Blake Dailey

Blake Dailey started his real estate investing career renovating hurricane-damaged homes in Panama City, FL. He has also served as an Acquisitions and Contracting officer in the US Air Force where he has managed contracts as large as $40M. Blake has now bought, renovated, and managed a $17M portfolio of 6 Boutique Hotels in Lake Tahoe, Panama City Beach, and the Smoky Mountains and oversaw the construction management of upwards of $5M in renovations on the projects. Blake also owns his newest 130 unit Hotel and resort where "Boutique Hotel Con" will be hosted. Blake will be speaking on the art of finding deals, as well as hotel operations and management.

Jack "Buck" Buczkowski

Beginning his Boutique Hotel investing career in 2021, he got into the industry by developing his own projects from the ground up. He got his big break when he pitched his first hotel concept to one of his early clients and they seed-funded the project with $250k and soon after he moved to Arizona to start the development. Buck is a master capital raiser and raises entirely from LP investors. With 4 hotel projects of his own under his belt, he’s continuing to scale with more properties and will continue leading the space in his expertise of raising capital. 

Mike Sjogren

Michael is a husband, father, investor, entrepreneur, CPA, mentor, podcast host and short term rental expert. Michael is also the founder of Short Term Rental Secrets, a mentorship program to help new and seasoned real estate investors launch, automate & scale their short term rental and boutique hotel portfolio to fast track their financial freedom. He currently has a portfolio of 82 short-term rentals across three states including 2 boutique hotels on Boston’s north shore. Michael is also the co-founder of the industry’s largest host-driven conference - STR Wealth Con. 

Diana Ossa & Josh Dobken

Diana and Josh are architects, real estate investors, and boutique hotel operators who combine design-forward thinking with investment strategy. With over 15 years of experience in architecture, construction management, and operations, they’ve built a portfolio of 30+ furnished rentals and boutique hotels. Their flagship property, Terra Palm Springs, has earned international acclaim—including features in Forbes, Vogue, and Travel + Leisure’s 2025 It List. Diana and Josh will be speaking on design-driven development and how to maximize returns through strategic renovations and guest experience.

Steph Weber

Steph Weber, a branding and marketing powerhouse, STR and micro resort investor, Host of the Branded & Booked Podcast, and STR co-host. She is the CEO of The Weber Co where she’s helped over 100 small businesses scale to 6 and 7 figure brands and now focuses on hospitality. Together with 3 other couples, they are building Cabins on the Cumberland, a micro resort and event venue. She and her husband also built a 6-figure co-hosting company in just one year. With 10 years of experience working as a brand and marketing strategist, Steph brings new energy to the world of short term rentals and boutique hotels, helping investors and guests experience destination properties with rave-worth experiences. Steph lives in Indianapolis with her husband, Collin, and two boys. Together, they spend as much time outside as possible, camping, hiking, and exploring. .