Dan's first app made over $1M in two months. Then Facebook sent a cease and desist and killed it. His next company, Mode Mobile, grew revenue 32,481% in three years and ranked #1 on the Deloitte Fast 500. Then his crypto advertisers went bankrupt, revenue fell from $25M to $8M, and he cut half his staff. No VC wanted a declining Series B. So he raised $5M from his own users in three months—then $75M more.

In this episode, Dan breaks down how paying people to use their phone actually makes money, why revenue concentration and not growth is what nearly killed Mode, and how to run a creator-led marketing campaign at $30 a video.

Why You Should Listen

• Why the product market fit that feels insane is often the kind that dies fastest.
• How building on someone else's API cost him two different companies.
• Why extending your payback period is the fastest way to run out of cash.
• How to know within $20K to $30K whether creator-led marketing works for you.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Mode Mobile, Dan Novaes, crowdfunding, Reg A, consumer apps, rewards apps, creator-led marketing, UGC creators, user acquisition, revenue concentration, Android apps

Chapters

• 00:00:00 Intro
• 00:03:09 The App He Built In A Week
• 00:06:38 $1M In Two Months
• 00:08:25 Facebook Shuts It Down
• 00:15:39 The Pivots Before Mode
• 00:20:42 32,481% Growth To The Fast 500
• 00:26:26 Revenue Concentration Nearly Kills It
• 00:31:50 How Paying People To Play Works
• 00:37:53 Creator-Led Growth For $30 A Video
• 00:47:09 What Makes A Crowdfund Work

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Keith raised a $43M Series B for Tome. The product had 20 million users. But retention was terrible and nobody cared enough to complain. So he turned it off before he knew what he'd build next, went from 70 people to 7, and started over. Lightfield just closed a $47M Series A.

In this episode, Keith breaks down how he knew Tome would never grow up, why customers lighting up your Slack at 3am is the signal you actually want, and the exact playbook he used to sell an AI-native CRM to YC founders before he charged them a dollar.

Why You Should Listen

• Why angry customers are a better signal than 20 million happy ones.
• How to know when optimizing metrics will never re-inflect your business.
• Why you have to kill the old product before you can find the new one.
• How to win founders with free software and events instead of cold email.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Lightfield, Keith Peiris, Tome, pivoting a startup, AI native CRM, agentic system of record, cutting burn, go-to-market, selling to YC founders, launch videos, B2B SaaS

Chapters

• 00:00:00 Intro
• 00:02:27 The Customers Who Were Hopping Mad
• 00:07:41 20M Users, Almost No Retention
• 00:09:27 When Your Business Works But Won't Inflect
• 00:11:24 Why His Board Said Burn the Boats
• 00:18:29 Turning Off the Product Before Knowing What's Next
• 00:22:13 Reinventing the System of Record
• 00:30:25 How to Sell to YC Founders
• 00:36:04 Making a Launch Video Hit a Million Views
• 00:44:08 The One Piece of Advice

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Aaron started Vestwell in 2016. Two years in, he had $500K in ARR and an investor asking if it would ever make money. During the 2021 bull market, VCs told him 401ks were too boring—they were busy chasing crypto. Then Morgan Stanley signed. Today Vestwell has 2.5 million people saving on the platform, over $200M in ARR, and just raised $385M at a $2B valuation.

In this episode, Aaron breaks down why he white-labeled everything instead of building his own brand, how losing the JP Morgan bid as a 40-person startup still turned into one of his largest partnerships, and how a methodical cap table let him raise a Series A on a couple hundred thousand in revenue.

Why You Should Listen

• Why letting your customers keep their brand beats competing with them.
• How to raise a Series A with only a few hundred thousand in ARR.
• Why losing an enterprise deal is the start of the sale, not the end.
• Why you never regret firing someone too soon.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Vestwell, Aaron Schumm, fintech, 401k, retirement savings, enterprise sales, channel partnerships, white label software, Series A fundraising, Morgan Stanley

Chapters

• 00:00:00 Intro
• 00:02:05 The Morgan Stanley Deal That Proved PMF
• 00:08:32 A 401k So Bad It Started a Company
• 00:10:23 Building V1 in a Regulated Industry
• 00:17:07 Turning Advisors Into a Sales Channel
• 00:23:57 Raising an A on $200K of Revenue
• 00:31:16 Too Boring for the Crypto Bull Market
• 00:38:45 Losing JP Morgan, Then Winning It Back
• 00:43:23 Never Regret Firing Too Soon

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Andrew spent two and a half years selling AI contract review to lawyers. It stalled at $800K. He rebuilt the company around finance teams and grew that to $10M. Then he demoed a little internal tool on the side at his own conference, and nobody wanted to talk about anything else. It did $350K in five weeks. He sold the $10M business and went all in on the side tool—Within went from zero to nearly $20M in 18 months.

