Roger is the Co-Founder and CEO of Novel, a no-code solution that leverages Apple and Google wallet passes to drive customer retention for Shopify storefronts.

Prior to Novel, he traversed a varied career as an economist, a software engineer with three patents to his name, and the founder of Smartrr, a subscription tech company. 

We don’t often talk about the management of stress and mental health during the extremely demanding moment that is bringing a business from zero to one. Roger has done this successfully twice. 

This interview took place last year while he was deep in launching Novel and he shared openly about how he maintains a peaceful mind in the midst of intensity.

On his morning routine.

My wake-up time ranges. On the days that I have an AA meeting, I’m up at 7. If I’ve had a later night, I’m up at 8:30. 

To boot myself up before actual work begins, I’ll do 10 minutes of vigorous exercise as soon as I’m awake. I have a home gym set up for pull ups and dips and such. Starting companies can be unpredictably demanding so this makes sure that at the very least, I get in 10 minutes of rigorous motion in the day. 

Then I’ll have a Taika Oat Milk latte and take my HVMN ketones before I hop on the subway.

On stress relief.

The morning exercise routine is a great start psychologically. Even if I have a less productive day, at least I’ve accomplished something from the get-go. 

There are also some critical things for me to do for my own spiritual and mental health. I treat these things as needs, not wants. Even at an extremely intense time when I’m running on two hours of sleep, I make sure I do them. 

Otherwise, I could start to spiral — and then people counting on me for reassurance could lose it too.

One of those critical things is family time. The weekends, at a minimum Sunday mornings, are reserved for being present with my wife and our son. 

Another one is attending AA, which I have done now for 15 years.

Addictive personalities fundamentally have a hard time finding peace and fulfillment. For me the solution has been finding fulfillment through service beyond myself and in doing so letting go of ego and self-centered fears.

The aspiration to be of service is at the foundation of me as a person and it’s how I keep a level head through the tough times.

On the Stockdale Paradox.

The hardest times of a startup are easily those zero to one, initial deep-building periods. You start out, the whole company is just you and a laptop, maybe a co-founder or two, and you need to will it to life.

It’s what you earn your equity for: charging headlong into uncertainty and making it work. A million things could go wrong, so you need to balance that mode of putting on blinders and cranking with pulling your head up and checking the direction you’re going. It can feel impossible sometimes, but you need to do both.

It’s a unique thing to go through and requires a belief in yourself that’s hard to have sometimes.

During a low moment during my first fundraise for my first company, another founder shared with me the Stockdale Paradox. The story goes: 

• Admiral Jim Stockdale was a prisoner of war in Vietnam for eight years. 

• Someone asked him, “How did you make it through that psychologically: never knowing when or if it would ever end?” 

• Stockdale responded: “You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.”

It’s a paradox because he’s pairing short-term objectivity with a long-term faith that is actually irrational. At that time, he could not have known that he would be out in eight years. Reading deeper though, he’s saying that if he had lost that faith, that itself would have ensured failure.

His statement is about the balance: relentless belief in yourself without the false comfort that would come from ignoring the brutal challenges in front of you. 

None of us are prisoners of war in Vietnam — which itself helps Stockdale’s quote lend perspective to any of our first-world issues — but his advice translates well for anyone trying to build from zero to one.

“You can and will succeed but you must be completely clear-eyed in navigating through every micro and macro challenge along the way.”

On core values as a founder.

With no background in entrepreneurship and in spaces that were totally new to me, I built two businesses in one year and in doing so created over a hundred million dollars of value. 

There were a few guiding principles which helped me do that.

1. Bridging business and fun

I’ve always been turned off by the false dichotomy that strictly divides the “serious” and “focused” from the “entertaining” and “fun.” 

Through my fortunate successes, my life as a founder has been both a serious commitment and a grand adventure.

2. Honoring commitment

I uphold two promises to anyone who chooses to join us. 

First: In my two ventures, incredible folks have left a lot of cash on the table to come join whatever I was working on because they trusted me. That’s extremely motivating and meaningful to me, so in return I promise them I will do everything I can to make this the best career decision they’ve ever made.

Second: I’ll never ask someone to do anything that I wouldn’t do personally, I’ll never ask them to work any harder than I’ll work. There’s nothing less inspiring than a leader who commands but does not contribute.

3. The team win

Building a business is building a community of team members, investors, partners, and customers around the shared vision of maximizing the benefit of everyone involved.

The beauty of a startup is that in economic terms it’s a positive-sum game.  There’s a real opportunity to achieve the team win. That vision has to be the shared driver of everyone at the company. I learned the hard way in my first business what happens if I hold that vision but bring in others who do not.

For Novel, my co-founders Anna, Brian, and I look for values alignment through a track record of selflessness and integrity in everyone we hire.

It’s simple to filter for; we ask the question: “Who is the person you have elevated the most?” For the people we want, the hard part is that they can only pick one.

On his nightly wind-down.

For the last 30 minutes or so every day, my wife and I sit together, watching a show and hanging out while I take a break or do mindless ops work.

I get to focus on just sharing space and conversation with her. 

In the grand scheme of things, meeting the love of my life at the age of 22 in a laundromat in Boston — a week after I moved there — is hands down the luckiest moment of my life. Having her as a life partner gives support and meaning to any short-term sacrifices I make towards building something of consequence.