For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 3.

Kyle left his job as a hacker at the NSA to launch Huntress. He bootstrapped for 3 years and burned all his savings. One of his co-founders quit. He got into an accelerator program, but had to sleep in his car for 16 weeks because he couldn't afford a hotel.

Finally, 3 years in he'd hit $1.5M ARR. So he pitched 60 VCs for a Series A—and got 60 'no's. He was forced to raise a small, $1M inside round.

But then things changed:

2018: $1.5M ARR
2019: $5M ARR
2020: $10M ARR
2021: $20M ARR
2022: $40M ARR
2023: $70M ARR
2024: $100M+ ARR

Huntress is valued at $2B.

The investors who backed his $1M bridge are up 140x.

Now every VC wants to invest—and Kyle's the one saying 'no'.

Why you should listen:

How to know whether you should keep going or quit.
What it takes to get through the first few years at a bootstrapped startup.
Why revenue expansion is a huge lever for fast-growth (Huntress has 140% net revenue retention).
How starting a startup can impact your personal life and relationships.
How to work with partners to sell to long tail SMB customers.
Keywords
entrepreneurship, cybersecurity, product market fit, startup journey, military experience, SMB market, funding challenges, automation, human expertise, business growth

Timestamps:
(00:00:00) Intro
(00:2:01) Working at the NSA
(00:6:14) A big win in counter cyber terrorism
(00:10:00) What gave way to Huntress
(00:14:22) Pitching to a startup accelerator
(00:16:29) Adopting curiosity
(00:21:04) Getting ahead of cyber criminals
(00:26:00) Starting to grow
(00:32:50) Cult or conviction
(00:35:00) It takes grit
(00:39:50) Learning from people's lessons
(00:42:20) Cockroaches and underdogs
(00:46:10) Three strikes, I'm out
(00:52:56) Having a military background
(00:56:17) One piece of advice

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They were building a Segment competitor. It was working—customers were paying. But every sales call, prospects kept asking about the backend tech instead of the product.

So they killed the roadmap and pivoted. It took them 18 months to hit $1M ARR. Then they started growing. And so far, they've raised $350M.

Viraj walks through exactly how he validated the pivot, landed the first 10 customers, and why being outside Silicon Valley forced him to show more traction than everyone else.

Why You Should Listen

• How to know when your side feature is actually your real product
• The exact question to ask prospects to validate willingness to pay
• Why getting to $1M ARR slowly can set you up to scale faster
• How to compete when you're not based in Silicon Valley
• What talking to your first customer 4x a day for 2 months teaches you

Keywords

startup podcast, startup podcast for founders, open source startup, B2B SaaS growth, pivot strategy, developer tools startup, finding product market fit, early stage fundraising, design partners, commercial open source

00:00:00 Intro

00:01:46 Getting caught at the Coldplay concert

00:14:29 Deciding to Pivot From a Working Product to Something New

00:17:27 Building a Business Around Open Source Technology

00:19:38 Selling Before You Build

00:27:37 Talking to the First Customer Four Times a Day

00:30:51 Landing the First Ten Customers

00:35:10 Fundraising Without Silicon Valley Pedigree

00:38:48 When He Knew He Had Product Market Fit

Retry

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For the holiday break we are resurfacing some of our best episodes so far. Here is the best episode of season 2.

Here are the key lessons from the past 60 episodes that we've released to date. Each of the 5 steps to Product Market Fit is based on actual case studies with real examples you can use. It's a recap of everything I've learned over the last two years- you don't want to miss it.


Chapters:
(00:00:45) Mistakes Are Unavoidable But Avoidable Mistakes Are Unaffordable
(00:04:41) 1. Before Startup Mode, There's Research Mode
(00:07:16) 2. Only The Insanely Focused Survive
(00:10:49) 3. You Have to be IN the Market to WIN the Market
(00:14:08) 4. Forget Growth. Find Value.
(00:18:05) 5. Pivot Harder & Faster
(00:23:50) Recap

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David had a consumer app with 50,000 users and viral traction—and he shut it down. The retention metrics weren't as good as what he'd seen at Snapchat.

That difficult decision cleared the path for Juicebox, AI for recruiting that grew to $10M ARR in 2 years.

In this episode, David reveals how he pivoted to AI recruiting, generated millions of views with a simple LinkedIn demo, and ground through months of brutal churn to unlock 10x growth. If you want to know how to execute a flawless PLG strategy, run a hyper-lean team, and secure a $30M Series A from Sequoia, this is the blueprint.

Why You Should Listen

• Why you should kill some products even if they're going viral.
• How to launch a B2B product with zero budget.
• The "manual" playbook for fixing high churn.
• Why you should keep your team under 25 people even after raising millions.
• How to land an inbound term sheet from Sequoia.

Keywords

startup podcast, startup podcast for founders, product market fit, finding pmf, PLG strategy, viral marketing, pivoting, AI recruiting, Series A fundraising, Sequoia Capital

00:00:00 Intro
00:03:15 Learning Growth at Snap
00:13:01 Killing a Viral App with 50k Users
00:20:34 The 90 Second LinkedIn Video That Launched Juicebox
00:26:21 Fixing High Churn with Manual Work
00:33:04 Why B2B Products Only Need to be Marginally Better
00:42:27 Scaling to $10M ARR with Founder Led Sales
00:47:40 Raising a $30M Series A from Sequoia
00:50:12 The Moment of True Product Market Fit

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Jennifer went from VC to founder and immediately broke every rule in the book. When she pivoted Scribe from an automation tool to a documentation platform, her investors told her she had just killed the company. She ignored them.

