The Spiritual Hustler Podcast

Episode: "What it Was REALLY Like to Sell My Business: A Conversation with Lindsay Pinchuk on Dear FoundHER"

Host: Jessica Zweig
Guest: Lindsay Pinchuk
Release Date: August 26, 2025

Episode Overview

This special episode features a deeply honest and behind-the-scenes conversation about what it’s really like to sell your business as a female founder. Jessica Zweig, now a serial entrepreneur and bestselling author, sits down with Lindsay Pinchuk, founder of Dear FoundHER and an exited founder herself, to swap stories, lessons, and the emotional truth behind leaving the companies they created. The episode explores the parallels between their entrepreneurial journeys, the reality behind a “successful exit,” and how embracing the feminine can power and heal women-led businesses. Listeners gain both tactical advice and personal stories from women who have navigated scaling, selling, and letting go.

Key Discussion Points & Insights

1. Parallel Entrepreneurial Journeys

• Jessica and Lindsay reflect on how their business paths ran in tandem through Chicago, only to truly connect after both had sold their companies.
• Both were driven by a desire to help women at pivotal life stages and eventually pivoted to supporting other female founders after their exits.
• Quote:

  “We both started companies to help the life stage we were in, and now we’re helping women do what we’ve done, the way we did it.” (Lindsay, 16:18)

Timestamps:

• Backstory: 08:11–13:58
• Parallels and connection: 16:18–17:58

2. The Realities and Process of Selling a Business

Deciding to Sell

• Jessica recounts a mentor’s pivotal advice on planning for her agency’s future—run it for life, succession, or sell (19:17–20:40).
• An internal audit led by executive consultant Amy Schuster revealed four key areas to address: people, process, pricing, and perception (23:25).

Preparing for Sale

• Jessica deliberately worked to make Simply Be an asset, not dependent on her presence; Lindsay notes she learned from watching Jessica step out of the daily business (25:09).
• Quote:

  “Everyone thinks this business is you and you’re not for sale.” (Advice from Amy Schuster, relayed by Jessica, 23:25)

The Offers and Choosing a Buyer

• Two offers emerged: a private equity firm and Hawk Media. Jessica chose Hawk due to their commitment to her team, their community-based approach, and strategic compatibility (29:20–31:19).
• Quote:

  “I had to fight for certain things… but I just knew that a strategic buyer for what I had built was better than a PE buyer.” (Jessica, 31:19)

3. Letting Go: Emotional and Operational Shifts

• The transition from founder/owner to employee was more jarring than anticipated. Jessica felt the immediate shift as soon as the new year began; she was no longer included in team communications (35:37–37:02).
• Both women discuss the reality that letting go isn’t instant even if you’re ready: “The lights go off on your business, and the next day the lights come on and it’s not yours.” (Jessica, 35:37)
• Q1 post-sale was emotionally taxing, but Jessica gradually learned to truly let go, achieving neutrality as she focused on her next venture (38:46–42:22).

4. Lessons for Future Sellers and Founders

Red Flags & Legal Advice

• Get everything in writing, but acknowledge writing can still be open to interpretation (33:47).
• There are things you can’t anticipate until after the sale; prioritize what matters most before you lose influence.

Preparing Your Business

• The business must run without you; and you must be truly ready to let go emotionally (34:39).
• Resist the urge to brush off the small stuff during closing—what feels minor may become major later.

5. Life After Exit: Reinvention & Feminine Leadership

• Jessica describes her pivot to building a business that merges spirituality, feminine leadership, and business mastery.
• She highlights building sustainable, scalable offerings: a certification-based business school, retreats, masterminds, and ongoing memberships (47:52–50:01).

Quote:

“I came out of the identity as a boss babe, which I am... But it’s not the whole story. We are so much more than what we do.” (Jessica, 44:42)

6. Reflection & Actionable Advice

Three Lessons From The Sale:

1. Follow your gut—let your body and intuition guide business decisions.
2. Be bold about your criteria and ask for what you want—meet the buyer and state your terms.
3. Cherish your reputation—not just your brand, but how you treat people and conduct yourself (50:01–52:02).

Advice to Her Younger Self:

• Start personal work and therapy earlier.
• Trust yourself—experience will come, but belief is foundational.
• Focus on service over personal gain—helping others leads to success (52:02–53:04).

Notable Quotes & Memorable Moments

• “When someone else wins, you win too. There’s just no better feeling and healing than coming together as female entrepreneurs.” (Jessica, 17:58)
• “You’re not for sale.” (Amy Schuster’s advice to Jessica, 23:25)
• “Get as much in writing as possible… but there are going to be things you can’t even think of in that transactional moment…” (Jessica, 33:47)
• “My attention was being pulled elsewhere—into something that was really giving me life.” (Jessica, 41:07)
• “To be a great leader requires you to be a great person.” (Jessica, 52:14)

Important Timestamps

• Parallel stories & relationship: 08:11–17:58
• The catalyst to sell: 19:17–23:25
• Preparing the business to sell: 23:25–25:39
• Choosing the buyer & deal dynamics: 29:20–33:04
• Emotional aftermath of selling: 35:37–38:46
• Building a new business post-exit: 47:52–50:01
• Top lessons & advice for founders: 50:01–53:04

Tone & Style

Jessica and Lindsay are authentic, unfiltered, and supportive, mixing practical wisdom with heart. Their candor about the pain and power of selling a business stands out, and both champion vulnerability and feminine leadership in today’s entrepreneurial world.

Final Thoughts

This episode is a must-listen for any woman building, scaling, or considering an exit from her business. With raw honesty, actionable insight, and a deep commitment to community, Jessica and Lindsay model what it looks like to create, let go, and rise again—on your own terms.