New Podcast “Successfully Screwed” Explores Ways to Learn from your Mistakes

Sometimes screw-ups make for great fodder.

The seemingly perfect Tinder match who in-person caused you to deploy your seldom-used escape plan, or kids having an extra teaspoon of sugar past a particular time causing them to scale the walls to avoid bedtime, later make for fun anecdotes.

Less commonly shared are business setbacks, especially when it comes to start ups. But Sara Rosenberg and Ashley Owens plan to change that by taking an unfiltered look at failure during their “Successfully Screwed” podcast, which discusses the mistakes, screw-ups, and bad decisions everyone makes in the course of their careers. 

The podcast launched on June 4 at Headroom in Wayne.

During the weekly 30-minute episodes, guests share their failures and what they subsequently learned. “Successfully Screwed” is Owens’s idea, but she’s quick to point out that the execution is all Rosenberg, who handles the back-end, while Owens focuses on editing.

While launching a podcast is a lot of work, Rosenberg and Owens were quick to make it a reality. “Within a week, Sara had the name of the website, the documentation, the images, the content, and the social media. That’s the dynamic [we] have. We get things done and we triple down on our strengths,” says Owens.

Rosenberg and Owens realize that focusing on what would be considered failures is a decidedly different approach than the usually motivational tones of podcasts. “This is going to be good, juicy, entertaining information,” says Owens. “Selfishly, I get to learn directly from my guests. It’s a way for me to take the advice and apply it to my business.”

Throughout the podcasts, both hosts present their own candid points of view and admit that it’s okay to cringe, laugh or experience Schadenfreude when listening.

The podcast has created an offshoot via the Successfully Screwed Podcast Entrepreneur Community on Facebook, focused on making businesses better by providing support, resources and a place for discussion. “It’s a safe space to talk about things you wouldn’t put on your business’ social media. We want to break down the taboo,” says Rosenberg.

Rosenberg and Owens have plenty of material from their own careers, but prefer to keep the focus on guests. Rosenberg, a Glenside resident, never quite fit in with her upbringing and left to pursue a career in finance. Finding the lifestyle wasn’t conducive to a family, she started her own businesses. “Some were more successful than others,” she admits.

In March 2014 she launched PowerMatch. Born of a dislike of networking events and introverted tendencies, she formed PowerMatch to help professionals of all types build long-lasting business relationships. The formula relies on some level of intention on both parties’ parts, and consists of meaningful connections. Rosenberg speeds up the process by identifying a client’s needs and the reason for networking.

Owens, a West Philadelphia resident, started her career as a personal and executive assistant to two celebrities in New York City. She moved around a lot before finding herself selling custom software, but found it unfulfilling. Last year, she connected with Rosenberg via PowerMatch.

Both Owens and Rosenberg realize that by launching a podcast that relies on people sharing their setbacks, they’re opening themselves up to failure. Still, they believe in the model—and the process of failing. “If you aren’t failing, you aren’t doing anything of value in your life,” says Rosenberg. “Failing is how you know you’re moving forward. If you’re playing it safe, you’re stagnant.”

The message of “Successfully Screwed” is simple, if unusual: Everyone fails—it’s what you do after that matters.