42. Startup Reality Check: Chase Grills Ryan on What Really Happened in the First 90 Days

In this episode, Chase puts Ryan in the hot seat to break down the emotional rollercoaster of launching their latest dental startup. From unpredictable days to unexpected wins, this is the raw debrief most practice owners never share out loud.

Starting a new dental office is rarely what you think it’s going to be. Chase takes on the role of interviewer in this week’s episode, asking Ryan to reflect honestly on the chaos, confusion, and surprises of their newest startup.

Ryan opens up about how disjointed the first few weeks felt—even with strong hiring and good systems in place. The hardest part? Leading through the fog. When your team is looking to you for direction and you don’t yet have clarity yourself, it’s a gut-check moment.

They discuss team dynamics, emotional stress, communication breakdowns, and the temptation to avoid hard conversations. Ryan shares how “looking like you have it together” isn’t the same as actually leading, and what it takes to find your rhythm mid-mess. If you're planning a startup or recovering from one, this conversation is both validating and eye-opening.

💡 Key Takeaways:

• Chase’s opening question: “What surprised you most about this startup?”
• The emotional tension of unclear direction during the first month
• How a few misaligned hires can create ripple effects across the office
• Ryan’s honest take: “I didn’t show up the way I needed to”
• The danger of avoiding hard conversations when things feel fragile
• Learning how to lead when you don’t have all the answers yet

👉 Want the real story behind the startup glow-up?

Hit play to hear Chase and Ryan pull back the curtain on what those first 90 days really looked like.

Episode Minute By Minute: 

• 0:00 – Intro: This startup hit different
• 2:10 – Chase: “What did we think would happen... and what actually happened?”
• 4:05 – The first two weeks: chaos, burnout, and doubt
• 6:50 – “I wasn’t the leader I wanted to be”
• 9:15 – When your team feels the tension, but no one says anything
• 12:00 – Missed expectations, no-shows, and schedule gaps
• 14:35 – “We built the house while living in it—and lit it on fire”
• 16:45 – Learning to give grace while still setting standards
• 19:30 – What we’re changing for the next startup
• 22:00 – Final thoughts: You’re not alone in the mess