F*ck-up Fridays

Luz Ramirez predicted exactly what would happen when leadership slashed her department in half: families waiting nine hours, staff working until midnight, total chaos. She documented it, warned her boss, and was told "we've got your back." Then her supervisor went on live TV and said she had no idea what happened and ultimately blamed Luz. In this episode, she shares how that public...

Owen Mecham spent 24 years building automotive software: selling over 25 million cars through systems he helped create at Carvana. Then a milkshake triggered trigeminal neuralgia, the most painful disease in medicine. Two brain surgeries later, Owen shares why he wouldn't trade that dark chapter, how losing everything before his honeymoon set up his entire career, and the mindset shift that le...

Kyle Karges has been in real estate for 18 years but his biggest lesson didn’t come from a win. After trusting a contractor for seven years, Kyle got burned… and discovered the real difference between trust and verify. In this episode, Kyle breaks down how he recovered without chasing revenge, how “default yes” transformed his partnerships and growth, and how he’s intentionally building a family b...

Io Sunwoo is an LA-based affordable housing developer using an infill-lot strategy to create dignified housing for seniors, foster-youth transitions, and workforce residents. In this episode, Io shares a recent (and expensive) mistake: delegating key lending and negotiation details to a partner, ignoring red flags, and getting pulled into an extension-and-sunk-cost spiral that ultimately killed th...

What happens when one “great” borrower turns into a multi-million-dollar liability? In this episode, I sit down with Steven Loewer, a veteran private lender and multifamily investor with over $200M in transactions, to unpack his most expensive mistake: getting too deep with a single borrower. What started as a handful of successful fix-and-flip loans quietly snowballed into nearly $5 million of ex...

Linda’s first week in America was unusual: new job, new city… and caught in the middle of a shootout while doing door-to-door sales. Hear how that then-21-year-old French grad student turned that “trial by fire” into the people skills and courage to scale into big multifamily. Follow her on LinkedIn: https://www.linkedin.com/in/linda-holtz-1493495a Or visit her site at https://married2realestate.c...

My guest today, Chad Choquette, is the classic visionary: jumps out of the airplane and figures out the parachute on the way down. That worked for Airbnbs and flips… until he tried it on a multi-million-dollar dream project to revitalize his town with mini-golf, pizza, and walking trails, but without operators or a real team. He had to eat a bunch of loss and his crash landing is packed with warni...

Tracy thought she’d built real, sellable assets… until a broker told her the only option was liquidation. The core mistake: creating busy, profitable jobs for herself instead of businesses with transferable systems, independence, and real enterprise value. Follow her on Instagram: @thetracygunn https://www.instagram.com/thetracygunn or on Facebook (https://www.facebook.com/thetracygunn/) Follow th...

If a boss has always told you where to be and when to show up, what happens when the boss disappears? Trevor Hicks breaks down the accountability gap that almost knocked him out – and how he fixed it! Formerly a Doctor of Physical Therapy, he's now embracing the entrepreneurial life.  Follow him on Instagram:  @trevor_ryan7 Watch his podcast "Thinking Outside the Bank" on Youtube:  h...

At 21, Matt Starobykhovskiy was on top of the world—fit, successful, and making multiple six figures. A few bad decisions later, he was sleeping in the trunk of his Tesla with his brother, broke and broken. In this episode of F*ck-up Fridays, Matt shares the truth about losing everything—money, pride, and direction—and how humility, faith, and the SubTo community helped him rebuild a life grounded...

Dustin Geroski thought he had his future figured out — until chiropractic school nearly broke him. In this episode, Dustin shares how walking away from the wrong path taught him discipline, momentum, and the courage to pivot hard. From dissecting cadavers to building a co-living real-estate business, hear how he turned a near burn-out into a powerful pivot — and how you can too. Dustin is laser fo...

Heidi Pliam wears many hats. By day, lawyer. Also by day, serial entrepreneur. But *also* by day, building a multifamily acquisitions team.  In today's episode, she shared why you should aim to fail fast while striving to leave everything on the field: striking that difficult balance between when to press on and when to tap out. She also had some insight and encouragement for those of us that...

Noah Armstrong has gone wider with creative finance than most of us. He's even bought a car subject-to. More recently, he picked up a golf tour business—complete with curveballs (or would that be shanks?) that come with taking over something that's out of the ordinary. In this chat, he opens up about the lessons he’s learned, the mistakes he’s had to eat, and why due diligence matters so m...

In the pilot episode of the new podcast, I'm joined by Kathie Sonner. She went from stay-at-home mom to entrepreneur, yoga studio owner, and doula, with a few detours through real estate and other ventures. Along the way, she faced real challenges, learned tough lessons, and experienced the highs of success. What stands out is her focus on community, personal growth, and learning to ask for he...