Are you trying to figure out how to transition from a full-time W2 job into a thriving, full-time real estate career? In this episode of the Better Agent Podcast, host Josh Lavik sits down with Kayleigh Chrostowski, a powerhouse broker based in Janesville, Wisconsin. Despite starting her career while working full-time as an insurance auditor for the state, Kayleigh managed to close an incredible 17 transactions in her first year! Now, just two and a half years in, she has her broker’s license and is nearing 60 career transactions.

Kayleigh shares the secrets behind her rapid success, including how she utilized her parents' background in contracting to confidently estimate repair costs for her buyers, and why she ditched the "blazer and heels" to show up authentically (sometimes in paint-covered clothes!) for her clients. Josh and Kayleigh also discuss the harsh realities of work-life balance during the spring market, the danger of relying too heavily on AI for contractor quotes, and why you can never take it personally when a friend uses another agent.

🎧 Hosted by: Josh Lavik

🎤 Featuring: Kayleigh Chrostowski, Real Estate Broker

Kayleigh Chrostowski is a real estate broker at Rock Realty in Wisconsin. Drawing on her background in corporate marketing and state auditing, she brings a strong business foundation to her clients. Raised by licensed general contractors, she leverages her deep knowledge of construction and design to help buyers, sellers, and investors see a property's true potential. 

💡 What You’ll Learn in This Episode:

✔️ The Side-Hustle Grind: How Kayleigh Chrostowski successfully closed 17 properties in her first year while working a full-time, travel-heavy government auditing job.

✔️ Authenticity Wins: Why ditching the "perfect realtor" facade and showing up as your true, authentic self builds deep trust with clients.

✔️ The Contractor Advantage: How to confidently estimate home repair costs for your buyers to keep deals alive, and why you shouldn't rely on ChatGPT for contractor quotes.

✔️ Boundary Setting: Why every new agent must get a separate business phone before starting their career.

✔️ Handling Rejection: How to manage your ego and maintain relationships when friends or family members choose to buy or sell with a different agent.

📇 Connect with Kayleigh Chrostowski:

🌎 Website → https://realtorkayleigh.com/

📘 Facebook → https://www.facebook.com/kayleigh.chrostowski/

📷 Instagram → https://www.instagram.com/kayleighchrostowski/

🎙 FOLLOW JOSH LAVIK & THE BETTER AGENT PODCAST:

🌎 Website → https://www.joshlavik.com/

📘 Facebook → https://www.facebook.com/joshlavikassoc

📷 Instagram → https://www.instagram.com/jla_madison/

🔗 LinkedIn → https://www.linkedin.com/in/jlavik

🔖 DON’T FORGET TO LIKE, SUBSCRIBE, AND COMMENT BELOW!

⭐ Produced by Icons of Real Estate – iconsofrealestate.com

Are you overcomplicating your real estate business with too many lead generation strategies? In this episode of the Better Agent Podcast, host Josh Lavik sits down with Kyle Ristow, an impressive young agent based in Milwaukee, Wisconsin, who closed over 300 transactions in just a few short years after getting his license right out of high school!

Kyle shares his incredible journey from struggling to close a single deal his first six months to becoming a showing assistant handling 1,000+ showings a year, and eventually building a fast-growing 7-person expansion team. Kyle breaks down his simple, proven formula for success: dedicating one hour a day to "The One Thing," having 20 real estate conversations daily, and committing to a 36-touch follow-up campaign. Josh and Kyle also discuss the power of authenticity, sharing why showing up in a hoodie can win you the listing over a fancy suit.

🎧 Hosted by: Josh Lavik

🎤 Featuring: Kyle Ristow, Real Estate Team Leader

Kyle Ristow is a Milwaukee Realtor and founder of Luxe Real Estate Haven Group. Specializing in everything from new homebuyers to international investments, he combines luxury marketing with deep local knowledge to guide clients through the Southeast Wisconsin market. Known for his award-winning, white-glove service, Kyle prioritizes a client-first approach and actively gives back by mentoring students in his community.

💡 What You’ll Learn in This Episode:

✔️ The 1,000 Showing Hustle: How joining a top team as a showing assistant gave Kyle the ultimate real estate education.

