Stay ConnectedEvery founder has 1 goal: find product-market fit. We interview the world’s most successful startup founders on the 0 to 1 part of their journeys. We’ve had the founders of Reddit, Gusto, Rappi, Glean, Cohere, Huntress, ID.me and many more.
We go deep with entrepreneurs & VCs to provide detailed examples you can steal. Our goal is to understand product-market fit better than anyone on the planet.
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Copyright: © 2024 A Product Market Fit Show | Startups & Founders
Noah Greenberg grew a content-distribution product from zero to $1M ARR in just one year (and to $4M in 2 years) by focusing on a single channel most founders underrate: LinkedIn. He posted insights daily, highlighted key players in his industry, and made it impossible for prospects not to notice him.
In this episode, Noah reveals the exact step-by-step playbook, including how to structure 3-month pilots for fast feedback, craft DMs that actually get replies, and pick the right content “watering holes” so your future customers come to you eager to sign.
If you're a founder trying to figure out your go-to-market approach, you need to see what Noah did.
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Why You Should Listen
1. Turning LinkedIn into a Free PR Engine – Noah shows how daily micro-posts drive high-value leads without needing to go viral.
2. Finding Your First 10 Customers with 3-Month Pilots – Short trials = instant feedback on who’ll stay and who’ll churn.
3. Never Stop Triangulating – How 50 customer conversations per month reveal the right product, price, and packaging.
4. Selling without Selling – The “this isn’t a pitch” call that makes prospects lean in and ask, “Wait, how do we buy?”
5. Earning Credibility at Scale – Noah’s “watering hole” posts spark real engagement from decision-makers (and reel in 5-figure deals).
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Keywords
B2B Sales, LinkedIn Strategy, Early-Stage Growth, Founders’ Playbook, Bootstrapped Startup, Content Distribution, Sales Prospecting, Pilot Contracts, Outbound Leads, Product-Market Fit
Timestamps
(00:00:00) Intro
(00:02:35) Stacker's Origin Story
(00:06:00) How to generate warm leads
(00:15:53) How to use LinkedIn for lead gen
(00:21:42) No One Wants To Be Pitched
(00:26:06) How to get feedback on pricing
(00:38:08) LinkedIn Go-To-Market Strategy
(00:42:20) Breaking Above The Noise
We break down the real startup playbook: fake users, fake traction, real secondaries. From starting a company with zero customers, to raising millions and launching a VC fund that's built to lose money, Jack shares the blueprint for getting rich (without working hard).
Forget chasing product-market fit.
Start chasing growth, money, and, most of all, hype.
Why You Should Listen
Keywords
startup fundraising, pivot strategy, early stage VC, founder mistakes, product market fit, startup advice, venture capital, startup growth, entrepreneur mindset, founder stories
(00:00:00) Intro: Why Quitters Win and Fundraising Beats Traction
(00:02:54) Ex-Googlers Can’t Hack It as Founders
(00:03:12) Raising Money is Your Only Job
(00:10:49) How to Fake User Growth & Create FOMO
(00:14:18) Quit Fast, Pivot Faster
(00:15:28) Jabroni Capital: The World’s Worst VC Fund
(00:26:26) Hiring Hacks: How to Convince People to Join Your Startup
(00:28:27) Adam Neumann: Hero or Villain?
(00:38:16) The Real Jack Kuveke: Satire, Startups, and Why VC is Broken
Wes Bush wrote the original bestseller on Product-Led Growth—and then watched everyone try to copy Dropbox and Slack without truly getting it. Now, he’s here to break down exactly what goes wrong when early-stage founders jump into PLG, how to spot your product’s “million-dollar free problem,” and how to fix the three biggest onboarding gaps that sabotage new users.
He’ll show you why some sales-led companies die when they try freemium, how to carve out a simpler “first strike” moment, and the reason you need bumpers (like an onboarding checklist) to guide people to success. If you’re still using the “Request a Demo” button, this episode could totally transform your approach and give you a self-serve funnel that scales faster than any sales deck ever could.
Why You Should Listen
1. Make Users “Smell the Cologne” – Learn Wes’s approach for letting users experience the core value before they buy.
2. Turning Complex Setups into a No-Brainer – How to map out product, skill, and knowledge gaps so anyone can get started.
3. Bowling Alley Onboarding – A framework to slash unnecessary steps, guide users to that “aha” moment, and cut churn.
4. Freemium vs. Free Trial vs. Reverse Trial – How to pick the perfect model for your startup.
5. Sales-Led to Product-Led – Why some founders fight this shift, and how to pull it off without blowing up your funnel.
Keywords
Product-Led Growth, PLG Strategies, SaaS Onboarding, Freemium Model, Free Trial Optimization, User Adoption, Customer Success, B2B SaaS Growth, Onboarding Framework, Go-to-Market Tactics
Timestamp
(00:00:00) Intro
(00:01:27) What is Product Led Growth
(00:04:37) When to use PLG
(00:18:20) Why Simplicity is the key
(00:20:15) Wes's Favorite Case Study
(00:25:42) The Bowling Alley Framework for Onboarding
(00:31:02) Free Trials Must Have Progression
(00:36:28) Finding Those Ideal Limits on your Trials
Jeff Adamson co-founded SkipTheDishes, scaled it to 80% market share, and sold it for $200M—all before Uber Eats and DoorDash even got serious about Canada. He started with zero tech experience, got doors slammed in his face by restaurant owners, and had to personally place orders just to keep early partners engaged. Then, when Uber Eats launched in Toronto, backed by billions in funding, he thought it was over.
