Lessons Learned from Four Months of Working Solo

tl;dr — After four months on the solopreneur track, I’m returning to work at Shopify full-time. I learned a ton about building Barkpass, but it’s not a full-time venture right now.

The following is a slightly edited version of what I wrote to help myself digest what I’ve learned, why I decided to do what I did, and what I’m going to do differently moving forward.

Why I Left Shopify

I’ve previously written about my first year at Shopify. At the end of 2023, I decided to leave Shopify and… not get another job. 

I had been at Shopify for three years. My trajectory at the company had been pretty wild — from joining during the early days of COVID when the company had just gone remote and the stock was skyrocketing, to building on a brand new tech stack and collaborating with all sorts of amazing people in the open source ecosystem… 

…to me eventually transitioning out of that role into a new role out of my wheelhouse.

I won’t dwell a ton on what I was doing when I left — suffice it to say that I was working in an area where I lacked both experience and passion: low-level systems stuff, database materialization, database replication, Ruby application design and refactoring.

That’s not to say I didn’t really learn a TON and gain respect for the work those teams are doing! It just wasn’t for me.

The year 2023 was difficult in particular. I felt stuck. The work I was doing at Shopify didn’t happen to intersect with my skillset nor my interests, which is not a great place to be, friends!

I had two choices:

1. Stay. Try to navigate my way across the jungle gym of Shopify to find something new to do. This would involve a lot of boots-on-the-ground, talking to new people, and political red tape to get me to a new team.
2. Leave. Try to do the solo thing I’ve always wanted to do.

Given that it had been three years, and I had a little savings built up, I decided to leave and try to go solo for a bit.

What I did the past four months

My intentions were to build something for myself, fulfilling a dream of being an entrepreneur and running my own company full-time. My wife, Bri, would keep her full-time job and provide for our family, including two young boys with daycare costs.

The initial plan, which made sense, was to start with Barkpass and see how far we could get. It had been a side project for five years. My attention to Barkpass dwindled year over year, more severely as we had our second child. 

Barkpass has two primary customers: government and business.

Government customers are typically interested in pet licensing programs for their towns or counties. Sometimes they have a dog park they’d like to manage.

Business customers tend to be one of the following:

• Private dog park + beer, coffee, food combo
• Private dog park + dog daycare and grooming

My plan was to try to increase customer growth in both sectors, which meant focusing on selling and building missing features to help us close deals.

Here’s how it went!

Selling Barkpass to Government customers

Thesis: if I dedicate proper attention to expanding the feature set of Barkpass and go sell it, customer growth will skyrocket and it will eventually replace my full-time salary.

I started by cold-emailing top cities in Iowa by population, and I quickly learned that selling to government was not what I thought.

I’m going to write an entire novel about what I learned about selling to government, but one teaser is that cold calling and emailing super sucks and doesn’t work at all.

We booked a booth at the Iowa Parks and Recreation state conference in March with the goal of spreading awareness and getting some new leads. We even sponsored the conference, so our logo got published in places! Bri did really great with getting swag and booth signage made.

The reality: We didn’t land any new government customers during this four-month period. We didn’t really even have any new leads from government customers. Only a couple of the 150 cities represented at the IPRA conference could even use our product.

Some of the prospects I talked to were just too small — one customer had just blown their entire budget on buying a light pole for the dog park but encouraged me to check back in 2028 🙃

Selling to government customers involves a strong word of mouth approach and takes a lot longer than I thought. You can try to increase velocity by using partnerships of existing GovTech vendors who have a fleet of sales teams across the nation, or by hiring former government employees who can use their authority and existing network to advocate for your product. 

The biggest takeaway here was that our product is too niche for government customers.

The overlap of cities that have:

• A pet licensing program, or…
• A dog park…
• … that they require permits to access
• … and have a budget for software
• … and don’t already have permitting or recreation software that solves the problem well enough

Is just too dang small. In business terms, our SAM — government customers we can service with our existing product — is much smaller than our TAM — all local governments in the United States — which is already finite.

I’m still confident that Barkpass can grow to be used by government customers across the country, and even internationally, but it will be a slow burn. It’s more fitting of a “side project income” for us from both a sales and maintenance perspective than a full-time focus.

Selling Barkpass to private businesses

The thesis: A dedicated sales and product effort to landing private business customers for Barkpass would lead to a massive increase in sales. Private dog parks are on the rise, and the market continues to grow.

Contrasted to government sales, we did have quite a few inbound private dog park leads during this four-month period. This was great, because my schedule was wide open to give them a 30-minute demo. I really honed my pitch deck and demo walkthrough, and I was feeling pretty confident.

We landed a couple new private customers at the beginning of the year, but most of these had been initiated in 2023.

The reality: We lost most of the private business leads since Barkpass is not full-service enough for dog park bars which typically have a daycare or grooming component attached.

These businesses do not want to pay money for both a dog park management software and a daycare or grooming software, and the latter are much more full-featured than Barkpass.

Our competitors in this space have raised money and have entire product and sales teams. They also have a strong background in the pet services space, so they know exactly what problems to solve and what to build.

