Jason Baptiste

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Why Every Entrepreneur Should Write and 9 Tips To Get Started

By Jason Baptiste on September 27, 2010

"The best part of blogging is the people you will meet"- Hugh MacLeod repeating wisdom from Loic Lemeur to me at the Big Pink at 2 am in South Beach after the Future of Web Apps 2008.

If you asked me to tell you a list of three of the best decisions in my life, I can certainly tell you that regularly writing is one of them. It's the reason I'm an author here at OnStartups, made many new friends, had interesting opportunities cross my radar, and most importantly had the chance to share knowledge that has helped other entrepreneurs.onstartups writing

Why You Should Write

You Will Meet Other Smart People

Writing has allowed me to meet a slew of smart people. Some of these people are now virtual acquaintances and some are very close friends on a personal and professional level. Each article that you publish is a synthesized thought process that may click with other entrepreneurs instantly. Have you ever had a feeling when reading an article that "Wow, they are thinking exactly what I'm thinking"? By writing, you are likely to encounter a handful of people that experience the same thing. Occasionally one of those people will reach out to you via email or bump into you at an event. You might make a new acquaintance, a new co-founder for the future, potential investor, hire,etc. At the end of the day, being an entrepreneur is about finding other smart (hopefully smarter) people to collaborate with and writing frequently helps make this happen.

Example: I ended up becoming a writer here at OnStartups due to my own writing. A year ago, I put out an article called "Disruption and My Next Startup". This is how I first met David Skok from Matrix Partners. David later introduced me to Dharmesh, who has become a good friend since moving to Boston. After talking about all things entrepreneurial, we realized we both had the same altruistic goals with writing: to meet other smart people and help share the lessons we've learned. Small piece of trivia: OnStartups was started in 2005 on Dharmesh's birthday. I joined OnStartups on my birthday this year (September 8th).

Your Experiences Will Provide Insightful Knowledge To Other Entrepreneurs

Every entrepreneur has been through many of the same yet different experiences. We find co-founders, we all work at building a product/service, we all try to get customers, etc. Even though we're doing the same thing at a high-level, we all have different experiences. We may have found great co-founders, built a great product, but fail to acquire customers. Each entrepreneur+startup mix is a unique permutation that varies from the rest of the world, hence providing a snowflake of experience. Through writing you can not only help share your successes, but also the pitfalls that lead to your failures. There's no magic bullet to entrepreneurship, but the wealth of writing from experienced entrepreneurs out there such as Paul Graham, Dharmesh here at OnStartups, Jason Fried and Joel Spolsky have prevented young entrepreneurs from making mistakes that they might have made otherwise. Open source technology has helped entrepreneurs get started immediately with no capital while significantly reducing risk (you would have to raise a large amount of capital to launch anything with lines of code behind it a decade ago). I believe open source knowledge on entrepreneurship can help do the same when it comes to the business side of things. Getting as many entrepreneurs writing + sharing their insight is the very first start of this.

You Will Establish Domain Expertise

Every person is an expert in their own right at something. It might be user interface design, coding, leadership, raising money, investing, etc. By writing you get a chance to establish that domain expertise by sharing it with the world. Don't worry about people stealing your secret sauce either. Famous chefs share their secrets and hints all the time without fear that it will cause their demise.

It Helps Build Dedication

Writing on a regular schedule takes a lot of discipline, just like going to the gym or practicing a new martial art. Nothing happens overnight, including building an audience and becoming a good writer. Like most things in life, writing takes time and strong dedication. Unwavering dedication is a valuable skill in startups that many seem to forget. If you keep yourself dedicated to writing on a consistent schedule, those important values will carry over to other facets of life including startups.