Instead, Skip became Canada’s dominant food delivery platform and got acquired for $200M.
Then Jeff did something even crazier—he decided to take on the banks.
With Neo Financial, he’s tackling Canada’s most entrenched industry, building a modern, full-stack digital bank from scratch. He's raised $100s of millions at a $1B valuation.
Why you should listen:
Keywords
SkiptheDishes, Neo Financial, entrepreneurship, delivery service, startup journey, market competition, founding team, restaurant industry, business growth, feedback loop, three-sided marketplace, startup journey, Canadian startups, entrepreneurship, financial services, exit strategy, partnerships, growth strategies, advice for founders
Timestamps
(00:00:00) Intro
(00:02:00) Gotta Have Thick Skin
(00:03:54) Skip's Origin Story
(00:07:18) Competing with Uber
(00:16:09) The First Few Restaurants
(00:22:45) Initial Demand
(00:26:28) Three-Sided Marketplace
(00:38:38) The Original Mission
(00:52:10) The First Year at Neo
(00:58:40) Product Market Fit
(00:59:55) A Piece of Advice
One of the most common questions I get is 'How do I know if I have product market fit?" Especially when you're in that gray zone where things are kind of working but they're not really taking off yet, how do you know if you have product-market fit or not?
That's exactly what we dive into here.
Why you should listen:
This podcast originally aired on Matt's podcast called Product Driven, because the topics were so relevant, I figured I'd post it here too.
Timestamps
(00:00:00) Intro
(00:00:55) How do you know if you have PMF
(00:06:33) Why some problems are good
(00:11:24) Solve a True Top of Mind Pain
(00:15:54) Why timing matters
(00:21:30) How to Know When to Pivot
(00:25:00) Asking the Right Questions to Customers
Edo Liberty left a high-paying job at AWS—where he was building AI at the highest level—to start Pinecone, a company no one understood. He pitched 40+ VCs, got rejected by every single one, and nearly ran out of money. Then, he flipped the pitch, raised $10M, and built one of the most important infrastructure companies in AI.
Then ChatGPT dropped.
Suddenly, Pinecone was the must-have database for AI apps, with thousands of developers signing up daily. The company exploded, leading to a $100M round led by Andreessen Horowitz and a 10x revenue surge.
If you’re an early-stage founder, this episode is a must-listen.
Why you should listen:
•How he went from from 40 VC Rejections to a $10M Seed Round
• Why he quit a High-Paying Job at AWS to start a Startup
• The game-changing shift that made VCs finally “get it”
•What really happened inside Pinecone when AI took off
•Why most founders misunderstand market timing and what to do about it
Keywords
AI, Machine Learning, Startups, Entrepreneurship, Vector Databases, Fundraising, SageMaker, AWS, Technology, Innovation, Pinecone, vector database, seed funding, ChatGPT, startup growth, business model, AI, infrastructure, early stage founders
Timestamps
(00:00:00) Intro
(00:07:50) Edo's Story
(00:12:27) The Early Days of Machine Learning
(00:32:23) Seed Funding
(00:42:09) Unsustainable Scaling
(00:53:41) Told You So
(00:59:24) A Piece of Advice
Jon Yoo’s startup wasn’t working. He pivoted mid-YC, spent five brutal weeks without signing a single customer, and then—right after raising his seed round—his co-founder left.
Most startups die right there.
Instead, Jon figured out how to land massive customers like FiveTran and Snowflake. He grew from $500K to $2M ARR in 6 months.
Why you should listen:
•Navigating a founder breakup – What happens when co-founders split and how to handle it.
•The real YC experience – What worked, what didn’t, and how they pivoted mid-program.
•Landing major customers – How they got big logos like Snowflake.
•Fundraising insights – What really matters to investors at the seed and Series A stages.
•Why startups need forcing functions – The tactics that drove fast product development.
•How to know if you have product-market fit – The signals John saw at Sugar.
•Burn rate discipline – Why they raised millions but barely spent it.
