CEO Spotlight

CEO Spotlight: The Life of Entrepreneur, Investor, and Philanthropist, Jake Medwell

Jake Medwell

Jake Medwell has a track record of scaling companies to success. Often acting as both an entrepreneur and investor, he has been involved with some of the leading companies coming out of Silicon Valley the last decade.  He has taken a deep focus in the logistics and supply chain technology has become where he was named the most active investor in the space in 2020 by pitchbook.

Getting a Start at USC

In 2007, Jake Medwell pursued his interest in entrepreneurship by enrolling at the University of Southern California. As a leading student in their Marshall School of Business program, he worked toward earning his Bachelor of Arts in Business and Entrepreneurship while simultaneously lecturing in the MBA program as an undergraduate.

Before his graduation in 2011, he had founded both Kairos and Solé Bicycle Co which he is still involved with to this day.

Jake continues to stay heavily involved at USC where he frequently lectures on technology and entrepreneurship. He has also endowed the Athena Entrepreneurship Award given out yearly by the university.

Founding Companies

Kicking off Sole Bicycle Co. was just a start from Jake Medwell.  He has helped launch and build successful companies, including:


Jake Medwell helped found Kairos in 2009 before joining its board of directors where he still plays an important advisory role. Through this venture, he helps many young entrepreneurs connect with leaders in their target industries plus gain key insights from international mentors who come from all walks of life. Kairos now operates a series of investment funds and a build program focused on launching 2-3 companies per year focused on fixing societies key issues.


In 2012, Medwell co-founded Humin, a revolutionary company built to improve connections by aggregating and contextualizing data. Their platform promised to change how people store and view their contacts, effectively altering the way they interact with their phones. The company was acquired by IAC in 2016.


In 2015, Medwell co-founded 8VC,  one of the top performing private investment funds with over 5 billion of committed capital. 8VC has a deep focus on enterprise software, logistics, biotechnology, and healthcare. In 2020 Jake was named the most active logistics technology investor by PitchBook.


Medwell served as an advisor to Allbirds starting in 2016.


In 2018, Jake Medwell helped co-found Baton out of 8VC. Baton is a technology platform that eliminates detention and dwell time for truck drivers. Long haul trucks drop off and pick up loads at our network of drop zones and Baton handles pick up and delivery to and from warehouses. Baton most recently raised a large financing round from Maersk, Prologis, and Ryder.

Operation Masks [Non-Profit]

Working alongside his business partner, Drew Oetting, Jake Medwell launched Operation Masks to help medical workers get vital PPE for their fight against the COVID-19 pandemic. Through their non-profit, they were able to source PPE for many key health centers across the nation, including Cedars Sinai, Beaumont, and Henry Ford Health Systems.

Jake Medwell and Drew Oetting were key players in providing hundreds of millions worth of PPE to groups in need.

Lineage Logistics

Jake Medwell joined the advisory board of Lineage Logistics in  2021 to help them continue to lead the industry in technology and data science.

Promoting Freight Tech Growth

In his role at 8VC, Medwell is also helping many freight tech startups get a solid start in the industry. Through those efforts, he’s effectively revolutionizing the industry by changing the way things have been done for the last century. As transportation and logistics companies adopt the emerging freight tech platforms, they greatly improve their operations and experience tremendous growth.

The freight tech companies that 8VC is involved is so far include:

  • Platform Science
  • Trackonomy
  • The Boring Company
  • KeepTruckin
  • Project44
  • Joby Aviation
  • Flexport
  • Deliverr
  • Baton
  • Beacon
  • Outrider
  • DASH Systems
  • HDVI
  • Vector
  • TUL

Going into the Future with a Founder-First Mentality

One of the key reasons for Medwell’s success in the freight tech industry links back to his founder-first mentality. Instead of supporting tech innovators as a whole, he zeros in on industry experts interested in changing the current approach to logistics and transportation.

Through the expert’s in-depth understanding of the field, they are better able to develop key changes that are impactful for the sector. Then, once they partner with key players in the tech field, they can collaborate to create winning platforms that companies are happy to try out and integrate into their operations.

With that move, Jake Medwell helps change the trajectory of both freight tech startups and longstanding logistics and transportation companies. His impact on these fields reverberates across the industry as a result, showcasing his expertise in building companies from the ground up and scaling them into huge enterprises.

Sophie Ireland
SVP for News and Editorial Director. As CEOWORLD magazine's senior vice president for news and editorial director, Sophie Ireland oversees CEOWORLD magazine's journalism and journalists around the world and across platforms. She leads an award-winning team of journalists and newsroom executives who are committed to excellence, innovation and the highest quality reporting and storytelling. Follow her on Twitter, Facebook, Instagram, or connect on LinkedIn. Email her at