This coaching is for owners, operators, and investors who want results — not another self-paced course. If you’re here for structure, action, and personalized support; you’re in the right place.
We left a coaching program after discovering how hard it was to actually get helpful input into our specific situation and questions - despite the sales job that we'd have direct coaching. Working 1:1 with Kate was precisely what we needed - and one STR down and another in the works is proof!
Its been incredibly helpful to have someone else to hear our rambling ideas and put structure and action to it. Can't recommend Kate enough - she is not only knowledgable, but really invests in us.

"I wish I'd found you a year ago; I bought a course I didn't want in order to just have someone I could talk through my goals and thoughts - which didn't happen. Having you to just coach me through a few sticking points was perfect."
Mike F, January 2023


Due to the 1:1 nature of the program, slots are limited. A Fit Call is required. On occasion, a 3-month strategic sprint package is available and may be offered during our Fit Call if approperiate. Also see the Ad Hoc Hourly Consult option for a single, 1 hour consult.


The business reasons for short term rentals? There are many - I personally enjoy at least 30% cash on cash returns across my portfolio (my newest hit 45% year one!) When I was working in my healthcare executive job we leveraged the Short-term Rental Loophole and went from a $50K tax bill to a $14K tax bill, our net worth has substantially increased in just 3 years AND our assets are paying for themselves while making a profit (cash in hand last year $52,347 on 2 properties - that will double this year - plus any additions to the portfolio we make).
Business reasons aside - we mix business and pleasure; my kids love visiting and staying at our properties. Our oldest actually go married at one! Its truly a fun and enjoyable investment vehicle. Our vacation budget even decreased because we use our properties instead of always paying for others, and its a business that I can include my kids in and model for them what it means to be an entreprenuer
After losing tens of thousands on a short term rental investment gone wrong, Jeannie and Bill learned from their mistakes and sought the knowledge they needed.
A couple years ago Jeannie and Bill sought out coaching services following a deal gone wrong. They sheepishly shared with me all the way's they'd allowed themselves to be steered wrong;
- Trusted their realtor to get them the right deal without verifying the numbers themselves
-Didn't understand or know how to check on regulatory requirements for renting out their home
-Got talked into buying a property that cost more than they wanted to spend
-Believed the property would be successful without checking the numbers themselves
I'm pleased to report Jeannie and Bill - after licking their wounds and learning their lessons, got they expert help they needed (me!) and together we analyzed potential properties while they shifted mindset to approach their investment as a business . Jeannie and Bill - a lovely couple nearing retirement, have achieved their goal of a beautiful cash-flowing short term rental investment they enjoy a couple times a year - with their kids and grandkids.
No question that the number of short-term rentals has increased - doubled in some markets, following the sharp increase in demand in 2020/21. While opportunities still exist in some markets, other markets may not be great investment locations due to saturation or regulations. That said, the right house in the right location will ALWAYS cash flow. We may have to work a little harder to find it - but opportunities exist. And like any real estate investment, if you are interested in doing improvements you'll have an even broader field to choose from. Short term rental demand is predicted to remain steady, and likely supply will begin to drop off due to people who bought without going through a full analysis. Savvy investors absolutely can get into the market now and still reap all the benefits of being a short-term rental investor.
Being an investor means passive income. While short-term rental investing is not a passive business, like any business - you can set it up for success by outsourcing day to day operations, setting up a team, or doing it yourself. Whatever your goal, The CEO Host helps you explore your options and decide what works best for your goals - and how to achieve it.
Everyone starts with different resources. Does it cost money to get involved? Of course - acquiring a property, setting it up; these things cost money. Within The CEO Host we can discuss - and have experience with, alternatives to cash like leveraging equity you already have, loan programs with lower down payment requirements, finding rentals that are fully furnished, partnering with others, and even using hard money. Whatever your goals, we can work together to outline a plan to get you to it.
Within the coaching program, I do not help source potential deals; everyone has different goals and goal posts. Sometimes I may have a deal I share with clients and I occasionally take on clients who contract with me specifically for this - feel free to hop on my calendar if this is of interest. The coaching program helps you learn how to source deals and we review the first couple together, and then I provide email feedback after you have the basics down.
If you appreciate that leveraging other peoples experience and energy for your own success, then I look forward to working with you. There are almost no programs offering 1:1 coaching. You can leverage my experience coaching over 300 people to date, thousands of hours of training, attendance at industry conferences - all for your benefit - cutting down the time it takes you and minimizing the likelihood of costly mistakes. I don't do group coaching, I don't offer a "master class" where you have to do it all yourself - the Knowledge Library has all the resources you might need and none of the pressure of "completing the course". Working with The CEO Host means you get high quality consulting and coaching to your goals on your timeline, meeting you where you are at in your journey and gets you to your goal.
You can pay $10K, $15k, even $25K for a "mastermind" with others in the industry seeking to get started - rearranging your schedule to make those weekly group coaching sessions, navigating expectations to complete course work (that inevitably never quite gets done) - and get little to no actual attention to your specific situation or goals. For some, you may prefer this experience and it will be well worth your time and investment. I encourage you to carefully evaluate any program you consider!
OR leverage my time and experience, fully focus on your goals for under $5K - leaving you confident, informed, and succeeding in your STR goals.. Sign up today before prices go up! I can only take on a limited number of clients, so take advantage now. I've already increased prices; I guarantee they will double in the next year in order to manage my calendar!
As a professional in the STR industry, my experience stems beyond just getting started - I have owned multiple STR and managed for others, work with private money (lending and borrowing), rehab, and leveraging tax benefits. I have some experience w small resorts as well. If you would like help to level up your business, Lets Talk and see if I'm a good fit for your goals. Generally, I'm a good fit for smaller owner-operators and investors who have/seek a small portfolio, looking for a boutique resort or just wanting to figure out how to own that dream second home that offsets its costs.