What do you want to achieve in the next 5 years? Five years can seem like a long time if you have a plan and you know what you want to achieve, but without a plan, 5 years can pass by very quickly. Here's how to get the most out of the next 5 years from Dave Kellogg, consultant, independent director, advisor, and blogger focused on enterprise software startups.

1. How to Get the Most out of the
Next 5 Years
Dave Kellogg
Advisor, Independent Director, Consultant, Blogger
www.Kellblog.com
9/25/19, r1.4
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2. My Background
• Computer club (middle school)
• Berkeley: geophysics and applied math
• Ingres: support  competitive  prodmkt
• Versant: battlefield promotion to marketing VP
• BusinessObjects: CMO from $30M to $1B
• MarkLogic: CEO from $0 to $80M
• Host Analytics: CEO from <$10M to $50M (sold)
• Boards: Alation, Nuxeo, Profisee, Aster (sold),
Granular (sold)
• Today: consultant, independent director, blogger
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3. The Best Thing That Ever Happened to Me
• Result of international treaty called a Totalization agreement
• Can live up to 5 years in France under US social security
• Was living in France, as CMO of BusinessObjects
• Coming up on five-year mark on 7/1/2001; needed to move home
• Liquidated large stock position between 1/1/2001 and 3/1/2001
• Closed on a house in Silicon Valley in 3/7/2001
• Dot-com crash began 3/15/2001
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4. What’s the Moral?
• Luck happens
• Financial outcomes vary more than
operational ones
• Winner-take-all markets
• Timing of exits and/or stock sales
• Understand value of market leadership
• Don’t be too busy doing your job to think
about your financial outcome
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5. The Butterfly Effect
• Steve, a brilliant guy, ran an ~$150M company with search/BI technology
• The company was, however, kind of stuck growth-wise
• Probably worth around 3x its perpetual revenues
• Steve would never have believed it if you told him this future chain of
events would lead to a $1B+ exit
• HP’s then-CEO would attempt a dalliance with a marketing contractor
• That CEO would be fired over this
• HP’s board would appoint an unlikely new CEO as replacement
• The new CEO would waste over $11B on an overpriced acquisition in the space
• Steve’s company would be bought by Oracle as a hedge at 1/10th the cost
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6. What’s the Moral?
• Hard work and patience can be
rewarded in unusual ways
• Don’t forget the 12 backbreaking
years of work Steve put into building
that company
• There’s a lot you can control, and a lot
you can’t
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7. The Worst Thing That
Ever Happened to Me
• A few years later
• Just turned 40
• Life was going great
• Our fourth child, Brian, was two
weeks old
• And this came along 
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8. That Worked Out Fine …
(and here’s Brian today)
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9. But It Led to an Arguably Bad
Career Decision
• In 2004, I took CEO job at MarkLogic, an XML database
• “The market that never was” – Gartner, 2002
• From financial viewpoint, I should have “rinsed and repeated”
• And that was my plan, I wanted to be a CEO but was in no rush
• From self-actualization viewpoint, I needed to move
• When you’re discussing your “five-year survival rate” you sense a time premium
• We did simply amazing work
• Of ~16 XML databases, MarkLogic was effectively the sole survivor
• We created an $80M run-rate business
• But we didn’t create commensurate value
• Value comes from creating something someone wants to buy or go public
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10. What’s the Moral (1)?
On Life
• Both sides of the old model (work 40
unhappy years and then retire) are dead
• Assume that the experiment called your
life can end at any moment
• Optimize so you’re OK with your choices
in the unlikely event it does
• Don’t build debit balances – health, family
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11. What’s the Moral (2)? Picking is Huge
Choose Wisely
See: https://kellblog.com/2019/07/18/career-decisions-what-to-look-for-in-a-software-startup/
and: https://kellblog.com/2019/08/13/things-to-avoid-in-selecting-an-executive-level-job-at-a-software-startup/ Slide 11

12. What’s the
Moral (3)?
Rinse and
Repeat is
Lucrative
Work up the
career ladder here
You can make a lot
of money here
Beware anyone
offering you a job here
(Matrix is designed from the point of view of the hiring company.)
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13. What’s the Moral (4)?
Know Where You’re Going
• Choose your career goal with these circles
• There’s a time for making money and a time for
self-actualization
• Be smart about choosing
• Self-actualization (i.e., trying to reach your
potential) is important, but comes at a cost
• High opportunity cost
• High risk of failure (kind of the point)
Good
At
Enjoy
Doing
Make
Money
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14. First Observation on Scaling
As we grew BusinessObjects from $30M to $1B+, I noticed an interesting thing:
• The CEO role was largely strategic and changed relatively little over time
• While the COO changed radically as we scaled from 250 to over 4500 people
• We had one CEO, but 4+ COOs across that time period
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15. What’s the Moral?
Create a Scalable Role and Embrace Metrics
If you want to be in it for the long haul:
• Define yourself into a role that doesn’t require directly building and
scaling a huge organization
• Build COO, CRO, and/or country manager roles where you can hire for
operational experience there
• Become an expert in metrics
• Metrics are the abstraction through which you can understand the business
and compare it to peers
• That abstraction layer enables huge scalability – a $10M company has a CAC
ratio, and so does a $10B one.
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16. Second Observation
on Scaling
• If you want to be in it for the long-run, you
have to continually survive the short-run
• Easier said than done, given there will
always be good periods and bad periods
• People with revenue responsibility are the
first to go
• Boards default to assuming S&M
problems
• Not always correct but the least painful
option to consider
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17. What’s the Moral? Be the Other Co-Founder
• Be smart-humble: let the other co-founder be CEO or take revenue
responsibility
And/or:
• Have strong control provisions
• Have strong advocates on the board
• Stay aligned with the board
• This process starts at investment time
• Don’t be too busy running the company to communicate with the
board, especially during rough times
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18. The Most out of the Next 5 Years, Summary
• Understand that luck happens
• Seen all combinations of {good, bad} x {things, people}
• Don’t take it personally; don’t get too cocky
• Think of startups as white water rafting
• Some things you can control, others you can’t
• Learn how paddle (execute) and learn about the river (the system)
• Assume the experiment called your life can end at any moment
• Make your choices accordingly
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19. The Most out of the Next 5 Years, Summary (2)
• Understand the criticality of picking
• You are defined by the brands/decisions on your resume
• Your network is defined by the people you have worked with
• Picking is one key use of your paddle
• Choose your career goal, perhaps in phases, using the three circles
• Think mindfully about what mode you want to be in
• If you want to be around long-run, you need to survive short-run
• Define yourself into a long-run role
• Become an expert in metrics as an abstraction of the business
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20. The Most out of the Next 5 Years, Summary (3)
• Don’t be too busy doing your job to
• Think about your financial outcome and strategy
• Communicate and stay aligned with the board, particularly during the
toughest times
• Bonus: build a network with your peers
• Bonus: keep your kitchen clean and your cap table cleaner!
• Always view your cap table from perspective of your next-round investor
• For more discussion in a future Kellblog post!
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21. Follow me at @Kellblog
Check out my blog at www.Kellblog.com
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