Startups Decoded

Casey Woo has spent over two decades inside the engine room of real companies, scaling startups as a 6x CFO and 2x COO across SaaS, marketplaces, hardware, eCommerce, and beyond.

After walking away from a successful career in public markets, Casey chose the harder path: joining early-stage startups, eating glass, and learning how companies actually get built under pressure. Along the way, he founded the Operators Guild, a global community of 1,200+ elite builders, and FOG Ventures, an operator-led investment platform backing the modern operator and GTM stack.

In this conversation, we unpack why generalist operators are becoming the new frontier for founders and investors. We talk about business as both physics and art, why judgment beats specialization early, what separates great operators from average ones, and why VCs increasingly back operator-led companies and platforms.

This is an operator-first conversation about craft, execution, and building companies that actually work, without startup theater.

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Chapters

• 00:02 Introduction to Operators and Generalists
• 01:13 Casey Wu’s Journey from Wall Street to Startups
• 03:22 The Cultural Shift: From Banking to Building
• 05:34 The Role of Operators in Startups
• 09:04 The Birth of the Operators Guild
• 12:24 Defining the Roles: Founder vs. Operator
• 15:31 The Evolution of the Operator Role
• 16:30 The Impact of Technology on Operators
• 22:34 Advice for Aspiring Operators
• 22:42 The Importance of Community in Business
• 24:23 Learning Through Experience
• 25:40 Fundamentals of Business Success
• 27:33 The Role of Human Relationships
• 28:45 The Operators Guild and Knowledge Sharing
• 34:31 Introducing Fog Ventures
• 40:44 Customer Feedback and Product Development

Guest Bio

Casey Woo is the Founder of the Operators Guild and General Partner at FOG Ventures, a leading operator-led investing platform.

A former public markets investor, Casey has spent over 20 years operating inside high-growth companies as a 6x CFO and 2x COO, guiding startups from early-stage through hypergrowth, multiple funding rounds, and pre-IPO. His experience spans software, hardware, marketplaces, eCommerce, supply chain, real estate, and professional communities.

Through the Operators Guild, Casey built a global network of more than 1,200 elite operators, the people responsible for scaling some of the fastest-growing companies in tech. Building on that foundation, he launched FOG Ventures, investing alongside operators in the modern operator and GTM software stack.

email: [email protected]

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Music Credit

“Neptuno” – Phondupe (Album: Onykia)

Mike Adams has spent 30 years doing what most founders underestimate and then desperately need. Connecting people. Lead generation

From HP to Apple to Zoom, and across 1,000+ events, Mike has built his career by understanding how trust, reputation, and introductions actually move deals forward. Now, as the founder of introstars, he’s turning referrals into the ultimate scalable lead-gen paradigm and opening up the intro economy to be measurable, trackable, and valuable.

In this conversation, we unpack why the best growth no longer comes from cold outreach, why super connectors think differently about value, and how founders can build real leverage by investing in relationships long before they need them. We talk about the “intro economy,” the ethics of monetising connections, what kind of intros make the biggest difference, and why focusing your time on sending referrals to others will actually help your own business.

This is a conversation for founders tired of shouting into the void and curious about building growth through trust instead of hacks.

Chapters

• 00:00 Introduction to Networking in the Age of AI
• 02:02 Mike’s Journey: From Sales to Super Connector
• 06:10 The Importance of Trust and Vulnerability
• 11:56 Givers vs. Takers in Networking
• 17:35 The Role of Introductions in Business Success
• 24:01 Building Your Personal Brand Through Connections
• 24:33 Building Trust and Reputation
• 29:26 The Shift from Cold Outreach to Warm Introductions
• 37:23 The Role of AI in Networking
• 44:33 introstars: Connecting People for Mutual Benefit
• 47:06 Closing Thoughts on Human Connection

Mike Adams

The founder of introstars, an investor in 20+ startups, and the host of The Super Connectors Podcast. With over three decades in sales and marketing at companies including HP, Apple, and Zoom, Mike has built a reputation as a high-trust connector who understands how relationships really drive business.

Through introstars, Mike is building the first platform designed to reward introducers for successful outcomes, turning introductions into a measurable and sustainable growth channel. He’s passionate about helping founders, operators, and investors unlock value through genuine connection rather than transactional networking.

