The Exit Whisperer

#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. 
 
 
00:28 Welcome to the Exit Whisperer
00:39 Meet Kiri Masters: Founder of Bobsled Marketing
01:11 The Emotional Rollercoaster of Selling a Business
03:37 Kiri's Journey: From Banking to E-commerce
05:36 Scaling Bobsled: Content Marketing and Growth
09:18 The Exit Strategy: Planning and Execution
12:12 The Acquisition Process: Partnering with Acadia
15:29 Life After the Sale: Transition and Reflection
32:19 Coping with Post-Sale Emotions

#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. 
 
 
00:29 Welcome Ruthie: A Journey Begins
00:56 Building the Participation Agency
02:01 Navigating Challenges and Growth
05:44 The Impact of COVID and the Decision to Sell
08:19 The Exit Strategy: From Negotiation to Sale
10:26 Life After the Exit: New Beginnings
19:22 Empowering Female Entrepreneurs
23:37 Final Thoughts and Farewell
 
 

#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. 
 
00:28 Welcome Bridget: A Queens Girl's Journey
01:03 From Finance to Rum: Bridget's Career Shift
02:40 Building Owney's Rum: The Early Days
03:34 Raising Funds and Making Sacrifices
04:59 The Hustle: Marketing and Distribution
14:57 The Decision to Sell: Weighing the Options
20:08 Navigating the Acquisition Process
22:55 The Highs and Lows of Selling a Business
23:52 Post-Sale Realizations and Challenges
27:55 The Entrepreneurial Spirit and Motivation
34:07 Launching Rockaway Soda
35:59 Lessons Learned and Future Plans
37:26 Final Thoughts and Reflections

#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.
 
00:32 Helaine's Early Life and Career Beginnings
01:45 Discovering SoulCycle and the Birth of City Row
02:14 Overcoming Injury and Developing a New Fitness Concept
03:39 Launching City Row and Early Challenges
08:58 Fundraising and Expansion Efforts
12:43 Navigating COVID-19 and Digital Transition
18:45 The Struggles of Boutique Fitness
20:22 COVID: A Year of Layoffs and Challenges
21:45 The Final Hail Mary and M&A Process
24:43 Navigating the Acquisition
30:02 Reflecting on the Journey

#26 - Courtney Gould Miller (Lumen)

Carrie interviews Courtney Gould Miller, who successfully sold her family's marketing agency for a double-digit multiple. Courtney shares insights from her journey, which includes joining her family's business, implementing digital marketing strategies, and ultimately negotiating an impressive exit to private equity.
 
Courtney also discusses the impact of family business dynamics, the grief of letting go, and her experience transitioning into a leadership role within the acquiring company.
 
The conversation sheds light on valuing hidden assets, the pitfalls of earnouts, the emotional journey post-sale, and her passion for helping other family businesses thrive through her new podcast, Family Business Secrets.
 
00:29 Welcome to The Exit Whisperer
00:33 Meet Courtney Gould Miller
00:53 Family Business Beginnings
02:51 Growing Up in the Business
06:12 From Law to Marketing
08:33 Joining the Family Business
11:55 The Decision to Sell
16:14 Negotiating the Exit
24:25 Life After the Sale
26:50 The Emotional Journey of Selling
31:45 Courtney's Legacy and Future Plans
35:12 Closing Thoughts and Podcast Launch

BONUS - Eric Tash / Elissa Kalver (WeGotThis.org)

I was recently a guest on the Worthy for Thirty podcast with Eric Tash! We talked about my journey as an entrepreneur, how I'm helping other women entrepreneurs successfully sell their businesses, and how I'm trying to make a real difference in the world. 
 
I want to share one of Eric's conversations with Elissa Kalver, Founder & CEO, WeGotThis.org.  WeGotThis.org is the first non-profit gift registry for cancer patients and their loved ones. Elissa's story is a fascinating exploration of strength, resilience, and the power of community. Elissa founded WeGotThis.org after her own diagnosis with stage IV metastatic breast cancer close to four years ago. She asked herself, 'how can I help anyone going through a similar journey?'  Since its founding, WeGotThis.org has bootstrapped and raised $1MM for its mission. I suggest listening to this episode to learn how she's building a platform to support cancer thrivers and their loved ones while learning how you can make a difference in other people's lives too.
 
