The Exit Whisperer

#18 - Christine Merser (Blue Shoe Strategy)

Carrie Kerpen interviews Christine Merser, an experienced entrepreneur who shares her journey with Blue Shoe Strategy and what it took to sell her business with both triumphant successes and challenging failures.
 
Christine reflects on her negotiation of a company sale for double the valuation amidst a room of skeptical men, the early days of the internet and managing forums in 1993, and her pivotal role in launching Obama's digital campaign.
 
The conversation delves into her ventures during the dot-com era, an early luxury goods online marketplace, and lessons learned from its subsequent downfall. Merser also recounts a later venture with a party rental business, navigating an exit, and imparting wisdom on managing company board dynamics and valuations.
 
  
1:00 Inside Christine’s Company Sale and Negotiation  
2:14 Lessons from the Early Internet Era  
5:30 How AI Mirrors the Early Internet Boom  
6:40 Launching Luxury Goods Online Before It Was Common  
8:01 Why a Strong Board of Directors Matters  
9:10 Early Challenges of Selling Products Online  
10:11 A Boardroom Battle Over Spending Decisions  
13:28 Why Financial Detail Can Make or Break You  
15:02 Never Give Up Your Point of View  
16:05 Learning Fast and Moving Forward  
18:20 How to Pitch Your Business for Acquisition  
20:30 Biggest Lessons from the Acquisition Journey  
22:02 Track Your Numbers — No One Else Will  
23:08 How to Know if a Company Is the Right Fit After the Sale  
24:44 Moving On and Building Blue Two Media  

#17 - Michelle Jacobik (SAVA Insurance Group)

Michelle Jacobik, a successful entrepreneur who transitioned from employee to business owner. Michelle shares her journey of buying out her employer, expanding the business, and ultimately selling it at a high valuation. With a focus on maximizing business profits and protection for business owners, Michelle's story is filled with challenges and triumphs.
 
She emphasizes the importance of planning, vision, and financial awareness, offering insights into partnerships, transitions, and life after exit.
 
Michelle's journey illustrates the power of persistence, learning, and smart financial management. This episode is a treasure trove of advice for aspiring and established entrepreneurs alike.
 
0:20 Michelle’s Story
2:14 How She Transitioned from Employee to Entrepreneur  
6:05 Smart Planning Before Taking the Leap  
8:06 Pushing Through Major Financial Roadblocks  
10:00 Getting Banks to Say Yes: Approvals & Loans  
11:41 Closing a Huge Deal Before Age 30  
15:02 Preparing for a Partner Exit the Right Way  
16:39 Putting Personal Financial Stability First  
19:10 Why Regular Business Checkups Matter  
22:15 Sell for Profit, Not Potential  
25:04 How a Life Coach Transformed Her Growth  
28:22 Finding Your Identity Beyond Your Career  
30:10 A Clear Guide to Lifestyle Redesign  
34:00 How to Choose the Right Business Partner  
35:42 Why You Need Separate Business Plans  
39:01 The Power of Individual Business Planning  
40:51 Invitation to the InVision Event  
 
 

#16 - Richelle Pena (American Pediatric Dental Group)

Richelle Pena shares her inspiring journey of building and selling American Pediatric Dental Group alongside her husband, Will.
 
Starting from a single dental office funded by bootstrapping their savings, they expanded to seven locations by focusing on strategic marketing and community engagement.
 
Richelle discusses the importance of ignoring competition noise, leveraging relationships, and understanding market needs. She also shares the thought process behind selling their business to Dentistry for Children, a Dental Service Organization (DSO), while retaining ownership of the real estate for future passive income.
 
Richelle's story highlights the vital balance of family, faith, and business priorities, and she teases her upcoming book on being a 'Power Couple' in entrepreneurship. 
 
