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Title21 Golden Rules of Entrepreneurship eBook
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Page 2


The first lesson that I offer is simply this: you’ll see it when you believe it. This is, of
course, a reversal on the old adage “I’ll believe it when I see it,” which is how we’re trained
to think: when you show people proof, then they will believe it.

This is not how great entrepreneurs
approach their life. Exceptional people,
no matter what the endeavor is, believe
it first, and then they see it. This just
means that they’re able to see in their
mind’s eye, with great detail, what
they want a future experience to be
like. They paint a picture in their

minds with such specificity, color and richness, that it becomes real.

That was how I began my journey, with the feeling that I could manifest the things in
my mind into reality. When I was running for student body president at UCSB, I
literally walked down to the halls lined with pictures of student presidents and I imagined
my face on that wall. And a couple months later, it was.

Exceptional people, no
matter what the endeavor
is, believe it first, and
then they see it.

I’ll See it
When I Believe It

This drives me to my next question, which is
a completely serious one: Do you ever feel
like you’re meant for really big,
incredible things? So big, in fact, that to
say it out loud almost feels embarrassing?
But why does saying “I want to be the
president of the United States” sound so
silly? Somebody’s going to be president,
why not me? Why not you?

This comes to the second quality that’s
always driven me, and that’s a perpetual
sense of urgency. I literally wake up
every single morning feeling as if there’s a
clock of my life that’s ticking down. I feel
that every second passing is one less moment
I have to work towards the important thing
I’m meant to achieve, and if I’m not

working towards it I’m wasting that precious

Take a moment to picture some cheesy
turning point in a film, when an old and
regretful character says “I wish I had more
time.” Sure, it’s sappy and cliché, but this is
a recurring theme in film and art for a

The thought of fast forwarding fifty years
from now and realizing I hadn’t done what I
wanted to do is the most gut-wrenching
prospect I can imagine. I decided in my
early twenties that no matter what, I would
always be willing to take a risk. It’s
okay if I didn’t achieve everything I wanted,
as long as I went after it as hard as I could.

Perpetual Sense of Urgency

Page 6


10 Questions to Consider
When Starting a Business

During my time working in business consulting, I helped companies write business plans and prepare themselves for
investment presentations. Through this process, I learned that you don’t need experience or a degree to succeed, but
you need the ability to sell your idea, and sell it well.

After years of watching people draft and present their plans, I distilled a list of ten essential questions for
every entrepreneur starting a business:

1. The first step is to clearly describe your product or service. Describe it like you would to a fifth grader, so
that he would actually understand it. If you couldn’t explain your product or service to a 5th grader so that he
could explain it to an adult, it’s too complicated.

2. The second is to determine its unique value proposition. What makes your product or service different, or
better? Facebook and Groupon were not the first of their kind, but they were different and better.

3. Third, explore the market opportunity. What problem are you solving, and how many dollars are spent every
year on your business category. Is the market growing?

4. Who are your competitors? What can you do better than them?

5. How will you make revenue, through subscriptions, ads, sales? You’d be very surprised how many people don’t
even consider how they’re going to make money before they begin.

6. Establish your team. Who’s running the show?

7. What is your strategy? Strategy should simply involve
asking “What’s my business going to be like in 10 years
from now?” then breaking that down to smaller goals:
what you need to accomplish in 3 months, in 6 months, 9
months, and a year. That’s it. Keep it simple.

8. How much money do you need to get the product off
the ground? How much will you need to actually get
people to buy it? How will you market it?

9. Create some financial projections, how much you
need, how much you’re going to make; determine when
and how you will become profitable.

10. Decide the valuation of the company. This simply means that if you’re going to give up a certain percentage of
your company, how much do you want back?

If you follow these questions and display your answers cleanly in a PowerPoint deck, you will have a better business
plan than the vast majority of entrepreneurs that have passed through my office. I’ve seen hundreds of businesses
pitched in the last year alone, and many of them are missing some of these fundamentals.

Quick Tip: When presenting your
business plan to investors, don’t use a
lot of text. Investors may have years of
experience and education, but ultimately
they want kid’s storybooks. I’m not
kidding. They like a lot of nice pictures
and graphics, a little bit of text.

Page 7


The final key element of my preparation was that I constantly courted mentors. I was
never the best student, but I met with successful alumni often, and socialized constantly with
members of my academic and professional community.

I would call up alumni and ask to meet them. I wouldn’t ask for anything, a job or a
connection. I just asked them to tell me their story, and then would ask them “Would
you consider being my mentor?” They always said yes, and were flattered for the opportunity.

In that moment, I had established relationship where this person actually felt
responsible for me in some way. More importantly, I stayed in touch with them, asked
them for advice, and often took it. It was this group of people who I’d asked to mentor me, that
gave me half a million dollars to start DocStoc before I even had a product.

Court Mentors

A lot of people look ask the founder of
successful companies “how did you do it?”
But when you’re taking on a huge endeavor
like creating a business, traveling the world
or starting a big project, the most
important question to ask yourself is

What’s driving you? What’s your “why” for
doing this? If you don’t have a big “why”
constantly pushing you forward, you’re

always going to use the “what” and the
“how” as an excuse for not following

This is so critical for any big enterprise, I will
repeat it again: if “why” isn’t
constantly driving you, you’ll get hung
up on “how.” You’ll end up saying
something along the lines of, “I was going to
start this business but I couldn’t figure out
how to do it. I couldn’t raise the money.”
That’s not true, other people have raised the
money. You just didn’t have a big enough

If you have a “why,” keep it close; you’ll
need it when the goings get rough. The first
two years of running DocStoc I was in that
office every day 15 to 16 hours a day, and
today I still work on average 12 hours a day
in the office. Anything worth working for is
going to be tough.

Find your WHY

If you don’t have a big “why”
constantly pushing you forward,
you’re always going to use the
“what” and the “how” as an
excuse for not following

Page 13


Let me review one last thing about achieving
something significant. When it comes to
accomplishing your goals, most of us get
caught up in a long list of things to do. It feels
good to check things off that list, and feel like
you’ve accomplished something.

However, most of the little things we do every
day don’t contribute to your larger goal. What
really catalyzes start-ups and successful people,
is beginning each day by asking: “If I get one
thing done today, this week or this month,
what will it be? What is the most important
thing in my life right now?” Then write this
down, and spend 80% of your time on that
one task.

When we first started DocStoc, I was
obsessive about our traffic. That was the
most important thing to do, and it was all I

thought about. Once we had a couple million
people coming to the site, I turned my
obsession to breaking even. I fixated on
finances, so that we stopped burning through
our venture capital money and became self-

Once we did that, I was obsessive about how
we could grow our revenue 100% per year,
and build a business that would grow enough
to justify venture capital investment. Today,
I’m obsessive about owning an entire small
business category, and being the premier
destination online for every single small
business owner.

If at any given time in your business or
personal life, there is one thing that you spend
80% of your time on, it will make a huge
difference in terms of overall accomplishment.

The One Most Important Thing

When you set a goal, remember not just to say you’ll achieve it, but to really see in your mind’s eye
the outcome you’re working towards. Most importantly, infuse it with the most valuable thing you
have: your certainty.

Certainty doesn’t come from people telling you that you’re great, or any form of external
validation. Certainty comes from your own belief in yourself.

Things will never be easy. The economy will fluctuate, you’ll have tough days, and
you’ll never be able to convince everyone of your decisions. But if I’ve learned
anything in my life thus far, it’s that if you have that certainty in yourself, you will be
able to achieve everything you want and deserve.


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