Ep 257 How VCs Think: Insights from Keshia Theobald-van Gent

In this episode, we sit down with Keshia Theobald-van Gent, a seasoned venture capital investor with deep expertise in fund economics, portfolio strategy, and founder alignment. Keshia shares her sharp insights into how today’s most successful VCs operate and what emerging fund managers and founders need to know to succeed in this dynamic ecosystem. Whether you're a founder seeking to better understand how VCs evaluate your startup, or an emerging fund manager preparing to launch your first fund, this episode is packed with actionable takeaways and deep industry wisdom. 🔍 Topics Covered: Keshia’s Career Journey: How her professional path has shaped her perspective on modern venture capital. What VCs Look For in Startups: The core criteria venture capitalists prioritize when evaluating investments—and how founders can align. Balancing Vision & Returns: How VCs manage the tension between financial ROI and founder vision. Key KPIs in Venture Investing: The metrics that matter and how startups should track and report them. Red Flags for VCs: Common early indicators of trouble in portfolio companies—and how to avoid them. Liquidity & Exits: How VCs think about liquidity events, secondary sales, and capital returns. Crafting an Investment Thesis: What goes into building a compelling thesis that attracts LP capital. Venture Capital & Family Offices: Trends shaping these increasingly collaborative relationships. Fund Economics Explained: Core differences between venture capital and private equity economics. Overlooked Fund Expenses: Hidden costs that new fund managers often miss. Reporting to LPs: How firms communicate performance, and what LPs actually care about. When Investments Go to Zero: Fund strategy, tax implications, and wind-down considerations. Lessons for Emerging Managers: Common pitfalls and best practices for first-time fund leaders. Founder Success Story: A candid look at one portfolio company’s journey and growth challenges. 💡 Bonus Insights (if time allows): How branding influences deal flow and VC visibility. One thing Keshia would change about the VC industry. How AI and automation are changing the game for VCs and founders alike. 📬 Connect with Keshia: To follow Keshia’s work or reach out for collaboration, connect with her on LinkedIn. 📌 Disclaimer: The views expressed in this episode are for educational and informational purposes only and do not constitute financial or investment advice. The views expressed are personal and do not necessarily reflect the views of any affiliated organizations. Such as the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.”

Episode Description: In this insightful episode, we sit down with Mohamed Ahmed—engineer-turned-founder, investor, and author—to explore the real mechanics of venture capital, startup life, and personal growth. Mo brings his unique perspective from launching a successful startup, exiting, and now advising others through the VC lens. Whether you're an entrepreneur, investor, or someone navigating your own career transition, this episode is filled with real talk, valuable frameworks, and unfiltered stories you won’t want to miss. What We Cover: Mo’s career journey: From big tech to startup founder to venture capitalist The truth about how VC really works behind the scenes How VCs and LPs think—and what most founders get wrong Media myths: What’s often misunderstood about startups and founders Balancing growth with personal life: Tips for maintaining perspective Mental wellness and leadership—why it matters more than ever Making the leap from employee to entrepreneur: Key mindset shifts The challenge of engineers becoming business leaders The emotional journey of selling your company—and what happens next Lessons learned after an exit: What no one tells you Future trends in entrepreneurship and venture capital The core message behind Mo’s book and how it can help you Key Takeaway: Success in entrepreneurship isn’t just about raising capital or scaling fast—it’s about aligning purpose, people, and personal growth. Connect with Mohamed Ahmed: 🔗 LinkedIn – Mohamed Ahmed 📚 Learn more about his book and upcoming projects [insert website or link if applicable] Subscribe & Follow: If you enjoyed this episode, please rate and review the show! Subscribe for more conversations at the intersection of business, technology, and personal transformation. Disclaimer: The views and opinions expressed in this episode are for informational purposes only and do not necessarily reflect the official policy or position of any affiliated organizations, employers (past or present), or the podcast host. This content is not intended to be and should not be construed as legal, investment, or professional advice. The views expressed are my own and do not necessarily reflect the views of Finalis Inc. or Finalis Securities LLC, Member FINRA/SIPC.

In this episode, Shawn sits down with John Bisack, an experienced operational strategist and advisor who specializes in helping private equity-backed companies navigate the critical post-acquisition phase. With a background in transforming businesses for profitability, growth, and long-term scalability, John brings deep insights into what it really takes to deliver on the promises of a private equity deal—beyond the closing table. Disclaimer: The content in this episode is for informational purposes only and does not constitute financial, investment, or legal advice. Always consult with qualified professionals before making business decisions. 🎧 What You’ll Learn: A behind-the-scenes look at what happens after a company is acquired by a PE firm The biggest operational and cultural challenges businesses face post-acquisition How John identifies inefficiencies and aligns with PE growth expectations The difference between value delivered vs. services performed—and why that distinction matters Real-world insights into change management, KPI tracking, and pricing strategy 🔍 Topics Covered: Post-acquisition integration and value creation Operational due diligence and strategic alignment Cost efficiency without compromising growth Building leadership alignment and managing expectations PE investor communications and performance reporting Long-term strategies for maximizing valuation at exit 📌 Guest Links: 💼 LinkedIn: John Bisack

