How To Know Your Side Project Is Ready To Be A Startup

By Jason Baptiste on February 3, 2011

turn idea into startup resized 600The word startup seems to be used too loosely in this day and age. Some people think something built in a weekend or over the course of time on the side is a full fledged startup, when it is often just a side project. Building things is great, more people should do it and do it often. The problem is, most people either take the leap at the wrong time OR they don't take a leap at all, when the signs are there. I recently went through this process a few months ago myself on taking PadPressed, now Onswipe to a full time startup. Here are the 8 things that I realized, which are telltale signs that you might be ready to turn your project to a full time startup.

You’re Doing Something You Love

This is key not only early on, but for the long haul. I know it sounds cliche and you hear this from everyone, but it's one of the most true and consistent pieces of advice given out in the startup world. Startups are a marathon and even though you often hear about the good times, you will rarely hear about the difficult times. There are always more difficult times than good times. Any normal person would just give up, pack it up, and return to the real world. If you absolutely love what you do, then there is a higher motive there that will keep you going on. The work you do needs to transcend being "work" and become even more than that.

You’re Making Revenue

Getting somebody to give you their credit card and their hard earned cash is way harder than most think. For some companies it will happen easily, but for most, it just doesn't. If you start making revenue that can pay your most basic expenses, you're on the right path. The difference between zero dollars and one dollar is huge. If you have figured out how to bring your first dollar in, you might be ready to take things to the next level. If those dollars are rapidly growing, even more reason to continue onwards.

You Know The BIG Vision

This is key and often an awkward point for most aspiring entrepreneurs. It's a side project, two guys in an apartment, nights, weekends,etc., so how is it possible to imagine going from that to being a multi-billion dollar company? It just feels really weird thinking about that, right? DON'T LET IT. It's a point you can get to, but it will never happen if you don't start to formulate those thoughts. Zuck started FB at one college with one photo, but I bet you he knew exactly what it could become one day. Having a larger vision to aspire to will motivate you to accomplish something grand. It will make you feel as if you are taking on the world, which you often will be. Realize that it doesn't happen overnight, but it does happen to great companies. Here is the one question I ask all startups I meet that ask me for in-depth advice: "If you succeed to your fullest extent, how will the world be a different place in five years?"

Your Big Vision Does Not Have A Ceiling

The problem with big visions is that the excitement of this big vision can often cloud the ceiling that it may have. You have to be going after a vision in a large market that has a very high ceiling. You won't get 100% penetration or possibly anything near it, so the market has to be large enough that you can continue going forward. Niche businesses can be nice, but they often lead you down a path of boredom. You hit your peak, make your money, but soon realize there isn't much more left to be done. You do either of two things: get bored, quit, and give up OR you try a new riskier direction. The riskier direction option can work, but it means that your initial business wasn't large enough. Find the big vision within a large market that has a lot of untapped potential.

You Are Ready To Be Selfless

This is a lesson I've recently spent a lot of time thinking about. I think it's one that not enough people talk about and is the most important thing an entrepreneur can know before going full time on a startup. You have to be 100% selfless. It is no longer just about you. You are really last on the totem pole. You have responsibility to more than just yourself or another cofounder. It's such an important piece of the puzzle that it needs to be broken down into three further points below.

You Have A Responsibility To Employees

Everything you do has to have the well being and care for your employees in mind. Every decision you make will have a small impact on your life, but it will have a large impact across the lives of so many others. It might even be 5 people at first, but those 5 people have family members, kids, loved ones, and many more that depend upon them. If you make a selfish or poor decision, it will end up having an impact on a large chain of people. Expand from 5 to 50 then 500 and you are now responsible for the lives of many many people. One of the people working with us hard at Onswipe has a young kid. One night on Skype when we were announcing our plans to expand I saw their kid walk into the room. That moment forever changed my life. I realized I was now responsible for so many more people than myself. If I screw this up, it impacts so many other individuals.

You Have A Responsibility To Customers

Customers will depend on your service working in order to do business and some core functionality of what makes them tick. You need to realize that the decisions you make will have an impact on those customers and their customers. They have trusted a core piece of their business to you. The product decisions and pricing decisions often have an impact on companies. Your customers trust you to perform a function and you need to keep yourself healthy for the long haul.

