Juxtapositions

Is AI in healthcare actually underhyped? Healthcare investing legend Annie Lamont, Co-Founder and Managing Partner of Oak HC/FT, makes a strong case in the latest episode of our podcast conversation series, Juxtapositions.
 
In this episode, Juxtapose Co-Founder and Managing Partner Jed Cairo and Partner Ben West sit down with Annie to talk about her career backing breakout companies like Athenahealth, Devoted Health, and VillageMD across her nearly three decades at Oak Investment Partners and 12 years building Oak HC/FT into a leading firm managing over $7B across a 100+ company portfolio.
Their conversation dives into:
Why Annie believes AI is actually underhyped, not overhyped, in healthcare
The shift from horizontal to vertical software strategies and what makes a business truly defensible
What separates a 10x entrepreneur from one who just got lucky
How to be an effective board member 
Her boldest bet on how healthcare gets rebuilt over the next decade... and more!

For our third installment of the Juxtapositions podcast, Juxtapose's Co-Managing Partner Jed Cairo hosted a conversation with Scott Wagner, Co-Board Chair of GoodRx and former CEO of GoDaddy, and Andrew Low Ah Kee, Fanatics Commerce CEO and former GoDaddy COO. Jed met Scott and Andrew when they were all working at KKR many years ago, and this reunion of old friends spans the investor to operator journey, managing leadership teams through hyper-scale and challenge, what makes an effective Board, and everyone's boldest decisions and greatest risks.

At Juxtapose, we spend our days building companies with experienced executives and founders — people who’ve already led teams, scaled products, and seen a few cycles. That means our conversations often go deeper than the typical startup story. They’re about career arcs, reinvention, and the mindset it takes to lead through change.
 
So, we decided to start recording them. Introducing Juxtapositions, a series of conversations hosted by Juxtapose. In each episode, a leader from our Concept Development, User Research & Design, or Talent team will sit down with business and technology leaders — from operators to investors, founders to execs — and come away with hard-earned wisdom. From generational market shifts, to career pivots, to company transformations, each conversation dives into how our guests navigated change, what they learned, and how those lessons might help you think differently about your own path.
 
This episode features Andrew Rubin, the Founder and CEO of Illumio, where he guides strategy and partners with some of the world’s most influential organizations—including Citi, HSBC, Salesforce, and Microsoft—on Zero Trust and next-generation cybersecurity. A seven-time Goldman Sachs “100 Most Intriguing Entrepreneur” and Ernst & Young Bay Area Entrepreneur of the Year, Andrew also serves on the Board of Emigrant Bank and actively backs emerging technology companies as an advisor and angel investor.

At Juxtapose, we spend our days building companies with experienced executives and founders — people who’ve already led teams, scaled products, and seen a few cycles. That means our conversations often go deeper than the typical startup story. They’re about career arcs, reinvention, and the mindset it takes to lead through change.
 
So, we decided to start recording them. Introducing Juxtapositions, a series of conversations hosted by Juxtapose. In each episode, a leader from our Concept Development, User Research & Design, or Talent team will sit down with business and technology leaders — from operators to investors, founders to execs — and come away with hard-earned wisdom. From generational market shifts, to career pivots, to company transformations, each conversation dives into how our guests navigated change, what they learned, and how those lessons might help you think differently about your own path.
 
The first conversation is between Steve Herrod, Juxtapose Partner, board member, and former CTO of VMware and Julia Austin, a serial operator, executive coach, educator, board member, author, and former CTO who has led both startups and large organizations through massive evolutions. Steve and Julia worked together at VMWare when she was Vice President of Innovation, and since then she's gone on to be the CTO of Digital Ocean, joined several startup boards, and was on the faculty of Harvard Business School as a Senior Lecturer for over a decade, and now serves as an Executive Fellow. She recently published a book, After the Idea, about creating and scaling startups.