Conventional wisdom says the hardest part of building a startup is building the product.

Shanea Leven says the harder challenge is figuring out what customers will actually pay for.

Before co-founding Empromptu.ai, Shanea spent more than 15 years building products at companies including Google, eBay, Docker, and Cloudflare.

In this conversation, she explains why sales is every bit as complex as engineering, why customer interviews aren't enough to validate an idea, and why early-stage founders need to spend more time testing demand than perfecting roadmaps.

We discuss the case-study approach she uses to find customers, the controversial belief that the only real product validation is money, and what happened when a LinkedIn post generated a 1,000-person waitlist almost overnight. 

Shanea also shares how she used more than 100 customer calls to shape Empromptu’s direction, why she stopped fundraising when the company took  off, and the go-to-market challenges that still keep her up at night.

If you're a technical founder trying to figure out whether you're building something people truly want, this episode offers a practical framework for separating genuine demand from wishful thinking.

Listen to this episode if you're trying to figure out:

(3:16) What Is Empromptu.ai, and Who Is it For?

(6:25) Sales Is Just as Complicated as Engineering

(8:14) The Case Study Method for Finding Early Customers

(11:56) Why Al Is Rewriting the Product Playbook

(13:37)   The Only Real Product Validation Is Money 

(17:10) The S***ty Purple Website That Predicted Impromptu's Viral Launch

(21:38) What 100 Waitlist Calls Taught Shanea About Customer Demand

(26:28) "We evolved the platform."

(34:57) "Ninety-nine percent of VCs are great at one thing."

(36:20) The GTM Problem That Still Keeps Shanea Up at Night 

(39:02) A Process for Selecting Your First Sales/Marketing Hires

(40:59) Why She'd Hire a "Scrappy" Marketer Over a Former Meta Employee "Every Time"

(44:05) The Early Traction Signal She No Longer Trusts

(45:28) A 30-day Experiment Founders Can Run To Validate Their Idea

Shanea Leven

Empromptu.ai

Empromptu raises $2M pre-seed to help enterprises build AI apps, 12/9/2025, TechCrunch

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Thanks for listening!

 – Walter

If you're building a startup, there are easier industries to choose than healthcare.

Sales cycles are long, regulations are complex, and earning the trust of providers and patients takes years.

In this episode, Mayo Clinic Platform Accelerate Director Jamie Sundsbak explains how healthtech founders can improve their odds of success.

We discuss what Mayo looks for in founding teams, why the program focuses on product development instead of fundraising, how startups use clinical data and physician feedback to refine AI products, and what healthcare systems are actually buying in today's market.

Jamie also shares lessons from reviewing hundreds of startup applications, the founding team profiles that stand out, why some companies gain traction while others stall, and what founders should know before building in one of the world's most regulated industries.

Listen to this episode if you're trying to figure out:

Watch on YouTube: https://youtu.be/whrR0IVHEOY

(1:39) What Mayo Clinic Looks for in Early-Stage Healthtech Startups

(13:31) How Mayo Uses Clinical Data and Physician Feedback to Improve Products

(23:50) The Art of Creating Provider FOMO

(25:32) The Ideal Healthtech Founding Team

(29:29) Why OpenEvidence Won — and What Hospitals Are Buying Today

(36:03) Healthcare Is Hard. Here's Why Founders Keep Choosing It Anyway

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Thanks for listening!

 – Walter

Most startup advice assumes the biggest challenge is finding customers. But what happens when the demand is obvious and the real question is whether the technology can actually work at scale?

In this episode of Fund/Build/Scale, I sit down with Stanford professor and Inception Labs founder and CEO Stefano Ermon to discuss how a breakthrough research paper evolved into a venture-backed AI company serving enterprise customers.

Stefano explains why his team believed they needed a 10x advantage in speed, cost, or quality to compete with industry giants, and how they convinced investors to back an idea that was still largely unproven.

We explore the realities of building a deep-tech startup, including raising capital before product-market fit, assembling a world-class founding team, learning enterprise sales as a first-time CEO, pricing a new category of technology, and competing with companies like Google, OpenAI, and Anthropic.

Along the way, Stefano shares practical advice for technical founders trying to transform research into a business, de-risk ambitious ideas, and create evidence that investors can believe in before the market fully understands what they're building.

📺 Watch this episode on YouTube 

(0:00) From Research Paper to Startup

(2:11) Why AI Is So Expensive

(4:34) Turning Research into a Company

(7:47) The Bet Behind Inception Labs

(9:01) Raising Money for an Unproven Idea

(12:24) Building the Right Team

(14:27) Dividing Founder Roles

(16:32) Building Before Customers

(20:07) When Customers Started Calling

(21:47) Learning to Sell

(25:04) Pricing a New Category

(26:34) The Wrong First Customers

(31:16) Why Startups Can Beat Giants

(34:04) The 10x Rule for Startup Differentiation

(39:20) Building a Durable AI Company

(41:03) How to De-Risk a Deep Tech Startup

(42:40) The First 90 Days After Funding

(43:54) One Founder Lesson He Learned Too Late

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Thanks for listening!

 – Walter.

Most technical founders can explain how their product works.

Far fewer can clearly explain why a customer should care.

In this episode, Cribl CMO Abby Strong shares what she has learned from building go-to-market teams and helping scale one of the fastest-growing companies in data infrastructure.

Drawing on her background in IT operations, product, and marketing, Abby explains why founders often struggle with messaging, how to know when you've found product-market fit, and what it takes to build demand before you have a large team or budget.

We also discuss category creation, customer discovery, the early signals that the market is pulling your product, and why your first marketing hire is probably not a CMO.

Watch this episode on YouTube: https://youtu.be/9TnFwRgy2fw

[3:56] Why Technical Founders Struggle With Marketing

[09:58] When Should You Hire Your First Marketer?

[11:29] Marketing Before You Have A Marketing Team

[13:46] Why Marketing Takes Longer Than Founders Expect

[19:35] Your First Marketing Hire Is Probably Not A CMO

[25:23] Turning Features Into Outcomes

[27:15] Four Questions Every Founder Must Answer

[28:57] How To Understand A Technical Product

[32:44] Building Cribl's GTM Engine

[36:46] When The Market Starts Pulling

[42:09] Build Trust Before You Chase Scale

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Thanks for listening!

 – Walter

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.

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

Puneet Agarwal

Mayank Mehta

Gather

True Ventures

Gather Growth Platform

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Thanks for listening!

 – Walter

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:

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.

(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

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Thanks for listening!

 – Walter

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.

(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: [email protected]

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Thanks for listening!

 – Walter.

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.

(3:32) The Hiring Problem That Created Pearl Talent

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Thanks for listening!

 – Walter

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:

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?

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Thanks for listening!

 – Walter.