Tangible Lessons from My 20s by John Brennan

tangible20s
LESSONS FROM MY
Real, actionable advice from an entrepreneur’s experience
John Brennan

Lessons from My 20s
INTRODUCTION

Get in touch with me:
john@buzztable.com
@worldlyjohn
Lessons from My 20s
ABOUT ME
Many people do something crazy when they enter a new
decade of life. Some travel in search of meaning, others
make big career moves or seek out adrenaline. I chose to
write an eBook.
I've learned a lot about engineering, business strategy and
spirituality in the last decade. I've started several
businesses, picked up advice from mentors, and spent time
soul searching. Last fall I sold my company BuzzTable to
Sysco Foods (SYY), and the experience gave me time to
revisit my life's goals.
I certainly didn’t get to this point unscathed, and I can almost count the startup
failures on two hands. I contribute a large part of these failures to lack of
knowledge and experience. I can’t promise to teach you experience in this deck,
but hopefully my journey can help you avoid a few common pitfalls.

WHO IS THIS FOR?
Although this started as a personal exercise, my hope is that other, early stage
entrepreneurs will also find value in this. I wanted to take a holistic view to this
exercise which is why the “Life” section remains intact because without a work-life
Lessons from My 20s
balance you will most likely burn out.
Some lessons you may have already learned yourself, others may not apply to
you at this current moment -- that’s okay.
My hope is that the time you spend reading (or skimming) this micro-book will
have paid you back a few times over in the knowledge you will have gained.

OVERVIEW
Slides are organized
into 2 parts:
BUSINESS and LIFE
Lessons from My 20s

Lessons from My 20s
Part 2: Life
HAPPINESS
MINDFULNESS
HEALTH
RELATIONSHIPS
INVESTING
GOALS
TOPICS
Part 1: Business
TEAM & CULTURE
STRATEGY & EXECUTION
REVENUE MODELS
PRODUCT DEVELOPMENT
SALES & MARKETING
ACQUISITION
VENTURE CAPITAL
STARTUP CHECKLIST

OVERVIEW
Lessons from My 20s
It’s about 150 slides.
BUT, if you are
short on time
there’s a cheat sheet...

Lessons from My 20s
CHEAT SHEET
TEAM & CULTURE
1. The one thing no competitor can copy or replicate
2. If you don’t define your culture it will define you
3. Communicate your north star often
4. Celebrate the small things
5. Solve tough personal issues early
6. Maintain a balance
7. Foster respect through mutual understanding
8. Decisions made by data
9. Hire people with different perspectives
10. Hire generalists early on, specialists after product fit
1. Lack of focus kills a startup
2. Develop milestones early on
3. Success emulates success
4. Remove the unknowns
5. Be hypothesis driven
6. Be honest with the challenges you face
STRATEGY & EXECUTION (cont.)
7. Build processes
8. Never outsource your core value
9. Every problem is a funnel
10. Customer and market segmentation
REVENUE MODELS
PRODUCT DEVELOPMENT
1. Ship before you want to
2. Say no a lot
3. Do 2 things at 100% everything else at 80%
4. Make 1st-time users happy as fast as possible
5. Less is more
6. It’s not always what, but when
7. Track everything
8. Empower ownership
9. Don’t write product specs
10. Build lead capture into the product early on
PART 1: Business Lessons

Lessons from My 20s
CHEAT SHEET
SALES & MARKETING
1. Setting goals
2. When it’s not about the numbers
3. Road to a repeatable sales process
4. Building a repeatable sales process
5. Know thy funnel
6. Unit economics are your friend
7. Don’t automate too early
8. Skip resellers
9. Think different
10. Customer satisfaction drives everything
ACQUISITION
1. Love the struggle
2. Companies are bought not sold
3. Conversations begin in many ways
4. Keep working
5. Get the letter of intent
ACQUISITION (cont.)
6. Lawyer up for the due diligence
7. Negotiate the LOI
8. Valuations
9. Dating goes both ways
10. Be prepared for change
VENTURE CAPITAL
1. How big is your market?
2. Show traction
3. Build relationships
4. Be serious about the financial model
5. Know thy unit economics
6. Finding investors
7. Investor feedback can be contradictory
8. You will never hear “no”, just “not now”
9. Understand the terms
STARTUP CHECKLIST
PART 1: Business Lessons

