Category: Entrepreneurship


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


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!


Got a Good Business Book Recommendation?

Categories: Entrepreneurship

And I thought I read a lot. I’ve got nothing on this guy. In 2009, Tim Young read 146 books. Damn. I gotta beat him in 2010.

He also kindly suggested five books for entrepreneurs:

  1. Your Brain at Work: Strategies for Overcoming Distraction, Regaining Focus, and Working Smarter All Day Long

    This book sounds particularly useful. “Although most founders focus on their cash burn rate,” write Tim, “very few focus on the burn rate of their daily time.” Too true, too true.

  2. Beautiful Data: The Stories Behind Elegant Data Solutions

    Sounds like a nice, geeky read. Awesome.

  3. Performance at the Limit: Business Lessons from Formula 1 Motor Racing

    I’m not a big Formula 1 fan, but it could be an interesting read.

  4. Presenting to Win: The Art of Telling Your Story, Updated and Expanded Edition

    I’ll definitely need this book.

  5. The Inner Game of Tennis: The Classic Guide to the Mental Side of Peak Performance

    Oh, that reminds me: I keep meaning to play some tennis. And golf. Hurray for bougie sports.

The Knack: How Street-Smart Entrepreneurs Learn to Handle Whatever Comes Up One of my personal favorites in 2009 is The Knack: How Street-Smart Entrepreneurs Learn to Handle Whatever Comes Up by Norm Brodsky and Bo Burlingham. Brodsky is a veteran entrepreneur and author of the “Street Smarts” column in Inc. Magazine. Burlingham is an author and editor-at-large for Inc. Magazine.

The Knack is a gritty, no-nonsense book for entrepreneurs. From having hands-on experience with your company’s financials (to the point of going through your books with paper and pencil) to understanding root causes and not just symptoms, some of this material may be familiar, but all of it is practical. Reading this book felt like sitting down with a battle-worn business owner with a gravely voice and sharp tongue from Brooklyn who told it like it is. I would recommend this book to all entrepreneurs.

Do you have any good business books to recommend? I gotta beat 146 books this year!

Props to: Eric Rodriguez


How to Find a Designer or Developer Co-Founder Online

Are you an aspiring entrepreneur? Have a great Internet or technology business idea? Lack the ability to come up with a great UI design? Need a way to build out your idea? Sounds like you may need a designer or developer co-founder.

So how can you find one? Your own network is the best source. So are the social networks of your social network. But if you’ve already exhausted those avenues and don’t mind a cold connection (where you are connecting with a stranger), here are some other sources:


This is perhaps a no-brainer nowadays. Here’s a success story: the founders of MyBlogLog met through LinkedIn before they were purchased by Yahoo! (YHOO) for $10 million. Not bad, eh?

Build It With Me

This new service aims to connect designers, developers, and entrepreneurs interested in building an application of some kind, be it web, Windows desktop, Mac desktop, iPhone, Android, or some other mobile platform. It is the brainchild of Drew Wilson and despite being only a little more than a week old, is already sporting a fair number of designer and developer listings.


I hesitated on listing this site. It also aims to link up designers, developers, writers, and entrepreneurs, offering an option to work together in a long-term partnership. However, most of the listings cater towards freelance jobs as opposed to founder opportunities. It’s a potential source to check out, though I’m not confident it would be a good source for co-founders right now.

UPDATED 1/21/2010: Just added this one to the list.

Founder Dating

This is an event-based service that pairs up entrepreneurs interested in meeting co-founders. So far, they hold sessions in San Francisco, CA and Seattle, WA, but I’m sure they’ll do more as their service grows. According to their FAQ, they aim for a diverse mix of backgrounds & experience. Since it’s generally more effective to meet with partners in person, this sounds like a great idea.

Do you know of any other good online sources for co-founders?


On Failure

And Down She Goes!

“If we’re not failing at something on a regular basis, we’re just not trying hard enough.”
- Stephen Kaufer

As an entrepreneur, failure is a certainty, success is not.

It’s a fact that more small businesses fail than succeed. The exact percentage of failures to successes changes depending on who you ask, but that’s the general trend.