Link to the full episode:https://open.spotify.com/episode/3LDPgLNcI7kbUbxZYMYhtY?si=TOiq0MneR0KwP_6wkXo0FQ

#25 - Samantha Rose (GIR Kitchenware)

In this episode, we dive into the story of Sam, an entrepreneur who successfully bootstrapped her kitchen product business from a simple broken spatula idea to a remarkable sellable company (including inventing the first silicone spatula).
 
Sam shares her journey, including the challenges of scaling, the significant milestones achieved through Kickstarter and wholesale channels, and the strategic decisions that led to exponential growth. She also discusses the emotional and practical aspects of selling her business and offers valuable insights for bootstrapped founders considering an exit.
 
Learn how she navigated identity shifts post-sale and the importance of taking a break before venturing into new projects.
 
 
00:30 Introducing Sam
01:51 From Idea to Prototype
03:35 Kickstarter Success
07:09 From Kickstarter to Retail
09:30 Challenges and Innovations: New Products and Strategies
13:59 Pandemic Pivot: Masks and Market Adaptations
16:56 Exit Strategy: Planning and Execution
19:02 The Importance of an Exit Plan
20:48 Balancing Passion and Business Strategy
21:42 The Acquisition Journey Begins
22:56 Meeting the Acquirers
24:50 Navigating the Legal and Business Concerns
27:21 Valuation and Negotiation
33:02 Post-Acquisition Reflections
36:03 Advice for Future Founders

#24 - Emily Mueller (Wellory)

Emily Mueller shares her inspiring journey of founding and scaling Wellory, a company she started from personal health challenges.
 
Emily discusses how her entrepreneurial background and sales expertise helped her raise significant VC funds and ultimately led to Wellory's acquisition.
 
She highlights the strategic decisions behind selling the company, the impact of emerging prescription drugs on her business model, and the importance of deal-closing skills in entrepreneurship. Emily also touches on her post-exit life, including her advisory role at The Whisper Group.
 
 
00:28 Meet Emily
00:43 The Birth of Wellory
01:57  From Startup to Acquisition
02:36 The Entrepreneurial Spirit: Family Influence and Risk
04:30 Sales Skills: The Key to Success
07:42 Raising Funds: The Venture Capital Path
13:04 Navigating Market Changes
16:51 The Decision to Sell: Timing and Strategy
20:57 The Exit Process: Closing the Deal
30:45 Life After Exit

#23 - Bea Dixon (Honey Pot)

Carrie Kerpen interviews Bea Dixon, the founder of The Honey Pot, a feminine care company. Bea shares the inspiring story of how she received the idea for her business in a dream and transformed it into a thriving company that sold to Compass Diversified Holdings for over $380 million.
 
The conversation covers Bea's challenges and successes, her commitment to her company post-sale, and the unique experiences she faced as a black founder in the industry.
 
Bea also emphasizes the importance of responsible business management and the joy found throughout the entrepreneurial journey.
 
01:00 Bea Dixon's Journey: From Dream to Reality
02:45 The Struggle with Bacterial Vaginosis
05:25 The Turning Point: A Dream with a Solution
08:27 From Personal Solution to Public Product
12:58 Building the Honey Pot Brand
19:33 Breaking into Retail: The Target Deal
20:17 Breaking into Target: A Game-Changer
21:24 The Challenges of Fundraising
23:53 Growth and Expansion with New Voices Fund
26:01 The Decision to Sell: Timing and Strategy
34:12 Maintaining Control and Vision Post-Sale
40:06 Reflections on the Journey

BONUS - Carrie Kerpen (Lessons from 2024)

This was a big year for me and The Whisper Group in terms of accomplishments. It’s absolutely insane to think that we launched just 6 months ago. From the outside it all looks very exciting, but it wasn’t without challenges. 
In this solo episode, l’ll walk you through the behind the scenes and what it actually took to build this business so far.
I’m so grateful to our incredible team of advisors and women who make the magic happen daily. Excited for 2025!