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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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

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

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

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.

(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

• Phylicia Koh
• Play Ventures

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

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

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

Thanks for listening!

– Walter.