Post-Startup Life: Reflecting on My First 18 Months Living in Denver

In December 2017 my husband, myself, and the remaining cadre of Mattermarkers who remained moved to Denver as renters and “short-timers”. Given how we started out, I didn’t put odds on staying long. We started out fresh from California in the middle of winter, as part of an acquisition capping off a long M&A process that had left me pretty burned out. We hadn’t planned to move, but it was what we needed to do to close the deal so we did it. Alighting on a new city in the midst of the holiday season, we didn’t have our support network built up over the past 10 years (basically my entire adult life) in the Bay Area, let alone the right clothes to weather the initial shock of change.

After spending years building something that’s no longer yours, especially if as in my case you have nothing (at least economically) to show for it, can raise questions about whether it was worth building at all. I spent 5.5 years, from early 2012 to mid 2018, on the Referly/Mattermark/FullContact rollercoaster with an average annual salary of $120K and net negative personal savings rate. In the sale of Mattermark, the purchase price did not clear the amount invested by preferred shareholders and common stock (including all the founders and employees) was wiped out. There was no success fee for completing the deal, just my honor and self esteem + a job offer at the acquirer with a relocation bonus.

I’m not complaining (and doing the deal was ultimately my choice and the best option available to the company), just laying it out in a bit more detail because sometimes I think people try to leave things vague to create an aura of mystery when founders have these types of exits. Despite all the work I’d done to separate my identity from my role as startup CEO, I felt quite shitty about this outcome… and it took a lot longer to work through those feelings than I could have predicted.

Where Am I?

Initially, we lived out of an Airbnb in Washington Park with our 4 month old puppy (Emo) while scouting for a pet-friendly rental in the neighborhood, but ultimately ended up finding a brand new duplex in Cherry Creek North renting for less than our portion of our former 3 bedroom apartment with roommates in San Francisco.

Moving into this tony old neighborhood of Denver was funny, mostly because we constantly felt like the youngest people around. After starting to feel “old” among our eternally 20-something tech startup peers in San Francisco, the average age of 65 was refreshing. Older Denverites of relatively good health are super active with their dogs, their gardens, and myriad outdoor sports and we met a lot of friendly people very quickly. Even at -1F (New Years Day) we relished the walkability of our 16-block shopping district and the mostly sunny climate with 2-4 inches of snow every week or two.

I started learning about the neighborhood’s history, and discovered it was founded as the township of Harman in the 1880s by Edwin P. Harman and his wife Lou, and annexed to Denver in 1896. As neighborhood folkore goes, Edwin was a decorated Confederate veteran and former lawyer and judge who became disillusioned with post-bellum life in Mississippi and decided to head West. I love that the original town hall still stands, always has the best flowers in summer, and has been tastefully renovated to host fancy community events. The city of Denver was founded in 1858, and Colorado did not become our 38th state until 1876, so this was all happening in a very short window of frontier history.

Beyond the local history, I also started to familiarize myself with the surrounding natural environment (Red Rocks, Front Range, Loveland Pass, Aspen, Durango, Mesa Verde and so much more… I took a week-long solo road trip through the Southwest), plants, animals (prairie dogs!), birds, bugs (cicadas!), weather (tornado warnings!). At first, I was still too burned out to do much socially, so I held off on engaging with the startup community or making an effort to find new friends beyond whatever happened naturally through day-to-day life. Through my responses to the warmth and outreach of others, I felt myself become nicer, less hard, less guarded. I started hosting small get togethers at our house. I was still pretty overwhelmed with my inner monologue, and didn’t really know how to explain myself if asked, “so who are you? what do you do?” but angel investment opportunities started to come my way, impressive local female founders.

Little did I know, time passing was working its subtle magic on me. Simply by existing, I was working through a lot of things during my experiment with retirement, which I branded as “professional sabbatical” since I didn’t know if it was going to be permanent. I felt myself becoming more stable and comfortable with my identity not being tied to my work.

How Am I Going to Pay for This?

I wrapped up the Mattermark transition in May 2018 and decided to use some of my savings to take the rest of the year off. To satisfy my need for an incremental spreadsheet to constantly iterate on, and because I finally had the time, I took over the “CFO of household” role from my husband for the first time in our 11 year marriage.