A naive part of me says, “Heck yes, I can build a simple scheduling component into Barkpass and capture this whole market!” But the reality is that it’s really hard to take down an incumbent. Especially when I’m bootstrapped and working as a solo developer.

I attempted to reach out to local doggy daycares and groomers, and I heard crickets from people.

Seriously, it was like pulling teeth trying to get people to talk to me. I’m a nice guy, I swear!

This did not bode well for trying to build a product if I couldn’t even get the time of day from local companies.

Barkpass can’t compete in the pet services market, for the time being at least. Barkpass can continue to operate successfully in the “dog park bar” space and has a small handful of customers who are just launching now and who will provide valuable feedback for that offering.

Rapid product development

The thesis: With all of my free time, I’ll be able to crank through ALL THE THINGS I had ever dreamed of. Unencumbered by big company politics slowing me down, I could ship at a ridiculous velocity.

The reality: I shipped a lot! But as I was talking to my buddy Corey who also left his full-time job at the end of last year to focus full-time on his product, it was a lot less than we thought.

I’m not sure if it was a simple mismatch of expectations, but a lot of the work I did involved long-term architectural thinking rather than cranking out features. The type of stuff that involved designing systems and thinking about all the side effects and long term impacts. Things that you ship and then immediately have to revert because of something you hadn’t considered.

I did get a lot of impactful features built and shipped, though: access control, hardware and gate code integrations, mobile and administrator-driven check-ins, QR codes and USB scanner support, all help our private and public dog park customers. 

I also shipped a redesign of the admin and an improved marketing site, setting us up for future expansion. Again, long-term consideration on a lot of stuff!

Side note: Why not take funding?

One funny thing about running Barkpass after five years is that we get cold inbound emails from investors at private equity firms all the time. They all have interest in consolidating GovTech businesses and exiting them.

The catch? “We typically write checks for companies fitting the $2-3MM ARR profile.” Like, holy crap, we are so far away from that at Barkpass right now. I mean, if we were making $3MM ARR at our current capacity, do you even think I’d even be looking for more money?

So: am I the problem? What are we doing wrong that we’re not raking in all this money? And why do PE firms keep hitting us up even though we’re small potatoes? Do we give the illusion that we are much larger potatoes? I don’t know.

I kind of thought about applying for the Calm Fund or other government grants, but I just didn’t dedicate the time to it.

At the end of the day, it’s kind of a “pick your battles” thing — do I want to go all in on pet services software, or can I select a different market that requires less sales weight and leans more into my strengths, e.g. developer tooling?

Other ideas

I also had considered other ideas during my solo time:

Superflare

Expand on what I’d launched a year ago and then subsequently paused on. Maybe build something else in that space that’s more agnostic and can be deployed for Vercel, etc.

I didn’t want to continue as-is with an open source project with $0 in funding and something I didn’t use myself.

I never got around to this, sadly. But it’s not dead!

New Startup (Code Name: Gosh)

A startup aimed at solving the loneliness epidemic.

Under the hood, it’s really a calendar scheduling app that uses LLMs to remind you to hang out with the people that you love and suggest ideas for date nights:

Gosh! It’s been three months since you last hung out with your buddy, Chad. Want so schedule a coffee on Wednesday at 10am?

I built a very small prototype but kind of stalled out on the idea because of how difficult it would be to monetize.

My guess is that consumers aren’t going to pay for it, even if you go for an angle of “you pay money to exercise your muscles at the gym; pay a small amount to exercise your social muscles, too.”

You could try to sell ads a la FB at scale, but that doesn’t come until scale and sounds like a nightmare, honestly. I’ve already been down the adtech road before.

Also, much of the code would be annoying business logic around scheduling and recurring events that have been solved by others. I still like the idea, and I would use it myself. But I didn’t spend much time on it.

Consulting

I talked to one company that was looking for a software dev consultant, but I didn’t ever hear back from them.

I could have put more effort into finding local consulting gigs, but… I kind of didn’t want to, because it would eat up all of my time to work on Barkpass.

At the end of the day, Barkpass really won out, and I didn’t give myself space to experiment with other projects. It’s hard to say “no” to something you know has a million things left to do and requires constant focus in order to grow.

I think in a different situation, where perhaps I was sitting on a bunch of cash after selling a startup or a big liquidity event and didn’t have a deadline to provide for my family, I could dive more into this world. I’d like to get back there someday.

Personal Life

In general, I have been much happier during the past four months than I was all of last year. I’m not sure what specifically is making me happier, but to try to isolate a few things:

Complete control over my schedule

I’ve been going to the gym at 12pm instead of 5:15am. This means I can sleep in until the kids wake up, get them going to school, and get into a nice groove of deep work during my most productive hours of 8:30-11:30am.

When I get home from the gym, I’m very relaxed and take the rest of the afternoon to knock out a couple tasks and don’t pressure myself too much. I’m not as tired at the end of the day. 