In this episode, Shawn sits down with Paul Adler, a veteran strategist in global revenue growth and a trusted advisor for companies entering the complex world of Federal Government markets. With decades of experience guiding businesses through the intricacies of federal contracting, Paul shares practical insights, battle-tested strategies, and hard-won lessons for founders and executives ready to scale through government channels. Whether you’re a startup looking for your first pilot program, or a scaling company considering the government as a strategic customer, this episode offers the clarity and context you need to succeed. 🎧 What You’ll Learn: Why the Federal Government "market" is very different from a government “contract” What makes the U.S. Government a unique and relationship-driven buyer Why commitment and focus are non-negotiables when entering this space The best first steps a company should take—and the common mistakes to avoid How to think about networking, certification, and timing in your market entry Why subcontracting often beats aiming for the "prime" position from day one A real-world success story of an entrepreneur who pivoted to win federal business The truth about lobbyists, political shifts, and procurement dynamics 🔍 Topics Covered: Strategic entry points into government markets Building trust and brand in a relationship-first ecosystem Targeting decision-makers and navigating procurement The role of mentors and proven success stories in early wins Long-term thinking in a highly regulated, highly competitive environment 📌 Guest Links: 🌐 Website: www.thepauladler.com 📧 Email: linkedin.com/in/pauladler1

In this episode, we’re joined by Stan Christensen, a veteran dealmaker, negotiation expert, and founder of Arbor Advisors. With over two decades of experience teaching negotiation at Stanford University and leading high-stakes transactions in the tech world, Stan offers a masterclass in how to navigate complex deals, align incentives, and come out ahead—whether you're raising capital, selling your company, or simply trying to keep a negotiation from falling apart. Stan shares his career-defining moments, hard-earned insights from the front lines of investment banking, and why most founders misunderstand who really does the work behind the scenes. This is a must-listen for entrepreneurs, operators, and anyone who wants to become a better negotiator. 💡 Topics Covered Stan’s journey from educator to investment banker The single biggest myth about great negotiators Advice for founders raising venture capital (hint: think twice) Why the best companies are sold—not bought How to renegotiate the preference stack and protect your payout Tactics to keep a counterparty at the table when they threaten to walk What separates good negotiators from bad ones Choosing the right investment banker (and what red flags to avoid) Are lawyers actually good negotiators? A behind-the-scenes look at a $70M deal that started with a $15M offer Stan’s favorite negotiation books, movies, and frameworks 📚 Recommended Resources Influence by Robert Cialdini How to Know a Person by David Brooks Film: 12 Angry Men 🔗 Connect with Stan Listen to Stan's Podcast All Things Negotiation - Podcast - Apple Podcasts Stan Christensen on LinkedIn

Episode Overview Today’s guest is Shalabh Gupta, a visionary entrepreneur and the CEO of a publicly traded company. With deep experience in both public and private markets, Shalabh brings a mission-driven mindset to solving complex problems through innovation. In this episode, he shares his journey to the public markets, lessons learned from operating in the spotlight, and what it really takes to drive long-term shareholder value while staying true to your company’s core mission. Whether you’re a founder, investor, or aspiring public company executive, this conversation is packed with insights into what it means to lead boldly in the public eye. 💡 What You’ll Learn Why Shalabh chose to take his company public earlier than most The tradeoffs between staying private vs. going public Insights into IPOs, SPACs, and reverse mergers — and why his company took its specific route The biggest surprises and challenges of running a public company How to prepare for shareholder meetings (including the hardest questions he’s been asked!) Strategies for balancing quarterly pressures with long-term vision What it takes to personally transition from private leadership to the public stage The core mission of his company — and why it matters now more than ever Advice for future public company CEOs What’s next for Shalabh’s company and how you can follow the journey 🔗 Connect with Shalabh 📍 LinkedIn – Shalabh Gupta

Rahul Pangam — Entrepreneur, AI Strategist, and Founder 🎧 Episode Overview: In this episode, we’re joined by Rahul Pangam, a seasoned entrepreneur and AI leader who successfully built and exited a company during its Series B round. Rahul takes us through the pivotal moments of his entrepreneurial journey — from raising capital to navigating a strategic sale — and shares his deep insights on how AI is reshaping industries, businesses, and the future of work. This candid conversation covers the evolving dynamics between humans and AI, what businesses need to do to stay competitive, and the most common missteps leaders make when adopting new technologies. 📝 Discussion Topics: ✔️ Rahul’s Entrepreneurial Journey — From Silicon Valley to AI leadership ✔️ Navigating a Raise-to-Sale Conversation at Series B ✔️ The Biggest Differences Between the Pre-AI and Post-AI World ✔️ Where Humans Still Outperform AI ✔️ How AI Can Benefit Traditional Industries Slow to Adopt Technology ✔️ Ways AI Can Level the Playing Field for Small Businesses ✔️ AI Readiness: How Companies Should Assess and Prepare ✔️ Common Mistakes in AI Integration and How to Avoid Them ✔️ Measuring ROI on AI Investments ✔️ AI’s Role in Global Geopolitics, Deep-Tech, and Economic Shifts 🎙️ Who Should Listen: Startup founders and entrepreneurs Business leaders exploring AI adoption Investors and venture capitalists Tech professionals and AI enthusiasts Anyone interested in startup exits and digital transformation 📌 Connect with Rahul Pangam: LinkedIn Profile