Your Communication Skills Will Get Exponentially Better

It takes a lot of work to become a great communicator as an entrepreneur. You have to break down complex problems, very technical solutions, and intricate details into soundbites that flow logically. By writing, you develop the ability to communicate more clearly to an audience of many, by providing a logical argument with a unique angle to your position. In some ways, you've been learning this skill your entire life through schooling, but writing as an entrepreneur in a public medium is something completely different. Through schooling you write for an audience of 1-2 people. Those people will usually judge you based not upon the content, but whether you agreed with their point of view. Writing as an entrepreneur in a public medium puts you in the spotlight of tens of thousands to millions of unique readers. If your writing isn't cohesive, there are many that can call you out. I had some rough professors throughout my undergrad years, but no one will call you out like internet commenters, many of which may be trolls. By the third article, you start to subconsciously think "Is this cohesive/does it make sense?" as a gut reaction when writing in order to avoid negative feedback.

You Will Build An Audience That Will Give You Candid Feedback

If you're really lucky, you will start to build an audience that isn't full of trolls, but that consists of those that are genuine and honest. They may give you negative feedback, but it will be candid+honest. Don't just look at the number of re-tweets on an article, look at the articles that get the audience to participate. You will eventually find a groove of what your audience enjoys and what they consider good writing. Try to reply to every comment as well, even if it is a simple "Thank you."

It Is A Rapid Accelerator Of Serendipity

Startups are certainly impacted by luck, but I believe they are impacted just as much by serendipity. You never know who knows who or who you may run into at an event. By putting yourself out there and making yourself open to meeting as many people as possible, serendipity is much more likely to happen. Once you have even a minor audience, you are now likely to experience the effects of serendipity. One article might reach 500 or 50,000 people in a short span of time. Remember that we live in a world where content/information travels faster than ever before. Out of those 50,000 people, you never know who might be reading, who might reach out to you, or who might leave a comment. I can tell you this: The majority of good things that have happened to me in business can be traced back to my writing


9 Tips How To Get Started


Many think that writing is as simple as registering for a Wordpress/Tumblr/Posterous account and all of a sudden they're the next Seth Godin. Just like anything in life, it takes time, practice, and finding the formula that works well for you. I started writing almost 2 years ago, but didn't get into it seriously until approximately 3-4 months ago. Here's a list of some of the things that I've learned along the way that will hopefully be useful food for thought.

Keep It Simple And Worry About The Aesthetics Later On

Sign-up for Posterous, Tumblr, or Wordpress. If you really want to customize things later on, host your own Wordpress install. Find a good, simple/basic theme, set up some basic settings + SEO, and get to the races with writing. Try to use your own name as the domain name. If you have a popular first+last name combo and can't own your exact name, try to get something similar. Last, but not least, try to have a picture of yourself somewhere on the site. It's good to put a face to your writing and this will help people identify with you when meeting up in person. Besides the simple stuff above, just start writing. Insightful content is king and that's where you should be focusing your efforts.

Define A Specific Audience To Write To

As you'll see in this link , which is also listed below, John Gruber writes for a specific audience- himself. You can further narrow down John Gruber as an apple fanboy who is geeky and educated. When writing I try to do the same thing. I write every article as if I owned a time machine and could mail myself letters five years ago when I was first getting started. To be honest, I still don't really know anything, but back then I knew absolutely nothing at all. Everytime I'm in the midst of an article, before completing it, I ask myself: "Would this have been useful to me five years ago?" If I say "No", then I stop writing, and possibly come back to it later to re-evaluate things if a new approach to the article comes up. Find your audience, that one exact ideal person, and write to them every time.

Set A Regular Routine

I get one article out every week and try to stay to that schedule regardless of what else is going on. I put it in line with working out everyday. It either gets done or not done. Sure the world won't end, if you miss a week, but that's not the point. It's about building dedication and putting something fresh out. I do all my writing on Sundays, edit throughout the week, and then release the articles when I have time to deal with comments/promote the article. The downside to this is writer's block or feeling like you have to write for the sake of just writing. I stray away from this by breaking things up into chunks and sections.

Don't Force It

Whatever you do: Do Not Force An Article. Set your schedule loose enough that you can get something out the door on time, but don't wait until the last second. Spend a lot of time thinking about your articles before hand. Most of my articles are formed before I write a single word in textmate. While I run, spend time on the T, and shower I usually think through the logic of articles. By doing this, you're not looking at writing an article like it's a high-school essay. It will flow naturally and won't be forced.

