Important Things Startup Founders Should Know

Being an entrepreneur can be a pain in the ass. Especially if you’re not prepared for it.

Fortunately, there are a lot of generous people offering sage advice. David Shen, an advisor & investor of early stage Internet startups, tries to talk people out of being an entrepreneur. Starting a business is not for everyone. If that’s the case for you, the sooner you realize it, the better.

I talk about the time commitment. I talk about my early Yahoo days when there were just a bunch of us, and we worked our tail off for years. I talk about the long hours we spent building Yahoo back in the day, the stress, the do-everything-yourself mentality and the chaos of not knowing what’s coming next. I tell them about the fact that relationships have broken up due to training for Ironman, which even at its peak, doesn’t equate to time commitment spent at a startup and for a longer period of time. I go through the inevitable ups and downs that come with relationships and families of entrepreneurs; it’s not an easy place to be when your work and family demands collide.

Dharmesh Shah, founder of HubSpot, also offers ten critical questions that startup co-founders should ask themselves:

  1. How should we divide the shares?
  2. How will decisions get made?
  3. What happens if one of us leaves the company?
  4. Can any of us be fired? By whom? For what reasons?
  5. What are our personal goals for the startup?
  6. Will this be the primary activity for each of us?
  7. What part of our plan are we each unwilling to change?
  8. What contractual terms will each of us sign with the company?
  9. Will any of us be investing cash in the company? If so, how is this treated?
  10. What will we pay ourselves? Who gets to change this in the future?

To these great questions, I would add two derived from Shen’s advice:

  1. Do we all understand the risks and commitment required to be an entrepreneur?
  2. Is everyone willing to fully take those risks and honor those commitments?

It is not easy being an entrepreneur. But if you understand the risks and commitment required, you will have a better chance of survival.

Photo by: Team Dalog

I’m a PC vs I’m a Mac

Now for some Friday fun.

You know those “I’m a PC” Microsoft Windows 7 (MSFT) TV ads with the cute Asian kid? The ones that make you want a cute Asian kid more than Windows 7? (Zing! haha)

Her name is Kylie Kim and she’s been getting some attention, like from Sony VAIO and The Ellen DeGeneres Show.

So you know what that means. Time for a parody!

Via: 8Asians.com

Reading True North: Knowing Your Authentic Self Exercise

How well do you know yourself? The fourth chapter of True North: Discover Your Authentic Leadership strives to help develop self-awareness by assessing your leadership strengths, shortcomings, and development needs.

The True North exercises:

Basic Self-Awareness Assessment:

The following questions compare how others view me with my own perception. I asked several friends & colleagues to rate me. Below, my self-rating is provided, followed by the averaged score from the others. A 10 is a “very,” 5 is a “moderately,” and 1 is a “barely.”

Question Self-Rating Feedback Rating
How self-confident are you? 8 8.5
How aware are you of your moods and emotions? 9 9
How effective are you in regulating your moods to minimize their impact on other people? 8 9
When confronted with situations that are displeasing to you, how well do you take the time to think clearly about them before responding or reacting? 8 8.25
When you receive critical feedback from others, how well are you able to take in the feedback and respond in a constructive manner without acting defensively? 7 9.25
How well do you understand the emotional makeup of others and their needs? 9 9.25
How sensitive are you in relating to others’ needs and helping them? 8 9.25
How skillful are you in building lasting relationships? 7 9.5
How well do you network with others and create networks of people with common interests? 8 9
How effective are you in leading teams? 8 8.75
Do others follow your lead voluntarily? 9 9
How persuasive are you in convincing others of your mutual interests? 8 8.5

After reviewing the feedback, to what extent do you see yourself as others see you? How strong is your basic self-awareness right now?

I honestly thought I was being a little cocky with my self-assessment. Instead, it seems I am a little hard on myself. Just a little. To be cocky again, I would say my self-awareness is pretty darn good right now.

Strengths and Development Areas

What are your strongest capabilities or talents?

One of my strongest capabilities lies in an empathic nature that enables me to connect with others.

Way back in fifth grade, my teacher told me, “Never judge a person until you’ve walked a mile in his shoes.” That maxim stuck with me, permeating my everyday thoughts and interpersonal encounters. Every time I engage in a discussion or debate, I put myself into the other person’s shoes to understand his/her point of view.

