First Commit

This week we sat down with James Flynn, an investor at Sequoia. James focuses on growth-stage investments for Sequoia and was previously an investor at General Atlantic.  

During the episode, we cover James's journey to Sequoia, highlighting intellectual curiosity and his competitive spirit as key attributes in his path to the firm. The conversation features a number of fascinating perspectives across investing in "daring" companies, including James's take on the relative importance of business model / founder / market in making an investment decision. We also cover how James thinks about absolute valuation as opposed to a multiple, and how he believes junior investors can add value.  

James's energy is infectious and his eloquence and clarity of thought stand out, making the conversation one of our most fascinating yet. 

Episode Chapters:

1. Key personal characteristics - 2:19
2. James's journey post-college - 9:30
3. Breaking in to Sequoia - 12:55
4. Taking the shot - 13:55 
5. Underwriting thoughts - numbers support the story - 21:33
6. Sequoia's singular KPI - 27:45
7. How junior investors can add value - 30:10
8. Absolute valuation matters - 35:31 
9. James's areas of focus - 38:32 
10. Implications on education - 41:12
11. Quick fire round - 43:26

As always, feel free to contact us at [email protected]. We would love to hear ideas for content, guests, and overall feedback.

This episode is brought to you by Grata, the world's leading deal sourcing platform. Our AI-powered search, investment-grade data, and intuitive workflows give you the edge needed to find and win deals in your industry. Visit grata.com to schedule a demo today.

Fresh out of Y Combinator’s Summer batch, Overlap is an AI-driven app that uses LLMs to curate the best moments from podcast episodes. Imagine having a smart assistant who reads through every podcast transcript, finds the best parts or parts most relevant to your search, and strings them together to form a new curated stream of content - that is what Overlap does. Podcasts are an exponentially growing source of unique information. Make use of it! Check out Overlap 2.0 on the App Store today.

This week, we have Rahul Sonwalkar, Founder and CEO of Julius, on the show. Julius is your AI Data Scientist, where users can quickly analyze, visualize, and transform data.

Rahul covers his journey from traveling across the country to hackathons in college, the importance of not being afraid of failing as a founder, how Rahul seeks out mentors, the four key ways Julius delivers value, and how Julius continues to add AI to data analysis.

We also cover the decision to start selling bottoms up, how that enabled revenue in the early days, and how smarter models directly benefit Julius.

Episode Chapters:

1. Undergrad at UT Dallas - 1:47
2. Being okay with being wrong - 4:18
3. Overcoming ego - 7:15
4. The Julius DNA - 9:20
5. Your AI data analyst - 12:15
6. Building trust with Julius - 15:30
7. Maintaining infrastructure - 19:20
8. Building out new features - 22:32
9. Two kinds of AI startups - 27:13
10. The next wave of SEO - 29:07
11. Assessing talent - 32:12 
12. Quick fire round - 33:26

As always, feel free to contact us at [email protected]. We would love to hear ideas for content, guests, and overall feedback.

This episode is brought to you by Grata, the world's leading deal sourcing platform. Our AI-powered search, investment-grade data, and intuitive workflows give you the edge needed to find and win deals in your industry. Visit grata.com to schedule a demo today.

Fresh out of Y Combinator’s Summer batch, Overlap is an AI-driven app that uses LLMs to curate the best moments from podcast episodes. Imagine having a smart assistant who reads through every podcast transcript, finds the best parts or parts most relevant to your search, and strings them together to form a new curated stream of content - that is what Overlap does. Podcasts are an exponentially growing source of unique information. Make use of it! Check out Overlap 2.0 on the App Store today.

This week, we have Trey Holterman, Co-Founder and CEO of Tennr, on the show. Tennr automates manual tasks in healthcare operations using a proprietary LLM and has raised over $61 million in VC funding from Lightspeed, a16z, Y Combinator, and others. 

Trey covers his journey from captaining the Stanford rowing team to navigating improv comedy and building Tennr. We dive into how Tennr defines success through improved patient experience and why hard problems attract great engineers.

Trey also unpacks why his team avoids buzzwords like “AI”, despite having a clear real-world application of a LLM.

