The 3 Most Painful Parts of Leaving My Job at HubSpot

I recently left my job at HubSpot to strike out on my own again (learn more here). It’s been an amazing change so far and I’m super excited about what’s the come, but I’ll be honest and admit it hasn’t been all roses. Since I’ve never left a real job before, I didn’t really anticipate some of the more painful aspects of making such a dramatic change, so I thought I’d share them here.

Losing parts of my digital memory

When I left HubSpot and my work email was shut down, I lost access to a lot of the history around building Leadin. I lost access to my contacts. I lost my Google Docs. It’s amazing how much personal information we store in our work accounts. When you lose your accounts, it like losing a piece of your brain.

Losing my extended community

I braced myself for not working with my direct team mates anymore, but I didn’t prepare myself for losing my extended team. Habits like checking the company wiki when I woke up in the morning were no longer possible. Saying hello and striking up a casual conversation with people in the halls doesn’t happen. It’s easier to focus on GSD when you don’t have many people to talk to throughout the day, but I do miss the small interactions + random conversations.

Recalibrating my top of mind idea

By far the hardest part about leaving HubSpot was recalibrating my brain to not think about Leadin anymore. Leadin occupied my mind almost every waking hour of my day (and sometimes in my dreams). Making such a dramatic shift was painful and I didn’t transition as well as I wanted. I felt a lack of purpose and focus the first two-three weeks because it took me time to shift my top of mind idea. Time heals all, and I’ve transitioned through the five stages of loss, but it definitely was a pain I didn’t anticipate.

Starting up again

Almost two years to the day I started working on Leadin inside of HubSpot Labs with Nelson Joyce after my startup, Rentabilities, was acquired by HubSpot.

During that time I learned a tremendous amount about products, startups and how a well-run thousand-person company operates. I worked alongside my friend day in and day out, grinding away to make a product people loved. I made new friends, like the amazing team from Dublin who banded together with us to rebuild Leadin from the ground up. I saw Leadin launched in front of 13K people at INBOUND this year. Most importantly, I helped build a product that brings the power of inbound to every body.

It’s been an amazing journey and I’m super thankful to HubSpot for giving me the opportunity to create Leadin inside the company. Now it’s time to take all those learnings and start over again with Nelson to build a company of our own. We aren’t publicly talking about the exact product we’re cooking up just yet, but if you’re curious you can sign up for our mailing list below.

What’s going to happen to Leadin?

Well, nothing’s really going to change. The current team is going to keep cranking away on Leadin and I have 100% confidence the product will continue to get better.

How schooner-sized startups can beat aircraft-carrier-sized companies

All startups start with nothing. No product. No customers. No growth. Nothing.

The incumbents have it all. A fully functioning product. Millions in revenue. Distribution channels that are working.

It must really suck to be a startup then, right?

But the counterintuitive answer is no – it’s actually you’re biggest asset to start completely from nothing with a blank slate.

Here’s why…

Large companies are like aircraft carriers

Aircraft carriers are the most formidable ships on the planet. Within a few hours they enable a country to launch an assault on another nation with air support. The United States operates 10 active aircraft carriers around the world. They are the cornerstone of the Navy.

Large companies are like aircraft carriers. If a large company gets its sights on you because your too close to their market, they have the power to destroy you. This comes through in the classic VC question, “what if Google does this?”

The reason why a large company got so large is that is kept improving its ship over time by growing, and the only way to grow that large is though process. Process keeps the hundreds of people all working together from falling into chaos. If you didn’t have process, you couldn’t move the ship because the ship is too large for one person to see the entire vessel at a glance. So you have to trust the process that you’re doing your job, and your crew mate is also doing her job, and since every one else is executing too, all parts of the ship can work in tandem to plow forward. Occasionally an air squadron can be sent out to wipe out a threat in range, but the planes always have to fly back to the ship.

Moving an aircraft carrier takes a long time. To change coarse many things need to happen at once. First, the captain has to decide where to go. Next, she needs to loop in all the right people so they can disseminate the news to the rest of the crew. Last, the direction is changed, but you have to wait awhile because aircraft carriers are so large that change in direction happens over a long time. Since aircraft carrier has engines eventually it’ll get there, but it can’t change coarse quickly.

