The Breakthrough with Stephen Husted

Hosted by Stephen Husted

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Aug 2026

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About the show

Welcome to The Breakthrough with Stephen Husted, the show that takes you behind the scenes with successful entrepreneurs, real estate investors, and other movers and shakers in the business world. In each episode, we'll sit down with our guests to explore their personal and professional journeys, including the challenges they've faced, the breakthrough moments that propelled them to success, and the strategies and tactics they've used to get there. Get inspired by new ideas and strategies and get to know our guests on a deeper level.

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60 recent

September 3, 2026Episode 8556 min

EP 85: America Needs to Bring Back the Starter Home | Dr. Skylar Olsen

In this episode, I sit down with Dr. Skylar Olsen, a housing economist, proptech expert, educator, and entrepreneur who spent 11 years at Zillow studying housing from the customer’s perspective. She shares what she learned about the complexity of buying a home and why helping people understand the housing market is just as important as having the data itself. We also talk about the new venture she’s building, which helps landowners redevelop their lots into communities of six to 10 smaller homes. Her goal is to create more options for people who want to become homeowners but can’t afford the traditional single-family home. A major focus of our conversation is the missing middle of the housing market. Dr. Skylar explains how the current market often serves renters and existing homeowners with significant equity, while leaving many potential first-time buyers without an affordable path to ownership. We also get into the challenges of actually developing this type of housing, including zoning, parking, construction costs, finding the right lots, and getting landowners, buyers, funders, and developers aligned. Finally, we discuss housing in the Bay Area, the impact of technology wealth and mortgage rates, cooperative housing, and why the built environment may need to change if communities want to remain accessible to the next generation. Stephen and Dr. Skylar talked about: 📌 Dr. Skylar's 11 years at Zillow and what housing data taught her 📌 Redeveloping single-family lots into six to 10-home communities 📌 The missing middle and the struggle to become a first-time homeowner 📌 The challenges of zoning, parking, construction, and development 📌 How landowners can benefit from upzoning instead of simply selling to developers 📌 San Jose, East Palo Alto, and the unique dynamics of Bay Area housing 📌 Cooperative housing, shared spaces, and creating more accessible paths to ownership Find Dr. Skylar‘s: LinkedIn: https://www.linkedin.com/in/skylar-olsen-9823aa53/ Follow Stephen on IG: ⁠⁠ ⁠⁠https://www.instagram.com/stephenhusted/ ⁠⁠ ⁠⁠Follow our Podcast on IG: ⁠ ⁠@thebreakthrough.podcast ⁠⁠ Connect on LinkedIn: ⁠ https://www.linkedin.com/in/stephenhusted/⁠ and YouTube: ⁠⁠ ⁠⁠https://www.youtube.com/channel/UCsdNkau-5DUE9rGUIHrpfXA⁠⁠

August 28, 2026Episode 8454 min

EP 84: Why Veldin Miskic Says: “You Should Focus on One Real Estate Market”

