The More Smarter Show

In this solo episode, Jake and Dylan take a step back and talk through the evolution of the show after 42 episodes.

They break down what’s working, what’s not, and where things are headed next. From bringing on higher-level guests across the country to rethinking the structure of each episode, this is a real look behind the scenes of building a podcast from the ground up.

They also get into:

• Why better guests don’t always mean better content
• The challenge of interviewing people you don’t know
• How the show has improved since the early episodes
• The difference between “views” and real listeners
• Why focusing on content over growth is the long game
• Lessons from networking events and unexpected opportunities

Plus, a tangent into real estate, cash flow vs appreciation, and what it actually takes to build long-term wealth.

In this episode of The More Smarter Show, Jake and Dylan sit down with Baltimore-based real estate agent Taylor Sevik to break down what it actually takes to build a thriving real estate business from scratch.

Taylor shares his journey from working in higher education to becoming a full-time agent, how COVID pushed him to rethink his career path, and how he scaled to over $17M in annual sales — all by focusing on relationships instead of cold leads.

The conversation dives into:

• Why your “sphere” is the most valuable source of business
• How emotional intelligence beats traditional sales tactics
• The reality of balancing (or not balancing) work and life early on
• Systems, time blocking, and buying back your time
• When to stay on a team vs. going out on your own
• Building a business that actually fits the life you want

If you’re in real estate, sales, or just trying to figure out your next move, this episode is packed with practical insight and real talk.

Episode 40… and our first ever no-show guest.

So yeah… Jake took that personally.

In this solo episode of The More Smarter Show, things start off a little different when a scheduled guest completely ghosts the podcast. No text. No email. Nothing. And Jake? He’s not exactly letting it slide.

From declaring the mystery guest “dead to me” to debating whether that reaction is justified (or slightly insane), this episode turns into a real conversation about respect, time, and how you show up in business.

Dylan tries to play peacemaker. Jake doubles down. You decide who’s right.

We also get into:

• Why no-showing is worse than making a mistake

• Setting boundaries with clients (and not being “on call” 24/7)

• Real estate investing updates from both Jake and Dylan

• The difference between working more harder vs. more smarter

• And whether early-career grind actually pays off

If you’ve ever been stood up, canceled on, or felt like your time wasn’t respected… this one will hit.

Or you’ll think Jake needs to relax. That’s fair too.

Listen and decide.

In Episode 39 of The More Smarter Show, Jake and Dylan sit down with Angelo Cirinelli, co-founder of Sterling Adams Wealth Management, to talk about building a financial planning business from zero to 30+ clients in just a few years. Angelo shares how he transitioned from molecular biology to advising real estate investors, the systems and workflows that helped him grow, and why networking, mentorship, and credibility matter more than social media for long-term client relationships.

The conversation dives into financial planning for real estate investors, scaling a service business, hiring the right help, and the role personality and real-world experience will play in a future shaped by AI. If you’re building a business, investing in real estate, or trying to get smarter about money and growth, this episode is packed with practical insights.

In episode 38 of The More Smarter Show, Jake and Dylan sit down with Greg Silverman, formerly in the real estate development spaced, turned tech innovator. Greg shares how he pivoted from traditional real estate to revolutionizing building infrastructure with low-voltage, AI-ready electrical systems as Chief Revenue Officer of MHT Technologies.

They dive into the challenges of scaling a niche tech company, global manufacturing, acquisitions, and building a culture that supports rapid growth. Learn how Greg’s experience in development gives him an edge in creating smarter, more valuable buildings. This episode is a deep dive into the intersection of tech, real estate, and forward-thinking business strategy.

Hiring your first employee isn’t just a business decision. It’s an identity shift.In this episode of The More Smarter Show, we sit down with Ryan Kuhn of Kuhn Family Home Inspections to break down what it really looks like to go from solo operator to business owner. The fears, the control issues, the financial pressure, and the moment you realize you can’t grow without letting go.We talk about:• The difference between owning a job and owning a business• The real reason most service businesses never scale• What finally pushed Ryan to make his first hire• The numbers behind home inspections most people don’t see• Pricing, liability, and why being “cheap” costs more in the long run• How to think about recurring revenue in service-based businessesIf you're maxed out, overwhelmed, and doing everything yourself, this episode is for you.Because the truth is simple:If you don’t hire, you don’t scale.