✔️ The 20 Conversations Rule: Why having 20 real estate conversations every single day is the ultimate cheat code to explosive growth.

✔️ The "One Thing" Strategy: How to time-block one uninterrupted hour a day for lead generation to prevent a "yo-yo" business.

✔️ The 36-Touch Campaign: A step-by-step breakdown of how to touch base with past clients and your sphere 36 to 70 times a year.

✔️ Authenticity Wins: Why you don't need a suit to win listings—and how showing up as your true self builds ultimate client trust.

📇 Connect with Kyle Ristow:

🌎 Website → http://www.luxehavenwi.com/

📘 Facebook → https://www.facebook.com/RistowKy/

📷 Instagram → https://www.instagram.com/kyleristow_milwaukee_realtor/

🔗 LinkedIn → https://www.linkedin.com/in/kyle-ristow-realtor/

🎙 FOLLOW JOSH LAVIK & THE BETTER AGENT PODCAST:

🌎 Website → https://www.joshlavik.com/

📘 Facebook → https://www.facebook.com/joshlavikassoc

📷 Instagram → https://www.instagram.com/jla_madison/

🔗 LinkedIn → https://www.linkedin.com/in/jlavik
🔖 DON’T FORGET TO LIKE, SUBSCRIBE, AND COMMENT BELOW!

⭐ Produced by Icons of Real Estate – iconsofrealestate.com

Are you playing it too safe in your real estate business? In this episode of the Better Agent Podcast, host Josh Lavik sits down with Stephanie Kaiser, a powerhouse agent from southeastern Wisconsin who closed an incredible 30 deals in her very first year! Stephanie shares her journey from being a stay-at-home mom to a top-producing agent who isn't afraid to "go big."

Stephanie breaks down her bold, out-of-the-box lead generation strategies—like knocking on farmers' doors to find acreage for buyers, adopting a 3-mile stretch of a county highway, and hiding cash prizes at local businesses to build organic community engagement. Josh and Stephanie also discuss the power of visual goal setting, setting strict boundaries with clients to avoid burnout, and why you must anticipate contract issues before they explode into emotional chaos.

🎧 Hosted by: Josh Lavik

🎤 Featuring: Stephanie Kaiser, Real Estate Agent

Stephanie Kaiser is a real estate professional serving Wisconsin. Drawing on her background in psychology and market expertise, she specializes in strategic negotiation and property acquisitions across residential, lakefront, and rural markets.

💡 What You’ll Learn in This Episode:

✔️ The 30-Deal Debut: How Stephanie mastered the fundamentals and closed 30 transactions in her first year.

✔️ Guerilla Lead Generation: Why knocking on farmers' doors, adopting highways, and sponsoring high school jumbotrons beats buying online leads.

✔️ The Scavenger Hunt Hack: How hiding a "sold" sign at local businesses for a $100 cash prize drives massive local engagement.

✔️ Navigating Emotional Chaos: How to proactively anticipate contract problems before they blow up your deal.

✔️ Visualizing Success: Why writing down your goals and keeping a vision board keeps you motivated in a tough market.

✔️ Setting Boundaries: Why answering your phone at 11 PM is setting your clients up for failure.

📇 Connect with Stephanie Kaiser:

📘 Facebook → https://www.facebook.com/stephanie.kaiser634

📷 Instagram → https://www.instagram.com/stephaniesellswi/

🎙 FOLLOW JOSH LAVIK & THE BETTER AGENT PODCAST:

🌎 Website → https://www.joshlavik.com/

📘 Facebook → https://www.facebook.com/joshlavikassoc

📷 Instagram → https://www.instagram.com/jla_madison/

🔗 LinkedIn → https://www.linkedin.com/in/jlavik

🔖 DON’T FORGET TO LIKE, SUBSCRIBE, AND COMMENT BELOW!

⭐ Produced by Icons of Real Estate – iconsofrealestate.com

Are you a newer real estate agent struggling to find momentum and stay afloat? With 87% of agents failing in their first three years, survival in this industry requires serious grit. In this episode of The Better Agent Podcast, host Josh Lavik sits down with Milwaukee-based agent Alexander Reid, who shares his raw and inspiring journey from making just $18,000 his first year to grossing over $275,000.

