The Exit Whisperer

By Carrie KerpenBusiness Entrepreneurship

The Exit Whisperer episodes

April 01, 2025 #36 - Carrie Kerpen (The Whisper Group)
In the inaugural episode of season four, Carrie reflects on the significant milestones surrounding April 1st, including selling her company on April Fool's Day and the release of her new book.

She discusses the intense and rewarding process of writing the book, which combines fiction, real-life examples, and an implementation guide for business growth. Additionally, she provides insights into her journey with the Whisper Group, an exit readiness advisory practice for female founders.

The episode touches on the challenges of scaling a business, the importance of mindset, team selection, and her unique approach to planning and growth.

00:00 Introduction and Season Kickoff
00:34 April Fool's Day and Personal Reflections
00:57 Introducing the New Book
03:09 The Whisper Group Journey
04:47 Challenges and Mindset
06:36 Team Building and Partnerships
08:27 Lessons Learned and Advice
09:21 Conclusion and Encouragement

11 min
March 11, 2025 #35 - Gwen Whiting (The Laundress)
Gwen shares her remarkable journey of founding The Laundress, a luxury laundry brand.

From securing a government-backed loan to self-financing with credit cards, Gwen details her determination and innovative spirit. She discusses the challenges and successes of building her business, the experience of negotiating a sale with Unilever, and her emotional turmoil post-acquisition.

Gwen reflects on the aftermath of the sale, the impact of a major product recall, and her eventual decision to launch her next venture, 'The Fill'.

2:13 How She Funded the Business With an SBA Loan
4:24 The Early Struggles of Getting Market Acceptance
7:13 Winning Customers Through Product Education
8:45 Building Confidence and Learning to Believe in Herself
10:30 Taking Bold Risks by Self-Financing the Company
13:37 Why She Preferred Control Over Raising Outside Capital
16:10 Hitting 30% Year-Over-Year Growth
18:22 Her Vision for Scaling a Truly Impactful Brand
21:20 Getting the Call to Meet at Unilever Headquarters
24:00 The Tough Realities of Negotiating an Exit
27:35 Feeling Completely Unprepared for the Acquisition Process
30:36 How Disorganization Created Post-Sale Challenges
33:00 The Consequences of Weak Leadership and Poor Accountability
34:58 The Personal Horror of Being Tied to a Damaged Brand
37:10 The Heartbreak of Feeling Like She Let Her Team Down
39:00 The Painful Silence During a Difficult Transition
40:41 Why Meaningful Exit Conversations Never Happened
43:40 Navigating the Hardest Parts of an Uncomfortable Transition
46:07 Launching a New Community-Driven Brand

50 min
March 04, 2025 #34 - Sarah Weiss (Elite Roofing Supply)
Sarah Weiss shares her incredible journey of growing Elite Roofing Supply from a family business into a major industry player. Sarah, inspired by her father's entrepreneurial spirit, cashed in her 401k and jumped into the roofing supply industry, growing the company to 26 locations and becoming one of the top distributors in the market.

She discusses the challenges of running a family business, the intense growth phases, and the strategic considerations that led to selling the company to Gulf Eagle Supply. Sarah provides an inside look at the emotional and mental preparations required for such a significant exit, as well as her personal reflections and plans post-sale.

This episode covers everything from bootstrapping to navigating high-stakes negotiations with Goldman Sachs, making it a must-listen for aspiring entrepreneurs and business owners.

1:03 How Sarah First Stepped Into Entrepreneurship
2:06 Starting Elite Roofing Supply With Her Dad
4:36 Navigating Family Dynamics in a Business Partnership
6:10 Smart Growth Strategies That Drove Their Success
7:30 The Early Struggle to Hit Profitability
9:00 Pushing Through the Fear of Failure
10:37 Knowing When It’s Time to Think About an Exit
11:47 How the Roofing Distribution Business Really Works
12:38 Identifying the Right Strategic Partners for Acquisition
13:30 Why She Chose Goldman Sachs to Lead the Sale
14:29 Preparing Mentally and Emotionally for the Sale Process
17:12 The Unique Strength of Family-Owned Companies
18:09 Getting Ready for the Emotional Roller Coaster Ahead
20:50 Prioritizing Rest and Recovery After the Sale
22:24 Giving Herself Time to Discover What Comes Next

24 min
February 25, 2025 #33 - Laurel Mintz (Basset Furniture & Elevate)
Laurel shares her journey of being thrust into running her father's Bassett Furniture franchise business at 26 when he was diagnosed with stage four cancer.

She details the emotional and professional challenges of managing and eventually selling the over-leveraged business back to corporate, which financially devastated her family.

