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What It's Like To Be The CEO: Revelations and Reflections

Posted by Dharmesh Shah on Tue, Jun 05, 2012

The following is a guest post from Paul DeJoe, founder at, Ecquire, which provides contact management software and EIR at Fairbridge Venture Partners. This article is adapted from an answer on Quora that Paul left responding to the question “What does it feel like to be the CEO of a startup?” I reached out to Paul for permission to share his thoughts with the readership. At the end of the article is an epilogue with additional notes. It's worth reading too -Dharmesh

On May 20th, either right before midnight or right after midnight, I can't remember, I posted my rendition of what it feels like to be a startup CEO to a question on Quora. 1124 votes later and one last glance at a notification of an up vote from, Jia Liu, a social game maker from Zynga, I'm going to close the Quora tab and at the recommendation of Dharmesh, write what this last few days have been like, some of the cool things I've heard and some of the great people I've met as well as what I've realized.
With that said, here's the original post that sparked such a fantastic response.

What It Feels Like To Be The CEO Of A Startup

Very tough to sleep most nights of the week. Weekends don't mean anything to you anymore. Closing a round of financing is not a relief. It means more people are depending on you to turn their investment into 20 times what they gave you.

It's very difficult to "turn it off". But at the same time, television, movies and vacations become so boring to you when your company's future might be sitting in your inbox or in the results of a new A/B test you decided to run.

You feel guilty when you're doing something you like doing outside of the company. Only through years of wrestling with this internal fight do you recognize how the word "balance" is an art that is just as important as any other skill set you could ever hope to have. You begin to see how valuable creativity is and that you must think differently not only to win, but to see the biggest opportunities. You recognize you get your best ideas when you're not staring at a screen. You see immediate returns on healthy distractions.

You start to respect the Duck. Paddle like hell under the water and be smooth and calm on top where everyone can see you. You learn the hard way that if you lose your cool you lose.

You always ask yourself if I am changing the World in a good way? Are people's lives better for having known me?

You are creative and when you have an idea it has no filter before it becomes a reality. This feeling is why you can't do anything else.

You start to see that the word "entrepreneur" is a personality. It's difficult to talk to your friends that are not risking the same things you are because they are content with not pushing themselves or putting it all out there in the public with the likelihood of failure staring at them everyday. You start to turn a lot of your conversations with relatives into how they might exploit opportunities for profit. Those close to you will view your focus as something completely different because they don't understand. You don't blame them. They can't understand if they haven't done it themselves. It's why you will gravitate towards other entrepreneurs. You will find reward in helping other entrepreneurs. This is my email address: paul[at] Let me know if I can help you with anything.

Your job is to create a vision, a culture, to get the right people on the bus and to inspire. When you look around at a team that believes in the vision as much as you do and trusts you will do the right thing all the time, it's a feeling that can't be explained. The exponential productivity from great people will always amaze you. It's why finding the right team is the most difficult thing you will do but the most important. This learning will affect your life significantly. You will not settle for things anymore because you will see what is possible when you hold out for the best and push to find people that are the best. You don't have a problem anymore being honest with people about not cutting it.

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You start to see that you're a leader and you have to lead or you can't be involved with it at all. You turn down acquisition offers because you need to run the show and you feel like your team is the best in the World and you can do anything with hard work. Quitting is not an option.

You have to be willing to sleep in your car and laugh about it. You have to be able to laugh at many things because when you think of the worse things in the World that could happen to your company, they will happen. Imagine working for something for two years and then have to throw it out completely because you see in one day that it's wrong. You realize that if your team is having fun and can always laugh that you won't die, and in fact, the opposite will happen: you will learn to love the journey and look forward to what you do everyday even at the lowest times. You'll learn not to get too low when things are bad and not to get too high when things are good and you'll even give that advice. But you'll never take it because being in the middle all the time isn't exciting and an even keel is never worth missing out on something worth celebrating. You'll become addicted to finding the hardest challenges because there's a direct relationship between how difficult something is and the euphoria of a feeling when you do the impossible.

You realize that it's much more fun when you didn't have money and that money might be the worse thing you could have as a personal goal. If you're lucky enough to genuinely feel this way, it is a surreal feeling that is the closest thing to peace because you realize it's the challenges and the work that you love. Your currencies are freedom, autonomy, responsibility and recognition. Those happen to be the same currencies of the people you want around you.

