Episode 13 - From Proving To Becoming:
An Entrepreneur’s Journey

Join host Aaron Burnett as he sits down with Russell Benaroya, COO of Timberland Partners, to explore the pressure of living up to a legacy, the vulnerability behind entrepreneurship, and the mindset shifts that helped him design a life rooted in freedom.

Russell is Seattle-based entrepreneur, investor, and operator with a background in investment banking, private equity, and multiple ventures across health tech and financial services. Co-founded and exited several companies including Every Move and Stride, and is the author of One Life to Lead. A longtime EO member, Russell is passionate about helping entrepreneurs build businesses that align with the lives they actually want to live.

Note, this podcast features real entrepreneurs sharing real challenges and solutions. No pitches, no sales - just honest conversations about the moments that shape successful businesses.

Growing Up a Benaroya in Seattle

Aaron: I'm very much looking forward to this conversation. You're a fascinating person — I know little bits about you that intrigue and inspire me. Tell me about growing up in your family. I've heard you had a wonderful childhood, and you grew up in a family with a very prominent name in Seattle. Can you tell me what it was like to grow up in that family and how you embarked on your career?

Russell: The way I'd answer that in a meaningful way is less about the beginning of the journey and more about the middle of it. The middle was coming back to Seattle as an adult — after business school and a stint in banking in New York — with this fear that I wasn't going to be enough, or that I somehow needed to prove myself. While I'm so grateful for being a Benaroya in Seattle, I also acknowledged that so much of that name recognition came from my great-uncle, my grandfather's brother. I hadn't really done anything on my own, so I spent a lot of energy feeling like I couldn't reveal that I was starting from Square One — until I finally could. Some of that came from the humbling nature of entrepreneurship, from working through the lows and knowing you have to strip everything down and build it up in a way that works for you authentically.  I had to let go of the idea that being Russell Benaroya meant others had expectations of me. That's on them, not on me. What matters is what I'm doing right now and who I'm becoming. I credit EO a lot for helping me let go of that pressure and actually embrace my name as a gift and a privilege — then simply architect the life I want to build. That's really been the work, and it hasn't always been easy.

The Hustle That Launched a Career

Aaron: Tell me the story of how you got your first job out of school — the trip you took to New York — because it says so much about your character and foreshadows so much of what you've gone on to do in your life.

Russell: I studied abroad my junior year in college and had the privilege of landing an internship at a Swiss private bank in London. It was really my first real taste of the professional world, and I got to interact with a remarkable group of people.  When I got back to school, I knew I wanted to work in investment banking in New York. But Wall Street does not come to UC Santa Barbara. I called my dad over winter break my senior year and said, "Dad, I want to work in investment banking. I don't know how I'm going to do it, but I need to go to New York and meet people." So I went. I hustled — got a bunch of informational meetings, sent follow-ups relentlessly. I think a few firms took notice: who is this kid from Santa Barbara who wants it so badly? Do you know how many offers you really need to accept a job on Wall Street? One. And I got one.

Aaron: And how did taking that job change your life?

Russell: Working in investment banking builds a strong professional foundation. It teaches you classic finance skills, the language of business — which is accounting — and a tremendous amount of grit and resilience, because you're expending enormous hours doing hard and stimulating work. It teaches you about the power of community, because you're going through it alongside a cohort of peers. It teaches you about competition, because everyone around you is a high performer. And it gives you a vista of what's possible — you're exposed to enterprise that has achieved real scale. As a 22-to-24-year-old, that's an incredible launchpad

From Banking to Building: The Entrepreneurial Itch

Russell: I worked in banking for two years, then moved to California and spent about five years in private equity and working directly inside a portfolio company. I worked for a firm in Los Angeles that had acquired a healthcare services business. There was a division focused on sleep health — sleep apnea, quality of rest — that I found particularly fascinating. It seemed like an exciting, emerging area of medicine.  Around that time, my wife and I were expecting our first child and decided we didn't want to raise a family in Los Angeles. We wanted to move to Seattle. There was an opportunity to join a private equity firm here called Bluepoint Capital, which is a great firm. But something was burning inside me: I don't think I've earned the right to sit on this side of the table and opine on whether a business is good until I've been on the other side and built something myself. So I left.  I walked out with a healthcare sleep idea and told myself: what's the worst that can happen? It doesn't work and I go find another job. These other guys built this — I'm smart, I'll figure it out. No problem.

Aaron: Oh my gosh.

Russell: Right. So — no salary, a laptop, and a cell phone, trying to build a comprehensive sleep medicine company where we employed physicians, contracted with Medicare, and ran diagnostic and therapeutic services out of Phoenix, Arizona, while I lived in Seattle. We had to raise money. But at its core, this was about proving something to myself: that I could build enterprise value. That I could be an operator. That entrepreneurial journey began in 2005, and it's 2026 — so there's been quite a through line since.

