Explorez tous les épisodes du podcast The Exit Whisperer

In the first live recording of The Exit Whisperer at Luminary, Suneera Madhani shares how she turned a rejected idea into one of Florida’s biggest startup success stories. At 25, she pitched a subscription-based payment processing model to her employer. They passed—so she quit, moved back home, teamed up with her brother, and built Stax from scratch.

Suneera breaks down what it really took to scale, raise capital later than most fintech companies, survive investor rejection, and navigate multiple exits—including Stax’s $1B valuation as Florida’s first unicorn.

00:01 How Suneera Madhani Got Started

04:46 The Reality of Being a Founder Mom

08:29 Learning to Become a CEO

11:45 The Rejected Business Idea

14:07 Pitching Her Boss

16:14 "You Can't Go Back To The Same Job"

17:28 Quitting to Start the Company

18:02 Explosive Early Growth

18:41 Breaking Down the Exits

20:17 What Investors Actually Fund

21:43 Rejection, Bias & Scaling Challenges

23:57 Knowing When You’re Ready

26:30 Founder vs CEO Mindset

29:36 The Playbook for Scaling

33:15 Why Cool Doesn’t Equal Business

36:08 Acquired, Not Retired

Natalie built a wildly recognizable beauty brand, raised $13 million, got it into major retail, and still came away with the same uncomfortable realization a lot of founders quietly have: the number in the headline and the money you actually feel are not the same thing.

This isn’t a Cinderella story. It’s what happens when a smart founder tells the truth about money, control, and what an exit actually feels like after the applause stops.

01:09 Meet Natalie Mackey

02:44 The Pivot That Changed Everything

05:15 Why Beauty Breaks E-Commerce Rules

07:25 The Product That Took Off Overnight

08:09 Fundraising Is Timing, Not Talent

13:06 The Decision to Sell Instead

18:22 The Truth About “Winning” an Exit

19:07 Why the Second Time Feels Different

20:38 AI Is Giving New Founders an Edge

21:30 Losing the “Founder” Identity

24:45 The Pressure to Do It Again

26:33 Why You Just Have to Start

28:00 Money, Risk, and Never Feeling Safe

30:18 The Traits That Actually Matter

In this episode of The Exit Whisperer, Carrie sits down with Andrea Johnston, founder of Pure Communications, to unpack what most founders never say out loud: sometimes the business is thriving, the numbers are strong, the offers are real, and you still know it’s time to sell.

They get into building with intention, why niche agencies scale faster than scattered ones, what private equity actually wants, and how to know whether you’re growing a business… or just feeding a machine that no longer fits your life. Andrea also opens up about what she would do differently, why succession planning matters more than founders think, and the hard truth that reacting emotionally will cost you more than almost any bad strategy.

00:54 Meet Andrea Johnston

02:48 Why She Left Corporate to Start Her Agency

04:51 The Gap Between “Starting” and Building a Real Business

05:23 How She Scaled Using Only Her Network

07:27 The Decision to Niche Down

10:31 The Real Growth Engine: Existing Clients

12:15 How Private Equity Entered the Picture

17:38 Inside the Sale Process

18:14 What Actually Changes After You Sell

19:28 How Acquisitions Create Opportunities for Your Team

20:15 The Second Exit: Moving Fast in Private Equity

21:35 Burnout at the Top

25:22 Taking 2 Years Off

28:41 Building “Fuel for Female Founders”

32:24 Final Lessons on Exits, Growth, and Letting Go

In this episode of The Exit Whisperer, Carrie sits down with Lana Powers (founder of Powers PR) to unpack a truth most founders ignore until it’s too late: success can still be the wrong path if it’s killing you to sustain it.

They get into rebuilding a company just to make it sellable, why hitting a peak can be more dangerous than failing, and how founders confuse “being needed” with “being healthy.” Lana also opens up about the aftermath of selling, the second-guessing, the “what if I kept going,” and redefining success beyond revenue, status, or control.

00:56 Meet Lana Powers

02:57 Hitting Rock Bottom As A Founder

03:57 Starting Powers PR From Scratch

05:17 Growing Slowly Into Real Momentum

06:15 Scaling While Pregnant With Twins

10:53 The Reality Of Running A PR Agency

14:58 Burnout In The Wellness Industry

15:54 Rebuilding The Business The Right Way

17:10 The Client That Changed Everything

18:50 Learning To Detach As A Leader

19:37 When Your Body Starts Breaking Down

22:35 How She Chose The Right Buyer

23:58 Life After Selling The Business

27:00 What Success Looks Like Now

In this episode of The Exit Whisperer, Carrie sits down with Caren Sinclair — a serial founder, operator, and dealmaker who has sold multiple businesses and is honest enough to say the quiet part out loud.

Caren breaks down what founders rarely admit in public, how early investor pressure can push you into deals you wouldn’t choose in a stronger position, why equity-only exits often sound better than they feel, and how financial stress doesn’t just hurt your business… it distorts your judgment. They also get into choosing the right co-founder, raising from the right people, and why safety (not comfort) is the real prerequisite for smart entrepreneurship.

03:31 The Moment She Walked Away From Safety

06:01 Why Most Founders Make Bad Bets

07:54 The 2-Year Exit That Wasn’t What It Seemed

16:05 The Truth About “No Cash” Exits

20:43 Starting Again After Selling Too Soon

24:01 Why Salary Can Save Your Startup

24:36 The Partnership That Changed Everything

26:08 Raising Money Without Losing Control

26:55 Why Big Funding Can Kill Discipline

29:10 When Competition Turns Into Survival

32:24 The Lesson Most Founders Learn Too Late

33:41 How To Actually Pick A Co-Founder

36:08 The Mindset That Makes You Unbreakable

Rachel Sklar built the most powerful women-in-tech network before “women’s communities” were trendy. In this episode of The Exit Whisperer, Carrie Kerpen sits down with Rachel, founder of The Li.st, to unpack the kind of exit founders never brag about — because it’s not a flashy SaaS story.

They get into the messy parts people skip: charging for community (hello, “pay to be her friend” headlines), why “perfect-fit” acquisitions die when you wait too long, what happens when the buyer’s lawyer kills the vibe, and why sometimes the smartest deal is the one that lets you sleep at night — even if it’s not the biggest number.

