Startups Pay Her $25K a Day to Have Uncomfortable Conversations

After building and selling Santa Monica's largest outdoor fitness program, Angela Parker expected to feel successful. Instead, she felt empty.

That identity crisis led to a six-month technology detox in the Italian Alps and the creation of a powerful facilitation framework used by companies on track for billion-dollar exits.

In our exclusive Hampton interview, Angela reveals:

• How she went from free workshops to commanding $25K a day
• Why the conversations your team is avoiding are your biggest growth blockers
• The workshop exercise that Hampton explicitly told her not to do... but she did anyway
• The facilitation techniques that create transformational leadership breakthroughs

If you’ve ever wondered whether it’s possible to build both a successful business and a fulfilling life, Angela has some surprisingly practical answers:

Hello! Who are you and what business did you start?

I'm Angela Parker. I help founders, leaders and high-performing teams unlock their next level of impact. I'm a facilitator, speaker and trusted coach to top executives, fast scaling startups and mission driven organizations. My work is built around elite level leadership development, transformative offsite experiences and high impact facilitation. I help leaders not just navigate complexity but thrive in it. Essentially, I built a business that helps these people perform. I really do help some of the world's most impressive performers do their work even better.

My core offer is designing workshop curriculum for teams, companies, and communities. For example, Hampton is one of my clients; they brought me in to design curriculum specifically to create a sense of belonging and connection for their community. I have companies that bring me in to create team alignment. Some bring me in because they're a roll-up company on track for a billion dollar exit, but there's a lack of cohesion inside the organization and they know if they don't address it, they're not going to sell. People turn to me to create experiences—in-person and virtual, workshops, and conversations that allow their team to scale with ease.

I also offer bespoke coaching retreats for founders and entrepreneurs. Very small, around 12 people, in amazing locations like Japan, the Italian Alps, and Tuscany. Additionally, I do VIP coaching days where it's just me and the client in person for a day.

My day rate begins at $20K. For group programs, my masterminds run at $20K for a few months. They move the needle in an insane way. Yes, because I'm magic. But also by creating the time where participants know they have to show up and give everything. It's a huge unlock.

What's your backstory and how did you come up with the idea?

I founded and eventually grew the first Outdoor Fitness Bootcamp in Santa Monica. It became the largest and longest-running outdoor fitness program. I sold that program in 2018, and I thought it was going to be an amazing experience—but it wasn't.

The sale is something I talk about a lot because it was brutal. It was one of the hardest things I went through. I thought when you sell something, you get to feel this incredible hit of success. I thought I was going to feel like a whole person, truly successful. But that's not what happened. I sold it and I felt exactly the same. And that made me feel terrible.

The thing that I thought was my North Star wasn't my North Star. That sent me into an absolute downward spiral. I took a sabbatical in the Italian Alps, and although it was a beautiful experience, it was actually really hard. I got very sick and had to come face to face with the fact that I had attached my identity and all of my self-worth to this company, and without it, I was actually a shell of a person.

During that experience, I did so much research. I hired a coach, worked with a therapist, and ruthlessly examined my life. I was not on social media, didn't look at emails. I was off all technology except the notes app and music on my phone for six months.

In that experience of becoming a person and re-identifying who I was, my question became: can you be an entrepreneur, a founder, and be a whole person—and what would that take?

I realized that understanding how values work, healing your trauma, and not allowing anything to turn into a blind spot is the only way for anyone to become truly successful, completely present, and feel like a whole person.

I then tested my methods. I asked some of the most impressive people I knew in business if I could test them on them. I actually thought they would validate that I was crazy and it was nonsense. They did the opposite. People came back saying that this was something unlike anything they'd seen before.

Take us through the process of building and launching the first version of your product.

During Covid, I had 112 people sign up from 10 countries for a group program that was originally supposed to be two weeks. It lasted for four months, and we met every day during that time.

