Lessons Learned From StartupBootcamp 2010

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Lessons Learned From StartupBootcamp 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.

Posted by Jason Baptiste on Tue, Sep 14, 2010


Jason, thanks for the crisp / great summary. I was mostly online; however had to miss some parts due to the video issues in the afternoon. Dharmesh's highlight tweets added to the experience. Hope to catch up and review again once the videos are up on the site. Thanks for the organizers.

posted on Tuesday, September 14, 2010 at 12:59 PM by Paddu Govindaraj

Great summary of the talks. Having a few understanding and paying customers are absolutely essential for product development while paying the bills. You know you have a good startup team when the founder/visionary can afford to get sucked into another project and the company continues to grow with minimal oversight. And, you are on the right track, when the talks like these sound like they are telling your story.

posted on Tuesday, September 14, 2010 at 1:27 PM by AJ Durrani

I took some pretty intense notes while sitting in the audience on Saturday and must say you did a good job recapping the best points from each speaker.  
One more thing I learned from Kevin Hale is to do the opposite of what everyone else is doing in the industry. HubSpot's a good example - Most marketing software companies would choose the IBM blue by default. You guys chose an outlandish orange and now when I see marketing software and orange, I think HubSpot.

posted on Tuesday, September 14, 2010 at 1:29 PM by Andy Cook

A lot of excellent information. This bit stood out:  
'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.' 
VERY good advice. I'm sure when I've digested the whole article further there will be many more insights I can use. 
Cheers - Steve 
Founder: Arten Science

posted on Tuesday, September 14, 2010 at 1:37 PM by Steve Cholerton

As a brand new start-up that launched our first B2B application for the real estate and mortgage industry just last month, we have been living most of the comments and advice above hour by hour. Thanks for summarizing. Now we know that all we need to do is follow the 31 simple steps above and we'll be on our way. :)

posted on Tuesday, September 14, 2010 at 1:38 PM by Michael Licamele

Thank you for the great insights. Lots of valuable takeaways. I agree with all the speakers. Starting a company is never for the faint of heart. It's like rock climbing without a rope. Every step is a calculated risk and one wrong move could spell disaster. But, the payoff--like making it to the top of the mountain-- can be exhilarating, indeed.

posted on Tuesday, September 14, 2010 at 1:40 PM by A Tan

Additional Take-Aways: 
- MBAs/Suits = Bad 
- Techies = Good 
Ironically, this wisdom comes to us from from a Non-Techie, a.k.a, a suit.  
Otherwise, the event was great and informative. Get Er Done!

posted on Tuesday, September 14, 2010 at 2:14 PM by Josh

Great post! Thanks for sharing this valuable intel...

posted on Tuesday, September 14, 2010 at 2:33 PM by Wim Van Leuven

Nice job Jason. 
There is a lot of really good information here. 
How can I get copied when the videos come out?

posted on Tuesday, September 14, 2010 at 3:27 PM by Michael Parker

Be a Machete, I like that! It's all about simplicity, not simpleness. 
Oliver Wendell Holmes said, "I wouldn't give a fig for the simplicity on this side of complexity; I would give my right arm for the simplicity on the far side of complexity"  
I this and the machete comment are refering to the same thing.

posted on Tuesday, September 14, 2010 at 3:34 PM by Daniel Garcia

Great info, thanks for sharing - inspirational!!!!!!!

posted on Tuesday, September 14, 2010 at 3:40 PM by James Cook

I trully appreciate the effort to collect these gems of experience from those in the trenches!! Thanks!

posted on Tuesday, September 14, 2010 at 6:49 PM by Ligia Buzan

I love this post! i sincerely believe in the same J, we need to make a better world, trying to heal from the Industrial Age, and making valuable startups for all the people. 

posted on Tuesday, September 14, 2010 at 6:58 PM by Enrique Díaz

Thank you so much for taking the time to take such detailed notes. Almost like I was there! Thanks :)

posted on Tuesday, September 14, 2010 at 7:49 PM by Minna

I very much relate to "Business Plans and Demos Are Useless". 
Live systems that constantly interact within the world provide much better representations.

posted on Tuesday, September 14, 2010 at 9:54 PM by Allan Kirsch

Excellent Post. I guess it will take good amount of time not only just to understand these points but to constantly apply it in real environment and observe the outcome. 
It looks like most of the startups here are from IT (Software) background. It would be great if some entrepreneurs from non-IT background also share their comments and experience. 
Smit Shah 
Founder: Aash Cube Lighting Pvt Ltd

posted on Tuesday, September 14, 2010 at 11:20 PM by Smit Shah

Sorry to say, but there's nothing new there

posted on Wednesday, September 15, 2010 at 1:21 AM by Steve

This is a very concentrated dose of entrepreneurship sugar.  
Thanks a lot Jason. And best of luck for your new assignment!

posted on Wednesday, September 15, 2010 at 2:09 AM by Sid

Thanks for the recap,  
Was there any advice on ideation? Are people just coming up with ideas and then building solutions? 
Or are there more structured ways that people are finding and addressing market needs?

posted on Wednesday, September 15, 2010 at 11:26 AM by Perry Grossman

As always you come up with content rich article. Loved the following observations! 
"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." 
"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." 
Thanks for sharing!

posted on Wednesday, September 15, 2010 at 1:37 PM by Lalitha Brahma

Wonderful post on the lessons and wisdom from experienced entrepreneurs. The sad truth is that despite all of this collective knowledge about start-ups and the willingness of seasoned entrepreneurs to help the new ones, start-ups seem to make the same mistakes over and over again. One has to wonder if there is a better way to tap into this vast start-up experience better to improve the success rate fo start-ups.