Oddly enough, this happens so much that I sometimes find it difficult to be righteously indignant with people if I can understand why they’re being insulting or arrogant, even if I feel like I should be righteously indignant with them. Go figure.

Other capabilities and talents I consider as strengths are an analytical temperament, the ability to think critically, the comfort of making mistakes and learning from them, and the desire to constantly set and strive for long-term goals.

What are your strongest attributes as a leader?

As a leader, my empathic nature allows me to build strong relationships and inspire others. I know I’m not an expert in every field I want to be an expert in, so I’m thankful for the brillant friends I’ve made.

There’s this anecdote about Henry Ford that I like. During an interview, he told a reporter to ask him any question he wanted about his business’ operations. So the reporter asked for an obscure detail, like how many nuts and bolts go into a Model T. Ford then picked up his phone, called one of his lead engineers, and and gave the reporter the answer.

Ford’s effectiveness as a leader was not that he knew everything there was to know about his business’ operations. It was the relationships he made, the people who worked with him, and his social network. I aspire for the same kind of effectiveness.

What are your greatest needs for development as a leader?

There are situations where I am nervous and out of my element. Public speaking, approaching investors, talking to the media, and similar situations can be nerve-wracking. I’m sure I’m not alone in these. But as a leader, these are necessary skills to learn.

Toastmasters was one solution I used to use. Once my schedule clears up, I plan on finding a local chapter and continuing. The best way to approach investors, in my opinion, is to not need them, bootstrap, and build a great business. Then they’ll come to us. As for speaking to the media, well, perhaps I’ll attend a media training workshop when the time comes.

Needs

Do you need structure in your job? To what extent are you comfortable with ambiguity and change?

I love ambiguity & change, personally. Too much structure & routine bore me. My attention span at any particular role is about one year. After that, I tend to need drastic change. Before joining Yahoo! (YHOO), I stayed at companies for approximately one year. While at Yahoo, I was lucky enough to change roles & responsibilities significantly enough to keep myself engaged. My career there progressed this way: web developer -> technical manager of a small team -> technical manager of first-line managers and a larger team -> senior product manager. Each role was on a new property with a new team; each was different enough that I was always challenged. That’s the way I like it.

What level of financial security will allow you to feel comfortable?

I know how to live within my means. It is a cross between bare necessities and a handful of luxuries. To be honest, I’m fairly comfortable right now, though I will be getting married and starting a family soon, so my financial needs will be increasing.

To what extent do you need to be leading a team?

That’s a good question. I never thought about it as a need. But I sure enjoy being a leader in some way. If I won the lottery and never needed to work again, I would still start a business or non-profit venture. So perhaps I do have a need to lead.

How much time do you need with your family or loved ones each week?

Family comes first, always. I need as much time as they need me. Way back in college, I planned on entering this industry because of the ability to work from home. That meant being able to take my kids to softball games & guitar lessons, spend time with my wife, and take care of my parents if & when they need me to.

How much personal time do you need each week to recharge?

Perhaps a few hours a day. I’m not a morning person, so the first couple of hours in the morning are generally spent slowly charging up and getting ready for the day. Then at night, I like to unwind with my family or a good book. Writing also serves as a way to recharge.

Your Authentic Self

What are your vulnerabilities, blind spots, and shadow sides?

I certainly have some pet peeves. I’m impatient with impatience. I’m close-minded about close-minded people. And people who speak in absolutes absolutely bug me.

I know, I just wrote that I’m empathic and can walk in other peoples’ shoes. But I have my limits, especially if someone’s ignorance, arrogance, or obnoxiousness is directed toward someone I care about. If it is aimed at me, that’s fine. I can take it. I can even take criticism; I’m far from perfect and I know it. But leave my loved ones alone.

Admittedly, my memory isn’t as sharp anymore. To compensate, I’ve gotten into the habit of relying on digital solutions to extend my memory. This means using Google Calendar (GOOG) to manage my schedule, Gmail to manage my tasks, and my Apple iPhone (AAPL) to give me access to those tools wherever I am. It’s an efficient system, though I really need to do some brain teasers & memory games so I’m not a total moron when I’m a grandfather.

To what extent do you use defensive armor as a shield to protect yourself from exposing your vulnerabilities with others?