Lessons from My 20s
CHEAT SHEET
HAPPINESS
1. Harmony between heart and mind
2. Quality of your thoughts
3. Live in the moment
4. Buy experiences not things
5. Create your purpose
MINDFULNESS
1. Enlightenment is not a destination
2. Compassion through understanding
3. You can’t see the truth, only a perspective
4. Live with gratitude
5. Embrace uncertainty
6. You are here and here is perfect
7. A step back often becomes a step forward
8. Perfect timing does not exist
9. Breathing exercises
10. Deepening your practice
HEALTH
1. Eat your super foods
HEALTH (cont.)
2. Practice preventive health
3. Get your heart rate up
4. Detox annually
5. Yoga is more than “stretching”
RELATIONSHIPS
INVESTING
1. Personal goals should dictate your strategy
2. If you remember one thing, it’s asset allocation
3. Use index funds to the finish line
4. Dollar-cost averaging
5. Interest rates
6. Stocks
7. Bonds
8. Real Estate
9. Commodities
10. Peer-to-peer lending
PART 2: Life Lessons

Lessons from My 20s
part 1
what i’ve learned in...
BUSINESS

Lessons from My 20s
TOPICS
Part 1: Business
TEAM & CULTURE
REVENUE MODELS
PRODUCT DEVELOPMENT
SALES & MARKETING
ACQUISITION
VENTURE CAPITAL
STARTUP CHECKLIST

Lessons from My 20s
part 1: business
TEAM &
CULTURE

Lessons from My 20s 1TEAM & CULTURE
TEAM
the one thing no competitor
can copy or replicate
Many of us read technology articles as part of our morning routine. When we started
building our business, every article about a competitor can be a small blow to our
morale.
I remember reading an article about a competitor that copied several of our features in
their latest release. It didn’t bother me because I knew we could push the envelope
again. That’s the thing about the team you go to battle with - you can always jump
ahead again tomorrow.

if you don’t define your
CULTURE
it will define you
When I was building OpenAction with my former cofounder (and still close friend), we
spent a lot of time working on product/sales and very little on the “culture.” We were just
getting to know each other when we were starting the company, and by sheer luck had
similar interests in the outdoors. Unfortunately, we rarely integrated that into the culture
at work, especially as our team grew. Our culture just happened.
At BuzzTable, I wanted to take a different approach and be more deliberate. We started
with monthly outings (paintball, rock climbing, etc) and eventually the group threw out
suggestions. The culture became larger than myself. Hopefully I can replicate that again.

TEAM & CULTURE communicate your
NORTH STAR
often
3 Your north star is the vision and direction of the company. While you will have a good
grasp of this, your team does not sit in every meeting with you and their perspective
may differ. Communicate the “why” in addition to the “what” as often as you can.
I think this problem is correlated with company size. When you are 4-8 people in a
room, there are so many conversation exchanges in real time that it’s easy to stay on
the same page. Once you grow out of a single room, you’ll need more than quarterly
updates to communicate the 5 “W’s.” Align your goals to it, repeat yourself often.
Lessons from My 20s

TEAM & CULTURE
CELEBRATE
the small things
4
Milestone wins, no matter how insignificant they seem, bring the
team closer together. When we first started out we didn’t have a
snack bar or a water cooler in the office... after a few early
milestones that changed. The whole team was a part of the
selection process. Most notably for the office minibar. =) Lessons from My 20s

solve tough personal issues
EARLY
Founder/team issues will compound themselves with every milestone or funding round.
Problems never resolve themselves, quite the opposite actually.
Even after we raised a large funding round in a previous company, we still had founder
issues around our roles and responsibilities. I imagine this problem is common with
overlapping skill sets. I promise the conversation will be harder tomorrow, so address
it today.

