This week’s episode explores one of the most pressing challenges early-stage startups face: competing against well-funded incumbents. We cover how startups can beat giants by focusing on niche markets, iterating fast, building emotional brands, and providing world-class customer experiences. This is the ultimate guide for founders navigating a David vs. Goliath scenario. Whether you’re bootstrapping or just closed your seed round, these tactics will give you the edge. A friendly heads up - this episode is our season closer before we take a pod break for the summer. Thanks for listening and enjoy your summer - we’ll be back from a new studio, recharged and ready to roll.

⏱️ Chapter Markers

00:00 – Intro and Summer Break Announcement

01:00 – Why Competing with Big Players is Tough But Doable

02:30 – Foundational Assumptions Before Competing

04:00 – Strategy #1: Own Your Niche

06:00 – Strategy #2: Move Fast and Iterate Faster

08:30 – Strategy #3: Build a Brand People Want to Root For

10:00 – Emotional Branding Examples: Slack, Duolingo, Superhuman

12:00 – Strategy #4: Win on Customer Experience

13:30 – Recap of the Underdog Playbook

14:00 – Final Thoughts and Farewell Until After Summer

Links

• Interplay: Website, LinkedIn, Twitter
• Book: The Fundraising Rules
• MPD: LinkedIn, Twitter

Outsourcing isn't new — but the way startups can use it today has radically changed. On this week’s ep, I sat down with Shaun Walker, CEO of Spoke, to unpack what business process outsourcing (BPO) can look like for high-growth startups in 2025.

Let me say this upfront: most early - stage founders are missing out. Outsourcing isn’t just about slashing costs - it’s about building operational leverage and unlocking global talent pools in a way that accelerates your entire business.

Spoke’s model stands out because it focuses on fully embedded, dedicated teams that feel like extensions of your startup - they're engaged team members motivated to help you hit your milestones.

Whether it’s customer support, finance, data operations, or even engineering, there’s a strategic opportunity here. Especially in today’s hybrid and AI-enhanced world, Shaun argues that outsourcing can be a “bionic” function — letting you scale up or down with flexibility, access talent faster, and focus your internal team on what truly matters.

If you're a founder thinking about how to stretch your funding and build operational leverage, this is a must-listen. Hope it helps you navigate your own growth journey.

🕒 Chapter Markers

00:00 – Intro & Welcome

01:10 – What Spoke Does Differently in BPO

03:00 – Human-Centric Approach to Outsourcing

05:00 – Why Not Hire Offshore Directly?

07:00 – Building Embedded Global Teams

08:00 – Why Founders Miss BPO Opportunities

10:00 – When to Consider Outsourcing

12:00 – How Spoke Supports Startups

14:00 – The Cost vs. Strategic Advantage Debate

17:00 – Global Talent Quality and Motivation

19:00 – BPO as a Bionic Growth Function

21:00 – Helping Startups with U.S. Hiring Too

22:00 – High-Skill Roles & No Upper Limit

26:00 – AI’s Role in the Future of Outsourcing

28:00 – When Outsourcing Doesn’t Work

32:00 – Final Thoughts & Wrap-Up

• Shaun Walker: LinkedIn
• Spoke: Website
• Interplay: Website, LinkedIn, Twitter
• Book: The Fundraising Rules

How do you determine if your idea is truly worth pursuing? In this week’s episode, we dive into a practical framework that breaks down the evaluation process into four critical components: the pain point, the market size, the defensibility of your product, and how you plan to monetize and scale.

Whether you're just brainstorming or already building, these criteria will help you gut-check your concept and avoid wasting time on ideas that aren’t big - or painful - enough. We also discuss market sizing (TAM/SAM/SOM), moats, and why competitive advantage isn’t always what it seems. This is a must-listen for any founder looking to go from “cool idea” to real business.

Links:

• Interplay: Website, LinkedIn, Twitter
• Book: The Fundraising Rules
• MPD: LinkedIn, Twitter

Chapter Markers:

00:00 – Intro: Why Idea Validation Is So Hard

02:00 – The Real Question: Do You Have a Big Idea?

03:00 – The 4-Part Framework for Validating an Idea

03:45 – Step 1: Pain Point – Is This a Must-Have?

