Will, Founder of Phonely, shares his raw journey into Y Combinator—including sleeping in his car before a 3AM interview. He reveals how founders should interpret investor rejections, the real path to product-market fit, and top lessons a long the way. A must-listen for anyone navigating the early-stage PMF journey or getting funded!

Will Bodewes

https://www.linkedin.com/in/william-bodewes/

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EPISODE DESCRIPTION EXAMPLE

What really matters when applying to YC?

How to get your first $1

top learnings from fundraising

FOUNDER PROFILE:

Brooke Hopkins

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

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How do you close $100M from VCs like a16z & Sequoia?

Nic shared what he did and his most shocking learnings.

FOUNDER PROFILE:

Nic Kopp

https://www.linkedin.com/in/nicolas-kopp/

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SUMMARY

In this episode, Gil shares the raw journey of building Metadata — from validating the idea through consulting, to nearly running out of cash, to eventually raising a $35M+ Series B. He explains how doubling prices unlocked product-market fit, why retention beats new logos, and how adopting AI transformed the company. This is a candid look at the highs, lows, and lessons every founder needs to hear.

FOUNDER:

Gil Allouche

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

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MAIN POINTS:

Gil found product-market fit by doubling prices until customers pushed back.

He shifted focus from chasing new logos to retaining high-NRR customers.

Metadata survived by cutting 85–90% of workforce costs and replacing work with AI.

He validated the idea through consulting first, proving ROI before building software.

The company nearly died in 2019–2020 but survived through investor support and scrappy financing.

Raising Series A took two years and 100+ pitches, but Series B was oversubscribed.

His biggest lessons: pause to reassess, trust intuition, be transparent, and get a coach.

Teddy, founder of Fizz, shares how a side project at Stanford exploded into one of the fastest-growing Gen Z social platforms. From rejecting VC money at first to eventually raising $40M, Teddy explains how focusing on students’ needs fueled growth. This episode dives into product-market fit, the power of community launches, and building without chasing money.

Founder profile

https://www.linkedin.com/in/teddy-solomon-85a183188/

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HIGHITES

Raising $40M for a Gen Z social app

Stanford launch took off instantly

Building without chasing money

Saying no to VC money at first

The real launch: summer 2021 at Stanford

From Stanford success to nationwide phenomenon

What's do VCs ask during a pitch conversation? Here's a real pitch in San Francisco with a $25B AUM VC.

This is unscripted and it's the first time they met.

NEA Partner:

Andrew Schoen

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

YC Founder:

Berni Hausleitner

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

Gaurav Mishra, Founder of Proshort, shares how a single conversation led to his first big customer win and set the foundation for a multi-million-dollar raise. In this candid conversation, he breaks down the biggest growth unlocks, the vision that inspired investors, and the hype cycle pitfalls that every founder faces. If you're on the journey to PMF, this is the episode for you.

Julie Lein, Managing Partner at Urban Innovation Fund, shares what it takes to get funded in today's market. From mastering your pitch to leveraging AI and regulatory tailwinds, Julie breaks down how to stand out to investors. We also dive into her cold email formula, first meeting strategy, and what makes a founder unforgettable.

Top Moments

05:31 Why it's never too early to pitch and how progress between meetings wins investors.

11:42 Julie explains Urban Innovation Fund's AI-native and AI-accelerated investment approach.

16:58 Regulatory tailwinds: the underrated driver of billion-dollar opportunities.

24:17 Why evangelism and storytelling are now non-negotiable for founders.

33:09 Julie’s cold email formula that gets founders meetings (and checks).

38:45 Inside the first investor meeting: product demos, partner discussions, and market vision.

Gravity - Discover prospects with time-based signals https://bit.ly/40ALy6G

Check out Dub --> https://www.dubapp.com/

Check out Steven Wang, Co-Founder of Dub

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

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TIMELINE

00:05:00 - Raised a seed round on a vision during a hot market (Robinhood/Coinbase IPO)

00:13:19 - Immense conviction in the team despite market volatility

00:13:43 - Unreasonable belief is often the differentiator for winning

00:15:49 - Why it's better to raise before you have growth metrics

00:25:43 - Hiring mistakes: went after logos instead of fit

00:33:30 - Learning every aspect of growth and iterating on test ads

00:33:45 - Strategy: organic content that works → amplify with paid

Check out Alex Gurevich, Managing Director of Javelin Ventures

https://www.linkedin.com/in/alexg79/

https://www.javelinvp.com/?utm_source=chatgpt.com

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DESCRIPTION

Alex, Managing Director at Javelin Venture Partners, shares hard-won lessons from backing billion-dollar companies like MasterClass. In this episode, he breaks down what makes a truly defensible AI product and how founders can avoid the most common early-stage traps.

TIMELINE

00:17:19 — "The 'sit-on-top' LLM wrapper actually can be the most defensible product if executed right."

00:18:04 — "AI products, leveraging their own IP."

00:18:07 — "As the AI gets better, their product gets better — that's the compounding advantage."

00:20:18 — "They just sold our games business, but the insight was in how they packaged it."

00:21:38 — "How they're interfacing with the companies as they scale — that’s where real value emerges."