posted on Thursday, September 16, 2010 at 3:59 PM by cynthia kocialski

customer support is one of the most underestimated weapon, yet very crucial. 

posted on Friday, September 17, 2010 at 12:58 AM by Sridhar Rao

David Cancel has provided some incorrect information. It is outrageous for anyone anywhere to do business without first developing a plan for management, administrations, competition analysis, brand positioning, and business viability. Anyone who fails to plan actually is planning to fail. And since the numbers don't lie over, 65% of startups close up annually, guest what...nearly all of them did not have a plan or did not facilitate a plan and stick to it. Furthermore, startups usually don't have access to a customer base that can provide reliable data. It takes months of operations to assess what needs to be measured and who to measure. All of this would be thought out through completing the business plan process. Hey I'm a SCORE counselor, we believe in business plans.

posted on Friday, September 17, 2010 at 11:29 AM by Timothy "Warp Ramp" Bard

It's outrageous to say it's outrageous for anyone anywhere to do business without first developing a plan for management, administrations, competition analysis, brand positioning, and business viability. (see post from 'Timothy Bard.) 
Yes we all know planning is important but sometimes while you are planning your competitor is doing - all the planning in the world won't make up for actually doing what needs to be done. 
Goals and approximate milestones are essential - admin plans ? less so. 
Neither way is outrageous, just different paths - everyone to their own. Peace - Steve

posted on Friday, September 17, 2010 at 1:01 PM by Steve Cholerton

re: Steve Cholerton's comment, I just want to say no one on earth has ever reached a milestone in business or anywhere else where logistics is an issue without a plan. Surely, you understand that telling people a plan is not necessary to compete with competitors is an outrageous statement. I can point out nearly 100 top CEOs who concur. Show me a reputable source that can justify going after goals and milestones without a plan. Would you invest in someone who could not communicate a plan? Really?

posted on Friday, September 17, 2010 at 2:34 PM by Timothy Bard

ref: Timothy Bard's comment: I *did not* say planning wasn't necessary - and unlike Timothy I'm not telling anybody anything, just giving my opinion and I don't feel it's necessary to talk about 'I know 100 top CEO's who agree' blah blah.  
Three years ago I given up a six figure salary (£'s) and started my own business, yes I had a plan and an idea and if I had needed funding I may have wasted a lot of time and effort on a proper 'business plan' - as it was I knew ehat I wanted to do and did it - I never had admin plans, management plans etc.  
Oh and some of the smartest and wealthiest people I know couldn't write a business plan.  
Who are you to say your is the only way ? My way works for me and many others - what's your problem with accepting that ? Is it that working for SCOPE means that your job exists only for as long as you can convince others that what you say is 'the way' ? Probably not - but you make it sound that way. I have no axe to grind here - my words come from my own experiences, not an MBA textbook. 
Live and let live - there's more than one valid opinion. Oh, and ask Steve Jobs where was his plan to sell complete computers in boxes ? That came about through seizing an opportunity, something more important than planning.

posted on Friday, September 17, 2010 at 4:25 PM by Steve Cholerton

Steve, I never made a comment towards you. Unless you are really named David Cancel. In addition I did not say I know 100 CEOs, I said I can point to (as in refer someone to their lectures and articles) 100s of CEOs. Also, I represent people completely new to business and traditional startups. Their mindset is much different from yours. Also I strongly recommend rapid prototyping as a way to develop a business. But, all you have done is attack ME, not respond to my POV or argument. I strongly suggest you look up SCORE. Did you know that SCORE counselors do not get paid for their services. Ummmm! Let go of the pain man. Obviously, you are feel sore about something.

posted on Friday, September 17, 2010 at 8:46 PM by Tim Bard

Timothy, we're in danger of hijacking this thread. I have not attacked you and I'm not sore about anything I just accept that there is more than one opinion that's valid - and neither one is 'outrageous'. As for SCORE if you provide advice voluntarilly that's great, you should be commended for that and I apologise for my words earlier.- Peace - Steve

posted on Saturday, September 18, 2010 at 6:57 AM by Steve Cholerton

the best article ive read online so far. im going to school here. thanks

posted on Saturday, September 18, 2010 at 2:05 PM by tyrell

This is an awesome summary of the talks and makes me wish I was there to hear them, especially 'funding through your customers.' Some powerful messages there. 
Thanks again, 

posted on Friday, September 24, 2010 at 12:47 PM by Tia - Webbed Ink Inc.

Seek funding through your customers- Awesome! in a business culture of "lets get lots of VC funding" this is great advice against the grain. Thanks for sharing!

posted on Saturday, September 25, 2010 at 10:00 PM by Colin8ch

Idea of "Get Inside Their Head" really works, and saves me in some critical situations as well.

posted on Tuesday, September 28, 2010 at 9:41 AM by Zaeem

A lot of great take-aways from this post. It further underscored the importance of customer development, which I continue to find so enlightening as I grow a startup for recruiters. 
I also liked and agree with 'Be a Machette'. Re-enforces principals of Keeping it Simple Stupid <a>http://techcrunch.com/2009/04/28/keep-it-simple-stupid/<a> and the Lean Startup Movement<a>http://www.startuplessonslearned.com/<a>. 
The take-away that I got that I had not focussed on yet is the importance of customer service. Ive been thinking of enabling live chat support when we re-launch our site next month. This article makes me think more about that being a good idea.  

posted on Sunday, October 03, 2010 at 1:47 PM by Allen Ackerman

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