Jack Winston is the co-founder of Be Present, a screen time reduction app using app locking, gamification, and social challenges to help people take back control of their attention.

He joins Randy to unpack how a healthy relationship with tech became a keystone habit in his own life and how that realization led him and his brother to build a product that's now helping hundreds of thousands do the same.

We discuss digital wellness culture, screen addiction’s downstream effects, behavior design, and the future of attention as a status symbol.

Shownotes:
00:00 – Intro to Jack Winston and the origins of Be Present
02:00 – How gamification and social competition make screen time reduction stick
05:00 – Understanding screen addiction as a keystone habit
08:30 – Drawing the line between digital inputs and mental health
11:00 – Why digital wellness isn’t mainstream yet—and how that’s changing
14:00 – Offline status as a new cultural currency
16:00 – Why saving time is the ultimate value prop
18:00 – Unpacking user behaviors and unexpected digital dependencies
21:00 – Gen Z: the most addicted and the most aware
24:00 – How Jack balances his own digital habits as a founder
27:00 – Frameworks for tech reflection and intentionality
30:00 – Rapid fire: last deleted app, favorite tech, underrated habits
35:00 – Where to find Jack and download Be Present

Jason Levin is the Chief Memelord at Memelord Technologies, the author of Memes Make Millions and the creator of Silly Valley. A college dropout who cold-DMed his way into Silicon Valley, Jason spent three years ghostwriting viral content for top founders and VCs before becoming Head of Growth at Product Hunt. Now, he builds silly software tools for meme marketers to go viral and make more money, interviews top entrepreneurs and creators on the Jason Levin Show, and writes his weekly blog Cyber Patterns which he has been publishing consistently for over 180 weeks straight.

[00:00] - Introduction and Jason's background

[04:22] - Humor as the last frontier untouched by AI

[06:05] - Content creation and the "ultimate content hack"

[08:16] - The barbell theory of online/offline presence

[10:57] - Importance of taking time offline for clear thinking

[14:23] - Focused experiences with music and entertainment

[18:31] - Building meaningful online relationships

[25:00] - How to reach out to people you admire online

[27:52] - Rapid fire questions about digital wellness

[32:53] - Where to find Memelord Technologies

Jason Kuperberg is the co-founder of HyperWrite (OthersideAI), an AI writing and research platform with millions of users. Named to the Forbes 30 Under 30 list in 2024 for consumer technology, Jason studied biotechnology at Syracuse University before pivoting to entrepreneurship. Based in New York City, Jason balances his work in AI and innovation with his passion for running, having qualified for the Boston Marathon and holding a USATF marathon specialist coaching certification. Combining his interests in AI and fitness, Jason created Roast My Strava, an app that has been used by thousands of athletes around the world. He continues to develop tools and experiences that enhance creativity, productivity, and wellness through emerging technologies.

0:00 – Intro

1:30 – The Three Buckets of Jason’s Life

2:50 – Early Entry Into AI

3:40 – A Lifelong Runner

5:15 – Where AI Meets Real Life

7:30 – The Power of Online-Offline Connections

10:30 – Agency, Free Will, and the TikTok Moment

13:00 – Taking Initiative IRL

14:30 – Tools That Enable Real-World Connection

18:00 – Friend Curation as a Practice

21:00 – The Uncanny Valley of AI Companions

24:30 – From Glasses to Neuralinks

28:00 – The Small Talk We’re Missing

29:50 – Jason’s Personal Tech Guardrails

33:00 – Friction as a Feature

36:40 – Context-Aware AI Tools

39:00 – The Future of Wellness x Tech

41:15 – Sticky Notes and Side Quests

Jacklyn Dallas started making tech explainer videos for her grandmother as a 13-year-old on YouTube and has built a wildly popular channel, NothingButTech, making educational and entertaining videos about the tech that changes our daily lives. Her content moves between tech reviews to interviews with some of the industry's topmost leaders, all distinguished by her authentic, deeply engaged narrative presence and a powerful sense of energy and excitement in her videos.

00:00 – Intro & Why This Conversation Matters

00:47 – Jacqueline’s Warm Welcome

01:06 – Tech’s Double-Edged Sword & the Loneliness Epidemic

01:48 – Jacqueline’s Origin Story: From Grandma’s Tech Help to YouTube Stardom

04:29 – The Creator Dream: What Aspiring YouTubers Don’t See

06:46 – Navigating the Algorithm vs. Creative Integrity

09:57 – Dealing with 10/10 Videos & Detaching from Validation

11:33 – Vanity Metrics, Value, and Building the Right Audience

13:31 – Digital Wellness & Guardrails as a Tech-Centric Creator

16:20 – Tactics That Work (and Don’t) for Digital Balance

17:52 – Triggers to Recalibrate & Fighting Creative Fatigue

20:13 – Time Transfers: Replacing Screen Time with What Matters

21:48 – Trends in Screen Time & Bouncing Back from “Off” Days

23:43 – Identity Shifts & Momentum: Becoming Who You Want to Be

25:02 – From the Internet to Real Life: Building In-Person Relationships

26:55 – Feeling Alone in NYC to Hosting Community Dinners

29:43 – Hosting Events: The Low-Lift MVP Version vs. Scaling Up

31:38 – Curating Connection: Seating Charts, Shared Interests & Thoughtful Intros

32:46 – From One-to-Many to One-to-One: Scaling Real Relationships as a Creator

34:22 – Lessons from Taylor Swift on Intimacy at Scale

35:09 – Rapid Fire Q&A Begins

43:13 – Closing Thoughts & Where to Find Jacqueline