Instead of polishing her product, she launched a "janky" offline MVP on Product Hunt to test for real market pull. Scribe is now used by 95% of the Fortune 500.

In this episode, Jennifer reveals the brutal truth about ignoring "smart" money, why you should run PLG and Enterprise sales simultaneously from Day 1, and how to tell the difference between pushing a boulder up a hill and chasing one down it.

Why You Should Listen

• Why you sometimes need to ignore your investors to save your startup.
• The "Boulder Test": The definitive gut check for knowing if you have true Product-Market Fit.
• How to validate a massive opportunity with zero marketing budget.
• Why the conventional wisdom about choosing between PLG and Enterprise Sales is wrong.
• How to turn executive hiring interviews into free mentorship sessions.

Keywords

startup podcast, startup podcast for founders, product market fit, PLG strategies, MVP testing, enterprise sales, go to market strategy, early stage growth, finding pmf, founder stories

00:00:00 Intro

00:02:21 1,200 Customer Interviews as a VC

00:22:07 How to Hire for Excellence

00:30:18 The Pivot from Automation to Documentation

00:39:17 Launching a "Janky" MVP on Product Hunt

00:49:09 The Boulder Test for Product-Market Fit

00:52:50 Doing PLG and Enterprise Sales Simultaneously

01:03:12 Ignoring Investors to Save the Company

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Alex built the original Snapchat filters-- and sold his company to Snap for $166M.

Then he left to start Higgsfield. The company just raised a $50M Series A to help brands create AI-generated video ads at scale.

We go deep on why he thinks Adobe is in trouble, how top advertisers are already producing 10,000+ ad creatives a year, and why the companies winning in AI video aren't building foundation models.

Why You Should Listen

• Why consumer AI apps are a trap (and what to build instead)
• How to drive early growth
• The economics of AI-generated video
• How to know when to pivot away from traction that has no long term

Keywords

startup podcast, startup podcast for founders, AI video generation, generative AI startup, social media marketing AI, B2B SaaS growth, founder pivot, AI startup fundraising, creator marketing, product market fit

00:00:00 Intro

00:06:29 Selling to Snap and Working With Evan Spiegel for Four Years

00:08:28 The Origin Story of HiggsField

00:17:47 The Real Use Cases for GenAI Video Today

00:27:26 The First Product and Why They Pivoted Away From Consumer

00:29:08 The $10 Billion Short Form Drama Market Nobody Talks About

00:33:26 Going All In on Social Media Advertising

00:41:16 When He Knew He Had Product Market Fit

Retry

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Eric spent 30 years in cybersecurity. Built and sold an MSSP to private equity for hundreds of millions. Then he started Tenex and hit $43 million in revenue in ONE YEAR.

This isn't theory. This is a founder who's done it multiple times breaking down exactly how AI-native companies are about to eat every services industry alive. If you're building anything that touches AI, services, or enterprise sales, this is the episode.

Why You Should Listen

• Why selling outcomes beats selling products every time
• How to close enterprise deals in 60 days instead of 12 months
• The difference between AI-native and AI-bolted-on companies
• Why founder-led sales is non-negotiable in the early days
• How to build for IPO from day one without slowing down

Keywords

startup podcast, startup podcast for founders, AI startup growth, founder-led sales, zero to one startup, enterprise sales strategy, AI native company, managed services startup, cybersecurity startup, product market fit

00:00:00 Intro

00:10:29 Selling His Last Company for $100Ms

00:15:10 The Origin Story of TENEX

00:36:47 How They Hit $43M ARR in Year One

00:43:27 The 30 Second Demo That Closes Enterprise Deals

00:47:10 Why Selling Outcomes Beats Selling Products

00:51:29 The Mechanics of Going From Zero to $40M ARR

01:01:09 Go to Market and Founder Led Sales

01:05:32 When He Knew He Had Product Market Fit

Retry

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Carta's Peter Walker is back with the freshest data on what's actually happening at the early stage—and it's not what you're reading on X. While headlines scream about record-breaking rounds, the reality on the ground tells a different story.

Seed deals are down. Time between rounds is stretching. And there's a brutal divide between the companies getting all the attention and everyone else.

We dig into the exact valuations, graduation rates, team sizes and revenue you need for Seed and Series A... plus why the lowest-quartile seed rounds are failing at twice the rate. If you're raising or planning to raise, this is the episode.

Why You Should Listen

• The round size that cuts your Series A odds in half
• Why smaller teams are winning (and what that means for your hiring plan)
• The real median valuations at pre-seed, seed, and Series A right now
• How long it actually takes to get from seed to Series A in 2024
• When taking secondary as a founder makes sense (and when it doesn't)

Keywords

startup podcast, startup podcast for founders, seed round valuation, Series A fundraising, startup fundraising data, venture capital trends, pre-seed funding, startup metrics, founder secondary, seed to Series A

Chapters:

00:00:00 Intro

00:02:46 Seed Valuations and Who Actually Graduates to Series A

00:06:58 What Founders Outside the Hot Cohort Should Do

00:11:44 Team Sizes Are Shrinking and Employees Are Getting Less

00:17:40 Crowded Categories and Competing with Foundation Models

00:24:47 Founders Starting Companies for the Wrong Reasons

00:33:32 When Founder Secondaries Make Sense

00:39:55 The Actual Median Valuations at Pre-Seed Seed and Series A

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