How much of a startup’s outcome is shaped before anything goes wrong?

In this episode, Yashreeka Huq, Partner at Perkins Coie, shares a behind-the-scenes look at the legal side of venture. From board control and investor rights to how lawyers influence founder decisions, this conversation breaks down the mechanics that quietly shape company trajectories.

One key takeaway: “Believe the no, not the reason.” Investor feedback isn’t always the full story, and how founders interpret it can change everything.

Follow Inside Startup Funding for more conversations with builders and investors shaping the next decade.

Maddi Holman, General Partner at Daring Ventures, joins Inside Startup Funding to break down what actually matters for founders building today.

In this conversation, Maddi shares how the landscape has shifted from building being the hard part to winning being the hard part. We get into why distribution, trust, and timing now matter more than ever, how founders consistently misjudge customer behavior, and why many products fail despite solving real problems. She also walks through what she looks for when evaluating companies and the patterns she sees in the founders that outperform.

We also dive into real-world examples of founders building the wrong thing, the importance of staying close to customers, and what actually creates defensibility in a world where anything can be built quickly. Maddi brings a clear, operator-informed perspective on what separates companies that gain traction from those that don’t.

Topics we cover:

• Why building is no longer the hard part

• Distribution, trust, and timing as modern moats

• What founders get wrong about customer behavior

• Why great products still fail to gain adoption

• What actually creates defensibility today

• How top founders stay close to their customers

What actually makes a startup defensible now that it’s easier than ever to build?

In this episode of Inside the Fund, Helena Fogarty sits down with Jess Schram, Partner and Director of Investments and Incubations at Remedy Product Studio, to talk about how founders should think about fundraising, valuation, diligence, and what separates the best companies from the rest. Jess explains why selling and distribution matter more than technical superiority, how Remedy’s hybrid investment model works, and why some formidable businesses still struggle to raise in today’s market.

She also shares a striking story about discovering a founder was cooking the books while lead investors believed the company was thriving, plus her broader take on founder psychology, investor blind spots, and the signs she looks for when evaluating risk. One of the clearest takeaways: if you can’t sell what you’re building, good luck.

Follow Inside Startup Funding for more conversations with builders and investors shaping the future.

Andrea Hippeau, Partner at Lerer Hippeau, joins Inside the Fund to discuss how early-stage investors actually evaluate founders.

Andrea breaks down what she looks for before traction exists, why conviction often forms long before a formal pitch, and how long-term relationships between founders and investors shape many of the best investments. She also explains why trying to “fix” founders rarely works, and how experienced investors recognize important founder signals earlier than most people expect.

We also discuss how consumer investing works inside a venture firm, how investors separate real traction from short-term hype, and what has changed about early-stage fundraising over the past few years.

Topics include founder evaluation, venture conviction, early consumer investing, and how investors identify the next generation of founders.

Oren Michels, CEO of Barndoor AI, joins us on Inside the Round to break down how Barndoor raised $13.6M pre-product, why enterprise security can’t ship a janky v1, and how “fast fundraising” is usually the payout for years of relationship-building.

Oren shares what changed from Mashery (where the iPhone era pulled them into enterprise) to Barndoor AI (where day-one customers are household name companies). He also walks through investor qualification when there was no demo and no code, why fund size and check appetite matter, and why filling the second half of the round can be harder than finding the lead.

Topics we cover:

• Raising $13.6M pre-product

• Story arc pitching and fundraising as theater

• Investor targeting by fund size, check size, and partner dynamics

• Why enterprise security can’t ship a janky first version

• AI guardrails, oversight, and what it takes for agents to do real work

  
  

  Links:YouTube https://www.youtube.com/@InsideStartupFundingSubstack https://insidestartupfunding.substack.com/Apple Podcasts https://podcasts.apple.com/us/podcast/inside-startup-funding/id1840446437

  
  

  Sponsors:Aster AI https://www.asterhq.com/28th&Park https://28thpark.com/

Don’t follow capital. Let capital follow.

In this episode of Inside the Round, Nima Roohi of Blooming Health shares the fundraising hot take he wishes more founders lived by, plus the real mechanics of how he pushed through roughly 100 investor passes and kept the company moving anyway.