In this episode, I sit down with Veldin Miskic , a managing broker and top-producing real estate agent specializing in Cape Coral and Fort Myers, Florida. Veldin shares his journey from getting his real estate license in New York in 2015 with little mentorship to eventually moving to Southwest Florida and building a business around the Cape Coral market. Today, he's the managing broker at Pelican Vista Realty, which grew to 17 agents organically and reached the top 20 brokerages in Southwest Florida in less than a year. We talk about what makes Cape Coral such a unique market, including its canals, growing population, out-of-state buyers, second homeowners, short-term rentals, and new construction opportunities. Veldin also breaks down why he eventually stopped trying to cover such a large geographic area and focused almost entirely on Cape Coral, where 95% to 96% of his business now comes from. We also get into what separates a good agent from a great one. Veldin explains why putting the client's needs first, negotiating on their behalf, anticipating problems, and creating a smooth transaction are ultimately what create long-term trust and repeat business. For investors, we dive into Cape Coral's short-term rental market, new construction, rental demand, and the numbers buyers should understand before investing. We also discuss Florida's homeowner and flood insurance, including how costs can vary significantly depending on the property's location, age, and flood zone. If you're a real estate agent, investor, or someone interested in the Florida market, there's a lot to take away from this conversation. Stephen and Veldin talked about: 📌 Veldin's journey from New York real estate to Southwest Florida 📌 Why Cape Coral has become his primary market 📌 What makes Cape Coral attractive to buyers and investors 📌 Short-term rentals, snowbirds, and new construction 📌 Why focusing on one market can create a competitive advantage 📌 What makes a truly valuable real estate agent 📌 How experienced agents create smoother transactions 📌 Florida homeowner and flood insurance 📌 Using YouTube to attract out-of-state buyers 📌 Building a brokerage while buying back your time Find Dean‘s IG here: https://www.instagram.com/dean_pelicanvistarealty/ LinkedIn: https://www.linkedin.com/in/veldin-miskic/ Follow Stephen on IG: ⁠⁠ ⁠⁠https://www.instagram.com/stephenhusted/⁠⁠ ⁠⁠ Follow our Podcast on IG: ⁠ ⁠@thebreakthrough.podcast⁠⁠ Connect on LinkedIn: ⁠ https://www.linkedin.com/in/stephenhusted/⁠ and YouTube: ⁠⁠ ⁠⁠https://www.youtube.com/channel/UCsdNkau-5DUE9rGUIHrpfXA⁠⁠

August 21, 2026Episode 8355 min

EP 83: Is Real Estate Really Dead? Alex Bekeza on Finding Deals in 2026

There is a lot of noise in real estate right now. Cash flow is dead. BRRRRs are dead. There are no good deals left. But is that actually true? In this episode, I sit down with Alex Bekeza , a real estate lender and investor who has originated more than $300 million in DSCR loans, to talk about what is really happening in today's market and what successful investors are doing differently. Alex shares why he has moved away from "lipstick rehabs" and now looks for deals that make sense even after accounting for major mechanical improvements. We also talk about reserves, conservative ARVs, DSCR loans, appraisals, turnkey properties, and why understanding your numbers is more important than listening to the noise online. We also get into how AI tools like Claude and ChatGPT are helping investors analyze deals, review scopes of work, challenge appraisal reports, and make better decisions. And for newer investors, Alex shares why you don't need to chase every strategy at once. Instead, develop a buy box, focus on one strategy, and learn from people who are already doing it successfully. If you're trying to invest in today's market, this conversation is a good reminder that there is no perfect market. You need to understand your numbers, manage your risk, and be willing to take calculated shots when the right opportunity comes along. Stephen and Alex talked about: 📌 Why investors need to ignore the noise and focus on the numbers 📌 Moving beyond "lipstick rehabs" and planning for major CapEx 📌 DSCR loans, reserves, and managing risk 📌 Why conservative ARVs can make better deals 📌 How Alex found a $75K deal that appraised at $282,500 📌 Using AI to analyze deals and challenge appraisal reports 📌 Why new investors should develop a specific buy box 📌 The importance of building a team that understands real estate 📌 Why there is no such thing as a perfect market 📌 Learning when to say no and taking calculated risks Find Alex‘s IG here: https://www.instagram.com/alexbekezathebrrrrlender/?hl=en LinkedIn: https://www.linkedin.com/in/alexander-bekeza-1240a0a0/ Follow Stephen on IG: ⁠⁠ ⁠⁠https://www.instagram.com/stephenhusted/⁠⁠ ⁠⁠ Follow our Podcast on IG: ⁠ ⁠@thebreakthrough.podcast⁠⁠ Connect on LinkedIn: ⁠ https://www.linkedin.com/in/stephenhusted/⁠ and YouTube: ⁠⁠ ⁠⁠https://www.youtube.com/channel/UCsdNkau-5DUE9rGUIHrpfXA⁠⁠

