Shows
AI First with Adam and AndyBuilding Is Easy Now: Why Distribution Is the Real AI Startup BottleneckIn this episode of AI First with Adam and Andy, Greg Gottesman of Pioneer Square Labs shares hard-earned lessons from nearly three decades as a venture capitalist, founder, and startup studio operator. Greg explains why startups rarely fail due to product or technology challenges, even in today’s AI-driven landscape, and why cost-effective distribution remains the defining constraint for success.The conversation explores how AI has dramatically lowered the cost and speed of building products, intensifying competition while making customer acquisition harder than ever. Greg also offers a clear framework for understanding AI-native companies, contrasting isolated AI te...
2026-01-1431 min
From Startup to ExitBest of 2024: From Startup to ExitSend us a text2024 has been an incredible year for TiE Seattle’s From Startup to Exit podcast – featuring inspiring conversations with entrepreneurial leaders, innovators, and changemakers. As the year ends, we’re excited to share the Top 4 Episodes of 2024 that you don’t want to miss!The Founding of OfferUp - Nick Huzar: https://www.buzzsprout.com/2234096/episodes/13413716The Founding of Rover & the Vision Behind Pioneer Square Labs - Greg Gottesman: https://www.buzzsprout.com/2234096/episodes/13615903Mega-Successful Exits: Chronus & Ally.io - Vetri Vellore: https://www.buzzsprout.com/2234096/episodes/13899931Deve...
2024-12-291h 04
North Star LeadersStorytelling in Startups with Greg GottesmanWhat’s the secret to pitching a compelling business idea? In this episode of North Star Leaders, Lindsay Pedersen talks with Greg Gottesman, co-founder of Pioneer Square Labs (PSL), about the art of storytelling in startups, using AI to scale businesses, and the journey of transforming ideas into thriving companies. They also explore Greg's transition from venture capital to the startup world, sharing insights on building companies and the transformative role of AI in business.
Storytelling as Strategy: Greg emphasizes the importance of a clear, engaging narrative to captivate investors, customers, and team members from th...
2024-11-1229 min
The Custom Made PodcastFinding Your Niche: Crafting Your Path to PurposeIn this episode, Writer/Podcaster/Creative, Matt Gottesman, sheds light on the importance of self-discovery and following your passions to find your niche. He offers practical advice on using practices like morning pages and meditation to gain clarity to find your niche and emphasizes the importance of consistent creation in building confidence. This episode is packed with valuable insights for anyone seeking to break free from the mold and pursue their passions. Tune in to learn how to find your niche, unleash your inner creator, tap into your spirituality and build a fulfilling life!
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2024-03-2639 minFrom Startup to ExitThe founding of Rover and the business model behind Pioneer Square Labs, a conversation with Greg GottesmanSend us a textIn 2011, Greg Gottesman had a bad experience leaving his dog for the weekend at a local Kennel. That experience led him to pitch the idea for Rover at a Startup Weekend which he won. That led to the formation of Rover and the rest is history.In our second podcast episode, Gowri Shankar and I explore the foundation of Rover as well as the business model behind Pioneer Square Labs.Greg Gottesman is a Managing Director and Co-Founder of PSL. Prior to PSL, Greg served as one of the...
2023-09-1956 min
The PromptYou Are The Niche. Don’t Niche Down, Niche Up with Matt GottesmanIn this episode, we talk about: How to show up as yourself in your business, while taking care of your spiritual, physical, and mental health. Resources + Links: Check out these books - The Almanac of Naval Ravikant https://www.amazon.com/Almanack-Naval-Ravikant-Wealth-Happiness-ebook/dp/B08FF8MTM6 Essentialism: The Disciplined Pursuit of Less https://www.amazon.com/Essentialism-Disciplined-Pursuit-Greg-McKeown/dp/0804137382 Connect with Matt Instagram @mattgottesman Podcast The Niche is You Website https...
