A Product Market Fit Show | Startup Podcast for Founders

Description: Jack Kuveke returns to unpack the wildest startup news this month: from billion-dollar frauds and crypto scams, to OpenAI’s secretive $6.5 billion gadget project with Apple’s design legend Jony Ive. We dig into why big-name investors keep missing red flags, and why AI might be crushing entry-level tech jobs faster than anyone expected. Keywords startup scams, OpenAI Johnny Ive, Elizab...

After two pivots and nearly running out of runway, Merrill Lutsky found insane growth—scaling Graphite to tens of thousands of daily users and millions in ARR. He reveals exactly how Graphite landed its first massive enterprise customer, doubled revenue overnight by changing pricing, and turned user feedback into  momentum.  Merrill shares hard-earned lessons on recognizing true product-market fit...

Most early-stage founders get trapped in the chaos of endless tasks, there's always too much to do and not enough time. We go through the last 4 episodes to see what how the best founders prioritize. We also see why you can raise millions without real traction but can’t fake product-market fit, how positioning yourself for luck is as important as having a plan, why slow initial growth might b...

Dax built Lightspeed into a $1B ARR public company—even though he bootstrapped for the first 7 years. In this episode, he reveals exactly how he used a 4x pricing shift to create a global reseller machine that grew him to $10M ARR. He also breaks down why obsessing over design and deep customer empathy built the foundation for success.—and how stepping away from his comfort zone as an introverted...

Carta just released their report for Q1 2025. Peter is Head of Insights at Carta, and the person who owns their data practice. We sit down to talk about the largest trends he saw across fundraising, industries, graduation rates and even hiring practices.  Carta data shows that graduation rates from Seed to A are as low as they've ever been. Bridge rounds make you even less likely to raise an...

Kazi Ahmed took a small insight—seeing friends cash out from Amazon brands—and built Carbon6, a software roll-up startup, selling it for $210M just three years later.  But behind the quick success was a frantic scramble to survive. Aggressive acquisitions nearly ran them out of cash, forcing a brutal pivot from burning $1M per month to profitability and explosive organic growth.  This episode dive...

I break down my top insights from recent conversations with four founders who won in unconventional ways. You’ll hear how Noah turned LinkedIn posts into his primary sales channel (without ever going viral), why Dan’s startup survived a brutal 95% downround but ended up at $400M ARR two years later, how Adam turned a stagnant $3M ARR business into a $25M cash cow by solving one overlooked customer...

Public co-founder Jannick Malling shares exactly how he grew his startup from a tiny beta to millions of users—and hundreds of millions raised. He reveals why fractional shares changed the game for user acquisition, how the company cleverly seized on the GameStop moment to explode growth, and why relentless product focus was critical to scaling quickly.  He explains the mindset shift needed to nai...

Corporate spies stealing Slack messages. Adam Neumann raising another $100M (for WeWork 2.0?). AI startups hitting $34B valuations with zero revenue and ordering Ben & Jerry's ice cream over 15 payments with Klarna on DoorDash.  April was wild, and Jack Kuveke joins the show to unpack the chaos, controversy, and insanity behind the biggest startup headlines.  This is different than our no...

Forrest Zeisler spent 6 months hearing “no” from every potential customer he spoke to. One year in, Jobber had just three customers—paying $29/month. Today, Jobber generates over $100M ARR, has raised $180M in VC, and employs nearly 1,000 people. In this episode, Forrest shares the brutally honest story behind Jobber’s early days: months of rejection, maxing out credit cards, and nearly quitting....

He turned a personal travel tracker into an app with 10 million users and $10 million in revenue, with almost no funding. He reveals how ignoring conventional startup advice—like launching early, chasing revenue, or partnering for growth—was key to their viral success.  He realized everything growth was about word-of-mouth. So the key to success was obsessing over a single metric: NPS.  If you’re...

Jordan Boesch started 7shifts as a teenager helping his dad manage restaurant shifts. Today, his software runs scheduling for 50,000 restaurants. This episode dives into how Jordan bootstrapped early growth, why relentless focus on solving real customer pain mattered more than funding, and how tight partnerships supercharged his expansion.  Jordan also shares hard-won lessons on managing burnout,...

Wesley turned a simple AI headshot generator into a $10M ARR, profitable company—in just two years. He was fired from his job, broke in San Francisco, and, after getting rejected by 30 VCs, down to his last few thousand bucks. But Wesley saw a moment: generative AI was taking off, and no one was tackling AI headshots.  Fast-forward two years, and he’s doing $10M in revenue, profitable, with just 1...

Mike first raised $30M for a marketplace that never truly had product-market fit. Then he bet only $10K on ButcherBox. A few years later, he's doing $550M in revenue and he's profitable.  The difference is in his first startup he was just catering to investors— in his second one only to customers. If you’re an early founder chasing growth, listen to how Mike ditched vanity metrics, found...

Gopi Rangan has invested in 29 early-stage startups from scratch. He shares a simple but powerful approach to picking the right VCs, structuring your pitch (long-term vision + short-term plan + fuzzy mid-term path), and proving you are the sort of founder every pre-seed investor craves.  If you’re raising a pre-seed or seed, Gopi’s tips will make your process faster, more targeted, and a lot less...

Cardiologist Jim Min watched too many 50-year-olds die with no heart-attack warning. He co-founded Cleerly to automate detailed coronary scans—no invasive procedures, no endless manual work.  Yet healthcare’s glacial pace, payers, and federal approvals all stand in his way.  Hear how he’s testing AI across thousands of patients, fighting for universal insurance coverage, and coping with near-burno...

Adam Robinson once struggled with a stagnant email SaaS stuck at $3M ARR, but he kept experimenting until he found how to solve a problem no one else was tackling—and everything changed. Suddenly, buyers were begging for his identity-based marketing tool—so he spun out Retention.com and grew it to $14M+ in annual profit with no outside funding. In this episode, Adam reveals why he ignored “scalabl...

Dan Park joined Clutch when it was selling 20 cars a month . Then he grew it from $20M in 2019 to $200M in sales by 2022. He was one of Canada's fastest growing companies. Just as he was going to close a $100M round, the macro changed completely. Suddenly, he was left with only six weeks of cash. He was forced to go through a 97% down round at a $15M valuation. Just two years later, he not on...

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-mont...

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 Why you need...

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-...

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...

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: Why demo to close is an excellent leading indicator of P...

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...

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 h...