Startups are like schooners

A schooner is a small sailboat with two masts. They range in size by can typically be sailed by between 2 – 10 people.

Before the age of the small onboard motor, schooners were strictly sailing vessels. The didn’t have motors. They were powered by the wind. Startups are also powered by the winds of market demand. You don’t decide where you want to go, the market decides for you. Your job as the captain is to realize when the winds change and sail with them as hard as you can. And since you’re in a small boat, feeling the feedback of the wind on your face, you can change direction quickly.

The great thing about schooners is that they are small. You can yell to your crew mates when something goes wrong for help. You don’t need fancy communication systems, you just see the issue and yell with your voice. You don’t have many fancy systems so you usually fix bug issues by hacking something together using common sense. When something goes wrong, you don’t need to respect chain of command and work your way up to the captain. You just yell for your captain who comes over and talks to you, a decision is made and you change direction. 

Enough with the boats! Why does this matter?

The reason why this matter is because lack of customers, processes and people is your biggest strength. When you’re starting with nothing, no one expects much of you. Your customers don’t care if you have a small or big free product. If you’re doing it right, you should be solving something so painful that whatever you give them is a step up from what they had before. And since you don’t have millions of users or revenue depend rant on your systems, you don’t have to worry about breaking the infrastructure or the businesses processes when you launch sown thing new. You can scale it as you grow.

I had to relearn this lesson the last few weeks while working on Leadin. We recently rebuilt the entire backend for the product on the cloud. The plan was to clone all the features over on a more reliable stack than WordPress and launch nothing new. This meant we had to clone not only our core app, but also all our onboarding, integrations and figure out a way to migrate our existing thousands of users.

Eventually though I realized we should operate like the early days. In the early days we didn’t have onboarding and people still used the product. We didn’t have 5 email integrations, we only had one with MailChimp, and people still used the product.

And if you think about it, people don’t know what they don’t know. New users checking out LeadIn for the first time don’t know there should have been onboarding there. They don’t know that in the old version they could integrate with a few more email services, which they most likely aren’t even using in the first place.

Once our team figure this out, we were able to start stripping out the none essentials even more and ship the new version of Leadin weeks earlier than we planned. Launching that version felt great and reinvigorated us to finish cloning the last of the features because the product was in the wild now. 

Even with only a couple thousand users we feel into the optimization trap. Cut features that aren’t crucial. Ship the product before you’re ready to figure out if you should even scale it in the first place. Always avoid operating like a battleship and sail your startup like a schooner.

To Consume, Contemplate or Create? That is the question.

We will in an amazing era. Humanity’s collective knowledge travels in our pockets with us everywhere we go. We can instantly communicate with anyone in the world in a few taps of a button.

With great power comes great responsibility though and the truth is our phones act like tractor beams for our attention, powered by addictive apps designed by experts in creating habits. I’m sure I’m not the only one who instinctively feels the need to grab my phone during every small moment of downtime to check the latest and greatest the Internet has to offer. One of my goals in the coming weeks is to consume less and to contemplate more, then those thoughts into creations.


Everyday millions of tweets, Instagrams and updates are posted. Billions of emails are sent. With 2.6 billion words in the English Wikipedia, there’s a lifetime’s worth of reading there alone. 

Consuming is fun. It gives our brain’s a quick dopamine hit of accomplishment. But it’s also dangerous. Our brains lose 50-80% of what we learn after the first day. There’s also no tangible artifacts that you read something. If you can’t remember what you consumed  and there’s no proof that you spent the time, did it actually really happen?

Don’t get me wrong. I think learning and believe consuming is an important step toward sparking new ideas, but it shouldn’t be 100% of all idle time. We should consciously make sure we’re applying the knowledge accrues towards developing new insights. 


Contemplating (or better know as thinking) is the next rung on the good use of idle time ladder. Thinking about what you read, digesting it and using those that new information towards developing original thoughts throughout the day is a rewarding process. I actually don’t do this enough anymore. It’s a rare occupancy when I just sit by myself outside and think – no humans, no phone – just me and brain mulling over the world. 

