Episodes

15 total
May 9, 2023Intro to Startup anti-pattern SeriesAn anti-pattern is a commonly used process, structure, or pattern of action that, despite initially appearing to be an appropriate and effective response to a problem, has more bad consequences than good ones. Simeon Simeonov first wrote an introduction to the value of startup anti-patterns back in 2013. To sum it up, it’s hard to […]04:30May 9, 2023Startup anti-pattern #1: elephant huntingFirst, two stories that highlight two different sides of elephant hunting. In 2005, Meridio was guaranteed to win a deal worth $15m+. Meridio was a small electronic documents and records management (EDRM) startup whose software ran inside some of the world’s most secure organizations: from banks to oil & gas companies to branches of government […]12:34Aug 13, 2025Startup anti-pattern #2: IgnoranceListening to a startup pitch a few weeks ago I had to exercise effort not to shake my head in disbelief. The presenters were describing the products and business model of an established company I was very familiar with and doing it with what seemed to be blatant disregard of reality. They forgot to mention […]06:54Aug 13, 2025Startup anti-pattern #3: platform riskOne of the fastest ways for a startup to grow has always been to ride on the shoulders of a successful platform: from Microsoft/OSS in software to AWS in cloud computing to iOS/Android in mobile to Facebook/Twitter/Pinterest in social to IAB/Google in advertising and the many SaaS players. Betting on a platform focuses product development […]15:10Sep 26, 2023Startup anti-pattern #4: if you build it, they will comeAs part of the continued series on startup anti-patterns, we look at the battle between conviction and validation. First, a story. In 2000, Intech technology, a fledgling startup out of Israel, was building a new type of billing software for property managers. Intech had one potential customer- the Israeli government – that shared the founders’ […]15:04Nov 8, 2024Startup anti-pattern #5: Bad RevenueFirst, a blast from the past which some of us might remember. As a kid growing up in the 80s, I was a movie junkie and rented movies from Blockbuster several times a week. I’d binge-watch the movies I loved (I’ve probably seen the entire James Bond series 20 times). Back in the 80s, Blockbuster […]10:43Jan 31, 2025Startup Anti-Pattern #6: Chasing the CompetitionFirst, a story. In 2012, Twitter launched Vine, a platform that allowed users to create and share six-second looping videos. Vine quickly gained popularity, becoming a cultural phenomenon and amassing a substantial user base. At its peak in December 2015, Vine had over 200 million active users(!). However, as competitors like Instagram and Snapchat introduced […]08:02Feb 10, 2025Startup Anti-Pattern #7: Chasing “Blue Oceans”As part of the continued series on startup anti-patterns, we look at the perilous pursuit of endless new unknown markets: “Chasing Blue Oceans.” What It Is “Chasing Blue Oceans” is the anti-pattern where startups repeatedly seek untapped markets that lack competition but also lack the necessary customer demand or market size to sustain a venture-scale […]08:31Feb 10, 2025Startup Anti-Pattern #8: Analysis ParalysisAs part of the continued series on startup anti-patterns, we look at the crippling effect of overanalyzing decisions: “Analysis Paralysis.” First, a story. In 2014, a promising IOT startup in my portfolio (which I won’t name) was working on a revolutionary home security product. The product was cutting edge from an AI standpoint. The founders […]08:05Mar 16, 2025Startup Anti-Pattern #9: (Founder) ArroganceIn the early days of Apple, Steve Jobs was famously arrogant. He believed he knew what users wanted before they even realized it themselves. His confidence led to groundbreaking products like the Mac and the iPhone, but it also resulted in some significant missteps—like the overly expensive Lisa computer and the rigid, closed system of […]09:43Mar 16, 2025Startup anti-pattern #10: Boiling the OceanFirst, a Story, or two In the early 2010s, Magic Leap captivated the tech world with its ambitious vision for augmented reality. Backed by billions in funding from companies like Google and Alibaba, it promised a revolutionary AR headset that would change the way people interacted with digital content. The problem? Magic Leap wasn’t just […]10:42Jul 2, 2025Startup Anti-Pattern #11: Bridge to NowhereAs part of the continued series on startup anti-patterns, we examine the dangerous territory of bridge rounds that lead nowhere: “Bridge to Nowhere.” First, a Story In 2018, I came across a promising fintech startup that had raised a solid Series A but was burning through cash faster than expected while pursuing an ambitious expansion […]12:21Jul 2, 2025Startup Anti-Pattern #12: Design by CommitteeAs part of the continued series on startup anti-patterns, we examine the productivity-killing practice of collective decision-making: “Design by Committee.” First, a Story In 2014-2015, my team at Life360 struck a strategic partnership with ADT, the #1 home security company. They invested $50m in our company, we agreed to strategically launch a co-branded version of […]11:21Aug 21, 2026Startup Anti-Pattern #13: Confirmation BiasIn 2011, the founders of Color Labs raised $41 million before launching their product—a proximity-based photo-sharing app. The team, stacked with experienced tech executives, was convinced they’d cracked the code on mobile social networking. They had data from user studies that “confirmed” people wanted to share photos with nearby strangers. They had advisory board members […]06:11Aug 21, 2026Startup Anti-Pattern #14: Bleeding on the EdgeIn 2013, a startup called Leap Motion shipped a gesture-control device that let users interact with their computers through hand movements in the air. The technology was genuinely impressive—based on breakthrough infrared sensor technology that could track finger movements with sub-millimeter accuracy. Leap Motion raised over $44 million and generated enormous buzz. The problem wasn’t […]06:22