Inside Startup Funding

She Raised $4M to Fix What LinkedIn Broke | Caroline Dell, CEO of Goodword

In this episode of Inside the Round, host Helena Fogarty sits down with Caroline Dell, CEO and Co-founder of Goodword, to break down the real realities of raising their $4 Million Seed Round led by Human Ventures. Caroline shares her journey from working in consulting at Bain and as a strategic operator at Chief to the pivotal moment she realized she was ready to be a CEO.This conversation goes beyond pitch decks and valuations to explore: - Why relationships truly are everything. - How a conversation with Chief's CEO changed her career trajectory. - The critical difference between being an early employee and the ultimate decision-making CEO. - The challenge of "pattern matching" and convincing investors their product was not just another personal CRM "graveyard". - The strategic use of warm introductions and why "Pipeline Cures All" in fundraising. - The intentional strategy for finding and vetting her co-founder. - Why Goodword is a VC-backable business due to the massive market opportunity, drawing comparisons to LinkedIn. - The core advice for early-stage founders: don't skip the fundraising prep.A must-watch for founders navigating the complexities of seed-stage fundraising and transitioning into the CEO role.Timestamps:00:00 - Intro00:58 - Goodword's Introduction 01:39 - Caroline Dell's Career Background04:20 - The Decision to Become a CEO and Leadership Mindset.08:32 - The Genesis of Goodword 14:05 - Finding a Co-Founder18:15 - The Difference Between Being an Employee and a Founder/CEO23:38 - Knowing the Right Time to Found the Company25:56 - Determining Goodword's VC-Backability and Market Opportunity30:31 - The Role of AI in Strengthening Human Relationships and the Loneliness Epidemic.34:50 - The Fundraising Strategy47:00 - The Biggest Fundraising Challenges54:35 - What Convinced Investors to Commit Early58:15 - Post-Funding Activities: Product Launch, Hiring, and Early Validation.1:02:14 - Key Advice for Early-Stage Founders Raising Capital. - **04:09** | The Moment She Knew She Wanted to be a CEO - **08:12** | Why Goodword Was Started (Relationships are Everything) - **13:41** | Finding a Co-founder and "Co-founder Dating" - **17:51** | The Difference Between Being an Early Employee and a CEO - **25:31** | Why Goodword Is VC-Backable - **38:52** | Fundraising Strategy: Prioritizing Warm Introductions - **46:36** | The Biggest Challenges During the Fundraise (Pattern Matching) - **1:01:56** | Key Fundraising Advice for Early-Stage Founders

The Dark Truth About Fundraising No VC Tells You

In this episode of Inside the Round, Helena Fogarty sits down with James Zahn, Founder of Ranger AI, to break down the real realities of fundraising that most founders don’t talk about.James shares his journey from solving industrial tendering problems as an engineer to raising a $2.5M pre-seed round for Ranger AI, including lessons from angel investors, design partners, non-dilutive government funding, and working with institutional VCs.This conversation goes beyond pitch decks and valuations to explore:- Why fundraising often creates more responsibility, not relief- How strong relationships outperform aggressive VC outreach- The role of design partners in early-stage success- When raising capital actually makes sense — and when it doesn’t- How founders can stay mentally and operationally strong while scalingA must-watch for founders navigating seed and pre-seed fundraising in today’s market.Timestamps:00:00 Fundraising creates more problems, not solutions01:15 Why Ranger AI exists (founder backstory)06:54 Angels & investors = relationships, not money12:26 Rejection mindset that actually works20:10 EIR at 25 Madison (how Ranger really started)24:20 Raising $5M non-dilutive from the government31:13 Why raising $2.5M actually made sense37:01 How the round was raised (inbound, not cold VC spam)43:13 Valuation mistakes founders keep making52:43 Hot take: don’t maximize valuation57:40 Staying sane while building a company01:00:02 Final truth about fundraising

Raised $10M After VCs Ghosted: Circadian Risk’s Story

In this episode, Michael Martin shares the real story behind how Circadian Risk raised $10M after being ghosted by VCs.We break down:Why investors initially passed on the ideaHow the team built conviction before consensusWhat changed between rejection and a successful raiseLessons for founders building in misunderstood or emerging categoriesA candid conversation about fundraising, persistence, and building when belief comes late.Perfect for founders, operators, and investors who want the unfiltered reality behind a $10M raise.

Navigating the Emotional Toll of Startup Shutdowns - Jaclyn Siu of Starcycle

In this conversation, Jacyln Siu of Starcycle shares her journey from growing up in Hong Kong to becoming a successful entrepreneur in the U.S. She discusses the emotional challenges of shutting down startups, the importance of community and networking, and how these experiences shaped her new venture, Starcycle. The conversation emphasizes resilience, learning from failure, and the significance of building supportive relationships in the entrepreneurial journey.
 
