The Exit Whisperer

#21 - Maggie Lord (Rustic Wedding Chic)

Maggie Lord, founder of Rustic Wedding Chic, highlights her incredible entrepreneurial journey. Maggie shares how she transitioned from being a teacher to starting and scaling a successful digital media business without prior business experience.
 
Learn about her strategies for building and monetizing her company, navigating the decision to sell to David's Bridal during COVID-19, and her shift to a corporate role post-acquisition. Maggie also discusses her current focus on mentoring female entrepreneurs, offering insights on strategic partnerships, business valuation, and the importance of mindset.
 
This episode is packed with valuable advice for women in business, from entrepreneurship and scaling a business to selling it effectively.
 
00:28 Meet Maggie Lord: The Woman Behind Rustic Wedding Chic
01:37 From Teacher to Entrepreneur: Maggie's Journey Begins
03:36 Building a Media Empire: Strategies and Growth
05:44 Monetization Mastery: Turning Traffic into Revenue
08:32 The Decision to Sell: A New Chapter
10:51 Preparing for the Sale: The Inside Story
12:14 Initiating the Sale: From Cold Email to Leadership
12:48 Valuation and Deal Structure
14:56 Maintaining Brand Independence
17:36 Transition to Corporate Life
19:16 Navigating COVID Challenges
22:15 New Beginnings: Consulting Female Founders
24:46 Final Thoughts and Contact Information

#20 - Nathalie Walton (Expectful App)

Carrie interviews Nathalie Walton, who shares her journey of transforming Expectful, a meditation app for expectant mothers, into a comprehensive wellness platform.
 
Nathalie discusses her transition from a stable role at Airbnb to co-founding Expectful, raising seed funding within 90 days, and the importance of a structured approach to fundraising.
 
She candidly addresses challenges in a male-dominated space, the mental health toll on entrepreneurs, and balancing time management with venture capital pressures. Nathalie reflects on the emotional journey of scaling and selling the business in just 28 months, emphasizing self-care, personal boundaries, and the support system required in entrepreneurship.
 
This inspiring conversation offers valuable insights and practical advice for women in business, entrepreneurs, and those interested in mindset, building, scaling, and selling a business.
 
02:22 Nathalie's Journey to Expectful
04:14 Taking the Leap: Joining Expectful
05:58 First 90 Days: Rapid Growth and Fundraising
09:23 Building Expectful: Vision and Expansion
11:01 Challenges and Realizations
13:59 Market Realities and Mental Health Toll
15:57 Facing Investor Pressure
16:29 Reflecting on Bootstrapping
17:41 Exploring Strategic Sales
19:43 The Role of a Banker
21:09 Mental Health and Personal Growth
26:19 Closing the Deal
27:53 Life After the Sale
29:59 Final Thoughts and Contact Information

#19 - Sharon Lee Thony (SLT Consulting)

In this episode of 'The Exit Whisperer,' host Carrie Kerpen interviews entrepreneur Sharon Lee Thony about her inspiring journey from a corporate job to founding and scaling SLT Consulting, which she eventually sold to Fiverr.
 
Sharon shares practical steps for transitioning from a side hustle to a thriving agency, challenges in balancing family obligations, and the significance of building a supportive network of freelancers.
 
The discussion includes insights on mindset shifts, strategic decisions, and maintaining company vision post-acquisition. Key topics cover entrepreneurship, women in business, digital marketing, and strategies for building, scaling, and selling a business.
 
Sharon also reflects on her role in launching Fiverr Agencies and her future plans as an advisor and angel investor.
 
00:28 Welcome to The Exit Whisperer
00:37 Meet Sharon Lee Thony
02:50 The Birth of SLT Consulting
05:18 Taking the Leap from Corporate
10:53 Building a Freelance Empire
13:56 Connecting with Fiverr
19:06 The Unexpected Journey Begins
19:57 Building Relationships and Growing the Agency
21:05 The Turning Point: Acquisition Talks
24:23 Navigating the Acquisition Process
26:23 Reflections on the Acquisition
29:09 Empowering Future Entrepreneurs
32:24 The Impact of Selling a Business
35:21 Final Thoughts and Future Plans

#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.
 
 
00:28 Welcome to The Exit Whisperer
00:42 Introducing Christine Merser
02:12 Early Internet Days and Blue Shoe Strategy
03:23 Obama's Digital Campaign and Early Successes
04:40 Parallels Between Internet Boom and AI
07:25 The Dot-Com Bust: Best Selections
13:46 Lessons from the Dot-Com Era
18:20 Party Rental Business and Quick Exit
24:38 Resurrecting Blue Shoe Strategy
26:32 Writing and New Ventures
27:29 Final Thoughts and Resilience

#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.
 
 
00:52 Michelle's Entrepreneurial Journey Begins
02:54 Challenges and Triumphs in Business
05:40 The Big Leap: Buying the Business
07:47 Navigating Financial Hurdles
13:52 Strategic Planning and Exit Strategy
21:15 Selling a Business: The Reality of Potential
22:30 Personal Struggles and Business Decisions
24:42 The Role of a Life Coach in Transition
25:40 Taking Time Off: Reflection and Realization
26:57 Exiting the Business: A New Beginning
29:31 Writing a Book: Prosperity After Divorce
33:24 Choosing the Right Business Partner
38:46 The Path to Profits: Final Thoughts
 
 

#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. 
 
 
00:28 Meet Richelle Pena: From Pharmacist to Entrepreneur
00:39 Building a Dental Empire: The Early Days
03:44 Challenges and Sacrifices: The Road to Success
08:01 Innovative Marketing Strategies
12:24 Expansion and Team Building
15:55 The Decision to Sell: Timing and Strategy
22:18 Valuation and Sale of Dental Practices
23:13 Retaining Real Estate for Passive Income
24:40 Life After Selling the Practice
26:50 Working with Your Spouse: Tips and Challenges
31:49 New Ventures and Future Plans
34:02 The Power Couple: Writing a Book Together
36:07 Conclusion and Final Thoughts

#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.