Inside My Brain

Thoughts about startups, tech, marketing, and life

What kind of work gets you in the zone?

I have friends who just love to write, and when they start writing, they just get into the zone and can’t be stopped.

I’ve worked with designers who get into his or her flow, and the creativity just keeps pouring out.

There are people who just love to cook, and they can spend all day in the kitchen.

Amazing things happen when someone just gets so comfortable with and loves the work they do.

Some things come very natural to people, and they’re so good at their work and enjoy it so much that it almost becomes second nature.

I think that’s a beautiful thing.

Unfortunately, after 38 years on this earth, I don’t think I’ve found the kind of work that gets me into a flow state. My resume and career tells that story pretty clearly.

I’m a people person, so part of me thinks my ideal work would be in sales and marketing of some sort, not dissimilar to what I’m doing now. I thought I had a dream job working in marketing for a sports franchise, but that job ran its course, just like all the ones prior.

I’m also pretty analytical, which is why I gravitated toward engineering for my undergrad and grad degrees. And I’m learning Python, which I’m enjoying as well (though it’s hard as shit).

I also like to build things. And I like to write sometimes.

I’m a man of many interests. And that might be holding me back from finding my ideal work.

Who knows, maybe someday I’ll find the work that gets me into the zone. When I do, I’m sure it’ll be a beautiful thing, because it always is.

What about you? What kind of work gets you into the zone? Maybe it’s a specific aspect of your job. Or it might not be work at all; it can be a hobby that you can do all day.

Whatever it is, I’d love to hear about it.

How Chess and Business are Alike

chess board

Whenever we visit Vicky’s family in NJ, my nephew-in-law always asks me to play games, and sometimes we play chess.

This brings me back to the days when I used to play chess against my Mom when I was a kid. I remember enjoying it, but not so much when lost. :/

Anyway, the more I play chess, the more interesting the game becomes, and the more I draw parallels between the game and business.

First of all, if you don’t know how to play chess, you have to learn about all of the pieces and what they can and can’t do. There’s a lot to pick up in a short amount of time.

Then you have to have a strategy that translates to tactics. What’s your opening move strategy? How will you protect your King? Do you like to attack with your Queen early and often?

Of course, you have to understand your competition. What’s his or her strategy? Are they aggressive or defensive? How might they react to your moves?

Throughout the whole process, you have to be analytical. Scan the situation, manage your risk, analyze your options, and select the best one.

Similarly, if you’ve never run a business before, you have to learn about many subjects, and quickly. Depending on the company you’re building, you may have to pick up product development, marketing, sales, customer service, accounting, recruiting, legal, and so on.

Then you have to plot your strategy, tactics, and implementation plan. How will you go to market? What channels will you use to acquire customers? How will you recruit for the skills that you need?

Knowing your competition is very important. How do you differentiate from your competition? Is this differentiation sustainable?

And it’s imperative to be analytical in business as well. Even though creativity and other soft skills are important, you have to know your numbers inside and out. How much does it cost to acquire a customer, and how does that compare to their lifetime value? What’s your profit margin and growth? How can you drive more traffic to your website and increase conversion rates?

It’s no wonder that many successful executives were competitive chess players.

I recently bought a chess board so Vicky and I can play. We’ll eventually teach Maya how to play as well. Hopefully she’ll learn how to be analytical and strategic, discover the parallels between chess and business, and then grow up to be a successful executive. No pressure, though. :)

Don’t be enamored with the vehicle, but what makes it run – knowledge from Questlove

I recently listened to an interview with Questlove of The Roots on Alec Baldwin’s podcast, Here’s the Thing.

Questlove is an extremely thoughtful, introspective, and smart person who had a ton to say about history, dieting, and much more.

But one of the quotes he said that stood out to me was that he “wasn’t enamored with the vehicle, but what makes it run.” I’m kind of paraphrasing the quote because I’m too lazy to go through the interview again to find exactly what he said. Sorry about that.

Anyway, I think that quote is very powerful.

Don’t pay all of your attention to that big end goal. Rather, focus on each specific, smaller task that you’ll have to accomplish to reach that goal, and you’ll achieve it.

Let’s take entrepreneurship, for instance. If you’re a startup founder looking for that big exit but can’t stand the day-to-day grind, you’ll never make it. But if you work hard every day and continue to learn every way to best serve your customers, you’ll have a better chance to build a successful business.

