Episode 15 - It's All the Same Problems, Just More Zeros
With Michelle Bomberger

Join host Aaron Burnett as he sits down with Michelle Bomberger, founder of Equinox Business Law Group, to explore how curiosity, optimism, and a business-first mindset shaped her entrepreneurial journey. From growing up in Panama to building a law firm designed for entrepreneurs and leading EO Seattle as Chapter President, Michelle shares the leadership lessons, pivotal decisions, and community that have defined her path.

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 Between Two Worlds

Aaron: I don't think I've ever started with this question. Tell me a little bit about your childhood. You grew up in Panama.

Michelle: Yeah, it was a very unique experience. The US controlled certain land on either side of the canal — that included the canal itself, run by the Panama Canal Commission, a US government organization, and then the military bases as well. There were probably ten, maybe fifteen military bases. The Americans there were a mix of second and third generation Americans who stayed — typically they came down to help build the canal, married a local person, and stayed. A lot of my friends came from families of American fathers and Panamanian mothers. And then you had the military families who came in and out every three years or so. And then folks like my family, where my mom moved to Panama in her early twenties after nursing school. She and her best friend decided they were going to go abroad, applied for jobs in various places, and landed in Panama only a few years after the anti-American riots. I can only imagine what her family thought at that time.My father was stationed there in the Army, retired there, and worked for the Smithsonian managing one of their tropical research islands. They have a huge tropical research institute in Panama. So they met there. Being what I would call kind of first generation Zonian, I've always felt a little bit out of place. I don't have all that Panamanian history and tradition. I don't have all that Zonian history and tradition — sort of plopped down in the middle. And surrounding all of that is the Panamanian community. You could very much be insular, very much choose not to participate. We did a lot more out in the city and community because of the horses. I rode horses growing up, and we had to go get feed, shavings, all that kind of stuff — always to these random warehouses out in the community. It was a really diverse community from the types of people who were there.

Michelle: And yet still so American. I went to Department of Defense schools. The Spanish I learned was the basics — "It's the holidays. Here's the word for witch and pumpkin." It wasn't the integrated bilingual environment you might expect. I give my mom a hard time because we had hired help growing up and she never had them speak Spanish to us. What in the world? I just went back for my 30th high school reunion and I'm still super self-conscious about my Spanish, which is adequate — but not anywhere near where it should be.

Aaron: What do you think you got from growing up in Panama that is different from having grown up in the US? How did it shape you?

Michelle: I think the diversity of the people. It was very much a small town — all the Zonians, whether multi-generational or first generation like my family, everybody knew everybody else's business. And on top of that, there was this entire foreign culture, a different culture. Navigating those two things — both in school, where we had a mix of different groups, and out in the community, where you shifted how you behaved based on the environment — I think that really did teach some flexibility and adaptability.

Aaron: I can see that. And is it university that brought you back to the United States?

Michelle: Yeah. My experience before that was my mom, as a US government employee, got six weeks of vacation every year. We basically took them all at the same time, came to the US to visit family, did all our clothes shopping for the year, got ready for back to school. But other than that, that was my only experience in the US until I moved to college.

Aaron: So it was a relatively new experience to come back.

Michelle: It was. I had a lot more experience traveling in the US than anywhere else growing up. I grew up in Central America, but we didn't travel anywhere in Central America or South America. All of our vacations were to the US. We'd bring two empty suitcases and fill them up with all the stuff for the year — the PX, the commissary, some things on the Panamanian economy.

The Long Road to Law School

Aaron: When you went to university, did you know that you wanted to be an attorney?

Michelle: No, although there is a snippet from our senior year newspaper where they were asking people where they were going, and the quote from me was that I was going to be a corporate attorney making the big bucks.

Aaron: So you had some idea.

Michelle: Evidently. I don't know that I would have been able to tell you that four years later when I was at university, but I got a degree in finance with a minor in computer applications — kind of an MIS degree, so you learned some coding, some database management. It was really setting me up for consulting or knowledge work environments.

Aaron: And then I saw you got both a JD and an MBA from Northwestern.

Michelle: I did. Over-educated.

Aaron: I don't know about that. Did you do them simultaneously?

Michelle: I did. After college, I worked for two years at Ernst & Young in their management consulting practice — process and technology, mostly at Fortune 500 companies. My favorite client was the City of Albuquerque. They'd had a couple of different companies come in to help them implement a system and they just weren't successful with it. When we came in, it was really a different experience because they actually valued us being there, versus most Fortune 500 companies where consultants come in and they're kind of like, "Just leave us alone."

Aaron: You've arrived to mess things up.

Michelle: Exactly. That experience with that particular client is what made me think about going back to school. I really wanted to work with smaller companies that needed that support, that needed guidance, consulting, and valued it. When I was applying to school, I was actually applying to business school. Northwestern had the combined JD/MBA. At the time, most schools had it set up that you could apply to both and if you got in, great. Northwestern's was one of the only ones that was truly a combined program — combined application, combined financial aid. It really resonated with me as a program that could give me more tools. I never really expected to be a lawyer. I expected to be a consultant with a legal toolkit that would be a differentiator — a way to add additional value going into those conversations with clients.

