A Life Rewritten After Tragedy
Weekender Hotels CEO on Sentencing, Sobriety and Starting Over
Reading time: About 5 minutes
What Happens After the Worst Happens
A year ago January, I lost my two aunts and my beloved dog of ten years within the span of nine days. It was, without question, the worst time of my life. The grief was unrelenting. I cried so much and for so long that I developed temporary hearing loss, courtesy of fluid trapped in my ear canals from inflammation. For a while, much longer than I care to admit, I wasn’t sure if I’d ever feel like myself again.
I don’t share this for sympathy. I share it because we all face moments that seem impossible. Moments when everything changes, and we’re left asking: What now? Which brings me to this week’s guest: Keir Weimer, Founder and CEO of Weekender Hotels. I don’t say this lightly—I was truly inspired by our conversation. His story is one of profound resilience, and a moving reminder of what’s possible when we choose to rebuild, even after everything falls apart.
Why should you listen?
Speaking with Keir is about more than building a hospitality brand—it’s about building a life you’re proud, even out of the rubble of one you regret. It’s about taking radical ownership of our lives, choosing growth over shame, and forging our own paths, especially when every door slams shut. Here are a few moments that moved me the most:
Redemption + Reinvention: At just 22 years old, Keir was involved in a tragic, alcohol-related boating accident that claimed the life of his best friend. As a result, he was sentenced to 2-6 years in prison. But instead of letting that tragedy define the rest of his life, Keir chose a different path. He got sober (he just celebrated 17 years!), spent his time behind bars doing deep inner work, and began laying the foundation for the life he wanted to lead. As Keir so eloquently said: “Do I let this horrible tragedy define the rest of my life, essentially claiming two lives, or do I repurpose my life for the better?”
Finding a Path Forward through Entrepreneurship: When Keir was released, he thought academia might be his path to redemption. He applied to seven graduate schools, and all seven rejected him. For someone else, that could have been the end. But for Keir, it was a turning point, the moment when he stopped asking for permission. He turned to entrepreneurship, getting his real estate license not as a backup plan, but as a form of self-determination. He made no sales that first year. He was broke, $40k in debt, living at home, and still on parole, but he kept showing up. Eventually, he closed his first deal. Then another. One sale at a time, one opportunity at a time, he built a new identity.
The Power of Focus and Singularity: The most powerful takeaway from this conversation is Keir’s belief in the importance of focus. Keir spent years juggling different projects, chasing ideas, and saying yes to everything. But real growth didn’t happen until he focused solely on one thing: Weekender Hotels. Once he went all-in, the impact and growth was exponential. He said, “It requires getting good at saying no, so that you can say yes later.”
Writing as Reflection: While in prison, Keir started writing as a way to process his emotions and document his experience. He typed up his thoughts on a typewriter and mailed them to his father. His dad helped him edit and shape them into what eventually became his first book— A Quest for Redemption: Stories from Prison. For Keir, writing was more than therapy. It was a way to forgive himself, make sense of his past, and offer something meaningful to others who might be struggling.
The Curse of “Should”: One of the most insightful parts of our conversation came when Keir talked about how many people follow a path they think they should take—because society, school, or family told them they, well, should. But inevitably, this results in feeling stuck. Burned out. Living someone else’s version of success. Or as Keir described it, their own version of a prison. He shares a tactical, deeply reflective approach to finding your purpose and potential. If you’ve ever felt off-course or out of alignment, get ready to have your mind blown.
Favorite Quote from the Episode: Keir purchased his first hotel with friends when he was just 33 years old. I asked him, how did you know how to do that?, and I am obsessed with his response- “Well, we didn't. Bottom line. We had no experience in hotels, events, construction, food and beverage, restaurants—any of that. We just saw opportunity and we figured it out. We created a plan. We had a vision. We knew the market had a need for this. And we're just like, we're going to figure this out… One way or the other, we’re going to figure this out. We know there's demand there, so we took a calculated risk and it really paid off."
Apple Podcasts:
Spotify:
YouTube:
After hosting my short-term rentals (Trout Landing and Gallant Fox) for two years, I finally made the switch to Lodgify, a property management software built for short-term rentals and boutique hotels. They make it easy to manage your calendar, update cross-channel listings, automate guest messages, connect with OTAs, and even build a direct booking website. Best of all, they offer every new customer a personalized, one-on-one onboarding session—that meeting alone taught me more about my listings in one hour than a full year with my former provider. Use code SUITE20 for 20% off their annual plans.
Last Week on Suite Success
Have you checked out my chat with Jasmine Seliga, CEO and Founder of Affixify, yet? She’s creating a company that’s shaking up how hoteliers find the right tech—think matchmaking, but without the awkward small talk or "pay-to-play" fine print. Her episode titled, How this Founder Built the Tinder for Hotel Tech, is available wherever you get your podcasts: Apple Podcasts, Spotify and YouTube.
If you know anything about me, you know that I’m obsessed with capturing memories with family and friends, especially when traveling. That’s why I’m so in love with Flytographer. They connect you with hand-picked professional photographer in more than 350 destinations around the world. They also have an incredible Travel Advisor program. Add a photoshoot to your customer’s itinerary and earn a 10% commission. Visit Flytographer.com/SUITESUCCESS for $25 off your first shoot or to sign up as an affiliate or Travel Advisor.
Until next week, here’s to your suite success.
xx Katie
I want to hear from you! Message me @SuiteSuccessPodcast on your favorite social network, or visit SuiteSuccessPodcast.com to send me a note. Thank you!