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.”

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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.”

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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.”

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What if the next great connector in Silicon Valley isn’t a human at all, but an AI with opinions, taste, and the courage to say no?

In this episode, we sit down with Andrew D’Souza, founder and CEO of Boardy, and the serial entrepreneur behind Clearco, to explore what happens when you combine behavioral psychology, network effects, and modern AI, then let it loose on one of the hardest problems in business, meaningful human connection. Andrew has spent his career building at the intersection of finance, technology, and trust. Now he’s building an AI “super connector” that doesn’t live in an app, doesn’t obey every command, and doesn’t optimize for clicks, but for goodwill.

Boardy is an AI board member you can call. Literally. It talks on the phone, remembers context, introduces you to the right people, and sometimes refuses if it thinks the intro would be bad for the network. In a world drowning in cold emails and shallow SaaS tools, Andrew is betting on something contrarian, that AI should feel less like software and more like a principled person.

In Todays Episode We Discuss:

00:01 – Breaking Things, Founder Embarrassment, and Why It Matters

03:30 – Studying the Brain, Behavioral Economics, and Human Decision-Making

06:40 – McKinsey, Facebook, and Getting the Startup Bug

10:10 – Early Lessons on Incentives and Why Referral Marketplaces Fail

14:45 – Becoming a Connector Between Silicon Valley and Canada

17:30 – The Origin Story of Clearco and Access to Capital

22:10 – Financing the DTC Boom and Creating a New Category

27:40 – When Scale Outgrows the Founder, Stepping Aside as CEO

31:50 – Discovering GPT-3 and the Clear Angel Experiment

36:10 – The Problem with Personal CRMs and Human Memory Limits

39:40 – Network Effects, Voice AI, and the Birth of Boardy

44:30 – Why Voice Is the Most Human AI Interface

48:20 – Judgment, Trust, and Saying No in Network Design

52:51 – The Future of AI, Imagination, and Human Connection

Andrew also shares a moonshot vision, Boardy as an AI Richard Branson, pulling the unique business out of every person, then helping them meet exactly who they need to make it real.

Memorable moments from the episode:

“Most people are being vastly unimaginative about what AI can do. The limitation isn’t the models, it’s our imagination.”

“The worst case of a bad introduction is wasted time. The best case is it changes your life. That asymmetry matters.”

Andrew started his career studying how the brain works. Now he’s building something that plugs directly into how humans actually connect. From simulating neurons to orchestrating networks, this episode is a glimpse at a future where AI doesn’t replace relationships, it upgrades them.

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Most people don’t break into venture by following the map. They do it by ignoring it, burning it, then drawing a new one from scratch.

Sarah Romanko is an investor at Geek Ventures, where she backs immigrant founders building deeply technical companies in AI and robotics. Before that, she stitched together fellowships, startup roles, speaking gigs, and a real estate job, all while building a network so strong it eventually pulled her into VC. No Ivy League halo. No neat career ladder. Just relentless curiosity, stubborn conviction, and a willingness to bet on herself when there was no safety net.

Geek Ventures focuses on founders the traditional system often overlooks, operators with real domain depth, strong technical moats, and the grit to build far from the spotlight. Sarah’s work sits at the intersection of talent spotting, founder empathy, and fast decision-making, all shaped by her own unconventional path into the industry.

In Todays Episode We Discuss:

