3 Things to Consider Before Going 'All in' on Your Startup

(This article was originally published on Entrepreneur.com on August 17, 2022)

In 2014, my world flipped upside down. One month after moving from San Francisco to New York, my partner Kayla and I found out we were expecting our first child. Like so many first-time parents, I felt unprepared and that my life had just stepped on a perpetual treadmill and ratcheted up the speed and incline by 2x. We weren’t settled in a home, nor did I feel financially prepared to bring another human into the world. But I wanted to take a massive swing to try and improve the trajectory of our lives. And I needed it to happen in 9 months! 

So I decided to go “all-in”. I was going to quit my job, lock myself in my room with my laptop, and build a master plan that would make our family wealthy beyond our years. After a week in isolation, writing my resignation notice and crafting a handful of half-baked ideas, I had it figured out! 

This. Is. Impossible. 

We needed health insurance. We needed a salary to cover our basic living expenses. And we needed one another for emotional support. So I needed to change my perspective on what “going all in” really looked like, to build the business and life that would get us there. Going “all in” would be a process, not a single moment in time. This is what that process looked like for my family and me.

Don’t quit your day job. 

When I started Disco, Kayla didn’t have the best maternity plan from her employer at the time. We needed my day job to cover our basic living expenses and our health insurance, as well as to ensure that we didn’t blow through ALL our savings to support an extended unpaid leave period for Kayla and our daughter Laura. 

In terms of how I split my time, I spent two hours every morning connecting with Laura before my day job started. I spent two hours in the evenings with my family to ensure we were able to connect at the end of the day. From the hours of 7:00pm until 1:00am, my co-founders and I worked together on the business, 7 days a week. That left us 5.5 – 6 hours of sleep before my daughter would wake up. We did this for almost 8 months before we had a product in the market with real paying customers. 

We didn’t come from generational wealth. Knowing that it’d take at least five years to build a meaningful business, we had to be smart about how we allocated funds to get the business rolling while supporting our family. It wasn’t until we were officially accepted into 500 Startups with that traction that I officially resigned from my day job. If you have adult responsibilities, keep your day job to handle those responsibilities and use your evenings to build your Rocketship. 

Go broad to go narrow. 

When we first started our company, I found myself looking for silver bullet solutions and the path of least resistance. The reality is that in the earliest stages of building your company, you may have early product usage and early revenues but you might not know if you truly have PM fit. When I pitched Marc Benioff my startup in 2014, I knew we had early signals in a big problem space, but I wasn’t entirely sure that we had true product market fit and ultimately came up empty handed.

To find the idea worth going “all in” on, we needed to go broader to test a wide range of potential product concepts, quickly and inexpensively. We used tools like Webflow and Invision to mock-up product concepts to socialise with prospective customers before building anything. Once we had strong customer validation, we could go narrow to refine the product concepts that showed the most promise and then apply engineering effort to those concepts. We’d have to repeat this process several times over the course of the six years we spent building Disco as we focused on true product market fit. 

Do things that aren’t your startup. 

The first months of Disco were intense without much sleep or personal time; However, after we were accepted into 500 Startups and was able to transition out of my day job I was able to regain some personal time to re-invest in myself. Initially I struggled with guilt believing that I needed to fill that time with my startup but found that my productivity suffered greatly. The data in our CRM validated how I was feeling. I was generating 15% more leads; However, my customer close rate dropped by 20% when I spent more time working on the business. So, I began to incorporate a few things into my weekly routine.

Move your Dad or Mom bod. In the mornings I incorporated a daily run with my daughter in her BoB stroller which gave us more time together and helped get my Dad bod back in check.

Take a lunch break. I worked out of my apartment complex, so I was able to break every day for lunch to spend it with Kayla and Laura.

 Get some sleep. I made sure to get at least six hours of sleep each night (or at least tried to if Laura managed to sleep through the night!)

Learn to cook. I learned how to cook. This helped provide more balance on the meal prep side of things every evening, but also ensured I was putting good food into the Dad bod.

Get support. I sought out therapy to find an outlet that wasn’t my co founders or Kayla to share the challenges I was feeling as a first-time parent and a first time founder.

“Going all-in” looks different for every founder that’s taking their startup from zero to one. 

Building our company took a little longer than so many of the “overnight successes” you read about, but I wouldn’t change anything about our journey. You’re no good to your co-founders or your employees if you’re not good to yourself. So don’t also forget to go “all in” on the people you love and yourself. You won’t regret it.