citybiz podcasts

Joseph DaGrosa, Jr., Chairman and CEO of Axxes Capital, is a veteran private equity investor with a successful track record across industries including aviation, insurance, real estate, and sports. As co-author of The Financial Advisor’s Guide to Private Investments, he highlights the industry’s shift beyond the traditional 60/40 portfolio toward greater adoption of private equity, credit, and real assets. His career — from turning around 248 Burger King franchises to scaling Jet Support Services Inc. and co-founding Quinn Residences — reflects a focus on operational excellence and transformative value creation. Today, DaGrosa is dedicated to democratizing access to institutional-quality private market opportunities through Axxes Capital, aiming to empower advisors and individual investors to participate more fully in the evolving private investment landscape.

In this episode, we welcome Nick Preusch, Tax Director at YHB, who brings over 15 years of tax and policy experience (including roles as an IRS revenue agent and attorney). Nick unpacks the newly proposed “Big Beautiful Bill”, calling it the most sweeping tax overhaul since the 2017 TCJA. He walks us through:Changes to overtime and tip taxation (e.g. tax-free overtime up to ~$12,500, new rules around tip income)Enhanced senior tax relief (raising exemptions, targeting Social Security income)Key business incentives: 100% bonus depreciation, full R&D expensing, and the permanence of the 20% QBI deduction for pass-through entitiesNew benefits tailored for specific industries (e.g. tip credits extended to salons/spas, accelerated deductions for manufacturers)Strategic planning moves: structural changes like converting to S-corporations, altering withholding, and leveraging §199A opportunitiesLegal and state policy risks, including disputes over “overtime” definitions and whether states will conform to or diverge from federal changesA major boost to SALT deductibility — raising the state & local tax deduction cap from $10,000 to $40,000 per returnNick emphasizes the importance of working with seasoned tax advisors (rather than relying on social media or AI alone) and preparing early to capture the full benefits of this evolving legislation.

In this episode, we sit down with Louis J. Rogers, Co-Founder & CEO of Capital Square, a vertically integrated real estate platform spanning DSTs, Opportunity Zone funds, development, operations, and REITs. Louis discusses how he built Capital Square from its 2012 roots into a powerhouse with nearly $8 billion in transaction volume, covering over 13,000 apartments across multiple states.He shares how the firm’s “Invest, Build, Manage” model underpins their approach, and how they’ve expanded beyond 1031 real estate exchange offerings into working in build-for-rent, modular housing, and Opportunity Zone developments. He also explains how their Capital Square Housing Trust (REIT) gives more flexibility to DST investors through selective UPREIT transactions, offering an exit path while preserving tax advantages.Louis speaks to their mission of balancing investor returns and community impact, highlights their advocacy in shaping policy around Opportunity Zones and real estate tax incentives, and describes how their infrastructure supports institutional and family office capital across acquisition, development, property management, and disposition.Tune in to hear the story behind Capital Square’s evolution, Rogers' guiding philosophy, and the opportunities he sees ahead in tax-advantaged real estate investing.

In this episode, we speak with Diane Yu, Co-Founder & CEO of TidalWave, an AI-powered mortgage startup that’s reimagining the lending process. Diane discusses her journey — from leading tech at Better and building the adtech firm FreeWheel to launching TidalWave — and shares how the company is using white-box AI to bring transparency, equity, and efficiency to mortgage underwriting and approvals. She dives into how their product SOLO helps both borrowers and loan officers, how they’ve integrated with Fannie Mae and Freddie Mac, and her vision for disrupting a traditionally manual-heavy industry.

In this episode, we sit down with Danny Jenkins, Co-Founder and CEO of ThreatLocker®, to explore the challenges and innovations shaping today’s cybersecurity landscape. With over two decades of experience—from ethical hacking to corporate network defense—Danny offers insight into how ThreatLocker’s zero-trust platform is helping organizations stay ahead of evolving threats.Topics include:The inspiration behind ThreatLocker and its founding missionThe company’s rapid growth trajectory and expansion into global markets, including the Middle EastHow ransomware tactics are changing (e.g. exfiltration-first strategies)Risks tied to software source and origin, plus practices for vetting and mitigating insider threatsDanny’s early days as an ethical hacker and how that influences his leadership todayCommon cybersecurity blind spots that many CEOs overlookFour essential cyber hygiene rules for organizationsThe promise—and peril—of AI in securityPractical steps individuals can take to stay safer onlineKey lessons from Danny’s career and how business leaders should approach cybersecurityJoin us to hear how ThreatLocker is redefining cybersecurity with a “default deny” mindset—and what that means for businesses and individuals alike.

David Bellini, CEO of CyberFOX and co-founder of ConnectWise, discusses his return to entrepreneurship and his mission to simplify cybersecurity for managed service providers (MSPs) and IT teams. After helping lead ConnectWise’s international expansion and its acquisition by Thoma Bravo, Bellini launched CyberFOX to address what he sees as an overcomplicated cybersecurity market. The company focuses on user-friendly, affordable solutions—particularly in Privileged Access Management (PAM)—to help organizations reduce risk from internal misuse and unauthorized access. Bellini notes that growing compliance and cyber insurance requirements are accelerating demand for PAM tools, though CyberFOX aims to go beyond checkbox compliance by building lasting, scalable solutions. Looking ahead, he predicts PAM will evolve to become more integrated with identity management and zero-trust frameworks, adapting to AI-driven environments and increasingly dynamic access patterns.

Zachary Streit, founder and president of Priority Capital Advisory, leads a boutique advisory firm that structures debt and equity solutions for middle-market and institutional real estate deals in the $20M–$200M range. With more than two decades of CRE experience and over $5B in closed financings, he emphasizes pairing capital access with accountability and value creation—particularly in underserved and high-need markets.