Health, Wellness, and the Design of Business

Aaron: Alongside entrepreneurship, there's also been a focus on health and wellness in your story. Is that a deliberate professional focus?

Russell: Not today — it's not where I'm spending my professional time. There was a period where it was, when I was in the sleep business with this mantra of improving the lives of 10 million people in 10 years. But it's easy to get disenfranchised with healthcare broadly. The foundation of our healthcare system is so broken that if you want to be a disruptor, you're budding up against an enormous amount of resistance to change.  What I learned about myself over time is that I like solving interesting business problems. I like the design of business — bringing a group of people together under a purpose and architecting the organization in pursuit of something together. That's what energizes me, not necessarily the specific problem domain.  Personally, I remain deeply committed to health and wellness because that's where my energy originates. EO has also been a big driver of that investment. But professionally, I've moved on.

Every Move: A Health-Tech Chapter

Aaron: You exited the sleep business in 2009 — a technical exit, as you've described it. What came next?

Russell: I don't think I was particularly intentional after that. Frankly, I was scared. I was still in the zone of: Russell Benaroya needs to show up and have it all together. I was so anxious that I raced fairly quickly into another healthcare opportunity — which I'm glad I did — but if you pinned me on what I was trying to design for my life, I'd say it was more circumstantial than intentional.  The next business was a technology platform — the best way to describe it is a mileage rewards program for your health. This was at the height of the tracking device boom: Garmins, MyFitnessPal, MapMyRun. We wanted to create a consumer experience that let you connect any device or app and then get rewarded by your health plan or employer for actually doing things that improved your health. Prevent, rather than treat. We got meaningful interest from health insurance plans, got a boost from participating in Techstars here in Seattle, and in 2017 we sold Every Move.  It did not change my life financially. My business partner and I separated after the first few years — a lot of learning there. We had about 30 employees by the end. Crazy ride. The lesson I now give to anyone starting out: before you write one line of code, do 100 customer development interviews. Understand whose problem you're solving, how big it is, and what the single feature would be that makes them say yes. You can build a really cool product that doesn't match the core market need, and then it's very hard to unlock traction.

The Enneagram Three and the Art of Vulnerability

Aaron: I've heard you describe yourself as an Enneagram Three — achievement-oriented, but also wanting to please people. Raising money and managing investors seems like it would create real tension for someone with that profile. Was delivering hard news to investors difficult for you?

Russell: The thought that came to mind is board meetings. I wanted to arrive at every board meeting perfectly buttoned up — presentation tight, problems already anticipated, everything organized. I was protecting myself. I wanted to showcase that I had it all together.  But here's what I've learned: the real value in a board relationship comes from sharing the hard thing before you even get to the meeting. Show up with the one challenge you're genuinely struggling with — a personnel issue, a customer segment, a product question — and let them help you. That's vulnerability in service of growth.  It's taken me a long time to be able to say, "I don't know. I'm struggling." When you have investors, you assume they invested because you have all the answers. But that's not why they invested. They invested because you're curious enough to look around corners and wonder what's possible. The story I was telling myself — that I had to be buttoned up — was completely made up. And it wasn't serving me.

Before we continue, I want to tell you about the community that made this podcast possible — the Seattle chapter of EO, the Entrepreneurs' Organization. It's not networking, it's not selling to each other. It's real entrepreneurs sharing real challenges and solutions. If you have a business that does at least a million dollars a year in revenue and you're curious about joining a community that gets what you're going through, check out EO Seattle.

Costa Rica: Designing a Life on Purpose

Aaron: Is it after Every Move that you moved to Costa Rica?

Russell: Yes, we moved in 2018. The impetus came from a lack of intentionality in my life. I remember two moments clearly. The first: I came home with another great startup idea, and my wife looked at me — knowing everything we'd been through — and said, "Are you kidding me?" I got defensive, but she was right to push back.  Shortly after, we were driving home from Bend, Oregon, kids in the back, listening to a Tony Robbins podcast about three steps to a breakthrough. We're driving through the Cascades and I turn down the radio and say, "Why don't we ever talk about where we want to be in five to ten years?" She said, "Because it's never been about us. It's always been about you, and we've been along for the ride."  That was a pivotal moment. It cascaded into some very difficult conversations, and eventually we worked with a coach who told us to go on a first date. On a first date, you're curious. You lean in. You want to know this person. And what we kept coming back to was this dream we'd talked about for years — having a real abroad experience with our kids. The coach asked: where would you go? I said Costa Rica. He said: why can't you? I said, I guess I don't actually have a job right now. He said: so go.  The first call I made was to the president of EO Costa Rica. He said, "Bring it." At the end of June, we moved there with our kids.

Aaron: You were there for a year?

