A Product Market Fit Show | Startup Podcast for Founders

Jeff Adamson, co-founder of SkipTheDishes and Neo Financial, shares his remarkable journey from launching a food delivery service that dominated Canada to creating a billion-dollar digital bank. He discusses overcoming initial rejections and adapting strategies to build trust with customers. Jeff reflects on the emotional weight of selling Skip and how he pivoted to take on the banking industry. He also emphasizes the importance of resilience, continuous improvement, and the messy but crucial beginnings of any venture.

In this engaging discussion, Matt Watson, host of Product Driven, dives into the nuances of achieving true product-market fit. He explains why metrics like demo to close are critical indicators. Discover why the Sean Ellis test surpasses NPS in gauging market resonance. Matt emphasizes retention as the best long-term metric, though it can take time. He also shares insights on recognizing when to pivot or persist, highlighting the importance of asking the right questions to customers for authentic feedback.

Edo Liberty, founder of Pinecone and former AWS AI services leader, shares his entrepreneurial journey filled with challenges. He faced 40 rejections from VCs while launching his innovative vector database startup. However, a strategic pitch pivot enabled him to secure a $10M seed round, transforming Pinecone into a vital resource for AI applications when ChatGPT hit the scene. Liberty emphasizes the importance of market timing and practical solutions, providing invaluable insights for early-stage founders navigating the startup landscape.

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.Keywordsentrepreneurship, 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, challengesTimestamps(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 AdviceSend me a message to let me know what you think!

Dmitry Gurski, founder of Flo Health, shares his extraordinary journey from picking mushrooms in Belarus to leading a billion-dollar health app with 75 million users. He reveals how simplicity in product design outperformed rivals and emphasizes that user retention is key for success. Dmitry discusses the brutal fundraising process, facing over 200 rejections, and the importance of team dynamics for startups. Learn why targeting a broad audience and embracing failure can lead to lasting impact in the competitive health app market.

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:How to use new social media channels to drive growth.How to leverage partnerships to get end user adoption.Why having a profitable agency can be a great way to get started.Why capital efficiency can be a huge edge.Rebranding can help clarify market positioning.What it feels like to make $10s of millions in one day.KeywordsPerkBox, 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 learnedTimestamps(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 AdviceSend me a message to let me know what you think!

Noah Glass, founder of Olo, a leader in restaurant technology, shares the fascinating journey from launching a pre-order app in 2005 to leading a $1B public company. He discusses the challenges of raising funds during the financial crisis and the strategic pivot from a marketplace to a B2B SaaS model. Noah reveals how early guerrilla marketing and a pivotal partnership with La Colombe propelled Olo into the spotlight. He emphasizes perseverance, adaptability, and embracing adversity as keys to success in the competitive tech landscape.

Frankie Le Nguyen, founder of Staging Labs, shares his journey into the startup world after losing $10K to a crypto scam. He delves into how personal experiences can fuel innovation and the pitfalls of following Lean Startup principles too rigidly. Frankie recounts the struggles of validating market needs amid shifting crypto sentiments, the challenges of partnerships, and the emotional toll of product failure. With insights on customer alignment and navigating the world of scams, his story is a compelling mix of ambition and hard lessons learned.

Hussein Fazal, co-founder of Super.com, shares his inspiring journey from a travel startup to fintech success. After facing the harsh impacts of COVID-19, he pivoted from SnapTravel to create a unique hybrid debit-credit card. He emphasizes the importance of understanding customer needs and finding an unfair advantage. With lessons on resilience, he reveals how testing ideas through smoke tests helped him navigate rejection from VCs. Just three years later, Super.com is thriving at $150M in ARR, proving that rapid adaptation can lead to incredible growth.

Jeffrey Wang, Co-founder of Amplitude, shares his journey in analytics, turning a startup into a $1.5B public company. He reveals how Amplitude outsmarted competitors like Mixpanel by offering superior features at a fraction of the cost. Wang discusses the struggles of securing initial funding and the critical pivot from voice recognition to user insights. He emphasizes storytelling as a tool for attracting investors and the significance of maintaining control and high standards in building a successful company.