In this episode, Andrew breaks down the 30-and-100 rule he uses to validate every idea, how he turned every customer conversation into a database that tells him what to build next, and why nine out of ten experiments have to fail.

Why You Should Listen

• Why 30 conversations validate an idea and 100 customers reveal product market fit.
• Why the thing everyone asks about matters more than the thing you launched.
• How to tell that slow growth is a market problem, not a go-to-market problem.
• How to run four bets a quarter with a kill metric on every one.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Within, Klarity, Andrew Antos, enterprise AI, AI transformation, pivoting a startup, enterprise sales, legal tech, finance automation, AI agents, customer discovery, voice of customer

Chapters

• 00:00:00 Intro
• 00:02:04 The Side Tool Everyone Wanted
• 00:04:26 $350K in Five Weeks
• 00:05:42 AI for Lawyers Before AI Worked
• 00:12:44 Stuck at $800K
• 00:13:43 Choosing Finance Over Legal
• 00:17:40 The 30 and 100 Rule
• 00:24:59 Selling the $10M Business
• 00:32:17 Building a Company Data Brain
• 00:40:01 Nine of Ten Bets Fail

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AJ spent two years selling health benefits with no customers and no references. His competitors told buyers their service was free. He charged a flat fee and told the truth about where the money actually went. Two years in, at $10M ARR, a Fortune 500 company called him. Judi Health just raised $400M at a $3.25B valuation.

In this episode, AJ breaks down how he beat three Fortune 15 giants by operating 70% more efficiently, why he spent zero on marketing for two years and let customers sell for him, and the one hiring signal he refuses to ask about directly.

Why You Should Listen

• Why $10M ARR still felt like nothing against three Fortune 15 competitors.
• How to sell healthcare when your answer to "who are your customers" is "just you."
• Why he spent $0 on marketing and made customers the brand ambassadors.
• How he spots A players without ever asking them about the mission.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Judi Health, Capital Rx, AJ Loiacono, pharmacy benefit management, PBM, healthcare startup, enterprise sales, transparent pricing, bootstrapping, self-insured employers, hiring for mission

Chapters

• 00:00:00 Intro
• 00:02:11 Why Healthcare Has No Shortcuts
• 00:05:34 What Judi Health Actually Does
• 00:11:27 Opacity As A Business Strategy
• 00:15:12 Bootstrapping In A Regulated Market
• 00:21:50 Selling The First Risky Customers
• 00:27:15 Winning Bids When Rivals Look Free
• 00:33:37 Zero Marketing And A Service Moat
• 00:42:20 Hiring For Mission And A Players
• 00:52:35 Founder Advice On Focus And Discipline

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Niklas quit law school to install CCTV cameras in iPhone repair shops. Eight years later he sold that business to private equity at 26. Then he went after the most boring software in the world: the 1997 tool engineers use to design the wiring and plumbing inside buildings. He spent $150K on a website before he had a product and DM'd engineers on Reddit to find his first users. His first month of sales was $1.5M, all enterprise. Endra has now raised $75M, including a $50M Series A led by a16z.

In this episode, Niklas breaks down why he spent $150K on brand before there was a product, how DMs in Reddit engineering threads turned into $300K enterprise contracts, and the hiring principles he used to screen the first 50 employees.

Why You Should Listen

• Why spending $150K on brand before you have a product can be the right call.
• How DMs in Reddit threads turned into $300K enterprise contracts.
• Why your customer's competitors are your best sales channel.
• How to know when 80% output is actually enough to sell.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Endra, Niklas Lindgren, MEP engineering, AI for construction, vertical AI, enterprise sales, brand building, Reddit marketing, hiring principles, agentic design software

Chapters

• 00:00:00 Intro
• 00:02:23 $1.5M of Enterprise Revenue in One Month
• 00:04:22 Why Enterprises Couldn't Say No
• 00:06:04 What Endra Actually Does
• 00:08:27 Law School to CCTV Cameras
• 00:12:06 Recruiting Two Goldman Engineers
• 00:17:11 Finding Users in Reddit Threads
• 00:26:02 $4M, $20M, Then $50M From a16z
• 00:35:00 Spending $150K on Brand Before a Product
• 00:40:11 The Hiring Principles Manual

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Colin spent eight years building Looker into a $2.7B Google acquisition. Then he left to compete with his own product. He thought traction would take a month—it took nine. A hundred demos got him five verbally-committed customers, and he lost all five. So he spent two months killing bugs, went on one podcast, and won every single trial that came out of it. Omni just raised over $250M.

In this episode, Colin breaks down how to tell the difference between a product that's genuinely better and one the market just doesn't want, why founding with $30M didn't stop them from staying stingy, and the LinkedIn playbook that turned 6,000 connections into a 90% response rate.