August 15, 2026Episode 821 hr 24 min

EP 82: Why Successful Real Estate Agents Stop Chasing Trends | Tanner Helm

I sit down with Tanner Helm to talk about what actually drives growth in real estate, and why so many agents may be spending too much time chasing the latest trend instead of focusing on the fundamentals. Tanner shares how his career in title insurance and real estate marketing gave him a unique view into hundreds of agents' businesses. He saw agents doing more than 100 deals a year with surprisingly few systems, while the most successful agents consistently focused on the one, two, or three things that worked for them. That experience ultimately shaped one of his biggest business principles: more conversations with more people equals more business. We also get into the current world of real estate content, why Tanner refuses to simply copy trends, how AI is changing the pressure agents feel to create, and why authentic human connection may become even more valuable as automated content and outreach become more common. Tanner also opens up about a much more personal part of his journey. After leaving real estate, starting a business that failed, gaining significant weight, and finding himself in six figures of debt, he began documenting what was and wasn't working as he rebuilt his life. That experience eventually became part of the foundation for the business and coaching work he's doing today. If you're a real estate agent, entrepreneur, or business owner trying to figure out where to put your energy, this conversation is a reminder that you don't necessarily need another strategy. You may need to get better at the things that already work. Stephen and Tanner talked about: - Why Tanner refuses to copy real estate content trends - Building a brand around authentic ideas - What happens when other creators copy your content - Tanner's journey from title insurance into real estate - How working with hundreds of agents shaped his business philosophy - What the highest-producing agents consistently did - Why some agents doing 100+ deals had surprisingly few systems - Why more conversations can lead to more business - Whether real estate agents actually need social media - How AI is creating more pressure for agents - Why people are becoming tired of automated outreach - Why long-form content may be making a comeback - YouTube vs. short-form content - Tanner's growth coaching business - Sales, social media, and systems - Rebuilding after business failure and financial setbacks Find Tanner‘s IG here: https://www.instagram.com/tannerhelm/?hl=en LinkedIn: linkedin.com/in/tanner-helm-086ba4101 Follow Stephen on IG: ⁠⁠ ⁠⁠https://www.instagram.com/stephenhusted/ ⁠⁠ ⁠⁠Follow our Podcast on IG: ⁠ ⁠@thebreakthrough.podcast⁠⁠ Connect on LinkedIn: ⁠ https://www.linkedin.com/in/stephenhusted/⁠ and YouTube: ⁠⁠ ⁠⁠https://www.youtube.com/channel/UCsdNkau-5DUE9rGUIHrpfXA⁠⁠

August 6, 2026Episode 811 hr 1 min

EP 81: Sam Wegert's Co-Living Strategy Is Changing Real Estate

What if one of the biggest solutions to the housing crisis has been hiding in plain sight? In this episode, I sit down with Sam Wegert, entrepreneur, real estate investor, TEDx speaker, and co-living expert, to explore why shared housing could become one of the biggest opportunities in real estate over the next decade. We discuss how co-living creates affordable housing, stronger communities, and better cash flow while helping solve some of today's biggest social challenges. Before we dive into real estate, Sam opens up about one of the most difficult seasons of his life. He shares the heartbreaking loss of his sister, family health challenges, separation, and how those experiences completely changed his perspective on money, success, and what truly matters. It's one of the most honest conversations we've had on the podcast. We also discuss why so many entrepreneurs chase external validation, how hustle culture can lead to burnout, why community is becoming more valuable than ever, and how investors can use co-living to create both financial freedom and social impact. If you've ever wondered where the future of real estate is heading, or you're looking for a strategy that creates both profit and purpose, you'll enjoy this conversation. If you enjoyed this episode, I'd really appreciate it if you subscribed, left a review, and shared it with someone who would benefit from the conversation. Navigating grief, loss, and life's hardest seasons Why money doesn't always create happiness Escaping hustle culture without losing ambition The future of co-living Solving the affordable housing crisis Building community through shared housing Cash flow opportunities in co-living Choosing the right markets Regulations and challenges investors should know Why loneliness is becoming a modern epidemic Entrepreneurship and resilience The importance of redefining success Find Sam‘s IG here: https://www.instagram.com/samwegert/?hl=en LinkedIn: https://www.linkedin.com/in/samuelwegert/?skipRedirect=true Follow Stephen on IG: ⁠⁠ ⁠⁠https://www.instagram.com/stephenhusted/⁠⁠ ⁠⁠ Follow our Podcast on IG: ⁠ ⁠@thebreakthrough.podcast⁠⁠ Connect on LinkedIn: ⁠ https://www.linkedin.com/in/stephenhusted/⁠ and YouTube: ⁠⁠ ⁠⁠https://www.youtube.com/channel/UCsdNkau-5DUE9rGUIHrpfXA⁠⁠

