Playing the long game, notes on hiring, and our Series A

June 30, 2019

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“Today never feels like it will be history, but it will. And more likely than not, you will look back and realize that you should have known.” — @scottbelsky

Well, I find myself just past the end of Q2 2019 and well overdue for a small update. Before I dive in, I would like to extend an incredible amount of gratitude to all of the people who are in my life—both those who have been by my side and those who I’ve met recently. At the end of the day, other people are what make life worth living and I hope I never take all of the truly wonderful people in my life for granted.


1H 2019 saw a lot of exciting things. One of the things that I learned about “exciting things” is that it’s often the case that when you’re in the moment of it, it actually feels only somewhat celebratory at best. It’s not until you look back or speak about it that it begins to accumulate worth—though as the aforementioned Scott Belsky quote illustrates, I suppose I should know by now.

In April, Possible Finance launched in the state of Ohio. We’re now licensed in six states, and are a team of 17!

In May, we announced Possible Finance’s $10.5M Series A fundraising round. The effects of this I discuss further below, but it really was and is a big deal. Thanks to all of our investors who believe in our team and mission, and to everyone who has supported us thus far! (We did get to have a pretty fun office party to celebrate.)

In June, we launched the Rosebud Scholarship Fund, a nonprofit organization dedicated to helping Lakota Native American youth get to and graduate from college. One of my stealth-mode projects from last quarter is now in the light of day, and my friend Troy and I have been working hard to make it a reality. I’ve always been invested in education, both coming from a family of educators and having served on the Washington State Board of Education, and while I’m not a place in my life where I want to pick up and devote myself to teaching, I’m trying to do my best to use my time and current skills to widen the stage for others to help, too.

Playing the Long Game™

I joined Possible Finance as the first employee a bit over a year ago now. The first year at a startup that wasn’t failing was certainly enthralling—seeming to have big news every week, never slowing down, and never not working. I actually function quite well like that, especially with a project-based structure. However, a number of habits that lend well to scaling a startup through its infancy don’t scale a company or team, for that matter, beyond that. I admire greatly the work ethic of our co-founders, and find that it’s easy to work around the clock when there’s so much to be done. Truthfully, though, there is always so much to be done and there always will be so much to be done that the task for me is no longer continuing to work, but to craft a lifestyle that allows me to be effectively working when I do work and staying healthy with a balance of time with my friends and family. Having raised a Series A, we’re asking ourselves a lot of new questions at work, and it’s become more important to me than ever before to settle in for the Long Game™.

While at an organizational level at work, the Long Game™ is about things like getting health insurance, the Long Game™ for me is about blending work and other aspects of life in a sustainable combination. I find myself restructuring my approach and mindset about a lot of things, and one of those things is how I think about the interplay of strictly work-related things and non-work-related things. Jeff Bezos’ concept of work-life harmony has resonated lately, because while I spend long hours in the office, I don’t find that it feels like I ever have to be there. (So basically what I’m saying is that I may disappear for months on end. Just kidding, that’s unhealthy.) Realistically, I’m taking some time to do new explorations about what things matter to me, how I translate those priorities into my life, and how to communicate more effectively with other people. That’s the thing about the Long Game™—other people matter!—and you have to be excellent at expressing yourself and your thoughts in order to keep things smooth. I always say that I’m growing with the company, and by that, all I mean is that I am also in a period of accelerated growth, firsts, and hard work.

When the only way out is through

There were a few times in the last year that were harder than others, both personally and professionally. That’s to be expected. I have tried so hard in the last year to release the guilt of not tackling something perfectly the first time, and to remember that I should provide myself the same level of patience as I do others who are also learning. Essentially all of us at work are in roles that we’ve never had before, and it’s up to all of us to make them work for us. Though an overused metaphor, when you put the reps in, you get better. Once you do A for a second time, you can move on to fail at B, and when you’ve done B another couple of times, you can start doing C, D, and E, and so forth. Perseverance and resilience are some of humankind’s greatest qualities, and they become applicable in so many ways.

