On this powerful and emotional episode of Founder Talk, Jennifer Guzman, founder of Bestola Collective, and I dive into what it really looks like to scale a company through human connection. Jennifer helped grow an HR outsourcing firm from 150 to 500 clients with a 95% retention rate, and a huge part of our conversation centers on why that happened; the in-person relationship-building, the trust, the follow-through, and the genuine care most leaders overlook. Few people understand the ROI of authentic connection the way she does.
We also unpack what happens when businesses rely too heavily on technology and lose the human element. Together, we talk through how companies drift into transactional cultures, why retention collapses when communication breaks down, and how slowing down, showing up, and treating people like humans, not tickets, creates loyalty that lasts.
But the conversation goes far deeper than business. Jennifer opens up about her near-death health crisis, the culture shift after her company was acquired, and the emotional unraveling that pushed her to confront boundaries, people-pleasing, self-worth, and the darker energy that fueled her success for years. We explore her habit of saying yes to everything, tying identity to achievement, and the inner work required to become a healthier founder without burning out or abandoning yourself.
It’s raw. It’s honest. And it’s exactly the kind of conversation founders need but rarely get to hear.
What You’ll Learn
✅ Why authentic human connection is a founder’s most underrated competitive advantage
✅ How founders fall into people-pleasing, overworking, and identity through achievement
✅ What Jennifer learned from a life-threatening health crisis and emotional reset
✅ How to set boundaries, protect your energy, and build teams that communicate
✅ Why slowing down often gives founders the clarity to scale the right way
If you are a founder trying to grow without losing yourself, or if you want to build a company rooted in trust, humanity, and real connection, this episode gives you the clarity, perspective, and tools to do exactly that.
Connect with Jennifer Guzman
Guest LinkedIn: https://www.linkedin.com/in/jennifer-guzman-0442641/
Guest Website: https://bestolacollective.com/
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Timecodes
00:00 Introduction and Guest Welcome
00:08 Scaling a Business: Strategies and Successes
01:21 The Importance of Authentic Connections
02:14 Human vs. Technology in Business
02:34 Client Relationship Management
12:06 The Downfall of Transactional Culture
16:20 Founding Best Consulting
18:48 Personal Challenges and New Beginnings
30:17 Building Relationships and Trust
39:58 Facing the Mirror: Self-Awareness and Personal Priorities
41:00 The Value of Self-Worth and Esteem
42:19 Balancing Social Media and Personal Time
44:04 Childhood Trauma and Professional Life
45:46 Harnessing Dark Energy for Success
49:28 The Sacrifices of Leadership
53:38 The Importance of Family and Personal Life
58:54 Rise Chicago: Civic Engagement and Leadership
01:11:37 Final Thoughts and Reflections