Initially Share With Close Entrepreneurial Friends

In the beginning there is a good chance you won't have a large readership, but that's okay. Send the article to close friends in the entrepreneurial community and just ask for some basic feedback. If they like it, ask them if they can share it with others. Also start sharing with other communities that you may be a part of, such as the one here at OnStartups or Hacker News.

Watch Your Analytics

Check to see where most of your traffic is coming from and double down on those avenues. Also pay attention to direct traffic sources. This means that people are either emailing your article around, sharing via instant messenger, or actually going to the URL directly. Also look at which articles ultimately become most popular with readers. Over time you will start to understand what your audience likes (ie- entrepreneurial advice, tech insights, interviews with other entrepreneurs, current event analysis, etc.)

Have a main topic + supporting points to avoid rambling

Each and every one of my articles has the same general format. Position/Argument usually found in the title, opening paragraph, supporting H2 tags, and then a closing paragraph. It might get repetitive over time, but it allows me to form arguments clearly + segment things out well enough into chunks.

No linkbait, just "thoughtbait"

I don't get into flamewars or write linkbait. It may work very well for some entrepreneurs to get recognition and increase pageviews, but it shouldn't be about that. It should be about sharing your knowledge and hopefully educating your reader. I like to write what I call "thoughtbait". A reader should come away with actionable knowledge that makes them think "I need to try this" or "I'm pumped up to get something done". Readers should also be sharing the link to help others gain the same knowledge as well.

Make Yourself Easy To Reach

Last , but not least, make yourself approachable and very easy to reach. Put your email addresss up, Twitter account up, and possibly your phone number. Robert Scoble still has the same phone number from when he first got started, and will still pick up/respond to texts. It may seem like a burden, but it's not. If you want to meet as many smart people as possible, you need to make yourself approachable and easy to be contacted. I get multiple emails a week from readers or people saying "thank you" re: my articles. This is one of the most rewarding things I've ever experienced. Great part is this: You can start experiencing it too. The goal of this article isn't just to inform and educate, but to hopefully start a movement to get as many entrepreneurs as possible to start writing. Whether you are a novice or a seasoned startup veteran, writing will not only benefit you, but it will benefit those who need your knowledge. If you start writing or already write insightful pieces about your experiences, please drop me an email:
j@jasonlbaptiste.com . I'm certainly going to start compiling the list as it grows and will share it. One of my first additions was my buddy Wayne , who founded i2hub. 


Here are some other useful resources on the topic:

Spencer Fry- http://spencerfry.com/on-writing

Marco Arment- http://www.marco.org/691438863

Interview With John Gruber On Writing- http://shawnblanc.net/2008/02/interview-john-gruber

So, are you convinced you should be writing -- or writing more?  If you're convinced, what will it take to get you to do it?  If you've already been writing, have you found it to be useful?  Would love to hear your stories and experiences. 

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Lessons Learned From StartupBootcamp 2010

By Jason Baptiste on September 14, 2010


This is the first article from Jason L. Baptiste, a new writer at OnStartups and local Boston entrepreneur. You should follow him on Twitter (@jasonlbaptiste) or say hi via email.  Expect to hear a lot more from him in the future.  He's awesome. -Dharmesh


On Saturday, MIT hosted Startup Bootcamp to provide a diverse group of lessons to hopeful founders and those teetering on the edge of jumping into a startup. The tagline for the event was actually "Starting a company is easier than you think." The videos will be online soon as well if you want to relive the experience. I thought it would be useful to sum up the important lessons from each talk instead of doing a direct play by play. mit logo onstartups

You can also check out more coverage at:

1) Startup Bootcamp Take Aways

2) Why I'm Going To Get A Dog, Lose My Ego, And Just F'Ing Do It

Chris Wanstrath (GitHub) - Your Customers Are Your Best Sales Team

The story behind GitHub and how the team got there always amazes me. Github started out as a side project and morphed into a monster primarily by using their customers as a strong distribution+sales channel.

