Don't Be a Jerk
Episodes
How Brianne Kimmel Built a $45M Fund Around the Founders Nobody Else Believed In
07 Apr 2026
Contributed by Lukas
Brianne Kimmel is the founder and managing partner of Worklife Ventures, a $45M early-stage venture firm backed by Marc Andreessen and Eric Yuan. Her ...
What Happens When an 11-Year-Old Decides to Stop Waiting for Better News and Make It Himself with Sam
24 Mar 2026
Contributed by Lukas
Sam started a podcast because he was tired of feeling helpless.He was consuming the news the way most of us do… headlines that made him anxious, sto...
Why Trust Beats Product: How Avni Barman Built a 60-Million-View Media Empire by Giving Everything Away
17 Mar 2026
Contributed by Lukas
Avni Barman joined Don’t Be a Jerk this week. she already has 1 million people in her community, 60 million monthly views, a 150,000-subscriber news...
Why Nice Leaders Fail with Andrew Dudum, CEO and Founder of Hims & Hers
10 Mar 2026
Contributed by Lukas
Andrew Dudum built Hims & Hers from zero into a multi-billion-dollar consumer publicly-traded consumer health company by doing something most foun...
The Rules of Rule Breaking: David Flink on Why the System Was Never Built for You
03 Mar 2026
Contributed by Lukas
David Flink got kicked out of four schools. Then he went to Brown, then Columbia and spent the next 28 years building systems so that nobody else has ...
The Man Who Quietly Decides What Billions See On Google: Rafael Burde
24 Feb 2026
Contributed by Lukas
Rafael Burde holds one of the most quietly powerful jobs on the planet. As Co-Lead of Global Search Policy at Google, he helps decide what information...
Why No One Has Quit Her Company in 5 Years with Dr. Ilana Nankin
17 Feb 2026
Contributed by Lukas
In a world where employees change jobs every 18 months, Dr. Ilana Nankin has had zero voluntary resignations in five years at Breathe For Change.Ilana...
Why Most Wellness Brands Lose Trust and How to Avoid It with Dan Cox
03 Feb 2026
Contributed by Lukas
Too many wellness brands try to sell a feeling. Dan Cox decided to sell the truth.You might recognize Dan as the ultra-fit guy from The Bachelorette. ...
Why Most Goal Setting Fails (and the Exercise That Fixed It for Me)
27 Jan 2026
Contributed by Lukas
Every January, we’re told to set goals. More goals. Bigger goals. Smarter goals.And yet… most of us still feel weirdly unclear about what we actua...
Why the Best Founders Don’t Try to Sound Smart with Mike Jones
21 Jan 2026
Contributed by Lukas
What if the most important skill for founders isn’t intelligence, hustle, or speed but empathy?In this episode of Don’t Be a Jerk, I sit down with...
Why Inclusion Wins in the Long Run with Damian Pelliccione
13 Jan 2026
Contributed by Lukas
What if the thing investors call a “liability” is actually your biggest edge?In this episode of Don’t Be a Jerk, I sit down with Damian Pellicci...
A Letter From My 80-Year-Old Self
07 Jan 2026
Contributed by Lukas
This episode started with a hard moment of self-awareness.It was a quiet comment from my wife and a security camera clip I didn’t expect to watch. T...
The Hidden Success Behind 100 Box Office No. 1 Hits and The YouTube Partner Program, with Bing Chen
16 Dec 2025
Contributed by Lukas
What if your success has nothing to do with you? That is the worldview of Bing Chen. And it has shaped two massive revolutions: the YouTube creator ec...
The Quantum Physicist Who Proves Soft Skills Beat IQ
09 Dec 2025
Contributed by Lukas
Most people meet a quantum physicist and think they have nothing in common.But Anastasia Marchenkova is built different.She went from breaking the ser...
How Jesse Pujji Rewired His Mind (and Built Multiple 8-Figure Companies)
02 Dec 2025
Contributed by Lukas
What happens when you build everything you ever wanted… and still feel empty?For Jesse Pujji, that moment came after bootstrapping Ampush to a multi...
Personal Branding for Introverts: What Every Leader Can Learn from Goldie Chan
18 Nov 2025
Contributed by Lukas
What happens when authenticity becomes your superpower?For Goldie Chan, she turned her authentic, vulnerable story into a personal brand everyone want...