You Have A Responsibility To Investors

Your investors have probably been pitched by hundreds of other entrepreneurs throughout the year. They chose you and maybe a select few others to go take on the world. You have a responsibility to do well by them. If they are angel investors, they have trusted you with the money they have earned through the same exact hard earned blood, sweat, and tears you are currently going through. If they are venture investors, their job is to pick the best of the best. They have to provide returns to their LPs and also risk their reputations on your company. Yes, many venture backed companies fail, but they will go in expecting the worst, but hope for the best.

Keep in mind, you don't need to hit all of these points. You may just be at the idea stage and be nowhere close to achieving anything listed above. That's okay as I wish I had these points when I started as an entrepreneur. The points in this essay were adapted from a talk I gave at Plusconf. I will be giving a more polished and refined version of this talk at Columbia University in New York City at 7 pm this Friday - Details:

You Should Follow me on Twitter:, Friend me on Facebook:, Email Me:, or even call: 201.305.0552

Slides From The Talk

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How To AMP Your Engineers: Ideas For Energizing Your Best

By Yoav Shapira on February 2, 2011

The following is a guest post from Yoav Shapira.  Yoav is on the management team at HubSpot and runs our platform initiative.

At HubSpot, our small internet marketing software company, a major factor in our plans for world domination is our engineering team.  We want our developers, designers, product managers, and QA engineers to all be as empowered as possible, so they can produce their best work.

This is very common, naturally.  What company wouldn't want that?  But in my experience, most companies and management teams go about this empowerment in intuitive, but wrong, ways.

The result is the usual mix of complaints: slow product development, low quality, unproductive developers, and unhappy customers.

To me, the key to this puzzle comes from two researchers, Daniel Pink and Simon Sinek.  Their research spans psychology, organizational behavior, and behavioral economics, and it answers this question pretty well.  The main finding is that we need to stop using the old "carrots" like cash bonuses.  Instead we should use approaches that increase intrinsic motivations for these creative 21st-century tasks like software product development.

Daniel Pink speaks about AMP: Autonomy, Mastery, and Purpose.speaker amplifier

Autonomy, the dictionary tells us, can be understood as "The capacity to make an informed, uncoerced decision."  Mastery is about expert skills, in-depth understanding of technologies and ideas, and continued study and practice.  Purpose is about having a shared vision throughout the organization, at every level, of why we're here as a company, and why we're doing what we're doing, in service of something larger than ourselves.

Simon Sinek touches on many of the same topics.  He positions it as three concentric cirlces: the "What?" circle, the "How?" circle inside that, and the "Why?" circle inside the "How?".  If it sounds a bit strange, watch his TED conference presentation below.

In fact, you should probably watch both of these presentations now, or after you read this blog post.  You really should.  Both are short, both are great, and both apply to your company, I promise ;)



What I wanted to share today is not theoretical, but how we are trying to apply some of the above findings to our work at HubSpot.

(1) Product development teams run like small startups.  

Each team has a product manager, who can be a classically-trained product manager or an experienced developer.  More than half our teams today are led by an experienced engineer.  Each team has a small number, 2-4 typically, of additional engineers.

Each team also has a Customer In Residence (CIR), a member of our Customer Success team who speaks to customers all day long, every single day.  Finally, We also augment the team with specialist skills, like QA engineering or design, as needed for their specific projects.

Each team owns an area of the product.  And when I say they own it, I mean they really own it.  They not only decide what to do in that area, in what priority, and how to build it, but also what metrics are the important ones for that product area, how to track those, and what the goals should be for themselves for those metrics.  We think of the product managers as mini-CEOs of their own startup -- because they basically are.

This helps establish autonomy.  Real autonomy, where they can make their own decisions, drive their own metrics, experiment as they see fit, and be accountable for the consequences.

(2) Purpose: A sounding Board for advice and coordination.

Just like our company has a Board of Directors for advice and feedback and tracking progress, our management team serves as a Board for the different product teams.  We have a monthly Board meeting where each team presents its progress on the metrics they track, analysis thereof, and plans for the next month or two.  We have an open and candid discussion about what's going on, but the team decides what to do next.

small board cartoon resized 600

(Image from The Equity Kicker.)