Let Your Product Help Customers Shine

  If your product helps customers shine, they will attach it to their work and give you increased visibility. GitHub helps developers show their code off and have a better experience. Through this, hackers/founders share the product with others.

Build For More People

  Build your product to leverage Metcalfe's Law (THE Metcalfe of Metcalfe's law also spoke btw), and grow in strength when more people are added to the system. The key to Metcalfe's law is the ability to GROW UTILITY when more people are added. Make sure you aren't DECREASING utility.

Spend Face To Face Time With Your Customers

  It's always good to spend face to face time with your customers. Sure tweets and emails get the job done, but that's not personal enough. Go spend time with your customers. Body language and that open level of communication make for an understanding that can't be had through any other medium.

Mick Mountz - Seek Funding Through Your Customers (Kiva Systems)

We funded my first startup through the product stages via an actual customer. That's why I love the B2B space as a large market will often let you fund the company through early customers that are begging for your product.

Funding Through Customers Should Be Priority One

Funding through larger channels such as angel or VCs can come later on, but they are not a given. Funding through customers? That's called revenue and is the lifeblood of any company. By discipling yourself to raise money from your customers, you put yourself in a position of power from early on.

Customers Provide Benefits Outside of "Revenue"

Customers pay you, but they will also provide you other valuable information. They will tell you what works and what does not work. Don't over-engineer the first concept. Get to customers fast and let them give you feedback. That hour of feedback in the early days will be worth more than their LTV in dollars.

Ayr Muir (Clover Food Lab) - Know Thy Customer

I'm a customer development junkie. Listening to your customer and getting inside their head can give you insights to solutions you would have never seen before. 

Get Inside Their Head

Ayr started working at a Burger King to fully understand the food business. I think this is the entrepreneurial version of method acting. Don't be afraid to get your hands dirty. It lets you truly understand their pain and understand what product they want.

Experiment, Fail, Learn, Repeat.

Ayr suggests that entrepreneurs should experiment on the cheap and be fast while doing it. Many things will fail fast and that's a okay. From there, the goal should be to learn as much as possible. Sometimes it's just as important to know what NOT to do rather than what to do.

George Bell (Excite/General Catalyst) - Build For The Long Haul

George's talk works really well in conjunction with Stephen Wolfram's. George is a VC at General Catalyst now along with being the former CEO of Excite.

Culture Helps You Endure

Building a great culture for the long term will help you endure for the long term as a startup. A strong culture makes an enjoyable environment that people grow attached to and will not want to leave behind.

Listen. Listen. Listen

Listen to your employees and build around them. You may have your own vision as a founder, but each company may have 3-4 founders maximum. Beyond those 3-4 individuals you need to build a company for hundreds and maybe even thousands time that. By listening to not only your employees, but the market you can position your company to endure time. Your original market will fade and listening can keep you prepared.

Bob Metcalfe (3Com/Polaris Ventures) - It's Not About You, It's About The Company

Bob is at Polaris Ventures now, but he is a legend by all standards. He invented Ethernet and founded 3COM. Not only is he a genius, but he is just someone that radiates love for the game. Even though I'm sure he gets praise all the time, the fact that he almost teared up at someone thanking him for ethernet says a lot.

Build A Synergistic Team of Geeks and Suits

We need each other and I'm glad a geek like Bob brought this forth to the crowd. As a geek, it's sometimes hard to realize you need someone with a good sales+marketing background. Without a good product, you have nothing to sell and without selling, your good product means nothing.

Sum Of The Parts Is Greater Than The Whole

It's about building a company with smart people that share the same vision as a whole. Bob has taken roles at 3Com from marketing to engineering. Don't lock yourself into one role and gain experiences so you can hire people smarter than you for those roles. Don't have an ego and don't think you're above a role.

Bill Clerico (WePay) - How To Endure

Startups are not for the weak at heart. Everyone tries to do attribute startup failure to business forces or some other error. I personally think the biggest reason for failure is due to the fact that it is just tough. Not everyone that tries to be a Navy Seal makes it through training. Not everyone that tries to be an entrepreneur makes it through until the end. Bill shared some good lessons on enduring as a startup founder.