After overcoming these hardships, Lauren launched her own successful marketing firm, Elevate, which she later transitioned to an ESOP for her employees. She also discusses the inception of Fabric VC, a venture fund supporting women and BIPOC founders, highlighting its unique marketing-driven approach to investment.

2:20 Laurel’s Unexpected Takeover of the Company
3:40 Facing Day-One Challenges as a Young Leader
6:53 Mastering the Art of “Fake It Till You Make It”
8:25 Navigating the Realities of an Overleveraged Company
9:12 How She Successfully Restructured the Company’s Debt
11:20 Negotiating the Sale Back to the Corporate Parent
13:37 Reinventing Her Career From the Ground Up
14:54 Launching Elevate, Her Own Marketing Agency
16:18 Making the Leap Into Venture Capital
18:24 Uncovering a Surprisingly Diverse Business Model
20:00 Understanding the Transformative Power of Venture
21:36 Building a Truly Differentiated Venture Fund
22:48 The Pros and Cons of ESOPs Explained
25:02 The Latest Progress on Raising Fabric VC
27 min
February 20, 2025 #32 - Kate Watts (Faire Design)
Kate Watts, a trailblazer in the agency space, narrates her impressive rise from being the president of Huge, a top digital agency, to launching and subsequently selling her own agency, Faire Design, to The Atlantic.

She opens up about the challenges and triumphs she faced during the integration and spin-off process, eventually regaining majority ownership and rebranding as Long Dash. This conversation is filled with valuable insights on mergers, acquisitions, and navigating the entrepreneurial landscape.

2:44 Launching Fair Design in 2017
5:30 Rapid Growth and an Unexpected Acquisition Offer
7:51 Considering Whether Fair Was a Long-Term Play
9:10 How She Transitioned From Agency Leader to Acquiree
11:10 The Moment a Buyer Proposed Acquiring Fair
13:31 Learning How to Value and Negotiate Her Own Deal
14:54 The Atlantic’s Deep and Historic Legacy
19:01 The Challenges of Scaling as a Modern Brand
20:06 Choosing to Become Operationally Independent
22:02 Involving the Team in the Naming Process
23:00 The Journey to Regain Majority Ownership
24:05 What’s Next for Long Dash
27:14 Staying Open to Future Partnerships and Opportunities
30 min
February 13, 2025 #31 - Christine Slocumb (Clarity Quest Marketing)
Christine shares her experiences negotiating five separate Letters of Intent before finally securing a deal that doubled her company’s valuation.

Christine's three-year saga involved both personal and professional challenges, including contracting long COVID, which ultimately influenced her decision to sell. The discussion delves into the intricacies of the selling process, the importance of choosing the right advisor, and how perseverance is key in the world of mergers and acquisitions.

Christine also reveals how writing her book, 'Stop Starvation Marketing,' helped her stay grounded amid the chaos.

1:21 Why It Took Five Tries to Finally Close the Deal
3:12 What Founders Need to Know About LOIs
6:10 Launching an Agency After Major Setbacks
7:32 Shifting From Consulting to Building an Agency
8:55 The Moment She Realized the Company Needed Restructuring
10:20 Debating Whether to Sell During COVID
12:00 Receiving a Full All-Cash Offer for the Agency
14:35 Why Buyers Wanted a Strong Platform Company
16:06 When Legal Bills Start Piling Up From Multiple LOIs
19:11 Choosing the Right Advisor Can Change Everything
21:55 The Final Hesitation Before Signing the LOI
23:02 Why Timing Is Everything in Business Deals
24:01 Building a Complete and Investor-Ready Data Room
27:30 Writing a Book While Selling Her Company
30 min
February 11, 2025 #30 - Kiri Masters (Bobsled Marketing)
Carrie interviews Kiri Masters, the founder of Bobsled Marketing, a retail marketing agency focused on platforms like Amazon.

Kiri shares her journey from starting the business in 2015 with no background in retail or agencies to successfully growing it and selling to Acadia in 2021. Despite the financial success, Kiri discusses the emotional challenges she faced post-sale, akin to a 'postpartum depression' for founders.

They delve into her strategic growth driven by content marketing and the careful selection of an M&A advisor. Kiri candidly talks about the emotional vulnerability during the sale process, the transition to working within Acadia, and her eventual realization that she needed to return to her entrepreneurial roots. Now, Kiri is taking time off, exploring new opportunities, and sharing her journey through a substack, a podcast called 'Obsession', and coaching.