In Episode 36 of The More Smarter Show, Jake and Dylan sit down with New Jersey real estate leader John Schlaffer to unpack what it really takes to grow from agent… to broker… to visionary leader.John shares his 9-year journey in real estate, including:Starting at a big-box brokerageJoining a 9-agent boutique firmAcquiring that brokerage just 3 years into his careerTaking over on January 1, 2020… right before COVID shut the world downEventually merging with Keller Williams and stepping into large-scale leadershipThis episode dives deep into what most agents never see:🔹 Brokerage vs. Team ModelIs owning a brokerage really the goal?John explains why he now believes the team model is the future of real estate and why brokerage ownership isn’t always the smartest move long term.🔹 Naivety vs. ExperienceSometimes you have to work more harder before you can work more smarter.We talk about:67-day work streaksBeing the “toilet paper manager” of your own companyThe reality of scaling without systemsWhy growth without structure leads to burnout🔹 What Does Success Actually Look Like?Is it:$1M commissions?Selling the most houses?Building a legacy?Being home by 5pm for your kids?John challenges us with a powerful question:“What does success look like to you?”🔹 Deep Work, Boundaries & Dad HoursJohn wakes up at 3:59 AM every day to beat the world by one minute.We discuss:Deep work vs. constant phone distractionsWhy letting calls go to voicemail might make you more productiveFamily-first structure without sacrificing growthBuilding a life, not just a business🔹 Writing a LegacyJohn is currently writing a book titled “3:59 AM” — a chapter-by-hour blueprint for maximizing your day and building intentional momentum.This episode is about:Leadership under pressureScaling without losing yourselfMaking decisions that won’t please everyoneRejection as proof you’re playing the gameAnd designing a business that supports your life, not replaces it

In this special Presidents Day episode, Jake and Dylan sit down with 18-year-old high school senior Clinton to talk about one big question:

Is college still worth it in 2026?

Clinton is in his second semester of senior year, recently accepted into Georgia State, considering trade school, and seriously questioning whether taking on debt is the right move in a world dominated by AI, entrepreneurship, and changing career paths.

This episode dives into:

• Is college a guarantee or a gamble?
• The pressure of “decision day” and social expectations
• Trade school vs. traditional college
• Entrepreneurship at 18
• Blue collar opportunity in a digital world
• How AI is changing the value of degrees
• Taking a gap year and betting on yourself

Clinton shares a mature, thoughtful perspective on risk, independence, and building long-term success early. Jake and Dylan reflect on their own paths, from college to real estate to entrepreneurship, and debate what the future of education really looks like.

In this episode of The More Smarter Show, Jake and Dylan sit down with Andrew Stadelberger, founder of PlayerCoach, to break down how modern advertising actually works.

Andrew explains his philosophy of “hitting it where they ain’t,” why great marketing is a long game, and how his Jersey Shore-based agency competes with big-city firms by using a fractional team of world-class talent from Google, LinkedIn, and even Hot Ones.

They dive into:

• How ad agencies really make money

• Why results take 3 to 6 months

• The pros and cons of fractional vs in-house teams

• How AI is changing marketing and communication

• Why low overhead can actually make you a better partner

• What makes a “serious agency for serious businesses”

If you’ve ever wondered how advertising actually works behind the scenes, or how to stand out in a crowded market, this episode is for you.

Okay Puerto Rico is technically US land, but you know what we mean.

In this episode of The More Smarter Show, Jake and Dylan sit down with Marc Weisi, owner of a 16-room boutique hotel in San Juan, Puerto Rico. Marc breaks down his journey from Wall Street to full-time real estate and hospitality, sharing what it really takes to run a high-touch, operationally intensive hotel business.

They dive into:

• Why hospitality is more “business” than real estate

• How Marc designed the hotel around a very specific guest avatar

• Hiring, SOPs, and building systems in a small boutique operation

• Using technology like channel managers and Asana to scale

• Marketing through micro-influencers and OTAs

• The economics of private lending versus equity

• Puerto Rico hospitality tax credits and why they’re so powerful

• Real, raw stories from running a hotel in a transitioning neighborhood

If you’re curious about entrepreneurship, boutique hospitality, or creative real estate strategies, this episode pulls back the curtain on what it actually looks like to build, operate, and scale a hotel in Puerto Rico.