maintain a
BALANCE
6 TEAM & CULTURE
All work and no play is a recipe for burnout. Remember, the
company you are building is a marathon, not a sprint.
We had small monthly retreats as a team (rock climbing, paintball,
play hooky and see a movie) and larger weekend retreats once a
quarter (ski trip, RV road trip from NYC to Chicago, etc).
http://www.fastcompany.com/3002879/designing-one-week-team-sabbatical-will-transform-your-company
http://product.skillshare.com/2012/09/whats-a-company-retreat-for/Lessons from My 20s

TEAM & CULTURE FOSTER RESPECT
between disciplines 7 through
mutual understanding
Everyones’ job is hard. Most of the time engineers can’t sell and salespeople can’t write
code. That’s why you’re a team.
Understanding each other’s pain points leads to mutual respect. We achieved this at
BuzzTable because it was built into the culture early. When the product team stayed until
midnight every night the week before we had to ship, sales stay there with us to
prospect. We held code hackathons AND sales hackathons together. And that made all
the difference in the world.
Lessons from My 20s

TEAM & CULTURE decisions made by
DATA
8 It’s about the data, not the ego. If there is no data, default to the decision maker. Let
everyone in the company know this. You never know who may uncover a bright spot.
This also is a great point to make when hiring engineers.
I remember when we were just starting BuzzTable we were marketing to the end user
(the restaurant guest). Our conversion rate (getting restaurant owners to sign up) was
terrible. We wanted to position ourselves as a consumer app (investors wanted this
too), but the data was telling us a different story. I spent a few weeks tweaking the site
based on visitor behavior (Google Analytics) and found our conversion rate triple!
Lessons from My 20s

hire people with
DIFFERENT
PERSPECTIVES
While I didn’t have the chance to really follow through with this at BuzzTable, I started to
realize that our team was fairly homogenous. It makes sense because we hired friends
and friends of friends. I worried that as we grew from 10 to 30 we would need to hire
out of network and feared that some new members would feel like outsiders. I was also
aware that the best products are derived from many perspectives. You might not follow
this when you’re still hiring in single digits, but it should always be top of mind.

Your idea and market may change, so
hire generalists early on,
specialists after product fit
You’ll probably need a different type of sales person if you decide your model is best
suited to inbound sales (versus outside sales). The same thinking can be applied to
engineers. Both of my prior companies had pivots before we knew what we wanted to be.

Lessons from My 20s
part 1: business
STRATEGY &
EXECUTION

STRATEGY & EXECUTION LACK OF FOCUS
kills a startup
You want to start solving a problem that’s narrow and 1 deep. Think Facebook’s debut at
Harvard. Attract users that really want it. Listen, learn and iterate. You can build less to
satisfy the problem and spend less to acquire new users.
If you take away only one lesson from this deck, this is it. Often the decision to pare
down and focus, is hard. While building BuzzTable we couldn’t decide if we would have
more success leading with b2b or b2c. We were getting pulled in both directions from
different investors. Once we finally chose b2b, we built a lead-converting website, and
started to see the growth. Our decision was evident. If I had to do it over again, I’d
spend more time creating small experiments to test both models early. Every model will
have its challenges. For us, generating leads was easy and the work was in conversion.
Lessons from My 20s

STRATEGY & EXECUTION develop
MILESTONES
early on
2 Define OKRs (Objectives and Key Results) quarterly and review monthly. Early on, focus
more on learning (engagement) than revenue or sales targets. As patterns emerge,
you can adapt.
Coming up with OKRs early will help you focus, but it’s really hard to plan for the next
three to six months when you are just starting out and have only a few months of
runway. At my previous startup we went month to month with funding for the first nine
months. Even after we closed on our seed round, we still weren’t thinking in terms of
milestones (aside from product), and that made it hard to achieve the targets I had in
mind. Once we set up formal checkins, each quarter and month, we got more done.
Lessons from My 20s

success
EMULATES success
3
Another company has probably faced a similar challenge before,
so instead of reinventing the wheel, leverage the work of great
minds. Add your value on top.
For example, when building BuzzTable, I thought of the website
as a SaaS-based, lead gen tool. First thing I did was learn what
made Salesforce, ZenDesk, and Zuora great.Lessons from My 20s

remove the
UNKNOWNS
4
Every business makes assumptions until they know the answer.
The key is to know what unknowns will have the largest impact.
Define, prioritize and begin to test your assumptions today. Lessons from My 20s

