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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