00:00 From Hong Kong to Entrepreneurship02:54 The Journey of Learning and Adapting06:02 The Pain of Shutdowns and Lessons Learned08:50 The Birth of Star Cycle12:01 Navigating the Challenges of Starting Over14:48 Building a Supportive Network17:50 The Importance of Customer Development20:56 Pricing Strategies and Iteration24:04 Facing the Reality of Shutdowns27:01 The Role of Investors in a Founder’s Journey29:57 Building in Public and Community Support
 
Helena's LinkedIn: https://www.linkedin.com/in/helenafogarty Jaclyn's LinkedIn: https://www.linkedin.com/in/jaclynsiu/
 
🎬 Shot at 28th&Park in New York CityLearn more at: https://28thpark.com/📸 Follow us: https://www.instagram.com/28thpark/
 
Inside the Round is sponsored by Bamboo X, the leading technical and design recruiting partner to startups from Seed to IPO.   To learn more about Bamboo X: https://bamboo-x.com/

The Role of Legal Counsel in Startup Success: Inside the Process with Samir Bakhru

In this insightful episode of Inside the Process, Helena Fogarty, interviews Samir Bakhru from Orrick, Harrington, and Sutcliffe. They discuss the intricacies of raising capital, the importance of choosing the right legal counsel, and the evolving landscape of early-stage investing. Samir shares his journey into the startup ecosystem, emphasizing the significance of having tough conversations early and the role of legal advisors in a startup's success.
Helena's LinkedIn: https://www.linkedin.com/in/helenafogarty Samir's LinkedIn: https://www.linkedin.com/in/samirbakhru/
🎬 Shot at 28th&Park in New York CityLearn more at: https://28thpark.com/📸 Follow us: https://www.instagram.com/28thpark/
Inside the Process is sponsored by Bamboo X, the leading technical and design recruiting partner to startups from Seed to IPO.   To learn more about Bamboo X: https://bamboo-x.com/

Ella Moloney-Cook: From Founder to Investor Advocate

In this episode of Inside the Round, Helena Fogarty speaks with Ella Moloney-Cook, co-founder and COO of Upper Echelon, about her unique entrepreneurial journey from Australia to the US, the importance of strategic capital, and the role of mental health in entrepreneurship. Ella shares insights on building community, effective investor outreach strategies, and creating unique experiences for investors. She also discusses the challenges of navigating investor relationships and the surprising realizations she has had as a founder in the investor-backed space. In this conversation, the speaker discusses the significance of strategic capital in entrepreneurship, emphasizing the need for founders to align with investors who can provide more than just financial support. They share insights from their experience in the VCPE program at Columbia, offering advice for new founders on raising capital and building meaningful relationships within the startup ecosystem. The discussion also touches on the evolution of business models in response to changing market dynamics, the importance of mental well-being for founders, and the role of community in fostering success.00:00 The Importance of Strategic Capital02:15 Ella's Entrepreneurial Journey05:21 Mental Health and Community in Entrepreneurship08:02 Transitioning from Australia to the US12:01 Building Upper Echelon: The Business Model16:13 Effective Investor Outreach Strategies18:26 Creating Unique Investor Experiences23:38 Navigating Tough Conversations with Investors30:49 Surprises in the Investor-Backed Journey31:40 The Importance of Strategic Capital34:10 Navigating the Evolving Landscape of Technology35:43 Learning from the VCPE Program37:14 Advice for Founders Raising Capital43:39 Building Meaningful Relationships in Fundraising44:39 Evolving Business Models Post-Funding51:53 Controversial Insights on Fundraising54:44 Leveraging Founder AI Labs for Success57:39 Maintaining Well-Being as a FounderHelena's LinkedIn: https://www.linkedin.com/in/helenafogarty Ella's LinkedIn: https://www.linkedin.com/in/ellamolonycook/🎬 Shot at 28th&Park in New York CityLearn more at: https://28thpark.com/📸 Follow us: https://www.instagram.com/28thpark/Inside the Round is sponsored by Bamboo X, the leading technical and design recruiting partner to startups from Seed to IPO. To learn more about Bamboo X: https://bamboo-x.com/