Note to self: Noon class seems to be key here, and at a day job, it usually gets eaten up when coworkers on the east coast schedule 1pm EST meetings. Maybe I should be ruthless about blocking this off in my calendar?

I really love building products

It’s so fun to wake up with a clean slate and be able to ship whatever the hell I want. I don’t have to ask anybody’s permission to ship anything. I don’t need to align with the product vision of somebody’s boss’s boss’s boss. I can work on some really nerdy tech problem, or some hard business problem, or both — all in the same day.

It’s so dang fun to have ownership over everything. 

Note to self: This will be the hardest part about going back to a full-time job elsewhere. Maybe I can try to replicate some of these things in a work environment that rewards people for extreme ownership.

Singular focus and family time

I’m much better at devoting the 4:30pm - 8:30pm stretch every weeknight to my family since I know I can return to Barkpass in the morning when they’re at school.

Contrast this to attempting to aggressively grow a side business while having a full-time job during the day: I’m faced with a context switch (work vs personal vs side project) and that can be brutal.

When things don’t go well with bedtime, I start feeling resentment towards my children because I can’t get down to work on the side project. People without children might read this and grimace; people with young children will read this and totally understand.

Note to self: This will be challenging, and I will have to be very good about setting boundaries for side projects moving forward. I think having given Barkpass a full-time shot will be good since I know that certain work will have diminishing returns — for example, I don’t need to ship this new feature right now because I know it’s not going to 10x our business overnight.

Better personal health

I get better sleep since I don’t have to wake up at 4:40am to get to the gym. I’m not exhausted at night because I got better sleep.

I’ve also quit drinking on weeknights, including a 40-day sober streak at the beginning of the year, which has led to a lot of benefits.

I’ve started meditating and journaling in the mornings for 10 minutes, which involves getting up at 5am, but I’m way more at peace than if I go to the gym during that same period of time.

Note to self: This can continue for the most part, though I may need to switch back to the morning gym class if I can’t get into the noon class as frequently.

On money

I calculated projections about when our checking account would run dry if I continued to make no real income with Barkpass. This led to feelings of inadequacy and FUD (fear, uncertainty, doubt) which flared up at various points throughout the four months.

However, overall I’m really happy with how well I handled these flareups. I’m also grateful that Bri was willing to keep working and being the primary breadwinner for our family. I’m glad that working at Shopify for a few years allowed us to set aside a bunch of savings in the bank for this stretch of time.

In general, I think it has curbed our spending a bit. There are some bigger purchases we have held back on knowing that we’re only on a single income right now. I don’t think we’ve made any major adjustments to our lifestyle, though. I’m grateful we don’t have an insanely expensive lifestyle that you hear about people creeping into over time.

The funny thing about quitting a big tech job to go solo: the idea of going back to work kinda feels like an “easy way out” – the pay is great, and you can’t wait to go back and “not worry about money anymore.” I feel really lucky that I’m in this industry.

On going back to work

I’m not ashamed of this and feel happy to go back and support my family. Similar to quitting my job, I remind myself that “nothing is permanent.”

I’m really proud that I made the jump to do the solo thing for a while, and I’m really happy about what I learned. It has made me more confident, and I can appreciate better the difficulty that startup founders endure when building a business from scratch.

On returning to Shopify

I recently chatted with Farhan about coming back to Shopify. He said something that made me feel better about “giving up” and coming back to work: he didn’t start his first company until he was 41. Farhan has been involved in multiple startups with exits and now works happily at Shopify. It makes me feel less like I’m “running out of time” — in fact, the opposite.

He encouraged me to write up a framework for deciding whether I’d be successful at a company. Here’s his example. I wrote up my own and shared it on my README.

Farhan also mentioned multiple times that I should “raise my hand” if I’m not in the right place when I come back.

This feels different and the same from when I felt stuck back in 2023. Maybe I always had this level of respect and autonomy, and I didn’t feel like I could exercise it. Or maybe I was convinced that going off on my own was the answer to all my problems.

So bnot a ton has changed on Shopify’s end. What about mine?

I think the keys for me to return at Shopify will be:

Finding good work

Be relentless about this. Don’t feel like I’m in a box, even when I’m told that I should keep my focus in a single area. Don’t worry about stepping on toes or feeling like I’m letting people down. Find work that suits my skill set, be confident in my decisions and expertise, and get shit done.

Raising my hand

Be vocal if I don’t think I’m in a good spot. Be ready to jump around. Ask for help early and often. Use my connections with people to get back to the sweet spot of skill-set overlap and company impact.

Prioritize my personal health and happiness

Take lots of vacation. Block out my calendar to have time for midday gym if that is what I want. Don’t get caught up in team drama or surrounded by cynics. Feed off of the positive energy of people at the company instead getting bogged down by negativity.

On what I would do differently

I don’t know that I would do a ton differently! I learned a ton during such a short window.

Maybe a few years down the road, I’ll find some new project to work on and leave Shopify to go build it.

If anything, it would be really neat to do it with a partner or team next time.

It would also be good to have funding and a better plan for long-term financial stability.

We’ll see! Until then,

✌️