
Hustle Before You're Ready with Haley Thams
In this episode of Keep Hustling, host Aaron Gordon welcomes the first second-generation guest in the show's history. Haley Thams is the owner and CEO of Plimsoll Media, the agency behind the video and social content for this podcast, and she is the daughter of Todd Thams from episode 65. She bought the agency from Bradley Flowers at twenty one, fresh out of college, having never worked a corporate job in her life. Her reasoning was that if she took a nine to five first she would never find her way back to entrepreneurship, so she chose the scarier option while she was young enough to recover from it. Aaron pushes on why someone already running a company would add teaching early morning cycle classes, and the answer turns out to be about isolation rather than ambition. The conversation then gets unusually honest. Aaron gives her live on-air criticism about undercharging for work she keeps absorbing, she defends why she does it, and neither of them backs down. She closes with the line she lives by: show up before you're ready. Get To Know Haley Thams Haley Thams is a Midwesterner with a passion for content, and the owner and CEO of Plimsoll Media. Whether a brand is starting from scratch or already has a built following, she makes the work personal. She grew up in Iowa and is a graduate of Iowa State University's Greenlee School of Journalism and Communication, with a degree in Public Relations and Business Marketing. Some of her proudest work at Iowa State was writing for the Iowa State Daily, building her own online portfolio, and working as an intern. She finished her degree a semester early in December 2022, and the next month, at twenty one, she bought Plimsoll Media from Bradley Flowers, before she had ever worked a corporate job. Nearly four years later she runs the agency from Chicago. Plimsoll handles strategy-led media days, short-form and long-form capture, content systems and distribution, workflow automation, and ongoing advisory built on real performance data. Among its clients, Plimsoll produces the video and social content for this podcast and for Aaron's NY Risk Advisor channels. Since May 2025 she has also taught cycle classes at SALT Fitness Chicago, where her TikTok, @haley_thams, has built a following of more than 3,000 riders and fans. Haley is the first second-generation guest in Keep Hustling history. Her father, Todd Thams, is episode 65, Maintaining The Hustle. Bradley Flowers, who founded her company and later sold it to her, is episode 4, Finding Freedom Through The Hustle. Website - https://plimsollmedia.com/ LinkedIn - https://www.linkedin.com/in/haley-thams/ Instagram - https://www.instagram.com/plimsollmedia/ Tik Tok (Plimsoll Media) - https://www.tiktok.com/@plimsollmedia Tik Tok (Haley) - https://www.tiktok.com/@haley_thams Youtube - Facebook - 3 Key Listener Takeaways 1. Show up before you're ready. Haley's closing line is the whole episode in five words. She is candid that she carries imposter syndrome, does not know everything, and is not the best at any one thing, but she shows up present and ready to work anyway. The alternative, waiting until you feel qualified, is how people end up twenty years down the road regretting what they never tried. 2. Most people will give you a chance. The job is not to waste it. Aaron reveals a phone call that happened before the sale, where Bradley told him he was fairly sure Haley would figure it out. The client base stayed because they trusted the handoff. Aaron's point to any young person listening is that the chance is usually there for the taking, and the fear of being too young or not being taken seriously is mostly self-inflicted. 3. Saying I will figure it out is good business. Doing it for free is not. This is the sharpest exchange in the episode. Haley will learn anything a client needs rather than hand them off, which is exactly why she keeps clients. Aaron tells her live on air that she is terrible at pricing that work, and that doubling a workload without adjusting the fee is bad hustle. She pushes back that she does not want to charge people who believed in her early. Both positions are worth hearing. Show Overview 00:00 The first multi-generational guest in show history 01:26 Who Haley is and what Plimsoll Media does 01:52 Why add spin instructing on top of running a company 02:10 The isolation nobody warns you about with remote work 03:16 Moving to Chicago knowing exactly one person 04:22 Not joining the class, leading it 05:26 Why this was never about a second paycheck 07:07 Buying a business at twenty one 07:23 The deal with Bradley Flowers, and no corporate job ever 08:42 If I take the nine to five, I never come back 09:24 Should more young people take the swing 10:11 No systems, no processes, no idea how the money worked 11:00 The people who quit just short of the goal 11:29 The phone call Bradley made before the sale 12:28 Most people will give you a chance, do not blow it 13:39 The three clients who stayed through four years of figuring it out 14:20 The client who almost left for a bigger agency 15:46 Saying no versus saying I will figure it out 16:12 Going behind the curtain on what she charges 17:03 You doubled the workload and never raised the price 17:23 Why she will not bill the people who believed in her first 18:34 Being Todd's daughter at an industry conference 19:13 Why she bought a business instead of starting one 21:13 It is not what you know, it is who you know 21:47 Taking Plimsoll outside the insurance industry 23:41 Show up before you're ready, and a line from Mark Twain
