Aaron: It sounds almost like you had an entrepreneurial disposition even going into getting that education.

Michelle: Yes. That was the vision. I was fortunate when I left Ernst & Young — right before I went back to school — there was a very small window where an Ernst & Young partner who had left asked me if I'd be interested in joining her for a four-month period between when I was finishing up and when I was going to school. It was lucrative, and it was the first time I'd set up an entity to do consulting work. So it was there.

[ SPONSOR BREAK ]

Before we continue, I want to tell you about the community that made this podcast possible — the Seattle chapter of EO, that's 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 a year in revenue and you're curious about joining a community that gets what you're going through, check out EO Seattle.

The Dot-Com Dream and the Leap That Followed

Aaron: How quickly after graduating law school did you establish Equinox? You're in your twentieth year, twenty-first year?

Michelle: We're just finishing up our twentieth year. Again, my plan was not to be a lawyer — my plan was to be a business consultant working with smaller businesses. But during law school, it was the dot-com boom. The business-focused lawyer was really appealing to some of these boutique dot-com law firms. So I ended up taking a role with one that worked with .com companies. It was really exciting — such a cool, exciting time. And I graduated in 2001, just as the bubble was bursting. They deferred all the job offers, then September 11th happened, and then they cut all the job offers. So I never actually went down that path — and maybe that was fortuitous.We had moved to Seattle because I had taken a job here in Kirkland. We bought a house. I'd taken the bar exam, and my husband moved out here at the same time. We had just gotten married, he had just graduated from school, and within fifteen minutes he got a job offer and mine was rescinded. Literally fifteen minutes between those two calls. We decided to stay, so we're still here.I was at AT&T Wireless for a couple of years in their internal audit group. That was really rewarding because it exposed me to parts of business I'd never seen before. When I think about wanting to be a consultant for smaller companies, I had my consulting and technology experience from Ernst & Young. The internal audit function at AT&T was really focused on processes across the business — customer service, collections, marketing — all these different areas in depth. AT&T really gave me that.I was fortunate again to work for a vice president who was really empowering. She really believed in me. I had my first child that year and said, "Well, I want to be part-time," and she said, "Just do what you need to do. You'll get it done." She was really flexible and empowering, and that made a huge difference in my confidence. That work put me in front of executive vice presidents — doing readouts of audit findings at a very, very high level. The public speaking and the exposure to bigger business issues was really, really valuable.

Michelle: In 2004, Cingular acquired AT&T Wireless. We weren't sure what they were going to do with the Redmond operations. Do we sit around and maybe wait for a severance? The VP I worked for said, "You've talked about the law firm. Maybe now is the time." So that was the launch. I had a one-year-old at home, a lot of uncertainty around what was going to happen with Cingular, and as many professional services businesses are, it was safe enough to throw the spaghetti on the wall and see if it sticks.

A Law Firm Built for Business

Michelle: The vision was modeled after Northwestern Law School's small business clinic. Northwestern was the first law school to launch a corporate transactional clinical experience. Many law schools have immigrant rights, juvenile defense, capital defense — litigation-type environments. To have something more corporate, more of a practical experience, was relatively unheard of. There was actually a bunch of JD/MBAs who said, "Hey, let's start this thing." I modeled it loosely after that, with a very non-creative name: Small Business Legal Services. Because it was never going to be the Bomberger Law Firm — nobody knows what that is. It was descriptive, not creative, and it did the trick as a starting point for who do I want to be talking to, what kind of work do I want to be doing.The foundation then is very similar to what it is now: business-focused conversations, not legal conversations. How do we start with the operational and business side? They get to the legal piece, but that's not where we start. Fixed fees and transparent pricing as often as possible, and real transparency and responsiveness. We need to move at the same speed the business needs to move at. One of the barriers to engaging legal help is waiting three or four weeks without hearing from your lawyer. We need to remove that friction.

Aaron: Full disclosure for anyone listening — we're a long-term client, and I would say it's as close as you can get to having an attorney on staff as part of your leadership team, with that same relationship and responsiveness.

Michelle: We're grateful for that. For us it's a bit of vicarious living through the cool stuff our clients are doing, but also really empowering that relationship. Most smaller companies don't have that. There's always this friction around, "Should we call for this? We can probably figure it out. Maybe we can Google it. Maybe we can ChatGPT it." What if we remove that friction and just said, "Call the expert — it's built into the plan"? I think that's empowering for clients, and it's certainly empowering for our team because we know the clients well enough to have meaningful conversations without worrying about the clock. It's been a definite journey over twenty years to get from where we started, but it's also really fun to see that magic happen.

Finding EO — From Accelerator to Chapter President

Aaron: What brought you to EO? You've been in EO coming up on six years?

Michelle: Yes, and two years in Accelerator before that.

