How Two Young Cofounders Paid the Rent Without Jobs (Or Breaking the Law)

Behind the Hustle & the Grind

Justin Boogaard
Subversion
6 min readJan 4, 2018

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David and I have gone through a lot together.

Before GoGoGrandparent, David had started his own successful app business and I was working as a Product Manager at a tech company in Los Angeles. We didn’t know each other at the time, but we were both looking to start a new business and both independently decided to start attending three day events called hackathons — where teams of people who have never met spend three days making a project that then gets judged by panelists.

We were on the same team at Santa Clara’s Startup Weekend and made an app that optimized social media profile photos. The project was fun but ultimately ended after the weekend. Several months later we met again at another hackathon in San Francisco — this time winning a cash prize.

By this point I had started to build up a lot of respect for David. He was action oriented. He is the type of guy that can stay up all night if needed to do what needs to be done. He prioritizes a project’s goals ahead of his own, he compliments other people’s work and also isn’t afraid to communicate when he thinks something could be better.

Do the Hustle

While I was living with my Grandma I’d do a bunch of odd jobs for money. An idea came up to put all the available odd jobs in the city onto a website that people looking for contracting income could go to for work.

When it came time to put the pedal to the metal, I knew there was really only one person I would consider working with. I called David about the idea, we talked for four hours and by the end of the call he had decided to drop his life up in the Bay Area, move to LA and get it done. We called it ‘Hustle’ because one of the people we interviewed when we started testing out the idea said it would help a lot with their hustle.

Grandma’s house was really only big enough to accommodate two people and so after a long discussion with her we decided I should try to find a place close by where David and I could live and work together. We found a month-to-month lease in Studio City, contributed $5,000 to cover a few months of rent and got to work.

Our business model was a recruiting model — businesses looking for short term contract work would tell us what type of work they needed to get filled and we’d build those opportunities into a calendar our community of Hustlers could follow to make money on their own terms.

Over about 4 months, we learned that Hustle didn’t really offer most businesses tremendous value. It’s much easier for local businesses to recruit labor than we originally expected. Hustle was making money, but we were basically becoming a recruiting agency for Postmates and Instacart. Their success dictated our success, which wasn’t a position neither David nor myself wanted to be in.

One morning after grinding on this for four months, David made the call that we shouldn’t work on it anymore. It was incredibly hard to hear but he was right. We stopped all our recruiting activities and started thinking up other ideas.

On the Grind

The name of the game was “Pay the Rent.”

The objective was to figure out a way to make $1500 a month and it had two rules:

  1. We couldn’t do anything illegal;

and;

2. We couldn’t get a job.

If we lost the game, he’d go back to the Bay Area and I’d go back to grandma’s house.

The stakes were high and the rules were simple.

Over the next two months David and I sold water on Santa Monica Pier, tried to sell rewards programs to local businesses for their employees and even figured out a way to encourage people to download Square Cash which at the time was paying out a $5 referral fee.

At one point we decided to try to Kickstart a jewelry box. While pursuring his Master’s in Architecture, David had designed one for an ex girlfriend, but unfortunately the CAD files were on his computer at his parents’ house in the Bay Area.

Fortunately David did what David does — gets it done no matter what. Without a second thought, he disembarked on the six hour drive from LA to the Bay Area and back so we could try getting this jewelry thing 3d printed.

We managed to add three more months of rent to our runway but nothing we did solved our original problem; we hadn’t found anything that could ‘be big’. After 6 months of working together we decided to give up.

During those 6 months we had pieced together the knowledge required to build basic coding projects. Rather than move out right then and split our remaining rent money — we decided to spend our last months working on getting better at code.

Through all of this I had been visiting my grandmother every Sunday. It was the Sunday after we had made this decision that she asked if Uber had a phone number.

I told David about her request and he said we should give it one last shot. David worked on keeping us alive by packaging what remained of Hustle into a software package we could sell to one of our customers. Grandma’s ‘last shot’ led to an investment from the startup accelerator Y Combinator. That brought us up to Mountain View where we live today.

Now that GoGoGrandparent is getting bigger it’s clear we are going to be doing this for a long time. One night a few months after moving to Mountain View, when I was feeling particularly bright about the future I asked David how big he thought GoGoGrandparent could become. Did he think we could ever make a million dollars? Ten million dollars?

Despite months of financial struggles and thinking about how we’d cover the next rent check he said:

“It isn’t about the money we can make. We don’t need a lot of money. I want to help as many people as we can. What we should really be asking ourselves is: How can we help people live?”

We’ve been doing that ever since.

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Justin Boogaard
Subversion

Helping people access on-demand services in order to age independently and confidently at home.