Taking Care of Your Health While Running A Startup

The first time Zachariah Reitano founded a startup, he went through the Y Combinator program and found himself rushing back and forth between New York City and the Bay Area while struggling to get the company up and running.

“We fell into the stereotype of young founders who felt they needed to stay up all night. We often pulled all-nighters unnecessarily,” he said. “Sleep is not a gas tank. You can’t run it to empty and sleep all day on Saturday.”

He pushed so hard toward exhaustion that he walked into a hospital and literally fell asleep — only to be revived by getting an IV plugged in.

“That was a definite wake-up call.”

This time with his next company Roman, he’s doing things differently. It’s a common experience we see at Initialized Capital — that second-time or serial founders become more disciplined about the way that they manage their health and well-being while running a company.

The idea for this new company itself grew out of Reitano’s early experiences as a teenager grappling with erectile dysfunction.

At 17, he told his father about his symptoms. A doctor, Reitano’s father knew immediately that the condition at such an early age could be an indicator of more severe, underlying health problems. “It’s your body’s check engine light — it could be the first symptom of heart disease, depression or high cholesterol,” he explained.

Not long afterward when Reitano was exercising one day, he stopped to check his pulse and noticed he had an irregular heartbeat.

He collapsed. His heart had stopped.

Once he came to, he realized that in order to fix his heart issues, he would need to have a cardiac ablation to eradicate tissues that were triggering arrhythmia.

While Reitano’s health is in better shape about a decade or so later, those experiences re-emerged in conversations with his then boss and now co-founder Saman Rahmanian. They’re building a direct-to-consumer line of men’s health products, starting with erectile dysfunction medication.

Not only are they focusing the business around men’s health, both founders have tried to really embody health as a value in their company culture and in their daily lives.

“Messaging in this society tells you that to be a real man, you have to ignore your problems,” Rahmanian said. “When we think of men and health, we think of men who go to the gym to just get ripped. But at Roman, we think of men as people who are in relationships to others in their lives and to society who want to make sure they have productive lives and fix problems, whether that’s the garage door not working or their body not functioning.

Here are some practices that Reitano and his co-founder Saman Rahmanian, also a serial founder who started Managed by Q, use to keep themselves steady while building Roman.

Institute off-the-grid time

Reitano started having regular weekly dinners on Sunday night with a close group of five to six friends. “We shut off our phones. We don’t check our e-mail,” he said.

Both Rahmanian and Reitano have some sort of practice related to this. Saman puts his phone in airplane mode for about 1 1/2 hours each evening after work in order to catch up with his wife and four children.

No phones are allowed in the bedroom — only downstairs in the common area. “Also, when the kids are around, the phone is basically taboo,” Rahmanian said.

During work, they sometimes have “deep work” or dark mode, where they snooze all notifications from the rest of the team and turn on a sunglasses emoji () on all of their internal communications systems to tell the rest of the team not to disturb them.

Zachariah went even further. He dropped all social media, including Instagram, Facebook and Twitter — although he keeps Facebook messenger on his phone in order to text with friends. Every morning, he and his girlfriend have morning no phone coffee meetings with each other where they reset and discuss current priorities. Saman never had much of a social media presence and eventually just deleted Facebook’s app off his phone.

Make sure to keep up physical exercise

Every Friday before work, Reitano and Roman’s third co-founder Rob Schutzgo for a lap swim.

Rahmanian, who has found it hard to motivate himself to get to a gym, found that incorporating a routine into his commute home works well for him. So he found a gym that’s on his way back home.

Choose co-founders that you would work for, not just with

Another component of well-being is making sure that your relationships, including professional ones, stay strong. While Reitano is the CEO, he says the best way to choose co-founders is to find people that you would not only be willing to work with — but for — as if they were your boss. Saman and Zachariah met at Prehype, a pre-seed incubator firm where Rahmanian is a partner.

At Zachariah’s first startup, he and his co-founder were close friends from college. But that didn’t mean that they were meant to work together.