So as an entrepreneur, you need to be comfortable with failure. You need to embrace it. Plan for it. And when it happens, learn from it and move on.

If you want to be truly innovative, you’ll have to be especially comfortable with failure. Innovation means pushing the boundaries and doing something daring, something most people are going to call you crazy for doing. And chances are, most of the things you’ll do will be crazy. They’ll fail wonderfully in a ball of fire.

In other words, to be an entrepreneur (and to be innovative), you need to fail many more times than you’ll succeed.

Those who aren’t able to handle failure are better suited for a less risky lifestyle – though I’d argue that working for someone else isn’t less risky in actuality, it’s just less taxing mentally and less ambiguous.

We’re all wired to be risk averse to a certain extent. It hurts more to lose $100 than to gain $100, for instance. But it’s possible to flip that around when you’re an entrepreneur.

Failing sucks. Don’t get me wrong. There’s always a bit of a sting when something you’ve been pouring your heart & soul into fails. But the trick is to rebound quickly, assess why you failed rationally, and jump into your next plan eagerly.

The assessment part is important. This is where you learn from your mistakes. You can read all you want, attend all the conferences you can afford, and talk to all the advisors you can, but experience will still be your best teacher. Of course, you can decrease your failure rate a bit if you arm yourself with good information. However, when it comes time to make a quick & decisive decision, that’s where your experiences weighs heavily.

So you still want to be an entrepreneur? Go out there and fail. Then fail again. Then pick yourself up and with you’ve learned, go create a kick ass company.


Pyramid Scheme Scamming in Bookstores

It almost happened again.

“Good evening,” the gentleman in the hat said.

“Evening,” I muttered with nary a glance in his direction.

“You have your own business?” he asked.

“Nah. Just looking for a gift for a friend,” I replied. Then I walked out of the business book section.

Years ago, a seemingly nice guy struck up a conversation with me while I was browsing through the business book section. Not wanting to be inhospitable, and always eager to expand my business network, I chatted with him about my dreams of entrepreneurship.

I did occasional freelance web development work back then. He said he had his own business and needed a new website. So I gave him my card.

He set up a meeting to discuss his website. When we met a week later, he pitched me a dizzying business model of soliciting friends and helping them set up their own business too, just like he was going to help me do. No talk of a new website at all.

As soon as he sketched out a bunch of boxes on a napkin that vaguely resembled a pyramid, I stopped the conversation. “Look, I know what you’re trying to pitch me. You’re trying to pitch me a pyramid scheme.”

He looked at me incredulously. “What?! This is not a pyramid scheme!”

I thanked him for the coffee, got up, and walked out. As I left, I noticed a gentleman in a suit sitting a few tables over. He glanced at me, then turned away immediately. It was too late. I recognized him. He had been in the bookstore when I first met the pyramid scheme guy. He was even wearing a suit back then, which was why I recognized him. (A guy wearing a suit in Silicon Valley sticks out like a sore thumb, lemme just tell ya.) Mr. Suit had been standing behind me while I was talking to Mr. Pyramid Scheme at that bookstore.

This time around, I glanced around the business book section as I walked out. There was an older gentleman standing near the gentleman in the hat.

A case of a master and an apprentice? Do they always work in pairs? Or just a mere coincidence?

It’s entirely possible I am wrong about the gentleman in the hat. He could have been just a friendly guy wanting to chat.

In my experience, however, only salespeople attempt cold leads like that. It’s like cold calling, except in a bookstore. In fact, it’s pretty smart of them to prey on readers perusing business books. They’re targeting people with a potential entrepreneurial streak. And with the lure of easy money being strong – especially in an economy like this – I wonder how many bites they get.

This has even happened to me on the plane. That’s another smart spot for them to target. They have a captive audience. On some flights, the chances of its passengers being there for business is high. So I wouldn’t be surprised if it’s another target zone.

I could be wrong, but my gut sensed something fishy at the bookstore that night. If I lost out on a potential legitimate business connection, oh well. I’d rather make my connections through other means than to waste my time being sold another pyramid scheme. Life is too short to waste time like this.

Has this ever happened to you?

