I started to ponder about going out on my own towards the end of my 20s.

I was an inexperienced creative director at R/GA, one of the most respected digital agencies. I had been there for close to five years and I was knee-deep in my work, particularly on Nike. I worked long hours, including weekends, but I was enjoying what I was doing.

I wasn’t married, didn’t have kids, etc. I was still young. These factors, depending on how you look at work and life, could be helpful when starting a company. However, not only did I not know how to do it, I felt completely inadequate in several areas. Experience, network, money, recognition, and knowledge, to name a few.

Around the same time, I started to get emails and phone calls from recruiters. That was new to me but it did make me wonder what’s outside the fences, an apt description since there was a fence in front of R/GA’S building in New York City.

The conventional wisdom about quitting, as I was told, was that I should get an offer first and then resign. That felt uncomfortable to me so I ended up talking openly to Bob Greenberg, my boss at the time and an absolute industry legend, about how I should think about my future.

I was tempted to stay but I did leave R/GA and joined AKQA, an agency that was not well known at the time. When joining, I told myself I’d give it a go for at least five years to challenge and build myself. I ended up staying close to 11 years, an eternity by today’s standard, particularly in the US job market.

Through the course of 20+ years, I only quit twice. Both times, it didn’t go well. That’ll have to be another post.

Seven laws

In my 30s, I asked a lot of questions about starting a company to people that I thought I could learn from.

During an interview with a CEO/founder of a very respected creative agency network, I got curious about how he started his own. By the end of the interview, he said to me “I’ve never had anyone that I’m trying to recruit ask me so many questions!” I’d like to think he meant it as a compliment as he later befriended me on Facebook. Is that a stretch? Probably. He didn’t hire me.

There are numerous articles and books about starting a company. There is also plenty of literature for designers and creatives with useful tips and tools. I read many of them while I was pondering but in retrospect, the pieces of advice that resonated with me and became most useful were the ones from my design and creative friends/colleagues who had charted the course before me.

The pieces of advice from them were so crisp and memorable that I can still recall exactly where I was. As I continue on my journey of being a design and creative entrepreneur, I am reminded over and over again how right they were. I’ve learned a few lessons on my own also.

I’d like to give credit and thanks to those friends who gave the advice to me over the years. You’ve been generous and I’m forever grateful.

Law 1: Find a trigger

“You’ve been saying this for the last five years. Now, congratulations and welcome to the club.”

PJ Pereira, the co-founder/creative chairman of Pereira O’Dell, and one of my closest friends said this with a big grin when I told him that I was starting my company Inamoto & Co, now I&CO (the part about ‘grin’ is a lie since I told him over the phone but from his voice, that’s what I pictured). PJ had started his agency five or so years prior and was doing well.

Every time he and I would catch up over a meal in our respective cities-New York and San Francisco at the time-I would ask him little by little what I should know about and be ready for. He told me many things including “Be ready to work like crazy.” This turned out to be not so in my case. My business partner and I found a trick to this and I’ll save that for another story time.

One piece of advice from PJ during one of our meals that resonated with me the most was “Find a trigger.”

A trigger is one of three things:

1. Person/people: The person/people you start a company with. In my experience and opinion, this is by far the most important trigger. It also is the most important factor to make a company endure.
2. Money: When we want to start a company, we need some cash to manage our company and our finances immediately. This could be in the form of a client who’s willing to take a chance on us and give us our first project to get going.
3. Idea: A specific idea for your business. Ironically, we, the creative types, tend to struggle with this the most, in my experience. I’ve known so many who’ve said to me “I want to go on my own, I want to start a company but I don’t know what idea to go with.”

I had an inkling of an Idea (#3) but not fully formed. On our way home with Rem (who lived a few neighborhoods away) one day after work, I said that we should start a company as a joke. The next day, he asked me if I was joking. “Well, I was but not really.”

When we started, we didn’t have a client.

“The thing is,” said PJ to me a few years before that, “you won’t get all three at the same time. Just look for one trigger and then go.”

Law 2: Do the math. Be stoic.

“Start saving, Rei,” said Glenn Cole, one of the co-founders of 72andSunny.