Who Should Listen

• Founders building partnerships and distribution
• Operators responsible for growth and BD
• Investors who rely on trusted deal flow
• Anyone who believes relationships still matter in an AI-first world

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Music Credit

“Neptuno” – Phondupe (Album: Onykia) 

Mike Ma doesn’t invest in decks. He invests in people.

As Managing Partner and Head Coach at Sidecut Ventures, Mike works with what he calls “coachable superheroes”, early-stage, mission-driven founders tackling real problems in economic mobility, healthcare, climate, and education.

In this conversation, we unpack what it actually means to be coachable as a founder, why most advice fails in practice, and how real progress happens when coaching, capital, and execution collide. Mike shares lessons from the trenches — blending Fortune 500 experience with venture-backed CXO roles, and explains why the best founders don’t just seek answers, they build judgement.

We also explore Sidecut’s hands-on approach to venture building, the parallels between adaptive sports coaching and startup leadership, and why helping founders unlock potential often means meeting them exactly where they are, not where the pitch says they should be.

This episode is for founders who want fewer platitudes, better questions, and support that actually shows up.

Chapters

• 00:00 Introduction to Impact Investing
• 02:42 The Thesis of Sidecut Ventures
• 04:59 Understanding Impact and Returns
• 07:49 The Case for Climate Investments
• 10:41 The Duality of Capitalism
• 13:06 The Role of Ethics in Business
• 15:47 The Importance of Mission-Driven Founders
• 18:33 Evaluating Founders Beyond the Surface
• 23:54 The Foxhole: Partnering with Founders
• 27:19 The Impact of Investment Models
• 32:01 The Reality of Foundership
• 36:50 Understanding the Founder’s Journey
• 39:43 Evaluating Impact and Market Risks

Mike Ma 

Managing Partner and Head Coach at Sidecut Ventures, where he invests in and coaches early-stage, mission-driven founders working on some of society’s hardest problems.

He brings a rare blend of Fortune 500 experience (Bank of America, Vanguard) and venture-backed CXO leadership(including Betterment and Own Up), rolling up his sleeves across product, strategy, and fundraising. Mike believes the best venture outcomes are built through proximity, trust, and real coaching, not performative advice.

Sidecut Ventures:
Pitch: https://www.sidecut.vc/pitch-us
LinkedIn: https://www.linkedin.com/in/michaelwma/

Presented by Morrison Foerster - mofo.com

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Music Credit

“Neptuno” – Phondupe (Album: Onykia) 

Startups Decoded - Presented by Morrison Foerster - mofo.com.

Luke Tobin has built seven businesses across hospitality, e-commerce, and agencies. Three exits. One of them: an eight-figure agency sale that started with £100, no funding, and a healthy dose of imposter syndrome.

Today, Luke sits at the messy intersection of founders, capital, and exits, backing businesses, fixing broken agency models, and coaching operators to turn self-doubt into fuel instead of friction.

In this episode, we get brutally practical on what actually drives profitable growth, why most agencies never become exit-ready, how to price for margin (not ego), and why thinking like a buyer early changes everything. This is an operator conversation, not “founder vibes”. If you want a business that works without you sweating through every Monday, press play.

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Chapters

• 00:00 Introduction to Entrepreneurship and Exits
• 10:31 The Journey of Building and Selling Businesses
• 19:14 Structuring for Success: Frameworks and Control
• 22:02 Uncovering Unique Value in Startups
• 23:27 Prioritizing Impactful Outcomes
• 25:39 Balancing Human Intelligence and AI
• 27:25 Effective Automation Strategies
• 29:06 Navigating Growth Stages in Business
• 31:56 The Importance of Agility in Startups
• 34:09 Cultural Dynamics in Team Growth
• 37:32 Hiring Smart: The Founder’s Dilemma
• 39:31 Investment Insights and Founder Evaluation

Luke Tobin

Luke Tobin is a founder, investor, and operator with three exits and seven businesses built across hospitality, e-commerce, and agencies. He scaled his most recent agency from £100 to an eight-figure exit in five years with no external funding.