Notes on hiring

I’m learning how to hire people for different roles, and it’s hard, though to be honest, it’s hard in ways I didn’t expect and for reasons I didn’t know would exist. Knowing if someone has the correct technical skills is actually quite irrelevant sometimes, and it’s incredible how much you can learn about how someone works with others in a 45-minute interview. (So why do people spend so much time making little progress bar thingies on their resumes? Unclear.) Understanding your own team’s dynamics and needs is critical to being able to articulate what you’re actually hiring for. Unfortunately, I wasn’t that surprised about a lot of what I heard from many candidates about their experiences with recruiting at other companies. At a certain scale, hiring becomes another process to be optimized, but it seems hard for people to remember the people behind the names. It’s a cycle that easily begets apathy on both sides—and what a disheartening way to be hiring people or finding a job. Treat people like people and even ending a hiring process with someone will feel easier.

Being, going, and knowing home

I moved this month, and for the first time, I’ll be living somewhere for longer than one year. It seems insignificant when in fact, knowing that I can invest time and effort into making a place really feel like home has had a tremendous impact on how I’ve settled in. I always speak about making sure that my own feeling of “home” is internalized and therefore independent from any sort of outside influence, but in honesty, that’s out of fear. Having gone through moving every quarter when I was in college to moving all the way to Scotland and back did not make me excited for the emotional move, so to speak, every time I had a physical move. I have done a good job of internalizing home and creating a network of add-ins in people that I love very much, but it’s relatively new to have a physical home as an extension of my understanding of it. I’ve been doing things to make it mine and I feel very newly relaxed. (It’s also serendipitous that we’re moving offices and we’re moving even closer to my new apartment.)

Supporting Materials

The One Line A Day journal. I’ve had mine for almost two years now and it’s slowly made its way into my list of Irreplaceable Items. Seeing my entries from even a year ago often force me to remember how much I’ve learned and truly how much I’ve changed in positive ways.

Today, Explained podcast episode from May 31, “Sex and branding”. I listened to this a few weeks back and wow, if you have ever been curious about cults and deeply evil human beings, listen to it.

Snacks Daily podcast. Recently acquired by Robinhood, I listen to Snacks Daily semi-daily for interesting takes on companies IPOing, various mergers and acquisitions, and some product strategy stuff. It’s certainly a fun and light way to consume the information that could easily be boring otherwise.

In keeping up with the 2020 election, I watched the first democratic debates…and then promptly turned to The Daily Show’s take — Night I, Night II. (Bonus: a Twitter thread of some of Marianne Williamson’s best tweets surfaced after the debates as well. It’s great.)

KARAFF Carafe from IKEA. This amazingly cheap (quite literally $2.00) carafe from IKEA is one of my favorite new household items. I make and keep iced tea in it in my fridge and it’s just so satisfying to hold and pour from.

Can’t Unsee. A fun online game in which you must choose the “most correct” user interface design. UI is so nuanced, and while this is solely visual, it’s a fun exercise.

Looking Ahead

Summer is in full swing in Seattle, which means that people will actually be outside and you may even get a smile from a stranger. Possible Finance will be moving offices at the end of next month, and as many have told me, I will most certainly miss our current office even though it’s getting extremely cozy. We now have three phone booths in addition to our one conference room: the supply closet, the landing at the top of the stairs, and the landing at the middle of the staircase. Our new office has multiple phone rooms and meeting rooms. It will definitely be an upgrade, though even now I remember our first office at the SLU WeWork, when we got up to five people in a four-person office, with a distinct bittersweetness.

I’m deciding where I should travel to next. I haven’t even left the country in the last year; my flight log is all domestic and actually only SEA and SFO. I’ve been eyeing Japan (I took Japanese in high school but never visited) and of course, Scotland (I miss all of my friends there so much!). We’ll have to see—any and all suggestions are welcome!

Maybe this time I’ll get an actual article about something other than a quarterly update. But at the same time, sometimes I’m really just preoccupied doing all of the things that make it into the quarterly update. Prioritization wins out in the end.

Version notes:I recently made some visual changes to my website so it is more readable, including changing colors and typefaces.