The SoCal Edge

Art Dicker and Alessandro Rinaldi

A podcast about the practical decisions behind growing a business in Southern California — capital, hiring, partnerships, exits, and leadership.

  1. Jun 17

    The Startup Metrics Most Founders Get Wrong, with Arman Zand

    In this episode of The SoCal Edge, Art Dicker sits down with longtime friend and fractional CFO Arman Zand to discuss the financial realities behind startup growth, fundraising, and scaling. Drawing on nearly three decades of experience working with venture-backed startups, Arman shares the mistakes founders repeatedly make, what investors actually care about, and why storytelling remains one of the most important skills a CEO can develop. Arman explains why commonly cited metrics like burn rate, customer acquisition cost, and gross margin are often misunderstood or calculated incorrectly. He also provides an insider's perspective on how venture capital firms evaluate opportunities, why VC fund life matters more than most founders realize, and how today's investors have shifted from "growth at all costs" to capital efficiency. The conversation also explores the impact of AI on startup investing, lessons from difficult layoff decisions, the dangers of "bad revenue," and practical advice for founders trying to scale responsibly. Throughout the discussion, Arman emphasizes disciplined hiring, financial clarity, and understanding the true drivers of business performance in the eyes of investors. Reach out to Arman: https://www.linkedin.com/in/arman/

    The Startup Metrics Most Founders Get Wrong, with Arman Zand

  2. May 13

    Why Founders Leave Millions on the Table When Selling Their Company

    In this episode of SoCal Edge, we sit down with technology and business transformation leaders Elisa Henry and Allen Kim to explore what founders should really be doing 18–24 months before trying to sell their company. Drawing on decades of experience in technology, AI, product management, and operational scaling, Elisa and Allen explain why many founders leave millions on the table during an acquisition process — often because the business is too dependent on the founder, lacks scalable systems, or has hidden technical and operational debt. The conversation dives into what sophisticated buyers and private equity firms are actually looking for during due diligence, including: Why “service businesses disguised as product companies” often receive dramatically lower valuationsHow recurring revenue and customer stickiness can significantly increase multiplesThe role of technical debt, legacy systems, and AI in modern M&A preparationWhy documenting processes and building a strong data room early can make or break a dealHow founders can reduce dependency on themselves before an exitThe importance of leadership development and aligning employee incentives during a sale processHow AI tools are accelerating due diligence and exposing operational weaknesses faster than ever beforeCommon mistakes founders make when trying to prepare for an acquisition too lateElisa and Allen also share practical insights from working alongside founders through emotionally difficult transitions, helping companies move from founder-led organizations into scalable, acquisition-ready businesses. If you’re a founder, executive, investor, or advisor thinking about growth, scalability, or eventual exit planning, this episode offers a highly practical look inside the realities of preparing a company for sale. #podcast #business #startup #AI #MandA #founders #technology #privateequity #entrepreneurship #SoCalEdge Connect with Elisa and Allen: https://www.linkedin.com/in/henryelisa/https://www.linkedin.com/in/allenwkim/

    Why Founders Leave Millions on the Table When Selling Their Company

  3. May 7

    Rethinking Breast Cancer Treatment, with MeCo Diagnostics CEO Adam Watson

    In this episode of SoCal Edge, we sit down with Adam Watson, co-founder and CEO of MeCo Diagnostics, a San Diego-based biotech startup developing the only clinically validated biomarker test designed to match breast cancer patients with anti-fibrotic therapy. Adam shares the remarkable journey from cancer biology PhD student to startup founder, explaining how his dissertation research evolved into a venture-backed company aiming to unlock what he describes as a “seventh modality” of breast cancer treatment. The conversation explores how MeCo Diagnostics is taking an unconventional approach to oncology by repurposing existing anti-fibrotic drugs rather than developing entirely new therapies — with the potential to dramatically reduce both cancer recurrence and treatment costs. We also dive into: Why the economics of cancer treatment are becoming unsustainableThe challenges of fundraising as a diagnostics companyHow biotech founders tailor pitches differently for VCs, angels, and family officesThe realities of leaving academia and becoming a first-time CEOLessons learned from building a biotech startup with limited capitalThe role EvoNexus and the San Diego biotech ecosystem played in the company’s growthFounder loneliness, impostor syndrome, and the pressures of startup lifeWhy Adam believes many people underestimate how difficult entrepreneurship really isThis episode offers a candid look at the intersection of biotech innovation, healthcare economics, and startup building — from someone trying to fundamentally rethink how cancer care is delivered. Reach out to Adam: https://www.linkedin.com/in/adam-watson-phd/