Episode Chapters:

1. How rowing influenced Trey - 2:33
2. Building leadership skills - 4:15
3. Dabbling in standup comedy - 8:04
4. Tennr's founding story - 10:10
5. How Tennr delivers ROI to customers - 13:25
6. Hard problems attract great engineers - 17:03
7. RaeLM (proprietary vision model) - 22:06
8. Positioning as Healthcare Cowboys - 26:43
9. Summoning God through a machine - 31:14
10. The future patient journey - 34:01
11. Quick fire round - 41:47

As always, feel free to contact us at [email protected]. We would love to hear ideas for content, guests, and overall feedback.

This episode is brought to you by Grata, the world's leading deal sourcing platform. Our AI-powered search, investment-grade data, and intuitive workflows give you the edge needed to find and win deals in your industry. Visit grata.com to schedule a demo today.

Fresh out of Y Combinator’s Summer batch, Overlap is an AI-driven app that uses LLMs to curate the best moments from podcast episodes. Imagine having a smart assistant who reads through every podcast transcript, finds the best parts or parts most relevant to your search, and strings them together to form a new curated stream of content - that is what Overlap does. Podcasts are an exponentially growing source of unique information. Make use of it! Check out Overlap 2.0 on the App Store today.

This week, we are chatting with Matan Lamdan, a cloud infra investor at CRV. Matan started his career as an officer in Unit 8200, the security unit of the IDF, before transitioning to investigative journalism. Now, Matan is a Principal on the infra team at CRV, where he primarily focuses on early-stage security investments. 

During the episode, we discuss the screening process for the IDF and how Matan ended up in the cyber intelligence unit (which is very well known in the valley). We also cover how chance encounters landed Matan in VC, the importance of being in the right networks, and how CRV acts as a thought partner to their founders. Matan also dives into where AI agents will impact security and why CISOs are excited about this opportunity. 

Episode Chapters:

1. Growing up in the US and Israel - 1:52
2. Serving in the IDF - 2:32
3. Transitioning to CRV - 7:41
4. Evaluating a team - 8:40 
5. Sourcing in Israel from SF - 11:40
6. Passing but staying in touch - 13:22
7. Winning deals - 15:47
8. Where Matan spends his time - 18:26
9. AI for pen testing - 24:15
10. If not VC? - 26:50 
11. Quick fire - 28:28

*Episode was recorded pre Wiz acquisition

As always, feel free to contact us at [email protected]. We would love to hear ideas for content, guests, and overall feedback.

This episode is brought to you by Grata, the world's leading deal sourcing platform. Our AI-powered search, investment-grade data, and intuitive workflows give you the edge needed to find and win deals in your industry. Visit grata.com to schedule a demo today.

Fresh out of Y Combinator’s Summer batch, Overlap is an AI-driven app that uses LLMs to curate the best moments from podcast episodes. Imagine having a smart assistant who reads through every podcast transcript, finds the best parts or parts most relevant to your search, and strings them together to form a new curated stream of content - that is what Overlap does. Podcasts are an exponentially growing source of unique information. Make use of it! Check out Overlap 2.0 on the App Store today.

This week, we are chatting with Bihan Jiang, a product lead at Decagon. Decagon is reimagining customer service with AI agents. The company recently raised a $65M Series B and is trusted by companies such as Eventbrite, Substack, ClassPass, Rippling, Notion, and more. 

We dive into her journey starting at Scale AI after Stanford, moving to the application side of AI, LLM capabilities powering Decagon, and how customers are using Decagon to elevate their customer experience. We also dive into how Decagon is powering email, SMS, and voice and how they adhere to customers' requests for accuracy and reliability.

Episode Chapters:

1. Growing up in Texas - 1:53
2. AI powered PM - 3:22
3. Career progression - 6:12
4. Customer support market - 8:58
5. Users of Decagon - 13:13
6. Can we automate 100%? - 16:28
7. Moving into voice AI - 17:25
8. Customer research - 22:22
9. Product roadmap decisions - 26:44
10. Joining an AI startup - 29:15
11. Ending questions - 32:37

As always, feel free to contact us at [email protected]. We would love to hear ideas for content, guests, and overall feedback.