Contemplating is surprisingly meditative. Letting your mind wander in whatever direction it want is a welcome break from th always on distractions a of the day. It reminds me of the minutes before you fall asleep where you have an amazingly deep thought because your mind is cut off from any distraction. 

Contemplating is a much better use of time than consuming. Were inundated with new inputs and we rarely spend enough time digesting  it all. Unfortunately with the always-on expeditions of society we don’t take time for ourselves anymore to exercise our brains.

In fact, this entire blog post is a result of purposely taking the long walk to the coffee shop. I cut myself off front technology and ended up realizing I should spend less time on my phone and more time with my mind.

The main issue with contemplation is that it suffers from the same weakness as consuming. You don’t create a footprint by just contemplating and the rest of the world doesn’t benefit from you’re thinking. Which brings me to the highest form of idle time…


Above all else there is creation. Making the jump from consuming, to contemplating to creating is hard and a process I struggle with constantly. Creating is the most rewarding use of time thought. Unleashing your thoughts through creating helps you. It creates more opportunities to connects. It helps build a reputation for original thoughts. It shows you can execute. And above all else sharing your creative work may strike a chord with another person.

Some of the people I respect most, and ultimately ended up getting to know are the creators. They are the people who shared a blog post I desperately needed to read for validation during the hardest times of my startup. They are the people who post an interesting quote that I can relate to. They are the people who help me think through my thoughts and make sense of the world.

How do they find the time though? How do people write a blog post a day?

On my walk this morning I realized… They make the time. Th easiest way for me to make the time time is to convert the dozens of moments where I typically consume into creation time. I have a device in my pocket that empowers me to share my thoughts, so I’ve decided to utilize it. Sharing now only helps others, it’ll help me too.

I want to be a creator. I want to help others by sharing what I can. I want to help my future self. So here goes nothing… My new goal is to consume less and create more. Stay tuned.

Startups are a Grind

Here are some of the things people think founding a startups brings you:

  • Launch parties
  • Funding announcements
  • Speaking at conferences
  • Choosing your own schedule
  • Being your own boss
  • Successful exits
  • Stacks and stacks and stacks of cash.

Here’s a slightly different and more realistic list of what founding a startup adds to your life:

  • Writing code
  • Fixing bugs
  • Answering customer support tickets
  • Paperwork
  • Bookkeeping
  • Emails
  • Taking out the trash – literally

The reality is that startups are a grind and take daily progress day in and day out. There’s a reason why there isn’t a popular reality show based on starting a tech company. Every episode would be almost identical – 30 minutes of watching people typing away on keyboards with headphones on.

When you see a company in TechCrunch or the New York Times, you’re reading about one moment in time which is often deliberately delivered in an exciting narrative, but not really indicative of what that team is working on day in and day out.

From what I can tell, the most successful startups just keep their heads down and headphones on, making progress little by little every day to build something their customers love and grow that use base. Focus on making progress and the rest of those exciting milestones will fall into place.

Startup Competition Means You’re Probably Heading in the Right Direction

I loved video games as a kid, and yesterday I stumbled across a meme that made me chuckle:

if i've learned anything from video games, it is that when you meet enemies it means that you're going in the right direction

I think this meme also holds true for startups, so I readjusted it:

If I’ve learnt anything from startups, it is that when you meet your enemies, it means that you’re going in the right direction.

So often competition bogs us down, keeping us awake late at night and causing our blood pressure to spike. I still remember the day I found the first competitive startup to Rentabilities. Then another rental marketplace cropped up a few months later, then three more the next year. Each time I encountered a new enemy, my inner-competitor wanted to goomba stomp each one into oblivion.

goomba stomp
How to Goomba Stomp

As the years went on, I realized our fiercest competition was not another startup and that competition in the market is a good thing. Startup founders tend to be some of the most intelligent, competitive and driven people. If other smart founders are investing their time into a similar idea as your startup, it probably means there is something interesting about the market and it’s worth pursuing. If one of those startups raises funding, that is even better for you because it validates the market even more, giving you fodder for your own investor meetings. Your company is more likely to die by self inflicted wounds than by the sword of another startup.