00:01 Welcome and Guest Introduction

01:01 Sarah’s Early Curiosity and Business Background

02:26 Breaking Into Venture Without a Clear Path

04:26 Leaving Stability and Betting on Herself

05:24 The 32 Slide VC Interview Deck Strategy

07:54 Where Ambition and Drive Come From

09:55 Discovering Venture Capital and Founder Empathy

11:46 Advice for Aspiring VCs

14:18 Geek Ventures Investment Thesis

15:57 Learning to Prioritize Deals and Move Fast

17:45 Missing Deals and Investor Regret

19:21 Post Mortems and Learning from Failure

20:29 How Geek Ventures Supports Founders

22:09 Building Community and VC Culture

23:44 What Makes a Pitch Stand Out

25:34 Easy No’s and Red Flags for VCs

26:56 Market Trends and Emerging Managers

29:06 Redesigning Venture Capital

31:12 Fast Decisions and Due Diligence Tradeoffs

32:03 Remote First VC and Team Culture

33:47 Long Term Career Vision and Legacy

36:17 Common Fundraising Mistakes

37:09 Overhyped vs Underrated Startup Trends

38:12 Dream Investor Dinner

38:37 Frameworks and Mental Models

39:41 Lessons from Judging Hundreds of Pitches

40:47 The Hardest No

42:33 Rapid Fire Close

Along the way, Sarah shares hard-earned lessons from missed deals, fast-moving rounds, difficult no’s, and the surprising power of staying true to your beliefs when everyone in the room disagrees.

The throughline is simple but uncomfortable: venture doesn’t reward people who wait to be chosen. It rewards people who decide first, then do the work to make that decision inevitable.

Pull quotes:

“I didn’t have a backup plan, and that’s what forced me to make it work.”

“I want to back the founder I’d write a check to with my own money, even on a bad day.”

Sarah grew up watching Shark Tank. Now she’s on the other side of the table, backing founders who remind her what it feels like to believe before the world does.

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What if the best venture investors aren’t pattern matchers at all, but former operators who’ve spent decades stitching companies together, one partnership at a time?

Karen Page’s career reads less like a résumé and more like a relay race, sales floors to startups, startups to Big Tech, Big Tech to venture, with the baton always being go-to-market clarity. From helping scale Box in its formative years, to shaping enterprise partnerships at Apple, to now backing and advising founders as a General Partner at B Capital, Karen has seen how companies actually grow, and why most stall before they do.

In this episode, Karen breaks down what founders often miss when moving from early traction to real scale, and why “one plus one equals three” is more than a cute partnership metaphor, it’s a survival skill.

About the guest

Karen Page is a General Partner at B Capital and one of venture’s most operator-shaped investors. She was a founding executive at Box, where she built the partnership ecosystem and launched Box.org, later leading enterprise partnerships and GTM strategy at Apple. Today, she sits on and advises boards across SaaS, fintech, and digital health, helping founders turn early momentum into durable growth.

In Todays Episode We Discuss:

00:01 Welcome and Karen Page’s background

02:30 Early career in sales and building GTM foundations

04:20 Discovering partnerships as a growth lever

06:00 Scaling Box through ecosystem strategy

08:10 Exposure to venture while fundraising at Box

10:00 Transition from operator to investor

12:00 Why B Capital and building the early-stage fund

14:30 How Karen works with founders and boards

17:00 What great founders do differently as they scale

19:45 Evaluating investors and building the right board

22:00 Boardroom trust and decision-making under pressure

25:20 AI as a platform shift versus cloud and mobile

28:00 Go-to-market evolution in an AI-first world

31:00 Pricing, value creation, and capital efficiency with AI

34:00 Product-led growth versus sales-led at scale

36:30 Vertical software and overlooked markets

39:30 Talent, culture, and scaling leadership

43:00 How venture and startups will evolve

46:30 Timeless GTM principles and founder lessons

Memorable moments:

“Most of the time I’m an airplane, looking across the landscape. Every once in a while, I have to be an ant.”

“Clarity always wins. You can change channels, tools, and tactics, but if you can’t explain your value, nothing else matters.”

Karen’s journey is a reminder that venture isn’t about predicting the future, it’s about pattern recognition earned the hard way. Sales calls. Missed hires. Inflection points that only look obvious in hindsight. The same instincts that helped her connect companies at Box are now helping founders connect ambition to execution.

Different title. Same puzzle. Same question, how do you make one plus one equal three.

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Imagine spending decades inside the most buttoned-up corners of finance… then quietly deciding the real edge lives somewhere less liquid, less obvious, and way more misunderstood.

John McArthur is the Senior Partner and Chief Investment Officer at Krillogy, where he helps steward billions across public and private markets. Before that, he cut his teeth at firms like Morgan Stanley, and before that, he was a Division I quarterback, which explains a lot about how he thinks under pressure. Today, he sits at the intersection of wealth management, private markets, and long-horizon thinking, right as the old playbooks start to crack.