Why You Should Listen

• Why losing every deal doesn't mean the idea is wrong—and how to know the difference.
• Why real differentiation shows up as "wow" moments in demos, not signed contracts.
• The LinkedIn social-selling playbook that built Omni's first pipeline.
• Why hiring sellers from your old industry hands you their Rolodex on day one.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Omni, Colin Zima, Looker, business intelligence, BI tools, enterprise SaaS, AI analytics, social selling, LinkedIn outbound, founder-led sales, innovator's dilemma

Chapters

• 00:00:00 Intro
• 00:01:58 The Moment of True Product Market Fit
• 00:06:16 Losing All Five Deals and Doubling Down
• 00:10:43 Leaving Looker to Compete With Looker
• 00:17:39 Founding With $30M and Staying Stingy
• 00:22:09 A Hundred Demos Before the Flywheel
• 00:32:15 No Silver Bullet—Just Do More of Everything
• 00:38:32 The LinkedIn Social-Selling Playbook
• 00:46:07 Hiring the Best People You've Worked With

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Rafael launched a crypto insurance product in 47 states, backed by a real carrier. Everyone told him it was genius. Nobody needed it. He shut it down with $2M left in the bank, fired almost everyone, and rebuilt with two engineers on $20K a month. Notch just raised $30M.

In this episode, Rafael breaks down how a POC he entered through the back door turned into a seven-figure contract, why "isn't everyone doing this?" is the feedback you actually want, and how to tell whether an enterprise deal makes you a real company or just their dev shop.

Why You Should Listen

• Why "that idea is genius" is a warning sign, not a compliment.
• How entering a POC last still made them the front runner.
• Why the enterprise deals that scale need zero customization.
• How to stop hiding your idea and go straight to your dream customers.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Notch, Rafael Broshi, AI agents, insurance technology, customer experience automation, regulated industries, enterprise sales, POC strategy, pivoting a startup, on-prem deployment

Chapters

• 00:00:00 Intro
• 00:02:00 The Moment of True Product Market Fit
• 00:10:07 One Enterprise Deal or Ten
• 00:15:24 A Genius Idea Nobody Needed
• 00:24:33 Picking the Right Wave to Ride
• 00:34:37 Down to $2M, Firing Almost Everyone
• 00:41:48 Getting Enterprise to Take Your Call
• 00:48:07 The POCs That Aren't Real POCs

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Ben and his co-founder had no product, no law enforcement background, and no pitch—just an offer to help detectives solve cases. One commander took a chance, handed them background checks, and said "let's see what you can do." They worked out of that police department every day for 18 months. Peregrine just raised $250M at a $6.8B valuation.

In this episode, Ben breaks down how researching every police captain in the Bay Area landed their first design partner, why working as free crime analysts for 18 months was "the purest form of method acting," how forward-deployed engineers drove them from $1M to $3M to $10M ARR, and the 120% RFP prep that won a contract written for a billion-dollar competitor.

Why You Should Listen

• Why doing your customer's job is the fastest path to product market fit.
• How two founders with no product convinced a police department to let them in.
• Why over-investing in deployment became a growth engine, not a margin problem.
• How obsessive research wins enterprise deals when you have zero credibility.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, Peregrine, govtech, public safety technology, forward deployed engineers, selling to government, enterprise sales, data integration, design partners, Ben Rudolph

Chapters

• 00:00:00 Intro
• 00:01:07 The Moment of True Product Market Fit
• 00:11:51 Getting a Police Department to Say Yes
• 00:16:45 Slow Growth and Word of Mouth
• 00:19:49 Forward-Deployed Engineers Before They Were Cool
• 00:27:34 Cracking Government Go-To-Market
• 00:34:08 Winning an RFP Written for Someone Else

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Damien left his job to start a startup solo. Two years later, Nebulock closed a $25M Series A. In between: 90 customer interviews in 90 days, a year of design partners, and a Fortune 500 deal that closed in 6 weeks.

In this episode, Damien breaks down how his 90-in-90 customer discovery sprint killed his original architecture before he wasted money building it, how his design partner program converted 100% into paying customers, and how a POC playbook needing just 2 hours of customer time closed a Fortune 500 in 6 weeks.

Why You Should Listen

• How 90 customer interviews in 90 days saved him from building the wrong product.
• Why every single design partner converted into a paying customer.
• How a 2-hour POC playbook closed a Fortune 500 in just 6 weeks.
• Why procurement—not your champion—decides how fast your deal closes.

Keywords startup podcast, startup podcast for founders, product market fit, finding pmf, cybersecurity startup, solo founder, customer discovery, mom test, design partners, enterprise sales, POC process, AI security, Nebulock, Damien Lewke

Chapters

• 00:00:00 Intro
• 00:01:20 The Moment of True Product Market Fit
• 00:11:33 Going Cold Turkey as a Solo Founder
• 00:23:07 90 Interviews in 90 Days
• 00:36:44 Raising $8.5M Off a Manifesto, Not a Deck
• 00:39:36 Every Design Partner Converted to Paid
• 00:44:00 Building a Repeatable POC Playbook
• 00:48:20 The Procurement Black Hole

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