I already had an audience from my first business, so I initially went to that audience. There were enough people that I had already been working with and who knew me as an entrepreneur.

It was a pay-what-you-want fee and we donated everything because it was during Covid.

Since launch, what has worked to attract and retain customers?

This is what's weird. I understand that word of mouth is not a strategy. We all know that. But for me, it has been.

Here's why: when you are in one of my retreats or workshops - whether you come to the retreat in Italy, another international retreat, or you're brought in through Hampton - you experience something different. When people get to experience what happens inside these events, they realize the standard for what everyone should be experiencing is different.

The thing is, we're not making people think, we're making them feel. I make people feel things and because of what I'm doing in the room, they're having personal unlocks in a public experience… that makes people want to share that experience with their friends and family. 

Up until now I have been 100% word of mouth, which is weird because I'm a business person and I know that's not a strategy, but that's what's worked.

Plus, everyone from last year has come back as clients... the repeats are crazy. Once someone brings me into their company, they keep bringing me back for more things.

How are you doing today and what does the future look like?

I'm going to begin teaching my methodology for how to design workshops and create curriculum. I'm doing something in the industry that no one else is touching yet. I know it's that skill set that's creating magic, and I know I can teach that.

I plan to expand into London this fall. It's a little bit closer to the Italian House. In addition to expanding into London, I'm going to begin a workshop and facilitation instruction school. We're defining what that is, but we'll be offering trainings starting at the end of this year.

A big part of this next phase includes high-impact content – think deeply resonant thought leadership that helps leaders heal, lead, and scale with more ease. This means launching a podcast, potentially expanding into YouTube, and bringing in a learning expert to enhance the experience.

It’s about amplifying reach, refining our impact, and ensuring that every touchpoint whether through facilitation, speaking, or coaching creates meaningful transformation.

Did you ever have an “oh shit” moment where you thought it wouldn’t work?

Those "oh shit" moments actually come in facilitation. This is a great story. There is a very special exercise that we do in the first 15 minutes of the foundation's retreat. When Jordan was the CEO, he told me under no uncertain terms that I was not allowed to do that exercise. He said, "That is too much. That is too far. That is too intimate."

Jordan was at the very first retreat, and I did not do this exercise. Jordan was not at the second retreat, and I did the exercise. When I first spoke the exercise, there was a moment when it felt like the air had left the room. I thought, "Not only am I going to be fired, but I think everyone will hate this retreat."

Then it was time for people to share, and it's now a signature part of the Hampton retreat. It has stayed in the curriculum.

My "oh shit" moments have never been about whether the business would be successful. They've been about the big swings I've taken in facilitation, and they've actually turned out to be the biggest and best lessons. I've learned that if I trust my instincts and hold the perspective that everyone in a workshop wants to be pushed, it works. People want to be asked the hard questions, and I trust in their ability to go as far as possible.

This has been the best lesson, and in a very full circle experience, it's fascinating because I didn't know or trust my instincts in my first business. But because I literally "dog food" my product and do the things I make other people do, I now know what it's like to trust my instincts. My "oh shit" moment actually proved that I am a whole person with a full identity—a complete journey from where I started.

Can you break down the keys to this business model for us? What makes it work? And what do outsiders typically not understand about your industry?

The key to this business model is simple: Real conversations create real results. But most leadership teams aren't having the conversations they actually need to have. They're avoiding tension, skimming the surface, or wasting time on the wrong problems.

That's where facilitation comes in. What makes this work is that it's not just about running a meeting – it's about creating a structured space where clarity happens. My role is to design and guide high-impact discussions that force alignment, push past bottlenecks, and get executive teams unstuck, fast. This isn't about fluff or forced "team bonding" – it's about making sure that when leaders step into a room, they walk out with game-changing decisions, not just good intentions.