After an initial audit, which included calculating our net worth and IRR for the first time since 2012, I began thinking through how to diversify away from concentrated positions in startups and public stocks, and replenishing our retirement savings (Kevin had cashed out his 401k for a previous failed startup, so we were pretty behind where we should have been). I re-read “Your Money or Your Life” (thanks Dad for having that on the shelf when I was a teenager!) and began to engage with the FIRE movement (Financial Independence Retire Early) community to find more people like me.

When I say “people like me” I mean people for whom working or not is a choice, because they’ve accumulated the wealth required to deliver economic freedom. Living the lifestyle I want (which is not particularly frugal) entirely off the compounding returns of my investments, even at a fairly conservative growth rate on the principal, is an option for me now.

Can These Numbers Really Be Right?

Being young and in a position to never work again (at the 4% withdrawal rate, with some tweaks to my spending habits) sounds great and is literally the millennial dream if you spend much time on Instagram. I’m incredibly grateful that the stock I received for my work at Twilio ended up generating my wealth, but it’s also terrifying in the sense that it is all new and feels like it could disappear tomorrow.

After making my detailed spreadsheet it was undeniable: at a relatively conservative compounding growth rate, I could stop working and cover my expenses with my investment income and I would have more money than I’d ever need to spend in my life. It was very disorienting to have my net worth climb from something I hadn’t worked on since 2012, while my current efforts were amounting to nothing in economic terms.

I wondered if the math could really be right, and checked it a ton of times. I found it difficult to figure out who to discuss these questions with, since its taboo to talk about money in general, and retirement in your 30s specifically can trigger all sorts of reactions. Most of us have been fed the idea that retirement means we work until 65 and then take it easy playing golf, going on vacations, and buying a beach house, and never questioned that. As I reached out for advice I was surprised to find many people who are high earners but have very little savings. For them, talking to me about my plans brought up a lot of uncomfortable comparisons about life choices. I’ve included a list of resources at the bottom of this post for anyone who is curious to learn more about thinking through questions like this.

What Do I Do With All This Time?

Being on sabbatical gave me a taste of what retirement would look like for me right now: I had few friends or hobbies, no kids, and no long term goals or vision for my life. I had put pretty much all of this off while working on my startup, and then had moved away from my established community, habits and routines. I struggled to explain myself outside of my work, and even the creative things I had become good at didn’t ring true and I struggled to say, “I’m a writer” or “I’m an analyst” or “I’m an investor” or even “I’m an inventor” even though any of these answers is right. All this meant meaning-making was extremely difficult each day, and I started to wonder, “what do I do with all this time? is this all there is in life?”

For anyone who has ever suffered a bout of depression, these thoughts are warning signs. For me, I immediately began to build out lists of things I wanted to do, and fill my days with activities to stave off these thoughts. I spent a lot of time and money getting my hair done, working out, cooking, traveling extensively, and reading even more extensively. Each day I would write down everything I had done that day, and recite it to my husband. Thanks to a lot of time spent doing mindfulness training over the past few years, within a few months saw all this manic movement without purpose for what it was: a way to paper over my anxiety about my direction in life.

This is loosely written in chronological order, but for any reader who has made it this far I want to reassure you *I regressed many times* and it is still happening. It is not a linear path from not feeling okay about your life to feeling okay again, and I still have mornings where I wake up in a funk that takes me hours to shake off.

Why So Much Focus on Money?

Economic freedom is a powerful thing, and I growing up in the household of an entrepreneur I lived by the ebb and flow of the business and its income. When I started working as a stablehand at 13, for my Dad as an analyst at 15, at McDonald’s at 16, as a receptionist at the tennis club, as a tennis instructor for the Parks & Rec Department, as a barista, as a freelance website consultant… each move was a step toward freedom from the strings that came attached to my parent’s money, a step away from the financial precariousness that shaded my childhood.

Money isn’t something I hate, but I’m also wary of loving it. I don’t think it is a good idea to love tools you didn’t make yourself, or at least to love anything that is as fungible as money. What I love is freedom to live the way I want to live, do the things I want to do and also NOT do other things, and to be able to adapt to the world quickly and face the reality and consequences of my own choices. I’ve done several significant of “off script” things in my life including skipping the 4-year college checkbox, getting married really young, starting my own companies, and deciding to be childfree. There are many more that are too personal to share here.