06:00 – Step 2: Market Size – TAM, SAM, SOM Explained

09:40 – Step 3: Product – Is It Defensible?

12:10 – Step 4: Monetization – Can It Scale?

15:10 – Final Thoughts: Gut-Check Your Idea

16:30 – Outro: Still Learning After Decades in the Game

Y Combinator has long been - and continues to be - the tip of the innovation spear. That's why I was especially excited to sit down with Garry Tan, President & CEO of Y Combinator, for a conversation that gets right to the core of what’s changing across the startup landscape.

At Interplay, I've spent years working alongside entrepreneurs who are laser-focused on building, scaling, and making a lasting impact. Over that time, I've seen countless trends come and go - but when a true seismic shift hits, like the one we’re seeing with AI today, it’s critical to step back and understand the bigger picture.

Garry and I dove deep into why vertical SaaS and AI-native startups are poised to drive the next wave of innovation, how lean, AI-augmented teams are rewriting the rules of company building, and why real traction still comes down to solving tangible user problems. We also explored the geographic shifts reshaping where startups thrive, the current realities of AI adoption, and what it truly takes to build a product the world actually wants. It’s a great, timely conversation.

A special thanks to Garry for joining me and sharing his insights.

00:00 – Introduction: Why Garry Tan and Y Combinator Matter

00:48 – Garry Tan Joins the Conversation

02:00 – Trends at the Top of the Startup Funnel

02:45 – The Rise of AI and Vertical SaaS Opportunities

04:00 – Leaner Startups: Building Companies with Smaller Teams

05:00 – How AI is Reshaping Company Growth and Scaling

06:00 – Internal Use of AI: Operational Efficiency Across Startups

07:30 – Early Innings: The Long-Term Impact of AI

09:00 – Mainstream AI Adoption: How Far We Have to Go

10:00 – Geography Trends: Where Startup Hubs Are Emerging

11:00 – Why San Francisco Still Matters for Founders

12:30 – The Golden Age of Startups: What's Next

13:30 – Critical Skills for Founders in the AI Era

14:00 – The #1 Reason Startups Fail: Solving Real User Problems

14:30 – Closing Thoughts: Building the Future of Innovation

Links:

• Garry Tan: LinkedIn
• Y Combinator: Website, LinkedIn
• Book: The Fundraising Rules
• Interplay: Website, LinkedIn, Twitter
• MPD: LinkedIn, Twitter

At Interplay, I've spent years working with entrepreneurs who are driven to build, scale, and make an impact - but too often, legal structuring gets overlooked in the frenzy of product development and fundraising. I've seen firsthand how costly early legal missteps can be so we brought on legal expert Eric Broad of Bowery Legal on to the pod to demystify early stage startup legal questions from entity type selection to the nuanced tax advantages like QSBS that most founders only hear about once it’s too late.

Our goal at Interplay is to equip founders with practical insights so they can focus on growing transformative businesses without getting tripped up by preventable legal issues. Whether you’re about to raise your first dollar or just brainstorming your MVP, this conversation will help you make smart, strategic choices. We cover the why behind Delaware's dominance, when to hit the "incorporate" button, and why trying to hack the system with clever workarounds rarely works in your favor.

I hope this deep dive helps founders avoid headaches and build with confidence.

Links:

• Eric Broad: LinkedIn
• Bowery Legal: Website, LinkedIn
• Phuong Ireland: LinkedIn
• Book: The Fundraising Rules
• Interplay: Website, LinkedIn, Twitter
• MPD: LinkedIn, Twitter

Chris Zhang, Partner and CIO of Ascend Interplay (Interplay’s multi-family office), returns to the pod to provide an in-depth analysis of China’s economic landscape in 2025, offering insights beyond mainstream media narratives. We discuss the current state of China’s economy, examining key indicators such as GDP growth, industrial production, and trade activity. At the same time, Chris highlights major concerns, including deflation, a struggling housing market, and long-term demographic challenges, while also shedding light on the country’s transition from a manufacturing-driven economy to a service-oriented one.