02:25 Meet Rachel Sklar: The Original Community Builder

03:05 Building The Li.st Before “Women’s Networks” Were Cool

06:09 Protecting Trust While Scaling

09:34 The Controversy

23:10 The Lessons Nobody Tells You

32:23 The “Perfect CEO” Idea (And The Plot Twist)

32:41 Startup Institute33:01 What The Li.st Could’ve Become

35:12 Pregnancy Changes The Timeline

36:30 COVID-19 Proves The Li.st’s Real Value

37:46 Handing Over The House You Built

52:30 Rachel’s Next Chapter After The Exit

58:54 What She’d Do Differently Now

Kristine Tokonow bootstrapped her way into major retailers and global brands, survived COVID, supply chain chaos, labor shortages, pregnancy, and a year that pushed her to the edge. She knew she was burned out in 2021 — but she didn’t sell then. Instead, she rebuilt, stabilized, and intentionally positioned the company to be worth walking away from.

In this episode of The Exit Whisperer, Carrie sits down with Kristine, founder of The Conery, just days after selling the company she spent 12 years building from scratch. What started as a simple question — why are ice cream cones still terrible? — turned into a bootstrapped manufacturing business supplying major brands, theme parks, and retailers.

00:50 Meet Kristine Tokonow

01:17 The Idea That Didn’t Exist Yet

02:19 From Side Hustle to Real Business

04:03 Scaling, Scrappiness, and Early Growing Pains

10:19 When COVID Hit the Business

11:21 Burnout, Pregnancy, and Pressure

13:30 Knowing It Was Time to Sell

14:15 Rebuilding Energy Before an Exit

15:27 Why 2021 Nearly Broke Everything

16:53 The Advisor Who Changed the Outcome

18:57 The Emotional Reality of Selling

20:04 The Day After It Was No Longer Hers

21:39 Letting Go and Walking Away

23:16 What Comes After the Exit

Selling your company isn’t always a flex. Sometimes the bravest exit is walking away. If you’re “fine” but your body is screaming, this episode is for you. In this episode of The Exit Whisperer, Carrie sits down with Roslyn McLarty, co-founder of The GIST, who left a fast-growing, funded company when burnout stopped being a vibe and started being a warning sign.

We get into the unsexy truth founders don’t post: the eye twitch, the dread, the “take a long weekend” advice that solves nothing, and the moment you realize it’s not just hard — it’s misaligned. Roslyn breaks down what burnout actually is (a chronically activated nervous system), how to tell “push through” from “get out,” and why chasing outcomes (revenue, valuation, the headline) is the fastest route to losing yourself.

02:19 Meet Roslyn McLarty

04:18 Building The GIST From Scratch

05:08 Why Fundraising Was an Uphill Battle

07:24 Role Misalignment: The Silent Burnout Trigger

12:41 Hitting Burnout — And Finally Stopping

19:56 The Inner Critic That Won’t Shut Up

20:16 How Burnout Warps Business Decisions

21:22 The Emotional Whiplash of Leaving Your Company

22:19 Processing Grief, Relief, and Identity Loss

24:25 Finding Alignment After the Exit

26:16 Rebuilding Without Burning Out Again

29:50 How to Recognize and Regulate Burnout

33:44 What Every Founder Needs to Hear

Meghan built exactly the kind of business founders are told to want: flexible, profitable, and “lifestyle-friendly.” Then her 10-year-old assumed she’d be working at hockey practice — and she realized the business had quietly taken more than it ever gave back.

In this episode of The Exit Whisperer, Carrie sits down with Meghan Block, founder of Wicked Good Mom Media to unpack how a single local domain turned into a multi-market media company — and why scaling it further would’ve required giving up the one thing she wasn’t willing to lose: presence with her kids.

01:31 Meet Meghan Block: From Domain To Media Company

03:06 Building Wicked Good Mom Media

05:45 Scaling A Hyperlocal Business

10:06 The “Summer Of Mama” Reset

12:08 The Moment She Decided To Sell

12:59 Getting The Business Exit-Ready

15:01 Why Private Equity Wasn’t The Answer

15:27 Defining The Right Buyer

16:03 Protecting Financial Security After The Sale

16:17 Why She Refused A Long-Term Earnout

16:57 Finding The Buyer By Accident

18:15 When Family Becomes The Real KPI

21:35 The Boundary That Changed Everything

27:35 What’s Next After The Exit

Most acquisitions fail because founders obsess over the price — not the people. Monica Kocher built and exited two companies by doing the opposite. In this episode, Carrie sits down with Monica, a rare founder who bootstrapped and sold twice — once through a strategic partnership that became an acquisition, and once through an advisory relationship that turned into a buyer.

This is a masterclass in what most founders get wrong: thinking exits are transactions, not long-term relationships. Monica breaks down why partnering before you sell can be the difference between a smooth exit and a cultural disaster, and why letting a potential acquirer see your company up close is not weakness, it’s leverage.

01:00 Meet Monica Kocher

02:15 First Exit: Building And Selling Gugu Chew

04:08 How The Acquisition Came Together

07:15 Looking Back On The Gugu Chew Exit

08:56 Second Company: The Smart Gift Idea

11:04 Partnering With 1-800-FLOWERS

13:16 Why Advisory Boards Matter More Than You Think

13:57 Aligning Vision With Advisors Early

14:47 How COVID Changed Corporate Gifting Forever

15:15 Scaling Fast Without Losing Control

16:08 Inside The Acquisition Process

16:44 When Advisors Become Acquirers

20:34 Advice For Women Building Toward An Exit

23:43 Final Takeaways + How To Find Monica

In this episode of The Exit Whisperer, Carrie sits down with Amanda Goetz, founder of House of Wise and author of Toxic Grit, to unpack one of the most dangerous deal structures founders don’t talk about: the equity sale with no cash.

Amanda shares the full, unfiltered story of selling her fast-growing brand in an equity deal that looked “perfect” on paper — and how it quietly turned into a nightmare. We get into the emotional state founders are in when they sell, the paperwork everyone assumes gets handled, and the brutal reality of what happens when it doesn’t.

