The Entrepreneur’s Employment Dilemma

Tim Ferriss preaches time efficiency and immediate retirement through regimented workflow. His ideas to create residual income built from self-sustained online ordering services have inspired countless online marketers.

For entrepreneurs who intend to build businesses scalable to the world, this is a fanciful system for passive earnings and leisure. Also, for entrepreneurs like me, passivity and lax lifestyle is not desirable in early professionalism. We are bundled with energy and intend to apply it toward changing the world, building worldly enterprise and substantially increasing earnings.

While living in contrast to the 4 Hour Work Week credos, what does an entrepreneur do before their billion dollar business is born?

We reluctantly enter the workforce.

Fortunately, there are startups that merit our time, energy and management skills. There are communities of enterprise, whether in incubation or growth stage, that can focus our attention and provide platforms to apply ingenuity.

After joining an inspiring startup, I reflected on pressing questions.

Are entrepreneurs damned to experience disinterest within companies that are not our own?

Are we predisposed to cause disruption due to our desire to enterprise constantly?

Are we unfit to follow a track of systemized pay raises and systemic internal politics for another’s company?

The answer to these personally afflicting questions is definitively and surprisingly, ‘yes’. However, there’s hope. The market of jobs is more accommodating to endeavor-bound entrepreneurs than most realize. Some companies are actively solving problems in fragmented markets with technology, and collaborative consumption models like TaskRabbit and Car2go. These startups specifically cater to entrepreneurial idiosyncrasies.

For entrepreneurs who need immediate income, time to develop their idea or private sector experience, these circumstantial demands are not a death warrant to your business growth. There are strategic and innovative methods for entering traditional workforce roles that provide long-term entrepreneurial empowerment.

Let’s discuss how…

Method 1: Include your employer in your long-term or near-term goals.

Firstly, meet the CEOs or HR decision makers from startups in which you want to work. Attend the conferences they attend, participate in the panels on which they sit and organize casual events where they would guest visit.

From the start, demonstrate your value offering to them and be transparent about your long-term goals. Your ambitions and thought leadership likely make your prospective employment more attractive than a non-driven, subordinate thinker.

A company like, which offers online sign orders, has a specific department for entrepreneurs. There, they give leadership responsibilities, budget oversight and creative room for entrepreneurs to work for a small chapter of their professional life. They are mentored when needed, given intelligent staff and provided other crucial amenity assets to work comfortably and innovate.

Method 2: Negotiate like the godfather – provide an offer they can’t refuse.

Many startups are limited with the amount of funds they can deploy to new hires (depending on investor restrictions). Understanding these constraints through basic research will earn confidence from your negotiation partner. They must view your salary demands as reasonable, so offer them an understanding of their market growth potential relative to their current earnings and investment injections.

Often, startups will propose a vesting offer, which means salary will increase after a certain time period or demonstration of work ethic. This is acceptable, but get your income terms in writing. Declining equity may give you better salary options.

Vesting options for salary and equity create contracted time periods of employment, which may be desirable for entrepreneurs capable of enterprising alone. Therefore, specify the preferred time frame and make an attractive value offering with benefit to all parties. Don’t trust agreements outside of writing, no matter how much the other party espouses ethics or integrity.

Finally, don’t settle for compensation unfit for your baseline needs.

Be willing to walk away if necessary.

Method 3: Bust your ass, be yourself and save.

Never fear unemployment. Quit if the environment is toxic or damaging, but never do so if it’s difficult. Challenges are healthy and absolutely necessary for entrepreneurial growth. Plow through obstacles and always respect your colleagues, no matter how threatened or surprised they are by your entrepreneurial eccentricities.

Pretend as though the company is your own regarding passion and work ethic, no matter what the job description. Grind out long hours and demonstrate humility when learning and growing on the job. This will expose you to situations and information that builds helpful reference knowledge. Balance your personal life with healthy habits and protect your sleep schedule.

Privately designate a calendar date for leaving the job, and accompany this date with a financial savings goal. This will give you the cushion necessary to leave employment and begin building your company.

Finally, live, “on the bone.” Join a cooperative with an open kitchen, utilize public transportation and buy used books. Do whatever necessary without compromising health and personal safety.

Saving is paramount to boot-strapping a startup of your own.

Entrepreneurs too often decry or avoid institutions that can empower them.

Examples are universities and companies other than their own. Universities like New York University, Columbia and Stanford have their own incubators and startup communities that can propel an entrepreneur. Many large companies, like BMW, have established incubators to develop new ideas and invest in new technology.

Reticence toward large, seemingly archaic institutions is well placed, as most entrepreneurs believe subordinate roles will stifle and hinder creativity and limit time. However, without financial life supporters or seed investors fueling the early-stage of a company, employment is useful and strategic, if not outright critical.

Transparency during your networking pitches to startup leaders, reasonable salary negotiations and responsible savings will enable future endeavors.

Work hard, spend frugally and aspire with discipline. In time, your opportunity to relentlessly build and passionately lead a company will arise.

Until then, do the same in another company and inch closer to success every day.

Go forth and earn.