He had called me wanting a reference for someone who used to work for me. In return, I asked him about starting a company. I met him and his partner John Boiler first at a meeting for Xbox, a client his agency 72andsunny and AKQA that I was working for shared from 2005 or 2006 for multiple years. Their agency was 20 or 30 people back then. We’d be in many client meetings together and I learned a lot from both Glenn and John.

Glenn’s advice was very practical. When we start a company, we could go without a paycheck for months on end. We need to have enough money in our personal bank accounts to support our families. We also need to pay people before we get paid by a client.

The math to manage the finances of a company is not too complicated. It’s basic arithmetic, not calculus or even algebra.

When we work for others as creatives, we don’t like to think about money. We are notorious for ignoring money, among many things. That’s probably why we sat at kids’ tables. And when we did get to sit at grown-up tables, we would say things like, “We need to invest in ideas, in the Work, in the office, etc” The word invest is an easy word to rely on when we want to avoid being financially responsible and accountable.

“Before you start, save as much money as you can. And after you do, be willing to take on freelance work to keep going. Shed your ego.” said Glenn.

Don’t spend more than we earn. It’s that simple. Do the math. Be stoic.

Law 3: Build your brand

I met Brett Lovelady of Astro Studios while working on Xbox also. An industrial designer by trade, he spoke so eloquently in meetings about design, strategy, and business and I was always in awe. Plus, he was so down to earth and exhibited no bravado. The work he and his team has done is gorgeous. He has also developed products, such as headsets for gamers or watches, and turned them into separate companies. I secretly took cues from his business model, if I were to confess.

“Build your brand, Rei.” It was over lunch at a Thai restaurant that he had invited me to in San Francisco. I remember being surprised by this.

“You want to be known for something. People will want to hire your company because of you. It’s not just about The Work you make. Build your brand.”

In 2023, the good news is that there is a myriad of ways to build your brand, particularly using social media. The bad news is that with social media, it’s easy to get caught up with the number of followers and likes and that can be distracting and misleading. I know people who have more than 50k followers on Instagram but are having trouble making enough money or getting clients. I also know people who have 5k followers and are successfully earning more than $250k.

The difference? Authenticity and point of view.

To develop your brand, we need to be who we really are. It sounds cheesy, I know. But with the rise of generative AI, these factors will be more important than ever.

Search for your voice. Develop it over time. Build your brand.

Law 4: Hire female

This advice came from none other than Cindy Gallop of MakeLoveNotPorn.

I met Cindy in 2009 on stage in Tokyo and kept in touch ever since. That year she launched MakeLoveNotPorn at TED and her speech went viral. Several years later, we found ourselves in Tokyo coincidentally at the same time so we were doing lunch at Andaz, one of my favorite hotels. It was before the Met Too movement entered the public psyche (2017). I love how consistent Cindy is with what she says long before everyone else.

Once Rem and I left our previous jobs and started to look for people to join our starship, we were particular about what kind of people we wanted to hire. The Idea for our company was at the intersection of design, data, and technology and we wanted our first set of people to be the representative for each. Our first hire was Nathalie Torres, as the Director of Research and Data. We hired Nathalie because we knew she was good (we had worked before), not necessarily because she was female. She continues to be part of the family.

One thing that I’ve never been very good at is practicing empathy. My various family members tell me that I’m selfish and self-centered. Having Nathalie, along with other female senior leaders at I&CO, has helped me be more empathetic to others.

Maybe I’m typecasting, but we, males, just aren’t that empathetic. Females can teach us men a lot about how we should behave in life and at work. Hire female.

Law 5: Have the stomach

Over drinks at the Martinez in Cannes one year and in his signature deep voice, Paul Lavoie, co-founder of TAXI, a famed advertising agency he founded with Jane Hope in the 1990s in Montreal, told me. “Have the stomach.”

Outside of running his agency, Paul was the president of the Art Directors Club and I was invited to join the board years ago. I would see him a few times a year at the board meeting. With a shaved head, an intense gaze, broad shoulders, a tall figure, and a deep voice, he had a presence. A Paul Lavoie presence.

I realized that he was right within the first 12 months of launching the company. And several years after that.

