Effective Communication for Raising Capital

(00:58:41) - Conclusion and Final Thoughts

Links:

Estelle Manor - https://www.estellemanor.com

The Lodging Conference - https://www.lodgingconference.com

Hyatt Regency O'Hare Chicago - https://www.hyatt.com/en-US/hotel/illinois/hyatt-regency-ohare-chicago/ohare

Chicago Athletic Association Hotel - https://www.chicagoathletichotel.com

Muse - https://www.muse.com

SALTO Systems - https://www.saltosystems.com

DIAMO - https://www.diamo.com

Cost.com - https://www.cost.com

AutoCamp - https://www.autocamp.com

Belmond - https://www.belmond.com

LVMH - https://www.lvmh.com

All-In Podcast - https://www.allinpodcast.co

CloudKitchens - https://www.cloudkitchens.com

Antonia Botero takes us on a deep dive into the evolution of taste in architecture, shaped by her experiences with historic buildings in New York City. We explore the power of intentional design—how the seamless blend of interior and exterior aesthetics can transform a space—and the unique challenges of adaptive reuse projects.

Antonia also shares her journey from architecture to development, highlighting the adaptability and teamwork required to succeed in both fields. We unpack the complexities of working on legendary projects like the TWA Hotel, where every design choice plays a crucial role in crafting a cohesive and compelling space.

To wrap up, we discuss the highs and lows of launching MADDPROJECT, the lessons learned along the way, and Antonia’s favorite hotels around the world—places that embody design excellence and unforgettable experiences. If you’re passionate about architecture, development, or the art of creating remarkable spaces, this episode is packed with insights you won’t want to miss!

Links:

Antonia on LinkedIn - https://www.linkedin.com/in/antonia-botero-ra-ncarb-6473282b/

MADDPROJECT - https://www.maddproject.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

(00:01:08) - How to develop taste & design insights

(00:07:50) - Antonia’s career

(00:17:44) - How to pay architects and designers

(00:19:53) - Office to residential conversions

(00:30:38) - How do you run Maddproject today?

(00:37:18) - GC experiences

(00:44:33) - What would your clients say about your development management business?

(00:46:57) - How did you get into hotels?

(00:56:39) - Creating a vibe

(00:57:59) - Common mistakes made 

(01:06:19) - Structuring a Development-Management company

(01:23:25) - What is your favorite hotel?

In this episode of Masters of Moments, I take a step back to reflect on how far the show has come and express my gratitude to every listener who’s been part of this journey. If you’ve been enjoying the conversations, I’d love for you to leave a review and send in your dream guest suggestions—your input helps shape the show's future!

This time, I’m diving deep into the art of bringing a boutique hotel to life—from the first spark of an idea to the moment guests step through the doors. I break down the essential steps: crafting a compelling brand identity, assembling the perfect team (think top-tier designers, architects, lighting experts, and kitchen consultants), and setting a crystal-clear vision with a detailed mood board to shape every detail of the guest experience.

I also explore the power of model rooms—why they’re game-changers—and the importance of seamless coordination to ensure every element comes together flawlessly. Plus, I share insider tips on leveraging social media and building an online presence that makes your hotel stand out. Whether you dream of developing a boutique hotel or love the behind-the-scenes of hospitality design, this episode is packed with insights you won’t want to miss!

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

Check out Sleeper Magazine - https://www.sleepermagazine.com/

Topics:

(00:00:00) - Intro  

(00:00:34) - Reflecting on 100 Episodes of Masters of Moments  

(00:02:08) - How to Conceptualize and Design a Hotel  

(00:04:12) - Creating a Vision Board for Your Hotel  

(00:09:43) - Hiring the Right Team: Designers and Architects  

(00:14:32) - The Phases of Hotel Design  

(00:17:51) - Additional Consultants and Model Rooms  

(00:23:12) - Final Steps: Technology, Marketing, and Launch  

(00:26:54) - Conclusion and Final Thoughts  

In this episode, Jake emphasizes the importance of having a team for unbiased insights, building cushion into deals, and learning from both your mistakes and others. 

He shares an in-depth look at his process for underwriting hotel deals, including revenue assumptions, expense analysis, financing structures, and the role of pro forma models. 

Jake also touches on the significance of community and networking in the hospitality industry, leveraging past partners and peers for feedback and collaboration. From discussing a potential but ultimately avoided deal in New England to highlighting the benefits of working with branding agencies and interior designers, this episode is a masterclass!

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

(00:00:56) - The Value of a Hospitality Network

(00:02:40) - Savannah Hotel Deal and Due Diligence

(00:03:55) - Navigating Investment Strategies and Honest Feedback

(00:06:23) - Underwriting Deals: A Case Study

(00:08:53) - Seasonal Hotel Operations and Business Plan

(00:15:03) - Evaluating Hotel Deals and Financial Metrics

(00:25:28) - Short-Term Rental Opportunities

(00:26:06) - Financing and Bridge Loans

(00:27:52) - Pro Forma Metrics and Cash Flow

(00:30:30) - Internal Memos and Investment Committee

(00:32:34) - Lease to Buy Options and Master Leases

(00:37:38) - Pro Forma Creation and Sensitivity Analysis

(00:40:13) - Investor Returns and Deal Structures

(00:45:38) - Design and Renovation Budgeting

(00:50:26) - Final Thoughts and Q&A