00:47 Meet Amanda Goetz

02:13 The Rise Of House Of Wise

02:42 Challenges In Fundraising

04:30 The Equity Deal (No Cash, High Risk)

04:43 When The Deal Started To Go Wrong

07:15 The Personal And Financial Fallout

10:28 Lessons Learned And Hard Advice

12:46 Decisions Made Under Pressure

13:39 Letting Go: Identity, Trauma, And Loss

14:38 When New Management Took Over

15:57 Starting Over: 2025 And Beyond

16:19 Finding New Roles And Creative Energy

16:57 From Newsletter To Book Deal

20:25 What “Toxic Grit” Really Means

23:17 The 10 Characters That Shape A Life

Your “dream exit” is probably a math problem you haven’t done yet. Gigi Lee Chang built Plum Organics to a reported nine-figure exit to Campbell Soup Company — then tells the part founders don’t talk about: dilution, losing control, and why the headline is rarely what hits your bank account.

In this episode, Carrie Kerpen sits down with Gigi Lee Chang to unpack the real trade: raising money to go faster… and watching the cap table quietly decide what you “walk away with.” We talk about the pouch pivot that changed the category, the behind-the-scenes reality of board power, and the uncomfortable truth that “entrepreneur” became a status badge — not a job description.

02:52 Meet Gigi Lee Chang

04:17 The Idea Behind Plum Organics

07:26 Early Challenges Building The Brand1

0:39 The Pouch That Changed The Category

22:07 The Shift To Plum As The Core Brand

22:55 Looking Back On The Decision

25:01 When Gigi Lost Control Of The Company

25:48 How Investors Actually Think

28:15 Selling Plum Organics To Campbell’s

29:20 Life After The Acquisition

30:32 Entrepreneur Vs Small Business Owner

41:18 What Gigi Is Building Now

The first offer was three times too low — and Stacy Stahl almost walked away. Instead, she did something most founders never do, and it changed the entire deal.

In this episode, Carrie sits down with Stacy Stahl (founder of How He Asked — yes, the “Gossip Girl of proposals” — acquired by The Knot) to break down the part founders don’t post: the lowball, the power move, and the moment you realize your business is only worth what you’re willing to sell it for.

01:09 Meet Stacy Stahl

02:37 The Idea That Started How He Asked

03:34 Going Viral Before “Going Viral” Was A Thing

05:32 How The Knot Came Into The Picture

09:38 The Lowball Offer, The Counter, And The Power Shift

16:04 Why She Started Her Second Company Anyway

20:06 When The Easy Path Disappears

20:45 Jumping From Digital To Product — On Purpose

22:57 Building A Business During COVID

23:49 The Pivot That Changed Everything

24:57 Breaking Into The Promotional Products World

26:59 Running A Business Without Burning Out

29:31 Why Simple, Profitable Businesses Win

32:01 Building Success And Bringing Others With Her

Kendra Bracken Ferguson built companies that invented the creator economy before Instagram and TikTok — and she tells the part founders unusually hide: when the shiny acquisition stops working, the earn-out math gets ugly, and you have to choose between protecting your title or protecting your team…

We get into trust as a system (including her very controversial co-founder test), buying a company back, building BrainTrust into a studio + fund backing Black beauty & wellness founders, and why corporate partners suddenly got nervous about “Black founder” the second it became inconvenient.

01:36 Meet Kendra Bracken Ferguson: Builder, Operator, Dealmaker
02:22 The Thanksgiving Idea That Sparked Digital Brand Architects
04:03 How DBA Helped Invent The Creator Economy Before Instagram
07:04 Knowing When To Walk Away—And Start Over
08:10 Why “Trust” Became The Non-Negotiable Business Principle
14:20 Inside The CAA Acquisition
18:36 When The Deal Looks Good—But The Reality Doesn’t
20:52 The Moment Everything Had To Change
21:20 Redefining Failure: Pivots, Pressure, And Perspective
22:41 Journaling, Self-Awareness, And Founder Survival Tools
24:32 Rebuilding With Intention: The Real BrainTrust Vision
25:12 From Agency To Studio To Fund
26:39 Corporate Partnerships, Power Dynamics, And Hard Truths
29:57 New Ventures, New Partners, And Building With Exit In Mind
35:39 From Hustle To Harmony: Success, Sleep, And The Next Chapter

In this solo episode, Carrie pulls back the curtain on what it actually takes to build an exit strategy for women founders—from choosing the right co-founder to expanding into brokerage without chasing growth for growth’s sake. She explains why so many women struggle with confidence during the exit process and how mindset, timing, and preparation directly impact business valuation.

You’ll also hear how the Whisper Group is evolving—from advisory to brokerage—and why selectivity is a competitive advantage when helping women navigate how to sell a company. If you’re building with an exit in mind or questioning whether you’re truly prepared for selling a business, this conversation will reshape how you think about female entrepreneurship and women founders exits.

00:00 Season 6 begins: why this chapter is different

00:43 The rise of women-owned businesses and the movement behind it

01:28 A major announcement: bringing on a co-founder

01:56 What actually matters when choosing the right co-founder

03:06 New upgrades, merch, and what’s evolving this season

03:23 Why we’re prioritizing in-person podcast conversations

03:43 Expanding into brokerage — with intention and restraint

05:12 The hidden cost of growth: expenses and pressure

05:41 Letting go of scarcity thinking while scaling

06:56 Why I’m genuinely excited about what’s ahead

In this episode, Nicole opens up about the hardest year of her life, balancing motherhood, money, and a messy business breakup, and how she found the strength to start over and build something entirely her own.


2:02 Nicole’s Journey Into Wealth Management  
5:37 Transitioning Into An Independent Advisory Firm  
6:27 Stepping Fully Into The Independent World  
7:34 Building A Niche Focused On Professional Athletes  
8:10 Supporting Exonerees With Their Financial Needs  
10:50 Considering Leaving The Firm For Personal Reasons  
12:33 Learning To Parent A Special Needs Child  
14:00 Concerns Over A Partner’s Financial Decisions  
17:40 Realizing It Was Time To Leave The Partnership  
18:40 Embracing Full Independence In Her Business  
20:00 Clients Rallying Behind Her During The Transition  
21:40 Negotiating Exit Terms With Her Business Partner  
24:28 Selling A Portion Of The Business  
25:07 Acquiring Additional Wealth Management Firms  
27:54 Lessons Learned From Business Partnerships  
29:50 The Importance Of Strong Financial Planning  

In this episode, Molly Nutt shares how she pulled off two very different exits, what she learned about selling potential vs. profit, and how to protect your relationships when business gets personal. If you’ve ever wondered how founders actually navigate the messy, emotional side of selling, this is the one to listen to.

