July 15, 2025

Data to Dollars: Turning STR Metrics into Money Moves with Carolyn O’Brien Are you ready to transform your data from a confusing mess into your business’s most powerful growth strategy?

39 minutes

In this episode, I sit down with dashboard and data visualization expert Carolyn O’Brien, who’s on a mission to make data not just understandable—but actionable.

Carolyn shares her journey to becoming a data visualization guru, helping entrepreneurs ditch the overwhelm and step confidently into data-driven decision-making. Together, we dive into how visualizing your business metrics—through simple, beautiful dashboards—can unlock powerful strategic insights.

Think you’re “not a numbers person”? Think again. Carolyn walks us through how anyone can build a custom dashboard that tells you exactly what’s working (and what’s not)—from property performance and booking trends to revenue optimization and ROI.

And here’s the best part: Carolyn and I are teaming up for a three-day “Data to Dollars Challenge” this August! You’ll learn how to build your very own real-time, visually stunning dashboard that helps you grow smarter, not harder.

Whether you’re managing a single unit or scaling a full portfolio, this episode will change the way you think about data forever. No more guessing. No more overwhelm. Just clarity, confidence, and serious business intelligence.

Let’s turn your data into dollars! Here is the link to join the challenge!

HIGHLIGHTS AND KEY POINTS:

[01:17] A short introduction about our guest Carolyn O’Brien and how she help business owners understand data and metrics

[03:28] Carolyn shares the game-changing power of visualizing business data and her clients’ feedback

[04:27] Carolyn emphasizes that data doesn’t have to be overwhelming—especially for those intimidated by spreadsheets

[06:56] Carolyn’s strategy for making data review a weekly habit that drives better business decisions

[08:36] Carolyn’s perspective on how clarity with numbers transforms business decisions

[12:36] How clear, visual data not only improves business strategy but also strengthens communication between partners who co-invest

[15:08] Carolyn explains how visual dashboards empower women to confidently engage with their numbers

[22:38] How Carolyn's dashboard design unlocks smarter decisions in the short-term rental space

[23:57] Carolyn emphasizes the value of integrating Airbnb data into custom dashboards to offer clarity and context for short-term rental owners

[25:38] Introducing “The Data to Dollars Challenge” – a three day challenge to empower and help short-term rental hosts turn their data into actionable business insights

[29:07] Carolyn offers advice to anyone intimidated by numbers or spreadsheets, especially those intrigued by the upcoming workshop but feeling hesitant

[30:04] The lightning round

Golden Nuggets:

“Getting started doesn't mean tracking everything, because tracking too many numbers is almost just as bad as not tracking anything at all.”

“Data can help back up so many different decisions, no matter what type of business you're in, no matter what size of business you're in.”

“It's so critically important now, even more than ever, that we are making strategic decisions when it comes to our portfolio, when it comes to our investing, when it comes to perhaps what properties we want to, you know, redeploy money from.”

“Sometimes you can learn from someone what not to do, which is more helpful than someone telling you what to do.”

This episode is brought to you by ⁠⁠⁠Lodgify⁠⁠⁠!

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Let’s Connect!

Instagram: https://www.instagram.com/carolynobrienstrategist/

Website: metricssuccess.com

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By Stacey St. John

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