This episode is brought to you by Grata, the world's leading deal sourcing platform. Our AI-powered search, investment-grade data, and intuitive workflows give you the edge needed to find and win deals in your industry. Visit grata.com to schedule a demo today.

Fresh out of Y Combinator’s Summer batch, Overlap is an AI-driven app that uses LLMs to curate the best moments from podcast episodes. Imagine having a smart assistant who reads through every podcast transcript, finds the best parts or parts most relevant to your search, and strings them together to form a new curated stream of content - that is what Overlap does. Podcasts are an exponentially growing source of unique information. Make use of it! Check out Overlap 2.0 on the App Store today.

This week, we sat down with Vasek Mlejnsky, CEO and Co-Founder of E2B. E2B is a platform for developers to run AI agents in the cloud securely.

We dive into the journey of starting a company with your best friend in the Czech Republic, building for AI agents before the hype, and why secure code execution is critical for scaling. Vasek also shares how E2B is becoming the go-to runtime for AI applications, the role of evals in agent development, and the challenges of pricing infrastructure while balancing user growth without hyperscaler-style pricing. 

Episode Chapters:

1. Growing up in Czech - 1:55
2. Building with your friend - 5:25
3. Starting a company in the US vs Europe - 7:05
4. State of AI agents - 11:15
5. Code execution before E2B - 14:00
6. E2B use cases - 16:10
7. Becoming AWS for AI agents - 19:00
8. Raising switching costs - 21:20
9. Computer use for agents - 26:48
10. Multi modal opportunities for agents - 30:26
11. Quick fire round - 34:45

As always, feel free to contact us at [email protected]. We would love to hear ideas for content, guests, and overall feedback.

This episode is brought to you by Grata, the world's leading deal sourcing platform. Our AI-powered search, investment-grade data, and intuitive workflows give you the edge needed to find and win deals in your industry. Visit grata.com to schedule a demo today.

Fresh out of Y Combinator’s Summer batch, Overlap is an AI-driven app that uses LLMs to curate the best moments from podcast episodes. Imagine having a smart assistant who reads through every podcast transcript, finds the best parts or parts most relevant to your search, and strings them together to form a new curated stream of content - that is what Overlap does. Podcasts are an exponentially growing source of unique information. Make use of it! Check out Overlap 2.0 on the App Store today.

This week, we sat down with Everett Cook, CEO and Co-Founder of Rho. Rho is a financial operating platform for fast-growing businesses.

We dive into ideating as a first time founder, discovering the cracks of business banking, building a product first organization, the trajectory of brick and mortar banks, how to structure customer service, and expanding past a BaaS solution. 

Episode Chapters:

1. Global Macro Investing - 1:56
2. Working with Mike Bloomberg - 5:15
3. Finding the "why" - 7:38
4. Working through systematic constraint - 11:10
5. Partnering with banks - 13:23
6. Competitive landscape - 19:45
7. AI enabling customer service - 23:00 
8. Nailing the ICP - 25:35
9. Banking in a box - 29:10
10. Future of Rho - 32:46
11. Ending questions - 33:35

As always, feel free to contact us at [email protected]. We would love to hear ideas for content, guests, and overall feedback.

This episode is brought to you by Grata, the world's leading deal sourcing platform. Our AI-powered search, investment-grade data, and intuitive workflows give you the edge needed to find and win deals in your industry. Visit grata.com to schedule a demo today.

Fresh out of Y Combinator’s Summer batch, Overlap is an AI-driven app that uses LLMs to curate the best moments from podcast episodes. Imagine having a smart assistant who reads through every podcast transcript, finds the best parts or parts most relevant to your search, and strings them together to form a new curated stream of content - that is what Overlap does. Podcasts are an exponentially growing source of unique information. Make use of it! Check out Overlap 2.0 on the App Store today.

This week, we sat down with Finn Murphy, General Partner at Nebular. Nebular is an early-stage VC fund based in NYC that invests in the US and Europe.

We dive into building and selling his first company, how angel investing can sharpen your investing skills, whether Seed investing is a 15-year career, winning investments in Europe, and aligning LPs with your fund strategy. 

