Serial Entrepreneurs and Sisters Who Created Success

5 Minutes Read

Episode 113

Are you a serial entrepreneur? Perhaps you want to create multiple successful businesses? You are in for a treat!

Today we welcome a dynamic duo, Courtney Hopper and Dana Kadwell. These powerhouse sisters are successful serial entrepreneurs based out of Raleigh, North Carolina.

Together, over the past 14 years, they have built and operated multiple successful businesses. These include The Bradford Wedding & Event Venue, C&D Events, Bushel & Peck Floral Design, and Anthem House Events. They are also hosts of their podcast show called Hustle & Gather to top it all off.

Starting from ordinary, they paved their way by sheer grit and tenacity, splashed with some therapy and coffee along the way. They are on a mission to inspire others to take giant leaps, dream big dreams, and create outstanding teams that grow profits and an enjoyable but productive culture within the business.

Here are three reasons why you should listen to the full episode:

  • Discover Courtney and Dana’s passion story and their journey from teachers to successful serial entrepreneurs.
  • They share how they created multiple successful businesses in one major niche category.
  • Find out about their journey of challenges and triumphs as a dynamic sister duo in their business.

Episode Highlights

Courtney and Dana's background

    • Dana has a Bachelor of Science in Chemistry and Math.
    • Courtney has a Bachelor of Science in Biology and Chemistry.
    • When they started their first business, they were still teaching.
    • They discovered a love for the events industry and knew that this was the path that they needed to pursue.

The start of the journey to being serial entrepreneurs

    • Their business story started when they looked for a venue for Dana’s wedding.
    • They both got married very young, having many friends at this point.
    • They needed a space for 200 plus people, but there wasn’t a space like this in North Carolina.
    • They thought it would be a fun idea to open their event venue and sketch their concept on a napkin while sitting at a café.

Becoming event planners

    • Neither of them knew anything about weddings other than planning their own.
    • So they decided to become event planners as a form of market research.
    • To build the best venues, they planned to first work in other venues to figure out what works and doesn’t work.

Starting C&D Events

    • Dana admits that she and her sister are always coming up with ideas that never end up materializing, so she didn’t overthink it.
    • The next day, Courtney called Dana and said she spoke to a childhood friend who was getting married and that they’d plan the wedding.
    • They were officially going to start C&D Events.

Event planning for free

    • They went ahead and planned the wedding successfully.
    • They did a couple of others for free to gain experience.
    • After getting their feet wet as event planning, they realized that they liked it.

Their first gig off Craigslist

    • They started by advertising on Craigslist.
    • They secured their first gig and charged $250.
    • It was 100 miles away, and they admit that it was the most challenging $250 they had ever earned.

Being recommended

    • The good thing about this first gig was collaborating with a catering friend of theirs.
    • It was his first gig too.
    • It was far from perfect, but they realized that they had made a good team.
    • He started recommending them, and C&D Events began to gain traction.

Going all in

    • They were both still teaching in 2010, finding themselves doing things halfway and close to burnout.
    • The business was operating for three years, and they had reached the point where it was more than a hobby.
    • A decision needed to be made to go all in and put all their eggs in this basket.
    • They ended up going from 12 weddings in a year to 37 weddings.

Buying land for a venue

    • With enough money in the bank, they decided to buy some land for the venue.
    • They found the perfect piece of land, and it was perfect timing because it was the end of the recession when no one was buying anything.
    • They did their due diligence by rezoning the property, and it was approved.

Getting financing was a struggle

    • Once rezoning was approved, it took them another six months to get financing.
    • They started construction, and things got hard for them.
    • They were supposed to get a bank loan in the middle of it, but it fell through.
    • No one would take them on because they felt it was too risky.

Running out of money

    • So there they were with a halfway-built venue, and they had run out of money.
    • They cashed out everything that they had and owned.
    • This included every retirement account and maxing out all credit cards.
    • Their pure belief in their dream kept them going, even when things got tough.