July 24, 2026Episode 801 hr 11 min

EP 80: The AI Systems Justyn Berkovits Uses to Scale a One-Person Business

Everyone is talking about AI, but very few people are talking about how to use it in a way that actually improves your life. In this episode, I sit down with Justyn Berkovits, entrepreneur, AI educator, and content creator, to explore how artificial intelligence can become an extension of your thinking instead of replacing it. We discuss why AI is changing entrepreneurship forever, how solo founders can build systems that save hours every week, and why authenticity will become even more valuable as AI-generated content becomes more common. Justyn also shares his incredible personal story. After experiencing business failure, losing his job, and carrying significant debt, he rebuilt his life through content creation, entrepreneurship, and relentless consistency. Within a year, he went from uncertainty to buying his family's first home while growing a thriving personal brand. We also dive into mindset, perfectionism, dopamine, content creation, AI agents, Claude, ChatGPT, automation, personal branding, and why the people who embrace learning instead of chasing shortcuts will have the biggest advantage over the next decade. Buying a first home while welcoming their second child Recovering from business setbacks and financial challenges Why consistency beats talent in content creation Building a personal brand through authenticity Using AI to automate repetitive work Claude vs ChatGPT AI agents and business systems Building a second brain with AI Avoiding AI-generated content that sounds robotic The future of search with transcripts and AI Mental health, dopamine, and social media Creating a legacy through content Why entrepreneurs should embrace AI instead of fearing it If you're wondering how AI fits into your business or simply want to become more productive without sacrificing your authenticity, this conversation is packed with practical insights. If you enjoyed this episode, I'd really appreciate it if you subscribed, left a review, and shared it with someone who would benefit from the conversation. Find Justyn‘s IG here: ⁠ https://www.instagram.com/justyn.ai/ ⁠ LinkedIn: ⁠ https://www.linkedin.com/in/justynberkovits/ ⁠ Follow Stephen on IG: ⁠⁠ ⁠ ⁠⁠https://www.instagram.com/stephenhusted/⁠⁠ ⁠ ⁠⁠ Follow our Podcast on IG: ⁠ ⁠ ⁠@thebreakthrough.podcast ⁠ ⁠ ⁠⁠ ⁠ Connect on LinkedIn: ⁠ ⁠ ⁠ ⁠ https://www.linkedin.com/in/stephenhusted/⁠ ⁠ and YouTube: ⁠⁠ ⁠ ⁠⁠https://www.youtube.com/channel/UCsdNkau-5DUE9rGUIHrpfXA⁠⁠ ⁠