  
2:34 Starting The CEO Society  
4:44 Creating A Friendship Clause In A Business Deal  
5:38 How Acorn Grew During The CEO Society Era  
6:24 Launching Oak’s Email Studio  
8:14 Splitting Brands To Stay Focused  
10:40 The Unexpected Offer To Buy Oaks  
11:20 Why Agencies Want To Acquire Email Agencies  
12:01 Trusting Your Gut During Negotiations  
12:44 The Challenge Of Untangling Finances  
15:30 Evaluating The True Value Of A New Brand  
16:45 Wrestling With Seller’s Remorse  
17:38 Selling Potential Versus Selling Historical Data  
19:12 Transitioning Into Life After The Sale  
20:25 Launching A Mentorship Program  
22:36 Advice For Women Building Their Businesses  
24:00 Why The Right Hire Changes Everything  
27:03 Details On The Growth Season Mentorship Program  

In this raw and unfiltered interview, Sharmin Ali shares how a chance encounter on a flight changed her life forever. From joining a startup that became a unicorn to surviving a cardiac arrest at 32, she reveals what founders never talk about: burnout, bad investor deals, and the price of ambition.

2:10 Choosing To Stop Chasing A Career At Google  
6:25 An Unexpected Job Offer Mid-Flight  
8:14 Learning The Basics Of Venture Capital  
10:05 Building Powerful Relationships In Pharma  
11:49 Closing Her First Million-Dollar Pilot Deal  
14:32 Launching Her YouTube Channel Back In 2014  
17:00 Why Timing And Vision Matter In Startup Success  
18:52 The Power Of Emotion In Marketing  
21:49 Facing Cardiac Arrest Again At Age 32  
24:14 Realizing Health Must Come First  
27:10 Why You Should “Date” Your Investor  
30:10 Learning To Let Go So The Business Can Grow  
32:44 What She Learned From Acquiring A Company  
34:41 Launching A Foundation To Support Entrepreneurs  
37:43 Honest Reflections On The Entrepreneurial Journey  
40:02 Key Advice For Aspiring Entrepreneurs  
42:04 Why Every Founder Needs A Therapist  

Angela Pointon opens up about what it’s really like to buy out your partners, take on debt, and bet on yourself when everything’s on the line. From the hardest conversations to the relief of letting go, this episode is about courage, burnout, and knowing when to walk away—on your own terms.

 
2:32 How 11Outof11 was born from freelancing burnout  
4:42 Leaving the commute and daycare guilt to go all-in on freelance  
7:13 Designing an agency with a future sale in mind  
9:50 The hardest step — deciding to buy out her partners  
13:06 Third-party valuation, bank loans, and emotional fallout  
15:32 Relief, confidence, and revenue skyrocketing post-buyout  
18:51 Why she chose to sell just one year later  
22:23 Choosing the right buyer and securing a 90-day transition  
24:45 No regrets and closing the deal during her son’s graduation week  
27:04 Fractional CMO life, building a mountain home, and family time  
30:18 Learning to slow down after witnessing friends survive cancer  
32:00 Why Angela’s real-world exit story matters  

Ever felt stuck running a business you no longer love—but you’re scared to let go? Meet Laura Roos, who sold her company without a broker, while pregnant, and turned the proceeds into her next seven-figure startup. This episode is messy, honest, and full of real talk about what it actually takes to walk away.



5:48 Why Selling the Business Felt Like a Dream Come True  
8:01 How the Company Grew Rapidly During the Pandemic  
9:59 Knowing It Was the Right Time to Sell  
11:30 Shifting Her Focus Into a New Business Venture  
14:10 Her Deep Obsession With Cannabis Dosing  
16:11 Making the Final Decision to Sell  
19:02 The First Meeting With a Business Broker  
21:19 The Game-Changing Email From a Potential Buyer  
22:57 The Hidden Challenges of Planning an Exit  
26:04 Why You Always Need Multiple Interested Buyers  
27:53 Mastering the Art of Negotiating Deal Terms  
30:22 Renegotiating Terms Even After the Deal Is Struck  
32:54 How She Created Predictability in Her Payments  
34:32 The Current Success of Mary and Jane  
37:25 The Hard Realities of Growing a Business  

What happens when the person running your company with you ends up buying it from you? Carey Linderman shares how she went from senior care to creating an entirely new category: the postpartum doula. And how she built a business that supported moms when no one else did, and why she ultimately decided to sell her company to her own #2.

 
2:10 Introducing Carey Linderman  
4:44 Moving From Senior Care Into Postpartum Doula Work  
7:01 Strengthening Family Bonding Through Postpartum Care  
8:11 Why Postpartum Support Matters More Than Ever  
9:45 Educating Families About True Postpartum Needs  
12:56 Creating a Comprehensive Doula Certification Course  
13:57 Building a Credible and Trusted Certification  
14:29 Bringing Experts Together to Elevate the Program  
15:12 Marketing the Doula Certification to the Right People  
16:03 Preparing Emotionally and Strategically to Sell the Business  
20:46 How an Employee Ended Up Buying the Business  
23:16 Financing the Business Purchase the Smart Way  
24:20 Carey’s Advice on Letting Go When It’s Time to Exit  

What do you do when you raise venture money… and then realize it’s not the right path? For Elle Hempen, co-founder of The Atlas, the answer was bold: sell just one year later.

 

In this episode, we talk about how a Google spreadsheet turned into a tech company, why she decided to skip the long VC grind, and how she negotiated an exit during the chaos of COVID. From pitching at Y Combinator while 8 months pregnant to getting a cold email from the exact company she dreamed of selling to, Elle’s story is packed with twists, hard choices, and the kind of honesty you rarely hear in startup land.

