Overview of Call Her Daddy with Devon and Sydney Carlson
Alex Cooper sits down with sisters, best friends, and business partners Devon and Sydney Carlson for a candid, funny, and surprisingly vulnerable conversation about family dynamics, their 10-year journey building Wildflower Cases, dating after breakups, and how their relationship as sisters has evolved through success, conflict, and growth. The episode blends sisterly chaos, business origin-story storytelling, and honest reflections on love, jealousy, loyalty, and healing.
Main Topics Discussed
Sisterhood and Their Relationship Dynamic
- Devon and Sydney describe themselves as unusually close siblings who have mostly avoided major fights growing up.
- Their conflicts are often over clothes, borrowing each other’s things, or small sisterly annoyances.
- They share the same friend group and see each other almost every day, which makes their bond feel more like a built-in friendship.
- A difficult relationship Sydney was in created distance between them for a while, but it ultimately made Devon realize how much she didn’t want to lose that closeness.
The Origin Story of Wildflower Cases
- Wildflower Cases began 10 years ago when their mom made a custom phone case for Sydney using a clear case, fabric, and studs.
- Friends at school and strangers at the mall started asking where the cases came from.
- The turning point came when Miley Cyrus noticed Sydney’s case and encouraged them to start a business.
- Miley tweeted about the cases, which created immediate attention and demand.
- Their family went all-in:
- their dad helped build the website,
- they sold their house to fund the business,
- and the family even lived with their grandparents while running the company from home for the first several years.
- They emphasize that the business was never originally intended to become a company—it grew organically from a DIY idea.
Family, Work, and Pressure
- The sisters talk about how the business brought their family closer and created a sense of shared responsibility.
- They also acknowledge the pressure and weirdness of starting a business young, especially at a time when social media entrepreneurship wasn’t normalized.
- Sydney reflects on feeling embarrassed at times because people around her didn’t understand why she wasn’t following the traditional path.
- Now, both feel grateful and say they’re finally at a place where they can enjoy more freedom because they’ve built a trusted team.
Dating and Relationship Talk
Devon’s Dating Life
- Devon shares that she is currently seeing someone exclusively.
- After leaving a long, public relationship, she went through a “wild” single phase where she said yes to everything and made up for lost time.
- She describes herself as more of a relationship person, but only after a period of exploring and enjoying being single.
- She values a partner who is witty, confident, and comfortable being themselves.
- Devon also admits she can be very direct and sometimes “tests” guys, which she finds entertaining.
Sydney’s Dating Style
- Sydney says she’s been on only one official date in her life.
- She tends to become interested in someone after being friends first, rather than through traditional dating.
- She is drawn to men who are funny, unique-looking, and a little unconventional.
- She says she’s most attracted to people with strong personality and confidence, especially when they’re not trying too hard.
Cheating, Recovery, and Emotional Fallout
- Sydney opens up about a deeply unhealthy, intense relationship she was in from her late teens into her early 20s.
- She describes it as consuming, emotionally draining, and tied to a period where she isolated herself from friends and family.
- The relationship involved addiction and infidelity, and she says it taught her that love should not require enduring constant pain.
- Devon was deeply affected by the relationship too, especially because it pulled Sydney away from the sister bond.
- When that relationship ended, Devon made a point of bringing Sydney back into their friend group and helping her reconnect with healthier relationships.
- Sydney says the breakup ultimately saved her and helped her find her way back to herself.
Funny and Notable Moments
“Which Sister Is More Likely To…”
Alex plays a sister-themed game that reveals:
- Sydney is more likely to be the favorite child.
- Sydney is more likely to take clothes without asking.
- Devon is more likely to post drunk on Instagram.
- Devon is more likely to text an ex when drunk.
- Sydney is more likely to get kicked out of a club.
- Both agree neither of them would be likely to cheat in a relationship.
- Both say they’re too jealous for an open relationship.
A Memorable Bad-Date-That-Worked-Out Story
- Devon tells a story about a disastrous New York date:
- the guy was late,
- she got annoyed and went to eat without him,
- he arrived even later,
- his car got towed,
- and she roasted him the entire time.
- Despite all that, they ended up sleeping together and had a great night.
- She jokes that she paid for dinner, handled the chaos, and still gave him “the best sex of his life.”
- The story becomes a perfect example of her blunt, confrontational, funny dating style.
Key Takeaways
- Their sisterhood is the core of everything: Even when they drifted, they eventually came back stronger.
- Wildflower Cases is a true family-built success story: It started as a DIY project and became a real business because of momentum, support, and hard work.
- Both sisters have very different dating energies:
- Devon is more extroverted and relationship-oriented after a wild single phase.
- Sydney is selective, friend-first, and more cautious about dating.
- They’re both brutally honest about relationships: especially around red flags, cheating, and the ways people can lose themselves in toxic dynamics.
- The episode is equal parts funny and sincere: sister banter sits right next to real emotional honesty.
Overall Impression
This episode is a mix of chaotic sibling chemistry, entrepreneurial nostalgia, and hard-earned relationship wisdom. Devon and Sydney Carlson come off as funny, self-aware, and deeply loyal to each other, while also being refreshingly honest about the messier parts of love, family, and growing up in the public eye.