Ella Maloney-Cook: From Founder to Investor Advocate

In this episode of Inside the Round, Helena Fogarty speaks with Ella Maloney-Cook, co-founder and COO of Upper Echelon, about her unique entrepreneurial journey from Australia to the US, the importance of strategic capital, and the role of mental health in entrepreneurship. Ella shares insights on building community, effective investor outreach strategies, and creating unique experiences for investors. She also discusses the challenges of navigating investor relationships and the surprising realizations she has had as a founder in the investor-backed space. In this conversation, the speaker discusses the significance of strategic capital in entrepreneurship, emphasizing the need for founders to align with investors who can provide more than just financial support. They share insights from their experience in the VCPE program at Columbia, offering advice for new founders on raising capital and building meaningful relationships within the startup ecosystem. The discussion also touches on the evolution of business models in response to changing market dynamics, the importance of mental well-being for founders, and the role of community in fostering success.
00:00 The Importance of Strategic Capital02:15 Ella's Entrepreneurial Journey05:21 Mental Health and Community in Entrepreneurship08:02 Transitioning from Australia to the US12:01 Building Upper Echelon: The Business Model16:13 Effective Investor Outreach Strategies18:26 Creating Unique Investor Experiences23:38 Navigating Tough Conversations with Investors30:49 Surprises in the Investor-Backed Journey31:40 The Importance of Strategic Capital34:10 Navigating the Evolving Landscape of Technology35:43 Learning from the VCPE Program37:14 Advice for Founders Raising Capital43:39 Building Meaningful Relationships in Fundraising44:39 Evolving Business Models Post-Funding51:53 Controversial Insights on Fundraising54:44 Leveraging Founder AI Labs for Success57:39 Maintaining Well-Being as a Founder
Helena's LinkedIn: https://www.linkedin.com/in/helenafogarty Ella's LinkedIn: https://www.linkedin.com/in/ellamolonycook/
🎬 Shot at 28th&Park in New York CityLearn more at: https://28thpark.com/📸 Follow us: https://www.instagram.com/28thpark/
Inside the Round is sponsored by Bamboo X, the leading technical and design recruiting partner to startups from Seed to IPO.   To learn more about Bamboo X: https://bamboo-x.com/

Empowering Women in Venture Capital - Inside The Fund with Kerry Rupp

Unlocking Capital: Insights from an Angel Investor with Katie Dunn

In this episode of Inside the Fund, host Helena Fogarty speaks with angel investor Katie Dunn about her journey into angel investing, her investment philosophy, and the importance of supporting underrepresented founders. They discuss the challenges of capital raising, the significance of building relationships, and the evolving landscape of startup funding. Katie shares insights on evaluating founders, navigating deal flow, and the role of AI in investor-founder interactions. The conversation also touches on the importance of diversity in investing and the value of building in public.
Helena's LinkedIn: https://www.linkedin.com/in/helenafogarty
Stefanie's LinkedIn: https://www.linkedin.com/in/stefaniefrancis/
🎬 Shot at 28th&Park in New York City
Learn more at: https://28thpark.com/
📸 Follow us: https://www.instagram.com/28thpark/
Inside the Round is sponsored by Bamboo X, the leading technical and design recruiting partner to startups from Seed to IPO.
To learn more about Bamboo X: https://bamboo-x.com/

Why Relationships Are the New Currency of Startup Growth with Stefanie Francis of Hootology

In this episode of Inside the Round, Helena Fogarty speaks with Stefanie Francis, co-founder of Hootology, about the challenges of market research, the journey of entrepreneurship, and the importance of honesty and relationships in fundraising. Stefanie shares her personal story, the evolution of Hootology, and the emotional landscape of being a founder. They discuss the need for a supportive community and the potential for changing the investment ecosystem to be more inclusive and collaborative. The conversation emphasizes the significance of self-discovery, mental health, and the power of asking for help in the entrepreneurial journey.
 
 
00:00 Introduction to Hootology and Market Research Challenges
02:51 Stephanie's Origin Story and the Birth of Hootology
05:57 The Journey of Self-Discovery and Entrepreneurship
08:51 Navigating the Role of a Founder
11:43 The Importance of Relationships in Fundraising
14:39 The Emotional Landscape of Founders
17:42 Rethinking the Investment Ecosystem
20:33 The Reality of Founding a Company
23:41 The Process of Raising Capital
26:47 The Power of Asking for Help
29:26 Building a Supportive Community
32:24 The Role of Honesty in Business
35:21 The Future of Hootology and Its Impact
38:22 Maintaining Well-Being as a Founder
41:18 The Importance of Team Dynamics
44:17 The Journey of Growth and Possibility
47:08 Creating Pathways for Others
50:11 Final Thoughts and Reflections
 
Helena's LinkedIn: https://www.linkedin.com/in/helenafogarty
Stefanie's LinkedIn: https://www.linkedin.com/in/stefaniefrancis/
 
🎬 Shot at 28th&Park in New York City
Learn more at: https://28thpark.com/
📸 Follow us: https://www.instagram.com/28thpark/
 
Inside the Round is sponsored by Bamboo X, the leading technical and design recruiting partner to startups from Seed to IPO.
 
To learn more about Bamboo X: https://bamboo-x.com/