1:01 The Story Behind Kiri’s Successful Company Exit
5:34 The Origin Story of Bobsled Marketing
7:14 How Amazon’s Programs Actually Work Behind the Scenes
9:54 Her First Thoughts About Eventually Exiting the Business
12:41 The Power of Partnering With the Right M&A Advisor
14:42 Why Industry Experience Can Make or Break an Exit
18:02 How She Built a Tight, Strategic List of Buyers
22:09 The Personal Decisions That Steer Company Growth
24:58 What Transitioning Into the Acadia Team Really Looked Like
28:25 Adjusting to Having a Boss After Being a Founder
30:54 Why Founders Need Time Off After Selling
32:43 The Unexpected Wave of Sadness After an Exit
35:08 Finding Support Through Therapy and Medication
37 min
February 06, 2025 #29 - Ruthie Schulder (The Participation Agency)
Ruthie Schulder shares her story of building and selling her experiential agency. Ruthie discusses the challenges and strategies that led to her agency's success, her decision to pivot and eventually exit the business during the COVID-19 pandemic, and how she has transitioned to coaching other female entrepreneurs.

She emphasizes the importance of knowing when to move on, positioning and sales, and aligning business with personal values and goals.

1:08 Meet Ruthie: Founder, Leader, Visionary
2:22 How She Started The Participation Agency
4:16 The Key Drivers Behind Their Rapid Growth
6:11 Why Depth Matters More Than Scale in Agency Building
7:51 The Big Shift Into Becoming a Digital Agency
9:00 When the Universe Pushes You Toward Change
10:25 A Pandemic-Era Bidding War Begins
12:22 Bringing In an Investment Banker to Navigate the Sale
14:29 Choosing the Best Agency Fit for Their Clients
16:47 Why She Stayed On After Selling the Company
18:30 Embracing Change and New Professional Opportunities
19:57 Moving Into Coaching for Female Entrepreneurs
22:34 Aligning Your Business With Your Personal Gifts
23:40 Rediscovering Identity After Exiting a Business

25 min
February 04, 2025 #28 - Bridget Firtle (Owney's Rum)
Bridget shares her remarkable journey of founding, building, and eventually selling Owney's Rum, a New York-based distillery.

From her early career at a hedge fund to identifying market opportunities in craft spirits, she leveraged her finance background to launch a successful rum brand. Bridget discusses the challenges of raising initial capital, running a lean operation, and handling media attention.

She also delves into the complexities of selling her business to Proximo Spirits, the emotional and operational transitions, and lessons learned. Now focused on her new venture, Rockaway Soda, Bridget reflects on balancing passion with strategic planning in the non-alcoholic beverage market.

2:44 The “Aha” Moment to Build a Rum Distillery
4:43 Raising $500K to Bring the Vision to Life
6:25 How Friends and Family Backed the First Round
8:02 A Deep Passion for Crafting Great-Tasting Rum
10:02 Press Coverage That Skyrocketed Their Visibility
12:00 Self-Distributing Rum Out of the Back of Her Car
14:29 A Surprisingly Short Timeline From Launch to Sale
17:10 Early, Informal Talks With a Potential Acquirer
19:25 Building a Smart Cash-Off Strategy
22:06 Negotiating With Major Industry Players
25:49 Navigating the Legal Maze of Selling a Business
29:39 Why Freedom Was Her Ultimate Motivator
31:51 Lessons Learned From Previous Ventures
34:19 Launching Rockaway Soda as a Creative Outlet
37:10 Managing Anxiety Through Entrepreneurial Experience
40 min
January 28, 2025 #27 - Helaine Knapp (CityRow)
Helaine shares her compelling journey of founding CityRow, a boutique fitness company inspired by her own need for a low-impact yet intense workout.

From her childhood struggles with weight to her professional endeavors in publishing and tech startups, Helaine intricately narrates her path to building CityRow. She discusses the challenges faced, including a debilitating injury that led her to discover rowing and the obstacles in finding real estate and funding. Despite raising over $20 million and expanding the business, the COVID-19 pandemic hit hard, causing substantial financial strain.

Helaine opens up about the eventual decision to sell CityRow, the emotional turmoil of letting investors and team members down, and the relief of finding a suitable home for her concept. She also talks about her book, 'Making Waves,' which serves as a therapeutic recount of her entrepreneurial journey.

Helaine's story offers a raw and real look into the high stakes of starting and running a business, and her resilience through it all.

2:10 How an Injury Sparked Her Fitness Discovery
5:51 The Real Benefits of Rowing Workouts
7:24 The Journey to Finally Signing the Lease
10:28 How She Raised Over $20 Million
12:44 Expanding the Company Into Digital Fitness
14:25 Navigating Investor Concerns During COVID
18:41 Her Strategy for Customer Acquisition
20:22 The Challenges That Hit After Fundraising
22:30 How the M&A Process Started — and the Struggles
24:41 Finding and Approaching Potential Acquirers
27:54 Announcing the Acquisition by WaterRower
33:20 Writing Her Book as a Healing Journey
36:05 The Major Shift That Changed the Book’s Ending
39 min