Also like a company Board, specific Board members work closely with the teams, each one as an advisor, and each one helping only 1-2 selected teams so they are focused.  We help them look at the metrics, keep the big picture and company vision in mind, identify opportunities for coordination with other teams, and otherwise help answer any questions they might have.

This Board helps keep a consistent message on our purpose and vision: why are we here?  Why are we doing what we're doing?  What's the greater good?

We also do other recurring activities, like a periodic all-hands company meeting (followed by a party typically), an extensive internal wiki with transparent updates from everyone in the company, starting with the CEO and going to the newest employees, a weekly internal newsletter, and more, all intended to remind us of our purpose.

(3) Opportunities for mastery are everywhere.

As Daniel Pink tells us, it's important for creative professionals, including software engineers, to get better at our craft.  Besides the actual improvements to our work products, this also gives us a good warm feeling of continuous improvement, learning, and satisfaction.

There are a variety of ways to accomplish this goal, although really this is a life-long quest, not a binary "yes / no" badge.

Things like tuition reimbursement, for example, are pretty common and we love them.  But even there, your company can differentiate itself with a creative policy.  For example, ours is roughly "no paperwork, no manager's approval, you will get reimbursed, but you have to list your name, your course with link to materials if possible, and your grade, on our internal wiki visible to all employees."

A less common thing companies do, unfortunately, but one I think they should do more, is encourage employees to contribute to open-source projects.  These can be open-source projects we use at work, things we like personally, things we created at work and now made available to the world, or some other combination.

At HubSpot, we actually go a step further and look for open-source contributors as part of our recruiting process.  We find a high correlation between intellectual curiosity, a professional drive to be a better software engineer, and contribution to open-source projects.  It's not a requirement of course, but we really like it when we find those folks.

Sometimes you get an open-source project that on its face has nothing to do with your product: Git by a Bus, recently written and open-sourced by HubSpot engineer Edmund Jorgensen, is a good example.  It's a tool to analyze source code repositories for unique knowledge held in developers' brains ;)  But even that tool, which has nothing to do with our product, is a valuable engineering management utility.

Finally, we invented a little bit of our own custom opportunity for mastery, in the form of HubSpot Fellows.  This is a program anyone here can apply to.  It's jointly led by our CEO, Brian Halligan, and a Harvard Business School professor, Andrew McAfee, we recruited for this role.  There are classes roughly every week during the academic semesters, and they cover a diverse range of topics that the management team finds relevant to our business, and/or topics requested by students in the class.

All of these things together, combined with explicit encouragement from management to engage in these activities and improve oneself, lead to an enhanced sense of mastery over time in our engineers.  Or at least, so they tell us ;)

(4) Make it personal with a mentor

As readers of this blog likely know, many engineers can be shy or timid.  They often want the above autonomy, mastery, and purpose, but are unsure about how to ask for it, how to voice complaints, or even what they really want.

I found that having a more experienced mentor you can go to from day one with any question really helps with this.  We pair people up before they join the company, even, with a more experienced engineer.  It doesn't have to be an older engineer, just someone who's been here for a while and knows the system well.

We tell our new employees about autonomy, mastery, and purpose (informally usually), and encourage them to speak with their mentors / buddies any time they have a question on any topic.  I hope they specifically push their mentors on these topics in particular.

The mentorship is a stable, long-lasting relationship, hopefully.  It spans projects, team changes, and more.

(5) As with everything else, know that you're imperfect.

We know we're not going to get this all right in the near future.  There is plenty of room for improvement, and plenty of opportunities for us to make mistakes.  The good thing is we recognize that, and we try not to be arrogant.  We ask for feedback from everyone all the time, and (gasp!) we often listen and act on it.

Many of the programs above did not exist when we started the company.  They have evolved over time in response to feedback, both quantitative and qualitative, from employees primarily, but also from advisors and other "friends and family of HubSpot" people.

We'd love to have your feedback, so we can improve our programs even more.  What do you do to encourage autonomy, mastery, and purpose on your engineering team?

By the way, if you or someone you know is an awesome developer, you might want to check out what HubSpot is doing to win the battle for technology talent in Boston [there's a $10,000 bonus involved].

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