Alright – so today we’ve got the honor of introducing you to Brittany Blackman. We think you’ll enjoy our conversation, we’ve shared it below.

Alright, Brittany thanks for taking the time to share your stories and insights with us today. What’s something you believe that most people in your industry (or in general) disagree with?

I believe that societal norms, our parents, and oftentimes, even our own friends place limitations/expectations on us that can stifle creativity.

I vaguely remember sitting in the seat as Speaker Jeff Hoffman walked us through the story of his childhood, life and eventual successes. A lightbulb immediately went off in my head. Even though our stories were vastly different, what if the same thing had happened to me?

I reflected on my achievements paired with the challenges that were always in-tow. See, I have been in managerial/leadership positions all of my life, and as great and inspiring as that sounds, it was difficult. I often experienced backlash, not being taken seriously, or ridiculed because I was 3 things: (1) a woman; (2) young; (3) blonde. Silly, I know, but I have always struggled with people taking me seriously because of these traits.

And that’s when it hit – my past was full of people telling me it wouldn’t work, I would fail, and worse off, that no one would listen to me. The most painful part though was that I believed this! I stayed quiet, always masking this internal belief that I was meant for more, for better, for different.

Over a year or two of self-discovery and having a life coach, everything changed. I learned what limiting beliefs even were, where they came from, and how to rewrite the script. I began not only fully accepting who I was and who I was meant to be, but also courageously stepping into the unknown to create a life of zest, wonder, and fulfillment. I no longer carry around the expectations others have of me; I don’t try to change them either. I practice self-awareness, allow myself silence to sit with my own thoughts, dreams, and fears, and take intentional steps in a direction that best serves me, limitless these days.

Brittany, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

I have always enjoyed serving others. My career started in retail and restaurants, learning effective sales communications, leading teams, and working towards sales goals. Right after high school, I moved from Georgia to Florida, where I eventually landed in the vacation rental industry as a professional property manager. Working as Operations Manager and for a company 9 years later, I found myself wanting more…

In 2020, I took a huge leap of faith and started my very own bootstrapped vacation rental property management company. I successfully grew the rental business over the next 4 years and sold the company in late 2024. After transitioning that company to the new Owners, I was able to dive into my next endeavors: Discover Freedom coaching.

My success hasn’t been happenstance. I hustle, stick to my word, and have a keen eye for detail and preciseness. With nearly 2 decades of experience in leading teams, I have paired my coach training to become a powerhouse in working with leaders and teams in creative leadership development.

I’m incredibly thankful for my family, friends, and community for always cheering me on, and success doesn’t go without being cognizant of the personal brand you’re building over time. Do good work and treat others well. Failure isn’t possible; only learning experiences. Own everything you do with 100% zest. Live life looking out the windshield, not by staring into the rearview mirror. Oh, and when you fear something new, just do it.

Can you talk to us about your experience with selling businesses?

Yes, I sold my vacation rental property management company in late 2024. To put it simply, the sales process is like someone seeing you in your underwear.

What does this mean exactly? It means they see everything – any imperfection and all the beauty; anything you have tried to hide; and the things you had no idea were there. So, be ready. Oh, and get ready for a possible identity crisis as well, especially if you put your heart and soul into the business.

It’s a roller coaster of emotions – the ups and downs of happiness, sadness, fear, anger, you name it – you’ll probably experience it at some point.

My advice for anyone selling their company:

1. Financial hygiene – make sure you know your numbers and can explain them
2. SOPs – ensure that every system and operation is recorded and repeatable
3. Back out – work to back yourself out of the day-to-day. This isn’t necessary but depending on your industry and whom you want to sell to, it could be a vital need for a buyer to accept the risk of purchasing your business.
4. Hire a coach – for the love of everything, have a trusted, safe confidant that you can rely on to work through the emotional highs and lows. Don’t try to do this by yourself.
5. Pay a broker – it’s worth it. Believe me. Interview them. Don’t just go with the first shiny object. Make sure you like this person, can work with their communication style, and align with their values/industry experience.

Are there any books, videos or other content that you feel have meaningfully impacted your thinking?

1. Coaching training
2. Read more books

I believe I got so caught up in my younger years just hustling and having fun that I forgot to place any importance on personal/leadership development. Had I known then what I know now, I would have read a few books every year that focused on self-awareness and how to coach, not direct. Coaching training has changed my life – both professionally and personally – in how I communicate. Feel free to reach out to me, and I’ll be happy to share more resources.

For now, check out these books:
* The Let Them Theory
* Ask Powerful Questions
* Don’t Shoot the Dog
* Know Your Why
* Find Your Why

Contact Info:

• Website: https://discoverfreedom.life/
• Instagram: https://www.instagram.com/discoverfreedom.life/
• Facebook: https://www.facebook.com/discoverfreedom.life/
• Linkedin: https://www.linkedin.com/in/brittany-blackman-384141216/
• Youtube: https://www.youtube.com/@Discover-Freedom