Mike Personick: Dirtbag Entrepreneur

Two interviews in a row?! Why the hell not? This week I am exceptionally pleased to bring you this thought-provoking interview with Mike Personick. Mike is a 5.14 rock climber, husband, dad, and former business owner. And now, like me, Mike is living the financially independent rock climber life.

In this interview we delve into the early days of Mike’s climbing in tandem with a remote job. We learn how Mike managed to become a nails-hard climber while simultaneously honing a craft that led to a breakout business, and in time, a lucrative buyout. We hear Mike’s fascinating story of meeting his future wife and traveling in Europe for a year, eventually adding a third human to the equation. Perhaps most importantly, we discuss the simple investing methods that can build financial freedom for us all, as well as the psychological challenges that can topple any kingdom.

Read this one all the way to the end. Mike delivers.

Mike Personick locking off in Red Rock, NV.
Mike Personick locking off in Red Rock, Nevada.

An Introduction: Mike Personick

The timeline bounces around a bit in this interview, but I’ll do my best to lay out Mike’s story. Today, Mike has achieved financial independence. Along with his wife Rayna and daughter Mika, Mike now designs an ever-changing life of travel and pursues the passion of rock climbing, all the while knowing that his human capital is far from spent at age 43.

Mike’s story as a climber begins at age 22 in the Washington, DC area. Shortly thereafter, Mike is working a corporate software engineering job when he begins to feel the incredible pull of life out west. Preparing to leave the company and find another job after resettling, Mike is unexpectedly offered a fully remote position with his current company. It doesn’t take long to realize that his job obligations can be fulfilled anywhere on the globe. Thus begins Mike’s multiyear siege on rock climbing ambitions, meanwhile building his craft of software development.

(Related Post: Mike Doyle: A Remote-Controlled Climbing Life)

Investing for the Future

In the ensuing years, Mike begins investing his growing savings. After discovering the Bogleheads forums, Mike realizes the immense power in passive index fund investing. It’s a topic we explore in great detail below.

Eventually, Mike, along with a former coworker, form their own business. This business fills a niche for the massive Amazon monster, and they are happily gobbled up. Mike sticks around in a Seattle office for three years to assist in the integration. The company buyout, in tandem with his success with his personal investing strategy, lands him a podium spot on the pedestal of financial independence.

Let’s see how Mike is using his new-found power.

Mike Personick: The Budding Obsession of the Climbing Life

[Climbing] took over my life and has guided pretty much every decision I’ve made since.

Mike Personick

Mike: I was in the first generation of climbers to come to the sport through a climbing gym. I grew up in the Washington, DC area (Northern Virginia) and had never even heard of rock climbing. The first time I put on a pair of climbing shoes was when a close friend, Ken Haller, took me to Sportrock Alexandria in 1999, when I was 22. However, climbing didn’t immediately grab my attention, and I didn’t really get the bug until two years later in 2001. Then it took over my life and has guided pretty much every decision I’ve made since.

Preferred Style

I love to sport climb and boulder. As a former gymnast, I have always been drawn to the strength and movement aspects of climbing. I especially love the complexity involved in performance sport climbing. I would describe myself as a focused and accomplished everyman climber.

The Home Base and Yearly Travels

My wife, our 4-year-old daughter, and I live in Southern Utah, just outside of St. George. We just moved here less than a year ago. To escape the heat this summer, we rented a house in the valley just outside of Maple Canyon. It wasn’t our first choice for a summer trip, but you know, COVID. I’m happy just to be able to climb at all given the state of the world. 

I just finished up a pretty cool project here in Maple – the Compound Triple Crown. This is just something I totally made up as a challenge for myself. It consists of three classic James Litz routes at the Compound – Defcon 1, Close Quarters Combat, and Cyanide Suicide. I belayed James on these when he did them back in 2011. Although one of his pinkies is stronger than my entire body, I thought it would be a cool challenge for me to try to do them all in a summer, like he did. It was an outrageously fun and unique experience trying to do all three at the same time, sometimes climbing on all of them in the same day. So much rad terrain and movement. I’m a little sad it’s over. 

Mike Personick high in Maple Canyon, Utah.
Mike Personick high in Maple Canyon, Utah.

Mike Personick on Travel Logistics

CC: For either remote work or simply “early retirement,” how do you and your family manage extended travel away from home? How has that changed from your single years?

