Inside Startup Funding

Charlie O’Donnell, 20-year VC turned VC coach and author of Founder Unfriendly: What Investors Won’t Tell You About Getting Funded, joins Helena Fogarty on Inside the Fund to break down how venture capital decisions actually get made.

In this conversation, Charlie explains why most cold outreach fails, what makes an investor actually answer, and how founders should think about running a first pitch meeting like a sales conversat...

In this episode of Inside the Fund, we sit down with Zoe Jakubowich, a fractional Chief of Staff and a member of the investment team at VHS Ventures, to unpack a common misconception in consumer startups: venture capital isn’t the right path for most CPG brands.

Zoe explains why founders should only raise if they’re ready to scale, what it actually takes to build traction, and how to think about growth before bringing on institu...

Andrew Ackerman, 2x startup founder, venture capitalist, and author of The Entrepreneur’s Odyssey, joins us on Inside the Fund to talk about valuation, investor psychology, and what founders get wrong about fundraising process.

In this episode, Andrew explains why most founders have less leverage on valuation than they think, why competing term sheets matter so much, and why investor FOMO is often the only thing that speeds up a...

Fundraising isn’t about getting to a yes. It’s about how you handle all the no’s along the way.

Maria Intscher-Owrang, CEO of Simplifyber, joins us on Inside the Round to break down how founders should really think about fundraising, rejection, and long-term investor relationships. Simplifyber is building a new category of materials with bio-based, moldable fibers that can replace traditional textiles and some plastics, backed b...

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 is...

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 d...

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 tec...

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 invest...

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 i...

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 c...

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 slowdo...

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 va...

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...

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 conversatio...

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 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...

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 challe...

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 challe...