Strategic CIO // Team Building & Staffing
Commentary
11/22/2013
08:06 AM
Connect Directly
RSS
E-Mail
100%
0%

4 Reasons You Aren't An Entrepreneur

A startup survivor shares why the traits that make corporate execs successful can undo their entrepreneurial efforts.

Listen in on the hallway chatter at any major tech conference, and you'll likely hear it: The rant about the ridiculousness of a certain startup getting an unbelievable amount of venture capital. Oftentimes it’s a successful technology executive at a big company behind that rant, who then starts pitching his startup idea he's never acted upon.

Should a successful IT leader chuck it all and try the startup route? In the weird, upside-down world of startups, the very qualities that make you a top CIO or other business leader can sabotage your chances of getting a startup off the ground. Understanding the "startup brain" not only helps you make that personal career decision, it can help an IT leader who's trying to encourage more of a startup mentality inside his or her large company.

As a five-time startup veteran, I humbly offer four factors that I think help big-company executives thrive -- but that work against their startup prospects.

1. Risk-Oriented Maturity
Leading an enterprise technology team requires an exceptional level of maturity that the average entrepreneur is woefully lacking. CIOs tend to have a more sophisticated understanding of risk and know how to leverage it for gain. Bets are made carefully with much consideration, and cherished projects are killed due to lack of speedy adoption. It’s not personal, it’s just business.

[ Who's in the startup catbird seat? Read The Developer Is King, Google And Startups Say. ]

In contrast, entrepreneurs tend to have this grandiose notion that ideas can change the world. Thanks to our lack of maturity, we are willing to strike out on our own immediately. We tend, especially in the early years, to have a poor understanding of risk and what we are actually getting ourselves into. On the backend, you will often hear, “If I had known how hard this would be, I would never have started.”

2. Successfully Employed
To get to where you are now requires that you were employable from the get go -- rising through the ranks and proving yourself again and again as the “go-to” person. More importantly, you possess a significant amount of political savvy to get (and stay) where you are. It’s rare to find a successful entrepreneur who is not “colorful.” We often hail from the island of misfit toys. Behind closed doors, we laugh about how ill-suited we are for traditional corporate life and share how we got ourselves fired (for the fifth time) and knew it was time to strike out on our own. Part of the reason so many of us start businesses is that we didn’t really have a choice.

3. Power Savvy
Hierarchy makes sense to you. Thanks to your expertise and position, you hold the trump card with vendors, employees, and sometimes even with peers, as your opinion can kill another’s plans. You might wield your power sparingly, even wisely, but you are accustomed to having it, at least some of the time.

If an entrepreneur ever has the luxury of power, it's usually only very late in the startup trajectory. Entrepreneurs are in a very vulnerable position for almost the entire ride. No one is ever obligated to take our calls or help us out. A startup CEO is in a constant state trying to keep employees, clients, vendors and the board appeased. As such, there is no such thing as real positional power. If you are too proud to beg, this is not your calling.

4. Pragmatic
It’s a rare CIO who can stay in this position without showing some willingness to compromise. Pragmatism is valuable and required here. You might have power, but you know when it’s unwise to force projects and agendas.

If entrepreneurs were pragmatic, they would throw in the towel far sooner than the successful ones do. What gives most entrepreneurs their edge is a willingness to withstand discomfort and uncertainty for unreasonably long periods of time. Many refuse to compromise their vision or call it quits. We just slog it out. Ironically, it’s also why many of us never make it to the finish line, as we tend to get ourselves fired once we take on capital.

There is no such thing as a quintessential entrepreneur. We come in all stripes and flavors. And yes, some very successful former technology executives have made the leap and wowed their naysayers. And some successful entrepreneurs have transitioned into great corporate leaders. But know that the qualities that have served you so well as an executive are not qualities common in startup CEOs… and for good reason.

InformationWeek 500 companies take a practical view of even trendy tech such as cloud, big data analytics, and mobile. Read all about what they're doing in our big new special issue. Also in the InformationWeek 500 issue: A ranking of our top 250 winners; profiles of the top five companies; and 20 great ideas that you can steal. (Free registration required.)