The biggest misconception about facilitation is that any great leader can do it themselves. But the truth is, you can't facilitate and lead at the same time. If you're running the conversation, you're not fully in it, and the conversations you avoid in the room will show up later as misalignment, inefficiency, and poor execution. That's why the best founders, executives, and leadership teams bring me in… so they can stop spinning in the same cycles and actually move forward with clarity and confidence.

What have been the most influential books, podcasts, or other resources?

My research + curriculum design that supports transformation around trauma/ attachment/ healing/ embodiment/ vulnerability/ creativity/ compassion was built on top the work by the following people. 

• Tara Brach (Radical Acceptance) 
• Jack Kornfield (A Path with Heart)
• Brene Brown (The Gifts of Imperfection + Atlas of the Heart)
• Michael Singer (The Surrender Experiment) 
• Gabor Mate (When The Body Says No)
• Don Miguel Ruiz (The Four Agreements)
• Elizabeth Gilbert (Big Magic)
• Dr. Sue Johnson (Hold Me Tight)
• Bessel van der Kolk (The Body Keeps the Score)
• Dr Robin DiAngelo (White Fragility)
• Reni Eddo-Lodge (Why I’m No Longer Talking to White People About Race)
• Melody Beattie (Codependent No More)
• Pema Chodron (When Things Fall Apart)
• Miranda Gray (The Optimized Woman)
• Dr. Kristin Neff (Fierce Self-Compassion) 
• Co-Active Coaching 
• Alok
• Tarana Burke 
• Hala Khouri
• Danielle LaPorte
• Peter Alan Levine
• Karen Anderson 
• Jeffrey Marsh
• Roxanne Gay

When it comes to business/ leadership/ mindset/ performance/ physical body I respect these people and enjoy this work.

• Ben Horowitz (The Hard Thing About Hard Things + What you Do Is Who You Are)
• John Doerr (Measure What Matters)
• Adam Grant (Give and Take)
• Chris Voss & Tahl Raz (Never Split the Difference) 
• Bill Campbell (Trillion Dollar Coach written by Eric Schmidt, Jonathan Rosenberg, Alan Eagle)
• Andrew Grove (High Output Management) 
• James Clear (Atomic Habits)
• Simon Sinek (Start With Why)
• Malcolm Gladwell (The Tipping Point)
• Frances Frei & Anna Morriss (Move Fast and Fix Things)
• Andrew Huberman (Huberman Lab Podcast)
• Design Thinking (This Is Service Design Methods)
• Charles Einstein (The Yoga of Eating)
• Sahil Lavinia (The Minimalist Entrepreneur)
• Jake Knapp (Sprint)
• Raj Jah (The Business Unlock)
• Peter Attia (Outlive)
• Seth Godin

Memoirs / Human Stories / Connection/ Community/ Joy

• Viola Davis (Finding Me)
• Tara Westover (Educated)
• Jennette McCurdy (Im Glad My Mom Died)
• Molly Shannon (Hello, Molly)
• Dave Grhol (The Storyteller) 
• Tembi Locke (Tembi Locke)
• Maggie Smith (You Could Make This Place Beautiful)
• The Power of Moments (Chip Heath + Dan Haeth)
• Breathing Makes It Better (A children's book by Christopher Willard and Wendy O'Leary)
• Jennie Slate (Life Form)
• Amy Poehler (Yes Please)
• Rainn Wilson (Soul Boom)

Where can we go to learn more?

Website:angelaparker.com

LinkedIn: linkedin.com/in/angelamparker (Connect with me for valuable insights on leadership, facilitation, and high-impact coaching. I share strategies, reflections, and game-changing content to help you scale with ease.)

Instagram: instagram.com/angelaparkerfit (Follow along for a behind-the-scenes look at my work, personal rituals, and the lifestyle that fuels my mission.)

Newsletter: angelaparker.com/newsletter-sign-up (Subscribe for exclusive wisdom on healing, leadership, entrepreneurship, facilitation, systems design, nervous system regulation, creativity, and more.)