Mike: In 2004 I was working in a corporate software engineering job in the DC area. Realizing I needed to move out west to properly focus on my climbing, I figured I would just find another job when I got there. So, when I went to tell my boss that I was quitting and moving to Salt Lake City, I was a little surprised at his suggestion to work remotely. This was a new concept for me at that time. 

It actually took me a while to figure out that working remotely meant I didn’t have to be in one place all the time. I could vagabond around and climb like the full-time dirtbaggers but still keep up the semblance of a career. There weren’t many of us climbers doing this back then. We didn’t have a good model of how to do it and we were trying to figure things out on our own. 

(Related Post: Keeping Remote Work in a Post-Pandemic World)

An Evolving Remote Work Life

At first I kept it pretty simple and spent most of my time climbing in Salt Lake. I only traveled during the snowy winter months to guide at Hueco Tanks. There were a few other guys that had a situation similar to mine, so we all rented a crappy house together on a six-month lease in East El Paso. No furniture really, just some air mattresses and folding tables. It was basically indoor camping. 

The first year we did this was the winter of 2005-2006. When I called my friend Sam for directions and how to find the house (no smartphones back then), he told me to look for the house with no numbers and an upside-down pentagram in Christmas lights on the roof: “The House of Doom,” as we called it. We had Ben Moon and a couple of Brits staying with us that winter, along with Dave Graham and a number of other interesting characters that passed through. It was quite a scene. 

The Road Trip Circuit

Mike: This went on every winter for a while. Eventually, I got a little bolder with my expeditions and started mixing in other areas to my annual winter trip. As time passed, I found a flight path that I really enjoyed and repeated for a few years: the Red River Gorge in October/November, then bouldering in Chattanooga in December, followed by Hueco Tanks in January/February, finishing in Bishop in March.

As a single guy my comfort needs were quite low. I was happy to share cabins and houses with other climbers or stay in crappy extended stay hotels. Only in Bishop did I actually try to stay in my van and work in a coffee shop. In the end, the coffee shop model was not a productive environment for me and I gave up. 

Thinking back on all this I have no idea how we made it all work. Things are so much easier these days with Airbnb.

Rayna and Mike Personick.
Rayna and Mike Personick.

Mike Personick Finds Tufas and Love in Greece

CC: Your wife, Rayna, is from Bulgaria. Tell us the story of meeting Rayna in Kalymnos and how that led to an extended period of travel in Europe.

Mike: In late summer of 2011, I was pissed off at the world for one reason or another and decided to buy a ticket to Kalymnos on a whim. A few friends from Salt Lake were going there and said I could tag along, a week before departure. I had never climbed outside the US before except for a short trip to Potrero Chico years earlier.

On the first day of the trip, I was wandering around the Grande Grotta when I looked up and saw this amazing climber onsighting one of the harder routes there. I was pretty impressed and intimidated. I remember she was wearing blue climbing pants that had a pink hand-print on one side of her butt. 

On day two of the trip I ran into Ms. Hand-Butt again at the Spartacus wall. This time we ended up having a conversation. She wanted to try the same route that I was trying. She told me her partner (who I had mistaken for her boyfriend) was leaving the following day, so I swooped in and generously offered to climb with her if she needed a replacement. 

We ended up climbing together every day. At the end of the two-week trip it became obvious that we both wanted to keep things going, so I ended up staying in Europe with her for the next year, traveling and climbing. I wouldn’t be able to do it justice with words what an amazing adventure this was. It was the best year of my life, all possible because of remote work. In Fall of 2012 she moved to the US and we got married.

Mike Personick crushing in the Hurricave, near his home in St. George, Utah.
Mike Personick crushing in the Hurricave, near his home in St. George, Utah.

Mike Personick on Building a Career in Software Engineering and Remote Work

CC: Can you give us a background of your career, how you eventually moved to remote work, and then the eventual sale of your company?

Mike: I decided to start a software business with a guy from the DC company in 2006. At first it was basically just a consulting firm.

Over time, however, we began to grow and accumulate enough intellectual property to make the business valuable on its own. In 2016 we were approached by Amazon. Amazon had a hole in their cloud computing product portfolio that they felt would be easiest filled via acquisition. We sold the company to them, and all of us moved to Seattle to help them get our tech integrated and running.

(Related Post: The Fallacy of Happiness and Meaningful Work)

Returning to In-Person Work in Seattle

Mike: We had kept things almost entirely virtual for those 10 years pre-Amazon, with only two of our employees working in an actual office (their choice). So moving to Seattle to work for Amazon was my first time back in an office environment since leaving DC for Salt Lake City in 2004.

