1. Product Vision / Competency
2. Quality Recruiting and Team Building
3. Ability to Execute and Get Results.
4. Ability to Pitch and Raise Financing

1. Product Vision

Founding CEOs are responsible for product vision.  They are architects of products or services that don’t yet exist. In the beta stage of DL, I worked primarily with one designer to create all the pages in Photoshop and a wireframe program. Basically, I was a pixel pusher. “Pixel perfect” became my mantra. Then the founding team collaborated to create the product experience together. Along the way, the founding team contributed immensely to help mold the final product, but I still care about every pixel that goes into production.  All of our people in tech and design have heard me say our product needs to be pixel perfect! This obsession is the basis for refining our product.

2. Quality Recruiting and Team Building

I have met quite a few entrepreneurs who think they can do it by themselves. But having had some failed business partnerships over the past 10 years, I know that the most important thing is to build the right team from the start. You must have the right business partners! Building a great team isn’t just about credentials. There are intangibles that are difficult to identify but even so it’s critical to identify them.

3. Ability to Execute and Get Results

As a startup if you don’t get results quickly, raising money from investors can be difficult. The longer you have been executing, the more data investors have on your performance. By contrast, if you show a mixed bag of execution over a long timeframe, the investor may be doubtful. If you don’t perform well, investors will question your ability to execute, your level of commitment or both. Along these lines, it’s really important to continually update investors so they have the big picture. Is there a story behind a certain result in the numbers? The investors need to know.

4. Ability to Pitch and Raise Financing

Some entrepreneurs are gifted at communicating their vision and seemingly raise financing effortlessly without great vision, people or results. I wasn’t blessed with this gift, so I’ve had to prove #1,#2, and #3 in order to raise financing.  But in the grand scheme of things, the first three are more important for long term success and financing will be almost automatic if those conditions are met. I think Ben Silbermann of Pinterest falls into this category. Ben’s a great entrepreneur but many people declined the early opportunity to invest in Pinterest because the company had yet to hockey-stick. In my opinion Ben isn’t necessarily a showman. He’s more of a quiet, thoughtful guy. I think this affected his ability to fundraise early on. But eventually those tangible characteristics - #1, 2 and 3 – won the investors over.

By contrast, there are going to be companies that burn through investors’cash without ever creating substantial value. And there will always be investors willing to gamble on companies that lack fundamentals because some of them do succeed even with poor fundamentals early on.

As mentioned in #3 above, having bad results can turn investors off. But at the end of the day, people invest in the team and the story, not the data or the PowerPoint. So while bad data is never a good thing, investors know that the data can and will change. But regardless of the data, investors will never get behind a bad team because it’s possible to have good data in spite of having a bad team.

One thing I’ve learned from being an entrepreneur is that being decisive is everything.

I once had lunch at a sushi restaurant with one of our vendors. I was pleasantly surprised by the quality of the fish but I was particularly impressed by the uni. After the meal we chatted for a few minutes in the parking lot. Out of the corner of my eye I noticed a small delivery truck driving through the parking lot. In mid-conversation and without warning, I started running toward the truck.

While sprinting I managed to get my phone out and snap a photo of it. You see, while I was having the conversation I had noticed that the truck had a picture of uni on it. Naturally it had to belong to the restaurant’s supplier. After having eaten such amazing uni, I made a split-second decision to get the supplier’s information. I wanted to order uni straight from the source.

This is the actual photo I took.

I got in contact with the supplier and eventually finagled a way to purchase directly from them. Now I can get live uni straight from the source at about half the regular cost. I even host uni parties at my house, which have become quite popular.

My conversation partners definitely thought that I was strange to run off like that but the thing is, if you are really passionate about something as I am about sushi, you are willing to go to extremes in order to get what you need. I had a chance to seize the moment and I knew I might never get that opportunity again. So I had to be decisive and I had to move quickly regardless of how it might look to my vendors. Opportunities are rare and they are valuable; we have to be bold in taking advantage of them, many times trusting your gut.

When we started DailyLook I asked my psychologist friend to administer a professional Myers-Briggs test to each of the founding team members. It was important to me that we understood not only ourselves but each other because it’s critical to our company’s success. It was quite interesting and helpful to learn how each of us prefers to communicate, in addition to learning why we work well in various ways.

According to the test I am Extroverted/Intuitive/Thinking/Judging (ENTJ). The most valuable lesson from this is that it helps me understand the type of leader I am. I have a strong tendency towards decisive action and execution, which is an important characteristic in a CEO. But this trait can also be one of my greatest weaknesses. Sometimes I am not in tune with others’ feelings and I can be too blunt or critical.  Running a fashion company is very different than say a software or services company, and I have to constantly keep this in mind so I can be a better leader for our team. It’s all about self awareness.  

