This is a bi-weekly series where I share stories from others who are redesigning careers that align with their values, interests, and lifestyle.

When I lived in San Francisco, I planned a party bus (lol) up to Sonoma and met Ryan. It was a blast, and we both found out we had come from a management consulting background. Looking back, we lived very different lives to what we live now. 

Previously, we were both working in corporate. Then, I saw that she left her job to go all in on RetreatVi around the same time I was leaving mine to pivot into events and retreats. 

She’s a positive light on the internet (follow her on TikTok or IG) and is so transparent with the ups and downs of being a founder. If you’re thinking about founding a startup, writing a book, hosting a retreat, or even launching a physical product, Ryan’s already doing it.

Jump to:

Ryan, thanks so much for chatting with me! Before building your own businesses, what did your career look like?

I studied finance in undergrad and then went into management consulting, where I grew professionally for the next 6 years working in M&A, product management, user research, and roadmap development.

Within my first year in that career path, I realized I wanted to have my own business someday to reap the benefits of what I was putting in work-wise. From the people that I admired and a lifestyle perspective, entrepreneurship seemed to be a common thread.

I knew I had a ton to learn and a lot of debt to pay off, so I focused on setting myself up well in the meantime until this grand idea arrived. Setting myself up well meant making sure I felt proud of the work I did, treating every client like a potential future investor, and taking care of that debt as quickly as possible.

Why did you decide to leave the corporate world behind? 

I got the idea for my first startup at a time when I was feeling a lot of friction at my 9-5 between a pay cut, layoff culture, and the very real "the company I work for now just doesn't feel like the same company I joined a few years back" kind of feelings. 

Once I knew how to act on my idea for RetreatVi and the path to launching felt tangible enough, I leaped. I figured worst case I would go into debt and get back into management consulting, but best case scenario…life would open up big time.

What did you have to unlearn from the corporate world as you ventured into self-employment?

One of the first lessons for me was to not shame myself for my own schedule habits. I had to learn to honor my own rhythms and not feel bad about doing what worked for me, like savoring slow mornings and accepting that I do better work at night than I do in the mornings.

There were a ton of other lessons too, like embracing the fact that there are no rules or playbooks and how to create your own motivation and maintain it, from start to finish, without the forcing function of teams and performance reviews.

Ryan enjoying the freedom of being her own boss!

You started RetreatVi, and after 2.5 years of working on it, you decided to close it down. What was RetreatVi and how did you come to that decision? 

RetreatVi was a wellness retreat marketplace, designed to make it easier to find and book retreats around the world.

The reality is retreat margins are thinner than people realize, the quality of the available inventory varies heavily and is ever evolving, double-sided marketplaces are notoriously a nightmare, and to hit the financial milestones I knew I wanted to hit as an entrepreneur, I would have had to probably have no life and compromise on my vision almost completely.

It just wasn’t going to be the boat to get me to where I wanted to be. So I had to decide to stop rowing. I’m very thankful for the synchronicities and conversations along the way that made this feel like a smart business decision, rather than a personal failure.

You’ve hosted retreats as a yoga teacher. I know so many people would dream of doing this. How did you get started? What advice would you give to someone who wants to host their own retreat? 

When I moved to San Francisco, I got a rec from my roommate for a hairstylist, McKenzie, and little did I know that a single appointment would turn into such a beautiful partnership. Even though our in-person meets were limited, we instantly clicked with such depth.

About a year after I completed my 200-hour yoga teacher training, she had completed her somatic breathwork training and called me to ask if I would do retreats with her. Easiest yes ever. 

My advice for anyone wanting to host would be to find a strong team you can lean on and trust, and to not underestimate the amount of work that goes into every phase of planning and hosting. It is no small feat!

Ryan loves sharing her founder stories on podcasts and similar opportunities. 

After you closed down RetreatVi, what happened next with your career? What are you working on currently?

At the time, I was working part-time with a venture capital fund and angel investing group. 

Once I shut it down, I started freelancing with other early-stage founders, which has now turned into my consulting firm, Sun House Studio, where I offer growth strategy, founder advisory, and pitch deck audits. I’m still with the venture groups, and I love how much I get to learn and be exposed to in those rooms.

More recently, I started working fractionally with a female-founded tech agency to help founders build high-quality web + mobile apps, where I support with project management, operations, and client relations. 

As far as my next big bets on myself…I'm getting ready to self-publish my first book and am building Casa de Cielé, which is a bathrobe brand designed exclusively for boutique hotels.

I love a portfolio career approach, as you can tell.

Let’s talk about your first book, From Scratch! Why did you decide to write it and who is it for?

Last year I co-created and co-hosted a 6-month mastermind around the idea of setting strong foundations in mindset and business for early-stage entrepreneurs. It went really well in terms of engagement, but halfway through, my co-host and I realized we didn't want to scale this.

We shared a love of writing, so it was almost a no-brainer to decide to take the mastermind content and create a book. In the end, we decided to scrap most of the business content, and after various pivots, we landed on what it is now: a self-help x The Artist’s Way style book on redefining success to help you live a life that actually feels like yours

From Scratch is for anyone amidst the friction of rethinking their life, trajectory, decisions, circumstances, and perspective on what they actually want in life.

How do you decide which opportunities belong in your portfolio career, and which don't?

To me, it has to feel like an opportunity for me to expand on some level, whether that's the opportunity to earn or to learn well.

I also know I already have a lot going on, so I have to be realistic about the hours and dynamics that actually work for me. I love async work, strategy over pure execution, and efficient Slack use.

I don't think I'd take on something right now that required me to be endlessly on call or had a culture of fire drills and false urgency. 

What are you looking forward to next? 

Getting my book published! I can't wait to hear how it lands for people, and hopefully see some juicy domino effects of people reading it and starting to move differently in their lives.

Where can people connect with you and learn more about your work?

You can find me on Instagram, LinkedIn, Substack, or check out my website.

Ryan’s advice for someone who's multi-passionate and feels pulled in many directions on how to find focus without giving up the things they love:

I had an epiphany moment where I had to rethink my projects and work in the beginning of 2025. When I was in the thick of building RetreatVi, it felt like that was the umbrella, and I was underneath it, almost like I was a part of it rather than it being a part of me. 

I had to realize that the umbrella is me…and all my projects, passions, and interests fall underneath. 

This visual reframe helped me shift from feeling like I had to commit my identity to just one of my passion points and to embrace my multifaceted nature.

My advice: don't lose your identity in any one thing and allow yourself to reinvent, recalibrate, and reprioritize at any given time based on how it all feels to you. 

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