July 16, 2026Episode 7946 min

EP 79: The Real Estate Strategy Anson Young Has Used Since 2015

In this episode, I sit down with Anson Young to discuss how he built a successful real estate investing business by focusing on consistency instead of constantly chasing the next big strategy. Anson shares how a small direct mail campaign led to his first deal and why that same marketing approach continues to generate opportunities today. We also discuss why so many investors struggle with shiny object syndrome, how systems create long-term growth, and why building wealth often comes from mastering one strategy rather than jumping between many. Anson also shares practical insights on house hacking, scaling an investing business, and helping clients create financial freedom through real estate. How 250 letters led to Anson's first real estate deal Why direct mail still works in today's market Building a repeatable lead generation system The psychology behind successful marketing Avoiding shiny object syndrome Transitioning from flipping to long-term investing Why house hacking is ideal in expensive markets Helping clients build wealth through real estate Building systems before scaling a business Why consistency beats constantly changing strategies The future of ADU development and affordable housing If you enjoyed this episode, I'd really appreciate it if you subscribed, left a review, and shared it with someone interested in real estate investing, direct mail marketing, house hacking, or building long-term wealth. Find Anson‘s IG here: https://www.instagram.com/younganson/?hl=en LinkedIn: https://www.linkedin.com/in/ansonyoung/ Follow Stephen on IG: ⁠⁠ ⁠⁠https://www.instagram.com/stephenhusted/⁠⁠ ⁠⁠ Follow our Podcast on IG: ⁠ ⁠@thebreakthrough.podcast⁠⁠ Connect on LinkedIn: ⁠ https://www.linkedin.com/in/stephenhusted/⁠ and YouTube: ⁠⁠ ⁠⁠https://www.youtube.com/channel/UCsdNkau-5DUE9rGUIHrpfXA⁠⁠

July 2, 2026Episode 7855 min

EP 78: Travis Chappell on Podcasting, Relationships, and Building Wealth

In this episode, I sit down with Travis Chappell to discuss how podcasting became the foundation for building multiple businesses, meaningful relationships, and long-term opportunities. Travis shares how he went from door-to-door sales to becoming a full-time podcaster, entrepreneur, and business owner by consistently investing in relationships and taking action before he felt ready. We talk about why so many people get stuck waiting for the perfect time, how podcasting can accelerate personal and professional growth, and why building an audience before building a product can create incredible business opportunities. Travis also shares lessons from growing multiple podcasts, coaching entrepreneurs, and leveraging conversations to create lasting partnerships. Stephen and Travis talked about: 📌 Why taking your shot creates unexpected opportunities 📌 The dangers of waiting for the perfect moment 📌 How podcasting became Travis' full-time business 📌 Building an audience before building a product 📌 Growing from $50,000 to $400,000 in one year 📌 Why relationships are more valuable than followers 📌 Podcasting as a networking and business tool 📌 Sales, coaching, and overcoming rejection 📌 The long-term value of consistency 📌 How podcasting can help entrepreneurs grow their business 📌 Why podcasting is one of the best ways to learn from experts 📌 The importance of focusing on what you can control Whether you're building a business, growing your network, or thinking about starting a podcast, this conversation is packed with practical insights on taking action, creating opportunities, and playing the long game. If you enjoyed this episode, I'd really appreciate it if you subscribed, left a review, and shared it with someone interested in entrepreneurship, podcasting, business growth, or building meaningful relationships. Find Travis‘ IG here: https://www.instagram.com/travischappell/?hl=en LinkedIn: https://www.linkedin.com/in/travischappell/ Follow Stephen on IG: ⁠⁠ ⁠⁠https://www.instagram.com/stephenhusted/⁠⁠ ⁠⁠ Follow our Podcast on IG: ⁠ ⁠@thebreakthrough.podcast⁠⁠ Connect on LinkedIn: ⁠ https://www.linkedin.com/in/stephenhusted/⁠ and YouTube: ⁠⁠ ⁠⁠https://www.youtube.com/channel/UCsdNkau-5DUE9rGUIHrpfXA⁠⁠