Photo by: goose3five


Reading True North: Your Story Exercise

What’s your story? That is the question covered by the first chapter of True North: Discover Your Authentic Leadership. I’m covering each of the exercises that follow the chapters of this book.

The True North exercises:

  • Introduction Exercise
  • Chapter 1: Your Story Exercise
  • Chapter 2: Losing Your Way Exercise
  • Chapter 3: Your Greatest Crucible Exercise
  • Chapter 4: Knowing Your Authentic Self Exercise
  • Chapter 5: Practicing Your Values and Principles Exercise
  • Chapter 6: Your Motivations and Motivated Capabilities Exercise
  • Chapter 7: Building Your Support Team Exercise
  • Chapter 8: The Integrated Leader Exercise
  • Chapter 9: The Purpose of My Leadership Exercise
  • Chapter 10: Empowering Other Leaders Exercise
  • Chapter 11: Honing Your Leadership Effectiveness Exercise

Discover Your Leadership in Your Life Story

During your early years, which people had the greatest impact on you?

My parents and teachers had the greatest impact on me. Both of my parents are in leadership positions, though each varies significantly in leadership style. Their range has taught me to consider a range of techniques for any given situation.

A handful of teachers also made an impression, such as my fifth-grade teacher and her weekly Poor Richard’s Almanac quotes (“An ounce of prevention is worth a pound of cure”, “A penny saved is a penny earned”, “In this world nothing can be said to be certain, except death and taxes”, etc). I love quotes, those little nuggets of wisdom. Perhaps that love originated from fifth-grade.

Starting with your earliest memories, which experiences marked turning points in his life?

There were many. First, I was a quiet, introverted kid. Then a series of fortunate events evolved me into, surprisingly, an extrovert. The change has been so striking that I sometimes wonder if my true nature is to be an extrovert and my childhood environment nudged me into being an introvert. (Not that there’s anything wrong with being an introvert. Extroversion and introversion are merely where you get your energy and place your attention – from other people or from yourself.)

Once that foundation was set, my first true taste of leadership came in college. In my junior year, I became the public relations officer of a student-run community service organization. Then its president in my senior year. Leading a team of intelligent type-A officers and student volunteers like myself was a remarkable experience. I had to learn how to deal with my weaknesses, hone my strengths, delegate, communicate effectively, motivate officers and volunteers already swamped with school work, coordinate social events, and grow the organization.

The next turning point was becoming an engineering manager at Yahoo! (YHOO). At the peak of this role, I managed a small organization of 22 developers and first-line managers. The experience allowed me to hone a set of management techniques & principles that have become my management style.

The latest turning point has been launching WebMocha, where my leadership role evolved from leading teams to leading a company with business partners. In this role, I was fortunate to find partners who complemented my strengths and weaknesses, and I theirs. A whole new set of leadership behaviors had to be refined here, such as managing workers, dealing with client projects, winning the hearts and minds of prospective clients, managing finances, working towards profitability, etc.

There was also another significant turning point – a nearly fatal accident while skydiving. That profound experience taught me to appreciate life and view it graciously. It’s also made me realize the importance of being myself, of being authentic. Because when I’m on my death bed, what do I want to be proud of: having lived my life as someone else or having lived my life as myself?

In which experiences did you find the greatest inspiration and passion for leadership?

Any instance where someone in my team achieved greatness, success, recognition, or reached his/her own goals has been inspirational. I was fortunate enough to experience this over and over again while at Yahoo! The high I received was way better than any drug, lemme tell ya.

Looking at patterns from your early life story, what people, events and experiences have had the greatest impact on you and your life?

These questions are a bit redundant, huh? My parents and teachers had a significant impact on me. As did the events I described in the last two questions.

Can you identify instances where you were dissatisfied with your leadership or received constructive feedback from others about it?

There are a few poignant moments at Yahoo! that I regret. Having 22 members meant being responsible for evaluating the performance of many direct reports. That was more than I could handle. Arguably, it’s more than anyone could handle. As a result, some of the members I didn’t know as well didn’t get fair & accurate performance evaluations.