Knowing myself and my senior leadership team better will be progressively more important as each of our jobs increases in complexity and responsibility. In addition, we’re adding members to our team as DailyLook scales up. Those new additions will have to complement and adapt to the existing personalities on the team.

Being that we are a creative AND data-driven company, I believe that we need to build teams that are in a healthy state of tension. I can’t do that if I can’t identify the right people; tools like the Myers-Briggs test help me accomplish that.

Beyond just learning about myself, I’ve also invested time into genuinely learning about the 16 other personality types. It has helped me to quickly understand and assess what individuals can work together to have a winning result. Over time, I continue to invest time in understanding strengths and weaknesses in people.

Another tool I’ve used is Strengths Finders, which helps identify your personal strengths amongst 32 characteristics.  My #1 strength is Achiever, and it explains why I can sustain endless energy to execute day in and day out. Like Myers-Briggs, Strengths Finders also helps me pick the right leadership composition to build a winning world class team. 

If you want to be an entrepreneur and grow to become a CEO, it’s incredibly important that you know yourself to a fault and understand others for what they are now and what they could be.  I recommend that you start with Myers-Briggs and Strengths Finders.  Both have helped my personal growth incredibly during this journey.

1. You have to be great at dealing with stress. A successful entrepreneur does well during extremely stressful situations. Think about how zen-like Phil Knight, Tiger Woods, or Phil Ivey look during extremely stressful situations. Often the difference between winning and losing is how well you perform under stress. As an entrepreneur, you’ll be tested often. If you can lose a significant amount of money and shake it off that’s a good start, because it happens to every entrepreneur.

2. Embrace the fact that you will never feel completely secure. If you run a fast-growing start-up, you’ll always feel insecure about the future. You’ll constantly revisit and question your decisions. The perpetual state of not knowing what tomorrow will bring adds to the stress level and can be overwhelming for some, but it’s important to acquire a taste for this feeling. For me, it’s part of what makes me feel alive.  As Andy Grove said, “Only the paranoid survive.”

3. It requires all of your commitment and focus. I have met many entrepreneurs who are working on a side business and a full time job. While there may be cases of this working out, I’m a believer that to be truly successful you need to make the jump and be totally committed to starting a business. Otherwise you don’t maximize your chances of success.  Building a new business from scratch is hard – it deserves all of your attention. I think becoming an entrepreneur is like trying to do a backflip for the first time. You have to fully commit to have a chance.

4. You have to be fiercely competitive.  If you aren’t naturally competitive, you will need to learn to be. I’m not saying that being nice, humble, or friendly is incompatible with competitiveness. But being competitive means you truly understand what it takes to win. John Chambers, the CEO of Cisco, is a warm Southern gentleman. But you’d better believe that he is an intensely fierce competitor.

5. You don’t do it alone: your friends, family and relationships WILL be affected. Every day and every hour, your life will revolve around your startup. You will have to carefully assess how to use what little free time you do have. And even then, that free time may be taken from you without forewarning because the startup will pull you away like a crying baby needing its mother.

6. It’s going to be painful at times. Assuming that you don’t start off wealthy, being an entrepreneur is going to be painful.  So it’s good if you get used to pain. Part of the reason I do crossfit is that the workout kills me every time and I have to really focus on mental strength to make gains. Truthfully, I don’t even enjoy it during the workout but I do it to stay mentally tough and physically healthy.

7. It does not end until the exit. There’s no pause button. Unless you are building a lifestyle business, be prepared for a relentless 10 year marathon. There are not many big businesses that were built in less than 10 years and even building a nice lifestyle business will take at least 3+ years of 80+ hour work weeks.

8. At times, you’ll have to let go of people you care about. At some point, your business will either decline or you’ll hire some good people that are the wrong fit. It kills me every time I have to let someone go that I care for and respect as a person. It’s especially difficult knowing that a person’s livelihood depends on their job.  It’s one of the worst parts of being an entrepreneur and yet the decision eventually becomes a necessity.

9. You’ll have to be a workaholic for the first few years. An important characteristic of being an entrepreneur is the ability to work really long hours without getting paid and without considering it to be “work”. You have to avoid the multitude of distractions the world offers you. While your friends are meeting up for happy hours or planning their next vacations, you’ll have your head down focused on building your company.