If you’re raising a child, are you longing for the day your kid turns 18 so he or she can go off to college? Or are you enjoying as many moments together as you can?

Are you working toward that one day when you can retire, or trying to make the most of each day of work and enjoy the ride?

Many times the journey is more important than the destination. So don’t be so enamored with the vehicle, but what makes it run.

When little things become big deals – is this a good thing?

A couple of weeks ago I wrote a post about how little things become big deals when you’re a startup founder.

One of the questions that I thought about was whether this relatively small situation having such a major impact on my psyche is a good thing for me.

On one hand, it’s obviously not good at all.

There are a lot of “small” bad things that can happen that can stress out any startup founder or early employee. You might lose touch with a potential customer, like I almost did. Maybe you typed in a wrong number that made you spend a few hundred dollars more on advertising than you planned. Or maybe you inaccurately communicated something to your team that led to confusion about what tasks needed to be done.

These things can add up and really fuck with your mind if you don’t deal with them properly. The stress may lead to poor sleep, crappy work performance, and strained relationships.

Of course, that’s not good for you in the least.

On the other hand, if you put things into perspective, this stress can actually signify a good thing.

It could mean that you truly care about the job that you’re doing. Your reaction to these situations might show that you’re really passionate about your work and the mission you’re trying to accomplish. It might mean that you understand the big impact that these seemingly little things could have.

If you were buried in a large corporation, these little problems might sting a little, but in the long run, they’ll likely be a drop in the bucket and have minimal impact to the livelihood of the company. With layers upon layers in an org chart, these small issues can easily get buried and ignored with little consequence, so you might not care about them as much.

I’m not saying that a startup founder’s job is more important than any other corporate job; I’m saying that in the early stages in a company, little things have a much larger effect on the company.

So when these little things bother you, it can be a sign that you really care about what you’re doing, and are committed to making sure everything goes well for the good of the company.

And that’s a great thing.

Use the hate as fuel to get better

fire-orange-emergency-burning

Last Friday I posted a blog post titled “The life of a startup founder – when little things are big deals” on LinkedIn. 

The very first comment on that post was written by one of my connections who interviewed me for his podcast a while ago. This is what he wrote:

Mr. Chan – Given my 20+ years of experience working with the poorest of the poor and families on the Forbes 50 you are so self absorbed that you think every small detail is the end of the world. I experienced this directly with you in trying to work together. I learned just because I am loyal doesn’t mean everyone will be. Stop only thinking of Mr. Chan. However, my business experience did teach me one thing never put all your eggs in one basket. My money is on your competition !

The situation that led to this comment was a misunderstanding that happened a long time ago. I thought we came to an agreement and squashed it, but I guess not.

While I don’t agree with his comment (obviously) nor do I agree with him using a social network to air his grievances before speaking with me in private, he’s entitled to his opinion about me.

I’m not writing this blog post to disparage him. I have nothing against him. We had a really great interview and hope his podcast is doing well.

But I’ve been thinking a lot about that comment and it’s been motivating me ever since it was written.

You’re going to have some haters out there, whether you deserve to or not.

Maybe your personality doesn’t jive with others.

Maybe your work style is different than others.

Maybe you have to break some eggs to make an omelet, and it’s others’ eggs you have to break.

And when that hate comes at you, you can either crawl into a hole and feel sorry for yourself, or you can use it as fuel to get better and prove them wrong.

I don’t like it when someone comes at me like that. It doesn’t feel good. I’m an overall nice guy and I think most people like me, and I’d like it to stay that way. I know I didn’t do anything wrong in that situation, so I’m not going to let it bother me.

Rather, I’m going to use that animosity to motivate me to work harder, build faster, and get better.

If he wants to put his money on my competition, I’m going to work hard to make sure that he loses that bet.

So don’t let the haters get to you. Use their hate as fuel for your fire.

The life of a startup founder – when little things are big deals

Head in Hands

Here’s a little story about how warped my brain is from entrepreneurship, the roller coaster ride that being a startup founder is, and how my idea of a “win” has drastically changed.

Over the last couple of months, I’ve been doing customer development for my startup, WinOptix. I’ve spoken to over 30 government contracting business development folks to learn about their problems with the BD process and pitch my concept to get feedback.