Alexander opens up about the intense trials of his early career—including a painful breakup, couch-surfing, and navigating a brand-new market—and how he rebuilt his life block by block. Josh and Alexander discuss the power of sticking to a rigid daily schedule, the "leap of faith" required to hire your first assistant, and why you should never judge a client by their appearance or budget. Plus, Alexander shares his transition from agent to real estate investor, and the two commit to a live 6-month accountability challenge!

🎧 Hosted by: Josh Lavik

🎤 Featuring: Alexander Reid

Alexander Reid is the Lead Wisconsin Real Estate Agent at The Reid Group, launching his career in 2016 and building his business through hands-on experience and mentorship. He works with sellers, buyers, and investors across Wisconsin, focusing on strategic negotiations, value-driven results, and long-term client relationships.

💡 What You’ll Learn in This Episode:

✔️ Surviving the Grind: How Alexander pushed past making just $18K his first year to eventually grossing over $275K.

✔️ The Power of a Schedule: Why treating your day like a college athlete treats practice is the key to building massive momentum.

✔️ Never Judge a Client: Why treating every lead equally—whether it's a $7,000 mobile home or a luxury listing—pays off in the long run.

✔️ Taking the Leap of Faith: When and why you should hire a transaction coordinator or assistant to free up your money-making hours.

✔️ Agent to Investor: How to leverage your industry knowledge to start flipping, house hacking, and building long-term wealth.

🎙 Connect with Alexander Reid:

🔗 LinkedIn → https://www.linkedin.com/in/reidgroup/

📘 Facebook → https://www.facebook.com/ReidGroupRE

📷 Instagram → https://www.instagram.com/reidgroupre/

🎙 FOLLOW JOSH LAVIK & THE BETTER AGENT PODCAST:

🌎 Website → https://www.joshlavik.com/

📘 Facebook → https://www.facebook.com/joshlavikassoc

📷 Instagram → https://www.instagram.com/jla_madison/

🔗 LinkedIn → https://www.linkedin.com/in/jlavik
🔖 DON’T FORGET TO LIKE, SUBSCRIBE, AND COMMENT BELOW!

⭐ Produced by Icons of Real Estate – iconsofrealestate.com

Are you an independent real estate agent feeling the heavy weight of burnout? Trying to wear every single hat in your business is the fastest way to lose your momentum. In this episode of The Better Agent Podcast, host Josh Lavik sits down with the dynamic real estate duo, Lori Stuber and Tanya Williams, to discuss the ultimate cure for the solo agent grind.

After 15 years as a solo agent, Lori realized she was losing steam. Instead of quitting, she teamed up with her former client, Tanya, to form a highly successful 50/50 real estate partnership. They break down exactly how matching opposite personalities can skyrocket your business and save your sanity. Tanya also shares the raw, behind-the-scenes story of the day she fired a controlling, multi-million dollar builder client—proving that your self-worth and time are infinitely more valuable than a toxic commission check. You will also learn the communication secrets that keep their pipeline full and why you must build a brand separate from your brokerage.

🎧 Hosted by: Josh Lavik

🎤 Featuring: Lori Stuber and Tanya Williams

The Lorri & Tanya Team: Lorri Stueber and Tanya Williams are licensed real estate brokers with Restaino & Associates Realtors, serving clients across South-Central Wisconsin and Northern Illinois. With decades of combined experience, they work with buyers and sellers across a range of properties, including residential homes, lakefront estates, and new construction.

💡 What You’ll Learn in This Episode:

✔️ The 50/50 Model: How partnering with another agent can instantly cure burnout and double your efficiency.

✔️ Mirror and Match: Josh's top communication strategy for making clients feel truly heard and valued.

✔️ Firing Toxic Clients: Why dropping a demanding, high-revenue client will actually help your business grow (and save your mental health).

✔️ Agent-to-Agent Etiquette: Why ignoring calls and texts from other agents is destroying your reputation and doing a massive disservice to your sellers.

