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The Intrapreneur’s Dilemma

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Should you leave to start your company or do it through your current job?

Antique wood paneling. Posters with quotable one-liners about failure. Table after table of bright-eyed entrepreneurs working on their pitches. And of course, beer. Lots and lots of beer.

In 2013, I traded the polished midtown office of my consulting firm for a co-working office in downtown NYC that had all the features you would expect when you hear a word like “co-working”. I was helping my company launch a new startup, and we had decided to move out of our company headquarters and into this space to really feel like a young company. We wanted to borrow more than just kegs and quirky murals – we wanted to thrive off the NYC startup ecosystem that was beginning to emerge at the time. Our intent was to feel connected yet distant, small yet well-resourced, supported yet avant-garde.

“Intrapreneurship” at its finest.

Yet when I made the decision to help launch a startup within my firm instead of leaving to start something outside, I felt like I had failed some golden test of entrepreneurship. Could I really consider myself one of those risk-loving, battle-ready entrepreneurs I had heard so much about, if I was too scared to give up a steady paycheck?

Maybe. My time spent as an intrapreneur, where I worked with colleagues we recruited from smaller, more traditional start-ups, taught me that intrapreneurship is sometimes a valid, even preferable, alternative to full-blown entrepreneurship.

Building an organization within your company is different from building one outside, because of the brand, products, people, norms and mission already in place. Here are some things to consider when debating which to do.


Do you just want to test the waters?

You don’t need to cannonball right into the deep end of the pool, where the water is cold, unfriendly, and lacks health insurance. You may be paying back student loans, starting a family, or up for a promotion – there are tons of reasons why now is not the right time to quit and start your own company. Which is FINE. It’s OK to dip your toes in first – it’s what I did in 2013, and it’s not stopping me from diving deeper two years later.  For others it may never be the right time to take the plunge – staying in the shallow end of the pool by becoming an intrapreneur can be just as rewarding.

Is there something you love about your current company that would be hard to recreate elsewhere?

Brand. Culture. Mission. Your current company has taken years, if not decades, to fine-tune and cement many of the things you would have to re-design from scratch. Compared to products, customers, and even people, these things are hard to plan in a new organization, yet hard to escape when launching a new team within an existing one. Gauge the uniqueness of these softer elements of your company and figure out how important they are to you.

Can you navigate the internal politics?

As an intrapreneur, you have to be conscious of who knows who within the company, how incentives are structured, and how your work affects (and often cannibalizes) other business lines. If you’re already well-informed and can navigate internal politics, then your company can offer you resources to help launch your startup more quickly than you could on your own. In other words – if you’re heir to the throne, why would you leave for a foreign land where you can’t access your kingdom’s resources?

Do you value the re-entry option?

In the very likely possibility that their startup doesn’t work out, intrapreneurs have an easier time transitioning back into their parent organization than do standalone entrepreneurs. If a project is labeled “skunkworks” or “experimental”, failure doesn’t have the same stigma it would have for a run-of-the-mill company project. In fact, the creativity, leadership, and problem-solving you can demonstrate while leading the initiative are highly sought after skills in any company. On the other hand, the scars you earn from trying to launch a product with few resources at your disposal may be valued more highly among the traditional startup community (e.g., VCs, other startups) than if you had done it the same within another company. You should figure out which community matters more to you.

Is it better to move slowly?

“Move fast and break things” sounds more like a tagline for Speed than a rule which all companies should follow. Not everyone can be Keanu Reeves careening through downtown LA at over 50 mph and expect to emerge unscathed – similarly, there are many situations where moving slowly (as you almost surely would as an intrapreneur) is preferable. For example, we’re not all starting tech companies where the cost of failure is a few hours of downtime. Biotech and social enterprise startups, for starters, are in industries where the cost of failure is extremely high and may only become apparent down the road – perhaps these types of startups can benefit from the processes and rigor that slow down innovation in larger companies.


If I had a nickel for how many times I’ve been told “startups are hard”, I’d have…well, probably just a few bucks. Which may be enough money to buy Joost. Or Color. Or SearchMe. Or Homejoy. Or Cuil. Or Pay By Touch. Or any of the other 90% startups that are destined to fail.

Because starting a company is hard. It’s even harder to start a successful company. So why make a scary thing like entrepreneurship a black or white, all-in or all-out issue, when there are plenty of similar alternatives?

3 thoughts on “The Intrapreneur’s Dilemma

  1. “If I had a nickel for how many times I’ve been told “startups are hard”, I’d have…well, probably just a few bucks. Which may be enough money to buy Joost. Or Color. Or SearchMe. Or Homejoy. Or Cuil. Or Pay By Touch. Or any of the other 90% startups that are destined to fail.”

    So true. I firmly believe that the startup route, as hot as it is at the moment, is truly not as glamorous as it sounds, and I say that as someone who worked in startups and still plans to! There are actually so many things that you give up, and risks that you take on, that I advise anyone who’s thinking about making the leap to ask themselves 2 questions: 1) Why do you want to work in startups? and 2) Why aren’t those things you can’t easily find anywhere else? And if you don’t choose to go to startup land, it absolutely doesn’t mean you must be a coward–you may be making what is really the smarter choice, because there are a lot of Colors and Cuils in the future.

  2. Great post Vibin. We don’t hear a lot about intrapreneurship, but I agree with you that intrapreneurship should also be considered as a valid option for those aspiring to become an entrepreneur.

    The company I worked at before HBS had an intrapreneurship program where you could launch your own start-up internally as long as the product you are proposing was within the broader boundaries of the company’s mission. Every month, there was an open pitch-off where aspiring “intrapreneurs” would propose their ideas to a large group of peers and executives who would judge and rate your idea. If selected as one of the top teams, you would have 3 months to build your proof of concept with some resource support from the company. You would then go through another pitch-off, after which if selected, receive one year of resource support (fixed amount of “investment”, space, back-office support, internal talent recruitment etc.) to fully develop the product and launch commercially. You are given a lot of independence and not really impacted by internal politics.

    Although you don’t have the equity upside of an outside start-up, this is a “safer” way to fulfill your entrepreneurial aspirations and make a difference through your vision(product).

  3. Very interesting post and great firsthand insights into the intrapreneurship model. I found your questions quite thought-provoking, and they made me wonder if there were aspects of entrepreneurship that you felt you missed out on. Or said another way, what is it that has you planning on “diving deeper two years later”. Some questions that I would have about weighing the entre- vs. intra- decision myself would be:

    – Is the organization actually committed to this new venture or am I headed down a path that is doomed to conflict with the existing business?
    – Will I be given enough autonomy to make the impact that I want to make?
    – Is the upside (from an economic, personal fulfillment, and recognition standpoint) commensurate with the effort required to make this work?
    – Will the organization value my contributions to this initiative on the same level as ‘traditional’ business employees, particularly in a downside case?

    I would be curious to hear what concerns or other questions have you moving toward going it alone?

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