Fund/Build/Scale

Hiring is one of the hardest things for first-time founders to get right, especially if you’re building a distributed team that spans the globe.

For this episode, I spoke to Isaac Saul Kassab, co-founder of Pearl Talent, a recruiting firm that helps startups hire offshore teams. We break down the underlying hiring frameworks founders can actually use, whether you’re hiring locally or globally.

We get into how to write tighter job descriptions, evaluating candidates beyond their resumes, and why so many founders waste time interviewing the wrong people. Isaac also walks through how he thinks about onboarding as a filtering mechanism and why early hiring mistakes are often unavoidable (but manageable if you move quickly).

If you’re building your first team — or trying to fix a hiring process that just isn’t working — this episode gives you a practical starting point.

How to define a role around outcomes instead of responsibilities

Why you should cut 30–40% from your job description before you post it

The interview questions that surface real signal (and filter out noise)

How to assess curiosity, coachability, and long-term fit

Why onboarding should be designed to expose failure early

The most common mistakes founders make when hiring offshore

What kind of hiring failure rate to expect as a first-time founder

RUNTIME 31:31
EPISODE BREAKDOWN
(3:32) The Hiring Problem That Created Pearl Talent
(9:56) How to Fix a Broken Hiring Process (Sourcing, Vetting, Onboarding)
(14:08) How to Evaluate Candidates Beyond the Resume
(17:25) Why Most Founders Hire the Wrong People
(22:05) “If You Don’t Invest in the Person, You Get Failure”
(25:29) Your First Offshore Hire: Start by Working Backwards
(28:18) A Simple Hiring Playbook You Can Use Tomorrow

LINKS

Pearl Talent

Isaac Saul Kassab

Monty Ngan

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Thanks for listening!

 

 – Walter

Technical founders don’t usually struggle with what they’re building.

They struggle with explaining it clearly, quickly, and in a way that makes someone want to invest.

In this episode, I spoke with Sheena Jindal, Managing Partner and Founder of Sugar Free Capital, about how technical founders can de-risk themselves before they ever get on a call with a VC.

Sheena meets hundreds of founders each quarter and often decides within the first 30 seconds whether a conversation is worth continuing.

That makes the early moments of a pitch — how you show up, how you frame the problem, and how you explain your edge — far more important than most founders realize.

We cover:

How to use the first five minutes of a pitch to earn a second meeting

The most common mistakes technical founders make with investors

How to translate complex technology into a clear, compelling story

What actually counts as a defensible moat in an AI-driven market

How to think about investor fit and building the right cap table

What successful founders do in the first 90 days after raising capital

This is a tactical conversation for founders building in deep tech, AI, and infrastructure, especially those without a built-in network or fundraising playbook.

RUNTIME 42:54
EPISODE BREAKDOWN
(3:31) Overview of Sugar Free Capital

(9:36) How to Prepare for Your First Investor Meeting

(12:19) Common Mistakes Technical Founders Make With Investors

(16:31) How Inauthenticity Sabotages Founders

(19:42) Bridging the Gap Between Deep Tech and Clear Storytelling

(24:19) How Technical Founders Should Find the Right Investors

(30:12)  What Successful Founders Do in the First 90 Days After a Raise

(34:18) How Top Technical Founders Show Up in the Room

(36:10) From First Meeting to Term Sheet: What to Expect

(39:20) Rapid Fire: Six Questions in Four Minutes

LINKS
Sheena Jindal

Sugar Free Capital

Sugar Free Capital raises $32M inaugural fund to back early-stage MIT founders, 10/6/25, TechCrunch

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Thanks for listening!

 – Walter

Startup employees are encouraged to believe in the mission. But IPO timelines now stretch well past a decade — and many never happen at all.

In this episode, Ben Black, co-founder and managing director of Akkadian Ventures, explains how tech workers can think more strategically about the equity they’ve helped create.

Drawing on more than 750 secondary transactions, Ben walks through how employees can evaluate a company’s liquidity posture before accepting an offer, exercise options intelligently, understand the real value of their shares, and access secondary buyers — whether through structured programs or more proactive approaches.

We also dig into the psychological side of selling: when to take money off the table, how to avoid overestimating future upside, and why “loyalty” shouldn’t mean ignoring your own financial reality.

Ben shares real-world examples of employees using secondaries to fund major life events — and even to bootstrap their own companies so they can retain more ownership and control from day one.

Founders and VCs get a lot of attention for the risks they take. This episode is about the people who often take just as much risk with far less margin for error.

* Information offered is for educational purposes and should not be considered financial advice.

