Meet Dr Cali EStes | CEO Sober on Demand and The Addictions Academy

We had the good fortune of connecting with Dr Cali EStes and we’ve shared our conversation below.

Hi Dr Cali, we’d love to hear about how you approach risk and risk-taking.
Taking Risks in Business and Life: My Journey from Homelessness to Building 8-Figure and 7-Figure Companies

If there’s one thing I’ve learned throughout my life, it’s that taking risks isn’t optional—it’s necessary. I’ve faced moments where I had nothing left to lose, but I bet on myself anyway. Twice in my life, I found myself homeless, with no safety net and nowhere to turn. It would have been easy to give up, but something inside me refused to settle. I knew I was capable of more, and I was willing to take the biggest gamble of all—betting on myself.

I started my first company with less than $300 in my bank account. I had no investors, no fancy business plan, just an unshakable belief that I could make something out of nothing. It wasn’t easy. I had to hustle harder than anyone around me, work late nights, and overcome rejection after rejection. But slowly, things started to shift. That company eventually hit 8 figures, and it was proof that taking risks, even when the odds seem stacked against you, can change your life.

But life doesn’t always go according to plan. In 2008, when the market crashed, I lost that 8-figure company overnight. Everything I had built was gone, and I found myself back at square one—homeless again and with no safety net. It was devastating. I could have thrown in the towel and accepted defeat, but I’m not wired that way. I took a deep breath, licked my wounds, and did what I do best—I started over.

With less than $300 in my account (again), I built another company from scratch. Most people would have played it safe after losing everything, but I knew I was built for more. I poured my energy, knowledge, and experience into that venture, and that business grew to 7 figures. I refused to let failure define me. Instead, I used it as fuel to push forward.

What I’ve realized through these experiences is that taking calculated risks is the key to success. Fear is always going to be there—whether it’s fear of failure, rejection, or uncertainty. But if you let that fear control you, you’ll stay stuck. The real magic happens when you push through that discomfort and go all in, even when the outcome is unclear.

Risk isn’t about being reckless. It’s about recognizing an opportunity and having the courage to seize it, even when everything feels uncertain. Every successful entrepreneur, leader, and innovator has taken a leap of faith at some point. They weren’t guaranteed success, but they trusted their instincts and went for it. And that’s exactly what I did—twice.

So, if you’re standing at a crossroads, wondering if it’s worth taking that leap, remember this: You don’t need to have it all figured out. You don’t need a massive bank account or a perfect plan. You just need the courage to start, the determination to keep going, and the belief that you’re capable of achieving greatness.

Because if I can go from being homeless twice to running multi-million-dollar companies, then so can you. All it takes is one bold decision to change the trajectory of your life. Are you ready to take that risk?

Alright, so for those in our community who might not be familiar with your business, can you tell us more?
Dr. Cali Estes: Flipping the Script on Recovery with Sober on Demand

Let’s be real—traditional rehab isn’t for everyone. Who’s got 30 days to disappear from life, business, and Netflix binges? Not my clients. That’s why I created Sober on Demand—a concierge-level, VIP recovery experience that meets my clients where they are, whether that’s their penthouse, private jet, or, yes, even a hotel in Bora Bora. I work with CEOs, musicians, and high-profile clients who need real solutions that fit into their fast-paced lives. Rehab without the walls? You got it.

With Sober on Demand, I ditch the cookie-cutter approach and customize each program like a tailor fitting a bespoke suit. Need detox? Got it. Mindset overhaul? Done. Life falling apart faster than a cheap suitcase? I’m there to help you hold it all together. I’m not just your coach—I’m part therapist, part life strategist, and part drill sergeant (with love, of course). I guide my clients through addiction, trauma, career chaos, and relationship rollercoasters. And I don’t just get them sober—I make sure they stay sober while crushing it in life.

But wait, there’s more! For my high-achieving go-getters who are this close to burnout, I’ve designed the 5-Day Executive Reset—a turbocharged program that blends biohacking, mindset upgrades, and addiction recovery techniques to reset both the body and brain. It’s like hitting Control+Alt+Delete on your life, but with better results and no IT department required. Perfect for executives and entrepreneurs who need rapid transformation without hitting pause on their careers.

So, whether you’re battling addiction, burnout, or just need a life reboot, I’ve got you covered. Sober on Demand isn’t just about getting clean—it’s about taking back control, finding balance, and becoming the best version of yourself. And trust me, I’ll make sure you get there—with a little tough love and a lot of results.

Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
🌴 Best Places to Explore in Miami
1. South Beach (SoBe)
✅ Why Go: Iconic, lively, and full of life! South Beach is the heart of Miami’s vibrant culture and nightlife. Stroll along Ocean Drive to soak in the Art Deco vibes, people-watch, and grab a cocktail at one of the trendy rooftop bars.
✅ Don’t Miss: Sunset walks on the beach and a visit to Lummus Park for yoga or a morning run by the water.

2. Wynwood Walls & Arts District
🎨 Why Go: Perfect for someone who appreciates creativity and culture! Wynwood is a colorful neighborhood where world-renowned street artists showcase their work. You’ll love the energy, the vibe, and the eclectic mix of galleries, breweries, and coffee shops.
✅ Don’t Miss: Grab a coffee at Panther Coffee and explore the Wynwood Walls for those Instagram-worthy shots.

3. Little Havana
💃 Why Go: Immerse yourself in Cuban culture in this vibrant neighborhood. From salsa music echoing from local cafes to hand-rolled cigars and Cuban coffee, Little Havana is full of life and flavor.
✅ Don’t Miss: Try a café con leche and pastelito at Versailles, a Miami institution. If you’re there on the last Friday of the month, check out Viernes Culturales, an outdoor cultural festival.

4. Brickell & Downtown Miami
🏙️ Why Go: Brickell is Miami’s financial hub and home to luxurious high-rises, trendy rooftop bars, and upscale dining. Perfect for a night out or a romantic dinner with a view!
✅ Don’t Miss: Drinks at Sugar rooftop bar, where you can take in panoramic views of the city.

5. Vizcaya Museum and Gardens
🌸 Why Go: If you’re in the mood for something more serene, head to Vizcaya. This European-inspired estate offers breathtaking gardens, a waterfront view, and a glimpse into Miami’s history.
✅ Don’t Miss: Wander through the gardens and enjoy the peaceful escape from the hustle and bustle.

The Shoutout series is all about recognizing that our success and where we are in life is at least somewhat thanks to the efforts, support, mentorship, love and encouragement of others. So is there someone that you want to dedicate your shoutout to?
Shoutout to My Amazing Sister, Jenny Fontana! 💖🙌

I wouldn’t be where I am today without my incredible sister, Jenny Fontana, by my side. She’s been there with me through it all—helping me build Sober on Demand and The Addictions Academy from the ground up. When I had a vision to create something that would change lives and redefine addiction treatment, Jenny was right there, rolling up her sleeves and making it happen. Her dedication, loyalty, and unwavering support have been a driving force behind our success.

From brainstorming ideas to handling the nitty-gritty details, Jenny’s hard work and commitment helped turn these dreams into reality. I couldn’t have asked for a better partner in this journey. Jenny, thank you for believing in the vision, standing by me through the highs and lows, and being the rock that keeps everything moving forward. 💪❤️

We built something truly extraordinary together—and I’m beyond grateful to have you by my side. Love you always! 💕✨

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Image Credits
niicholas booth photography