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. 1d ago

    Jake Cronin: Raising $75M for Field AI, The Cutco Origin Story & Why In-Person Sales Wins

    Jake Cronin is the co-founder and CEO of Siro, an AI conversation intelligence platform backed by $75M+ on a mission to turn face-to-face field sales into a data-driven, upwardly mobile career path.In this episode, Zach Schofel sits down with Jake to explore how Siro is unlocking the massive "black box" of in-person sales. Jake details his journey choosing a $15 Cutco knife selling gig over working at Hershey Park, learning the raw grit of door-to-door referral marketing, and later working at McKinsey before launching Siro. He breaks down why technical founders should never write code before pre-selling Figma prototypes to real customers, how real-time mobile AI coaching transforms field conversion rates, and why in-person sales is the ultimate disruption-proof career in the age of AI. They also dive deep into scaling a 105-person team 100% in-office in New York City, recruiting mechanics, and fundraising strategy.IN THIS EPISODE, YOU'LL LEARN:The Pre-Sell Framework: Why engineering founders must validate demand with interactive prototypes before building software. Unlocking the Field Black Box: How real-time mobile AI recording brings the same transparency to physical sales that Gong brought to Zoom.The AI Disruption Shield: Why face-to-face human interaction remains the most resilient economic skill set against AGI.In-Person Talent Scaling: How Siro scaled to 105 team members in NYC and built an internal talent machine that closes 89% of offers.CONNECT & TRACK THE FOOTPRINT:🎙️ Catch all episodes & deep dives: theunordinaryspod.com📺 Subscribe on YouTube: https://www.youtube.com/@UnordinarysPod📲 Follow Zach Schofel on LinkedIn: https://www.linkedin.com/in/zachschofel/

  2. Jul 20

    Michael Feldman: Bootstrapping a $29M Real Estate Moat, M&A Horror Stories & The Boring Business Arbitrage

    In this episode, Zach Schofel sits down with Michael to map out the real, unvarnished blueprint for building and scaling a service business from scratch all the way to a massive exit. Michael shares his wild origin story, pivoting from scouting movie locations for Hollywood studios to reading "Real Estate for Dummies" on a Jersey futon after the 2008 crash.Together, they break down why ambitious operators should skip the trendy startup hypes and focus on unglamorous, highly defensive recurring revenue instead. Michael also pulls back the curtain on the hard lessons he learned rolling up competitor agencies, sharing his exact M&A playbook and explaining why fully integrating acquired brands is usually a trap. They dive into the day-to-day mechanics of condo, co-op, and multifamily rentals, the math behind private equity roll-ups, and what it actually takes to partner with enterprise giants like Associa Corp. In this episode, you’ll learn: The Boring Business Arbitrage: Why staying away from hyper-competitive, trendy industries and hunting for unglamorous recurring revenue is the ultimate wealth hack. The M&A Integration Framework: Why full brand mergers trigger instant customer and employee churn, and how to execute a clean, margin-saving hybrid integration model instead. Rental vs. HOA Cash Flow Primitives: The deep operational divergence between managing high-overhead multifamily rentals and capitalizing on high-margin asset transfers. Talent Acquisition via Sliver Equity: How capital-constrained first-generation founders can weaponize equity incentives to lock in elite leadership without burning near-term cash.

  3. 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.

  4. 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

  5. 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]

  6. 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.

  7. 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

  8. 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

  9. 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.

  10. 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.

  11. 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.

  12. 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.

  • 12 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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