Stop worrying about the competition and focus on your product, your customers and yourself.

And if you need some motivation, remember what Alexis Ohanian says:

Lives Remaining 0

Make it count.

Big Startups Have Small Beginnings

tree and sapling

What do Facebook, Twitter, DropBox, Groupon, Airbnb and every other company in the world have in common?

They all started as ideas with no customers, no revenue, and no product.

Yesterday I met with a friend to talk startups over a coffee. He’s currently employed at a great company, and is thinking of taking the leap and starting his own startup. For about an hour we ran through his initial list of product ideas, discussing the opportunities and potential pitfalls of each one, eventually zoning in on a specific idea around the college market. Now that we had pinpointed one of the ideas, I finally asked, “When are you going to start?”. He paused. And winced. I could see he was torn, but after a moment he finally answered, “Not yet… I feel like I need to go all-in to really do this idea justice, but I have to admit I’m scared to take such a huge risk and leave my job.”

His response got me thinking about a myth that exists in the startup community. The myth that you’re not making real progress until you’re working full-time on your startup. I started questioning this line of reasoning, and decided to recap my thoughts in this post.

Start Small To See If You Should Start at All

“A complex system that works is invariably found to have evolved from a simple system that worked.” – John Gall

Did you know the founders of Airbnb started by renting out their own apartment, initially hosting three guests on air mattresses for a design conference in San Francisco? They didn’t start with a huge, grand plan to disrupt the hotel industry. Instead, the plan was to figure out how they could pay their rent for the month, so they hacked together a static web page showcasing their “bed and breakfast”, posted it online, and made $1,000 their first week by hosting three guests. That’s it.

One of the mistakes I see new startup founders make is believing that the only way to start a business or new product is to go all-in. Building something new requires configuring many complex parts, and it’s easy to get discouraged by the sheer amount of work it’ll take to start, especially if you’re working full-time. Most people never even get started, instead choosing to wait until the time is perfect. But that’s the thing with startups and life and the everchanging responsibilities we all have that eat up any free hours we might get to work on a fun new product. The perfect time just never comes.

To finish up my story from earlier, I ended up convincing my friend he should not leave his job yet, and instead start by talking to a few undergrads, maybe even test his idea by offering to mentor a handful of students personally and teach them how to gain work-related experience while still in college. It’s not a glamorous way to start, but by doing things that don’t scale, he’ll learn faster than by building out an entire product based solely on assumptions. From those simple learnings he can start to layer on complexity, eventually evolving a more scalable solution if the initial idea proves to be worth pursuing. Airbnb morphed from three guys renting out blow up mattresses into a multi-billion dollar business through the same evolutionary process.

As humans, I think we all possess an internal desire to build and achieve great things. I’m constantly reminding myself to counterbalance that drive with the realization that all big successes stem from tiny beginnings, and it’s ok to start almost laughably small.

What are some samples of projects that started small for you and eventually grew into a success? What are some other methods you use to get going on a new project? I’d love to hear your thoughts below.

Thanks to Alex Cook, Nelson Joyce, Josh Porter, Rachel Roizen and Derek Sivers for reading drafts of this.

Photo by the talented varintsai

A Note to Myself – Remember Why You Write

Andy… you need to start writing your blog for yourself…

Don’t worry about who else reads it. In the long run, tweets don’t matter. Likes don’t matter. Shares don’t matter.

Your content spreading is a noble goal because maybe it’ll help one of two people, but optimizing for sharing shouldn’t be the goal.

In case you forget tomorrow morning…the goals of your blog should be:

– Clear out your brain some top-of-mind thoughts by archiving them through writing
– Bolster your efforts to understand the world and satisfy your curiosity
– Document life’s journey and the progress you’re making
– Internalize the lessons you learn through writing
– Actively practice your communication skills
– Introspect and grow as a person
– Relax

Stop trying to come up with the perfect witty phrase. Stop trying to write viral content. Stop trying to write for others.

Instead, just be honest with yourself and the world might want to listen too.