Russell: A year. We could have stayed longer — it takes time to build friendships, buy a car, find schools. But our kids were ready to come home, and we honored that.

Finding EO: Not Being Alone on an Island

Aaron: You've been in EO for 19 years. What brought you here?

Russell: In 2007, I had lunch at a pub in lower Queen Anne with an EO member named Adam Brotman — who has gone on to do some remarkable things. He asked how it was going. I told him I had investors who were challenging me, a steep learning curve, a lot of unknowns, and I felt really alone.  Adam said: "Russell, you have to join EO. It's the place where you realize you are not on an island." And then he shared his own journey — the struggles, the fears, the moments of feeling lost. My reaction was: that's exactly what's happening to me. I joined immediately.  Those first several years were a massive catharsis. All that suppressed emotion, all that fear, all that self-protection — it just started coming off. There was so much feeling in it. It was really the beginning of a journey of self-awareness that continues today, and I'm deeply grateful for it.

Aaron: How has being in EO changed you?

Russell: I like to say that EO has given me the wings to fly — confident enough, though not always, that I will land. The move to Costa Rica was a perfect metaphor: a real deviation from the plan, full of unknowns. And the universe conspired to make it extraordinary, maybe because we were so open to it. I was more creative during that year than I'd ever been. That would not have happened without EO.  Beyond the big moments, EO is about punctuation — helping clarify the small moments that build self-awareness over time. When you surround yourself with peers who are living the same kind of life, the waves start to mellow. EO becomes a source of calm in the storm. At a forum level and in a leadership role — I served as membership chair for a few years — it's just about what you choose to make it at any point in your life.

Aaron: I'm in EO because of you. You met me for coffee and described EO in a way that made me trust it. So thank you for that.

Russell: Thank you.

Stride: Building a Back-Office Business from Costa Rica

Aaron: You came up with another business idea while in Costa Rica. What was that?

Russell: That business was not my idea — it was a partner's idea. And it had nothing to do with healthcare; I was ready to move on. This was a back-office financial services business: bookkeeping and accounting.  I didn't know exactly what I was going to do in Costa Rica, so I was open to possibility. And there's real power in being willing to say yes — as long as it's in alignment with your principles. The idea was to leverage my presence in Costa Rica as a nearshore source of accounting talent for US-based businesses. Costa Rica is a well-established nearshore market — same time zone, high proportion of English speakers.  We ended up buying a US-based accounting firm and experimenting with nearshore accountants in Costa Rica. We ultimately found the Philippines was a stronger talent market for what we needed. So the fact that I was in Costa Rica ended up having no direct bearing — but it sparked the curiosity. I was classically finance-trained, I knew accounting, and I genuinely wanted to help other entrepreneurs unlock the financial intelligence of their businesses. That's a powerful contribution.  My partner Eric Page served as CEO — that was the right fit. I wasn't interested in being in the seat. The business really came into its own during COVID: fully remote workforce, perfectly positioned to help clients navigate EIDL loans and government assistance programs. I was active through about 2022, and then we sold it. A fine outcome.

Today: Empowering Entrepreneurs at Timberland Partners

Aaron: And today?

Russell: I'm continuing this theme of empowering entrepreneurs to achieve their highest and best use — which has really been the through line. That was the driver behind the book I wrote after Costa Rica: One Life to Lead: Business Success Through Better Life Design. The core idea is that we are the architects of the lives we want to create, and as entrepreneurs, it's remarkable how often we construct cages for ourselves — even though freedom is supposedly the whole point of entrepreneurship.  I had been coaching some business leaders here in Seattle, and there was one organization that was clearly on the cusp of a real breakthrough: Timberland Partners, a real estate investment firm focused on multifamily apartment acquisitions and development. They had built an admirable foundation and saw the opportunity to accelerate. What I saw in the founders was a genuine "why not us?" mindset.  I've learned that there are two kinds of entrepreneurs: the "Let's go to Mars" type, and the "Let's build the system to get to Mars" type. I'm the latter. I love when someone says, let's go to Mars — it gives me enormous energy. And then I want to build the architecture that makes it possible. Timberland needed that — so instead of continuing to coach them, I joined as their COO. It's been a remarkable few years of transformation, and they've established themselves as a genuine regional leader in multifamily real estate.

Running 200 Miles: The Philosophy of Endurance

Aaron: Do you mind if I ask you about running?

Russell: It's my favorite topic.

Aaron: You run extraordinary distances. Describe the types of races you run.

Russell: I'm currently training for the Tahoe 200 — a 200-mile race around Lake Tahoe happening in June. Before that, most recently, I ran the Marathon des Sables in Morocco in April 2025: a 150-mile, six-day stage race through the Sahara Desert where you carry everything — gear, food, sleeping bag, emergency kit — and they provide shelter and water. I've been running trails and endurance events for as long as I've been in EO. It's fully integrated into my life, and it's been a profound source of learning. At those distances, it becomes meditative. Weird things happen in your head when you're out for 30 hours.