In one case, I had a developer with great potential, provided he had the proper guidance. Unfortunately, there were too many other priorities at the time. When review time came, he was dissatisfied with his evaluation and didn’t feel like he was working to the best of his capabilities – which was absolutely true. He ended up leaving my team and becoming a senior developer on another team. Thankfully, he was able to reach his true potential there, unlike in my team, where I feel like I failed him.

Has there been an instance in your life where you felt like a victim?

Nope. I’ve always felt that I have control over my life. The bad situations I’ve gotten into are my fault, and it’s my fault if I don’t learn from them.

Do the failures or disappointments you experienced earlier in your life constrain you, even today, or have you been able to reframe them as learning experiences?

They are definitely learning experiences. Fantastic learning experiences too. While some past experiences were very unpleasant, they’ve made me who I am today and I’m happy with who I am today. After all, “we remember some of what we are told, a little more of what we read, and almost all of what we experience.

The Journey to Authentic Leadership

Do you currently view your life and leadership as a destination to a certain point or as a journey in which you seek to maximize your learning and experiences?

Life is always a journey. If you reach a goal or destination, then it’s time to set another goal and return to the journey.

The journey can be made much easier if you learn from previous mistakes. Otherwise, you’re doomed to repeat them. I don’t know about you, but I don’t like repeating dumb mistakes over and over again.

What are the most significant leadership experiences you have had to date and what did you learn from them?

The major life turning points I wrote about above are also some of the most significant leadership experiences I’ve had so far. From becoming the president of a student-run community service organization in college, to an engineering manager at Yahoo!, then to the principal of WebMocha, I’ve learned a lot from these wonderful experiences, which I’ve written above too. Cheers to redundant questions.

What experiences do you need to develop your leadership to take it to the next level?

The next step in my leadership education is becoming a successful entrepreneur. Fortunately, I’m already on this path with WebMocha.

If you are just entering a new phase, have you assessed the goals and experiences you would like to have during the phase?

Yes. My goals are sustainable profitability and growth from WebMocha. The experiences I’m going to learn from this journey will be invaluable.

Do you think you need to make any adjustments to your personal and leadership development as a result? If so, what are they?

I will definitely need to make adjustments. My leadership experience has been mainly people-based, as opposed to business-based. While managing a business shares many of the qualities needed to manage people and teams, there are also notable differences too. This is what I will need to learn.

This will include greater reliability on intelligence business managers & leaders in my social network for wisdom & advice. I am fortunate to have a good and varied network. As my schedule eases up, I look forward to meeting with each of them regularly.

How can you take your previous experiences and apply them more optimally to your leadership now?

The failures I’ve had will be an important lesson in the future. I know that being an entrepreneur is difficult and fraught with challenges. Failure is a certainy. Success isn’t.

How would you answer these questions?

The True North exercises:

  • Introduction Exercise
  • Chapter 1: Your Story Exercise
  • Chapter 2: Losing Your Way Exercise
  • Chapter 3: Your Greatest Crucible Exercise
  • Chapter 4: Knowing Your Authentic Self Exercise
  • Chapter 5: Practicing Your Values and Principles Exercise
  • Chapter 6: Your Motivations and Motivated Capabilities Exercise
  • Chapter 7: Building Your Support Team Exercise
  • Chapter 8: The Integrated Leader Exercise
  • Chapter 9: The Purpose of My Leadership Exercise
  • Chapter 10: Empowering Other Leaders Exercise
  • Chapter 11: Honing Your Leadership Effectiveness Exercise


Passion for Your Business

So true:

Whatever your company does, you need to believe in your gut that it’s the most interesting, exciting, worthwhile enterprise you could be engaged in at that moment, or you’re going to have a hard time convincing anyone else – employees, customers, investors, whoever – to make commitments to you.

That’s a quote from Norm Brodsky’s new book The Knack: How Street-Smart Entrepreneurs Learn to Handle Whatever Comes Up.

You gotta have passion for your business. Otherwise, why put up with all the bullshit if you don’t really care about what you’re doing? If you’re in it just for the money, you will be beaten by a competitor who really cares. But if you do it because you love doing it, your passion & enthusiasm will shine through.