In this episode, we sit down with Manish Patel, whose career has spanned Google, venture investing, and product innovation. From playing a pivotal role in scaling transformative products like AdWords and Google Maps to shaping Silicon Valley’s startup ecosystem, Manish brings invaluable insights from the front lines of technology, entrepreneurship, and venture capital. Listeners will hear about his inspiring journey — from growing up in a family business to navigating the world of big tech and early-stage investing — and get practical advice on building startups, raising Series A rounds, and preparing for the future of business. 📝 Discussion Topics: ✔️ Lessons from Manish’s Early Career and Leadership Journey ✔️ How OKRs (Objectives and Key Results) Powered Google’s Growth ✔️ The Role of Luck, Timing, and Preparation in Career Success ✔️ Why Series A Funding Is a Make-or-Break Moment for Startups ✔️ The Biggest Trends and Disruptions Shaping the Next Decade ✔️ Practical Advice for Founders Navigating the Venture Capital World 🎙️ Who Should Listen: Startup founders and entrepreneurs Early-stage investors and venture capitalists Tech enthusiasts and product managers Anyone curious about how world-changing products and companies are built

In this episode of The Silicon Valley Podcast, we sit down with Tom Eggemeier, CEO of Zendesk, to discuss the transformative power of AI Agents, the evolving landscape of M&A, and the future of customer experience. Tom shares his insights on how businesses can leverage AI to drive growth, the decision-making process behind strategic acquisitions, and what’s next for Zendesk. What You’ll Learn in This Episode: ✅ AI Agents vs. Traditional AI – What sets them apart and how they’re reshaping customer service. ✅ The Role of AI in Business Growth – How AI can enhance both customer and employee experiences. ✅ M&A Strategy at Zendesk – The company’s approach to acquisitions and lessons from past deals. ✅ AI's Impact on Competitive Advantage – Will AI adoption create stronger moats or increase disruption risks? ✅ Zendesk’s Future Vision – What innovations are coming and where the company is headed in the next decade. Key Questions We Discuss: 🔹 How are AI Agents revolutionizing customer service, and how do they differ from traditional tools? 🔹 What are some real-world examples of businesses benefiting from AI adoption? 🔹 How can businesses balance AI-driven efficiency with personalized customer experiences? 🔹 What metrics should companies track to measure AI's impact on operations? 🔹 What’s Zendesk’s M&A playbook, and how does it guide acquisition decisions? 🔹 How can AI enhance the employee experience, not just the customer experience? 🔹 What groundbreaking innovations is Zendesk unveiling at Zendesk Relate? 🔹 What’s Tom’s vision for the next 5-10 years in AI and customer service? 🔹 How does a CEO continually adapt and grow in a fast-changing market? Connect with Tom Eggemeier & Zendesk: 🔗 Tom’s LinkedIn 🔗 Zendesk Website Email: [email protected]

In this episode of The Silicon Valley Podcast, we sit down with Cameron Herold, a world-renowned business leader, entrepreneur, and the mastermind behind the explosive growth of 1-800-GOT-JUNK?, where he scaled the company from $2 million to $106 million in just six years. From launching businesses as a teenager to coaching top CEOs—including Kimbal Musk—Cameron has mastered the art of scaling operations, creating high-performance cultures, and driving business success. He’s also the founder of COO Alliance, the only peer group dedicated to helping Chief Operating Officers excel in their roles. What You’ll Learn in This Episode: ✅ How Cameron transformed 1-800-GOT-JUNK? into a global brand ✅ His Sunday Night Planning Method for a productive week ✅ The DORAGI Coaching Framework and its impact on leadership ✅ The secret behind Vivid Vision and how it fuels business growth ✅ How to delegate effectively without micromanaging ✅ The TORC Hiring Method to ensure you build an A+ team ✅ The power of daily huddles in maintaining team alignment ✅ Real-life strategies for handling workplace conflict and fostering company culture Cameron also shares actionable insights on project management, hiring strategies, and leadership development, making this episode a must-listen for entrepreneurs, executives, and anyone looking to scale a business effectively. Resources & Links: 🔗 Connect with Cameron: CameronHerold.com 🔗 Learn more about COO Alliance: COOAlliance.com If you're looking for proven leadership strategies to take your company to the next level, you won’t want to miss this episode!