I learned so much about the government contracting industry and received a ton of great feedback.

And to my surprise, one of these interviewees (let’s call him Victor, not his real name) said that he would pay to have a tool like WinOptix built!

(Yes, I definitely got excited about this at the time, but that isn’t the situation I’m writing about in this post.)

I told Victor I would get back to him soon. I hadn’t even incorporated the company nor did I have the ability to build the product, so I had to get to work on both fronts before moving the potential engagement forward.

At the same time, I was setting up my new WinOptix email address with Google’s G Suite. I emailed Victor from that new account.

Usually I would set up email forwarding to my primary email address so I can manage everything from one account and not have to check multiple inboxes. Except I forgot to do so this time.

Of course, Victor emailed me to set up a time to chat about moving forward soon. And I didn’t receive the email until I checked my WinOptix account much later. UGH.

I replied with an apology. No response. I emailed him again. No response. And again. No response.

I was totally bummed out that I might have missed out on the first paying customer because of a stupid email setup mistake. This could have been huge for WinOptix, and I just banged my head on the wall about how dumb I was and how I screwed up a massive opportunity.

I couldn’t stop thinking about my screw up and how I might have missed out on my first customer. I actually had some trouble sleeping and was down on myself for a while.

After a couple of weeks, I made a last-ditch effort and gave Victor a call.

To my surprise, he picked up the phone! He said he saw my emails and was planning to respond, but had been so swamped that he didn’t have time. And he said he was still interested in working together on the product, and will reach out soon.

I was ecstatic, just because of a simple phone call.

I didn’t even get a firm commitment, but the simple fact that the potential deal was still alive and that I didn’t totally screw it up was a big win to me.

I thought about how this situation – an email setup snafu, a missed email, then the redeeming phone call – is such a small, insignificant blip in the big picture.

But the impact that it had on me was profound.

Then I thought about a couple of things:

  1. Is this relatively small situation having such a major impact on my psyche a good thing for me?
  2. Is my reaction to this situation a telling sign of my ability to be an entrepreneur? Do I need to be more even keeled and steady, and not get so high when good things happen and so low when bad things happen?
  3. Do other early-stage entrepreneurs feel the same way?
  4. What does this situation say about my attention to detail?
  5. If I worked for a larger corporation, what would be an analogous situation, and would I feel the same way?

I’ll write more about these thoughts in future posts. To be continued…

What do you think about this situation? Did I overreact? Have you been through something like this – where a small situation has a profound impact on you? I’d love to hear your thoughts.

Photo courtesy of Alex Proimos on Flickr

When the Guilt Creeps In

I’ve recently realized that I feel guilty more often now than I probably ever have.

It’s not that I feel guilty for doing things in the past that I regret, because I have very few regrets. It’s more like I feel guilty when I don’t do things that I know I should be doing.

For instance, I just was not motivated to work the other day. I was tired, hadn’t exercised in a while (which makes me feel like crap), and just couldn’t get myself to attack important tasks. I completed a few little tasks that took minimal brainpower, but just couldn’t get myself to get the bigger, more important things done.

And I felt completely guilty about it.

I have a ton of projects for work. I have a laundry list of tasks to do around the house (which many times includes laundry), there are everyday things to do to take care of Maya, and a bunch of other general life events going on. And I feel guilty when I’m not taking care of these tasks.

I feel guilty when I check social media instead of working on mockups for my startup. I feel guilty when I sit down to watch TV, which doesn’t happen all that often anymore, instead of searching for ceiling fans to buy for the house. I feel guilty when I read and respond to email when I should be writing that blog post or eBook. And I feel guilty when I read all of these blog posts from entrepreneurs about how productive they are EVERY…SINGLE…SECOND.

I didn’t feel this way in the past, at least not to this extent. Maya didn’t exist 22 months ago, so that was never an issue in the past. But I didn’t feel guilty checking my personal email during my prior jobs. I didn’t mind taking a long break to socialize with my coworkers. I didn’t feel sorry for going to the gym in the middle of the day.

Maybe becoming an entrepreneur changed all that. And getting married. And having a kid. Maybe I care more about these things that are part of my life now, than what was part of my life back then. I’m not sure.