In Today's Episode We Discuss:

00:01 Origin Story and Early Career

01:55 From D1 Quarterback to CIO

03:10 What Krillogy Does

05:05 Scaling Through People and Culture

06:40 Early Move into Private Markets

09:10 Defining Private Markets

11:30 How the Ultra-Wealthy Allocate Capital

14:00 Access and Innovation in Private Markets

17:05 Fund-of-Funds and Diversification Logic

20:10 Liquidity and Time Horizon Management

23:05 Portfolio Allocation to Private Markets

26:10 Diversification and Dispersion in Venture

29:05 Public Market Return Expectations

32:00 Building Durable Portfolios

35:13 Transition to Rapid Fire

Along the way, John makes a contrarian case that doing nothing is still a decision, that risk is often mispriced because people hate illiquidity more than loss, and that the future of wealth management looks a lot more like architecture than stock picking.

Quotes worth sitting with:

“Doing nothing is a decision. It’s just not always the right one.”

“If you don’t have enough shots on goal in private markets, the probabilities just don’t work.”

John started his career calling plays on the field and ended up calling them across portfolios. Different arenas, same lesson, discipline beats adrenaline, process beats ego, and the long game always knows who’s bluffing.

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Imagine spending 15 years underwriting venture funds, only to realize the biggest risk isn’t the startups, it’s how little anyone actually measures the people backing them.

Eric Woo is the co-founder and CEO of Revere, a platform bringing data, transparency, and product thinking to how allocators evaluate and manage emerging venture funds. Before founding Revere, Eric sat on nearly every side of the table, pricing structured finance risk pre-GFC, evaluating hundreds of managers at Northgate and Top Tier, and helping institutionalize syndicates and nano-funds at AngelList. He’s a CFA, an engineer by training, and now a founder building infrastructure for private markets at exactly the moment venture is being forced to grow up.

In this episode, we unpack:

• Why venture underwriting is still mostly vibes, and why that breaks at scale

• The real signals Eric saw across hundreds of emerging managers that actually correlate with outperformance

• Why “value-add” is meaningless unless you can prove it, and how few GPs really can

• How AI changes venture operations versus venture judgment, and where humans still matter

• The tradeoff between concentration and volume, and when more shots on goal actually wins

• Why 1x DPI is a psychological unlock for LPs, and how secondaries quietly reshape fund strategy

• How venture is shifting from an artisanal craft into a distributed financial product

We also zoom out to the bigger pattern Eric sees forming: venture capital is moving toward new distribution, new fund structures, and new expectations of transparency, and the GPs who don’t adapt won’t survive the next cycle.

“Once you hit 1x DPI, everything becomes psychological. After that, it’s all upside.”

“The best VCs aren’t fungible. Founders know exactly who their first call is.”

Eric spent his career evaluating builders. Now he’s building the system he always wished existed, and in the process, forcing venture to look in the mirror.

In Today's Episode We Discuss:

00:01 – Eric Woo intro, Revere VC

01:00 – Engineering to finance pivot, CFA escape hatch

02:30 – Pricing CDOs before the financial crisis

04:20 – Front-row seat to the GFC

05:50 – First startup experience, search engine marketing

08:30 – Entering venture via fund of funds

10:40 – Early micro-VC and seed investing era

13:00 – Institutionalizing emerging managers

15:00 – Heuristics for backing new GPs

17:10 – Specialization and GP differentiation

19:30 – AngelList and the rise of syndicates

22:00 – Family offices and venture as participation sport

24:30 – Scaling challenges in GP–LP matchmaking

26:10 – What never changes in evaluating GPs

27:50 – Founder–VC relationship as core signal

29:10 – The origin of Revere

30:40 – Rating emerging managers with data

33:00 – Quantifying value-add

35:30 – Gaming the system vs real substance

38:00 – AI in GP self-assessment

41:00 – Structured vs unstructured data in venture

44:00 – AI, fees, and fund economics

47:30 – Transparency as LP differentiation

50:00 – Revere roadmap and Velvet merger

52:30 – Network effects and venture platforms

55:10 – Venture distribution and new capital channels

57:20 – Efficient frontier of early-stage venture

59:40 – Concentration vs volume strategies

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