Today, he’s the founder of Unusual Group, owner of Tobin Capital, partner at A-Frame Venture Studio, and author of The Success Method newsletter read by 100,000+ founders weekly. Luke advises founders on pricing, operations, hiring, and exits with a relentless focus on building businesses that actually work.

Who Should Listen

• Agency owners who want better margins (and a real exit path)
• Founders dealing with imposter syndrome while scaling
• Operators building without funding and without delusion
• Investors who care about operator-led growth
• Anyone who wants the real playbook behind profitable businesses

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Music Credit

“Neptuno” – Phondupe (Album: Onykia)

Niluka Kavanagh left Big 4 consulting with a simple question: Can I work for myself, and can I do it from anywhere?

That question turned into an experiment, then a business, then ImagineThat, a global club for first-time founders who are trying to build something without losing themselves in the process.

We talk about the unsexy realities people don’t plan for: uncertainty, isolation, confidence dips, and the weird moment where you realise “being your own boss” can still mean being owned by customers. Niluka shares the framework she uses with founders to go from “I’ve got skills” to “I’ve got a business,” why you should design your life before you design your model, and why your personal brand is the only asset that survives pivots.

This is a conversation for anyone in corporate with a pull toward independence, and anyone early-stage who wants fewer vibes and more clarity.

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Chapters

• 00:00 The Journey of Transitioning from Corporate to Entrepreneurship
• 03:08 Finding Purpose and Vision in Business
• 05:53 Understanding the Risks and Rewards of Entrepreneurship
• 08:44 Building a Support Network for Founders
• 11:35 The Importance of Market Validation
• 14:25 Creating a Founder Brand and Authentic Storytelling
• 22:27 Building Your Founder Brand
• 25:41 The Importance of Values in Branding
• 29:47 The Power of Storytelling in Personal Branding
• 34:07 Recognizing Your Achievements as a Founder
• 38:31 The Role of Community in Entrepreneurship
• 43:20 Creating a Supportive Environment for Founders

Niluka Kavanagh 

A founder, executive coach, keynote speaker, and creator focused on the future of work.

She is the Founder of ImagineThat, the global club for new founders, and the creator of The Modern CEO, a leadership program helping companies evolve into next-generation workplaces.

Previously, she worked as a consultant at KPMG with clients like Mastercard, Tesco, and London Stock Exchange, co-founded KPMG FutureThinkers, and led communications for KPMG SheCan.

Niluka has spoken at leading universities, including Oxford, Trinity College Dublin, and Edinburgh University, and her work has been featured in The World Financial Review and Cambridge University Press.

Who Should Listen

• New founders transitioning out of corporate roles
• Executives leading younger or hybrid teams
• Operators building modern leadership cultures
• Anyone curious about how careers, ambition, and identity are reshaping entrepreneurship

Music Credit

“Neptuno” – Phondupe (Album: Onykia)

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Women, BIPOC, and LGBTQIA+ founders still get boxed out of capital, but Katie Dunn has built her angel investing thesis to do the opposite, and she’s doing it with actual reps (29 investments) and serious financial scar tissue (25+ years in banking with $10B financed).

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In this episode, Katie breaks down what early-stage angels really look for when they say they’re “betting on the founder”, why most cold outreach fails (hint: nobody reads the investor’s thesis), and how underrepresented founders can cut through the noise with clarity, credibility, and a simple story that lands.

We also get into the underrated part: investor relationships. Katie explains why your first investors should be your easiest next-round capital, why founders go dark when things get hard (and how that backfires), and how angels often deliver more value than VCs because they actually have time, context, and intent to help.

If you’re raising pre-seed/seed, building community, or trying to stop fundraising from eating your soul, this one’s a practical reset.

Chapters

• 00:00 Introduction to Angel Investing
• 04:18 Katie’s Journey in Finance
• 06:55 The Importance of Diversity in Funding
• 10:04 The Role of Immigrants in Startups
• 12:43 Building Community and Networks
• 15:30 The Value of Collaboration
• 18:23 The Role of Angels vs. VCs
• 21:07 The Importance of Communication
• 23:45 Finding the Right Investors
• 26:45 Using Technology to Connect
• 29:32 Assessing Founders and Their Pitches
• 32:20 The Art of the Pitch Deck
• 35:01 Final Thoughts and Resources

Katie Dunn

An experienced angel investor, board director, and startup advisor investing in underrepresented U.S. founders at the pre-seed and seed stages, primarily in CPG and technology. Through Masthead Strategies, she’s helped founders raise over $30M by combining investor psychology, storytelling, and AI-powered tools.