    Rethinking Breast Cancer Treatment, with MeCo Diagnostics CEO Adam Watson

  4. Apr 9

    Healthcare AI Beyond the Demo: Trust, Workflow, and the Future of Digital Health

    In this episode of SoCal Edge, we sit down with Sunny Webb, a veteran AI product leader with more than 30 patents and deep experience across Apple, Pager Health, and healthcare AI standards, alongside Wei Li Tan, partner at Informed Ventures focused on early-stage digital health. Together, we unpack one of the biggest questions inhealthcare today: what actually happens after the AI demo ends? From clinical workflows and trust frameworks to investorexpectations, data moats, go-to-market strategy, and the future of payer and pharma AI, this conversation goes beyond the hype and gets into what it really takes to build scalable AI products in healthcare. Whether you’re a founder, investor, operator, or simply interested in where healthcare technology is headed, this episode offers a sharp look at the opportunities and risks shaping the next wave of digital health innovation.

    Healthcare AI Beyond the Demo: Trust, Workflow, and the Future of Digital Health

  5. Mar 30

    Investing in Large San Diego Real Estate Deals | Sumeet Parekh

    In this episode of The SoCal Edge, Art Dicker and co-host Alessandro Rinaldi sit down with Sumeet Parekh, founder and managing partner of HP Investors, to discuss the current state of the San Diego commercial real estate market. Sumeet shares insights from his background in investment banking and private equity, including how those experiences shaped his approach to real estate investing. The conversation dives into how data drives investment decisions, how market trends are shifting across San Diego, and why location-focused strategies can outperform broader approaches. They also explore the impact of interest rates, the challenges facing commercial real estate post-COVID, the role of AI in the industry, and what’s really happening in downtown San Diego today — including why now may be the time to start leaning back in. 00:00 – Introduction to Sumeet Parekh and HP Investors02:00 – Lessons from investment banking and private equity04:00 – How data drives real estate investment decisions07:00 – Balancing risk, diversification, and local market focus10:00 – The current impact of AI on real estate12:00 – How real estate deals are sourced and executed15:00 – The state of commercial real estate and capital markets18:00 – What’s happening in downtown San Diego today20:00 – The future of San Diego real estate and development strategy About the Podcast The SoCal Edge features conversations with founders, investors, and operators shaping the business and technology landscape across Southern California.

    Investing in Large San Diego Real Estate Deals | Sumeet Parekh

  6. Mar 24

    Inside EvoNexus: How Top Startups Get Built, Funded, and Exit (with Gene Dantsker)

    How do top startups actually succeed—and why do most fail? In this episode, Gene Dantsker of EvoNexus breaks down the real mechanics behind startup success: from founder mindset to fundraising strategy to product-market fit. With nearly $6B in startup impact, EvoNexus offers a rare inside look at what works—and what doesn’t—in building high-growth companies. Gene shares how EvoNexus has helped launch nearly 300 startups, drive billions in funding and exits, and build one of the strongest innovation ecosystems in San Diego and Orange County. They go deep on what separates successful founders from the rest, how startups really get funded, and why most startups fail. Gene also breaks down EvoNexus’ unique model—free office space, world-class mentorship, and a “pay-it-forward” equity structure—and how it dramatically improves a startup’s odds. You’ll also hear real case studies—from medtech IPOs to billion-dollar acquisitions—and practical advice for founders looking to raise capital or join an incubator. If you're a founder, investor, or just interested in how startups actually succeed, this is a must-listen.