Everyone has defense mechanisms to protect their vulnerabilities to some extent, that’s only natural. I am a fiercely private person, if you can believe it. There are aspects of my life I will never share online, especially if they pertain to my family. But everything else is filtered appropriately. Even my online presence is part of my privacy strategy – if I can control what appears online (my personal brand, so to speak), then I can control what is seen and what is hidden. The genericness of my name also helps with the hidden part.

Back to vulnerabilities. This could be the New Yorker in me, but I’m laced with what I consider a healthy level of trust (or lack thereof) for complete strangers. I don’t share my vulnerabilities with a stranger, nor do I believe they are out to screw me over. As I get to know someone, my trust & comfort level with them increases; inversely, my defensive armor decreases. But to a point. To see any more of my vulnerabilities means you need to get into my inner circle of family, friends, and colleagues.

At the same time, I believe most people strive to be good and not overtly malicious, though we are all born selfish. I give most people the benefit of the doubt. So I share my thoughts, lessons learned, and whatever advice I’ve picked up with complete strangers. It’s my small effort in perhaps helping one other person in this huge world of ours. To the extent where I can share a vulnerability and connect with that person safely and without consequence to me or my family, I will do it.

How can you become more comfortable in sharing your vulnerabilities with others?

I am comfortable with my vulnerability sharing levels at the moment. I don’t think it serves any good to pour my heart out to a prospective client, for example. Nor should I hold all of my frustrations in. Everyone needs an outlet. I have mine, which include my inner circle. My circle of trust, where I keep nothing from you, you keep nothing from me, and round and round we go.

How comfortable are you with who you are right now?

I am very comfortable with who I am. I am an idealistic realist; I am content with my life, but not satisfied. This means I’m unsatisfied enough to strive for more. At the same time, I’m content, happy, and very grateful for the life I have and the decisions I’ve made. And I look forward to the future eagerly.

How would you answer these questions?

The True North exercises:

The Audacity to Lie for Your Career

I’m not here to join the controversy. Apparently Clay Shirky stirred some up with his post, “A Rant About Women.” I’m here because something he wrote gave rise to a memory. Here’s what he wrote:

When I was 19 and three days into my freshman year, I went to see Bill Warfel, the head of grad theater design (my chosen profession, back in the day), to ask if I could enroll in a design course. He asked me two questions. The first was “How’s your drawing?” Not so good, I replied. (I could barely draw in those days.) “OK, how’s your drafting?” I realized this was it. I could either go for a set design or lighting design course, and since I couldn’t draw or draft well, I couldn’t take either.

“My drafting’s fine”, I said.

That’s the kind of behavior I mean. I sat in the office of someone I admired and feared, someone who was the gatekeeper for something I wanted, and I lied to his face.

His post, as I read it, is basically how few women have the audacity to lie their way into a job like he did. I see truth in that, though there are also cultural considerations he doesn’t address. But that’s not what I’m here to write about.

After reading his passage, it sparked this memory:

My First Internet Internship

Way back in 1996, when the World Wide Web was leaving academia for the commercial world, I lied my way into an Internet internship. It was with a small shop in Greenwich Village. The owner was a laid-back, pot-smoking guy who said the phrase, “Let’s touch base” way too much. His dream was to create the first online resource for all of Manhattan’s artists. Ambitious, for sure, but so were many of the Internet’s early visionaries. Sadly, he closed shop a few years later.

I first learned about the Web from my sophomore roommate. He showed me the Mosaic web browser and the few pages he could visit. “Isn’t this better than Gopher or Archie?” he asked. Indeed it was, though I didn’t explore it further until a year later.

I’m not sure what motivated me to apply to this internship. Was it because it was an art-related position and I had an interest in graphic design? Was it because it was close to my dorm? It didn’t pay. And I wasn’t exactly qualified.

“Do you know HTML?” asked the owner during my interview.

“Yes,” I lied.

He offered me the job the next day. Then I ran out and got a book on HTML.

The lead (and only other) technical guy on the staff turned out not to know HTML either (did he lie too?). So we both dove into the book and learned as much as we could. I still remember trying to figure out how to build an HTML table. Before it became a widespread practice, the other technical guy said, “How about we place different images into each table cell, so it forms a big, single picture, except that you can click on certain parts of that picture as links?” I didn’t realize it back then, but I was building a layout with a table.

From this experience, I built my first homepage with increasingly complexity. In between graphic design assignments, I would try to construct complex layouts and build them. Yea, I’m a geek. Fortunately, my geekhood paid off as I turned this experience into a career.

