Photo credit: Tùng Lê Bá

Many indie-hackers here are solopreneurs or partnering with co-founders. The different co-founder combinations you find include brothers, long-time friends and ex-colleagues. But the combination of husband and wife as co-founders seems to be less discussed in the IH community.

Sam Altman once said, "Cofounder relationships are among the most important in the entire company.” I can think of many reasons why having a spouse as the co-founder is a high-risk undertaking, thus the road less taken. The stress, anxiety, and uncertainty of starting a business can test the strongest relationships. Most people simply don't want to tangle business with personal life. It can get messy. Unintended consequences can be personal or even irreversible. A partner compatible in life might not be complementary in business.

Before I became Chris's 'partner in crime' in bootstrapping, I did not deliberate the potential side-effects of starting a business as a couple. After jumping the corporate ship, I was steeped in enthusiasm to work with Chris and thrilled to be my own boss. Yet as time went by, we began to face our own set of problems not just as minted entrepreneurs, but also working as a newly married couple.

Personalities clashed, egos bruised, and maybe even a bit of heart-breaking involved along the way. You might think bootstrapping a side-project into a legit business is as hard as it is, and then topping it up with a married life's mundane minutiae? That certainly sounds nothing less than a nightmare.

But somehow we've made it work. At least, until this far. After working together for almost 7 months on CozyCal, a scheduling software tailored to individual small business owners and freelancers, we are generating $600 MRR. This amount is not quite at the level of "ramen profitability" that could sustain the expensive living costs of Vancouver, Canada. But we rein in our budget and spend on only what's necessary to grow CozyCal.

The "honeymoon" period

Harking back to June of 2017, the startup Chris had worked for unfortunately dissolved. I also handed in my resignation at a Fortune 500 company shortly before that. 

"It's time to go home", we thought. 

After living in New York City for almost 4 years, the novelty of the city’s hustle and bustle has worn off. As much as we love the city’s liveliness and our awesome friends, we moved back to the nature-surrounding Pacific Northwest.

Now, with both of us working on CozyCal full-time, our days and nights are preoccupied with growing CozyCal and acquiring new users. As a software developer, Chris's focus is on the technical side of CozyCal. Most of his time is spent on coding new features, fixing bugs and improving the efficiency of the underlying 'infrastructure' of CozyCal. I, on the other hand, focus on the non-technical side of CozyCal, spending most of my time collecting feedback from users, building our website, and finding new leads.

Being a two-person team, we are able to run CozyCal in a lean manner, with quick iteration cycles and low overhead cost. Slowly, we are getting more trial users from the Wordpress directory, which brings about 95% of traffic to CozyCal. Most users are individual small business owners from all walks of life. They are wellness professionals, life coaches, photographers, personal trainers and other types of service professionals who are dedicated to provide value to their clients and community.

Using Webflow, I'm able to create a decent looking website for CozyCal.

The power struggle

As the thrill of having early adopters wore off, the pain of growing CozyCal began to seep in. There's a tradeoff that comes with being a two-person team: limited manpower and resources. We could only build so fast and iterate so quickly. As it slowly dawned on me how crowded the scheduling software space is, I was feeling clueless as what I should work on to pierce through the noise. For over 4 months, our MRR remained stagnant at $400.


The "honeymoon" period is followed by a painful, stagnant period with almost 0 conversion for over 4 months.

The pressure of generating leads, converting trial users and building new features is becoming insomnia-inducing. What used to be friendly bickering began to escalate to bitter crossfires and sometimes even mutated into hostile personal attacks. Without the boundaries of a formal working environment or obligations to act collegially, our approaches to communication is unhindered, spontaneous and even 'abusive' at times.

When we are in the heat of argument, I would wield my client management skills as an-ex consultant to justify the necessity of fulfilling each user's wish for new features, while Chris would defend his stance on being strategic on building features by highlighting his tenure as a seasoned developer.

"We should listen to our users' needs and build whatever features they ask of us or we are going to lose all of them!" My voice quivered with panic as I yelled at Chris.

"No, no and no! We can't possibly build every feature that's asked of us. Over-promising and under-delivering are the worst! " Chris shouted back while busy quoting Intercom's Product Management chapter on "Product Strategy is About Saying No."

"I'm done with this. I don't want to be at your mercy every time and have you decide which feature to build and not to build. I'm gonna find a job!" failing to negate Chris's argument successfully, I stormed out of the door.

"I'm not stopping you from doing whatever you want. Go ahead!" Chris cried behind my back, knowing that my unfounded tantrums were telltale signs of self-doubts.

Then 10 minutes later. I walked back into the room, and sat down next to Chris.