June 25, 2026Episode 7755 min

EP 77 - How to Turn One House Into Multiple Streams of Income | Edmond Bondoc

In this episode, I sit down with Edmond Bondoc to discuss how he transformed a single-family property into a multi-unit investment through ADU development and strategic planning. Edmond shares the full story of finding the property, financing the project, navigating Seattle's permitting process, and preparing the units for long-term cash flow. We also discuss the opportunities available to investors in Seattle, the realities of development, and why having the right team can dramatically impact the success of a project. Edmond breaks down condoization, construction financing, and the lessons he's learned from building while simultaneously growing his family and planning for the future. Finding off-market development opportunities Turning one property into three income-producing units Building attached and detached ADUs Seattle's permitting and development challenges Common mistakes investors make during development Financing construction projects creatively Condoization and property separation strategies Why having the right architect and builder matters The importance of community and mentorship Building long-term financial freedom through real estate Why imperfect action beats perfect planning Creating wealth while planning for family and future goals If you enjoyed this episode, I'd really appreciate it if you subscribed, left a review, and shared it with someone interested in real estate investing, ADUs, development, or financial freedom. Find Edmond‘s IG here: https://www.instagram.com/edmondfromedmonds/ LinkedIn: linkedin.com/in/edmondbondoc Follow Stephen on IG: ⁠⁠ ⁠⁠https://www.instagram.com/stephenhusted/⁠⁠ ⁠⁠Follow our Podcast on IG: ⁠ ⁠@thebreakthrough.podcast⁠⁠ Connect on LinkedIn: ⁠ https://www.linkedin.com/in/stephenhusted/⁠ and YouTube: ⁠⁠ ⁠⁠https://www.youtube.com/channel/UCsdNkau-5DUE9rGUIHrpfXA⁠⁠ Stephen and Edmond talked about:

June 17, 2026Episode 7654 min

EP 76: From $90K in Student loan Debt to Financial Freedom | Craig Curelop

In this episode, I sit down with Craig Curelop to discuss how house hacking became the foundation of his journey to financial freedom, why he left Silicon Valley for Denver, and how real estate changed the trajectory of his life. Craig shares his path from working as an underwriter in Silicon Valley to joining BiggerPockets, writing The House Hacking Strategy , and becoming one of the most recognized voices in the house hacking space. Along the way, he reveals how he paid down debt, built rental income, became financially free, and grew a real estate business helping others achieve similar results. We also discuss why young people have a massive advantage when it comes to investing, the sacrifices required to build long-term wealth, and how real estate agents can use investing to create income beyond commissions. Craig explains why many people overcomplicate getting started and why action often matters more than perfection. Craig's journey from Silicon Valley to BiggerPockets Why house hacking became his path to financial freedom Turning $90,000 of student debt into opportunity The sacrifices young investors should consider making Writing The House Hacking Strategy Becoming financially free through rental properties Building a real estate business from the ground up Why real estate agents should become investors Long-term wealth versus short-term commissions Why getting started matters more than timing the market The conversation also covers entrepreneurship, public speaking, content creation, coaching, co-living investments, and why some of the best opportunities come from doing things others are unwilling to do. If you enjoyed this episode, I'd really appreciate it if you subscribed, left a review, and shared it with someone interested in house hacking, financial freedom, real estate investing, or building wealth through real estate . Find Craigs‘s IG here: https://www.instagram.com/craigcurelop/ LinkedIn: https://www.linkedin.com/in/craig-curelop-a6457242/ Follow Stephen on IG: ⁠⁠ ⁠⁠https://www.instagram.com/stephenhusted/⁠⁠ ⁠⁠Follow our Podcast on IG: ⁠ ⁠@thebreakthrough.podcast⁠⁠ Connect on LinkedIn: ⁠ https://www.linkedin.com/in/stephenhusted/⁠ and YouTube: ⁠⁠ ⁠⁠https://www.youtube.com/channel/UCsdNkau-5DUE9rGUIHrpfXA Stephen and Craig talked about: