The More Smarter Show

In this episode we sit down with Josh Stankard, the founder of NotaryLive. We get into what it takes to build a real company from scratch, what the early chaos looked like, and how he turned a simple idea into a national platform.

We discuss something most founders avoid, the mindset part. The pressure, the identity shift, and the moment you realize your company cannot be the only thing that defines you. Josh opens up about learning to step back, protect his sanity, and find a healthier balance while still pushing the business forward.

If you want an honest look at what building a startup actually feels like, this conversation is going to hit. Josh keeps it real, and the lessons apply to anyone trying to grow something without losing who they are.

Enjoy the episode and share it with someone who needs to hear a founder talk like a real human instead of a pitch deck.

Why do people love watching the top fall off?
Whether it’s binging a Netflix series about rich-people scandals or rooting against the Chiefs because they’re “too good,” there’s something about success that makes everyone want to see a crack in the armor. In this episode, we dig into why that happens, what it says about us, and most importantly how you actually get to the top and stay there.

In this episode of The More Smarter Show, Jake and Dylan sit down with Dr. Joe , a physical therapist turned real estate investor who now manages over 70 rental units across New Jersey, including a unique portfolio of licensed rooming houses.

Dr. Joe shares how he went from balancing a full-time healthcare career to scaling a diverse investment portfolio, all while managing a family and multiple businesses. The conversation dives into:

• How a simple cash-out refinance kickstarted his real estate journey

• Why rooming houses can be both profitable and socially impactful

• The challenges of tenant screening and running operations with a “live-in operator” model

• Balancing stability, cash flow, and compassion in affordable housing

It’s a mix of business strategy, real estate insight, and practical lessons on working more smarter , not just harder.

Listen to hear how Dr. Joe built stability and scale in one of the toughest real estate markets in the country.

Chris Barry joins The More Smarter Show to talk about what it really takes to build a real estate portfolio while balancing a full-time job and family life. From scheduling every hour of the week to setting long-term goals with purpose, Chris shares how systems and clarity have helped him scale across states without losing focus.

He also dives into the mindset side of investing... taking calculated risks, learning from the early mistakes, and avoiding the trap of waiting for the “perfect” time to start. Whether you’re chasing your first deal or trying to scale smarter, this episode is a playbook for action, balance, and building a life that actually fits your vision.

In this episode of The More Smarter Show, Jake and Dylan sit down with Bill Kwong to talk about the power of just jumping in. From business ideas that started as “why not?” moments to ventures that didn’t have a plan but somehow worked out, the three break down what happens when you stop waiting for the perfect time and just take action.Bill shares his own experiences diving headfirst into new projects... the wins, the near-misses, and the lessons learned along the way. Whether you’re thinking about starting a business, buying a property, or launching something on your own, this conversation will remind you that momentum beats perfection every time.

In this solo episode of The More Smarter Show, Jake and Dylan ditch the guests and get real about vision, effort, and working smarter in business and life. Jake shares how he wrote a fake news article about his future three years from now — mapping out what his companies, employees, and reputation will look like. Dylan takes a different approach, using ChatGPT to do the same exercise and then scheduling it to email himself in the future.

They break down how goal-setting can go beyond money — focusing on reputation, time allocation, and daily consistency — and debate what “working more smarter” really means in real estate and entrepreneurship. From balancing passion with practicality to creating culture and clarity, this conversation is part mindset, part business strategy, and fully more smarter.

What makes a roofer stand out in an industry full of contractors who all promise the same thing? For David Beattie, it’s simple: being genuine, putting people first, and refusing to run his business like “just another roofing company.”In this episode, David shares how he got his start in roofing at a young age, the lessons he learned from working his way up, and why he ultimately launched his own company. We dive into the systems he’s built, the growth mindset that keeps him moving forward, and the personal touch that sets him apart from the competition.If you're a small business owner you'll definitely connect with David’s story. Learn his insights on leadership, customer service, and building trust the right way.

On this episode of The More Smarter Show, Dylan and Jake sit down with Scott Bauer, founder of Coast Digital, to unpack the journey from side hustle to full-scale creative and performance marketing agency. Scott shares how landing Barstool Sports as their first client shaped the company’s early trajectory, the hard lessons learned from over-diversifying into creative production, and why returning to core competencies proved essential.

The conversation dives deep into specialist hiring trends, the pitfalls of remote work, and Coast Digital’s scaling philosophy. Scott also discusses leveraging AI with a human touch, key profitability metrics, client acquisition strategies, and his candid take on the company’s sellability and acquisition potential.

This episode is a must-listen for entrepreneurs, marketers, and anyone navigating the challenges of scaling a service-based business.

What really happens when a client leaves? Relief, rage, or reflection? In this episode, Dylan and Jake sit down with Jonathan Tiralosi of Bullseye Bookkeeping to talk about the lessons hidden inside client turnover.

They break down the difference between being self-employed and being a true business owner, why retention is more valuable than replacement, and how to build a company that’s actually sellable. Along the way, they dive into referrals, red-flag clients, and the mindset shift from working “more harder” to working “more smarter.”

If you’ve ever wondered how to scale beyond one client, keep your best relationships strong, and create systems that last, this conversation is for you.

In this episode of The More Smarter Show, hosts Dylan and Jake sit down with mortgage lender, real estate investor, and Bitcoin enthusiast Rob Glasser to tackle one of the biggest financial questions of our time: Real Estate or Bitcoin?

Rob shares how he transitioned from a 9-to-5 accounting job to building a mortgage and investment business fueled by authenticity, radical honesty, and a value-first approach. He opens up about selling his own investment property, why he believes Bitcoin is the ultimate store of value, and the lessons he’s learned from both markets.We cover:How to decide between real estate and Bitcoin in 2025Why Rob sold his Bayonne, NJ property in a hot marketThe truth about self-custody and protecting your wealthThe key differences between Bitcoin and all other cryptoHow to build relationships in business without wasting time

Resources Mentioned:The Bitcoin Standard — Saifedean AmmousBroken Money — Lyn AldenThe Price of Tomorrow — Jeff BoothWhat is Money Podcast — Robert Breedlove