Nima unpacks:
• Why founders should be less malleable to investor feedback
• How he iterated his pitch after every meeting without losing conviction
• Why Blooming Health’s biggest early risk was market risk, not product risk
• The “default alive” mindset and scenario planning for different funding outcomes
• How building relationships over time set up a 26.5 million Series A led by Insight Partners

He also breaks down what Blooming Health is building in social care tech, why fragmentation and missing data keep budgets from compounding, and how Covid created the moment to prove multilingual automated outreach through community based organizations and government partners.

If you’re fundraising in a market investors don’t understand yet, this episode is a playbook for staying steady, staying lean, and staying in motion.

Subscribe for full episodes and future conversations.

About Inside Startup Funding:Inside Startup Funding is a multi format podcast and community hosted by fundraising expert Helena Fogarty, designed to demystify how startup capital really moves from first check to scale.
Our sub series include Inside the Fund, Inside the Round, and Inside the Process, each exploring a different side of the funding journey.

Sponsored by Aster AI, re imagining the operating system for recruiting, building infrastructure that connects the world’s top Product, Engineering, and Design talent with opportunities in the age of intelligent agents.

Filmed at 28th&Park in New York City.
Follow us on YouTube, LinkedIn, and Substack to stay close to how capital actually moves.

What does a valuation actually mean once you take venture math seriously?

In this episode of Inside the Fund, Justin Kang of Visible Hands breaks down the mechanics most founders never fully internalize. A valuation is not a payout. It is a projection inside a fund model governed by liquidity cycles, LP expectations, and fiduciary duty.

Justin unpacks:
• Why LP capital is locked up for years
• How IPO and M and A slowdowns reshape venture behavior
• Why VCs are almost always fundraising
• What fiduciary duty actually means in practice
• How portfolio math drives decisions more than narrative

He explains how capital constraints ripple through the ecosystem and why founders need to understand the fund structure behind the term sheet. When liquidity slows, timelines stretch. When exits stall, capital tightens. And when capital tightens, investor behavior changes.

If you are raising right now, this context matters.

Subscribe for full episodes and future conversations.

About Inside Startup Funding:
Inside Startup Funding is a multi format podcast and community hosted by fundraising expert Helena Fogarty, designed to demystify how startup capital really moves from first check to scale.
Our sub series include Inside the Fund, Inside the Round, and Inside the Process, each exploring a different side of the funding journey.

Sponsored by Bamboo X, a recruiting partner to startups building technical and design teams.

Filmed at 28th&Park in New York City.
Follow us on YouTube, LinkedIn, and Substack to stay close to how capital actually moves.

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 - Intro

00:58 - Goodword's Introduction

01:39 - Caroline Dell's Career Background

04:20 - The Decision to Become a CEO and Leadership Mindset.

08:32 - The Genesis of Goodword

14:05 - Finding a Co-Founder

18:15 - The Difference Between Being an Employee and a Founder/CEO

23:38 - Knowing the Right Time to Found the Company

25:56 - Determining Goodword's VC-Backability and Market Opportunity

30:31 - The Role of AI in Strengthening Human Relationships and the Loneliness Epidemic.

34:50 - The Fundraising Strategy

47:00 - The Biggest Fundraising Challenges

54:35 - What Convinced Investors to Commit Early

58:15 - 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

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 scaling

A must-watch for founders navigating seed and pre-seed fundraising in today’s market.

Timestamps:

00:00 Fundraising creates more problems, not solutions

01:15 Why Ranger AI exists (founder backstory)

06:54 Angels & investors = relationships, not money

12:26 Rejection mindset that actually works

20:10 EIR at 25 Madison (how Ranger really started)

24:20 Raising $5M non-dilutive from the government

31:13 Why raising $2.5M actually made sense

37:01 How the round was raised (inbound, not cold VC spam)

43:13 Valuation mistakes founders keep making

52:43 Hot take: don’t maximize valuation

57:40 Staying sane while building a company

01:00:02 Final truth about fundraising

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 idea

How the team built conviction before consensus

What changed between rejection and a successful raise

Lessons for founders building in misunderstood or emerging categories

A 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.