10. It’s all on YOU. At the end of the day, the buck stops with you and you shoulder ALL of the cumulative actions and decisions of your business. As an entrepreneur, if you don’t get results, it’s your fault. If you don’t grow, it’s your fault. If your product sucks, it’s your fault. If the business fails, it’s your fault.  As an employee, you can point fingers and defer responsibility. As entrepreneur / CEO, you can only blame yourself.

Despite all of the cons above, I am blessed by the opportunity to be an entrepreneur.  The media often glorifies entrepreneurs and I want to paint a more honest picture of reality.  My work makes me feel alive, gives me purpose and it’s incredibly rewarding to work with great people who believe in my vision. So if the reality of being an entrepreneur sounds fulfilling to you, then figure out how you’re going to make it happen sooner than later. My point here is to show that there are a million reasons not to do something but only one reason why you should. The biggest thing holding entrepreneurs back is never actually starting. So start now!  

Over the years I have had six cofounders between three businesses. Three have been great fits and three didn’t work out. In the ones that didn’t work, the problem boiled down to two things: commitment and values. Surprisingly, skill set and experience were not the main reasons for failure.

Commitment

It’s not easy recruiting a high-paid executive or successful entrepreneur to come work for a new startup. Nobody goes into entrepreneurship without making a giant leap of faith. The right person has to be willing to walk away from a 9-5 job or successful venture and start working insane hours for something brand new and uncertain. That’s not an attractive proposition to all people. But the point is that you have to commit. It’s like doing a backflip, you have very little chance of success and certain failure if you don’t commit. I’ve had cofounders who didn’t have the right level of commitment and when that’s the case, it just won’t work out. No matter how you rationalize it, if one person carries the majority of the workload it leads to an inevitable breakdown of the team. Having co-founders with the same level of commitment is paramount to your success and happiness as a team. My current founding team is totally bought in and no one ever has to think about every person carrying their own weight. It creates a high level a mutual respect, trust, and execution.

Values

My goal is to build a world-class product and experience.   At one point I had a cofounder who was really talented and successful in his prior projects. But his philosophy was about building low cost leaders. Our business values were too different for us to be successful together. There are many ways to make money and build companies. But if co-founders have different values, it’s hard to be in sync and ultimately the differences will be too much to form a strong dynamic partnership.

At the end of the day, successful teams don’t just have great chemistry or the smartest or hardest-working people. The team has to be greater than the sum of its parts and those parts have to match up on multiple complex levels. I’ve made some mistakes by choosing business partners based on their prior success or history without really understanding their values and motivations. The best business partner I have had is one whom I worked with for years before we became cofounders. They say that you should date around before you get married. This is true of co-founders, investors, and board members too. You’ll save yourself the headaches, heartache, and gray hairs. 

I’m totally addicted to sushi. But sushi is not what it used to be. Actually, I’ll say that sushi is not what it’s supposed to be. Traditionally, sushi is a very simple and pure food. The rolls that are commonplace in the US don’t even exist in Japan. A Japanese guy told me once that they wouldn’t even consider that type of food to be sushi.

 By contrast, real sushi is unadulterated and it’s very simple: a slice of high quality fish on a small, slightly warm ball of rice with just the right amount of vinegar and a touch of wasabi. In many cuisines, experimentation and fusion of styles is encouraged but that is not the case with sushi. There isn’t a whole lot to it and there shouldn’t be distractions when consuming sushi. Sushi is a true purist’s food and there’s absolutely nothing else like it!

 But the simplicity of sushi belies the difficulty of making it. If you’ve seen Jiro Dreams of Sushi, you know that something like preparing a baked egg cake can take years to master if it’s made the right way. That sort of unrelenting focus and effort is what I aspire to as an entrepreneur. In the same way that sushi gives me so much joy, I want to build a product that delivers a simple and pure value proposition because I think customers will appreciate that. Just as I don’t like crazy rolls with lots of ingredients, I don’t want to deceive the customer with too many bells and whistles. I think that having too many ingredients in sushi (or too many features in a product) makes it easy to conceal basic flaws. By contrast, creating a simple yet delicious piece of sushi is really difficult. It’s even harder to innovate while keeping things simple. 

  To master the art of sushi, a chef has to make a lifelong commitment to sushi as a craft. The chef has to stick to strong basic values and resist following the latest trends. DailyLook’s central ideal is about providing the best styling and fashion inspiration. Everything we do has to fall in line with that goal and we have to be disciplined in order to stick with our philosophy. 

 I don’t love sushi just because it’s delicious or healthy. It represents what I strive for: quality, simplicity and purity. This is why sushi is my vice.