Where's This Going Podcast
1) Divorce, Dating, and $25M Exits with Jaclyn Johnson
Today’s guest is Jaclyn Johnson, a serial entrepreneur, investor, and the founder of Cherub, a new platform reimagining how early-stage founders and investors connect. Before Cherub, Jaclyn built and ...Show More
2) Mallory Edens: Spearheading Female Representation in Hollywood, Overcoming a Traumatic Near-Death Accident, and Carving Out Her Own Lane Within Her Successful Family Name
In this episode, I sit down with Mallory Edens, founder of Little Ray Media, a production company focused on elevating stories by and about women in film and television. We discuss her passion for res...Show More
3) Why Pinpoint Might Be the Most Underrated Software for Brands Selling on Social Media - A Sitdown with CEO Josh Cohen
In this episode, I sit down with Josh Cohen, CEO of Pinpoint - one of my portfolio companies that just raised a $2.5 million seed round. We talk about how Pinpoint is helping brands convert their soci...Show More
4) SOLO EP: Unfiltered Q&A on VC, Creators, and the Importance of Failing Quickly
In this solo episode, I sit down for an unfiltered Q&A from my work at the intersection of venture capital and the creator economy. I talk about what I’ve learned from building on my own, the importan...Show More
SOLO EP: Unfiltered Q&A on VC, Creators, and the Importance of Failing Quickly
58:40 | Oct 6th, 2025
5) $64M Creator Fund: How Megan Lightcap Is Backing the Next Wave of Creator Entrepreneurs
In this episode, I sit down with Megan Lightcap, partner at Slow Ventures, which recently raised its $64 million creator fund to back creator-led businesses. While both Megan and I operate at the inte...Show More
6) Journey Is Fixing a Broken Loyalty System: How John Sutton Is Uniting Personalization with A Loyalty Program That Goes Far Beyond Points
n this episode, I sit down with John Sutton, CEO and founder of Journey—a company rethinking loyalty from the ground up. We talk about why the traditional points-based model is outdated, and how Journ...Show More
7) Is Phia the next $1B Business? Sophia Kianni Talks Co-Founding with Her Best Friend, How She Stays Level-Headed Through All the Media Attention, and How She's Always Been a Hustler
In this episode I sit down with Sophia Kianni to discuss Phia, the comparison-shopping platform she’s building with her best friend, Phoebe Gates that helps Gen Z save money—think Google Flights for f...Show More
8) Jeremiah Brown Isn’t Holding Back: Villa Betrayals, Unfinished Love, and Are the Friendships Over for Good?
Jeremiah Brown isn’t holding anything back. In this episode, he opens up about the friendships that fell apart after leaving the Villa, including whether things are really over with the boys who voted...Show More
9) Colleen Pelly: Secrets to Being a Standout Job Candidate, What Top Job Recruiters Are Looking For, How to Negotiate Your Salary, and Her Own Experience Scaling Her Business While on Maternity Leave
In this episode, top recruiter and founder of her company the Linchpin Co., Colleen Pelly breaks down exactly what it takes to stand out in today’s competitive job market — from resume red flags to th...Show More
10) Ashwinn Krishnaswamy on Building Iconic Brands, How Founders Burn Money on Paid Ads, and Getting Arrested
Ashwinn Krishnaswamy is the co-founder of Oklahoma Smokes and Sunpowder, and one of the most thoughtful brand minds in the game. In this episode, we talk about what it actually takes to build a brand ...Show More