Why Connection Beats Achievement Every Time

Inside the Speakeasy Podcast - Your Key to Hidden Strategies & Success Stories from Top Entrepreneurs

Ever meet someone who just gets people? That’s Jennifer Hill, an Evolutionary Leader, Entrepreneur, Author, and Speaker. She’s spent her life figuring out what makes us tick, how we connect, why certain people light us up, and how to build relationships that actually last. In this episode, she shares her own journey (including calling herself a “recovering asshole”) and the simple shifts that have completely changed how she shows up for others.

Jennifer walks us through her “Plus Two” method for noticing who energizes you and who leaves you drained and why paying attention to that can change everything. We talk about the role self-awareness plays in building trust, and she shares the story behind the matching algorithm she created to predict who you’ll click with best in business, friendships, and even love.

We also get into her “anti-asshole prayer,” how she curates a high-trust network, and why being intentional about your circle is one of the best things you can do for your life and work. Jennifer’s had conversations with big names like Dr. Deepak Chopra and Bruce Lipton, but what makes her insights so powerful is how down-to-earth they feel. By the end, you’ll probably be rethinking how you connect and who you want in your life.

Key Timestamps:

[00:00:00] Welcome to Inside the Speakeasy Podcast

[00:01:05] Human connection and networking.

[00:03:09] Early educational opportunities and choices.

[00:08:39] Recovering from past failures.

[00:11:36] Early signs of creativity.

[00:15:16] Connection to self.

[00:17:32] Cherishing yourself for success.

[00:18:29] Human behavior and motivation analysis.

[00:22:02] Communication breakdown in teams.

[00:26:05] Motivators vs. Personality Types

[00:28:33] Therapy matching and its impact.

[00:30:12] Therapy matching challenges.

[00:34:05] Community building strategies.

[00:37:59] Anti-asshole prayer for networking.

[00:40:03] Human connection as future currency.

[00:41:53] The power of perspective.

Memorable Quotes:

"If you're missing that connection to the self, the rest of it collapses like a house of cards." [00:15:11] – Jennifer Hill

"What if there was no right or wrong choice? And you could trust that whatever choice you've made or choices you've made to get you here is exactly the choices you needed to make." [00:41:17] – Jennifer Hill

Links Mentioned In This Episode:

Get Your Free Profile : https://jovianarchive.com/

Connect with Jennifer Hill:

Website: https://om.app/survey/

Instagram: https://www.instagram.com/jenhillspeaker

Facebook: https://www.facebook.com/jenhillspeaker/

LinkedIn: https://www.linkedin.com/in/jenniferkhill/

Twitter/X: https://x.com/JenHillSpeaker

Connect with Eric Berman:

Website: https://speakeasymastermind.com/

Instagram: https://www.instagram.com/speakeasymastermind/

Facebook: https://www.facebook.com/speakeasymastermind/

LinkedIn: https://www.linkedin.com/in/ericberman/

Produced by Evolved Podcasting: www.evolvedpodcasting.com