My First Job: Will (Happily) Work for Free

Week 1, at an after hours casual event. 6/93. Me, Bob White, & my girlfriend (now wife!) Alli.

I have enjoyed the good fortune of working with dozens of amazing executive teams and directly hiring hundreds of people as a founder, CEO, investor, board member, and now partner at Bessemer Venture Partners. Ironically, one of the best long-term career decisions I ever made was leaving my paid job years ago and accepting an unpaid internship to get my first real exposure to a great office environment.

After spending my high school years doing a mix of labor intensive jobs including landscaping, retail, and construction, I was about to complete my Freshman year at Cal and aspired to be more than a hired "grunt." However, I quickly realized that my lack of professional experience made it prohibitive to get a highly respected office job and get paid well for it. So instead, I bit the bullet and consciously took a step backward by giving up a paycheck, and offered myself as an unpaid intern to more than a dozen companies and offices. Due to some good advice and great fortune, I ultimately accepted a position as the intern to Bob White, the Chief of Staff to the Governor of California.

At age 18, I founded myself sitting inside the highly secure “horseshoe” of the California state capitol building, at a small desk directly between the open offices of the Governor of California and his Chief of Staff. At the time California was rated the 7 largest economy in the world (ahead of countries like China, Spain, & Brazil!), in the middle of a massive budget crisis, and the Governor himself was in a nasty re-election campaign where he trailed a popular challenger by 13 points. I dropped into the heart of a storm, and absolutely loved it! I ultimately worked for Bob in different capacities for four years, where he proved to be a fantastic boss, career mentor, and in many ways, a second father.

From the long list of things I learned by quietly watching our top elected officials in California come through my office, there are four key lessons that I’ve applied to every job I have had since:

1) Work for free at the job you want until they have no choice but to pay you for it, or promote you into it.

You will generate a very high rate of return on your time, if you invest time early and wisely in your own career advancement. I viewed my investment of months into my first unpaid internship, much as I did college itself. It was a path to a better job and the start of a professional career, so I “invested” every extra hour into my internship. I was fortunate as a student to have a very low expense base and generous support from my family for my key expenses, so I was able to commit to the internship full time, but part time internships can be equally powerful. I absolutely loved the people and intellectual stimulation of the capitol job, and carved out time in evenings, weekends, and every academic break to be with them in the office. Eventually they broke with tradition and offered me a paid position for the following summers to work with them full time.

It’s much easier and lower risk for your boss to promote you into a new role if they’ve already seen you performing some of the functions already. If you are an online marketing manager and want to be a Director of Marketing, volunteer to lead some projects in the other areas of marketing. If you’re an engineer and want to manage a team, then look for opportunities to manage a project or service providers to learn the skills. If you’re a sales development rep and want to be promoted into owning a sales quota, take the time to learn your product and shadow some sales reps so that you’re ready when called upon.

2) Proximity to great people matters more than just about anything else, including title and short term compensation.

I have repeatedly focused my career decisions around the opportunity to work with great people in great organizations, often at the expense of short term compensation or title, and continue to believe it’s the right tradeoff. I accepted the internship in Sacramento over my other opportunities, because it was a chance to work directly with Bob White in a well-regarded administration. Sure I spent most of my time answering phones, driving around dignitaries, and working on minor projects, but I was able to be coached and mentored by the operating executive running the state of California, who proved to be a master of people and relationships. Just watching him operate, and passively listening to discussions between him and the Governor, Senators, and other dignitaries, was like a Masters’ program in office protocol, organizational design, politics, management, and negotiations rolled into one.

In fact, years later, as a young founding CEO of Trigo, I even made the decision to bring in an outside CEO in Tom Reilly so that the entire company would benefit from adding a great leader and mentor. When friends ask me for career advice, I encourage them to focus on “team first” when deciding on companies to join. Similarly, we overweight founding teams at BVP when making investment decisions. Simply put, try to pick world class mentors and work hard from them, and you will benefit tremendously from the opportunity to learn from the best.

3) Don’t abuse your moments of leverage or be a jerk.

This one should be easy, but is shockingly hard for alpha males in particular to implement in practice. There are dozens of moments of leverage large and small throughout any normal business week. They can be extremely broad mandates, such as a Governor being re-elected by a wide margin, to the little things, like helping a colleague in a moment of crisis or catching errors in a business deal that the other party missed. In just my first year of working in the Governor’s office, I saw the political tide reverse entirely from a massive underdog position, to a sweeping reelection by a wide margin and extremely favorable public opinion polls. This administration was not vindictive, but it would have been very easy to punish those who abused power the prior year. Instead, they used the change in fortunes as an opportunity to build positive relationships within both political parties for the longer term. Similarly, you can form very tight professional bonds by helping colleagues through challenges, or doing right by your business partners, even when not it’s not required.

Academic business theory says that you should act differently in one-off negotiations versus repeat, long term negotiations. I agree with this, but only because I define almost every negotiation and relationship as long term. Resist the temptation to spike the football in front of your advisories and colleagues, don’t be a jerk and gloat when things happen to go your way, and don’t put the screws to people so much that there is nothing left for them in the end.

4) Always be slightly more formal and prepared than your boss.

This sounds silly, but in both the Governor’s office and my first company, different senior executives pulled me aside and coached me to “up my game” at key points, and I always appreciated the candor. Don’t let minor things like personal appearance or style limit your personal impact. Always dress slightly nicer than your boss, always try to arrive a few minutes early to meetings and be available afterwards. If you’re the junior person in a meeting, prepare extra well before hand, take notes, and avoid the temptation to check your email. Never make your professionalism a question in your boss’ mind. You want him or her to always feel comfortable including you in important meetings and proud to have you as a surrogate.

In the true spirit of “dress for the job you want, not the one you have”, I put on a suit an tie, in 105 degree Sacramento heat, to go to my unpaid internship every day. Even now, despite wearing jeans to work most days in our casual office, I still keep a blazer hung in the corner in case one our limited partners (my boss!) happens to drop by to meet. It’s the same reason why a Silicon Valley CEO may have a tee shirt culture in the office, but wear a suit on the IPO roadshow.

As a parting thought as you consider career moves, always follow your passions and try to have fun along the way. I wish you the best as your career evolves, and hope you’ll consider hiring me someday if this great venture gig doesn’t work!