What 50 Cent, Disneyland, and Cancer Taught Lucy Aragon About Happiness
04 Nov 2025
Contributed by Lukas
What happens when life throws you something you can’t control?For Lucy Aragon, the answer was to keep dancing.She’s been to 105 countries, built a...
Why True Leadership Starts with Loving Yourself, with Espree Devora
28 Oct 2025
Contributed by Lukas
What does it take to build a real community in a world that rewards hustle over humanity?Espree Devora has spent over a decade answering that question...
Why Stillness Beats Hustle (and Other Lessons from a $400 Million Rise and Fall) with James Beshara
21 Oct 2025
Contributed by Lukas
What happens when you build a $400 million startup and then lose it all?For James Beshara, the answer wasn’t another company. It was a complete rewi...
Radical Transparency: The CEO’s Shortcut to Trust with Robert Yuen, Co-founder and CEO @ Monograph
14 Oct 2025
Contributed by Lukas
What if telling the truth faster could make your company more profitable, your culture stronger, and your life easier?Robert Yuen, CEO of Monograph, b...
The War for Kindness: Why Empathy Is a Superpower with Jamil Zaki, Psychology Professor @ Stanford
07 Oct 2025
Contributed by Lukas
Empathy is one of the most powerful tools we have for survival, leadership, and connection.In this episode of Don’t Be a Jerk, Healey Cypher sits do...
The Life-Changing Power of Service with Shakirah Simley
30 Sep 2025
Contributed by Lukas
When you think about “service,” you might picture a volunteer day with matching T-shirts or a line on a résumé. But for Shakirah Simley, service...
The Relationship OS: Young Han’s System for Human Connection
23 Sep 2025
Contributed by Lukas
When I first met Young Han, he wasn’t coming on my podcast. He was stepping in as a fractional CFO to help me lead through one of the hardest stretc...
The ROI of Generosity: Aaron Schwartz @Orita.ai on Luck, Boundaries, and Building People
16 Sep 2025
Contributed by Lukas
Aaron Schwartz has built and scaled companies you know — Modify Watches, Passport, Loop Returns — and now Orita.ai, helping 100+ brands land in in...
Why I Started Don’t Be a Jerk (and the Questions You’ve Been Asking Me)
09 Sep 2025
Contributed by Lukas
This one’s different. No guests, no interviews. Just me, your questions, and a few stories from the trenches.Over the last few weeks of Don’t Be a...
From Blind at Birth to Million-Dollar Founder: Sam Maddula’s People-First Playbook
19 Aug 2025
Contributed by Lukas
Born legally blind in rural India, Sam Maddula’s life changed forever thanks to a single act of kindness: a corneal transplant that restored his sig...
Why “Nice” Negotiators Win More: Master the Soft Skills That Close Big Deals, with Derek Blazensky & Todd Camp @ The Pareto Group
12 Aug 2025
Contributed by Lukas
Most people dread negotiations, whether it’s salary discussions, sales deals, or even personal conflicts. But what if negotiating didn’t have to f...
The Psychology of High-Performing Founders, with Dr. Faith Cohen
07 Aug 2025
Contributed by Lukas
What do rage rooms, co-founder breakups, and high-stakes feedback have in common?They're all windows into how our brains process stress, and how m...
Ben Gleib on Why Humor is the Best Therapy and How to Laugh Through Life’s Messiest Moments
29 Jul 2025
Contributed by Lukas
Ever wondered how comedians manage to laugh their way through heartbreak, anxiety, or even funerals?In Episode #3 of Don’t Be a Jerk, comedian Ben G...
Winning the War Within: How Adam Greenfeld Silenced His Inner Critic
23 Jul 2025
Contributed by Lukas
In this episode of Don’t Be a Jerk, host Healey Cypher sits down with Adam Greenfeld, co-founder of Frij and former co-founder of Thesis, to explore...
Why Nice Guys Win: Jules Maltz on The Power of Imperfection in Venture Capital
15 Jul 2025
Contributed by Lukas
In the very first episode of Don’t Be a Jerk, host Healey Cypher sits down with legendary investor Jules Maltz, the VC behind investments in iconic ...