Because of my tendency to do things that are at odds with what society tells us to do, I have assigned an additional level of responsibility to myself economically to always be able to protect myself from the potential fallout of being “weird” or different. Regardless of the fact that I enjoy a long marriage, I feel it is extremely important that I don’t need to rely on anyone else for money (or the protection it provides) and that I not subject my partner to a situation where he is carrying out the role of “Good Provider”.

So to simplify all this, I am focused on having money because it confers economic power, and economic power can be used to purchase freedom. Having the Freedom to live my life as I choose is my highest value.

But What About… You Know, Denver?

Denver’s great, but I can hardly claim to know it yet! It has been an excellent cocoon for me as I figure out what I’m doing with my life. The next chapter likely involves getting much more involved in the local community, doing a ton more outdoor stuff, finally learning to ski (lifelong snowboarder but I broke my ribs when I was early on at Referly without healthcare… long story) and so much more.

It took me at least 3 years to start feeling really at home in San Francisco, so I am expecting the pace for this will be about the same here. If you want to see the cool places I’m exploring, eating, hanging out etc. check out my Instagram – it’s public now so everyone can follow along as our puppies grow up!

Consciously Choosing Goals for Life in 2019

Given how much I love my freedom to live as I choose, you’ll probably not be surprised to hear that I am very into thinking through just what I should do with all this freedom I’ve earned. As 2018 came to a close I did my yearly exercise of writing down goals for the coming year. I chose 3 themes:

  • Establish Creative Work Routine
    • I would like to be writing and painting (~4 hours per day), and I also want to explore startup ideas.
    • Grow
    • Launch paid associate-as-a-service newsletter
    • Start coding on personal CRM project
    • Continue XFactor partner role + angel investing
  • Improve Physical Fitness & Appearance
    • I would like to have a slender, healthy, attractive body.
    • I would like to be comfortable on the floor with the dog, falling asleep, and doing athletic activities.
  • Prioritize Making Memories
    • I would like to have a year filled with memorable experiences that honor my values, including outdoor exploration, live music, eating and drinking out and other fun stuff.

What you might notice is that nowhere in here did I say “I want to get a job”, “I want to get another dog” or “I want to buy a house”. Arguably, the three biggest decisions I’ve made in 2019 weren’t on my list. Thematically, I’d say the dog aligns with physical fitness and the job aligns with creative routine. But the house? The house is awesome, both emotionally and as an investment, and is totally the right choice. But it also reveals something about a hidden theme, perhaps the “why” behind these other themes.

The bigger theme is that I want to build a life. I am actually motivated to build my life up again, even though one lesson I’ve learned is the impermanence of it all. I found it a painful lesson to discover that sometimes good things (like startups you love or lifestyles in cities you love) do come to an end. I’ve realized that it doesn’t make the world a dark, bad, or hostile place and it doesn’t mean I’ve lost my freedom. Perhaps this is 1999 or 2006 in terms of market cycle, but this time I have so many more resources, and so much evidence that I can weather whatever storm comes.

Lead by Mary Oliver (listen to this poem read aloud)

Here is a story 
to break your heart. 
Are you willing? 
This winter 
the loons came to our harbor 
and died, one by one, 
of nothing we could see. 
A friend told me 
of one on the shore 
that lifted its head and opened 
the elegant beak and cried out 
in the long, sweet savoring of its life  
which, if you have heard it, 
you know is a sacred thing, 
and for which, if you have not heard it,  
you had better hurry to where 
they still sing. 
And, believe me, tell no one 
just where that is. 
The next morning 
this loon, speckled 
and iridescent and with a plan 
to fly home 
to some hidden lake, 
was dead on the shore. 
I tell you this 
to break your heart, 
by which I mean only 
that it break open and never close again  
to the rest of the world

Best Resources to learn more about FIRE (Financial Independence Retire Early):

There are a TON of resources for FIRE now that the movement is spreading, but these are the ones I found the most valuable.


Playing with FIRE — Retirement Calendar


“Reboot: Leadership and the Art of Growing Up” by Jerry Colonna

“Your Money or Your Life” by Vicki Robin and Joe Dominguez (this is the original source of the movement, written in 1992!)

“Early Retirement Extreme: A Philosophical and Practical Guide to Financial Independence” by Jacob Lund Fisker

“The Millionaire Next Door: The Surprising Secrets of America’s Wealthy” by Thomas J. Stanley and William D. Danko

Blogs: Mr. Money Mustache (+ he has a coworking space here in Colorado!)



Naval Ravikant

Reddit: r/financialindependence and r/FATfire

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