RUNTIME 52:37
 
 BREAKDOWN
(2:12) How Ben got into the secondary market and founded Akkadian

(5:33) “The vast majority of really good companies now have secondary programs.”

(8:39) Secondaries generate “a very significant part of the return of the large funds.”

(9:57) Why are most companies still on a four-year vesting cliff?

(12:55) Things to consider when you’re 25% vested

(15:22) Why so many tech workers never exercise their vested options

(16:49) A framework for identifying the *right* time to sell

(21:26) How to access the secondary market if your company doesn’t offer a structured program

(30:09) “I do see a lot of bad behavior among employees… using information that they’re not supposed to use.”

(32:06) Startup employees: cultivate a strong relationship with your CFO

(34:08) The #1 reason why employees sell secondaries (and a few edge cases)

(38:44) “You have to be really skeptical, and you need to take a lot of shots on goal.”

(45:11) How many founders are bootstrapping startups using the secondary market?

(48:44) How long does it take to get liquid?

LINKS

Ben Black

Akkadian Venture Capital

IPO markets look primed to accelerate in 2026, pwc, 12/12/2025

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Thanks for listening!

 

 – Walter.

I interviewed Play Ventures General Partner Phylicia Koh to explore what founders outside of gaming can learn from two decades of game design.

Play Ventures began as a gaming-focused VC fund. Today, it also invests in what Phylicia calls “playable apps,” consumer products that combine utility with the engagement mechanics of games.

That doesn’t mean slapping on points and badges. It means understanding motivation, social dynamics, retention loops, and in-app economies.

We talk about:

What actually makes an app “playable” — and why most gamification fails

The difference between vanity retention and real engagement

Why founders should get comfortable with paid user acquisition 

What she wants to see at pre-seed (hint: can you ship?)

How to design for habit in categories like fintech, wellness, and spirituality

If you’re a domain expert building a consumer product and you’ve never seriously considered how game design might increase engagement and lifetime value, this conversation will give you a new lens.

RUNTIME 37:20
 

EPISODE BREAKDOWN
(2:33) “Play identifies as a gaming and also a consumer VC fund.”

(7:53) How she determines if gaming skills/practices will add value.

(11:19) How to pitch Play Ventures 

(14:50) "Can you ship? Because shipping is hard."

(18:05) Phylicia’s top success metrics for playable apps

(21:39) “You're going to need to use paid user acquisition."

(28:07) “If somebody has a good idea, I guarantee you somebody else around the world has that idea too.”

(32:46) An idea she’d like to back that doesn't exist yet

LINKS

Phylicia Koh

Play Ventures

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Thanks for listening!

 

 – Walter.

In this episode of Fund/Build/Scale, Sentry co-founder David Cramer joins host Walter Thompson for a candid, wide-ranging conversation about what founders actually struggle with — and why so much conventional startup advice falls apart in practice.

David shares how he dropped out of high school, taught himself to code, and turned a side project into Sentry, the error-tracking platform now used by millions of developers. From there, the conversation moves into the realities of venture capital, including why access and credibility matter more than most founders want to admit, and why you don’t raise venture money on small ambitions.

They dig into the difference between building technology and building a business, the pricing mistakes that nearly sank an otherwise healthy company, and why charging money isn’t enough — you have to charge enough. David also explains why endurance and effort matter more than cleverness, and why many startups fail simply because founders stop pushing too soon.

The episode closes with a rarely discussed topic: what you’re really buying when you advertise a tech company. Drawing on Sentry’s billboards and transit ads across Silicon Valley, David explains why attention often matters more than explanation — and why brand isn’t something founders can outsource.

By design, this conversation is frank, opinionated, and unfiltered.

RUNTIME 55:40
 

EPISODE BREAKDOWN
 

(1:56) "I've met a lot of Stanford grads that have not gotten very far in life."

(5:18)  How David realized Sentry was more than just a cool side project.

(9:25)  "Everything's an access game. This is why San Francisco is so valuable."

(15:16) "I would never advise somebody to just… go straight into the founder thing."

(19:59) " The day you raise money is the day you stop focusing on the technology."

 (23:13) What do seed-stage success metrics look like?

(26:49)  When it came to early pricing, "we just kind of iterated."

(32:34) Founders need "to push the business to the extremes of what it can become.

(36:58) When it comes to grind culture, " don't believe everything you read on the internet."

(40:13)  "For me, marketing is three things.”

(49:06) “I do a bunch of angel investing. I’m trying to do less of it, frankly.”

(51:51) The last question

LINKS

David Cramer

Chris Jennings

Sentry

Accel

Helping Developers See and Solve Quicker: Our Enduring Partnership with Sentry (Series E announcement, 5/4/2022

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Thanks for listening!

 – Walter.