    Inside EvoNexus: How Top Startups Get Built, Funded, and Exit (with Gene Dantsker)

  7. Mar 17

    How Startup Founders Can Save Millions in Taxes with QSBS Trusts | Brian Lamb, Promissory

    In this episode of The SoCal Edge, Art Dicker and co-host Alessandro Rinaldi speak with Brian Lamb, founder and CEO of Promissory, a company helping startup founders maximize the tax benefits of Qualified Small Business Stock (QSBS) through specialized trusts. Brian previously co-founded Trust & Will, one of the leading venture-backed estate planning platforms, and after partiallyexiting the company began exploring how founders could better plan for liquidity events. That journey led him to discover how complex and expensive QSBS trust planning can be — and inspired him to build Promissory to simplify the process. The conversation covers how QSBS works, why founders can potentially save millions in taxes, when in a startup’s lifecycle this planning should happen, and how software-driven legal solutions are transforming areas traditionally dominated by expensive law firm processes. What You'll Learn • What QSBS (Qualified Small Business Stock) is and why it can eliminate millions in taxes• How QSBS trust “stacking” can multiply tax exemptions for founders• When founders should start planning for pre-liquidity tax strategy• How software is transforming complex legal processes• Key lessons Brian learned as a second-time founder Key Timestamps 00:00 – Introduction to Brian Lamb and Promissory02:00 – Leaving Trust & Will and discovering QSBS trusts04:00 – Turning a complex legal process into a software platform08:00 – What QSBS is and why it matters for founders11:00 – How QSBS trust “stacking” works14:00 – When founders should set up a QSBS trust18:00 – Lessons learned from building Trust & Will23:00 – The future of pre-liquidity planning for startup founders About the Podcast The SoCal Edge features conversations with founders,investors, and innovators shaping the startup and technology ecosystem across Southern California.

    How Startup Founders Can Save Millions in Taxes with QSBS Trusts | Brian Lamb, Promissory

  8. Mar 12

    Building an AI Executive Assistant for Families | Bill Lennon, CEO of Ollie AI

    In this episode of The SoCal Edge, Art Dicker and co-host Alessandro Rinaldi sit down with Bill Lennon, founder and CEO of Ollie AI, to explore how artificial intelligence is beginning to solve one of the most overlooked problems in modern life — the “mental load” of running a household. Bill shares his journey from studying neural networks under AI pioneer Robert Hecht-Nielsen, to founding multiple startups, and ultimately building Ollie AI, an AI-powered assistant designed to help families manage calendars, reminders, shopping, meals, and the countless invisible tasks of everyday life. The conversation also dives into the realities of building an AI startup today: navigating rapidly evolving technology, consumer go-to-market challenges, advice from legendary investor Vinod Khosla, and why San Diego may be an underrated place to build world-class AI companies. 00:00 – The idea behind Ollie AI and solving the “mental load” problem03:00 – Bill Lennon’s early exposure to AI and neural networks06:45 – Building and exiting a startup before returning to AI08:30 – Launching Ollie AI and pivoting toward family assistants13:00 – The challenges of acquiring users for consumer AI products18:00 – The risk of AI startups becoming features instead of companies22:00 – Advice from investor Vinod Khosla24:00 – Building a startup in San Diego

    Building an AI Executive Assistant for Families | Bill Lennon, CEO of Ollie AI
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Ratings & Reviews

5
out of 5
12 Ratings

About

A podcast about the practical decisions behind growing a business in Southern California — capital, hiring, partnerships, exits, and leadership.

Information

  • Creator
    Art Dicker and Alessandro Rinaldi
  • Years Active
    2025 - 2026
  • Episodes
    26
  • Rating
    Clean
  • Copyright
    © Art Dicker and Alessandro Rinaldi
  • Show Website
    The SoCal Edge