Inside Startup Funding

If you've ever walked out of an investor meeting that felt great and then never heard back, this one is for you.

Naseem Sayani has been on both sides of the table — Booz, BCG, a product studio that became a venture incubator, then Emmeline Ventures in 2021 and a hand in launching four funds since. Today she runs the Innovator Circle at WHAM, coordinating the early-stage women's health ecosystem, and hosts The Capital Flex. She walks through the three things she looks for in a founder, how she filters the pitches flooding her inbox, and the signals that tell you an investor is genuinely interested rather than politely curious. She also makes a case that the current system isn't going to be reformed — it needs to be rebuilt, and quickly, before late-stage AI deals starve the early ecosystem of a next generation entirely.

The line that reframes the whole conversation: "I'm not writing you a check because it happened to you. I'm writing you a check because the market is big and you were the best possible founder to get after it."

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

For our first-ever live taping of Inside Startup Funding: Unfiltered, I sat down in front of a room of founders with two people who see the funding market from opposite sides of the table — and got the version of the AI story that doesn't make it online. Not the headlines. The version happening inside pitch meetings, term sheet negotiations, and board decisions right now. If you are planning a seed or Series A in the next eighteen months, this conversation will change what you think a fundable company looks like.Jake Yormak and Samir Bakhru lay out why the bar has moved so far, so fast: roughly 40% of last year's venture dollars went into eight companies, only about 25 funds in the country can write a Series A check at today's sizes, and those funds are already committed. We get into the most dangerous assumption a founder can hold in 2026 — that zero to $1.5M ARR in eighteen months still earns a Series A — and what actually gets funded instead: enormous TAM, brutal speed, and a technical team that AI tools multiply rather than merely assist. We cover why moats have temporarily stopped mattering to investors, why companies are raising Series Bs six weeks after closing an A, why anti-poaching provisions are suddenly showing up in early-stage term sheets, and the honest conversation both of them now have to have in boardrooms with founders doing top-quartile work that would have been funded three years ago. We also spend real time on the part nobody posts about: how to recognize a slow bleed, when selling is the right answer, and why Jake pushes for a founder-and-employee carve-out even when his own fund takes the loss.Host — Helena Fogarty LinkedIn: https://www.linkedin.com/in/helenafogarty/Guest — Jake Yormak, Story Ventures LinkedIn: https://www.linkedin.com/in/jake-yormak-b8232756/Guest — Samir Bakhru, Orrick LinkedIn: https://www.linkedin.com/in/samirbakhru/SPONSORSOrrick — https://www.orrick.com/Aster AI — https://www.asterhq.com/

What does an early-stage investor actually need to see before writing a check?

Mike Chan, Managing Partner at Deep Ventures, joins Helena Fogarty to break down how he evaluates startups at the earliest stages, including companies that are still pre-product and pre-revenue. Mike explains why founders still need to show proof of demand, how he evaluates founder-market fit and distribution, and why saying you'll start executing once the funding arrives is a major red flag.

They also unpack how Deep Ventures operates across both a fund and a 1,300-member syndicate, what Mike learned investing through crypto bear markets, why technical founders often underestimate go-to-market, and how he thinks AI and crypto will increasingly intersect.

Plus, Mike shares what he learned from being a founder himself, why founders shouldn't obsess over competitors, what he wants founders to ask prospective investors, and why the strongest fundraising position is one where you aren't desperate to raise.

The takeaway: build the proof points first, create optionality, and raise from a position of strength.

Follow Inside Startup Funding for more conversations with the founders and early-stage investors shaping how startups get funded.

Jenny Duan, CEO & Co-Founder of Clair Health, and Abhinav Agarwal, CTO & Co-Founder, join Inside the Round to break down how they went from meeting at Stanford to building a hormone-aware wearable and raising $11.6 million in total funding.

Clair Health is developing a wrist-worn device designed to track estrogen, progesterone, LH, and FSH. Jenny and Abhinav explain why they saw a gap in existing women's health technology, how advances in sensors and machine learning made their approach possible, and why privacy and FDA clearance are central to the product they're building.

Then we get into the fundraising story. They discuss raising their first angel capital shortly after an early technical breakthrough, going through A16Z Speedrun, closing their seed round, and finding investors who believed in the larger opportunity in women's health.

Jenny also shares why she didn't understand the phrase "fundraising is a full-time job" until she went through it herself, how relationship-driven the process became, and what it felt like to repeatedly hear women's health described as "niche." She and Abhinav explain how they evaluated investors, divided responsibilities during the raise, and decided who they wanted on their cap table.

Topics we cover:

• Starting Clair Health at Stanford
• Building a new approach to hormone monitoring
• Privacy and sensitive health data
• Pursuing FDA clearance
• Raising the first angel round
• A16Z Speedrun and preparing for the seed raise
• Why fundraising became a full-time job
• Investor perceptions of women's health
• Being underestimated as a young founder
• Choosing the right investors
• What the new capital unlocks
• Advice for founders raising pre-seed

Follow Inside Startup Funding for more conversations with founders and investors about how startup rounds actually get done.

Having a great company and knowing how to raise money are two different skills.

