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Independence - Ruby FTW 2014

Independence - Ruby FTW 2014

A lighthearted take on the pendulum swinging back and forth between idealistic hopes and dreams and the slightly-less-amazing events from reality when building a small business as a sole founder.

Garrett Dimon

May 12, 2014
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  1. “INDEPENDENCE”
    Making a living selling your own software.
    What I’ve learned from 6 years of building
    a pro
    fi
    table web application.

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  2. Hours Worked
    Income
    NOT IDEAL
    Income tied to hours worked.

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  3. Hours Worked
    Income
    IDEAL
    Income independent of
    hours worked.

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  4. 2000 2014
    2007
    FULL TIME
    FREELANCE

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  5. c
    c
    c
    Hope:
    c
    c
    c
    MONEY
    “I’m going to be
    fi
    lthy rich.”

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  6. Fear:
    MONEY
    “I’m going to be
    fi
    lthy rich.”


    “I’m guaranteed to bankrupt my family.”


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  7. Reality:
    YES
    Balance optimism and caution. Build up a
    cushion. Don’t quit your job on a whim. Prepare
    ahead of time. Don’t rush it.

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  8. c
    c
    c
    Hope:
    c
    c
    c
    GROWTH
    “I’ll just post to (insert popular web site here),
    and it will go viral.”

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  9. Reality:
    NOPE
    Slow and steady linear growth is the standard. It
    sounds boring, but it’s sustainable and reliable.
    (It’s also much more likely than viral growth.)

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  10. Example:
    CONSTANT CONTACT
    How to Negotiate the Long


    Slow SaaS Ramp of Death
    http://businessofsoftware.org/2013/02/gail-goodman-constant-contact-how-to-negotiate-the-long-slow-saas-ramp-of-death/

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  11. Fear:
    LEGAL
    “My company will sue/
    fi
    re me if I work on side
    projects.”

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  12. Reality:
    NOPE
    Unless you’re
    fi
    ling directly competitive patents,
    you’re probably OK. If you work for a particularly
    vindictive boss or company, this may be worth
    thinking about. Otherwise, your current company
    probably doesn’t care what you do at all.

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  13. c
    c
    c
    Hope:
    c
    c
    c
    FUN!
    “I’m going to write software all day!”

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  14. Reality:
    KIND OF
    Fraud. Spam
    fi
    lters. Spam accounts. Hackers.
    Chargebacks. Server upgrades. Security updates.
    Support. Marketing. Taxes. Legal. Testing.

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  15. c
    c
    c
    Hope:
    c
    c
    c
    NO MARKETING NECESSARY
    “Great products don’t need marketing.”

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  16. -
    Marketing is a tax you pay for
    being unremarkable.”
    Robert Stephens, Founder of Geek Squad

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  17. Reality:
    REMARKABLE IS TOUGH
    It’s virtually impossible to be “remarkable” when
    you launch. It’s a poisonous expectation to place
    on you and your team.

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  18. Reality:
    MARKETING CAN HELP
    The idea that your idea and execution have to be
    amazing enough that you don’t need marketing
    is poisonous. Marketing, when applied wisely, can
    make a di
    ff
    erence.

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  19. Example:
    EVERYWHERE
    Apple. Samsung. Windows. Amazon. Google. The
    de
    fi
    nition of “remarkable” is both subjective and
    constantly evolving, but these companies are
    remarkable and spend a lot on advertising.

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  20. c
    c
    c
    Hope:
    c
    c
    c
    NO BOSS
    “I won’t have to take orders from anyone.”

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  21. Reality:
    MORE BOSSES
    Instead of reporting to 1 or 2 bosses, you report
    to hundreds or thousands of customers with
    frequently divergent needs and priorities.

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  22. c
    c
    c
    Hope:
    c
    c
    c
    NO CONSTRAINTS
    “I can invest time on fun things instead of
    rushing half-baked ideas assigned to me by
    pointy-haired bosses and clients.”

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  23. Reality:
    MORE CONSTRAINTS
    Bills. Employees. Revenue. Accessibility. Security.
    Front-end. Back-end. Server. Marketing. Once
    you view everything holistically, you recognize
    the importance of tradeo
    ff
    s.

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  24. Fear:
    TEAM
    “I need co-founders.”

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  25. c
    c
    c
    Hope:
    c
    c
    c
    TEAM
    “I can do this all by myself.”

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  26. Reality:
    YES
    Pros and cons to both co-founders and going
    solo. There isn’t a right or wrong. Only what’s
    best for you in the here and now. Don’t be
    overcon
    fi
    dent about going solo, but don’t let the
    lack of a co-founder stand in the way.

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  27. Fear:
    COMPETITION
    “There’s 100 alternatives. I can’t compete.”

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  28. Reality:
    FRAGMENTATION & VALIDATION
    Be smart and di
    ff
    erentiate.

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  29. A) Email Integration


    B) Attachments


    C) Search


    D) API


    E) Milestones


    F) OpenID


    G) Text Formatting
    None of


    them

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  30. Example:
    BUG TRACKING
    45 options listed on Wikipedia. Many of which
    are open source and/or free. Probably just as
    many that aren’t listed. Do your own thing, and
    don’t worry about “competition.”

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  31. Example:
    ACCOUNTING
    Quickbooks vs. Less Accounting. Quickbooks is a
    borderline industry standard. Yet Less
    Accounting is still a pro
    fi
    table and healthy
    company.

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  32. -
    We’re the cockroach of the
    accounting software industry.”
    Allan Branch, Co-founder of LessAccounting

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  33. Fear:
    BIGGER TEAMS
    “Our small team can’t possibly compete against a
    team of 20.”

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  34. Reality:
    AGILITY
    Have you ever watched a team of 20+ try to get
    something done? You’re faster than they are.

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  35. Example:
    EVERY SUCCESSFUL TEAM EVER
    Google. Facebook. Apple. Twitter. They didn’t
    start with 20 people. Everything was a side
    project at one point.

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  36. Fear:
    HEALTH
    “I can’t a
    ff
    ord health insurance.”


    “What if something happens to me?”

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  37. Reality:
    MIXED
    There are very legitimate health reasons not to
    start a business. Hypothetical reasons, however,
    are not among them.

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  38. Example:
    MY FOOT
    Lost about 6 of the last 12 months to being in
    bed, on pain killers, or in the hospital. Being self-
    employed actually made the situation tolerable.
    Recurring revenue ensured no negative a
    ff
    ect on
    our income.

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  39. c
    c
    c
    Hope:
    c
    c
    c
    FREEDOM
    “No meetings or interruptions, and I’ll work from
    the beach all of the time!”

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  40. Reality:
    FLEXIBILITY
    Work when you want. How you want. Where you
    want. (Most of the time.)

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  41. Example:
    MY FOOT
    I got to work from a hospital bed.

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  42. Non-example:
    CONNECTIVITY
    Hosted software needs to be available 24x7.
    (More or less.) If you like to get o
    ff
    the grid,
    ignore what I said about co-founders. You’ll want
    one.

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  43. Fear:
    KNOWLEDGE
    “I don’t have enough experience yet.”

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  44. Reality:
    YOU NEVER WILL
    The only way to learn is by doing. Running an
    app is nothing like running one for a corporation.
    You have to become a generalist, and most
    corporate jobs just don’t enable that.

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