Working for Amazon was an overwhelmingly positive experience for me, and I truly love Seattle. Seattle will always have a special place in my heart, but the full-time office environment is not for me. Also, the Seattle rock climbing season is too short. So, in 2019 we decided to move back to Utah after three years away. At that time remote work was not a possibility with Amazon, so I quit. Funny thing is that now everyone there is remote, because of COVID.

Finding Bogleheads was one the best things that ever happened to me.

Mike Personick
Financial independence might just allow for more of this.
Financial independence might just allow for more of this.

Mike Personick on Building a Path Towards Financial Independence

CC: In the early days of having expendable income, you were drawn to the Bogleheads forums. What ideas resonated with you, leading to your own financial journey? How has your investing style simplified as a result of your learnings?

Mike: Finding Bogleheads was one the best things that ever happened to me. Software engineering is a lucrative career, and my company was fairly successful right from the beginning. So, early on in my career I was making more money than I was spending and wondering what to do with it.

I stumbled onto the Bogleheads forum by accident. From there I was able to learn pretty much everything you need to know about investing. Bogleheads is a term they (we) use to signify themselves (ourselves) as followers of John Bogle, the founder of Vanguard and inventor of the index fund.

Mike Personick Explains the Beautiful Simplicity of Passive Investing

The idea is simple. It is not possible to successfully beat the returns of the market over time. Also, there is almost no correlation between those who are successful in one time period and another time period. This means you cannot look at what happened in the past and expect it to happen in the future. Furthermore, you can mentally classify anyone who claims success picking winners and losers as a monkey throwing darts. So much research supports this that it is effectively a fundamental law of the universe, like gravity. Of course financial advisors will tell you otherwise, since their job is to take money from your pocket and put it in theirs.

(Related Post: Market Timing: Why It (Still) Doesn’t Work)

Luckily we have access to these things called index funds that let you own the whole market at extremely low cost and with extremely high tax efficiency. Of course with anything simple, people try to find ways to make it complicated. As such, there are index funds that track segments of the market by size, value, sector, etc.

Mike Personick’s Simplified Portfolio

When I first started investing and my portfolio was small, I thought I was more “sophisticated” by owning more types of index funds and thus “tilting” towards market segments that I felt had a higher expected return. Over time my portfolio has become larger and simpler, to the point now where I only invest in three funds – Vanguard’s Total Bond Market, Total Stock Market (which is a US stock fund), and Total International (which is an ex-US stock fund).

Simplicity is beautiful.

(Related Post: The CC Family Investing Strategy, Part 1 and Part 2)

Is a Financial Advisor Worth It?

CC: Can you tell me about your experiences with a financial advisor?

Mike: I had an advisor at Wachovia (now Wells Fargo) for a few months before I found the Bogleheads. I realized that his office, his car, his house, and his entire life were coming at my expense and the expense of his other clients. This wealth transfer was entirely one way.

I remember when I went to break up with him and tell him I was moving my money to index funds. I’ll never forget it, he said “well we have index funds too, ones that will outperform the market… well except for this year, we made a bad bet on the financial sector…”

(Related Post: Financial Advisor: Who Needs One?)

The Psychology of Investing Through a Financial Crisis

CC: You started investing in 2006, just on the big lead-up to the 2008 financial crisis. Can you elaborate on the experience of being an investor from 2008-2009?

Mike: The 2008 financial crisis was a formative experience for me. My portfolio was small, but it didn’t seem small to me at that time. I was scared. Everyone was scared.

This American Life was running episodes about the Great Depression, people were talking about tent cities, it was some real Grapes of Wrath shit. It wasn’t like what happened earlier this year, it was prolonged pain drawn out over almost two years. Many, many investors capitulated and sold everything. 

Related Post: The Shocking Headlines of the 2008 Financial Crisis (and Why They Are So Important Now)

S&P 500 and a handful of the major events of the 2008 financial crisis. (Chart via MacroTrends). This chart was originally posted here.

Turning the Corner from the 2008 Financial Crisis

By 2009, after we had turned the corner a little bit, the market was so beaten down that I was looking for ways to invest more. I had a Toyota Sienna minivan that I used for climbing and a fun little Audi A3 that I used for around town (I love cars). I decided to sell the A3 so I could buy more of the aforementioned Vanguard Total Stock Market fund. With those shares I could now buy an Audi R8. (I won’t. Probably.)

