Fund/Build/Scale

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.

Building an early-stage startup isn’t just about the technology — it’s about earning trust before the proof exists.

In this episode of Fund/Build/Scale, I’m joined by Jeff Smith, CEO and co-founder of 2nd Set AI, a startup building generative image and video tools for media, entertainment, and sports organizations.

Jeff is a repeat founder navigating a familiar but uncomfortable phase: selling complex, unproven AI into large enterprise organizations that are curious about generative technology — and deeply wary of it at the same time.

We talk about why his team pivoted away from an early market that wasn’t ready, how they earned investor trust without product-market fit, and what it actually takes to sell AI into organizations where legal, brand, and compliance concerns can stop a deal cold.

This conversation isn’t about overnight success. It’s about iteration discipline, founder-investor trust, and the realities of selling emerging technology to skeptical enterprise buyers.

RUNTIME 31:28
 

EPISODE BREAKDOWN
(2:10) What is 2nd Set AI?

(2:53) How/why the company pivoted from fashion to entertainment

(8:34) How 2nd Set AI landed its first paid engagement

(12:15) Effective product education helps overcome sales objections

(16:45) Founders beware: enterprise AI adoption gets bogged down by compliance issues

(19:25) “I’m not sure I believe in a lot of moats right now.”

(25:47) How Jeff measures progress toward PMF

LINKS

Jeff Smith

Saurav Pandit

2nd Set AI

2nd Set AI Launches to Help Entertainment, Media and Sports Enterprises Create and Deliver Generative Images and Video for Global Audiences - While Protecting IP and Elevating Brands, 8/13/2025

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Thanks for listening!

 – Walter.

As African startups mature, the leap from seed to growth brings a new set of challenges — longer fundraising cycles, institutional expectations, governance, and the realities of scaling across fragmented markets.

In this episode of Fund/Build/Scale, I sit down with Ngetha Waithaka, partner at Norrsken22, one of the continent’s leading growth-stage funds. We talk about how investors evaluate African startups as they approach Series A and beyond, how founders can tell whether their business is truly venture-scale, and when bootstrapping may be the smarter path.

We also dig into practical issues founders don’t always hear about early enough — institutional readiness, governance, cross-border expansion, and how currency volatility shapes long-term outcomes.

If you’re an African founder preparing for growth capital, or an operator trying to understand what serious investors are actually looking for, this episode offers a clear-eyed look at what it takes to build something durable.

RUNTIME 46:36
 
EPISODE BREAKDOWN
(2:13) Ngetha unpacks Norrsken 22’s origin story and thesis

(5:15) Should you bootstrap, or is your idea venture-scale?

(10:30) Before talking to VCs, make sure you can demonstrate “institutional readiness”

(15:05) African founders “have to start very early on the governance journey.”

(20:17) Ngetha works with founders “from all over the map.”

(22:55) Should African founders use Silicon Valley as a success model?

(29:43) A few thoughts on currency fluctuations and international expansion

(37:41) Where is Norrsken 22 looking for opportunities?

(39:09) The difference between building for one market and building for Africa

(44:24) Ngetha’s advice to his younger self: “Success is not a linear journey.”

LINKS
Ngetha Waithake

Norrsken 22

TymeBank

AutoChek

 

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Thanks for listening!

 – Walter