"So, do you want to have a quick stand-up meeting to prioritize our feature pipeline?" I looked at Chris with a hint of apology.

Chris opened a new Trello board and started to type in the meeting title and date. "Sure. Let's go over all the feature requests we've received so far..."

The decision process is like a shifting see-saw as we both fight to win the upper hand.

So here it goes, a typical day in our daily operation of CozyCal, peppered with melodrama and frictions here and there. There's a lack of a 'company culture' between us. 

We just know each other too well, painfully well. 

It's difficult to leave our personalities, egos and feelings completely out of the picture when we're working on CozyCal. The line demarcating work from personal life often blurs or even completely disappears. A harmless conversation about what dishes to order in a restaurant could branch off to a fervent debate about whether CozyCal has the right product-market fit.

Having worked at two startups prior to bootstrapping CozyCal, Chris is familiar with the product development cycle of software businesses. While coming from a healthcare consulting background, everything in the tech world is new to me. I'm used to meeting hard-set deadlines, fulfilling clients' every single request and following supervisors' orders.

While Chris prefers flexibility in product development timeline, I prefer to set hard deadlines for each feature on the roadmap; while he blocks off time to work on pre-delegated tasks, I insist on addressing urgent needs of customers once they arise. The free startup spirit in Chris often clashes with my rigid corporate-trained work ethic.

Vancouver had a glorious summer and early fall from July to October, yet to us, it felt like the winter came too early.

Working as a team is not optional but mandatory

It's true that there are times when we hardly speak for a whole day because of disagreements on details as small as modifying the gradient backgrounds of the booking page. But there are also times when we get so pumped from positive feedback that we work late into the night.

In late October, things started to pick up a bit. We launched the new booking page design and it was well-received among our users. In addition, with Intercom installed within CozyCal, we were able to refine the on-boarding process, chat with leads in real-time and close tickets at a rate faster than ever. Even though the Wordpress directory is our only channel of traffic, we could see that the increased engagement with users led to greater product 'stickiness'.

CozyCal's new booking page allows direct editing of the settings.

Using Xmind, I created an Intercom messaging campaign that targets different user segments in our funnel.

As Chris and I begin to make more informed decisions based on data captured from ProfitWell and Heap, we also have a better understanding of each other's working style and complementary abilities. Routines are established, weekly tasks are delegated in advance, and daily stand-up meetings are held to keep us focused.

Friction might be inevitable for a two-person team like us who work and live together. But between us, there are no politics or back-stabbing. We have the advantage of affording to be as transparent as a team can be. If Chris needs more time to refine a feature before shipping, I'll make sure not to push him and leave enough time for him to work on it. If I'm experiencing anxiety, Chris is there to hear me out and offer words of encouragement.

Maybe the absence of a boundary between work and living isn't a bad thing. Maybe it's okay to engage in 'crossfires' about CozyCal's new dashboard design during our anniversary dinner. Our work relationship is like a mirror that reflects the way we treat each other in a married relationship: we fight and get caught in "cold-war" zones, but eventually we break the silence, listen to each other, iron out the kinks, and doggedly move forward.

Bootstrapping a business, especially doing it with a loved one, demands learning a different set of skills, and more importantly, adopting a different mindset. Yes, it comes with risks, and yes it feels like riding an emotional rollercoaster. But through the process of overcoming the challenges together, our bonds are not weakened but rather strengthened.

We are both attracted to the idea of entrepreneurship, firmly believing in the empowerment of bootstrapping and being indie hackers. Sharing the passion to create a valuable product that solves real problems, we remind ourselves that it's a privilege to work with each other. For me, building CozyCal is no longer about climbing the corporate ladder or to nail the next promotion during the upcoming calibration cycle, but how to overcome the constant self-doubts and quickly learn and apply new skills for CozyCal's growth. 

I'm grateful for having a partner that shares all the experiences, bears the brunt of growing pain, and listens to my struggles with no judgements.

What's next?

We are splitting our digital nomad days between working on CozyCal and exploring new places in Thailand.

Now, we are traveling in Thailand on a short 'sabbatical' to try out the digital nomad lifestyle. Looking back at the past 7 months, it was a short journey packed with ups and downs of bootstrapping CozyCal. More importantly, it was an intensive learning experience for both of us. Finding the fine and delicate balance between growing a business and maintaining a relationship as a couple entail no short cuts, and little hacking. What it takes is patience, mutual respect and a lot of conscious effort.

I hope this post gives you a glimpse into our life of bootstrapping CozyCal as a couple. I'm not trying to impart any lessons on how to bootstrap a business with your spouse here, because each couple is different. But If you're considering working on a project together with your spouse, I'd say give it a try!