The Real Truth About Startup Geniuses

Starting my first company was an eye opening experience because it made me realize I had absolutely no idea what I was doing. New challenges seemed to pop up every day and I stumbled my way through each and every one.

The best resources I found to help with my incompetence were books and blogs, but reading advice from successful founders often made me feel more inept. Those startup geniuses must possess a superior intelligence because of their successes. They must be more innately capable of building a company because they all seemed to know exactly what to do in every situation.

The funny thing is, as I eventually met and became friends with a few of those bloggers over the years, I realized everyone is figuring it out as they go. Behind every great success story are mistakes and hard-earned lessons. We just often don’t hear about them.

I try to remind myself now that everyone starts from nothing and it’s ok to suck at the beginning. No one knows how to solve a situation when it’s first encountered. Even impressive entrepreneurs like Drew Houston have knowledge gaps to fill:

“I was living in Boston, working for a startup during the summer, living in my fraternity house. But every weekend, I would take this folding chair up to the roof with all these books I got on Amazon. I would just sit there and read all of them. I would spend the whole weekend just reading, reading, reading. I’d be like, alright, I don’t know anything about sales. So I would search for sales on Amazon, get the three top-rated books and just go at it. I did that for marketing, finance, product, engineering. If there was one thing that was really important for me, that was it.”- Drew Houston

So don’t be afraid to try something new because of fear you might suck at first.

Don’t be afraid to start a company because you lack experience.

If you’re smart, pay attention to details, trust your best judgement, and persevere, you’ll quickly figure it out too.

Or as my favorite cartoon dog once said…

Sucking at something is the first step to becoming sort of good at something

The Founders Guide to Surviving Startup Life

founders survival guide

I used to feel a sense of accomplishment after working 100 hours in a week. That is what startups are all about, right? Long hours grinding it out in front of my computer hacking away on your startup living off ramen.

Wrong… I now realize I was trading short term gains for the long term health of myself and my company.

The startup world glorifies The Struggle because it’s the epidomey of the American dream. A smart, talented underdog takes a risk on himself and struggles for years, only to become wildly successful. We’re fascinated by a founder who pitches 80 VCs while living in his car for three months and finally closes on a term sheet. If that same founder goes onto create a billion dollar company, his story of grit is retold, perpetuating the myth that you need to grind it out to be successful.

Unfortunately, passion and grit do not turn you into a machine and after a year or two, your adrenaline reserves will empty. You are still a human and your brain and body have limits. If you burn out physically and mentally, your willpower is broken and you’re likely to give up. Therefore, the best way to make sure your startup doesn’t die is to avoid burnout in the first place.

Recently I’ve decided my new side project will be working on myself. This list of habits help me acheive more focus, energy, and happiness. My habits are in constant flux and I’ll be updating them as I learn what works and what doesn’t to stay in balance.

I wrote this post mainly for myself, but my hope is that by sharing, I can help a few entrepreneurs who are struggling with balancing the startup lifestyle and a healthy lifestyle. So without further ado, here is my guide for surviving a startup.

Eat well

This seems obvious, but it’s just too convenient to eat a breakfast sandwich every morning or grab a slice of pizza for lunch. I’ve noticed over time that if I eat crap, I feel like crap, think like crap, and my long term performance suffers. Food is fuel for your mind, and your brain requires premium when founding a startup.

Recently I’ve been learning to prepare cheap, healthy meals and cook them myself. Instead of a breakfast sandwich, I wake up 20 minutes early and cook a well-balanced breakfast full of vegetables, eggs, and beans.

Cooking and eating breakfast while thinking about my day has become a morning ritual and a time for deep thought away from the distractions of the day. If I don’t have time in the morning to cook, I’ll eat cereal rich in fiber like steel-cut oats or Kashi Go Lean Crunch.

The other benefit of preparing your own breakfast instead of picking up a bagel or sandwich is that you’ll save money. A typical week’s worth of breakfast supplies consists of a carton of eggs ($2.99), 2 bags of vegetables (2 x $2.99), 2 lbs dried beans ($3.99). That is breakfast for $1.85/day, or less than the cost of a bagel.