We then dive into the geopolitical dynamics between the U.S. and China. In addition to discussing the tariffs, we compare today’s economic competition to the Cold War era, and how shifting alliances - particularly in Europe and the Middle East - are reshaping global power structures.

We also cover China’s technological advancements, particularly in AI and EV manufacturing, where it continues to challenge U.S. dominance. Chris analyzes the impact of U.S. tariffs, supply chain shifts, and investment flows, emphasizing how China remains a key player in the global economy despite short-term volatility.

We wrap up with Chris’s firsthand insights from his recent trip to Beijing and Zhengzhou, where he observes China’s strong consumer activity despite ongoing real estate struggles. The episode concludes with a deep dive into China’s investment landscape, shifting geopolitical dynamics, and the nation’s long-term trajectory—offering critical perspectives on how it will continue to shape global trade and economic power structures.

Links:

• Book: The Fundraising Rules
• Interplay: Website, LinkedIn, Twitter
• MPD: LinkedIn, Twitter

Seed-stage valuation can feel like a black box. Unlike later-stage companies with clear financial metrics, early-stage startups are evaluated based on qualitative factors, market conditions, and investor demand. Founders with finance backgrounds often expect rigid valuation models, only to realize that early-stage investing is more art than science. However, strategic valuation methods and investor benchmarks offer a structured approach, helping founders navigate the process with confidence.

In today’s podcast, we break down the most common seed-stage valuation methods—including the Investor Target Ownership approach, the Berkus Method, and the increasingly popular SAFE note. We also highlight key founder pitfalls, such as over-inflating valuations or underpricing their startups, and explain how investor demand influences the equation.

Understanding these factors can help you navigate fundraising with clarity. The goal isn't just to get the highest valuation—it's to secure the right investment partners and ensure long-term success.

Links:

• Book: The Fundraising Rules
• Interplay: Website, LinkedIn, Twitter
• MPD: LinkedIn, Twitter

On this week’s episode I chat with Kass and Mike Lazerow, a powerhouse entrepreneurial duo known for building and exiting multiple companies, including Golf.com and Buddy Media (which was acquired by Salesforce for $745 million).

The conversation dives into their unique dynamic as a husband-and-wife co-founding team, their entrepreneurial journey spanning decades, and their latest venture—writing "Shoveling $h!t: A Love Story" a brutally honest book about the highs and lows of entrepreneurship.

We discuss what makes a strong co-founder relationship, the realities of scaling a business, and Kass and Mike’s ongoing mission to mentor and support founders. With thoughts on fundraising, company culture, and life after an exit, this episode offers a candid look at the realities of entrepreneurship—perfect for founders, investors, and anyone navigating the startup journey.

Links:

• Book: Shoveling $h!t: A Love Story
• Kass & Mike: Instagram, YouTube, X, Facebook, LinkedIn (Kass), LinkedIn (Mike)
• MPD: LinkedIn, X
• Interplay: Website, LinkedIn, Twitter

Navigating startup taxes can be challenging, but this comprehensive guide simplifies the process. Learn how to handle 1099 filings, leverage R&D tax credits for significant savings, and strategically use tax extensions to reduce stress. Discover practical tips for managing financial books, avoiding common tax pitfalls like Delaware franchise tax panic, and handling remote employee tax implications. Whether you're pre-revenue or scaling quickly, this article provides actionable insights to help startups stay compliant, optimize financial resources, and focus on growth.

Links:

• Book: The Fundraising Rules
• Interplay: LinkedIn, Twitter, Website
• MPD: LinkedIn, Twitter
• Kate Kelly: LinkedIn
• Chelsea Capital: LinkedIn, Website

The time of year for reflection is upon us, so in this week’s episode the team and I review our 2024 predictions and dive into bold forecasts for 2025. From the impact of geopolitical shifts to the state of venture capital and global deglobalization trends, we explore what lies ahead for technology, startups, and markets. We cover key trends like AI's application layer boom, the rise of humanoid robots in the workforce, the evolving IPO market, and much more.

What do you think is going to happen in 2025? Share in the comments below.

Links:

• Book: The Fundraising Rules
• Interplay: Website, LinkedIn, Twitter
• MPD: LinkedIn, Twitter