What happens when an investor gets tired of guessing, and decides to rebuild the guessing machine itself?

Ali Dastjerdi didn’t stumble into AI for investing, he escaped into it. After years inside Insight Partners, swimming in deal flow, pattern matching companies, and watching great decisions hinge on incomplete information, he walked away to fix the system from the inside out.

Ali is the co-founder and CEO of Raylu, an AI-native platform helping private market investors move from thesis to conviction faster, with less noise and more signal. Before Raylu, he backed category-defining companies at Insight and lived the daily reality of sourcing, diligence, and missed timing. Today, he’s building AI agents that think like investors, not spreadsheets.

In Todays Episode We Discuss:

00:01 – Ali’s background, machine learning roots, and joining Insight Partners

03:40 – Why investing felt broken from the inside

06:15 – Early startup attempts and the pull back to company building

09:10 – The original Raylu idea and why it failed

12:30 – ChatGPT as a forcing function and the reset moment

15:20 – From infrastructure to vertical SaaS for investors

18:45 – Private markets as a sales and timing problem

22:10 – Why proprietary deal flow matters less than investors think

25:30 – Teaching AI agents what “good” actually means

29:40 – Replacing databases with adaptive investor workflows

33:15 – AI as conviction acceleration, not decision-making

36:50 – What investor work should never be automated

40:20 – How better context changes investment outcomes

44:30 – The future of venture in an agentic AI world

Along the way, Ali reframes venture capital as a sales problem, explains why most founders are pitching the wrong investors, and shares why being 5 percent better in a hyper-competitive market is often the difference between missing and winning generational companies.

We close where it gets personal. An investor who became a founder, now building tools for investors, wrestling with the same question from the other side of the table. If capital is the least differentiated product in the world, maybe the future belongs to those who combine judgment with intelligence, and know which parts should never be automated.

Quotes:

“Investors aren’t convinced by founders, they’re pattern-matching for believers.”

“AI shouldn’t make the decision. It should make you dangerous enough to make a better one.”

Subscribe on Spotify: https://open.spotify.com/show/6Ga6v0YUsHotLhjap67uu5

Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/ignite-conversations-on-startups-venture-capital-tech/id1709248824

Follow Ali Dastjerdi on LinkedIn: https://www.linkedin.com/in/ali-dastjerdi/

Follow Ali Dastjerdi on X: https://x.com/alidastjerdi

Follow Brian on X: https://x.com/brianrbell

Follow Brian on Linkedin: https://www.linkedin.com/in/bblinkedin/

Visit Our Website: https://www.teamignite.ventures

Subscribe to Our Newsletter: https://insights.teamignite.ventures/

👂🎧 Watch, listen, and follow on your favorite platform: https://tr.ee/S2ayrbx_fL

🙏 Join the conversation on your favorite social network: https://linktr.ee/theignitepodcast

What if the most important skill in venture capital isn’t pattern recognition, but patience?

In a world obsessed with overnight breakouts, Adam Besvinick has quietly built a different kind of edge, one forged by cold emails, long apprenticeships, and a stubborn belief that real companies take time. He’s the founder and managing partner of Looking Glass Capital, a pre-seed firm known for being the first yes to mission-driven founders in healthcare, climate, and the real economy. Before launching his own fund, Adam cut his teeth working alongside Chris Sacca at Lowercase, operating inside early startups, and later leading larger checks at a multi-stage fund, all of which shaped how he thinks about risk, conviction, and what founders actually need in their earliest days.

In this episode, Adam breaks down what most people get wrong about early-stage investing, and why the industry’s recent obsession with speed and optics has created some dangerous blind spots.

