Ex-Lyft PM and Bain consultant building a $250K ARR bootstrapped company, fully remote

1. Hey, can you please introduce yourself?

Ahoy! I’m Collin Waldoch, co-founder and CEO of Water Cooler Trivia. I’ve spent the past 14+ months working remotely from across the USA while building a company from a side project.

Prior to working full time on Water Cooler Trivia, I was a product manager at Lyft’s NYC office and a consultant at Bain’s Boston office. In early March 2020 (just before Covid hit), I left my job at Lyft and planned to travel the world while growing Water Cooler Trivia.

My fiancee and I flew to Argentina in early March and three days later we were back in the US after the virus became a global pandemic and borders shut across the country. As a result, the two of us have worked from across the US in the past year – splitting time between living with family and living in extended Airbnbs. We’ve spent at least 1 month in Louisiana, Illinois, Wisconsin, Virginia, New Mexico, and California at this point.

Working outdoors in Santa Fe, New Mexico in July 2020.
Working outdoors in Santa Fe, New Mexico in July 2020.

2. What motivated you to choose remote working?

It hasn’t quite played out this way, but the primary factor was seeing more of the world. In particular, I wanted to not just vacation in different countries and cultures, but actually live there. So the plan was 12 months of traveling with a 3-month stint in 4 different cities in 4 different countries.

In addition to the travel aspect, the beauty and attractiveness of remote work to me was an increased sense of ownership over my own schedule. Whether that means a mid-day run, a time-shifted day to be more of an early bird, or afternoon walks with my partner, the flexibility inherent with working from one’s own physical space attracted me.

A huge benefit - being able to work from the pier on a lake for an evening call.
A huge benefit – being able to work from the pier on a lake for an evening call.

3. What were your initial months like? Did it live up to your expectations?

I didn’t expect to start my remote work journey during a pandemic! Certainly this made things worse. The start of my full-time remote-work also coincided with a career change away from a larger team and towards working full-time on my own business. So the experience of those two changes are entangled for me, in positive ways.

For remote work, I quickly settled into an “alarm-clock-free” work schedule which led to huge variation in my days. Some days I would work from 7am – 7pm and some days from 10am – 4pm. Personally, I love working in unstructured schedules like this so going remote was quickly a boon for my mental well-being

Physically, within two weeks, I’d purchased a new monitor, keyboard, mouse, and headphones. I’d relocated my home office to have more sunlight.

4. How did you find remote working roles?

As noted above, I became a full-time remote worker simultaneously with going full-time into my bootstrapped side project. Lot more details on that transition and jumping-off point can be found at this podcast I recorded with the team at Indie Hackers.

5. What have been the best, good and worst aspects of remote working for you?

I don’t think I have anything particularly novel to add here, but I think it’s meaningful that my answers are probably similar to most others.

The ability to travel. Living across the country this year has been a treat, and was not at all possible without the availability and rapid acceptance of remote work. In particular, I went from city-to-city in one-way rental cars, so while living in each area I was car-less, forcing me to live in a small radius like a local, walking or biking to the grocery store and laundromat. I lived in Santa Fe and New Orleans – two cities that have fascinated me and now areas of the country I think of fondly and would consider living in for longer periods of time.

Not on the highway here, but still having some fun while working with back to back screens at a tiny table in a studio apartment.
Not on the highway here, but still having some fun while working with back to back screens at a tiny table in a studio apartment.

Schedule flexibility. Fairly straightforward, but the ability to eat meals, make coffee, take breaks on your own time is lovely.

The loneliness. Video calls just aren’t the same as personal interaction. Relationships feel more transactional, which leads to more concerted effort in establishing empathy and understanding with coworkers, vendors, or sales prospects.

Dissolving boundaries between work and non-work. The friction to re-open the laptop and send just one more email, which rapidly turns into one more hour of emails is extremely low when working remote vs. being office-based. It requires discipline and internal security in your role to fight these demons.

6. What tools do you swear by while working remotely?

Trite, I realize, but Slack and Spotify. I’m also a big fan of Google Meet because of the ease with which it is included in calendar invites and the fact that it runs in-browser vs. a separate application. I think that these three tools are enough to get by in most remote work circumstances, along with any other software needed.

Also, I’m biased, but having a fun weekly activity that the whole team looks forward to like Water Cooler Trivia has been great for sparking conversations about things other than the weather or the pandemic.

7. Your most exciting/ hilarious experience since you started working remotely.

I think my favorite experience has been the weird places where I’ve taken sales demos with potential clients for Water Cooler Trivia. Thanks to a personal hotspot on my phone, I can work from the car when my partner is driving. And thanks to virtual backgrounds on Google Meet and Zoom, I can fake my location fairly convincingly. Toss in noise-canceling headphones, and now I can fully take video calls while moving 85 miles per hour on the highway.

The funniest specific example was in the middle of Nevada in September 2020. I had a demo call in 10 minutes but the cell service was spotty, so my fiancee and I pulled over at a rest area that was basically a port-a-potty and a few overflowing, fruity fly-swaddled dumpsters. But there was cell service. So I took back-to-back demo calls next to these dumpsters with a fake background displaying an urban garden. 30 minutes later, back on the road to our next destination.

8. What is your golden advice to a new remote worker?

Be proactive with your time. If you’re going to start work later one day but stay online later, just tell your team. Folks will default to assuming good intentions and trust, and it’s up to you to maintain and increase that level of trust. Proactively communicating your schedule for a given week or day is the best way to increase that trust which pays dividends down the line.

Taking press kit photos for Water Cooler Trivia while working remotely from Wisconsin.
Taking press kit photos for Water Cooler Trivia while working remotely from Wisconsin.

9. How do you see your career shaping up and your goals?

I fully expect to continue working remote, but I’m also excited for more in-person collaboration with colleagues. At this point in time, that will most likely be growing Water Cooler Trivia with a remote team or down the road could lead to other jobs in the tech industry (most likely as a product manager) where I’ll be remote-first.

10. How do you expect remote working to evolve in the future?

It’s inevitable that we’re entering a long-standing wave of “hybrid work” but that term itself is incredibly vague and wide-ranging. Hybrid could mean a company with half of the employees in HQ and half globally distributed, it could mean a team where every employee is in the office Tue/Thu and remote Mon/Wed/Fri or it could mean everything and anything in between.

The team size, industry, and cultural connotations will all drive the share of “hybrid work” happening in a given geography, but there’s no doubt that 2019 was peak “office workers in offices” with respect to physical co-location for the white collar economy.

11. Where can we follow you on?

On Twitter, I’m @cowllin and I also manage the account for my company @WaterCoolerTriv. My Linkedin is linkedin.com/in/trivia where I often share updates about my business and working remote as well!

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