Never Change Who You Are | Jason Friedman and Drew Feldman on Why Authenticity Wins

In this episode of Just Press Record, Matt brings together two people who have never met before and lets the conversation unfold in real time.

Jason Friedman and Drew Feldman come from very different professional paths, but quickly discover shared experiences around career risk, entrepreneurship, creativity, and the emotional reality of building something from scratch.

What starts as a conversation about work becomes a deeper discussion about identity, trust, burnout, and what it really takes to navigate uncertainty while staying true to yourself.

Topics covered in this episode

• Leaving stable careers to pursue uncertain but meaningful paths
• The emotional and psychological reality of quitting a job and starting over
• How creative backgrounds shape entrepreneurship and decision making
• Why trust, integrity, and reputation matter more than credentials
• The role of storytelling in building relationships with clients and audiences
• Balancing ambition, work ethic, and personal boundaries
• Burnout, constant connectivity, and the challenge of truly turning off
• Why human judgment and empathy still matter in an AI-driven world
• Building trust through shared values, not sales tactics

Timestamps

00:00 Why these two needed to meet and the idea behind Just Press Record
01:00 Quitting a job and the panic that comes with taking the leap
06:00 From acting and filmmaking to finance and advising
10:45 Career pivots, risk tolerance, and variable income
15:00 The emotional cost of entrepreneurship and Sunday anxiety
19:30 Creative work, grinding, and redefining success
25:00 Burnout, boundaries, and the struggle to turn off
29:00 Shabbat, forced downtime, and digital detox
35:00 Building a company, momentum, and long-term trust
38:00 AI, advisors, and why human relationships still matter
45:00 Trust, integrity, and why reputation compounds over time