 
1:10 Building a Dental Practice with Her Husband  
5:00 Bootstrapping the Business and Taking Big Risks  
7:36 Designing and Building Out Their Office Space  
10:50 Standing Out with Flexible Hours  
15:02 Making an Impact in Children’s Lives  
18:00 Priorities: God, Family, and Business  
20:02 Understanding Dental Service Organizations (DSOs)  
22:44 How Dental Practices Are Valued  
25:01 Why Renting After Selling Can Be a Smart Move  
27:11 Advice for Couples Working Together  
29:52 Transitioning from Business Mode to Personal Life  
32:00 Launching a New Business Together  
35:28 Key Insights from a Book on Partnerships  

#15 - Kat Hantas (21 Seeds Tequila)

In this episode, Kat Hantas, co-founder of 21 Seeds, shares the journey of building her female-focused infused tequila brand.
 
Kat discusses how a personal need for a low-calorie, less harsh alcoholic option led to the creation of 21 Seeds with the unique market insight that propelled the brand to success: women drink tequila differently.
 
Kat recounts the challenges and strategies behind scaling the business quickly, the importance of understanding your core consumer, and the strategic decisions leading to their nine-figure sale to Diageo.
 
Kat also touches on the emotional aspects of entrepreneurship, including the responsibilities of managing friends and family investments and adjusting to life post-acquisition.
 
 
00:29 Introducing Kat Hantas of 21 Seeds
02:05 The Birth of 21 Seeds Tequila
03:53 From Personal Solution to Business Idea
06:45 Launching and Scaling 21 Seeds
09:25 Marketing Strategies and Consumer Focus
20:57 The Decision to Sell and Finding the Right Buyer
33:30 Life After the Sale
36:48 Reflections on Money and Success

#14 - Lindsay Pinchuk (BumpClub)

Lindsay Pinchuk shares the incredible journey of launching and scaling Bump Club, a thriving community for expectant mothers that she bootstrapped with her background in media sales.
 
She dives into the nuances of negotiating her company's sale, including achieving double the valuation and confronting the challenges of an earn-out gone wrong.
 
Lindsay candidly discusses the emotional and practical hurdles she faced post-sale, from retaining her brand's integrity to ultimately advocating for her team's well-being.
 
Now thriving as a consultant and mentor for female founders, Lindsay imparts valuable lessons on entrepreneurship, resilience, and finding one's true calling.
 
 
00:28 Introducing Lindsey Pinchuk and The Bump Club
01:31 The Birth of The Bump Club: From Idea to Reality
02:36 Growing the Community: Early Events and Challenges
07:44 Scaling Up: Expanding Beyond Chicago
11:53 Partnerships with Major Retailers: Target and Nordstrom
16:55 The Road to Acquisition: Interest from Brand Connections
19:59 The Acquire Proposal
21:19 Valuation and Deal Structure
23:41 Team Reactions and Negotiations
25:40 Challenges with Earnouts
28:46 Realizing Misalignment
32:02 Planning the Exit
33:27 Final Negotiations and Departure
36:30 New Beginnings and Current Ventures

#13 - Sharon Gillenwater (Boardroom Insiders)

Season 2 is HERE!!
 
In this riveting episode of 'The Exit Whisperer,' we dive deep into the world of business and entrepreneurship with Sharon Gillenwater, a TikTok sensation known for her transparent exit from Boardroom Insiders, a company she sold for $25 million.
 
Sharon shares her journey negotiating with a room full of men, achieving double her company's valuation, and the trials and triumphs of exiting a bootstrap business.
 
Sharon's insight into gender dynamics in business, the importance of financial transparency, and her mission to demystify entrepreneurial exits make this a must-listen episode.
 
Learn about her perseverance, practical wisdom, transformative success in business and entrepreneurship that helped her sell her business.
 
