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Pioneer Square Labs

Software Development

Facts

HQ
Seattle
Sectors
Software Development
Founded
2015
Employees
33

Don’t Sleep on Seattle Startups | Vivek Ladsariya (Managing Director, Pioneer Square Labs)

This week on The Data Minute, Peter sits down with Vivek Ladsariya, Managing Director at Pioneer Square Labs, for a deep dive into the Seattle startup ecosystem and the evolving world of venture studios. Vivek breaks down why Seattle has become the quiet giant of AI infrastructure, holding the second-highest concentration of AI talent in the US, and explains why the "locked up" talent at Amazon and Microsoft is finally breaking free. He also gives a candid assessment of the venture studio model, why many studios are "zombies," how AI is forcing them to pivot to a holding company structure…

The Agentic Entrepreneur: How the next wave of AI is changing the startup playbook

This week on the GeekWire Podcast: How artificial intelligence is changing the way companies are created, built, and operated. We're on location at Pioneer Square Labs in Seattle with investor and entrepreneur T.A. McCann, a managing director at the startup studio and venture capital firm. He explains how AI agents are automating complex functions, letting small teams do the work that once required large groups of people. As AI makes product development easier, he says, the key strategic moat for many startups is now shifting to distribution and data. Other topics include: The wearable AI recorder that captures everything he…

Navigating the Enterprise Compliance Journey with Certivo CEO Kunal Chopra

In this episode of the Shift AI Podcast, Boaz Ashkenazy welcomes Kunal Chopra, CEO and Founder of Certivo, to explore how AI agents are evolving from assistants to true team members. Kunal shares insights from his experience as a former leader at Microsoft and Amazon, and his current venture tackling product compliance challenges for manufacturers. Through Certivo's AI agent compliance managers can automate tedious regulatory tasks while maintaining strategic control of the process. The conversation delves into the distinction between AI assistants and agents, examining the collaborative dance between humans and AI that defines today's implementations. Kunal offers a compelling…

The founding of Rover and the business model behind Pioneer Square Labs, a conversation with Greg Gottesman

Send us Fan Mail In 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 three initial Managing Directors of Madrona…

T.A. McCann

In this episode of the What Fuels You Podcast, Shauna talks with T.A. McCann, managing director at Pioneer Square Labs, a startup studio and venture capital firm. They discuss T.A.'s background in sailing, winning the America’s Cup, swimming, his successful career in startups, and his tips for staying healthy and productive. This episode covers topics such as entrepreneurship, validation of startup ideas, time management, and health and human performance. See omnystudio.com/listener for privacy information.

How AI's new era is inspiring one startup founder

This podcast features Kirill Zubovsky, a startup founder and consultant, who is now working with AI to create applications. He talks about his journey over the past few months with AI, his experience with generative AI and GPT-3, and the application of AI he has been working on, Smartynames, a domain and business name finder. He also talks about his experience living in a van with his two kids and two pets and his thoughts on the current "App Store moment" for artificial intelligence. (This summary was produced by SwellAI.com based on its AI analysis of the content in this…

A Conversation with Julie Sandler | Managing Director @ Pioneer Square Labs | Partner @ PSL Ventures | Madrona Venture Group | Seattle Entrepreneurial Women’s Network | Amazon | Stanford U. | Harvard Business School

In this episode, we talk to Julie Sandler about her psychology background and how that has translated to her work today, especially her relationships with founders. Talking about PSL, she touches on the growth of the fund and the Northwestern region and the venture studio model. She also dives into diversity both within the fund and their investments, serving as a testament to advancements in the industry. She concludes with her observation that the support system among women prominent in VC provides guidelines to help navigate the space.

WestRiver Group

This week on Finding PROOF, our hosts Jennifer Schretter and Thanasis Delistathis sit down with Anthony Bontrager, Managing Director at WestRiver Group, a firm that invests in seed and early-stage companies in the US Pacific Northwest.

How SPACs are shaking up Seattle's startup scene

An online marketplace that helps to facilitate trade between marijuana sellers and buyers will soon see its own stock traded on the Nasdaq. Another that connects pet owners with walkers, boarders and other caregivers just posted its first earnings as a publicly traded company. And a 3-year-old Redmond-based biotech company with a mere 25 employees just raised $80 million its stock market debut. SPACs are shaking up Seattle's startup scene. On this episode of the GeekWire Podcast, we examine how special purpose acquisition companies are turning startups into publicly traded stocks at a rapid clip. The SPAC phenomenon is giving…

Ben Gilbert of PSL and 'Acquired' on the red-hot market for IPOs, VC and acquisitions

Another day, another deal. Keeping up with the flurry of acquisitions, IPOs, SPACs and venture capital these days is no easy task. In fact, IPO dollar volume for 2021 has already reached $171 billion, surpassing the record totals of last year. Same goes for mergers and acquisitions, with record levels of deal activity tracked for 2021. The money is certainly flowing. Washington state now boasts 11 "unicorns" — privately held companies boasting valuations of $1 billion or more. Many of them — such as Highspot, Zenoti and Outreach — have raised venture capital rounds of $150 million or more in…

Pioneer Square Labs

This 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.

The Future of Femtech

This week we're presenting a new episode of the GeekWire podcast 2025: Tomorrow, Today featuring a discussion with Julie Sandler of Pioneer Square Labs. It's one in a series of conversations with technology investors on the 2025 podcast. Find more episodes at geekwire.com/2025podcast. We'll be back next week with our regular weekly show. See omnystudio.com/listener for privacy information.