Lucia Mari Sanguino, co-founder and CEO of AIVA TECH, joins Inside Startup Funding to break down the strategy behind her $1.5 million pre-seed raise. Lucia shares how she and her co-founder condensed investor meetings to create urgency, built warm introductions through other founders, refined their pitch from investor objections, and divided responsibilities so fundraising did not stop the company from building.

She also explains the mid-raise strategy change that transformed how she showed up with investors. Lucia became less accommodating and more direct, created fundraising alter egos with her co-founder, and even prompted Claude to rewrite her emails like a “rich white man.”

Her takeaway: “You might be a great player, but if you don’t know the rules and you don’t know the strategies, you will not win the game.”

We also get into how Lucia’s experience growing up in Ibiza and working as a hotel GM led to AIVA TECH, the emotional reality of finally closing the round, and why founders should start building relationships long before they need investor introductions.

SPONSORS:

Aster AI: Aster AI is re-imagining the operating system for recruiting, connecting top Product, Engineering, and Design talent with opportunities through an AI-native recruiting platform.
https://www.asterhq.com/

28th&Park: 28th&Park is a New York-based content and production studio that partners with founders, VCs, artists, and creators to produce podcasts, livestreams, events, and studio salons.
https://28thpark.com/

Laura McDonald and Dr. Christy Lane are the co-founders of Flora Fertility, the first individually owned fertility insurance platform.

After raising a pre-seed round in 2024, Flora recently closed a $5M seed round led by Manchester Story Group. In this episode of Inside the Round, Laura and Christy break down what it took to raise capital while building an entirely new category of insurance.

They share why relationships and warm introductions became central to their fundraising strategy, how accelerator programs and industry events helped open doors, and why founders shouldn't underestimate the value of simply getting in the room.

They also discuss how being second-time founders changed the way they approached investors, how they decided who they actually wanted on their cap table, and one of the most important fundraising lessons they learned: when a VC doesn't get it, know when to move on.

Inside the Round, hosted by Helena Fogarty , part of Inside Startup Funding.

Sponsored by:

Aster AI
Aster AI is 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. Through an end-to-end AI-native platform they build teams at AI speed with recruiter finesse.

28th&Park
Filmed at 28th&Park in New York City.

Mark Volchek, Founding Partner at Las Olas Venture Capital, joins Inside the Fund to talk about the full founder-to-investor journey.

Before becoming an investor, Mark co-founded Higher One as a college senior and helped grow the company from three founders in a dorm room to profitability, more than $250M in revenue, 1,000+ employees, and an IPO. But before that outcome, there were moments when the company had less than two weeks of cash in the bank and could barely make one more payroll.

In this episode, Mark breaks down raising through the dot-com crash, what going public actually feels like, why an IPO is not always the exit founders imagine, and how his operator experience now shapes the way he evaluates early-stage companies at Las Olas VC.

We also get into why investors are often looking for reasons to say no, how inconsistent ARR or revenue numbers can create doubt, what founders should understand about portfolio construction, and why fundraising is ultimately a sales process built on trust.

Follow Inside Startup Funding for more conversations with founders, investors, and operators on what it actually takes to raise capital.

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 conversation. We also get into what really happens when your company gets brought up in a partner meeting, why your idea has to survive the “game of telephone” inside a firm, and the deck mistake that causes founders to bury the most exciting part of their story.

One of Charlie’s clearest takeaways: “The narrative aspect of a pitch is something that most people miss. You are trying to convince somebody of something, not just present information objectively.”

Charlie O'Donnell

https://www.linkedin.com/in/ceonyc/

https://www.thisisgoingtobebig.com/

Helena Fogarty

https://www.linkedin.com/in/helenafogarty/

Follow Inside Startup Funding for more conversations with founders, investors, and operators on what it really takes to raise capital.

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 institutional capital. We also discuss why retail isn’t a shortcut to success, how to evaluate different funding options, and what investors are really looking for in today’s market.

Topics we cover:• Why venture isn’t right for most CPG brands• When founders should consider raising• What real traction looks like vs vanity metrics• Why retail isn’t a silver bullet• Alternative funding options for CPG• How to approach investor conversations• The reality of building as a founder• What VCs misunderstand about CPG• Advice for founders getting started

Sponsors:Aster AI — Aster AI is 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 and Park — https://www.28thpark.com/

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 deal. We also get into spray-and-pray outreach, deck mistakes, governance rights, liquidation preferences, and the fundraising process errors founders make over and over again.

Andrew also shares lessons from building through the dot-com era, moving into angel investing, helping build industry verticals at Dreamit, and working closely with founders across proptech and construction tech. It’s a practical conversation about credibility, process, and how to raise more effectively in a tougher market.

Topics we cover:

• Why founders usually have less valuation leverage than they think
• The only real way to improve a term sheet
• Why investor FOMO speeds up deals
• Why spray-and-pray outreach hurts credibility
• The sales discipline founders need in fundraising
• What Andrew looks for when evaluating founders
• Common pitch deck and process mistakes
• What founders should do after receiving a term sheet
• Why networking should start long before a raise

Andrew Ackerman: http://www.linkedin.com/in/andrewbackerman
https://x.com/andrewackerman
https://www.instagram.com/andrewbackerman/

Links to Andrew's book:

https://www.andrewbackerman.com
https://www.amazon.com/Entrepreneurs-Odyssey-Approach-Startup-Success/dp/1032883545/ref=tmm_pap_swatch_0