A possible solution would be to not do the things I shouldn’t be doing, and do all of those things that I should be doing, all the time. Then I won’t feel guilty, right?

Yeah, I suppose. But eventually that will lead to burnout.

I think the problem for me is accepting that not all of my time needs to spent on getting things done. Taking some time to do something brainless every once in a while is OK. Actually, it’s probably a good thing.

It’s tough to disconnect from work when you’re trying to get a startup off the ground. But doing so every so often is much better in the long run, for your physical and mental health.  Still, it’s a difficult thing to do.

Do you feel guilty when you’re not being as productive as you can be? If so, how do you deal with it? I’d love to hear your thoughts in the comments.

I’m a man of diverse interests – is that a bad thing?

I have a lot of interests and a broad set of skills. I’m what you may call a jack of all trades, master of none. And I keep wondering if that is hurting me.

Nearly four years ago, I blogged about whether breadth or depth was better for your career.

I started out in materials science and engineering in undergrad. I got bored of it so I didn’t pursue a job in the field after graduation. Instead, I went to grad school for industrial engineering.

Then I went into consulting, what can be considered one of the most generalist professions.

When I got bored of that, I went back to business school and upon graduation, got a job in sports marketing.

Now I’m a tech entrepreneur, marketer, and product guy.

Clearly, I fall into the breadth camp. Or maybe the “get bored quickly” camp.

I was drawn to consulting, marketing, and product because of their breadth. I moved away from materials science because of its specificity.

I’m not saying that I should have stuck with materials science. But if I had stuck to a single function or industry, would I be further along than where I am today? Maybe. I’m not sure.

There are so many conflicting points of view about this. Some say you should focus on your strengths and have others do the rest. Others say to stop focusing on your strengths. Some say focus on one business, others say diversify your life.

I don’t know what the right answer is. And apparently many “experts” don’t agree, either.

I think the important thing is to continue to learn what you need to learn to improve, whether that subject matter is related to your strengths or weaknesses.

I learn a lot about marketing every day and continue to strengthen that strength.

Also, I’m a shitty programmer but I continue to learn to code because I think every tech entrepreneur should have at least some of that knowledge.

But this doesn’t stop me from thinking about whether I’d be better served by focusing on one thing or broadening my skills, and whether my diversity of interests is a bad thing.

What are your thoughts about having diverse interests? I’d love to hear your story.

When patience and perseverance can be bad traits to have

Patience and perseverance are excellent traits to have. But in certain situations, you don’t want to wait too long, or endure for too much time.

I wrote a post a while ago about how raising a kid is like running a startup, and I find that patience and perseverance can apply to both as well.

Being patient with your child is a virtue.

There will be times where your kid throws tantrums and just does things that she shouldn’t be doing. Over and over and over again. Or if you’re sleep training your kid and she just cries and cries and cries and sounds like she may never go to sleep.

And you might lose your cool.

Being patient, persevering, and teaching your child the right thing to do – over and over and over again – will make her better understand right from wrong. And letting her cry herself to sleep, even though it might be painful to hear, will be better for everyone in the long run.

Patience can help your startup and business succeed as well. Software-as-a-Service (SaaS) investor and expert Jason Lemkin says it typically takes 7+ years to truly build a SaaS company. And many founders give up too soon.

It takes some time to learn what you need to learn and do the things you need to do in order to be successful. At least that’s what I keep telling myself.

But when might too much patience and perseverance be a bad thing?

In the sleep training example, maybe your kid is crying for a different reason other than just not being soothed to sleep. She may have poo’d or pee’d, maybe you forgot to give her favorite sleeping toy to her, or it might be too cold in the room. If too much time has passed and she still isn’t sleeping, you should probably go in and check on her.

In the startup world, you have to realize when it’s time to jump ship. You might recognize that the founding team isn’t right for you, and it makes sense to split up. Maybe you see that no one really needs or wants your product, and it’s time to pivot to another idea.

In these cases, you might be wasting your time pursuing things that just aren’t going to work, and the best solution is to not persevere and just move on.

Overall, patience and perseverance are great characteristics to have. But the tough part is recognizing when they are detrimental to your particular situation.

OpenTable vs. Yelp for restaurant reviews – what I learned from making dinner reservations

restaurant_interior

When you’re looking for restaurant reviews, where do you go?