You feel like a parent to your customers in that they will never realize how much you love them and it is they who validate you are not crazy. You want to hug every one of them. They mean the World to you.

You learn the most about yourself more than any other vocation as an entrepreneur. You learn what you do when you get punched in the face many many times. You learn what you do when no one is looking and when no one would find out. You learn that you are bad at many things, lucky if you're good at a handful of things and the only thing you can ever be great at is being yourself which is why you can never compromise it. You learn how power and recognition can be addicting and see how it could corrupt so many.

You become incredibly grateful for the times that things were going as bad as they possibly could. Most people won't get to see this in any other calling. When things are really bad, there are people that come running to help and don't think twice about it. Tal Raviv, Gary Smith, Joe Reyes, Toan Dang, Vincent Cheung, Eric Elinow, Abe Marciano are some of them. I will forever be in their debt and I could never repay them nor would they want or expect to be repaid.

You begin to realize that in life, the luckiest people in the World only get one shot at being a part of something great. Knowing this helps you make sense of your commitment.

Of all the things said though, it's exciting. Every day is different and so exciting. Even when it's bad it's exciting. Knowing that your decisions will not only affect you but many others is a weight that I would rather have any day than the weight of not controlling my future. That's why I could not do anything else.


In the post, I had shared my email with everyone to see with the hopes of encouraging anyone that needed any help to reach out to me directly. I was fortunate enough that so many people took me up on this offer. The exchanges we had ranged from skype calls, testing some new products, sharing ideas and even joining an advisory board. Most of the emails I got though were just people that thanked me for the post, shared their contact information, and said things like David did:
"…likewise, if there's any way I can be of help or service, let me know."
For those of you that have reached out to me and shared some of your life with me, thank you beyond words. It has been flattering, fulfilling and, and humbling. For those that have voted up the answer and said some of the kindest, coolest and most amazing comments anyone could ever hear. I thank you. And my startup parents thank you. Suddenly the 80,000lb student loan Gorilla with no income to feed him seemed to take the week off and was replaced with elation when reading some amazing comments. It meant a lot. Thank you again.
What might be a surprise to hear though is that it felt very uncomfortable to me to say "thank you" and I was doing it a lot. Seemingly overnight, there was a collective up vote from over 1,000 people that shared similar feelings and situations. I started to get the feeling that this wasn't me that wrote this and became uncomfortable taking credit. This post gained attention because it was the collective post by everyone who contributed with a comment or a vote and if I hadn't been lucky enough to come across this question, someone else would have wrote this. It might have been better or not but it would have at least been appreciated in the same way had another entrepreneur wrote it.
I don't recall seeing too many notifications of a down vote and that made me realize a few things:
This post became an online meet up for a group of people that are committed to changing the World. And rightfully, as well as fittingly so, it's very difficult and a sometimes a seemingly unsurmountable undertaking. But what was encouraging was not one person in the entire comments (go ahead and look) or in the emails that I received, said that they were overwhelmed or going to quit. They all found this inspirational and motivating and just the little encouragement needed that led to a found appreciation for what they do and and a reminder that they're not the only crazy ones.
The most common response I received however sounded like: "Thank you for this. I forwarded your answer to my friends and family to help them understand." One person even said that their Mom thanked me for the post (Thanks, Renee for sharing). Unfortunately, and sometimes rightfully so, entrepreneurs are commonly misunderstood by people outside of our networks and by people we love. It's mostly our fault. Although we are not understood most of the time, we take for granted that while we're often misunderstood, we are always accepted and supported. What we don't say thank you enough for, and what we often take for granted, is the very thing that let's us be who we are and chase our dreams. The people around us that love us unconditionally without regard for how bad we might fail is the equivalent of a superhero's cape. Without this, and without someone we can share the ups and downs with, great things do not happen. They can't. The things that are worth while to pursue and dedicate a life to involve something way bigger than individuals and have to be completely selfless or they are not big enough and not worth celebrating if the goal does not have the well being of others in mind. A collective thank you on behalf of this group of people that are crazy enough to change the World goes out to you. Thank you. If you are reading this because it has been forwarded to you, please know that you are appreciated and it's difficult for, often times quirky introverts to articulate. You don't have to change anything, we don't say it enough but it's with you in mind that we find motivation. You possess the most scarce resource of all: Undying and unnerving support. Thank you for it.
Lastly, undoubtedly the greatest thing that came from this post was an amazing calm that came over me that was during the most fulfilling, rewarding, interesting and fun week of this tumultuous journey to build a company. It came at the intersection of being able to interact with all of these individuals and being able to see all at one time, the collective resolve, ambition and just how dynamic these people are. The content of who these people actually are, how many of them there are and that they actually exist under our noses, let my imagination of what was possible wander in a positive direction for the first time in a while. It was powerful enough to spin the negative outlook I thought we were inevitably leaving for future generations. What I have just said, you would have not heard me say one week ago. It also made me realize something for which I will forever be grateful to all of those that contributed to this post. I realized what I am supposed to do to be fulfilled and happy in life:
I can tell you first hand, from over 1,000 data points and messages, that there is no better feeling than when you inspire or when you can help. When you genuinely help, it's a good feeling that is impossible to suppress. It's impossible to suppress for a reason: It feels good in the most selfless way possible. Entrepreneurs will make their own mistakes along the way, millions in fact. They have to to learn and improve. Don't discourage them from trying. There's no reason to. It's a useless thing to do and it might be enough to delay the doctor that cures cancer or the visionary that brings sustainable water to Africa when a simple word of encouragement was the only push they needed.
Inspire. Help and do so with other people and future generations in mind. Wouldn't it be the coolest thing in the World if we were the generation that consistently got punched in the face, didn't complain, didn't slow down, picked up our lunch pales and went out everyday to create sustainable opportunities for a generation that we haven't met yet? If that sounds crazy, ambitious, and delusional it's because it is and that's the way we have to have it or it's not worth our time. As crazy as it sounds, I can assure you that it will only require one thing for all of us to do for it to become real. It requires that we all inspire. 
What do you think?