And that’s how I had the audacity to lie my way into an Internet internship and jumpstart my career on the Web.

P.S. I don’t believe you should ever outright lie for your career. I knew some HTML before I started that internship and was confident I could learn it quickly, so this incident is more of an aspiring exaggeration than an outright lie. Feel free to disagree though. Have you ever done something like this, for better or worse?

Photo by: Collin Anderson

Biz Idea: Social Media Market Research App

Classic OPTE Project Map of the Internet 2005 Want to see a list of links that will boggle your eyes? Last week, I listed a number of online services that could be used to perform market research. After seeing that list, I wondered:

How about a single online app that helps you do all of that? A social media market research app. Here’s what I think such an app could offer.

The Dashboard

It could have a dashboard that provides a snapshot of your market, ideally updated in real-time. There could be search results from the blogosphere, forums, Facebook (Groups and Fan Pages), LinkedIn, Twitter, Flickr, YouTube, Yahoo! Answers (YHOO), and other social media sites. Perhaps this information could be displayed through different filters:

  • By relevance
  • By publication date as a stream of news
  • By publication date on a timeline
  • By type of source
  • By source
  • By discussion in a threaded format
  • By tag (more on this later)
  • etc.

Features

My previous post listed a number of services that searched social media sites, allowed you to post questions, displayed search trends, and offered a wealth of company information. I’ll discuss those features first.

Keyword-Based Search Results of Social Media Sites

All of this information could be obtained through APIs and RSS feeds, some from the sources directly, some from the search services I listed. There would have to be some research done to see how real-time updates could be handled, however. Push or pull? Do they ping us or do we have to constantly ping them?

Asking Questions and Retrieving Answers

A mechanism to post questions & messages on forums, mailing lists, and answer boards could be really helpful. It should also harvest any subsequent answers & replies. This would be a tricky technical problem to solve though. Automatically posting on forums and mailing lists could be seen as spam.

Displaying Trend Data

The trend data could be presented in a timeline similar to Google Trends (GOOG) and Dipity, with items such as news articles, company events, and social media posts aligned with it. There could also be filtering options to control what is displayed. I don’t believe any of the trend tracking services offers APIs, however, so this may require a custom technical solution.

Displaying Rich Company Information

Every time a company is mentioned, it could link to a detailed company page that fetches financial & stock data from Yahoo! Finance and places it alongside rich information from sites like LinkedIn, Jigsaw, Crunchbase, etc. In the case of the paid service Jigsaw, they won’t have any APIs. But perhaps a partnership could be brokered.

Additional Features

In addition to the four features above, there are other cool things this app could do. A neat feature could be a Google (GOOG) map with real-time updates, a la DailyBooth or HashParty’s reach map. Each time a new piece of content is published, it could appear right away.

Another could be related keywords, similar to those seen on search engine results pages. I wonder if any search engines offer up related keywords in their web services.

This could also be a really useful feature: How about the ability to tag, rank, and annotate any piece of content the app finds? This is how you could maintain order when deluged with content. Filtering options could include tagged items as well, like displaying only the events tagged with “positive news” or “negative news” on the timeline. Ranking a piece of content could be a way to prioritize its visibility and/or subjective relevance to your research. Perhaps items could be flagged so customer service or public relations representatives can respond right away. And it’s always helpful to take notes against important pieces of content.

Challenges

The technical challenges are tricky. They are not impossible, but it would take a sharp technical team to think through these issues, such as:

  • How do we fetch the appropriate data reliably and quickly?
  • How do we deal with content that requires authentication?
  • How do we post on mailing lists and forums without triggering spam filters?
  • How do we get, display, and/or build trend data?
  • How do we attach metadata to each piece of content we’ve fetched?
  • How do we display the updates in real-time?
  • How do we design an easy-to-use user interface that allows non-technical business owners to use this app?
  • etc.

I’m sure there are a lot of social media consultancies that offer market research services. But as competitors, service firms rarely hold up to self-service packages. In such situations, self service firms tend to focus on the high-end of a market and offer highly specialized & customized services at premium prices. Going for low-end customers puts their profit margins at risk. Meanwhile, self-service packages like this app can afford to focus on the low-end as a cost-effective solution for them, while still maintaining fair profit margins. And who knows, maybe social media consultancies could become customers of this app.

