The Second Hardest Fight of My Career

This month marks nine years in the startup world for me. I've been on the founding team of multiple, including my own. They've all had many of the elements you might expect. The excitement of the idea, the turbulence of finding the right team, and the satisfaction of impactful work, to name a few.

This latest arc I've taken with Bubbles has centered on (and pushed me to a limit to) something I had only seen in my days as a Founder-CEO: the thrill of the fight.

Just five months ago, we challenged ourselves with a question:

Will we remain a simple tool for recording your screen, or do we dare to become something transformational?

The question was daunting, and the leadership team was split.

On the one hand, we have a loyal userbase that loves us as a personal tool in their back pocket. On the other, we see a massive opportunity for an app on the forefront of modern workplace communication. One is the bird in the hand, but the other is a whole lot more than two in a bush.

Accelerating into our original vision would require a Herculean effort at rapid speed. We would need to rebuild our infrastructure from the ground up, rebrand, flip our marketing strategy on its head, and build 2x more functionality in five months than we built in the past year.

We believe asynchronous video can transform remote work for the better, and we're on a mission to make it happen.

We were worried, but we took on the fight. We worked long hours together and made challenging decisions. Many of us dedicated holidays, birthdays, and weekends. We had to dogfood and redesign in parallel while simultaneously peeling back legacy code and keeping everything stable.

The fight ended with an epic all-nighter to make our release date. A date that also happened to be... the day Silicon Valley Bank was seized by the FDIC ??!

This was a six month journey that felt like a Hollywood thriller. Like all good movies though, there is an ending worth sharing...

Today we officially announce Bubbles for Teams ??! We're all systems-go, and I would love to hear your thoughts. We believe we can take 38% of your live meetings off your calendar. Check us out on Product Hunt here: https://www.producthunt.com/posts/bubbles-for-teams

Bonus: fight highlights! ??

1. Finding product-market fit

Many startups use their MVP in a way that aligns with their ultimate vision. But, because that vision is in the distance, the functionality isn't there yet. So they marry it with internal tools and processes to bridge the gap.

We built a system we called 'Notion Flags', which we've used to great effect. It let us keep things on track without decreasing focus time. So one day I asked Taylor LeCroy , "Hey what would Bubbles + flags look like?"

We all LOVED that look.

But we had to make it intuitive and digestible, and prove people wanted it. We did three qualitative studies. Here's how I'd represent them:

Study 1: "This is pretty cool, I'd try it!"

Study 2: "Hmm this seems interesting, but I'm not sure about that price..."

Study 3: "Wow! That price is nothing for what this does for me. When can I start??"

You can imagine the rollercoaster we went through here. Mind you, in study 2, we were already well underway on building this thing ??.

Takeaway: sometimes the price hurdle is just about whether they fully get it.

2. Building the base

When we finished our initial spec for Bubbles for Teams, we all took a deeep breath. We were going from an application essentially concerned with a single entity (the 'bubble') to an application with many interconnected entities (teams, spaces, bubbles, and users). The design was completely refreshed, and the 'Notion Flag' concept involved a complex timing system with many levers and notifications.

This wasn't an epic. It was an overhaul.

We decided to reverse engineer scope from our launch date. This made us realize we needed three new engineers, and we needed to onboarded them quickly (shout out Telescoped and Caleb Michael !). Everyone rose to the occasion and I'm so proud of the work we did. It was remarkable to be a part of!

???? Andrew Locke D.J. Sitte Norman R. Higor Alves Ivan Filho well done!

Takeaway: if you're bringing tough news to your team, bring it to them early, and sign up together.

3. Keeping current users close to heart

With such intense focus on new use cases, we had to try not to lose sight of the users that got us to where we are today. They care about quickly grabbing their screen, made accessible via link. That's it. A huge challenge for us was maintaining this while expanding our product.

To be honest, we dropped the ball in some areas here. We tried so hard, but we needed to try harder. We've made big strides in the last two weeks which improve the speed and intuitiveness of this experience, but there's more to do yet.

Takeaway: loop your fans in early. Give them beta access and learn, even if it means pushing back launch.

4. Staying sane while working to the max

This process took a lot out of me. I had to lead both product and engineering while still programming heavily. I put my life on pause for months and did nothing other than work, or recover from work.

I'm not complaining - this was my choice! It brought me great satisfaction and the lessons will be lifelong. I also had immense help from my teammates who led just as much as me (?? Tom Medema and Taylor LeCroy ).

I found improvements in my diet and exercise routine that increased my baseline energy and recovery from burnout. I also rediscovered my love for martial arts, which refueled discipline, optimism, and passion.

It required a real mindset shift I once learned from a brilliant young Martial Artist named Bruce ??.

Takeaway:

#entrepreneurship #startups #siliconvalleybank #technology #motivation #productivity

P.S. wondering what my hardest fight was? Ask any founder-CEO ;)