Aaron: What do you get from running 70 miles that you don't get from running 26?

Russell: There's a race I did in 2021 during COVID called the Cascade Crest 100 — starts near Hyak, about 30,000 feet of elevation gain. Five or six hours in, around mile 30, I couldn't keep any food down. Major GI distress. I was seven hours into a 32-hour event with 25 hours left.  What you get from 70 miles is a visceral recognition that you are simply a machine. If you can get energy in, you expend energy out. When you can't take in nutrition, you're feeding off fat storage, and decisions become everything. How do you slowly coax your GI system back? A little broth. Some pickle juice. A nibble of noodle. Am I getting blisters? Am I using my time at the aid station wisely? It's getting dark, you put on your headlamp, and all you see is that beam of light for hours while you're alone in your own head.  It becomes mission control for your body — and in a way, mission control for your life. Because in that moment, you rely only on yourself. And then, once you push through that pain cave, the sun comes up. You feel better. Someone makes you laugh for a second. A whole new vista of possibility opens up. The metaphors for life have been very prominently displayed at those distances.

Aaron: Does breaking through the pain cave — doing things that seemed impossible — give you portable courage for the rest of your life?

Russell: Yes, with a footnote. For some period of time after an event, you feel enormously capable and grateful. But 99% of our moments are not like that, and it's worth asking: what am I chasing? There's ego in signing up for these things — I won't pretend otherwise. But the event itself is just the endpoint. What really matters is the months of disciplined, boring daily preparation. Five to seven AM, every day — not glamorous. That's where durability gets built. The running is just how I've manifested it. We all have our thing.

Training Like an Athlete, Leading Like a Coach

Aaron: What does a training week look like for someone preparing to run 150 miles?

Russell: About 50 to 70 miles a week, with intentional variation. I have a coach now, and many of my runs are what she calls recovery runs — almost walking pace — because she's trying to build my engine, my VO2 max, my ability to process oxygen efficiently. The goal is a diesel engine, not a high-octane sports car. You need diesel to go the distance.  This idea that you should go boringly slow so that you can go long has been a real revelation. Before, I assumed that unless I felt wrecked after a run, it wasn't a good workout. But it's not about optimizing any single session — it's about optimizing the arc of training for the event. A couple of runs a week are purely recovery-based. A couple are high-intensity intervals: short bursts, heart rate up, then recovery. That variation matters, and I just follow the script she gives me. It's genuinely nice to turn off your brain and trust someone else's expertise.

Aaron: You clearly have a long history of recognizing the value of coaching. Do you have a personal coach?

Russell: I do. And EO is coaching in its own right — the forum experience is a form of structured peer coaching. But I leveled up to an individual coach, which felt like a natural progression.  One moment stands out. I was going through a stressful business situation involving some litigation. I called my coach, genuinely anxious. He said: go to your conference room, close the door, turn off the lights, close your eyes. I did it — felt odd. Then he said: imagine bubbles floating around you. Each bubble is a thought. One bubble contains a thought about your current situation that is scaring you. See it. Now let that bubble float by.  Then he said: there's another bubble with the same facts. But the thought in this one is completely different — it gives you energy. It reframes the fear into something less frightening, maybe even motivating. Grab that bubble. That bubble is no less true than the one you let go.  That was my first real realization: thoughts are just thoughts. They're not us. We don't have to grab the scary one. And the other thing that's stayed with me: live your worth, don't prove your worth. You are already worthy. That axiom has been incredibly meaningful every time I feel the instinct to perform before I've earned the room.

Who Are You Becoming?

Aaron: When I say you're intentional, I don't mean you have a master plan. I mean that how you show up — in whatever circumstances — is thoughtful and deliberate. With that in mind, one final question: who are you becoming?

Russell: I'll blurt the thought without overthinking it: I'm becoming free.  There's a book that's been meaningful to me — 15 Commitments of Conscious Leadership. It talks about our three greatest needs: security, control, and approval. We spend so much of our lives sourcing all three from outside ourselves — I don't have enough money, I need to be liked, I need to be in control. Freedom, to me, means letting go of the need to source any of those things externally.  I have all the security, control, and approval I will ever need — and that has nothing to do with running a company or with what people think of me. I am clear on that. And because of that, I am free. And when I am free, the universe conspires to support how I authentically want to show up in the world — just like it did in Costa Rica.  That's the work. And I don't know if it ever ends. But I'm learning to enjoy tackling it, without beating myself up for not being there yet.

Aaron: I think that's a beautiful way to end. Thank you for this.

Russell: Oh my gosh. Thank you. This was a real gift.

Aaron: Likewise.

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