Episode Chapters:

1. Growing up in Ireland - 1:50
2. Joining VC - 8:20
3. Founding Nebular - 11:25
4. Pitching LPs - 15:52 
5. Demystifying early stage venture - 20:54
6. A global mindset - 25:32
7. The future of Seed investing - 30:50
8. How would you invest in a Seed fund? - 36:28
9. Ending questions - 40:02

As always, feel free to contact us at [email protected]. We would love to hear ideas for content, guests, and overall feedback.

This episode is brought to you by Grata, the world's leading deal sourcing platform. Our AI-powered search, investment-grade data, and intuitive workflows give you the edge needed to find and win deals in your industry. Visit grata.com to schedule a demo today.

Fresh out of Y Combinator’s Summer batch, Overlap is an AI-driven app that uses LLMs to curate the best moments from podcast episodes. Imagine having a smart assistant who reads through every podcast transcript, finds the best parts or parts most relevant to your search, and strings them together to form a new curated stream of content - that is what Overlap does. Podcasts are an exponentially growing source of unique information. Make use of it! Check out Overlap 2.0 on the App Store today.

This week, we sat down with Robert Chandler, CTO and Co-Founder at Wordware. Wordware is a collaborative platform to build, iterate, and deploy AI agents.

We explore his initial interest in self-driving cars, finding PMF (knowing when to pivot), turning weak AGI into a narrow AI expert, and why prompting is the new programming with first principles in mind. 


Episode Chapters:

1. Entrepreneurship curiosity- 1:54
2. Building HeyDaily - 4:38
3. Pivot to agents - 9:42
4. End to end agent orchestration - 13:55
5. Long tail of use cases - 18:55
6. Future of Wordware - 20:56 
7. Feature prioritization - 24:24
8. Building with high switching costs - 27:48
9. Ending questions - 33:55

As always, feel free to contact us at [email protected]. We would love to hear ideas for content, guests, and overall feedback.

This episode is brought to you by Grata, the world's leading deal sourcing platform. Our AI-powered search, investment-grade data, and intuitive workflows give you the edge needed to find and win deals in your industry. Visit grata.com to schedule a demo today.

Fresh out of Y Combinator’s Summer batch, Overlap is an AI-driven app that uses LLMs to curate the best moments from podcast episodes. Imagine having a smart assistant who reads through every podcast transcript, finds the best parts or parts most relevant to your search, and strings them together to form a new curated stream of content - that is what Overlap does. Podcasts are an exponentially growing source of unique information. Make use of it! Check out Overlap 2.0 on the App Store today.

This week, we sat down with Jonathan Baer, CEO and Co-Founder at Overlap. Overlap is an AI assistant that creates daily, personalized playlists of clips about anything you’re interested in

We explore navigating public opinion at Meta, why business school is good for founders, and the team of AI agents focused on making curated Overlap content. Jonathan also offers helpful advice for applying to YC (hint: new wave of consumer AI) and the value add from the accelerator.


Episode Chapters:

1. Public Policy x tech - 2:13
2. Starting at GSB -7:05
3. Genesis for Overlap - 11:58
4. Podcast market - 14:00
5. LLM based clipping algorithm - 16:55
6. Overlap use cases - 21:55
7. Applying for YC - 26:05
8. Financial element of YC - 30:31
9. Quick fire round - 35:00 

As always, feel free to contact us at [email protected]. We would love to hear ideas for content, guests, and overall feedback.

This episode is brought to you by Grata, the world's leading deal sourcing platform. Our AI-powered search, investment-grade data, and intuitive workflows give you the edge needed to find and win deals in your industry. Visit grata.com to schedule a demo today.

Fresh out of Y Combinator’s Summer batch, Overlap is an AI-driven app that uses LLMs to curate the best moments from podcast episodes. Imagine having a smart assistant who reads through every podcast transcript, finds the best parts or parts most relevant to your search, and strings them together to form a new curated stream of content - that is what Overlap does. Podcasts are an exponentially growing source of unique information. Make use of it! Check out Overlap 2.0 on the App Store today.