Aaron: And really rapid and intense engagement — this year you've been president of the Seattle chapter.

Michelle: I have been. And Aaron's on the board this year as well. I think it's been such a strong community within the board — really clear goals and moving together. That's one of the things we talked about at the beginning of the year: how do we break down the silos of board chair roles and really work together toward the common initiatives across the organization? I feel like that's something the board has done really, really well this year.

Aaron: What brought you to EO initially?

Michelle: I've always appreciated peer leadership groups. I've been in them on and off over the years, or had business coaches — it's just something I really value. I'm one of those people who likes to talk things out and work things out. I need that space. I had been in a business builders group, and then we moved to Ireland for two years, and then I was in a Vistage group for a couple of years. I knew lots of people in EO. If you're in the entrepreneurial community, you hear about it. But I hadn't hit that magic million-dollar number, so EO wasn't on the table. When I heard about Accelerator — the program for businesses looking to scale to that million, that have an established base but need some of those technical pieces to get there — it really made sense for me.And when I compared it to what I was getting out of Vistage, it made a lot of sense. Practically, and also from the peer group. When I joined Vistage, I was in a trusted advisor group — other professionals, about half of them owners — versus the CEO group I was really looking for. The success of Vistage is really driven by the facilitator, and we had some transition in that. The timing worked out well. Talking to people in EO, Accelerator being an option, where I wanted to take my business — it was just the right time with the right toolkit.

It's All the Same Problems, Just With More Zeros

Aaron: What have you gotten out of EO? How has EO changed you?

Michelle: In the Accelerator group, our EO member facilitator said something I've never forgotten: "It's all the same problems, just with more zeros." As you're navigating the fires every single day, there's real humility in recognizing that we are all experiencing similar things — regardless of whether it's a $50 million business or a $1 million business. The problems are quite similar. As a leader, the way you decide to tackle those problems, the way you decide to lead, is not so dissimilar. We're all learning the same tools, techniques, and tactics.Being in a room where everyone is there to be a better leader — where we self-select in because of the core values, because of the idea that together we grow, we think big, we be bold, we trust and respect — those things are at the core of who chooses to be in that room. I've learned so much from being in rooms with leaders who behave that way and value those same things. Sometimes it's just the repetitive nature of, "Oh yeah, I've heard that before," and the storytelling of experience shares in EO helps us say, "They've been there, and that's a similar experience." You're not alone — not in the sense of feeling lonely or not knowing how to figure things out, but in the sense that there's a whole community of us doing the same things, rinse and repeat, trying to be better, failing sometimes, succeeding sometimes. Having a space for that is a huge value of EO.

Loyalty, Optimism, and the Blind Spots of a Leader

Aaron: I get the sense that there is a unifying belief structure — a philosophy that animates your life, your professional life, your personal life, decisions you've made with EO. What is that?

Michelle: I think loyalty is a big one for me. And I think that's partly why I struggle a bit with being a leader — you've got some of the trying to make people happy, trying to be a loyal friend, partner, boss. That's core to what I value. I see that in EO as well: we are a tribe, or a cult, or whatever term you'd like to use — loyalty to each other is really valuable, and that wraps around that core value for me.Another is optimism. I tend to be an "it's all gonna be fine" kind of person. My husband still laughs about a particular movie we went to that he was going to walk out on, and I said, "It's gonna get better." Same thing with books. I'm getting better about putting a book down if it's not working. But I do think being an optimist is a superpower for me. I think it drives me toward being more human, more confident, seeing the glass half full and the opportunities out there. It's also a blind spot in so many ways, and as a leader I've been learning how to calibrate that — because I tend to go full speed with optimism and positivity.

Aaron: I think there are two other things that come to mind. One is that you're very principled and steadfast in those principles, and the other is that you're very inclusive.

Michelle: Thank you for that.

Curiosity Unleashed — A Theme for the Times

Aaron: This year's theme has been Curiosity Unleashed. Why that theme? What led you to it?

Michelle: One of the most impactful and powerful characteristics I see in EO is curiosity. I think about a forum mate of mine — when we're on a forum retreat, meeting businesses or other business leaders, it's just question after question, curiosity after curiosity. I wanted more of that from myself, and I see it in our community — in the formal things we do, the learning events, the social events, opportunities to learn and be curious, but also just in conversations with each other. Really leaning toward: what can I learn from you? What can curiosity open?I think curiosity is also really powerful in breaking down barriers. If we lead with questions, we might learn something we didn't expect, and that helps break down judgment. For me and where we are right now as a community and as a country, breaking down barriers through curiosity is a really, really impactful tool. The "unleashed" part — I did a whole bunch of different versions. Curiosity Ignited. Trying to find it. And I love it. I'm really, really thrilled with how it's come together as a theme and how we've carried it through the work we've done this year.

Aaron: I think it's been great — and a timely theme, as you said. Thank you for talking with me.

Michelle: Yeah.

— END OF TRANSCRIPT —