There were positives and negatives to investing through that period early in my investing career. Seeing and experiencing that kind of financial pain happen to you and others around you gives you a deep-rooted understanding of what it’s like when risk shows up. It’s good to be tested, especially when the stakes are small.

I feel sorry for people that started investing just after that crisis, only experiencing a rising market until this year. I’m sure many thought they were ready for it, but they found out the hard way that they weren’t.

On the downside, experiencing that crisis that early made me more conservative than I ought to have been. I never exceeded 60% equities in my portfolio after that, which is quite conservative for someone my age. My conservatism caused me to miss out on a lot of gains in the subsequent decade.

Mike Personick on Discussing Personal Finance

CC: Have you felt comfortable discussing your lifestyle/finances with other climbers or society in general?

Mike: I don’t think it’s a big deal. I don’t get into details, but I’m comfortable with people knowing the general situation. The more people talking about finances the better, as far as I’m concerned. None of us are going to have pensions like our parents did, so we are on our own to figure it out. We need to help each other. I’ve given away copies of “The Bogleheads Guide to Investing” to anyone who has expressed the slightest interest in personal finance and investing to me.

Unless you are the one-in-a-million person that can make money from your passion, look for something that you like (or at least don’t hate), that is easy for you, that pays well, and that is compatible with whatever your passion happens to be.

Mike Personick

Mike Personick on Chasing a Passion

CC: What are your thoughts on chasing a passion as it pertains to work?

Mike: Computer Science was pretty much the only thing I was good at in college, so I decided I’d do that. I wouldn’t say I was passionate about it, but I liked it and it was easy for me and it paid pretty well. And although I didn’t know it at the time, it also turned out to mesh extremely well with what I am passionate about: climbing.

This is basically what I advise anyone asking me what they should do with their career. Unless you are the one-in-a-million person that can make money from your passion, look for something that you like (or at least don’t hate), that is easy for you, that pays well, and that is compatible with whatever your passion happens to be.

If your work is not your passion it makes very little sense to do something that doesn’t pay well. And if you choose a career that doesn’t leave adequate room in your life for your passion then your soul will die, plain and simple.

Mike Personick

Each of these four dimensions is very important. Forty hours a week is a lot of time to spend doing something you don’t like. If you pick something that’s not easy for you, you’ll end up working a lot harder than your peers to get to the same place. If your work is not your passion, it makes very little sense to do something that doesn’t pay well. And if you choose a career that doesn’t leave adequate room in your life for your passion, then your soul will die, plain and simple.

(Related Post: Chasing Your Dream is Probably a Bad Idea)

Mike Personick and daughter Mika.

Mike Personick on Being “Retired” at Age 43

CC: At 43 years old, do you consider yourself retired? Why or why not?

Mike: I don’t even know what that word means in the context of someone who is in their 30s or 40s with so much time and human capital remaining. Certainly the older generation’s definition of retirement is less relevant to our generation, just as their definition of career is less relevant. The days of working for one company or the government for 30 or 40 years and then riding off into the sunset on a pension are over. Nowadays people cobble together a career from multiple jobs, self-employment, side hustles, consulting, etc. No one is really sure what that looks like yet when we’re all 65 or 70.

The important thing for me is financial independence; having enough savings and investments to take care of my kid’s future needs and support my family’s lifestyle without having to sacrifice my time on work that I don’t want to do. A financial buffer buys you freedom to live life on your own terms, whether you have six months’ expenses saved or enough money to never have to earn another dollar.

Financial Independence as a Spectrum and the Three-Legged Stool of Life

Financial independence is a spectrum, and the freedom it buys you is in degree. When I was younger I had a dream of “retiring early” once I reached this point. That said, as much as I love climbing, I don’t think just climbing forever is enough for me. 

I think of my life as a three-legged stool composed of family, climbing, and work. When I was working in the Amazon offices in Seattle every day my climbing suffered, and my life was out of balance.

Now that I am just climbing all the time my life feels out of balance again in a different way. I do think about what comes next. There is room for all three legs of the stool from our new base in Southern Utah, which is really a climbing paradise most of the year. In my ideal scenario, I’d work a few days a week and climb locally during the fall/winter/spring while my daughter is in school. We’d then take the summer off to travel and climb with my family.

Mike Personick and daughter Mika.
Mike and daughter Mika.

Life Without a Traditional Job

CC: Can you give us a sense of how life looks without a traditional job?