I think most of you would say Yelp. I tend to do the same.

But earlier this week, while I was searching for a restaurant to make a rezzie for Valentine’s Day, I realized that OpenTable has SO MANY MORE reviews than Yelp. Did you know that?

For Rural Society (where we’re going on Tuesday – have you been?), Yelp has 280 reviews, while OpenTable has more than two times the number, 571.

For Woodward Table, Yelp has 370 reviews, while OpenTable has 1136! More than 3x!

For Art and Soul, Yelp has 719 reviews and OpenTable has 3840! That’s more than 5x!

What’s going on here?

The questions I pondered were:

  1. Why is Yelp so much more top of mind than OpenTable when looking for restaurant ratings and reviews?
  2. Why does OpenTable have so many more reviews?
  3. Which site should I trust more when looking for restaurant reviews?

Why is Yelp so much more top of mind than OpenTable when looking for restaurant ratings and reviews?

This is the case because Yelp’s primary reason for existence is to provide reviews of local businesses, primarily restaurants, to its users.

One the other hand, OpenTable’s main use case is to make reservations, and the reviews are a secondary feature.

Thus, Yelp is able to focus on communicating its core value proposition of restaurant ratings and reviews. So when they run online or TV ads, they can focus on how they have real reviews from real people. Then when their users talk about their app, they’ll use the same jargon.

That focus can be a very powerful thing in staying top of mind and acquiring users.

Why does OpenTable have so many more reviews?

The reason why OpenTable has so many more reviews is simple – because they own the transaction of making reservations.

People primarily use Yelp to research restaurants they might eat at. And while you can make reservations through Yelp (they actually had a partnership with OpenTable for years to do so), this is a secondary offering. There are relatively few transactions that happen on Yelp.

You use OpenTable to transact, and that’s a very powerful place for them to be. In order to make a rezzie, you need to sign up and login. Then they can capture and store your info and restaurant preferences, and deliver deals and specials to you.

And because they own that transaction, they are able to prompt you for a review after each time you’ve gone to a restaurant, which is why they have so many more reviews than Yelp.

Owning the transaction was one of the primary reasons why Unilever spent $1 billion to acquire Dollar Shave Club.

Because Unilever typically sold their products through supermarkets and drug stores, they had no relationship with the end customer. They had no idea who was buying their product and how often. On the other hand, Dollar Shave Club had tons of information about their customers’ buying habits.

Apparently, that’s worth a lot of money.

Which site should I trust more when looking for restaurant reviews?

This is an interesting question.

Yelp has done a great job recruiting reviewers who write very in-depth, comprehensive reviews of their experiences. Most Yelp reviews are multiple paragraphs long and many include images. On the other hand, the reviews on OpenTable are typically much shorter and less detailed.

But with Yelp, you can only give a single star rating, which represents the overall experience with your meal. On OpenTable, you can provide ratings for food, ambiance, service, and value, which give the reader a more multi-faceted profile of the dining experience. Both are on a scale of 1-5, which I really hate. It doesn’t give the reviewer enough of a range to give a meaningful rating; I prefer 1-7. Just sayin.

And the amount of reviews! Yelp has significantly fewer reviews per restaurant than OpenTable. If you’re a proponent of the wisdom of the crowds, OpenTable is the place to be.

And from a small sample size that I looked at, it seems like the ratings on Yelp, on average, are lower than that of OpenTable. Are Yelpers more discerning? I’m not sure.

Conclusion

I found it very interesting when I discovered that OpenTable had so many more reviews.

From this discovery, I came to two conclusions.

Yelp will probably still be the first place I look when searching for restaurant reviews, but I think I’ll also refer to OpenTable’s reviews for more context.

I also realized how valuable owning the transaction is for a business; in this case, for amassing a high volume of reviews. OpenTable has a great business where restaurants pay them for every reservation made by a diner, and they are certainly the market leader when it comes to online restaurant reservations.

And even though reviews are a secondary feature of the platform, they are extremely valuable. OpenTable has done a great job in amassing so many more reviews than Yelp. And I think if they wanted to highlight their restaurant reviews to garner more traffic and go head-on against Yelp, they can certainly do so effectively.

Funny how much you can learn from making dinner reservations, huh?

Photo courtesy of Tzahy Lerner on Wikimedia Commons