For lunch and dinner, I try to stick to meals low in carbs and fats. My favorites are turkey chili, fajitas, and stir fry, along with lots of beans (and occasionally rice). If I’m strapped for time, I’ll use a slow cooker on Sunday to make enough chili for week. The slow cooker is your best friend as it only take a few minutes to throw the ingredients into the pot, and then does all the work of cooking a delicious meal. Preparing meals in mass will also relieve you of the daily mental overhead of figuring out what to eat.


Whether you’re nocturnal or diurnal, sleep at least 6.5 hours a night. Studies show that people who sleep between 6.5 and 7.5 hours a night live the longest. When you are well rested, you’ll also make better decisions and be more pleasant to work with.

I’ve personally found it helpful to unplug from all technology for at least 30 minutes before going to bed. I’ll either read, play guitar, brainstorm a to-do list for the next day, or anything else that keeps me away from my television, laptop, or phone.

I’ve also had success setting a weekly alarm which I’m not allowed to adjust in response to how late I went to bed. If I don’t get my 6.5 hours, I’ll be punished the next day. Remembering how awful I feel on a low amount of sleep is a good motivator for going to bed at a reasonable time.


If you’re a startup founder, there’s a good chance you are not earning a market salary or any salary at all. Unnecessary stressed caused by a low bank balance is avoidable. Learn to budget your expenses and stick to it.

I keep an Excel sheet where I enter in every transaction at the end of the day. You can also use Mint or Simple to track your expenses. Personally, the knowledge that I will have to enter in an expenditure later often forces me to reconsider making an impulse purchase. I also notice patterns when entering the data, like spending money on coffee every morning when I could easily brew it at home. $3/day x 5 days a week x 50 weeks = $750 in savings/year (excluding the expense of ingredients).


Admittedly I am no where near as religious as I would like to be about exercising. I haven’t figured out a daily routine yet that works. I did have minor success with exercising during the morning and am slowly working to rebuild that routine. I personally cannot save exercise for after work because I usually have something else pulling at my time (unfinished code, drinks with the team, dinners, events, etc). In the morning I have no excuse to not exercise except that I was too lazy to wake up and walk to the gym or go for a jog.

Starting small here is important. If you make it a goal to just put your workout clothes on, chances are once you’re dressed, you’ll be able to muster up the energy to hit the pavement or the gym.

Paul Graham says you should only do three things during YC – talk to customers, build product, and exercise. After a run, I also feel invigorated and good about myself, even if I’ve had a terrible day. Exercise is like a reset switch for your brain, and the endorphin production and physical exertion will help you level out the ups and downs of startup life.

Always be learning

Lately I’ve been trying to spend a few hours a week trying out new technologies. I head to the coffee shop for an hour or two on Saturday and try to hack on a fun project to learn something new. In a startup, you’re optimizing to get code implemented fast, and taking time to learn a new technology is not considered an optimal use of time.

In order to keep my skills sharp and my sense of curiosity in tact, I try out a new technology here and there. It usually doesn’t result in anything usable, but the learning does usually make it’s way back into my startup’s product.

Spend 30 minutes a day in the sun

Vitamin D increases weight loss, helps fight depression, strengthen’s your immune system and promotes bone development. The easiest way to get vitamin D is to spend time in the sun. Spending time in the sun also helps fight off seasonal affective disorder during the winter months.

I’ve found it best to combine spending time in the sun with another activity like reading, meditating, writing or exercising.

If you can’t make it out in the sun on a regular basis during the day, invest in a natural sunlight lamp. You’ll feel much better with simulated daylight than the fluorescent lights illuminating your office.

Read a book for 30 minutes a day

Drew Houston initially learned about startups by buying a dozen books on various topics, and reading them on top of his fraternity one summer. He then used that base knowledge to start Dropbox.

Reading is a great way to unwind from a stressful day. People are also trained not to bother you while you’re reading, so it’ll give you some quiet time without having to ask others to leave you alone and seem anti-social.

When I spend time reading, I really try to take the time to enjoy the experience. In school, reading felt like a chore to be finished as quickly as possible so I could move on to other activities. Now I try to read to learn, thinking about how the content applies to my life.