2023-02-0751 min
Climate Mayhem - Presented By The Daily Marketer#76: How do you build a marketplace startup from SCRATCH? Rover Co-founder, Bestselling Author, and TED Speaker, Greg Gottesman, Gives the Formula (Part 2)Greg Gottesman is the co-founder and managing director of Pioneer Square Labs, former managing director at Madrona Venture Group, and is a co-founder of Rover (ROVR), the biggest pet sitting marketplace in the nation. Greg has spent his entire life authoring his journey. At 22 he published a book that became the survival manifesto for the 1980's college student (7 editions), at 24 he became a lawyer which he soon left so he could start working in business, and has been n investor in venture capital ever since. Greg has plenty of noteworthy accomplishments too long for this...
2022-01-0638 min
Climate Mayhem - Presented By The Daily Marketer#75: Co-founder and Managing Director of Pioneer Square Labs, Greg Gottesman, on Obsessing over Marketplace Dynamics and Killing Great Ideas (Part 1)Greg Gottesman is the co-founder and managing director of Pioneer Square Labs, former managing director at Madrona Venture Group, and is a co-founder of Rover (ROVR), the biggest pet sitting marketplace in the nation. Greg has spent his entire life authoring his journey. At 22 he published a book that became the survival manifesto for the 1980's college student (7 editions), at 24 he became a lawyer which he soon left so he could start working in business, and has been n investor in venture capital ever since. Greg has plenty of noteworthy accomplishments too long for this...
2022-01-0438 min
Second ChancesAsher Gottesman's Second ChanceAsher Gottesman is a spiritual entrepreneur, human connection coach and Rabbi in Southern California. Asher was 33 when he lost his multi-million-dollar business, with the resulting bankruptcy destroying what little self-worth he had as a provider to his family – he had hit rock-bottom. Asher found his road to recovery through the rooms of Alcoholics Anonymous. The experience marked the debut of an odyssey of self-discovery, trading ego for vulnerability, and leaving the pursuit of pleasure for the pursuit of meaning. Asher decidedly dedicated the rest of his career to helping others help themselves "restore wholeness" in their lives.
2021-06-2044 min
Finding PROOFPioneer Square LabsThis week our partners chat with Greg Gottesman, Managing Director & Co-Founder at Pioneer Square Labs, a startup studio and venture capital fund based in Seattle, WA.
2021-06-0334 min
Showing Up With Asher GottesmanGreg Baldwin Shows Up For A Good LifeWhile addiction isn't funny, our guest today comedian Greg Baldwin is. He was an incredible story. After going to rehab for cocaine and alcohol at age 19, he went on to play college baseball for four years. However, when he tried meth for the first time, all bets were off. Within five years, he was living in his car and losing his teeth. Then he was arrested and given the choice of rehab or jail. He went to rehab. In this episode, we talk about how meditation has changed him, saving another man's life, how he met previous gue...
2021-05-2542 min
The Eric Koester Creator InstituteThe Startup Weekend | Marc NagerStartup Weekend legitimately changed my life.
Yes, a single weekend did that. (I *did* just happened to do many many of these weekend events because I loved the experience so much). The experience was powerful because of the people and community I met. Startup Weekend let me truly collaborate with people who changed my entire trajectory - Scott Case, Shane Mac, T. A. McCann, Brad Feld, Bo Fishback, Ian Hunter, Greg Gottesman, Steve Case, Mary Grove, Nick Seguin, Adam Hofmann, Franck Nouyrigat and many more.
At the center of the experience was a way to cre...
2019-05-0334 min
What Fuels YouGreg Gottesman Greg Gottesman, a major influencer in the Seattle startup community, sits down and shares his knowledge about entrepreneurship, his passion for the early stage of building companies, and the story behind what sparked the idea for Rover, where Greg is a co-founder. Greg serves as a Managing Director and co-founder of Pioneer Square Labs, both its studio and fund. He was a partner of Madrona Venture Group for 20 years and founder of Madrona Venture Labs. In this episode, he also discusses the entrepreneurship class he teaches at the University of Washington, what he looks for in entrepreneurs’ pitches, and why he...
