Advice For Emerging Entrepreneurs (And Anyone Else With A Boss)

Fat Cat"By working faithfully eight hours a day, you may eventually get to be a boss and work twelve hours a day."
Robert Frost, American Poet

My entrepreneurial students at the University of California, Santa Barbara, often ask my advice regarding their career choices. However, rather than discussing specific opportunities, I find that I often spend most of my time sharing general tips related to their professional success, irrespective of their particular career paths.

Although my advice is geared to recent college graduates, it is also applicable to anyone with a boss, irrespective of their age and experience level.

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Advice For Emerging Entrepreneurs

Make Mistakes On Someone Else's Dime – My students are sometimes surprised that I advise them to first work in an industry in which they have an interest, rather than starting a company right out of school. I advise them to work for smart, successful teams that will share their knowledge. In addition to giving their employers 110% of their energy, I encourage these emerging entrepreneurs to engage in small, Mini-ventures on the side, rather than starting a fulltime venture from scratch.

If You Have A Problem With Your Boss, You Have A Problem – Read the prior statement again. If you are having issues with your boss, it is your problem, not theirs. You can either work to resolve the issue or move on in your career. Assuming your boss will accommodate you is an unrealistic, losing strategy.

Make Your Boss's Life Easier – The key to succeeding at any enterprise is to make life better for your boss. This does not entail brown nosing or acting as a sycophant. Rather, it involves taking on responsibilities that will allow your boss to work on initiatives with the highest impact. This tactic is especially relevant at a startup, where everyone must wear multiple hats.

Find A Culture That Will Allow You To Fail – As described in Core Values, a sign of a healthy culture is when new employees are given as much responsibility as they can handle. When they slip up, they are not reprimanded. Rather, they are encouraged to perform a post mortem analysis and learn from the situation. Remember, people who never make mistakes, never do anything – startups cannot afford such “prefect” people.

Never Negatively Surprise Your Boss – If you anticipate that a project will be completed late, that a sale will not close within the forecasted period or that a project is running over budget, tell your boss immediately. The sooner you address such issues, the higher the likelihood that countervailing measures can be taken. Negative surprises reflect poorly on your boss. Do everything within reason to avoid such embarrassments.

Do Not Worry About What You Will Earn – Whenever you are starting a new career (no matter your age or working history), your most important consideration should be, "How much will I learn?", not “How much will I earn?” As discussed more fully in Decision Making 101, your first priority should be gaining knowledge upon which you can build a long-term career, not securing a certain title or other resume-oriented considerations. Thus, seek a boss who is willing to teach you, rather than simply direct you.

Internalize Failure, Externalize Success – As noted in Maximize Your Startup Experiences, when you fail, do not blame others. Instead, use the opportunity as chance to determine what you can do differently in the future to avoid a similar outcome. When you succeed, share the success with those around you by giving them public attribution of their involvement. As few successes are achieved by just one person, finding others whom you can genuinely acknowledge will not be difficult.

Don’t Let The Ball Hit The Sand – Each department has their “day in the sun.” In a company’s early days, it is often the developers and product marketing team who must create the product. Later it is the salespeople who must generate revenue from the product. As a company continues to mature, the customer support and professional services teams become vital in order to retain customers and the accounting department has to properly manage the company’s cash flows.

As described in Beach Volleyball, startups cannot afford to allow the ball to hit the sand. Thus, to the extent practical with your core responsibilities, pursue opportunities which assist whichever department is performing mission critical objectives. Assist as many bosses as you can, while retaining your own boss’s productivity as your top priority.

In my review of Guy Kawasaki's book Enchantment, I highlight a chapter entitled, “How To Enchant Your Boss” in which Guy encourages his readers to:

  • Make Their Boss Look Good
  • Drop Everything And Do What Their Boss Asks
  • Underpromise, Overdeliver
  • Prototype Their Work
  • Show And Broadcast Progress
  • Form Friendships
  • Ask For Mentoring
  • Deliver Bad News Early

Monkey See

The primary reason I implore my students to work for a team of successful entrepreneurs, before starting their own venture, is so they can first learn how to be a great boss. As Robert Frost notes, if you work hard enough, you might one day find yourself a hard working boss. Yet, no one works harder than when they are their own boss. As such, if becoming your own boss is your goal, you will be well served to learn how to be good at it.

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John Greathouse is a Partner at Rincon Venture Partners, a venture capital firm investing in early stage, web-based businesses. Previously, John co-founded RevUpNet, a performance-based online marketing agency sold to Coull. During the prior twenty years, he held senior executive positions with several successful startups, spearheading transactions that generated more than $350 million of shareholder value, including an IPO and a multi-hundred-million-dollar acquisition.

John is a CPA and holds an M.B.A. from the Wharton School. He is a member of the University of California at Santa Barbara's Faculty where he teaches several entrepreneurial courses.


Note: All of my advice in this blog is that of a layman. I am not a lawyer and I never played one on TV. You should always assess the veracity of any third-party advice that might have far-reaching implications (be it legal, accounting, personnel, tax or otherwise) with your trusted professional of choice.





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