Unordinary's Podcast with Zach Schofel

Zach Schofel
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  • Entrepreneurship
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I’m Zach Schofel, host of The Unordinary Podcast. Join me for unscripted conversations with people I admire about the things I’m most passionate about.I interview entrepreneurs, experts, and thought leaders to uncover the truth about success, pivotal mistakes, and real challenges! What it truly takes to be unordinary. You'll see an amazing episode every week. 🗓️ Premiere: January 13 featuring Mark Cuban. In our first episode, we dive into how Mark identifies 10-Xers and his "goat tax hedge" for real estate . Follow the journey. Click the follow button and leave a review.

Episodes

  1. Jun 30

    Eli Wachs: The AI Fraud Arms Race, King-Maker Capital & Exploding Enterprise Perception

    Eli Wachs is the co-founder and CEO of Footprint, an advanced, venture-backed trust layer combining identity verification, fraud detection, and AI-driven financial crime investigation into a single enterprise platform. In this episode, Zach Schofel sits down with Eli to pull back the curtain on global financial crime and the technical execution required to scale a B2B security engine. Eli charts his path from writing the original business plan in his Stanford dorm room to raising over $20M from Index Ventures and QED Investors. He unpacks how generative AI completely shattered traditional human-in-the-loop compliance models by allowing cartels to automate synthetic fraud factories at a massive scale. They dive deep into why founders must choose strategic "King-Maker" investors over inflated top-line valuations, how to handle high-friction board room alignment when freezing growth metrics, and the contrarian psychology behind leveraging massive conference footprints to secure Tier-1 enterprise accounts. In this episode, you’ll learn: The AI Fraud Arms Race: How generative software enabled cartels to scale synthetic identities, and why security must move from entry-point detection to automated AI case investigations. The Valuation vs. King-Maker Choice: The deep mechanics of strategic fundraising and why optimizing for systemic market amplification beats taking an inflated check every time. The 6-Month Growth Freeze: How to systematically align your board to accept flat near-term revenue to properly engineer your tech stack for massive regulatory market waves. Contrarian Team Design: Why splitting your company into distinct cultural silos—in-office sales vs. remote engineering—drives hyper-isolated execution velocity.

  2. Jun 15

    Dylan Gambardella: The Arbitrage of Corporate Longevity & Building Scrappy Tech Stacks

    In this episode, Zach Schofel sits down with his long-time childhood friend to discuss the deep mechanics of scaling high-performance cultures and disrupting traditional healthcare infrastructure. Dylan unpacks his foundational journey of launching NextGen HQ using bar mitzvah capital and scaling it to a 200,000-user workforce ecosystem, sharing the brutal mistakes he made along the way by over-engineering products in secret. They explore the ultimate "buy vs. build" internal hiring choices, the hidden financial math of self-insured corporate healthcare benefits, and why traditional 15-minute annual physicals are failing elite operators who want to stay in the business arena longer. In this episode, you’ll learn: The Bar Mitzvah Capital Playbook: How to harness early entrepreneurial grit, move fast, and learn directly from early systemic friction. The Product Launch Framework: Why shipping an engineering project at 95% readiness is critical to capturing immediate customer data loops. The Corporate Health ROI: The deep financial economics behind self-insured enterprise health strategies and scaling preventative care metrics. Wearable Trend Engineering: How to intelligently utilize continuous glucose monitors, rings, and sleep tech without generating tracking anxiety.

    Dylan Gambardella: The Arbitrage of Corporate Longevity & Building Scrappy Tech Stacks

  3. May 26

    Jonathan Buckelew: The AI-Native Real Estate Playbook & Ripping Out Legacy Software Moats

    Jonathan Buckelew is the co-founder of CRE AI Studio, an educational and consulting platform transforming how commercial real estate professionals deploy automation and advanced AI across their operations. In this episode, Zach Schofel sits down with Jonathan to uncover the operational realities of running a massive real estate portfolio with an ultra-lean team. Jonathan pulls back the curtain on his transition from an ex-CPA who hated public accounting to a private equity asset manager using Claude, custom AI memory structures, and autonomous agents to manage 75 properties. They dissect the deep operational friction caused by incumbent software gatekeepers, the classic "buy vs. build" dilemma, and how to effectively drive technology adoption with old-school, front-line site teams. In this episode, you’ll learn: The PE Insider Track: How a deep grasp of accounting fundamentals can be leveraged as an unfair operational advantage in real estate private equity. [00:06:56] The Adoption Protocol: Why software implementation fails on the front lines and how to secure genuine buy-in from legacy site teams. [00:31:53] Ripping Down the Moats: A transparent look at how incumbent Property Management Systems gatekeep asset data and why new startups are disrupting the ecosystem. [00:28:44] The Vibe Coding Blueprint: How a non-technical asset manager can leverage Claude and automated tools to build custom, production-grade tools for pennies. [00:41:51]

  4. May 5

    Cyrus Shirazi - Scaling Haven to $10M & The Obsession with Radical Responsiveness

    Cyrus Shirazi is the CEO and founder of Haven, a tech-forward accounting and financial services firm built on speed. After seeing his founder friends constantly ignored by traditional CPAs, Cyrus realized the industry didn't need better accountants—it needed better service.In this episode, Zach Schofel dives into Cyrus’s journey from scaling a dorm-room agency to managing hundreds of millions in AUM at Meow, and finally building Haven into a $10M ARR powerhouse in just 2.5 years. Cyrus breaks down his "obsession-first" approach to customer experience, why he manages his entire firm via Slack, and his ambition to build the PWC of the AI era.In this episode, you’ll learn:The Responsiveness Moat: How Haven uses custom Slack bots to ensure a sub-5-minute response time.Scaling Channels: The difference between the "hustle" required for $1M and the "compounding channels" needed for $100M.Founder Dynamics: The pros and cons of building a company with a best friend of 20 years.The Agentic Future: How Haven is using AI and OCR to automate bookkeeping and provide real-time financial reporting in natural language.