Comment  | 
Print  | 
More Insights
Comments
Newest First  |  Oldest First  |  Threaded View
<<   <   Page 2 / 2
jfeldman
50%
50%
jfeldman,
User Rank: Strategist
11/22/2013 | 8:01:38 PM
Re: Entrepreneurial Leader Vs. Entrepreneur
Indeed.
jfeldman
IW Pick
100%
0%
jfeldman,
User Rank: Strategist
11/22/2013 | 8:00:40 PM
Re: Entrepreneurial Leader Vs. Entrepreneur
Just as there are different types of editors :) there are different types of CIOs. I've met many that are quite entrepreneurial, who frankly care more about moving the pick forward for the organization -- and, incidentally, their careers -- than about job security. There's also the Maintenance CIO and lots of other types with at least 50 shades of gray. ;) My point: It's not a yes/no equation.
ChrisMurphy
100%
0%
ChrisMurphy,
User Rank: Author
11/22/2013 | 6:53:31 PM
Re: Entrepreneurial Leader Vs. Entrepreneur
Having worked in an emerging company and more established ones, the biggest difference I find is the depth and variety of resources -- colleagues -- I have to draw on at a larger, more established company.
Brian.Dean
50%
50%
Brian.Dean,
User Rank: Ninja
11/22/2013 | 2:53:10 PM
Re: Pragmatism
Yes at times it is hard to let go a bit, after all if someone has invested 17500+ hours into a startup (then definitely it has grown), has also made others invest an equal amount of time and is fond of micro management then they will be layers and layers of reasoning why a certain process is conducted in a certain way. It becomes easy as well when the startup realizes that in order to sustain growth it is equally important to let go a bit, provide that full communication with the person who is going to take over the task understands the layers of complications involved, next if they want to make changes -- it won't be worrisome. 
Brian.Dean
50%
50%
Brian.Dean,
User Rank: Ninja
11/22/2013 | 2:23:06 PM
Re: Entrepreneurial Leader Vs. Entrepreneur
Yes I completely agree, I think firstly, a CEO should not be telling a CIO to "let's out-source IT" or "let's do one of those SDN things" as the CIO should be coming up with all of these ideas themselves because at the end of the day if the business next door is more efficient and is out competing the firm, and ideas are not flowing then the game is already over. If the CIO is not wanting to lose some of their employees because they want to provide them with job security, then again I think the CIO is causing more harm than gain to the employees as wages in an IT department should be theoretically lower then wages in a specialized Cloud firm (for the same skill sets). 

 
sfreeves
100%
0%
sfreeves,
User Rank: Apprentice
11/22/2013 | 11:28:13 AM
Mentality
These are great insights!  I also feel that working for a company changes the way you think.  Most companies have templates, standards, and ways of doing things that are towards there brand.  When you are an entrepreneur you use your own thoughts, have your own brand, you are your own boss.  Corporate world conforms you to a certain way, a certain mentality that maybe certain people can't break after years of it but wish they could so hold envy towards those entrepreneurs.
Alison Diana
100%
0%
Alison Diana,
User Rank: Moderator
11/22/2013 | 10:34:52 AM
Re: Pragmatism
I wonder if it's hard to let go, to delegate, when you're dealing with your startup? After all, this is an idea you've probably nurtured for years, poured sweat and blood equity into, and worked countless 100+ hour weeks over. Must be challenging to overcome that "I can do it better myself" mentality.
RobPreston
100%
0%
RobPreston,
User Rank: Author
11/22/2013 | 9:47:38 AM
Re: Entrepreneurial Leader Vs. Entrepreneur
I think lots of CIOs are being ASKED to become more entrepreneurial, but when push comes to shove their overseers are as risk averse as they are. 
Shane M. O'Neill
100%
0%
Shane M. O'Neill,
User Rank: Author
11/22/2013 | 9:31:52 AM
Pragmatism
Being pragmatic (choosing your battles, compromising to get a project done) is essential to survival at the corporate executive ranks. I understand that being pragmatic can kill a startup's chance of acheiving that great innovative breakthrough. But successful startup enterpreneurs tell us: do you need to become more pragmatic (with staff, partners, customers, funders) once real money rolls in and you hire more people?
Laurianne
50%
50%
Laurianne,
User Rank: Author
11/22/2013 | 8:46:46 AM
Entrepreneurial Leader Vs. Entrepreneur
Interesting food for thought, given that many IT leaders are being asked to be more entrepreneurial within their own businesses -- innovate new lines of business, new communication routes with customers, new data-driven process changes, etc.

Can Kelly or others speak to the differences between running a startup and becoming an entreprenurial success inside a company?
<<   <   Page 2 / 2
2014 US Salary Survey: 10 Stats
2014 US Salary Survey: 10 Stats
InformationWeek surveyed 11,662 IT pros across 30 industries about their pay, benefits, job satisfaction, outsourcing, and more. Some of the results will surprise you.
Register for InformationWeek Newsletters
White Papers
Current Issue
Flash Poll
Video
Slideshows
Twitter Feed
InformationWeek Radio
Archived InformationWeek Radio
Join InformationWeek’s Lorna Garey and Mike Healey, president of Yeoman Technology Group, an engineering and research firm focused on maximizing technology investments, to discuss the right way to go digital.
Live Streaming Video
Everything You've Been Told About Mobility Is Wrong
Attend this video symposium with Sean Wisdom, Global Director of Mobility Solutions, and learn about how you can harness powerful new products to mobilize your business potential.