Think About the Bigger Picture

Bill brought up the fact whether or not you would regret doing the startup 50 years in the future. Jeff Bezos says the same thing with his regret minimization framework. I also noticed an underlying desire to focus on creative things / quirks in order to forget about the abyss in front of your face.  For example, they have a company dog in order to keep them going every day.

Roll The Dice

They gambled their last dollars to make up for the rent they were $500 short on. They ended up making $600 and enjoying a good dinner too. Rolling the dice is risky and not always something you should do, but sometimes it's all you have. If you aren't about taking risk then the startup game probably isn't for you.

Product Changes The Game

Product changes absolutely everything. Until you have a product that users can play with and hopefully pay for, you are fighting a completely uphill battle. Don't worry about raising money or other things until you have a product that the market can play with, even if it is "ghetto".

James Lindenbaum (Heroku) - Be a Machete

Heroku is a beast of a company with a ton of users and a large number of paying customers as well. When looking at the live stat counter I think it caught James off guard as it increases so much everyday he didn't know what the exact number was. Very candid and very inspiring moment.

What is a machete?

A machete is a simple straight forward tool that allows you to accomplish and be many things while staying simple. The same could be achieved with a swiss army knife, but that's bloated and really 50 things crammed into one. A machete is really one thing that can serve AS 50 things. What can you discover from your product and through customer development?

Throwing Things Away

In order to be a machete, you have to be ultra lean and able to stay simple. In order to do this, you need to be able to throw things away that aren't necessary to your customers. Don't have too much emotional attachment to a product or feature.

Alexis Ohanian (Reddit/YCombinator) - The Time Is Now

This was by far my favorite talk of the day. Alexis has seen things from both sides of the table as a young 20 something entrepreneur and now as an angel investor via Das Kapital Capital / YCombinator.

Angels Are Everywhere

The recent influx of super angels and costs to get a startup off the ground have made capital widely available to smart entrepreneurs. With ideas costing a fraction of what they used to and more angels available, the number of startups in the wild should be able to increase dramatically. I suggest raising revenue over raising capital, but if it's needed, there is more of it at the early early stage level than ever before.

Live Cheap And Go Far

For the most part, the audience was filled with current college students and some recent graduates. Instead of taking super big salaries from traditional jobs like wall street, you should go start a startup. Now is the best time as the burden of responsibilities are just insanely low. Your standards are also low as well. The difference between ramen profitable for an out of school entrepreneur and an entrepreneur with a wife, mortgage, and 3 kids is vastly different.

Entrepreneurs Are Superheroes

This last point has motivated me a ton over the weekend. Alexis' last two slides referenced the fact that startups can save our country. I truly believe this is the case and in some ways entrepreneurs are like superheroes. We have a higher calling and civic duty that can help save the world. We can create new jobs, provide a rewarding life for our team members, and solve the problems of the real world. We also have a higher tolerance for pain than the normal human. You have to be able to have a high threshold as an entrepreneur, the same way Wolverine has regenerative powers. Get up, get out, and create a company. Now is the time and the world needs you.

Stephen Wolfram (Wolfram Research) - Control Your Destiny Without Funding

Many startups focus on raising capital and putting themselves on a timer to be primed for an exit of some sorts. Sadly, that exit often comes in the form of a small M&A acquisition instead of building a long term enduring company. Wolfram showed that it was possible to control your destiny and build a company that can last for decades.

It Starts With Something You Understand

Wolfram started Mathematica after having a deep understanding of the field and the need for its existence itself. When you create a startup that you want to see in the world, you grow a certain attachment to it. This attachment is akin to something a fanatical customer might feel. You're less likely to throw the company away on a "flip acquisition" due to your attachment and caring for the product with the hope that it won't go away.