Her portfolio includes Outcast Brands (Blood Monkey Gin, Two Shores Rum), Another Tomorrow, Juliet Wine, WTHN, Forecastr, and Goodword. Katie also serves on the boards of Outcast Brands and the Enthuse Foundation, and advises Fierce Foundry, a femtech venture studio.

Who Should Listen

• Founders preparing to raise pre-seed or seed capital
• Underrepresented founders seeking tactical fundraising advice
• Angels or new investors looking to sharpen their evaluation process
• Anyone who wants to understand how trust, clarity, and communication drive funding decisions

Music Credit

“Neptuno” – Phondupe (Album: Onykia)

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Startup investing used to be gated, exclusive networks, complex diligence, and full-time fund managers. But what if anyone could build a startup portfolio the same way they’d shop online?

In this episode, Cheryl Kellond, serial founder and CEO of Play Money, shares how her platform is democratizing early-stage investing by pairing curated deals from new fund managers with an experience that feels more like shopping than finance. 

We dive into her journey from launching Bia Sport and Apostrophe (acquired by Centivo) to building Play Money, the new “fantasy league” for startup investing.

Expect a candid lesson on why making startup capital more inclusive can reshape who gets funded and who gets to build wealth.

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Chapters

• 00:00 Introduction to Play Money and Its Mission
• 04:37 The Challenges of Accessing Capital
• 11:21 The Evolution of Early Stage Investing
• 16:59 Understanding the Angel Investment Landscape
• 22:30 The Role of Education in Angel Investing
• 28:20 The Founder Experience on Play Money
• 33:49 Building Trust and Validation in Startups
• 39:27 The Future Vision for Play Money

Cheryl Kellond

Founder & CEO of Play Money, is a concept-to-launch expert who has driven $750M+ in revenue from healthtech, SaaS, hardware, and media products. She previously founded Apostrophe (Techstars ’17, acquired by Centivo) and Bia Sport (Lemnos ’12), and has launched major products at Adobe, Yahoo, and E*TRADE. Voted Denver’s Most Admired CEO and a 40 Over 40 honoree, she’s passionate about disrupting legacy industries and building founder-friendly ecosystems.

Who Should Listen

• Aspiring angel investors who want a smarter, accessible entry point
• Founders curious about new funding pathways
• Emerging fund managers building their first LP base
• Anyone interested in wealth-building through startups without “full-time VC” complexity

Music Credit

• “Neptuno” – Phondupe (Album: Onykia)

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As AI moves from clever tool to “virtual teammate,” nowhere is the shift more real than in finance.

In this episode of Startups Decoded, Invoice Butler founder & CEO Mihir Deo joins Andy Walsh to explore what happens when AI agents start doing the unglamorous work humans have always done—chasing invoices, managing cash flow, and acting like your accounts team.

We unpack how Invoice Butler is quietly replacing manual accounts receivable workflows with an AI-powered, human-backed agent, what that means for trust, brand, and relationships, and why the future of finance teams is smaller, sharper, and heavily automated, not human-free.

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Chapters

• 00:00 Introduction to AI and Trust
• 06:48 The Impact of AI on Business Dynamics
• 10:58 The Birth of Invoice Butler
• 16:51 How Invoice Butler Works
• 22:54 The Future of Automation and Human Touch
• 37:44 Target Customers and Vision for Invoice Butler

Mihir Deo:
Founder & CEO of Invoice Butler. With a background in software and product development, Mihir is focused on building AI tools that solve real problems, blending automation with human-first design.

Invoice Butler:

Invoice Butler blends AI efficiency with human oversight to deliver automated financial processes businesses can actually trust — reducing admin, improving cash flow, and giving founders more time to focus on growth.

Music Credit: “Neptuno” - Phondupe (Album: Onykia)

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Startups Decoded is a reader-supported publication. To receive new posts and support my work, consider becoming a free or paid subscriber on Substack.