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Founder Focus: Don't Kill Your Startup With 1,000 Trivial Tasks

Posted by Dharmesh Shah on Mon, Mar 05, 2012


This article was written by Noah Kagan, the Chief Sumo at (#1 ecommerce site for entrepreneurs). He was employee #4 at and employee #30 at Facebook.

A few weeks ago I had wine with some very successful entrepreneurs. How successful? On their best days they were generating $100,000 a DAY in revenue. That’s $36,500,000 a year.

Insanity, huh?

But what was the most surprising thing to me was that they were STILL doing their own data entry and dealing with small clients. multi tasking woman

Holy crap. Think of it this way:

Let’s calculate their hourly sales:
$100,000 / 8 hours a day = $12,500
Divided by 2 guys = $6,250 / per hour

Do you see where I am about go with this? :)

After spitting out my wine, I started berating them with hate words about how dumb they are and why aren’t they focusing on higher-value things for their business?

Their response?

“We want to make sure it gets done right.”

Ahh, now it makes sense. They have Jewish mothers and are control freaks.  (disclaimer: I'm proud to also have a Jewish mother.)

This is something I had a problem with myself, once upon a time: We want to do everything ourselves, which means we aren’t focusing on the highest-value things we can be doing for our business.

I used to do the same kind of data entry. I’d write up the emails for, do customer support emails (which I actually like, most of the time), and other low-level things.

It all changed when my buddy Joe from MyChurch opened me up to outsourcing.

“Come on, Joe. Those people are crappy and it’s so weird,” I said.

He finally convinced me, so I had Nimesh Mehta at $4 / hour start aggregating certain data from me.


It wasn’t about outsourcing to India. It WAS about maximizing the best use of my time.

As an example: what do you think is a better use of my hour?

1. Writing this article that hopefully gets 500+ people to discover and check out, or
2. Doing data entry to put a new deal in our system.

Take a guess.

Writing this article, of course! It generates way more value which is a way more ROI / value / monetizable use of my time.

Coming back to how you can save yourself before it’s too late:

- Start small. When hiring other people to do your tasks, you need to be concise in your instructions. Delegating is a skill (not a talent) gained from experience.

- Think investment. Don’t think of outsourcing as a cost. I LOVE hiring for AppSumo!

- Guard your time. Next time you think about doing something, think if you are REALLY adding value (i.e. only your special skills can do it) or if someone whose value of time is lower could handle the task instead, thereby freeing you up for better things.

That's fine and all, you might be thinking, but aren't there some seemingly trivial tasks that keep me closer to the business? Like customer support-- how do you find the right balance between outsourcing/delegating and maintaining the little things that make the business differentiated and special?

Trivial tasks will never go away. Invest in the things that matter. Wow, I can throw a few more cliches just to finish off the article nicely.

