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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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

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

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.

(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

• David Cramer
• Chris Jennings
• Sentry
• Accel
• Helping Developers See and Solve Quicker: Our Enduring Partnership with Sentry (Series E announcement, 5/4/2022

📥 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.