“Just because you’re right for each other in college, doesn’t mean you’re meant to be married or that you have the right ingredients to be co-founders together — even if that person is incredible and would be an unbelievable co-founder for another person,” Reitano said. “If you have the right soil, you can grow almost any type of plant. What happened with me and Saman, is that I started working for him and then realized I had never been so happy to work with someone.”

Cultivate better co-founder relationships

Once every six weeks, all three Roman founders get together out-of-office for the entire day for a North Star meeting. It’s a no-computer all-day meeting where they analyze the past, present and future of the company with an agenda-driven conversation.

“Our conversations are like three people trying to find a path,” Reitano said. “None of us are trying to win an argument. None of it is adversarial. It’s so insignificant about who is right that our conversations have a very different tenor.”

He added, “All three of us are running together. It’s like a treasure hunt together and the more we can find out something with data, the more we know where to look.”

How charging for our product originally hurt — but ultimately saved — our startup

Five years ago, my co-founder Claire McDonnell and I founded True Link Financial, and did two things that that were totally unorthodox for the time.

First, we didn’t build a startup for teenagers.

We built it for seniors. (We’re a financial services firm that offers debit and Visa cards and investments management for aging Americans.)

Secondly, we charged our customers actual, real money for what we had built.

This was not common practice at the time. Around 2012, we and a whole cohort of other startups — Simple, Plastc, Swyp, Coin, Final, Stratos, Clinkle, and others — were getting card-issuing companies off the ground.¹ We also launched a Visa card — but our goal was to protect older folks from fraud, a $36 billion problem that affects millions of Americans, including my grandmother. Our cards would automatically decline scammy transactions so seniors like my grandmother would be able to still carry a credit card, preserve their independence, and spend their own money — and in order to decline the transactions we had to become the issuer of the card.²

Investing in the future of retail with Standard Cognition: Bringing real time computer vision to all brick-and-mortar stores

Standard Cognition is building the retail experience of the future, where you just walk out to pay for whatever you’re carrying out of a store. It’s seamless, checkout-less shopping for consumers and retailers all over the country.

We’re proud to announce that we just joined Charles River Ventures and Y Combinator in backing the company through an initial $5 million round.

In their first proof of concept, they use cameras to identify who walks in, what goods they’re carrying and what they ultimately purchase. All of these processes are handled on-site at the local store using computer vision techniques Standard Cognition is developing.

The most interesting innovations happen when technology cost curves hit magic levels where they become possible in new packages for the first time. Realtime computer vision with off-the-shelf GPUs has just reached that level now, and we are excited that this team is bringing it to reality today.

The team has not only founded a company together before, it has three PhDs in mathematics and nuclear science and its CEO Jordan Fisher led a team at the Securities and Exchange Commission developing quantitative tools that could make sense of the agency’s data.

For retailers, this will lead to reduced prices, no lines, better stocked shelves and fewer misplaced items. Every year, retailers lose $45 billion to theft, so even before the holy grail of checkout-without-lines, Standard Cognition can make a huge dent in anti-theft in a way existing solutions have only dreamed.

Technology cost curves unlocking new capability is only half of it. To bring amazing tech to market, you also have to have a strong business motivation to do it, and frankly we’re there today. Traditional American retailers face an oncoming crisis as e-commerce continues to take mindshare and revenue directly from brick-and-mortar retail. Standard Cognition is such a powerfully better customer experience that this is the kind of thing that goes from cool to must-have in very short order.

Instacart’s Lead Product Designer on Creating A Design System

Jordan Staniscia tried — and claims he failed — multiple times to create a single, re-usable design system for all of Instacart’s visuals, icons and interactions over many years at the company. 

We at Initialized Capital frequently get asked about how startups should create style guides that define the brand identities of their companies, and so we asked Staniscia to share some lessons with portfolio companies this week. 

So, first off, what is a “design system”? 

Staniscia prefers to use the word “system” because it implies that this is something re-usable; it’s a framework. Design systems are, in Josh Clark of Big Medium’s words, “containers for institutional knowledge.” 

It sits between the design and engineering teams as a common language that helps them stay on the same page. Otherwise, designers will end up in a situation where they have to explain their product vision over and over again and engineers will have a hard time ensuring they’re building an efficient system.