Look, if support is going to be a differentiater like we want it to be at AppSumo then we don’t try to pass off phone support, live-chat, email, etc. to a lower wage person. But processing refunds, merging email accounts and helping the customers get what they want can be passed off.

I guess the ultimate balance comes from identifying what is important to you. I still like updating Excel each month with my finances vs. using (which I helped build). Doesn’t make it the “right” choice, but it makes me happy.

A helpful tip to see how you can start evaluating what you want to delegate is to literally write out your entire day by tasks. I did this with Andrew Warner from too and it seemed really helpful. Then pick out the things that are high-value or you personally get value from doing. Keep those. The rest of the stuff, get someone else :)

What do you think?  Have you identified the key areas to apply your time and energy, and shifted the rest?  What's working for you?

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The CEO Should Be The Chief Experience Officer

Posted by Dharmesh Shah on Tue, Nov 15, 2011

Earlier this week, I was chatting with my friend, co-founder and CEO of HubSpot, Brian Halligan. We were doing one of our ad-hoc strategy sessions about the business, and working through some things.

After that conversation, as I was driving to a dinner meeting, an idea occurred to me. The phrase “Chief Executive Officer” doesn't convey much, if anything. There's a better way to describe the wrench

I will posit that in a technology company, the CEO should be the Chief Experience Officer.

If the CEO can make the following set of experiences amazing, by definition, she will make an amazing company.

1. Product Experience: What is the experience like using the product and getting value from it? Does it solve the problem simply? Does it make users happy, productive and hopeful when they're using it, or does it make them frustrated, angry, agitated and depressed?

2. Purchasing Experience: What is it like to go through the sales process and buy the product? Was it easy to figure out whether the product was the right fit? Was the pricing straight-forward? Was the buying process smooth without unnecessary steps and complexity?

3. Brand Experience: What is it like to interact with the company's brand? Does talking about the company with others ignite passion? What kind of emotions does it evoke? When people see the logo online or offline, what's the visceral reaction?

4. Support Experience: What is it like to receive support from the company? Do people dread having to call in and get help? When they do make contact, do they feel like the company cares not just about appeasing and pleasing — but that the actual problem is addressed?

5. Exit Experience: What is it like to leave the company, return the product, or cancel the subscription and no longer be a customer? Sometimes you can tell more about a company by how it treats customers on their way out, than on their way in.

6. Employee Experience: What's it like being recruited by the company? Working for the company? Being let go from the company? If you have a terrible employee experience, you will not attract the kinds of people that will make the customer experience amazing. It just doesn't work.

Notice that most of the above experiences are all about the customer. How does the customer experience the company? I think that's the primary set of experiences the CEO should worry about. The reason is simple, by improving the overall customer experience, everyone wins. Including the investors/shareholders (and yes, the CEO also needs to manage the shareholder experience too).

So, Don't just improve the product, improve the experience. This is one of the points I made in my Business of Software (2010) presentation (I think it was one of my better ones, full video and transcript available).

What do you think? Am I over-thinking the importance of the overall experience? Any lessons learned or tips on how to measure and improve the end-to-end experience?

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Startups: Why What You Build Is Less Important Than Who You Build It With

Posted by Dharmesh Shah on Wed, Feb 14, 2007

I’m in the middle of reading “Founders At Work” by Jessica Livingston.  The book is basically a collection of interviews with founders of some prominent software startups.  What I like about the book (I’m about half way through) is that the interviews are pretty detailed and Jessica does a great job of giving the founders enough time to get their thoughts out.  They cover issues ranging from the conception of the idea, team dynamics, investor dynamics, etc. All the things that you’d expect to go on within a startup.  In any case, the book is good and I’ recommend it (it is one of the few ones that has made the OnStartups Reading List.


But, this article is not about the book (I’ll plan to write a fuller set of thoughts on that in a later article once I’m done reading it).  This article is about the importance of your early founding team to the likelihood of a successful outcome for your startup.


The title pretty much says it all:  I think the idea that you are basing your company on is likely less important than the team that you create to pursue that idea.  Here are some thoughts as to why.


Why What You Build Is Less Important Than Who You Build It With


  1. The Idea Can (And Should) Change:  I’ve read numerous times that most startups that end up being “successful” will change the idea along the way.  I recall from a Clayton Christensen presentation that his studies indicated that on average startups change their basic idea/business about four times before finally landing on the one that makes them successful.  He actually goes further and says that in order for startups to succeed, they need to be flexible and have the ability to change the idea based on market feedback instead of doggedly sticking to their original plan.  So, the point here is, your initial idea for the startup, as brilliant as it might be, is probably going to change anyways – multiple times.  For this reason, it doesn’t seem prudent to get overly attached to the idea or give it too much weight in the early stages.