2:11 Why Valuing Early-Stage Tech Companies Is So Critical  
5:00 Building the Atlas Platform From a Real-World Problem  
6:34 Launching the First Version Back in 2016  
9:06 Creating a Strong, Scalable Data Infrastructure  
10:54 Deciding It Was Time to Fundraise for Growth  
12:29 Applying to Y Combinator to Fuel Expansion  
15:06 Fundraising in the Middle of a Market Crash  
17:01 Finding the Right Strategic Investor  
20:41 Soul-Searching to Determine the Company’s Direction  
23:12 Valuing the Business Based on Future Potential  
25:47 Celebrating a Rare and Remarkable Tech Achievement  
29:02 Reflecting on Five Years of Building and Learning  
30:40 Exploring What’s Next After the Exit  
32:23 The Unique Energy of Being an Entrepreneur  
34:40 Is an MBA Worth It for Founders?  
36:57 Aligning Education With Real Business Needs  

Michelle Caba, a former Wall Street professional, transformed a failing nail salon into a successful local business, eventually selling it with a considerable profit. Michelle discusses her journey from Wall Street to business ownership, emphasizing the importance of strategic planning, market research, and innovative services like CBD manicures. Now she helps other business transform digitally to achieve the same growth!


01:07 – Wall Street Dropout Buys a Nail Salon?!
02:38 – From Failing Salon to Local Empire
09:07 – CBD Manicures?! The Wild Strategy That Worked
15:28 – The Brutal Decision: Why She Finally Sold
21:25 – Life After Selling: From Salons to Consulting
24:14 – The Hard Truth Every Entrepreneur Needs to Hear
27:26 – Her Biggest Lesson (And What She’d Do Differently)

Julie Cole, co-founder of Mabel’s Labels, didn’t just survive the boys’ club of business—she doubled her valuation and sold to industry giant Avery. In this episode, she reveals the messy truth about co-founders, the brutal tricks buyers use to wear you down, and why staying passionate after the sale might be the ultimate win.

4:29 Turning a Simple Idea Into a Scalable Business  
6:56 Why Mental Health Support Matters for Founders  
7:30 Teaching the Market About a Product No One Knows Yet  
8:11 Leveraging Word of Mouth to Drive Early Growth  
10:12 The Real Challenges of Co-Founding With Multiple Partners  
13:08 Why Equity Decisions Matter So Much  
14:06 Recognizing When It’s Time for a Change  
15:01 The Unexpected Phone Call About an Acquisition  
16:14 Negotiating Hard to Protect the Brand and Staff  
19:34 The Exhaustion and Fatigue of Negotiation  
20:06 Staying Passionate About Your Brand Through It All  
21:02 Staying Actively Involved After the Acquisition  
24:25 Evolving the Business to Meet Changing Customer Needs  

Suzanne Shelton built one of the top sustainability communications agencies in the US from scratch, then shocked the experts by selling it for double her target price. In this episode, she spills the unfiltered truth: the gut-wrenching moments, the bets that almost broke her, and the secrets behind her once-in-a-lifetime exit.


4:11 Specializing in Energy and Environmental Marketing
5:49 Leading a $40 Million Environmental Campaign  
8:11 Why Companies Need Specialized Sustainability Consultants  
11:06 Payroll Struggles and Growing a Mission-Driven Business  
12:57 Staying Committed to Sustainability Through Every Challenge  
15:39 Her Deep Personal Connection to Sustainability Issues  
17:17 Why Sustainability Matters in Every Sales Conversation  
19:32 Making Business Decisions Based on Values Alignment  
21:46 The Power of Mission and Values in Choosing Partners  
24:34 The Hard Part: Losing Decision-Making Power  
26:17 Understanding the Timing and Process of Selling a Business  
28:49 Why Negotiating the LOI Is Absolutely Critical  
30:54 Working From Passion Instead of Necessity  

Ever wondered if you could risk it all—your savings, your sanity, your entire career—on a food you love? Erin Wade did just that. Fired from her law job and flat-out rejected by banks, she built a cult mac & cheese restaurant that broke every rule and every record. In this episode, Erin tells the unfiltered truth about betting everything, surviving the chaos, and what it really feels like to sell your “baby” to a VC-backed food giant.

  
3:05 The Struggle to Secure Funding for the Dream  
5:38 Friends Fly In From LA to Show Support  
8:53 Launch Day: Lines Down the Street  
10:41 Getting Early Product Feedback That Shaped the Menu  
12:54 Creating a Career and Life You Truly Love  
14:30 Building a Business Centered Around People  
16:30 The Decision to Buy Out His Business Partner  
18:01 Preparing the Next Generation for Leadership  
19:49 Finding Real Joy in Everyday Business Challenges  
22:50 Navigating Personal Struggles While Running a Company  
25:36 Passing the Torch After Selling the Business  
28:29 Rewriting the Book to Share a More Personal Story  
31:42 Loving the CEO Role and Leading With Purpose  

Ever wondered what really happens after you sell your business? Ashley Deland built and sold a top vegan restaurant—then watched the new owners burn it to the ground. In this raw, unfiltered conversation, Ashley and host Carrie Kerpen get brutally honest about burnout, regret, and the secrets nobody tells you about scaling and exiting. This episode is for anyone who thinks selling is the happy ending. Spoiler: it’s just the start of a whole new story.

 

2:04 Her Journey Through Burnout and Breaking Point  
6:09 Opening Karma — A New Vegan Restaurant Vision  
7:10 The Tough Early Challenges Every Restaurant Faces  
8:28 How She Funded Her Businesses Without Taking On Debt  
9:12 Pushing Past Doubt in the Entrepreneurial Journey  
10:56 Scaling the Restaurant With Intention and Strategy  
13:28 Selling the Restaurant and Building Community Along the Way  
15:02 Taking a Full Year Off After the Sale  
16:03 Why Emotional Readiness Matters Before an Exit  
19:01 Understanding How Much Control You Lose After Selling  
20:01 Becoming Truly Emotionally Ready to Exit  
21:06 Why Every Founder Needs an Exit Strategy  
22:13 Lessons Learned From All Her Past Business Chapters  
23:02 Launching Her New Book, *Unreserved*  

When everyone told Andrea to play it safe, she rewrote the rules and doubled her worth. In this episode, two powerhouse founders share the real story behind selling a business, risking everything, and turning partnership into a power move. Forget the “happily ever after” exit story—this is what actually happens when women decide to cash out and level up.

