139. Would You Rather? Entrepreneur Edition 🍻

Holly Silva
Mar 13
3 min read

After what felt like a full-blown battle with technology, we finally made it happen — and honestly, that chaotic start was the perfect kickoff for this episode of Hustled Up After Hours! In true after-hours fashion, we settled in with our drinks, embraced the madness, and played a very unfiltered round of Would You Rather? – Entrepreneur Edition. What started as a fun interactive game quickly turned into a hilarious, slightly unhinged look into the real thoughts business owners have but do not always say out loud.

Throughout this episode, we worked our way through categories like chaotic entrepreneur life, cleaning industry-specific scenarios, business growth situations, and completely ridiculous business dilemmas. We debated everything from whether we would rather lose Wi-Fi or coffee, clean a haunted house or the wrong house, deal with overstaffing or understaffing, and whether we would rather lose our CRM data or face a credit card software hack. Some of the questions were funny, some were painfully realistic, and a few honestly unlocked brand new fears we reeeeaaally did not need. As always, though, those kinds of conversations led us into deeper reflections about leadership, company culture, client relationships, growth, and what it really takes to run a service-based business.

One of our favorite parts of this episode was how interactive it became. Our live audience jumped into the comments, played along with us, and made the whole conversation even more fun! If you joined us: thank you! Your support means the world. 🫶 We also found ourselves sharing real behind-the-scenes thoughts about hiring, client retention, scaling, reputation, and the hard decisions that come with entrepreneurship. This episode is definitely one of those lighter, laugh-out-loud conversations, but underneath the humor is a whoooole lot of honesty about the realities of building a business. If you have ever had to make a tough call, manage a stressful client, laugh through a business disaster, or just wonder how other entrepreneurs think through messy situations, this one is for you.

In this episode, we talked about:

Our very rocky start thanks to livestream tech issues 🫠
What Hustled Up After Hours is and why we love this format
A full game of Would You Rather? – Entrepreneur Edition
Chaotic business owner scenarios and client horror stories
Cleaning company-specific dilemmas
Business growth choices involving revenue, staffing, and scaling
Ridiculous but strangely realistic entrepreneurship situations
Our live audience’s answers and reactions throughout the episode

A few themes that came up:

The difference between growth that is exciting and growth that is chaotic
Why reputation and trust matter so much in business
How company culture can make or break a team
The balancing act between quality of life and building something bigger
Why entrepreneurship requires humor, resilience, and a little bit of delusion

Listen here:

✨ Spotify: https://open.spotify.com/episode/1YmaSjiHR84pK2YZfGJIl8?si=D-cAr5GmTI2Olbrlm_rDCg

✨ Apple Podcasts: https://podcasts.apple.com/us/podcast/139-would-you-rather-entrepreneur-edition/id1619723852?i=1000754431542 ✨ YouTube: https://youtu.be/nZIvX9qxSD8?si=QOW0HSiN6rhQAwCC

✨ Other platforms: https://creators.spotify.com/pod/profile/hustledup/episodes/139--Would-You-Rather---Entrepreneur-Edition-e3g65l1

https://www.youtube.com/watch?v=nZIvX9qxSD8

Watch the episode right here!

Final thoughts:

This episode reminded us that entrepreneurship is serious, but it also has to be fun. There is so much value in being able to laugh at the chaos, talk openly about the weird and difficult parts of business ownership, and connect with other people who just get it. We had the best time recording this one, and we are so excited to keep bringing more Hustled Up After Hours episodes your way!