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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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

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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.

(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

• 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.

(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.”

Ngetha Waithake

Norrsken 22

TymeBank

AutoChek

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Thanks for listening!

– Walter

In this episode, I’m joined by Jon Callaghan, co-founder and managing partner at True Ventures, and Julie Bornstein — CEO and co-founder of Daydream, founder of The Yes, and former COO of Stitch Fix — to break down what investors really evaluate in the first 18 months of a company’s life.

Drawing from their shared history as investor and founder, we talk candidly about runway, hiring before certainty exists, conviction versus ego, and how trust between founders and investors gets tested when plans change.

Julie explains how she approached budgeting and milestones for The Yes as a non-technical founder, while Jon shares how early-stage investors assess learning, decision-making, and leadership long after the pitch meeting ends.

(2:43) Jon: “Julie and I met in graduate school.”

(4:24) Julie chose a different VC firm for her first seed round at The Yes

(10:33) How would Jon have assessed The Yes if he didn’t know Julie?

(13:14) Julie: “Runway is your best friend and your biggest gift.”

(14:59) How non-technical founders can sketch out a financial model

(22:37) Jon: “There’s an immense river of goodness that flows underneath Silicon Valley.”

(25:30) How did True Ventures size up SAM for The Yes?

(29:00) Only work with engineers who understand your problem

(31:25) Some of Jon’s post-check expectations for founders

(41:44) What are some questions founders should ask VCs in their first meeting?

(45:42) One experiment a pre-seed/seed-stage founder can try next week

(48:14) The final question

• Julie Bornstein
• Jon Callaghan
• True Ventures
• Daydream
• Top e-commerce veteran Julie Bornstein unveils Daydream—an AI-powered shopping agent that’s 25 years in the making, Forbes, 6/25/2025
• Pinterest to Acquire THE YES, an AI Powered Shopping Platform for Fashion, press release, 6/2/2022
• StitchFix

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Thanks for listening!

– Walter

For years, founders have been told to build a defensible moat. But in AI, where platforms, models, and capabilities can shift overnight, that advice is starting to feel outdated.

In this episode of Fund/Build/Scale, Simular CEO and co-founder Ang Li talks about what it actually means to build a company when the underlying technology won’t sit still.

Rather than evangelizing agents or predicting the future of work, Ang gets unusually candid about fragility, speed, judgment, and how founders should think when technical advantages may be temporary by default.

The conversation digs into small-team execution, founder productivity, decision-making under uncertainty, and the uncomfortable question many AI founders avoid: what if the next platform update eats your product?

Note: This interview was recorded before Simular closed its $21.5M Series A in December 2025.

(1:52)  What is Simular, and how does it work?

(6:11) How Ang and co-founder Jiachen Yang connected

 (9:00) How much time passed between Day Zero and serving their first customer?

(13:54) The moment Ang realized " this is gonna be like something huge."

(17:21) How he approaches founder-led sales and what he looks for in a GTM hire

(26:34) Maintaining cohesion when you're leading a distributed team

(32:23) Should you hire a new employee, or build a new agent?

(34:50) Why Ang made talking AI gorillas part of Simular's GTM strategy

(38:20)"If everyone becomes too cautious there, that actually prevents the innovation part."

(43:55) "There's never a moat on anything."

(51:16) The final question

Ang Li

Jiachen Yang

Simular

Meet the AI Agent with Multiple Personalities, Wired, 4/16/2025

Simular Raises $21.5M to Build Autonomous Computer Agents, 12/2/2025

What is Robotic Process Automation (RPA)?, IBM

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Thanks for listening!

– Walter.

When most founders look at markets dominated by Google or Apple, they see a dead end. Ariel Seidman saw an opening.

Before founding Hivemapper, Ariel helped scale Yahoo Maps during a period when search and mapping were rapidly evolving. That experience gave him a front-row seat to how large-scale mapping systems are built — and how technical, capital, and organizational constraints shape the pace of innovation at scale.

In this episode, he breaks down what it really takes to build a startup against giants: why data moats matter more than UI, how to layer products instead of attacking incumbents head-on, and how insider knowledge can become an unfair advantage — if you’re willing to unlearn Big Tech habits that don’t translate to startups.

We also dig into Hivemapper’s decentralized approach to mapping, the role of physical AI and real-world data, the tradeoffs behind crypto incentives, and why the future of maps looks more like a spatial intelligence platform than a navigation app.

If you’re thinking about taking what you’ve learned inside Big Tech and applying it to your own startup, this is a conversation you’ll want to hear.

(2:11) What is Hivemapper?

(6:34)  Scaling Yahoo Maps: Lessons from an Early Market Leader

(9:04) Why Capital and Infrastructure Matter More Than Design

(11:49) From Insider to Founder: Deciding to Build Again

(15:00) Customer Discovery at Scale: Coverage, Accuracy, and the Long Tail

(19:10) Beyond Navigation: Maps as a Spatial Intelligence Platform

(22:46) Big Tech vs. Startups: Some Skills Transfer — and Some Don't

(27:31) Building Against Giants by Building One Layer at a Time

(31:39) Creating a Double Flywheel (and Making it Spin)

(45:10) The Final Question

• Ariel Seidman
• Hivemapper
• Beemaps
• Hivemapper network blog
• Hivemapper Raises $18M From Multicoin Capital to Create the World’s First Decentralized Mapping Network, 4/5/2022
• Bee Maps, Powered by Hivemapper, Raises $32 Million to Scale the Next Generation of AI-Powered Mapping, 10/6/2025

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Thanks for listening!

– Walter.