Networking and building relationships

    • The catalyst for their customer acquisition was networking.
    • They started getting their face in front of as many people as possible and planned strategic meetings.
    • The focus was on a better customer experience and practicing faster response times.
    • They focussed on relationships and poured into them.


    • Courtney and Dana have a couple of planners that work for them.
    • They also use contract cleaners for events.
    • At one point, Courtney had 27 weddings, and Dana had 29.
    • At the same time, they also had 40 floral events.
    • They divided and conquered.

Keeping it lean

    • Courtney and Dana had two contract employees for C&D Events.
    • They have kept things very lean as they had no money.
    • Everything was going back into the business.

Their love for the niche

    • The community and camaraderie.
    • The opportunity to be a part of someone’s happiest day.
    • Being surrounded by some of the most creative, kindest, and innovative people.
    • They feel inspired every single day.
    • It’s not just about the money, but the passion and fulfillment.

The sister-business-partner dynamic

    • Courtney says that Dana’s best and worst thing is she cannot chill; she goes all out and is locked in.
    • Dana says that her sister is a great visionary and a lot more optimistic than she is, but her technological illiteracy drives her nuts.

How their marketing has evolved

    • It started with Craigslist and networking.
    • Realizing that marketing was not their strength, they’ve hired a full-time employee to manage this for them.
      Understanding their strengths and weaknesses has been an essential part of their journey and has helped them define their roles.

Therapy and an intentional reset

    • Transparency has been a crucial part of their story.
    • Stress, lack of sleep, no money, and tension led to many hurt feelings and loss of trust.
    • They ended up going for couples therapy to do an intention reset.
    • They’ve been best friends their entire life, and it’s hard when you get to a place when you don’t like one another, and it was important to get back there.

How do they want to be remembered?

    • Dana wants to be remembered for being a kind person.
    • Courtney wants to be remembered for being motivational and inspiring.

3 Powerful Quotes from this Episode

08:48 – “So we were halfway built, and we ran out of money, and so we cashed out everything we had, like everything we owned, every retirement account. We maxed out every single credit card, I mean, we would go to Home Depot and Lowe’s, and you’d have like $30 worth of stuff. And you’d be like, try this credit card, and it would decline. Try this credit card; it declined. $5 on here, $15 on here, and then I have $5 in quarters.”

10:24 – “When you’re talking about an event, it’s a team, I mean, you live and die by your team, like you’re in the trenches together. Those relationships are stronger than lifelong ones because you’ve been through some hell together.”

30:35 – “Transparency is an important part of our story. We went to couples therapy to get down to the root of why we were feeling what we were feeling.”

About Courtney and Dana

Courtney Hopper and Dana Kadwell are a dynamic sister duo who have become serial entrepreneurs in a particular niche category. Over the last 14 years, they have built multiple successful businesses, and it has not come without sacrifice, tenacity, and grit.

They are on a mission to inspire others to take big leaps and to have big dreams, just like they did. Their journey started with a sketch on a napkin, and this was the beautiful journey of serial entrepreneurship as sisters.

Alongside their two primary businesses, The Bradford and C&D Events, they have also started their podcast called Hustle & Gather this year, inspiring the everyday entrepreneur. They chat with different entrepreneurs from all over the world, learning their story and their entrepreneurship journey.

They have also just launched their new Luxury Event Planning Company, Anthem House, specializing in high-end multi-day events.

Connect with the Dynamic Serial Entrepreneurs

The Bradford

Hustle and Gather

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Thanks for listening,


Picture of Darrell Evans

Darrell Evans

Darrell Evans is a serial entrepreneur, investor, and Co-founder/CEO of Yokel Local Digital Marketing Agency. He and his teams have helped businesses generate over $300M+ in revenue online. Every month, he leads virtual workshops teaching actionable strategies and tips from his experience helping companies market, grow, and scale.