Keywords
entrepreneurship, startups, investment banking, Salesforce, Y Combinator, founder dynamics, product market fit, scaling, cloud marketplaces, business strategy, fundraising, startup, YC demo day, customer acquisition, product-market fit, founder dynamics, early stage startup, team building, scaling, challenges
Timestamps
(00:00:00) Intro
(00:07:55) The Origin of Suger
(00:13:30) Going All In
(00:19:08) The first 10 customers
(00:24:20) The Hardest Pain Point
(00:30:29) Becoming Profitable
(00:37:05) Celebrate The Small Wins
(00:39:56) Finding Product Market Fit
(00:42:27) A Piece of Advice
This is one of the wildest founder journeys you’ll ever hear. Dmitry Gurski went from growing potatoes and picking mushrooms on a farm in Belarus to building Flo—a billion-dollar company with 75M monthly users that dominates the health and fitness category worldwide. He started Flo in a market already controlled by PayPal co-founder Max Levchin’s startup, which had $30M in funding from a16z. Today, Flo is 100x bigger than its once-dominant rival.
Dmitry shares raw, unfiltered startup truths—like why he got rejected by 200+ VCs, why 90% of startup failures are team-related, and why most founders are delusional about product-market fit. He breaks down how simplicity beats complexity in product, why retention is everything, and how deleting features can actually boost revenue.
If you’re a founder, this episode will fundamentally change how you think about perseverance, pivots, and building something that lasts. Listen now—you’ll be referencing this one for years.
Why you should listen:
Keywords
startup, entrepreneurship, product design, user retention, Flow app, health and fitness, early stage founders, product market fit, simplicity, user engagement, retention, user case, app development, entrepreneurship, product market fit, mobile apps, business strategy, team dynamics, failure, success, risk, uncertainty, decision making, market demand, competition, product-market fit, fundraising, entrepreneurship, startup success, female health
Timestamps
(00:00:00) Intro
(00:09:10) Why you Need to Keep it Simple
(00:13:10) Why B2C is All About Retention
(00:19:05) Why you Need to Delete Features
(00:24:14) PMF is about the Shape of the Curve
(00:39:17) When to Persevere, When to Pivot, and When to Quit
(00:42:22) More attempts = more success
(00:51:34) The Idea for Flo
(00:59:05) Finding Product Market Fit
(01:02:07) Advice for An Early Stage Founder
(01:10:22) A Potato Story
Saurav started a Groupon-like offering for SMBs in 2011. He quickly learned it wasn't going to work. He and his team pivoted and started driving leads to suppliers using Facebook ads. It worked and they generated revenue—but they were becoming a digital advertising agency. It wasn't at all what they wanted to build.
So they pivoted again. They used the cash from that business and built Perkbox. The idea was a subscription-based offering that that gave perks to SMB customers. Telcos started buying it and attaching it to their products to drive sales. Then, they pivoted again, this time moving away from customer perks and to employee perks.
This time, it worked. They grew from $2M in ARR to $14M in just 2 years. They kept growing and hit $36M in ARR. Then he sold the business to PE for $170M.
It took longer than expected. There were more pivots than expected. But it was a huge success.
Here's how it happened.
Why you should listen:
Keywords
PerkBox, Groupon, startup journey, business model, SMB market, marketing strategies, recurring revenue, partnerships, entrepreneurship, exit strategy, venture capital, entrepreneurship, startups, employee benefits, social media marketing, capital efficiency, business growth, acquisition, rebranding, emotional marketing, lessons learned
Timestamps
(00:00:00) Intro
(00:01:48) The origin of Perkbox
(00:04:52) Going after SMBs
(00:12:16) The Pivot
(00:26:35) Creating Viral Ads
(00:32:28) Demo to Close Rate
(00:40:12) Selling to PE Firms
(00:49:38) A Piece of Advice
In 2005 most people didn't even have cellphones yet. Those who did used flip phones. That's when Noah started Olo, a webapp to let people pre-order coffee from nearby shops. Users had to login on web, add a credit card, create pre-made orders and then send a text to a preset number when they wanted to pre-order. It was way, way ahead of its time.
Noah and his team 7 years to hit $1M in ARR. In the meantime, they raised a round with 50% dilution the week before the financial crisis, went on live TV to an audience on 6M viewers and had to pivot from a marketplace to B2B SaaS.
But overtime smartphone penetration increased, on-demand ordering became a trend, and then, one day, Starbucks launched their app. All of a sudden, every single restaurant in the world wanted a way to let their users pre-order.
And there was Noah and his team at Olo.
Today, Olo is a public company worth over $1B and generating nearly $300M in sales. Here's the story of how it happened.
Why you should listen:
Keywords
Olo, Noah Glass, entrepreneurship, product-market fit, restaurant technology, mobile ordering, startup journey, business challenges, marketing strategies, innovation
Timestamps:
(00:00:00) Intro
(00:02:20) Building an app in 2005
(00:13:20) The Burn the Boats Moment
(00:16:31) Building A Network Business
(00:26:08) The Cold Start Problem
(00:30:33) A Happy Accident
(00:36:55) Going through the 2008 Financial Crisis
(00:51:20) Finding Product Market Fit
(00:57:20) Blueprint of Values
(01:05:11) Best Piece of Advice
(01:06:08) A Big Milestone
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