1:12 How She Knew It Was Time to Exit  
2:54 Scaling Fast Through Partnerships and Collaboration  
5:12 The Entrepreneurial Mindset: Risk, Grit, and Growth  
7:12 Why Chemistry Is Everything in an Acquisition  
8:39 Shared Vision: The Foundation of Strong Partnerships  
9:20 How Common Interests Create Stronger Collaboration  
10:47 Building Unshakeable Trust Through Hard Conversations  
11:14 Staying Grounded and Seeing the Bigger Picture  
12:57 A Moment of Gratitude for the Team Behind the Journey  

Colleen West hustled her way from a tiny condo and a fax machine to a multi-million dollar exit. In this raw, inspiring episode, she shares how heartbreak fueled her business empire, why she refused to play by corporate rules, and the bold moves that doubled her revenue during COVID. If you've ever felt stuck, this story will make you rethink what’s possible.

 

Chapters:

2:34 Colleen’s Journey as a Single Mother  
5:05 Turning a Job Into a Real Business Opportunity  
7:10 Balancing Motherhood and Entrepreneurship  
9:00 The Hard Realities of Growing a Business  
12:24 How Networking Became Her Growth Engine  
14:10 Moving Into Their First Dedicated Office Space  
16:36 Overcoming Barriers in the Medical Field  
20:10 Choosing Employees Over Easy Business Wins  
23:01 Getting Approached for Acquisition Before COVID  
25:52 How Revenue Doubled During the Pandemic  
29:01 How Court Reporters Adapted to Remote Work  
30:43 Why Trusted Advisors Are Essential  
34:06 Navigating Due Diligence With Confidence  
36:23 Stepping Into a Completely New Life  
38:19 Caring for Her Mother Through Illness  
40:50 Turning Dreams Into Reality Through Intention  

Joyce Marter didn’t just build a therapy business—she survived betrayal, took on millions in debt, and still managed a seven-figure exit. In this episode, she gets brutally honest about the moment her co-founder quit by email (and CC’d the staff), how she rebuilt from financial rock bottom, and the mindset shifts that helped her turn chaos into a multimillion-dollar win. If you've ever felt like you're drowning while everyone else thinks you're thriving—this one’s for you.

 

 
2:10 Why Destigmatizing Mental Health Is So Important  
6:11 Cash Flow Chaos During Rapid Growth  
7:30 When a Business Partner Resigns Out of Nowhere  
9:40 Why You Need a Pre-Dissolution Agreement  
10:44 Asking for Help During a Cash Flow Crisis  
12:56 How a CPA Revealed the Business’s True Value  
14:45 Overcoming a Deep Scarcity Mindset Around Money  
16:22 Practical Steps to Improve Cash Flow Fast  
19:01 Why Aligning With the Right Buyer Matters  
21:25 Choosing the Best Offer for Long-Term Success  
22:16 Standing Firm on Your Principles in Negotiations  
23:40 The Importance of Not Folding at the Final Hour  
27:43 Tools and Practices for Managing Money Stress  

Antonia helped build one of the most iconic period brands in the world. In this episode, she takes us inside the real, messy, deeply human journey of launching Thinx: from her pink pajama shame moment at 13 to raising millions, writing her own patent, and co-founding a brand that changed the way we talk about periods.

 

But that’s only the first half of the story.

 

She opens up about what it actually felt like to raise money, negotiate with strategic partners, and sit in rooms where you slowly lose control of the brand you built. What happens when you and your co-founders don’t want the same future? What do you do when the investors are offering the deal of a lifetime?

 

4:02 The Idea Behind Stain-Resistant Underwear  
6:48 The Girl Effect: Education and Empowerment  
9:02 Commitment and Teamwork in the Early Days  
10:37 Launching Their Kickstarter Campaign  
16:23 Landing a Partnership With a Major Company  
18:01 Creative Marketing Strategies That Built the Brand  
20:02 Why Clear, Consistent Communication Shapes a Brand  
22:45 Protecting Brand Ethos While Partnering Big  
25:26 The Struggle of Stylish but Painful Shoes  
27:21 Their Breakout Kickstarter Campaign for Shoes  
29:02 Why Co-Founder Communication Matters Most  
33:55 The Critical Importance of Getting Everything in Writing  
39:02 The Bittersweet Emotions Behind the Exit  
41:40 Reflecting on Whether the Journey Was Worth It  
43:14 Why Sharing Women’s Stories Matters  
46:03 How Intuition Often Guides Entrepreneurial Paths  
49:54 The Magical Encounter That Sparked a New Partnership  

She built a company from scratch to serve medically fragile children — and sold it for double her valuation.

In this powerful and emotional episode, Coco Sellman shares the full story behind founding her home healthcare agency inspired by her stepdaughter, scaling it to $7M in just 18 months, surviving the pandemic, navigating investors and partnerships, negotiating a merger, and finally landing the perfect exit with a major children’s hospital.

 

From starting without funding to surviving impossible cash flow gaps and sitting across from private equity in a room full of men — Coco breaks down what it really takes to exit on your terms. If you’re building with purpose but want a serious business outcome… this one is a must-listen.

 

2:34 Starting a Home Health Care Agency  
4:47 Spotting Big Market Opportunities in Health Care  
6:50 Building a Strong and Scalable Home Health Agency  
9:01 Why Proof of Concept Matters in This Industry  
10:36 Delivering Specialized Care for Fragile Patients  
12:11 How They Hire and Retain Exceptional Nurses  
14:01 The Decision to Bring On Investors  
18:10 Shifting Growth Strategies During the Pandemic  
19:56 Merging With Competitors to Stay Competitive  
22:01 Breaking Down How the Merger Was Structured  
24:01 The Major Challenges They Faced During the Merger  
27:22 Why Choosing the Right Partner Is Everything  
30:02 Winning a Medicaid Rate Increase  
32:13 Interest From Connecticut Children’s Hospital  
34:04 What Private Duty Nursing Really Involves  
35:38 Why Autonomy Matters So Much in Business  
39:32 The Role of Advocacy in Healthcare Pricing  

In this episode of The Exit Whisperer, we sit down with Ali von Paris, founder of Route One Apparel, a Maryland-themed clothing company that went from a viral college T-shirt idea to a self-funded powerhouse. Ali dives into the early hustle of building a business from scratch, learning e-commerce when it was still the wild west, scaling to 4,000+ SKUs, and eventually navigating the emotional and strategic complexities of selling her business.

 

If you’ve ever wondered what it’s like to exit a company you built from the ground up—or how to scale a community-rooted brand into a full-blown movement—this one’s for you.