✔️ Brand Yourself First: Why you must own your own email and website URL instead of relying on your broker's platform.

🎙 Connect with Lorri & Tanya Team:

🌐 Website → https://lorriandtanyateam.restainohomes.com/

📘 Facebook → https://www.facebook.com/TeamLorriandTanya

🎙 FOLLOW JOSH LAVIK & THE BETTER AGENT PODCAST:

🌎 Website → https://www.joshlavik.com/

📘 Facebook → https://www.facebook.com/joshlavikassoc

📷 Instagram → https://www.instagram.com/jla_madison/

🔗 LinkedIn → https://www.linkedin.com/in/jlavik
🔖 DON’T FORGET TO LIKE, SUBSCRIBE, AND COMMENT BELOW!

⭐ Produced by Icons of Real Estate – iconsofrealestate.com

In this episode of the Better Agent Podcast, host Josh Lavik sits down with Ann, a fellow Wisconsin real estate veteran with 20 years of experience. Ann shares her unique journey, transitioning from retail and property management into a successful real estate sales career.

Ann explains how her "crash course" in property management gave her an incredible advantage as an agent. From understanding strict FHA housing codes and landlord-tenant laws to running interference between cranky tenants and navigating the eviction process, Ann knows exactly what to look for in a property. Josh and Ann also discuss the power of subtle branding, the art of striking up a real estate conversation in the grocery store checkout line, and why agents need to stop judging potential clients based on their appearance or price point.

🎧 Hosted by: Josh Lavik

🎤 Featuring: Anne Yust

Anne Yust is a Broker with Homestead Realty, Inc., bringing more than 15 years of experience in the Wisconsin real estate market. She works with military families, homebuyers, and investors across the Racine and Kenosha metropolitan areas.

💡 What You’ll Learn in This Episode:

✔️ The Property Management Edge: How managing properties and dealing with code violations makes you a better advocate for buyers and sellers.

✔️ Mastering FHA Guidelines: Why knowing the nitty-gritty details of FHA and VA housing rules will save your deals from falling apart.

✔️ The Art of the "Clincher": How to naturally bring up real estate in everyday conversations (without being pushy or salesy).

✔️ Wear Your Brand: Why a simple branded jacket, name tag, or clever t-shirt is the easiest way to generate organic leads.

✔️ Finding Your Niche on Social Media: How Ann uses her passion for rose gardens and landscaping to connect with first-time homebuyers.

✔️ Don't Judge a Book By Its Cover: Why treating everyone with respect, regardless of their appearance or budget, is the key to building a sustainable business.

🎙 Connect with Anne Yust:

📘 Facebook → https://www.facebook.com/agentforeveryone

📷 Instagram → https://www.instagram.com/agentforeveryone

🔗 LinkedIn → https://www.linkedin.com/in/anne-catherine-yust-agentforeveryone07b3168/

🎙 FOLLOW JOSH LAVIK & THE BETTER AGENT PODCAST:

🌎 Website → https://www.joshlavik.com/

📘 Facebook → https://www.facebook.com/joshlavikassoc

📷 Instagram → https://www.instagram.com/jla_madison/

🔗 LinkedIn → https://www.linkedin.com/in/jlavik

🔖 DON’T FORGET TO LIKE, SUBSCRIBE, AND COMMENT BELOW!⭐ Produced by Icons of Real Estate – iconsofrealestate.com

Host Josh Lavik sits down with Tiffany Drahonovsky, a real estate agent and investor based in the Greater Milwaukee area. Tiffany shares her unconventional entry into real estate—getting downsized from corporate sales right as COVID-19 shut the world down, only to dive headfirst into working for a massive real estate investing and wholesaling company.

Tiffany breaks down how she analyzes a property, her strategies for setting correct seller expectations, and how she uses high-level psychology to write winning offers for her buyers. Josh and Tiffany also dive into why it's critical to tie your real estate business to personal passions—whether that is traveling the world, booking ski trips in the Alps, or rescuing and saving dogs!