2019-02-2651 min
What Fuels YouSeason One PreviewThe What Fuels You podcast launches on Tuesday, January 22nd featuring the following guests. Shauna Swerland Greg Gottesman Jane Park Brent Frei Richard Tait Amy Nelson Jonathan Sposato Scott Swerland Fran Dunaway Chad Robins Raja Mukerji Ambika Singh Here’s a teaser of Shauna's conversations from the Season One episodes. Be sure to share, subscribe on iTunes, Google Podcasts or Spotify, and follow us on social media for the latest news and updates!See omnystudio.com/listener for privacy information.
2019-01-1102 min
The Eric Koester Creator InstituteNever Stop Being Curious w/ Greg GottesmanDoes making a choice mean you close the door on the choice you *don't* make?
That fear of making the wrong choice can hold many of us back researchers say -- described as the paradox of choice. But Greg Gottesman offers a perspective that says quite the opposite: making a choice -- and always staying curious regardless of that choice -- can actually open MORE doors than you imagined.
I've had the good fortune to know Greg for the better part of a decade, and yet in our conversation I realized that my personal experiences w...
2019-01-0249 min
The NoviceGreg Gottesman. How one person started a dog-hotel revolution (Rover.com)Family life with three kids, the rising costs of education and where AI and machine learning will take us. Venture Capitalist Greg Gottesman shares business stories, as well as tips on parenting and education. It's a blast! Get full access to The Novice at novice.media/subscribe
2018-07-0252 min
FrankieSense & MorePainted Dogs and Pink Dolphins- Real Endangered Species who NEED US NOW!Host Frankie Picasso had the pleasure of interviewing two incredible Conservationists who have dedicated their lives to saving endangered species, Dr. Greg Rasmussen and Dr. Enzo Aliaga Rossel, on FrankieSense & More!The Painted Dog has roamed the earth for millions of years. They lived throughout Sub-Saharan Africa. Less than 100 years ago, they were about 500,000 strong. Today less than 5000 remain and their very existence is threatened forever.The Pink Dolphin is a fresh water RIVER dolphin living in the Rivers of Bolivia. This amazing mammal is threatened by civilization, the debris from building and se...
2017-06-1557 min
FrankieSense & MorePainted Dogs and Pink Dolphins- Real Endangered Species who NEED US NOW!Host Frankie Picasso had the pleasure of interviewing two incredible Conservationists who have dedicated their lives to saving endangered species, Dr. Greg Rasmussen and Dr. Enzo Aliaga Rossel, on FrankieSense & More!The Painted Dog has roamed the earth for millions of years. They lived throughout Sub-Saharan Africa. Less than 100 years ago, they were about 500,000 strong. Today less than 5000 remain and their very existence is threatened forever.The Pink Dolphin is a fresh water RIVER dolphin living in the Rivers of Bolivia. This amazing mammal is threatened by civilization, the debris from building and se...
2017-06-1557 min
FrankieSense & MorePainted Dogs and Pink Dolphins- Real Endangered Species who NEED US NOW!Host Frankie Picasso had the pleasure of interviewing two incredible Conservationists who have dedicated their lives to saving endangered species, Dr. Greg Rasmussen and Dr. Enzo Aliaga Rossel, on FrankieSense & More!The Painted Dog has roamed the earth for millions of years. They lived throughout Sub-Saharan Africa. Less than 100 years ago, they were about 500,000 strong. Today less than 5000 remain and their very existence is threatened forever.The Pink Dolphin is a fresh water RIVER dolphin living in the Rivers of Bolivia. This amazing mammal is threatened by civilization, the debris from building and sediment th...
2017-06-1557 min
Ask Bill & Dan#16 - iPhone Clip-on Lenses & Flying with BatteriesAfter a long absence, the boys are back with another two great photography questions.First up, Greg wants to do some street photography with this iPhone but feels limited by the focal length and wants to know the skinny on add-on lenses like Olloclip and Moment.Next up, friend of the show Kent is traveling a lot with big lithium-ion battery packs and wants to know what the rules are for bringing them on the airplane as well as best practices to keeping them in tip-top shape.OlloClipMoment Lenses
2016-08-1000 min