 

2:12 How a Viral T-Shirt Sparked Ally’s Journey  
5:00 Launching Her Business With $12,000 in First-Day Sales  
6:51 Balancing College Life With Entrepreneurship  
9:30 Hiring Her First Employee and Building a Team  
13:15 Community Excitement and Deep Brand Connection  
14:50 Lessons Learned From Early Business Inefficiencies  
17:10 Why Finding the Right Office Space Matters  
18:50 Testing Market Interest Before Launching New Products  
21:00 Hitting Her Financial Stability Goals  
25:00 Figuring Out Who She Is Beyond the Business  
30:00 The Decision to Sell Her Company  
31:57 Exploring Options for Preserving Her Business Legacy  
34:01 Learning to Embrace a Life of Leisure  
36:00 Shifting From Productivity to Genuine Joy  
39:04 Discovering Her Personal Identity Beyond Entrepreneurship  

In this episode of The Exit Whisperer, Michelle Wahler shares the incredible 18-year journey of building Beyond Yoga—a body-positive, female-founded activewear brand that made comfort, inclusivity, and authenticity its mission from day one. From hand-illustrated T-shirts to a strategic, self-funded apparel company acquired by Levi Strauss & Co., Michelle unpacks every twist in her story: childhood influences, bootstrapping struggles, wholesale wins, emotional negotiations, and her mindset shift post-exit.

 

Whether you’re scaling your first business or considering your final chapter, this is a masterclass in leading with values and building a brand people love.

 

0:18 Michelle Sells Her Company  
2:01 Introducing Michelle’s Story  
3:40 Where Michelle’s Entrepreneurial Spark Came From  
5:47 Launching Her First Business, Unsweetened  
8:14 Building and Leading Beyond Yoga  
10:13 How Childhood Experiences Shaped Her Drive  
13:50 How An Investment Changed Everything  
17:00 Why Wholesale Partners Were Critical  
19:01 Building Relationships With the Early Sales Team  
20:37 A True Commitment to Real Women’s Bodies  
23:01 Why Fit and Fabric Quality Matter Most  
27:27 New Colors Coming for Their Signature Dye  
29:39 Exploring a Potential Partnership With the CFO  
32:30 Choosing Steady Growth Over Short-Term Profit  
35:06 Why Avoiding Excess Inventory Is Essential  
36:58 Teamwork That Got Them Through Tough Negotiations  
39:34 Aligning Brand Values With the Right Partners  
41:46 Navigating the Transition Out of the CEO Role  
44:40 Embracing a New Chapter in Life  

Carrie sits down with Jennifer Vazquez, a single mother who overcame bankruptcy and the failure of her first business to build and sell a series of successful childcare centers.   Jennifer shares her journey of acquiring, scaling, and eventually selling three childcare centers for double their valuation. She discusses key strategies such as seller financing, and the benefits of buying existing businesses over starting from scratch.   Jennifer also delves into her transition from running childcare centers to her current role as an EOS coach, helping other entrepreneurs achieve success. Her story is filled with persistence, grit, and invaluable insights for anyone navigating the entrepreneurial landscape.     2:20 Why Buying an Existing Business Can Be a Smart Move  
5:29 Seller Financing Explained in Simple Terms  
7:11 Negotiating Back Rent With the Landlord  
9:01 Searching for Strong Standalone Business Opportunities  
10:50 Acquiring the Building Through a REIT  
13:12 Taking Bold Risks by Expanding to Multiple Locations  
15:14 Using EOS to Run and Scale the Business  
17:44 Why She Decided to Sell After Major Success  
19:53 Hitting Their Best Year Ever in 2021  
24:11 Keeping Quality High All the Way to Closing  
26:22 How EOS Coaching Transforms Businesses  
28:00 Shifting From Day-to-Day Operator to Visionary  
30:02 The Big Advantages of Buying an Existing Business  

Miren Oca, the founder of Ocaquatics Swim School, a successful swim school business she started at 22 years old after becoming pregnant in college. Miren shares her inspiring journey from teaching swimming lessons to building a business with 165 employees, 5 locations, and 6,500 weekly swimming lessons.

She discusses her focus on environmental and social responsibility, becoming a certified B Corporation, and the unique exit strategy she implemented using an Employee Ownership Trust (EOT), ensuring her business’s legacy and continuing benefits for her employees.

 

Miren explains the challenges and successes in setting up the EOT, why it was the best choice for preserving her company’s values, and the profound satisfaction she has experienced through this exit route.

 

2:10 Miren Oka Shares the Vision Behind Her Employee Trust  
3:01 Starting a Business at Just 19 Years Old  
5:02 How Books Helped Miren Become an Entrepreneur  
5:47 Miren’s Passion for Life-Saving, Purpose-Driven Work  
6:20 The Journey to Building an Indoor Pool  
6:57 Teaching 6,500 Swimming Lessons Every Week  
7:34 Prioritizing Team Growth, Happiness, and Stability  
11:08 Employees Returning as Co-Owners  
12:41 Exploring Different Employee Ownership Models  
14:30 Discovering the Employee Ownership Trust Structure  
15:01 How Co-Owners Earn Their Shares Through Time  
16:57 Why She Chose Seller Financing for the Transition  
18:01 Teaching Employees to Think Like Owners  
19:15 Building a True Culture of Ownership  
20:38 The Joy of Transitioning to Employee Ownership  
21:59 Why Young Team Members Matter So Much  
23:41 The Big Benefits of Seller Financing  
24:29 Other Options for Transitioning a Business  
25:39 Creating an Inspiring Legacy for Future Generations  

Carrie introduces Susan Latremoille, founder of Next Chapter Lifestyle Advisors. Susan shares her journey from building a successful financial advisory practice to selling it at a premium valuation.   With over 40 years of experience, Susan transitioned from Merrill Lynch to entrepreneurship, ultimately exiting her company in 2019. She discusses the importance of trust and team development in her business, as well as the process of preparing for and executing a successful exit.   She also works with financial advisors to enhance their client relationships beyond just financial planning.     2:20 Susan’s Path Into Financial Services  
5:51 Moving Into an Independent Financial Practice  
6:49 Shifting to Strategic, High-Level Board Meetings  
8:00 Why Independent Investment Choices Matter  
9:36 Building Client Trust From the Ground Up  
12:14 Preparing Entrepreneurs for Business Succession  
13:20 How to Find the Right Successor  
14:05 Why the Age Gap Matters in Succession Planning  
16:01 Transitioning Clients Smoothly to New Leadership  
18:24 Formalizing a Seamless Business Transition Process  
20:10 Why So Many Business Owners Regret Their Sale  
20:50 Starting Next Chapter Lifestyle Advisors  
24:09 The Importance of Personal Planning Before an Exit  
26:00 How to Connect With Next Chapter Advisors    

 

At just 26, Susan took a leap — launching News Generation with the backing of her family and a single client’s nudge. What followed was a two-decade journey building a niche agency in radio media relations, where she prioritized culture, steady growth, and real relationships. In this episode, she opens up about the real emotions behind selling a business, why she started thinking about exiting around age 50, and how she navigated the unexpected curveball of selling during a pandemic. Susan also shares what really mattered in the deal (spoiler: it wasn’t just the money), why her office space and team were non-negotiables, and how she’s now using her experience to guide other women founders.

