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

(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

• 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.

(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

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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📺 Watch Fund/Build/Scale on YouTube: https://www.youtube.com/channel/UCFFH4cs2B1BKatPGs8SFRJw

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.

(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?

• Ben Black
• Akkadian Venture Capital
• IPO markets look primed to accelerate in 2026, pwc, 12/12/2025

📥 Get the Fund/Build/Scale newsletter on Beehiiv: https://fundbuildscale.beehiiv.com/

📸 Follow Fund/Build/Scale on Instagram: https://www.instagram.com/fundbuildscale/

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Thanks for listening!

– Walter.