  5. Apr 21

    Isaac Kassab: The AI-Native Talent Revolution & The Arbitrage of Hunger

    Isaac Kassab is the co-founder of Pearl Talent, an AI-native staffing company that is redefining how startups scale without legacy overhead. In this episode, Zach Schofel sits down with his close friend to discuss the "arbitrage of hunger" and why the next generation of A-players is coming from Latin America and Asia. Isaac reveals the "Six Whys" vetting process, the mandatory AI School every Pearl hire must pass, and why he believes "managed services" are the only way to ensure 95% retention in a distributed workforce. In this episode, you’ll learn: The Vetting Hack: How to identify an A-player by finding their intrinsic motivation. The AI School: Why Pearl puts every candidate through 6 weeks of AI training before they can be hired. The ROI of Talent: Why you should stop looking for the cheapest overseas labor and start looking for the "cracked out" 1% .Lockstep Partnerships: Tips for building an honest, high-trust relationship with a co-founder

  6. Apr 1

    Yaakov Zar - Scraping a $110M Brokerage for an AI Future

    In this episode, Zach Schofel sits down with Yaakov to discuss the "hardcore truth" of pivoting from a billion-dollar brokerage to a pure AI software company . Yaakov shares how he transitioned from a non-engineer to committing code daily and why he believes every team member must become "technical" in the age of AI. Yaakov Zar is a serial entrepreneur and the CEO of Lev, a commercial real estate platform bringing transparency and AI-driven speed to a trillions-of-dollars industry. In this episode, you’ll learn: The Power of the Pivot: Why Yaakov scrapped a high-growth brokerage model to follow his heart as a "software guy". AI Implementation: How Lev uses AI to turn 10-hour board updates into 10-minute tasks. The Horizontal Org: Why Yaakov limits his team to 30 people and how he manages 15+ direct reports using agentic tools. Perspective & Purpose: A raw look at what really matters after tragic loss, and how to balance building a tech giant with raising a family and serving community.

    Yaakov Zar - Scraping a $110M Brokerage for an AI Future

  7. Mar 7

    Taylor Prokes: Scaling the Big Ass Calendar & Radical Outreach Strategies

    Taylor Prokes is the co-founder and CEO of the Big A## Calendar and the creative engine behind Jesse Itzler’s portfolio of brands . In this episode, Zach Schofel dives into the "unordinary" life of a founder who went from a finance degree to living in a Jeep, to running 100-mile ultra-marathons. Taylor shares the exact blueprint she used to get on Jesse Itzler’s radar, making 100 videos in a single year and how that evolved into a partnership that has seen the Big Ass Calendar grow by 60% year-over-year. In this episode, you’ll learn: The "No Ask" Outreach: How to build a relationship with someone you admire by providing value and entertainment for a year before asking for anything . Planning for Legacy: Why Taylor believes you should schedule your life's adventures before your work meetings. The Resilience of an Ultra-Runner: What rim-to-rim-to-rim in the Grand Canyon taught Taylor about grit and surviving when you're "dead after four hours". The Hard Truth of Scaling: Lessons from moving 60,000 units in two months and managing the "fires" that come with rapid growth.

  8. Feb 11

    Ben Sharf: From Boarding School to Building Platter

    In this episode of The Unordinary Podcast, Zach sits down with Ben Sharf, Co-Founder & CEO of Platter for a raw conversation about ambition, risk, and living your own truth. Ben shares the unconventional path that led him from boarding school at 15, to Division I hockey at Colgate, to walking away from a consulting job the night before it started all to bet on himself. They dive into: • Why athletes often become elite operators• The moment Ben chose entrepreneurship over stability• Building Platter into a billion-dollar GMV ecosystem• How to actually set uncomfortable goals (and reverse engineer them)• The reality behind Forbes 30 Under 30• What a 10-day silent meditation retreat teaches you about ego, chaos, and clarity This episode is about more than business, it’s about identity, ambition, and having the courage to choose your own path. Inside the minds of doers and builders.

  9. Feb 4

    Or Bokobza: Grit, The Future of Property Brands

    Or Bokobza is a "rockstar" who recently closed a $55M raise, but his journey started in a small Moshav in Israel and 10 years in the elite special forces . Today, as CEO of Ven, he is helping the world’s biggest property owners turn "buildings into brands.". In this deep dive, Or and Zach discuss the "glass-eating" reality of startups, the "purge" coming for sales-led tech companies, and why the word "tenant" should be retired forever. Follow the pod for more Unordinary stories.

  10. Jan 13

    Mark Cuban: Hiring and Investment Insights

    Hosted by Zach Schofel (Co-founder of Cosign) and Phillip Newsom (Head of Operations), we dive into the raw truth behind scaling companies, building high-performing cultures, and practical. No fluff, just the real grit of entrepreneurship.

  • 10 Episodes

About

I’m Zach Schofel, host of The Unordinary Podcast. Join me for unscripted conversations with people I admire about the things I’m most passionate about.I interview entrepreneurs, experts, and thought leaders to uncover the truth about success, pivotal mistakes, and real challenges! What it truly takes to be unordinary. You'll see an amazing episode every week. 🗓️ Premiere: January 13 featuring Mark Cuban. In our first episode, we dive into how Mark identifies 10-Xers and his "goat tax hedge" for real estate . Follow the journey. Click the follow button and leave a review.

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