🎧 Hosted by: Josh Lavik

🎤 Featuring: Tiffany Drahonovsky, Lucky Dog Real Estate

Tiffany Drahonovsky is an award-winning real estate associate with Coldwell Banker Realty, serving Southeastern Wisconsin, including Milwaukee and Franklin. With nearly a decade of experience, she has been named Wisconsin Salesperson of the Year (2023 & 2024) by the Jason Mitchell Group, is a recipient of the Chairman’s Circle Award, and was recognized among the Top 500 agents in the Milwaukee MSA (2025) by Real Producers Magazine.

💡 What You’ll Learn in This Episode:

✔️ Transitioning from a corporate 9-to-5 to wholesaling "stinky" properties during COVID

✔️ Why real estate lessons are expensive, and how agents can help buyers avoid them

✔️ The psychology of pricing: Why list price is just a "strategic invitation"

✔️ How to write winning offers using odd numbers and FBI negotiation tactics

✔️ The importance of setting expectations for sellers when a home doesn't sell

✔️ Why "broker hopping" isn't always bad if you are seeking the right room for growth

✔️ How to tie your business goals to personal passions

🎙 Connect with Tiffany Drahonovsky:

📘 Facebook → https://www.facebook.com/tiffany.drahonovsky

📷 Instagram → https://www.instagram.com/tifunny72/

🔗 LinkedIn → https://www.linkedin.com/in/tiffanydrahonovsky/

🎙 FOLLOW JOSH LAVIK & THE BETTER AGENT PODCAST:

🌎 Website → https://www.joshlavik.com/

📘 Facebook → https://www.facebook.com/joshlavikassoc

📷 Instagram → https://www.instagram.com/jla_madison/

🔗 LinkedIn → https://www.linkedin.com/in/jlavik
🔖 DON’T FORGET TO LIKE, SUBSCRIBE, AND COMMENT BELOW!

⭐ Produced by Icons of Real Estate – iconsofrealestate.com

In this episode of The Better Agent Podcast, host Josh Lavik sits down with Terra Beaver, a top-producing agent based in the Castle Rock Lake and New Lisbon area of Wisconsin. Terra shares her unique journey from working as a drug and alcohol counselor to building a thriving real estate business. The conversation dives deep into the turning point of her career at the four-year mark, explaining how getting serious about a CRM and building a consistent follow-up cadence changed everything.

Josh and Terra also explore how to beat automated valuation algorithms with hyper-local market knowledge and how to build a profitable niche right in your own backyard. Finally, learn Terra's brilliant strategy of using preemptive "next steps" videos to calm client emotions during inspections and appraisals, ensuring smoother transactions from accepted offer to closing day.

🎧 Host: Josh Lavik

🎤 Guest: Terra Beaver, Real Estate Professional from New Lisbon, WI

Terra Beaver is a Real Estate Broker and co-founder of the Lakes Region Team at Fathom Realty in New Lisbon, Wisconsin. She specializes in waterfront and vacation properties throughout Central Wisconsin’s Lakes Region, including the Castle Rock Lake and Lake Petenwell areas. Since 2014, Terra has closed more than 200 transactions and was recognized as a 2022 Top Producer by the South Central Wisconsin MLS.  

💡 What You’ll Learn:

✔️ How skills from a career in counseling perfectly translate into real estate success

✔️ Why local market expertise will always beat out automated online home values

✔️ The four-year turning point: How mastering a CRM took Terra's business to the next level

✔️ How to categorize leads and build a follow-up cadence so you never have to chase business

✔️ Finding your niche by leaning into the market that is already in your backyard

✔️ How to use proactive "next steps" videos to manage client emotions during inspections

🎙 Follow Terra Beaver:

📷 Instagram → https://www.instagram.com/petmommarealtor/

📘 Facebook → https://www.facebook.com/leavethehomeworktous/

🎙 FOLLOW JOSH LAVIK & THE BETTER AGENT PODCAST:

🌎 Website → https://www.joshlavik.com/

📘 Facebook → https://www.facebook.com/joshlavikassoc

📷 Instagram → https://www.instagram.com/jla_madison/

🔗 LinkedIn → https://www.linkedin.com/in/jlavik
🔖 DON’T FORGET TO LIKE, SUBSCRIBE, AND COMMENT BELOW!