  1. The Team Shouldn’t Change:  Startups are an exercise in trust building with a group of motivated and competent people.  Unless you have worked with these individuals before, it can take a fair amount of time to do this.  As such, changes to the “core” team of a startup can be extremely disruptive.  I’ve seen more startups fail because of founder conflict, high management-team turnover and other “people” issues than issues with the technology or the idea.  So, picking this early team and making sure you are coming together with a clear understanding is critical.


From “Founders at Work”, one of my favorite quotes so far has been from an interview with Joe Kraus, the founder of Excite and JotSpot.  I’ve heard Joe speak and he seems a particularly intelligent and insightful guy.  Joe says:  “People make all the difference in the world.  Venture capitalists would tell you that they’d rather fund a great team than a great idea.  The reason is that if they have a bad idea, great teams can figure out a better one.  Mediocre people even with a great idea can screw it up in its execution.”  I’d further add that mediocre teams may also be less likely to detect a bad idea, so may be more likely to stay on the wrong path longer than they should.


In my current startup, HubSpot, the words are ringing very true.  My co-founder, Brian Halligan and I met as graduate students at MIT.  We got to spend a fair amount of time together and learning about how each of us “thinks about stuff”.  Though we have very different backgrounds (his in sales and mine in technology), we both have similar approaches to problem solving.  We like to analyze, dissect, discuss and debate.  We love abstractions and we love to seek patterns.  This approach has helped us with HubSpot, because as expected, the underlying idea behind the business has already changed considerably since the company was originally conceived.  The good news is that we’re able to openly talk about things and not hold any punches.  If Brian thinks I’m wrong, he’ll tell me (with pretty good reasons as to why).  


How about you?  Have you found that your startup has needed to change ideas, or did you happen to “get it right” the first time?  What about the people?  Are you still with the same core team or did this end up changing for some reason?  What were the lessons learned?  Would love to hear from you.


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Startup Founders: Are You Too Assertive, Or Not Enough?

Posted by Dharmesh Shah on Mon, Feb 05, 2007

I came across an article recently titled “Researchers Uncover Best Bosses’ Success Secret”.  I was hoping to find some revealing insight about what makes great bosses.  Unfortunately, I really didn’t glean that from the article.


Basically, the point the article makes is that the most successful bosses tend to find a good balance between being too assertive (and possibly aggressive) and being too nice.  I found this particular revelation to be less than satisfying.  Seems overly obvious that like with many things, balance is key and the optimal value rarely lies at either extreme.


I thought a bit about this and began to wonder how this balance might be found within startup founders.  I talk to startup founders all the time, both successful and not-so-successful.  Is there a particular leaning one way or the other?  Is there a pattern?  I’m not sure.


Here are some of the thoughts/ideas I had.  Feel free to push-back or make counter-arguments.


  1. Startups that have raised venture funding seem to me to be more assertive, on average, than those that haven’t.  This doesn’t surprise me too much.  I’m guessing that VCs, like other people, gravitate towards others that are like them.  VCs are a relatively assertive bunch so it would not surprise me if they were more likely to fund similarly assertive entrepreneurs.  Further, the entire process of VC-fund raising seems to favor the assertive.


  1. Startups that are bootstrapped may exhibit the opposite characteristic (particularly software startups).  In order to recruit a talented software team, founders of bootstrapped startups have to offer something other than high cash compensation and monetary rewards.  One of those things might just be that they’re easier to get along with and fun to be around.  Think about it:  If you were a software developer looking to take a big stake in an early-stage software startup and work for a below-market salary, are you more likely to pick an uber-assertive (or aggressive) founder or one that is more laid-back?  I’d pick the laid-back one.  Similarly, if the company is venture-backed, it can afford to pay competitive salaries and hence hold people accountable.


Clearly, I’m painting in broad strokes here and am dancing a fine line towards stereotypes, but I like to think in stark contrasts sometimes, as it helps identify patterns that are sometimes useful.


What do you think?  Are there any patterns you’ve seen when it comes to degree of assertiveness in startup founders?  Which way do you lean?  Do you think this helps you or hurts you?


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