Be Weary Of Managers That Are Hired

Wolfram has done a number of startups and some came before Wolfram Research. His biggest mistake was hiring managers that weren't in the same stage of life and/or on the same wavelength as him. This created a disconnect in product vision and his desire to stay with the company. Surround yourself with peers that you would want to spend time with for a long time.

You Can Do Cool Exploratory Things When You Own The Company

WolframAlpha may have never existed if Stephen Wolfram did not control the company himself. It is a big undertaking with huge capital and human resources being required. By controlling the company you will want to stay with the company for the long haul as the possibility of incubating and creating "startup-like" projects can be done.

Kevin Hale (Wufoo) - Awesome Customer Support Is Your Secret Weapon

If you haven't seen Kevin give a talk, then you're missing out. I originally saw Kevin give a talk at BarCamp Miami back in 2009. I made sure I was back from the break early not to miss his talk as I had a hunch it would focus on the overlooked, but very important aspect of customer service for startups.

Build As If You Had To Support It

Thinking about adding a radical new feature with crazy complexities and absolutely amazing effects? With those crazy new complexities and absolutely amazing effects will come an onslaught of customer service inquiries. Think about the customer support funnel and how that will be impacted by the features you are adding.

Measure Emotion

Measuring emotion is critical when asking a customer to fill out a support inquiry. Wufoo added a box that asks a customer to identify how they are feeling when submitting a support inquiry. They didn't think too many people would fill it out, but over 80% did. This was on par with how many people filled out what browser they were using.

Adding a Personal Touch Goes a Long Way

Wufoo team members still write thank you letters by hand to customers that have been with them for a short while. In a world where the expected customer service experience is usually something negative, a small personal touch can go a long long way. Surprise your customers with a personal touch. I'm aware Wufoo does this, but seeing it again always blow me away.

Ric Fulop (A123 Systems) - Focus On The People.

Ric is a hardware guy, which is often foreign territory for web app entrepreneurs like myself. He was previously the co-founder of A123 Systems. From day one you should be focused on the people involved with your startup.

Plant The Seed With 1-2 People

Every startup begins with 1-2 other people. Building that team at first is the key to the long-term DNA and product of your company. You're not doing this to be a small company for the long haul and you can scale up your organization later on.

Find Relevant Advisors

Hardware startups are especially difficult. How do you break into the hardware side of things or any other difficult territory where credibility is a must? Find advisors who have relevant domain expertise and credibility that you can borrow. Once you have that credibility, it can then be used to provide momentum to the business as a whole.

Focus On The Person Making The Investment

Money is the common denominator when raising capital. All investors have it and all dollars are green. What really matters is the person at the firm and their relevant domain expertise. I don't have any plans of doing a hardware startup, but if I did, Ric would be on my shortlist of people to approach. Your startup is solving a very specific problem and the investors on your side should be able to bring access to relevant domain knowledge and other people inside the sector. This is the true definition of "Value Add Investing"

David Cancel (Compete/Performable) - Data Provides A Reality Check.

David Cancel of Performable closed out the show with a useful, but well needed reality check for hopeful entrepreneurs. Too many times we come away amped from reading a press article about startup success or going to a conference with successful speakers. This energy can often make us forget to listen to reality itself and take a look at objective facts. When your energy is high, you often feel as if nothing else matters. Here are the key things that matter:

Business Plans and Demos Are Useless

BPlans and Demos are controlled environments with no customer interaction. They can't survive in the real world and will never work out there. No one cares about them and neither should you.

Evoke Emotion

You don't want to be stuck in the emotion and get hit with "that's interesting" from an investor. You want customers, investors, or any potential partner to be fired up with emotion.

Listen To The Data

Stop reading TechCrunch and listening to the end-game / feel good stories. What should really get you amped up is the data coming in from your customers. Have a company-wide dashboard, measure your analytics, and get to know your funnel. Want to test something? Listen to the data, not the praises or hatred from the press.

I hope the summaries give some motivation and insight into starting a company for hopeful entrepreneurs. As entrepreneurs we are lucky and very fortunate. Right here, right now is the best time in the history of civilization to start a company. More on that soon.

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