In Todays Episode We Discuss:

00:01 Welcome and Adam’s Background

03:00 Cold Emails and Breaking into Venture

07:30 Apprenticing with Chris Sacca at Lowercase

11:50 Early Operator Experience at Gumroad and Startups

14:50 MBA Decisions and Career Tradeoffs

19:30 Transition from Operator to VC

23:00 Venture as Psychology

28:30 Patience vs Speed in Venture Capital

33:00 The Myth of Fast Growth

36:00 AI and the Flattening of Teams

41:00 Why Series A Is Broken for Many Startups

46:00 Concentration vs Spray and Pray Investing

51:00 Founder Resilience and Hard Moments

56:30 Building Looking Glass Capital

01:01:30 The Future of Pre-Seed and Closing Thoughts

Adam also shares the personal experiences that reshaped how he underwrites founders, including moments when life hit far harder than any cap table ever could, and what those moments reveal about real resilience.

We close where we started, with patience. Not as a virtue signal, but as a competitive advantage.

As Adam puts it, “If you’re building for something that actually matters, the timeline will offend people who don’t understand it.”

Subscribe on Spotify: https://open.spotify.com/show/6Ga6v0YUsHotLhjap67uu5

Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/ignite-conversations-on-startups-venture-capital-tech/id1709248824

Follow Adam Besvinick on LinkedIn: https://www.linkedin.com/in/besvinick/

Follow Adam Besvinick on X: https://x.com/besvinick

Follow Brian on X: https://x.com/brianrbell

Follow Brian on Linkedin: https://www.linkedin.com/in/bblinkedin/

Visit Our Website: https://www.teamignite.ventures

Subscribe to Our Newsletter: https://insights.teamignite.ventures/

👂🎧 Watch, listen, and follow on your favorite platform: https://tr.ee/S2ayrbx_fL

🙏 Join the conversation on your favorite social network: https://linktr.ee/theignitepodcast

Most founders lose sleep over customers, competition, or cash. Alexander Wulff lost sleep over spreadsheets. That anxiety turned into a decade-long obsession, and eventually, into an AI CFO.

Alexander Wulff is the CEO and co-founder of ScaleUp Finance, and the builder behind NUM, an AI-powered CFO designed for startups and SMEs. Before fintech, he spent more than a decade building and exiting a deep-tech company, where he learned finance the hard way, by being forced to play CFO without really wanting the job. Today, he’s channeling that pain into a product that gives small teams access to real financial intelligence, without hiring a full finance department.

In Todays Episode We Discuss:

00:01 Introduction and Alexander Wulff’s background

02:05 From deep tech founder to fintech operator

04:12 Living the CFO problem as a founder

06:10 Early product market fit and rapid inbound demand

08:02 Viral distribution through financial reporting

10:01 Blending CFO services with software

12:30 Why finance tools must be 100% accurate

14:45 The shift from SaaS to agentic AI

17:20 Building NUM, an AI CFO

20:10 Orchestrating agents for financial accuracy

23:05 Ideal customer profile and SME focus

26:00 Finance complexity as companies scale

29:15 Democratizing CFO access with AI

32:10 Founder behavior and finance confidence

35:05 Lessons from scaling too fast

37:30 Long-term vision for AI in finance

Alexander also shares hard-earned lessons on scaling too fast, founder stress, and the mindset required to push through the moments when quitting feels rational.

We close where it all began. A founder staring at numbers late at night, wondering if they add up. Now, those same numbers talk back, clearly, calmly, and on time.

“Finance shouldn’t be the thing that keeps founders awake at night. That’s the problem we’re here to solve.”

Subscribe on Spotify: https://open.spotify.com/show/6Ga6v0YUsHotLhjap67uu5

Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/ignite-conversations-on-startups-venture-capital-tech/id1709248824

Follow Alexander Wulff on LinkedIn: https://www.linkedin.com/in/alexander-wulff-226b3225/

Follow Brian on X: https://x.com/brianrbell

Follow Brian on Linkedin: https://www.linkedin.com/in/bblinkedin/

Visit Our Website: https://www.teamignite.ventures

Subscribe to Our Newsletter: https://insights.teamignite.ventures/

👂🎧 Watch, listen, and follow on your favorite platform: https://tr.ee/S2ayrbx_fL

🙏 Join the conversation on your favorite social network: https://linktr.ee/theignitepodcast