⭐ Produced by Icons of Real Estate – iconsofrealestate.com

In this episode of The Better Agent Podcast, host Josh Lavik discusses how real estate professionals can achieve long-term success not only through consistency but also by connecting their business to a higher purpose. Joined by Jake Johnson, a seasoned realtor from Southern Wisconsin, the conversation explores how giving back through philanthropy can motivate agents during tough times. Jake shares his journey from starting in real estate to hitting the five-year milestone, offering insights into his growth, daily habits, and the power of building relationships. Learn how small, consistent actions and community involvement can lead to extraordinary results in the real estate world.

🎧 Host: Josh Lavik

🎤 Guest: Jake Johnson, Real Estate Professional from Johnson Creek, WI

Jake Johnson, known as “Jake with the Glasses,” is a top-producing REALTOR® with Real Broker based in Madison, Wisconsin. With just over five years in the industry, he has helped more than 100 families buy and sell homes across South-Central Wisconsin. 

💡 What You’ll Learn:

✔️ How philanthropy can drive your real estate business beyond profit

✔️ Why consistency is key in real estate, especially in the first five years

✔️ How to maintain focus on long-term growth while dealing with market ups and downs

✔️ The power of relationship-building and networking for career success

✔️ Jake’s personal tips on growing your business, from cold calling to leveraging video content

🎙 Follow Jake Johnson:

🌎 Website → https://www.jakeknowshomes.com/

📘 Facebook → https://www.facebook.com/JakeJohnsonKellerWilliams

🔗 LinkedIn → https://www.linkedin.com/in/jake-johnson-37532722/

🎙 FOLLOW JOSH LAVIK & THE BETTER AGENT PODCAST:

🌎 Website → https://www.joshlavik.com/

📘 Facebook → https://www.facebook.com/joshlavikassoc

📷 Instagram → https://www.instagram.com/jla_madison/

🔗 LinkedIn → https://www.linkedin.com/in/jlavik

🔖 DON’T FORGET TO LIKE, SUBSCRIBE, AND COMMENT BELOW!

⭐ Produced by Icons of Real Estate – iconsofrealestate.com

Josh Lavik welcomes brokerage valuation and M&A advisor Norma Rawlings to break down how real estate brokerages are valued and how brokers can scale through acquisition instead of slow, one-agent-at-a-time recruiting.

They discuss cash flow multiples, agent value, luxury brokerage premiums, transition strategy, and why scale is increasingly necessary to compete. Norma also explains how a professional valuation becomes a growth roadmap — not just a number on paper.

If you’re serious about building enterprise value in your brokerage, this episode is essential listening.

🎧 Hosted by: Josh Lavik

🎙 Guest: Norma Rawlings

Norma Rawlings is a real estate professional with BrokerVMA and the co-author of The Complete Guide to Buying and Selling Real Estate Brokerages: 10 Steps to Success. She specializes in brokerage valuation, mergers, and acquisitions, helping firms navigate the financial and operational steps involved in successful transitions. Norma supports brokers and owners seeking clarity, structure, and strategic guidance throughout the brokerage sales process.

💡 Key Takeaways:

✔️ Valuations should educate — not inflate

✔️ Cash flow + agent count drive brokerage value

✔️ Transition strategy protects agent retention

✔️ Recruiting through acquisition accelerates growth

✔️ Scale improves tools, efficiency, and profitability

✔️ A formal valuation creates clarity and leverage

🎙 FOLLOW NORMA RAWLINGS

🌎 Website → https://brokervma.com/

🔗 LinkedIn → https://www.linkedin.com/in/norma-rawlings-00b089256/

🎙 FOLLOW JOSH LAVIK & THE BETTER AGENT PODCAST:

🌎 Website → https://www.joshlavik.com/

📘 Facebook → https://www.facebook.com/joshlavikassoc

📷 Instagram → https://www.instagram.com/jla_madison/

🔗 LinkedIn → https://www.linkedin.com/in/jlavik
🔖 DON’T FORGET TO LIKE, SUBSCRIBE, AND COMMENT BELOW!

⭐ Produced by Icons of Real Estate – iconsofrealestate.com