Toward the end of our first year, I received a letter from a lawyer accusing me of certain activities that were made up. The letter threatened that they would sue us if we continued. I won’t get into the details here but that kind of incident WILL sink our stomachs.

Several years later, the world got hit with COVID and we all got hit hard. Many of us had to make some tough decisions. No matter the reason, when we have to make those decisions, we feel them in our stomachs.

I had spent more than 15 years working for someone else, growing their businesses, managing teams, dealing with clients, etc. Along the way, there were plenty of stomach-sinking situations but I always had a cushion because I was an employee. Those situations did train my stomach. The benefit of starting a company in our late 30s or even 40s is that we have seen and gone through more in life and know how to deal with them better.

Regardless, have the stomach. We will need it.

Law 6: Two is the optimal number, like in a marriage

Back in 2011, I saw this tweet by Elias Bizannes. I tweeted that “When setting up a company, you need 3 types of people: a Hustler (a marketer), a Hacker (a developer) & a Hipster (a designer).”

A few months later, I gave a talk at SXSW with the same quote and it got tweeted heavily. It was the first time (and might have been the only time) what I said was trending on Twitter.

Since then, multiple people have written articles and posts like “The Dream Team: Hacker, Hustler, and Hipster” and “Building your dream team.”

This 3H theory gave a clear impression that we need three people to start a company. But I said it several years before actually starting a company and didn’t have the hands-on insight just yet.

Having started a company, I now believe that the optimal number is two, like in a marriage. Let me explain.

I still believe that this ‘Hipster, Hacker, Hustler’ theory applies when we are designing and building a product and trying to sell and grow it.

Designers and creatives don’t typically like to sell so we avoid being Hustlers. We like to stay cool and be Hipsters. The reality is, though, we have to sell and hustle the minute we start our companies. We need to be both Hipsters and Hustlers. That’s why this 3H theory doesn’t fit so neatly into three separate people.

In addition, starting a company is much more like starting a family than a product. If we have three people to start a family, well, that can get awkward and complicated as you can imagine. Also, the more people we have, the more it’ll be difficult to agree on things. Worse, what’s harder is resolving when we disagree.

Starting a company alone is like raising twins as a single parent, as someone said to me once. It’s not impossible but can be very hard.

Like in our personal life, finding the right partner to start a company with is the most important decision of our professional life.

Two is the optimal number, just like in a marriage.

Law 7: Search for Why

In my 30s, I went through a mental exercise of trying to figure out the rest of my professional life. Ultimately, the two most important things to me were making a positive impact on the world and being in control of my own destiny. I thought starting my own company would bring me closer to those goals than working in someone else’s corporation.

After starting a company, it’s also ok for the Why to evolve.

Back when I first moved to the US for college in the 1990s, Japan was revered as an economic powerhouse. However, in the last quarter century, the strength of the nation has deteriorated thanks to a series of miscalculations by the government and several other factors. As a Japanese native, it saddens me to watch my motherland become weaker on the world stage. Japan used to matter more.

Within months of our starting, the first client that gave us a chance was UNIQLO, Japan’s biggest apparel brand and one of the biggest in the world. We continue to work with Mr. Tadashi Yanai, the founder and the global CEO of UNIQLO and its parent company Fast Retailing. Gradually, we started to get inquiries from other Japanese clients and we opened our office in Tokyo in 2019. We now have multiple C-suite relationships with the likes of Toyota, ASICS, and Panasonic, among others.

I&CO is a group of experienced strategic thinkers and makers and we work with forward-thinking leaders to shape the future of their business. By helping Japanese brands succeed in AND outside of Japan, a relatively small company like ours can make an impact on Japan through them.

We can help make Japan matter again. That’s now part of my Why.

Before we start a company and after, we need to keep reminding ourselves. Search for Why.

To summarize, here are the seven laws for creative entrepreneurship:

1. Find a trigger.
2. Do the math. Be stoic.
3. Build your brand.
4. Hire female.
5. Have the stomach.
6. Two is the optimal number, like in a marriage.
7. Search for Why.

Thanks for reading. Please hit reply with feedback.

Originally published at https://reiinamoto.substack.com.