 

This is a story about knowing your worth, leaving with integrity, and designing what’s next — on your own terms.

 

2:31 How She Launched the News Generation Agency  
5:51 Making Smart Decisions About Hiring and Equity  
7:44 Why She Only Needed $14,530 for the First 90 Days  
9:59 How Those First 90 Days Became Her Catapult to Success  
12:24 Selling the Business in 2020 After Major Growth  
14:23 The Emotional Low Point Before the Sale  
16:09 The First Acquisition Approach Back in 2018  
19:01 Gaining Confidence by Testing Her Market Value  
21:27 Why She Decided to Skip Using a Broker  
23:00 Signing All the Paperwork in the Middle of COVID  
25:00 Celebrating the Sale With a Meaningful Dinner  
28:26 The Acquisition, Rebrand, and Name Change  
31:37 Teaching and Empowering Women in Leadership  

She Was Told “You Can’t Be a Good Mom and Build a Company” — So She Proved Them Wrong

 

Michele discusses her successful career as an entrepreneur who managed to maintain a work-life balance while building and eventually selling her global translation business.

 

In an engaging conversation with Carrie, Michele shares insights from her journey, including the initial struggles, the importance of offloading responsibilities, and the process of scaling. She emphasizes the significance of setting personal and business goals, handling the transition after a business exit, and finding new purposes.

 

The episode provides valuable advice for women entrepreneurs on preparing for an exit and determining their worth outside their business.

 

1:58 Finding a Healthy Balance Between Work and Life  
5:08 The Moment She Realized She’d Been “Fired” From Her Own Life  
7:02 Understanding That *You* Are Often the Biggest Roadblock  
10:14 Why Every Founder Must Build Repeatable Engines  
12:40 The Struggle of Managing Freelance Availability  
15:30 The Real Reasons She Considered Selling Her Business  
18:49 Transitioning Out of Tech Into New Opportunities  
20:20 How Mindset Shapes Business Growth  
22:01 Why the M&A Market Is Tough for Small Businesses  
25:12 Exploring Identity, Freedom, and What Comes Next  
27:30 Choosing Your Own Value—Not What Others Assign  
29:01 Encouragement to Name Your Number and Own Your Exit  

Kelly shares her story, from her early days of recognizing her entrepreneurial spirit to the founding of her company, Send Ribbon.   She discusses her tech startup background, the challenges of personalized corporate gifting, and how her experience inspired her business idea.   She shares insights into her strategic methods for launching the business, overcoming financial constraints, and the pivotal moments that led to the company's growth. Kelly also details her personal life sacrifices, the importance of networking, and her eventual acquihire by Urban Stems during the pandemic.     
1:01 Kelly’s Path to Becoming an Entrepreneur  
5:55 Taking Big Risks in the Startup World  
8:34 Managing Money Through Early Startup Struggles  
10:51 Cutting Costs to Keep the Business Alive  
13:03 Lessons Learned From Buyers at Ralph Lauren  
15:02 Launching the Business Just in Time for Mother’s Day  
17:51 Prioritizing Customer Needs Over Vanity Metrics  
20:10 Reconnecting With the Founder of UrbanStems  
22:03 The First Conversation That Sparked an Acquisition  
24:08 The Email That Confirmed UrbanStems’ Interest  
26:12 Moving to DoorDash to Build Community  
28:01 What an Acquihire Really Looks Like  
31:48 How the DoorDash IPO Shaped the Experience  
33:40 Why Resources Matter So Much in an Acquihire  
37:00 The Emotional Challenge of Letting Go of Ownership  
38:38 The Regrets That Can Come After Selling  
40:50 Long-Term Career Paths After an Acquihire  
42:21 Spending the Holidays With the People Who Matter  

 

Anne Mahlum, the founder of SolidCore, shares her journey from being a waitress in North Dakota to negotiating a major company sale.   Anne shares her incredible story of founding SolidCore with $175,000 of her own savings after initially working in nonprofits and creating a running club for a homeless shelter. She discusses the challenges she faced, including navigating contentious business relationships and securing funding, while highlighting the importance of an unwavering belief in oneself.   Discover how Anne turned her passion for fitness and community building into a $100 million success story, the strategic decisions she made during the COVID-19 pandemic, and her ultimate exit strategy.   Anne also sheds light on her financial philosophy, the impact of her upbringing, and the significance of achieving a nine-figure exit.     00:33 Introducing Anne Mahlum: From Waitress to Entrepreneur 4:54 The Power of Believing in Yourself  
7:00 Stepping Into the Next Chapter of Her Life  
10:06 Overcoming Deep Self-Doubt as an Entrepreneur  
11:52 Navigating a Tough Relationship With a Business Partner  
14:00 Becoming Intentional With Every Spending Decision  
15:57 Scaling From 6 to 25 Studios  
18:00 Why Control Is Everything in Dealmaking  
19:36 Expanding at Lightning Speed to 50 Studios  
22:59 A CEO’s True Risk Tolerance in a Crisis  
25:00 Negotiating With Landlords to Keep the Business Alive  
27:00 Expanding Into Red States During the Pandemic  
28:38 Promoting Brian to CEO  
30:37 How She Achieved a $100 Million Exit  
32:54 Why Rewarding Employees Matters More Than Ever  
34:33 The Case for Not Starving Founders  
36:20 Seeing Money as a Trophy for Value Creation  
39:31 Aligning Your Skills With the Right Opportunities  

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  

 

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      

 

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    

 

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  

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  

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  

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  

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  

 

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