Fund/Build/Scale

How AI-Native Startups Actually Get Built

What does it actually mean to build an AI-native company?
In this episode of Fund/Build/Scale, I talk with True Ventures Managing Partner Puneet Agarwal and Gather CEO/co-founder Mayank Mehta about how the startup evolved from an AI-powered customer feedback idea into a broader research and content platform for marketing teams.
We get into founder conviction before product-market fit, what investors actually look for when there’s little external signal, how the company reshaped its go-to-market strategy after realizing the original motion wasn’t working, and why Mayank rebuilt major parts of the business around AI workflows in real time.
There’s also a very tactical discussion about customer discovery, early hiring, AI-native operations, and a weekend growth experiment that produced more meetings in two weeks than the previous year of outbound efforts combined.
RUNTIME 51:33
EPISODE BREAKDOWN
03:18
What True Ventures Looks For at Seed
07:00
What Gather Actually Does
11:42
The Five-Slide Seed Pitch
17:21
What They Got Wrong Early
21:06
Rebuilding the Company Around AI
33:53
The Weekend GTM Experiment That Changed the Company
36:56
How Investors Read Founders Who Don’t Have Signal
41:15
Tactical Advice for First-Time Founders
49:18
One Experiment Founders Can Run This Week
LINKS
Puneet Agarwal
Mayank Mehta
Gather
True Ventures
Gather Growth Platform
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Thanks for listening!
 – Walter

Why Great Founders Are “Angry at the Problem”

For this episode, I interviewed Eugene Malobrodsky, partner at One Way Ventures and former founder of AnchorFree, the company behind HotSpot Shield, one of the first consumer VPN products to scale globally.
Before becoming a VC, Eugene spent 15 years building and scaling a startup through the 2008 financial crisis, painful layoffs, difficult fundraising environments, and the long grind from idea to acquisition. 
Today, he backs immigrant founders building applied AI, deep tech, fintech, healthcare, and enterprise startups at the pre-seed and seed stage.
Topics include:
Why many founders become founders for the wrong reasons
What venture capitalists really mean when they talk about “100x outcomes”
How to think about fundraising runway and dilution
Why technical founders often struggle with storytelling
What makes a startup venture-backable versus a profitable lifestyle business
The most common mistakes early technical teams make
How investors evaluate first-time founders with no track record
Why customer discovery matters more than building features too early
Why the best founders are often “angry at the problem” they’re trying to solve
He also spoke about what immigrant entrepreneurs misunderstand about networking in Silicon Valley, and the growing uncertainty around H-1B visas and startup immigration policy.
RUNTIME 56:28
 
EPISODE BREAKDOWN
(2:13) "I'm just not great at following directions and working for somebody else."
(5:44) How Working in VC Changed His Thinking
(7:42) What Founders Misunderstand About VC Funds
(20:53) A Practical Framework for Seed-stage Fundraising
(25:50) What Makes Him Take the Meeting
(31:19) Where One Way Ventures is Betting in Deep Tech 
(35:11) The Most Common Mistakes Technical Teams Make
(38:23) Why Founders Need a 90-second Story
(43:16) Growing Uncertainty for Immigrant Tech Workers and Founders
(51:33) Practical Networking Advice for First-time Founders
(54:38) The One Question H1-B Candidates Should Ask the CEO During an Interview
LINKS
Eugene Malobrodsky
One Way Ventures
Investing in Funds vs Investing as an Angel
One Way Ventures Expands to San Francisco from Boston with Eugene Malobrodsky, Co-founder of Consumer Privacy Company AnchorFree, Joining as Partner
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Thanks for listening!
 – Walter

Before There Is Proof: Build a Startup Story That Shows You Can Execute

A lot of early-stage founders can explain their company five different ways — and all five might be technically correct. The problem is that often, those answers don’t fully line up.
That gap in a startup’s narrative creates friction. 
Investors may understand the problem but still don’t feel like the story lands. Candidates may understand the product, but they’re not fully on board with the mission. Customers may hear the explanation but still struggle to repeat it clearly.
I’ve been inside meetings where the CTO described the company’s core value one way and the CEO had a different take.
In this episode, I break down the “narrative gap”: the distance between what a founder knows and what everyone else understands. 
I explain why technical founders often struggle to communicate even when they deeply understand their business and share several diagnostic frameworks you can use to test whether your story gives customers, investors, hires, and reporters confidence that you can execute.
RUNTIME 16:55
 
EPISODE BREAKDOWN
(1:52) Narrative is Not Decorative. Narrative is Load-bearing.
(3:30) Founder Diagnostics: 3 Questions That Pressure-test Your Story
(4:49) Your Message Is Not Your Pitch
(6:06) A Bridge Is Not A Destination
(7:42) Find The One Thing That Carries The Most Weight
(8:57) Ask, "What breaks without you?"
(10:30) Separate History From Story
(11:25) What's the First Sentence of Your Startup's Story?
(12:12) Pressure-test Your First Sentence In Different Rooms
(13:59) Putting It Together: Final Founder-narrative Diagnostic
(15:11) Use This Episode To Start Framing Your Narrative
 
I work with early-stage founders on narrative framing, media prep, fundraising communication, and public-facing storytelling. This is foundational work that helps your message hold up before investors, customers, candidates, reporters, and conference audiences.
If you’re getting ready to raise, hire, pitch, launch, or speak publicly, reach out: fundbuildscale@gmail.com
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Thanks for listening!
 
 – Walter.

How to Hire Your First Offshore Team Without Screwing It Up

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
RUNTIME 31:31
EPISODE BREAKDOWN
(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
LINKS
Pearl Talent
Isaac Saul Kassab
Monty Ngan
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Thanks for listening!
 
 – Walter
 

How Technical Founders Win the First 5 Minutes With Investors

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.
RUNTIME 42:54
EPISODE BREAKDOWN
(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
LINKS
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

Don’t Wait for the IPO: How Tech Employees Actually Get Liquid

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.

Turning Utility Into Habit: Beyond Basic Gamification

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.

The Day You Raise Money Is the Day You Stop Focusing on Technology

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.

Selling Unproven AI to Skeptical Enterprise Buyers

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.

From Seed to Growth: What African Founders Need to Know

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