 
00:28 Welcome to Season Two of The Exit Whisperer
00:50 Meet Sharon Gillenwater: The Founder of Boardroom Insiders
03:10 Sharon’s Journey: From Funded to Bootstrapped
06:16 The Rise of Boardroom Insiders
06:33 Navigating the Tech Marketing World
10:22 Building a Sellable Asset
13:06 The Decision to Sell: Timing and Strategy
19:58 The Acquisition Process: Finding the Right Partner
26:05 Team Continuity Post-Sale
26:16 Deciding to Stay or Leave
27:59 Financial Transparency and Viral TikTok
32:30 Navigating Gender Dynamics in Business
40:27 Books and Future Plans

BONUS - Stephanie Nadi Olson (We Are Rosie)

In this Bonus episode: we speak to Stephanie Nadi Olson. Stephanie founded and subsequently sold talent marketplace We Are Rosie for a whopping 9 figures.
 
You’ll hear the secrets of her success in this beautiful episode which shares her views on what it takes to bootstrap a business of this magnitude. 

#12 - Kat Weaver (Locker Lifestyle)

In this episode, Carrie welcomes Kat Weaver, a young and fearless entrepreneur, as she shares her incredible journey from founding Locker Lifestyle in her college dorm room to successfully selling it and becoming a pitch expert.
 
Kat candidly discusses the highs and lows of being a startup founder, the challenges of scaling her business, and the emotional rollercoaster of selling her company.
 
She also provides valuable insights into pitching for grants and funding, drawing from her own impressive record of winning 22 out of 23 pitch competitions!
 
Here's what you can expect: 
 
00:58 Kat's College Dorm story
03:49 Challenges and Growth
05:59 Pitching for Survival
11:40 Scaling and The Decision to Sell
15:18 Transition to Coaching
25:10 Current Ventures and Offerings
27:17 Final Reflections and Lessons

#11 - Melissa Rogne (Chapter Aesthetic Studio)

Join us as we dive into the incredible entrepreneurial journey of Melissa Rogne, who turned a single-location med spa in Fargo, North Dakota into a thriving business with 22 locations in partnership with the Aspen Group.
 
Melissa shares how she started without any intention of becoming an entrepreneur, her struggles and triumphs, and the power of a positive culture.
 
She reveals the pivotal moment at a conference that changed her business trajectory and discusses the importance of confidence, persistence, and a mindset of abundance.
 
Tune in to be inspired by Melissa’s story and her advice for aspiring entrepreneurs:
 
00:33 Meet Melissa Rogne: From Fargo to Fortune
01:56 Starting Small: The Birth of Rejuve
03:49 Building a Positive Culture: The Key to Growth
05:53 Overcoming Challenges: Financial Literacy and Confidence
08:54 The Power of Referrals: Growing Through Word of Mouth
12:08 Turning Point: Meeting the Aspen Group
18:45 The Aspen Partnership: Scaling New Heights
22:26 Reflecting on the Journey: Advice for Aspiring Entrepreneurs
24:26 Final Thoughts: Embracing Persistence and Abundance

#10 - Stephanie Cartin & Courtney Spritzer (SocialFly / Entreprenista)

Stephanie Cartin and Courtney Spritzer, the co-founders of SocialFly and Entreprenista, share countless stories about their entrepreneurial journey.
 
They discuss the pivotal moments that shaped their success, the challenges of managing a startup, and their strategic approach to scaling and eventually selling their social media agency.
 
Carrie, Stephanie and Courtney have known each other for years! And now reflect on the importance of mentorship, community, and remaining adaptable in the face of unforeseen challenges like the pandemic.
 
The episode also highlights their new venture, Entreprenista, an empowering community for female entrepreneurs. Here's what you can expect:
 
00:29 A Pivotal Moment: Meeting Future Competitors
02:48 The Story Behind SocialFly
04:06 Early Challenges and Successes
06:23 Partnership Dynamics: Working Together
11:33 Mentorship and Networking: The Power of Connections
14:44 Planning for the Future: Built to Sell
16:43 Entreprenista and Beyond
25:02 Navigating the Sale: Challenges and Emotions
33:53 Life After the Sale: Reflections and New Beginnings