In this episode, Andy Walsh sits down with Jennifer Lewis, former Founder CEO of queer social app Lex, to unpack the full arc from first fundraise to exit.

Jennifer shares what really happens behind the scenes when you’re raising as a queer female founder, how she navigated a co-founder departure mid-fundraise, and why “perfect data rooms” don’t close rounds, relationships, and conviction do.

They walk through how she scaled Lex into a beloved LGBTQ+ community, decided to sell to 9count, and protected the mission and culture through the acquisition.

If you’re a founder wrestling with fundraising, leadership, or whether to sell, this is a candid, hard-won playbook from someone who’s actually done it.

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Jennifer Lewis
Jennifer is an expert in launching and scaling startups from Seed to Series B. With global experience across Nike, Universal Music, Unilever, and Pepsi, she brings a bold, creative mindset to growth. She’s known for her work in women’s health, LGBTQ+ tech, and community-driven brands, and has led Lex through a major rebrand and exit. Jennifer has won 3 marketing effectiveness awards and over 40 creative awards.

Chapters

• 00:00 Introduction to the Journey of a Founder
• 01:28 From Advertising to Startups: Jennifer’s Background
• 04:47 Building Lex: A Personal Mission
• 09:57 The Importance of Fast Decision-Making
• 17:19 Navigating Co-Founder Dynamics and Fundraising
• 21:53 Navigating Leadership and Team Dynamics
• 25:34 Lessons from Fundraising Challenges
• 29:12 The Reality of Fundraising for Female Founders
• 33:16 The Importance of Culture in Acquisitions
• 36:41 Reflections on the Acquisition Decision
• 39:59 Exploring New Ventures and Personal Growth

About Lex
Lex is a social app for LGBTQ+ connection, inspired by vintage personal ads. Originally launched in 2019, it grew into a vibrant digital community for queer expression, with over 1 million downloads and millions of messages sent monthly. In 2024, Lex was acquired by 9count, home to other social platforms like Wink and Summer.

Music Credit:

“Neptuno” - Phondupe (Album: Onykia)

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Robert Harary found his first venture deal while in high school detention, and hasn’t looked back since. 

Today, he sits at the center of the venture ecosystem as both an investor and founder, with a decade-plus obsession for making access to capital more transparent, efficient, and equitable.

Robert is the #2 at Evolution VC Partners, where he’s been part of 300+ Culture Tech investments. He runs Timeless Ventures as GP, and has investments in companies like Colossal, Figure AI, and Sindarin. On the founder side, he co-founded DECKO (helping 300+ startups and funds raise $1.2B+) and Raisi (bringing founders in front of 2,000+ investors monthly).

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In this conversation, we break down:

• Why access to capital, not ideas, is the biggest bottleneck for founders
• How Robert evaluates moonshots (and why he backed OpenAI early)
• Lessons learned from co-founding DECKO and Weraise
• Where the venture ecosystem is failing—and what needs to change
• His belief that democratizing capital will unlock the next wave of transformative companies

Chapters

• 00:00 The Utopian World of Fundraising
• 06:40 The Evolution of Pitch Decks
• 13:16 Crafting the Perfect Pitch Deck
• 20:12 Understanding Investor Psychology
• 21:59 Cold Outreach and Investor Engagement
• 23:50 The Three Pillars of Startup Success
• 26:08 Effective Cold Email Strategies
• 28:29 The Art of Storytelling in Fundraising
• 32:40 Investor Marketing as a Relationship Game
• 39:14 Building Long-Term Investor Relationships

Guest Bio

Robert Harary is an investor, founder, and venture capitalist obsessed with making capital access more equitable. He is a GP at Timeless Ventures, #2 at Evolution VC Partners (300+ Culture Tech investments), and an angel investor in moonshots, including OpenAI and Colossal. He has co-founded DECKO and Weraise, platforms that have helped 300+ startups and funds raise $1.2B+ from Sequoia, a16z, Accel, YC, and others.

Who Should Listen

• Founders frustrated by investor access or gatekeeping
• Investors curious about democratized deal flow
• Operators interested in the “deck science” behind successful fundraising
• Anyone tracking moonshot bets reshaping the future

Music Credit

“Neptuno” – Phondupe (Album: Onykia)

Access All Areas.

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Web: startupsdecoded.com