Random lessons from 12 years in startups

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Random lessons from 12 years in startupsI wrote a post several weeks ago about the many lessons I’ve learned from my entrepreneurial father.  Now I would like to share some tips from experience I have gained working in a startup world for 12+ years. These are things you definitely learn from rolling up your sleeves and working, not from a classroom or a textbook.

  • Even one word in a 40-page contract can land you in a very bad situation. It does not matter how experienced or expensive your attorney is – learn how to read contracts yourself. Also, demand that your documents be written in “normal human” English because this helps both sides know what they need to do to be compliant with the contract. The language lawyers use serves only… lawyers.
  • Family-run companies are great companies… if you are member of the family. Every organization has unavoidable office politics, but in family-run companies the office politics are at a whole new level. Again, there is nothing wrong with these companies, but you will only succeed if you are also politically savvy.
  • If you hold substantial equity (read: anything more than 1/10th of the company), require to see the books at least quarterly. Learn how to read financial documents and navigate QuickBooks. Many companies go under because those, who you thought were your partners and friends, mishandled money.
  • In the startups world, those who flaunt their education or pedigree usually have nothing else to offer but their titles. I love people with proverbial dirt under their nails who were able to rise up through the ranks through their hard work. They are a very valuable asset to your company.
  • A lack of adaptability is often confused with resilience. The big difference is: resilient leaders will navigate their companies around the storm, while others will drive right into the storm exclaiming they are “trailblazing” entrepreneurs (only to run out of steam and perish).
  • Though I heavily advocate against using titles inside of the startups, if you are an employee, make sure you get one matching your contribution to the company (even if the company has a flat org-chart). All of us will move on someday and the outside world loves titles.
  • A person with a highly complex coffee order who does not tip tends to be an egocentric and vain asshole.  If you are interviewing with senior level managers or executives, try to have at least one meeting in a coffee shop or restaurant and watch how your future boss treats their hard-working barista or waiter. Bob Sutton, author of “No Asshole Rule”, would definitely agree with this statement. He calls it “Asshole Metric: The Starbucks Test”.

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  • Apollo -

    Good post with some sage advice. I would offer just a few modifications / additions.

    MOD1: I think you should get comfortable with the financials if you have ANY ownership stake, even 1%. Your residual equity value will be HIGHLY dependent on growth in financial performance and EBITDA generation of the company. Don't get confused by complex accrual based accounting treatment. Focus on how much free cash is being generated by the company and where it comes from.

    MOD2: Make sure "normal human" English does not get diluted down to "ambiguous and unenforceable" English. You need to be able to lean on this contract when and if the time comes.

    ADD1: Invest some of your own money to have a professional labor attorney review and revise your employment contract prior to signing, ensuring solid and fair change of control, termination and vesting language that protect your interests.

    ADD2: Get very knowledgeable with the investment thesis and exit timeline of your equity sponsors, angel investors or VC backers. As much as you may not believe it, your job is to help them monetize their investment in your company (while at the same time creating a great enterprise).

    ADD3: Never assume that your company or your position will exist more than 30 days into the future. Keep networking, Keep your radar up, Pay It Forward.

    Best,

    @JeffreyJDavis
    .-= Jeffrey J Davis´s last blog .. =-.
  • 1st. Honored to have you comment on my blog.
    2nd. Love it when you get deep into the issues. Definitely helps my mission of opensourcing as much knowledge as possible, so 1st time entrepreneurs would take advantage of it and make less mistakes.
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Hi, my name is Apolinaras Sinkevicius, but most call me Apollo. I am the guy who takes care of the day-to-day business and technology of rapidly growing companies. 12 years in managing the "nuts and bolts" of companies and being a steward of corporate cultures makes me a seasoned operations professional and right hand person to founders and CEOs.[read more]
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