There might even be such an app in existence already, though I haven’t heard of one. If you have, please let me know.

What do you think?

Photo by: curiouslee

Three Words of Wisdom

Oops, almost missed the memetrain on this one. Here’s an oldie but a goodie: Dharmesh Shah’s Startup Triplets, with a few from Guy Kawasaki.

These are basically three-word phrases for entrepreneurs. A ton of great ones have already been voiced. Here are mine:

I hope Shah doesn’t mind my using his awesome tweet link idea. Internet memes are fun!

Do Your Homework Whenever Meeting Someone New

Admit it, you’ve Googled someone before. Maybe it was someone you were dating. Maybe it was someone you had a crush on.

But how about when you have a sales meeting and are about to meet a new prospective client?

If you are an experienced salesperson, I’m probably preaching to the choir. For those like me who are in the consulting & services business and relatively new to the sales role, I have this to say:

Do your homework whenever you meet someone new.

This applies all around the sales cycle. From following up on leads to meeting other stakeholders to getting their team introduced with yours. Throughout this process, you are likely to meet several different people (or one person fulfilling all of these roles):

  • Primary stakeholder – the person with the budget
  • Influencers – other stakeholders who have a say in this decision
  • Project manager – the person who coordinates the work between your client and your team, also often the main point of contact
  • Workers – employees from your client’s team with whom your team will have to interact

Do your homework on each of them. For a service organization, all the members of your client’s team are important and critical to your success.

Why?

The goal isn’t to stalk the person. It’s to find meaningful connections. If the person likes the San Francisco Giants, and hey, so do you, then bring it up. If you’re not a fan, then keep your mouth shut. Don’t be insincere with these connections. Use them only if they honestly exist. Otherwise, you might find yourself in a TV sitcom where you’re trying to lie and squirm your way out of a totally alien discussion. And all without a laugh track.

If there are no connections, consider identifying a key achievement that person has made and offering congratulations. Perhaps the person started a company that launched a successful product in the past. Perhaps the person wrote a book or article you’ve read. Again, don’t be overtly insincere, though a little flattery can get you a long way.

It also helps to understand the person’s background. If he/she comes from a technical background, then you can tailor your sales pitch to a more technical audience. If he/she comes from a marketing background, then emphasize potential branding and identity benefits. Use key terminology from their background.

So far, I haven’t had a case where a person has been offended or frightened by this research. In fact, many seem to be flattered by it, even expect it. Some don’t care though; they’re more interested in the deal and how it can help them.

All of this assumes you’ve already done your homework with the company, their department, and their needs. Don’t even bother researching the people if you haven’t researched their business.

Ultimately, you want to form a connection with these stakeholders. If they feel they can relate to you on a personal level, and they feel you can sincerely understand them on a professional & personal level, then they are more likely to sign a contract with you.

How?

Here’s what I do:

  1. Google (GOOG) – I start with a good, old-fashioned Google search. This usually gives me most of the information I need, such as links to a blog, Twitter account, resume, etc.

    I always start with the blog, if one exists. This gives me a good overview of the person and his/her personality & interests. Does the person have a sarcastic sense of humor? A dry wit? Does the person have any hobbies or interests with which I can relate? Has this person done anything notable that I want to call out?

  2. LinkedIn.com – If the previous search doesn’t turn up a LinkedIn profile, then I perform one specifically on this site. Most people in my industry have a LinkedIn account.

    This gives me an overview of the person’s education and career path, which tells me the language he/she speaks (technical, marketing, design, financial, etc) and how I should tailor my sales pitch.

  3. Others – I know some salespeople go further and check out Facebook, MySpace, and other similar sources. Personally, I don’t. If you aren’t a member of that person’s Facebook network, then you won’t be able to see deeper details. Also, the interests and photos included on Facebook don’t help as much as a blog or personal website. It’s tough to form a connection on a favorite TV show, especially if you don’t know how much they like it, or if their profile has been updated recently. My experience, anyways; some still do this research all the time. And practically no one in my industry uses MySpace (that I know of).

Once you have this information, share it with your team. Help them to understand the client better. This can strengthen the relationship on both sides.

There will be a few cases where such web research doesn’t help because the person keeps a private offline life. That’s fine. That’s where you’ll need to muster up your interpersonal skills and form a connection the old fashioned way. These tips just offer an extra advantage. If the information is out there, why not use it, right?

Photo by: fazen