GeekWire at 10 years: Reflections on an extraordinary decade in Seattle tech

This Sunday, March 7, will mark 10 years since GeekWire’s launch. Looking back, we couldn’t have picked a better decade as GeekWire’s first, given our focus on Seattle and Pacific Northwest innovation. This was the moment that Seattle tech came into its own. We’ve covered the rise of the cloud, Amazon’s boom, Microsoft’s rebirth, the arrival of Silicon Valley engineering centers, disputes, mergers, IPOs, and the emergence of thousands of startups. And in the past year, we’ve covered Seattle as a center of the scientific and philanthropic response to a world-changing pandemic. What happens here matters everywhere. This has become…

Julie Sandler

Julie is a managing director at Pioneer Square Labs, and runs the firm's venture capital arm, PSL Ventures. Prior to PSL, Julie was a partner at Madrona Venture Group, where she led the firm’s investments in Integris, Poppy, and Julep. In 2013, Julie launched the Seattle Entrepreneurial Women’s Network, an informal forum for women entrepreneurs and startup executives to connect in the Greater Seattle area. She currently resides in Seattle with her husband, Alejandro, and their toddler son and newborn daughter. See omnystudio.com/listener for privacy information.

Leading a startup through the crisis

For startup leaders accustomed to building their businesses in boom times, the economic impact from the COVID-19 pandemic goes beyond mere setback, into the realm of complete shock. But even in these unprecedented times, there are lessons to be learned from past downturns, and from the steps other startups are taking to navigate the current crisis. "We have a whole generation of people who never went through anything that looked like a dislocation or a downturn," says Dan Rosen, chair of the Alliance of Angels, an investor, biophysicist and veteran tech executive who has been through multiple economic cycles. "This…

Ben Gilbert

Ben Gilbert’s had the entrepreneurial bug since he was young, starting with building his high school website and developing apps in his college dorm room. Since then, Ben has worked at several incredible startups, become Co-founder of Pioneer Square Labs, Co-host for popular venture capital podcast, Acquired, and was named Young Entrepreneur of the Year in 2017. Ben attributes much of his success to always “having two careers at once” by working on side projects and being fueled by a sense of accomplishment. In this episode, Ben talks about his first app, SeizeTheDay, that was downloaded over a million times…

Xiao Wang

Xiao Wang talks about his own family’s process of immigrating to the United States from China and how it influenced him to start his company, Boundless Immigration. Before Boundless, Xiao received degrees from both Stanford and Harvard Universities and worked for McKinsey, the New York City Department of Education, and Amazon. With the help of Pioneer Square Labs, Xiao decided to leave the corporate world and cofound his company in 2017. Xiao discusses what his parents went through during their immigration process, his plans for what he wants to achieve with Boundless in the future, and how he’s extremely proud…

Secret Startup Ingredient: Microsoft

Would you have guessed that nearly 25 percent of the Seattle region's top tech startups are led by CEOs with backgrounds at Microsoft? That was the surprising result of our analysis of the GeekWire 200, our index of the top privately held tech companies in the Pacific Northwest. And fundings for the region's startups bucked the national trend, as reflected in data from our new startup deal tracker. Nintendo unveiled a new iteration of its Switch game console; former Microsoft CEO Steve Ballmer pulled off what might be his greatest deal ever; and an Amazon employee showed the potential of…

IPOs without profits

What do Pinterest, Lyft, Uber and Slack have in common? Yes, they're all newly public or about to make their initial public offerings. But they also share a common characteristic on the bottom line -- proceeding with their IPOs with lots of revenue and growth but, so far at least, without the consistent profits to show for it. And they're part of a trend. Eighty-three percent of IPOs in the first three quarters of 2018 were made by companies that hadn't posted profits in the prior 12 months. So what's the future of these companies? On this episode of the…

Greg 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…

Never Stop Being Curious | Greg Gottesman

We're kicking off 2019 Creator Institute podcast with a longtime friend of mine Greg Gottesman - a managing director and co-founder of Pioneer Square Labs. Prior to PSL, Greg served as one of the three initial Managing Directors of Madrona Ventures Group, where he worked for almost 20 years. Check it out! #EricKoester #CreatorInstitute #Podcast FOLLOW ERIC KOESTER FACEBOOK: http://bit.ly/2ONpDSk LINKEDIN: http://bit.ly/2BurtG1 INSTAGRAM: http://bit.ly/2PrQhBk TWITTER: http://bit.ly/2OT77In FOLLOW CREATOR INSTITUTE FACEBOOK: http://bit.ly/2N5upua LINKEDIN: http://bit.ly/2nWGOpk TWITTER: http://bit.ly/2nTNVi7

How a new VC fund is trying to change the game for Seattle entrepreneurs

Flying Fish Venture Partners has a bold plan: completely change the game for entrepreneurs in Seattle. We sit down with Heather Redman, one of the fund's co-founders, to hear her vision for the fund and how she plans to shake up Seattle's startup ecosystem. Follow all our coverage, including more about Pacific Northwest startups, at GeekWire.com Thank you to this week’s sponsors: Wealthsimple — GeekWire listeners pay no management fees for a year when they invest up to $15,000 on Wealthsimple’s automated investing platform. GoDaddy — who is offering GeekWire listeners 35 percent off their purchase of a GoDaddy domain…

  • Geoff Entress
    Geoff Entress Founder, Co-founder and Venture Partner
  • Greg Gottesman
    Greg Gottesman Founder, Managing Director, Co-Founder
  • Julie Sandler
    Julie Sandler Founder, Co-founder & General Partner, PSL Ventures, Former Managing Director , Venture Partner (upcoming), Venture Partner, Managing Director, PSL

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