Advising Startups: Asking the Right Questions

Blake Squires began his journey in the mid-90s in Los Angeles, capitalizing early on the convergence of technology and media. He soon returned to his hometown of Cleveland to co-found Everstream with Steve McHale (episode 196) and Charlie Lougheed (episode 42, and also my co-founder at Axuall). Blake served as COO until Everstream’s acquisition by Concurrent Computer Corp in 2005.

Next, he co-founded Findaway, a global leader in digital audiobook distribution and creators of PLAYAWAY, a line of preloaded audiobook devices and products. Findaway was acquired by Spotify in 2022—a story shared by co-founder Mitch Kroll (episode 128) and early team member Mike Belsito (episode 52).

In 2011, Blake launched Movable, a software and wearable platform built to "inspire movement." He also founded DoctorsOrders, an e-scripting tool for medical suppliers, which was acquired by Cardinal Health in 2018.

Blake later partnered with inventor John Osher (of SpinBrush fame) to develop the Stubl/Shadow manual razor, acquired by Edgewell for its Schick brand. The duo also created a unique toothbrush licensed to Waken in the UK.

In 2022, Blake co-founded Bloomfilter, an AI-powered process intelligence platform optimizing the product and software development lifecycle. We’ve heard Bloomfilter’s story from his co-founder Andrew Wolfe on episode 134.

By 2024, Blake had become a board partner at Greycroft and a “Fellow” at global design firm IDEO, recognized for his work supporting VCs and early-stage startups. Blake also serves as a founding advisor to the Ohio Angel Collective.

As I mentioned up top, Blake’s story truly is a Lay of The Land of Lay of The Land. He’s deeply connected with Northeast Ohio’s startup ecosystem—through this episode alone, we’ll hear links to Lee Zapis (episode 7), John Knific (episode 199), David Levine (episode 132), AC Evans (episode 39), Ray Leach (episode 69), and many more.

More than just well-connected, Blake is a visionary builder, inspiring leader, and accomplished serial entrepreneur with a rare ability to scale products, teams, and brands.

00:00:00 - The Entrepreneurial Journey Begins  
00:12:17 - Passion and the Intersection of Art and Business  
00:15:09 - Defining Core Values in Entrepreneurship  
00:18:27 - The Evolution of Big Mama Music  
00:21:09 - Navigating Course Corrections in Business  
00:23:23 - Finding the Next Problem to Solve  
00:26:25 - Building a Values-Driven Company  
00:28:09 - The Shift to Audiobooks and Market Insights  
00:33:35 - The Role of Storytelling in Business  
00:41:23 - Learning from Failure and Pivoting Strategies  
00:43:22 - Scaling and Growth in Libraries  
00:48:47 - Building a Strong Company Culture  
00:49:08 - Lessons from Movable and the Importance of Partnerships  
00:54:55 - Navigating the Healthcare Market  
00:55:42 - Universal Truths in Entrepreneurship  
01:01:07 - Transitioning to Advisory Roles and New Ventures  
01:04:20 - Hidden Gem 

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LINKS:
https://www.linkedin.com/in/blakesquires/

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SPONSOR:

Roundstone Insurance

Roundstone Insurance is proud to sponsor Lay of The Land. Founder and CEO, Michael Schroeder, has committed full-year support for the podcast, recognizing its alignment with the company’s passion for entrepreneurship, innovation, and community leadership.

Headquartered in Rocky River, Ohio, Roundstone was founded in 2005 with a vision to deliver better healthcare outcomes at a more affordable cost. To bring that vision to life, the company pioneered the group medical captive model — a self-funded health insurance solution that provides small and mid-sized businesses with greater control and significant savings.

Over the past two decades, Roundstone has grown rapidly, creating nearly 200 jobs in Northeast Ohio. The company works closely with employers and benefits advisors to navigate the complexities of commercial health insurance and build custom plans that prioritize employee well-being over shareholder returns. By focusing on aligned incentives and better health outcomes, Roundstone is helping businesses save thousands in Per Employee Per Year healthcare costs.

Roundstone Insurance — Built for entrepreneurs. Backed by innovation. Committed to Cleveland.

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Past guests include Justin Bibb (Mayor of Cleveland), Pat Conway (Great Lakes Brewing), Steve Potash (OverDrive), Umberto P. Fedeli (The Fedeli Group), Lila Mills (Signal Cleveland), Stewart Kohl (The Riverside Company), Mitch Kroll (Findaway — Acquired by Spotify), and over 200 other Cleveland Entrepreneurs.

Connect with Jeffrey Stern on LinkedIn — https://www.linkedin.com/in/jeffreypstern/

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