I’ve had huge success in building a reading habit by reading outside. The sun, breeze, and ambient noise really adds to the experience.

charles river boston
My favorite reading spot by the Charles River in Boston

Find a place where you can relax and unwind, and enjoy a good book.

Write 500 words a day

I try to write 500 words on whatever top-level idea is permeating though my brain when I eat my breakfast and drink my coffee. Most of my blog posts start as 500-word free-form brain dumps in Draft. When I hit my 500 words for the day, I stop writing so I don’t burn myself out and leave some writing energy left in the tank.

I’ve found that writing is an excellent way to declutter my thoughts after a stressful day. In David Allen’s book Getting Things Done, he talks about how thoughts can be considered stuff, and the way to get the clutter of stuff out of your brain is to write it down. Once you write a thought down, you are free to forget about it temporarily because you’ve outsourced the memory, allowing you to think about more pressing matters for your startup.

Not only will writing your thoughts down help you organize your mind, but clear and concise communication skills are important for success. Like all skills, communicating effectively takes practice. Spend time harnessing your thoughts about your startup into a cohesive narrative through writing.

If you really want to take it to the next level, I suggest publishing your thoughts on a blog. You will develop your personal brand, which will portray you as a thought-leader and make you a more compelling target for potential business partners or acquirers. If you really want to help your startup, you should write a blog before building your startup. The community you build around your thoughts will help you find new users for your product.

Some of my favorite entrepreneurs who have recently gained traction by blogging which they are applying to their products are Ryan Hoover, Adii Pienaar, Danielle Morrill, and Andrew Chen.

Have wins not tied to your startup

“How’s business?” This is a question my grandmother asks me every time I talk to her. My friends inevitably ask me when we catch up over beers as well. When things aren’t going well, this is a hard question to answer.

Having a startup is hard because when everything’s going poorly, it’s your fault. It is not like a regular job where you might find personal solace by blaming your boss, or your coworkers. When the answer to “how’s business” is “everything is imploding around me”, it’s easy to get discouraged.

If you tie your entire identity to your company and business is rough, you’ll feel defeated. It’s important to have wins that are not dependent on the success of your company.

Set personal goals for activities you do, such as exercising or blogging. If you have an awful week, but manage to break a 6 minute mile or publish three blog posts, you still can look back and tell yourself you’ve had a good week.

If you want to track how well you’re executing on your life goals and feel accomplished when you reach them, is an excellent app for making sure you have small wins throughout the day. Everytime I acheive a daily habit, I get to mark it as complete in Lift. It’s a small gesture, but it helps me feel a daily sense of accomplishment towards myself.

lift screenshot

3 Good Things

I realized a few months ago that I am more pessimistic than I was three years ago, probably because I’ve been beaten down by the startup trough of sorrow over and over again. The good news is, it’s possible to choose optimism, and the best technique I have found for being happier throughout the day is the “3 good things” method.

At the end of the day, recap alone or with someone else three good things that happened that day. They don’t have to be majorly awesome wins either. Hearing a new song you liked, eating a really tasty lunch, or receiving an email from a happy customer are all good things. The goal is to force yourself to remember there are positive events happening throughout your days even if things aren’t working out well with your startup.

Know you’ll face despair

The trough of sorrow is unavoidable for 99% of startups, and the ones that do seem to have everything going right have days when everything is awful behind the scenes. It’s important to remember that in a startup, you’ll have extremely crappy and depressing days, but it’s just one day and tomorrow will be better.

If you can hack your mindset to not ride the startup roller, and instead replace work/life balance with work/life harmony, you’ll be much better off. The only way to do this is to not let the lows get you too low, and not ride the highs too high.

Startups are a long-term career

The startup myth of “sprint as hard as you can for three years and then exit huge to retire rich” almost never happens. Behind almost every successful entrepreneurs are years filled with struggles, learnings, and failed attempts before finally hitting on a successful business idea.

The greatest asset your startup has is you, and it’s critical you take care of yourself to survive the startup marathon.

I hope this recap of my habits has helped a few people. It’s what I wished someone had told me when I first started and came close to burn out.

What habits work for you? Any you disagree with? Leave a comment below.