Mike: The last year I’ve been pretty much just climbing full-time and hanging out with my wife and kid. Gotta say it’s been pretty nice, despite the nightmare hellscape backdrop of the world we’re living in right now.

I tried to do a little consulting at first. It wasn’t fitting in well with our lifestyle, so I stopped. Back then my wife and I were alternating climbing days. We hadn’t figured out how to climb with our kid yet. So every day I was either climbing or being a dad. When COVID hit we weren’t comfortable climbing with other people at first. We realized pretty quick that if we didn’t figure out how to climb as a family we wouldn’t be climbing at all. That certainly lit a fire.

Gotta say, that’s the best thing that came out of this mess. We are a tight little unit now out at the crag, and I love having my kid there with me and being able to climb with my wife again. It’s also opened up a little space in our lives now for other things.

Can I Have a Family and Pursue Financial Independence?

CC: How does having children affect your ability to achieve or maintain financial independence?

Mike: I don’t think having children adds a huge financial burden. Well, so as long as we’re talking about a small number of them, like one or two. Even the cost of college pales in comparison to what you need to save for financial independence.

The real effects come in the form of trade-offs. Before I was a father it was easy to do two things well. It wasn’t hard to balance work and climbing, and I didn’t make significant trade-offs between the two. I made sure to never take on a job that would seriously impede my ability to climb, and I also avoided climbing trips or projects that would make it impossible for me to work. I’m not convinced I could have (physically) climbed much more than I did even if I weren’t working in those years. 

(Related Post: Mark Anderson: Fully Optimized)

Finding Family Balance with Financial Strength

Adding family to the mix is a whole different ball game. It is much much harder to do three things well. Family comes first, obviously, so the trade-off comes between career and climbing. In that sense the trade-off between financial independence and climbing becomes much more tangible when you have kids.

The goal posts of financial independence also change, not because of the added expense, but because you may be less comfortable choosing a certain lifestyle for your child than for yourself. For example living full-time in a van might be perfectly fine for me and my wife. Choosing that life for my kid on her behalf, however, seems less fine to me.

Mike Personick and the parenthood training weight.
Mike Personick and the parenthood training weight.

Climb Harder with a Kid?

I will say that having a kid has, for some reason that I cannot yet pinpoint, made me into a better climber. Maybe it’s because it’s just made me a better person in general. Perhaps that has carried over into my climbing. Maybe it’s because of the different sense of time and purpose you get from parenthood. Or maybe it’s just from carrying that little human bowling ball around everywhere all the time for the first two years.

Dada power.

If you are the best person in the room, then you’re probably in the wrong room.

Mike Personick

Mike Personick’s Closing Thoughts and Advice

Surround Yourself with Better, Smarter, and Stronger People

Mike: Always surround yourself with people that are better and smarter than you. Over time you’ll get naturally pulled up to their level. My wife Rayna is a better person than me, my business partners are much smarter than me, and I always try to climb with people stronger and more skilled than I am. If you are the best person in the room, then you’re probably in the wrong room.

Capitalize on Luck

Mike: I’m a firm believer in the power of serendipity. Serendipity has played a huge role in my life and in my path to financial independence. I believe strongly in the lucky break, and I strongly believe that everyone experiences a few of these in their life.

The problem I see, over and over, is that people squander lucky opportunities by not being ready for them, assessing the risks incorrectly and opting for the status quo. Opportunity is always accompanied by risk. I’ve been lucky in my career and my life. However, not all of the choices I made were obvious at the time. Many involved significant risk, and had I taken a more conservative approach to my life, played it safe, all the luck in the world wouldn’t have mattered. 

Break Free of Routine

Mike: Routine is the enemy of serendipity. Seek out unfamiliar places and unfamiliar people. Make a habit of checking in on people that you hardly know or haven’t talked to in a while. You never know where this will lead. Usually nowhere. But sometimes you start a business. Or meet your wife.

Summary

I want to sincerely thank Mike for agreeing to do this interview. His story is a relatable tale of pursuing stability, mastery, and still having plenty of fun along the way. We can have our cake and eat it too.

Although he’s admittedly not very active, check on Mike on Instagram.


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2 Replies to “Mike Personick: Dirtbag Entrepreneur”

  1. Great interview with Mike. Some great insight on balancing family-climbing-work and how being a parent changes your perspective.

    “…look for something that you like (or at least don’t hate), that is easy for you, that pays well, and that is compatible with whatever your passion happens to be…” This is where I am now.

    Thank you for doing these interviews.

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