STRATEGY & EXECUTION be
HYPOTHESIS
driven
5 Create a culture of experimentation.
Emphasize learning and iterating.
Don’t point fingers at failed solution or place blame at missed
numbers early on -- as long as you are learning.
Lessons from My 20s

Lessons from My 20s 6STRATEGY & EXECUTION
be HONEST with
YOURSELF about the
challenges you face
One must not confuse persistence with obliviousness. No one cares about new feature X if
you still have zero customers. Stop building new features and understand what pain
points your target customer actually has.
This requires a bit of self reflection, so pause for 5 minutes and think about whether your
business is where you hoped it would be six months ago. If not, why do you think that is?
Once you are honest with yourself, then you can begin to formulate a plan to win.

STRATEGY & EXECUTION 7 build
Lessons from My 20s
PROCESSES
Performance Reviews
New Employee Training
Tech Stack Setup
Purchase Orders
Office Supplies/Snacks/Lunch
Payroll
Customer Onboarding
Product Feedback
Downtime/Update Notification
Internal/External Communications
Vacation Requests
Legal Contracts

STRATEGY & EXECUTION never outsource your
CORE VALUE
8 If you are a technology company this means building an internal
engineering team over an outsourced dev shop.
When building out sales channels, avoid resellers who push you
farther away from the customers you are trying to reach. It will be
harder to get the valuable feedback you need to iterate.
Lessons from My 20s

every problem
IS A FUNNEL
Whether you are trying to raise capital or
find your first few paying customers, you can
think about it as a funnel. Start with your
target goal and work backwards. Assume a
conservative success rate and figure out the
number of prospects you will need.
Then GO!
50 prospects
30 meetings
10 customers

customer and market
SEGMENTATION
Mark Suster refers to this as “Deer Hunters.” A common and often fatal flaw early in your
company’s life is picking the wrong customer segment, or worse yet, not knowing what
segment your target customer is.
The animal analogy corresponds to the typical contract size. Elephants are massive
customers like PepsiCo or Microsoft. The contract may be worth $1m, but could take years to
land if you are even so lucky.
For brevity sake, see Mark’s blog below. The second link is a new take on the model,
introducing “flies” and “mice”-size customers.
http://www.bothsidesofthetable.com/2009/09/16/most-startups-should-be-deer-hunters/
http://christophjanz.blogspot.com/2014/10/five-ways-to-build-100-million-business.html

Lessons from My 20s
part 1: business
REVENUE
MODELS

REVENUE MODELS
when starting a business,
it’s often helpful to see
examples of web and mobile
REVENUE MODELS
Lessons from My 20s

REVENUE MODELS
Lessons from My 20s
TRANSACTIONS
merchant acquiring (paypal, stripe)
processor (paymentech)
payment gateway (firstdata)
ACH (dwolla)
card issuance (simple)
messaging (whatsup)
ADVERTISING
display/search (Google)
audio/video ads (Pandora/Hulu)
promoted content (twitter)
lead generation (zocdoc)
featured listings (yelp)
retargeting (criteo)
DATA
user data (bluekai)
business data (duedil)
user intel (yougov)
search data (chango)
consumer intent (yieldbot)
benchmarking (comscore)
LICENSING
pay per seat (salesforce)
per device
per app instance (photoshop)
brand licensing
SUBSCRIPTION
Software as a Service (salesforce)
Service as a Service (Shopify)
Content as a Service (Spotify)
Platform as a Service (AWS)
Sampling (Birchbox)
Paywall (NYTimes)
COMMERCE
retail (zappos)
marketplace (etsy)
crowdsourced market (threadless)
excess capacity mrks (uber, airbnb)
vertically integrated (warby parker)
digital goods (iTunes)
PEER TO PEER
buying (etsy)
services (taskrabbit)
mobile wifi
lending (lending club)
gambling (betfair)
auctions (ebay)
here are 7:
For more, see: http://bit.ly/bizmodelex

part 1: business
PRODUCT
DEVELOPMENT
Lessons from My 20s

Lessons from My 20s 1PRODUCT DEVELOPMENT
SHIP
before you want to
-Reid Hoffman
I learned this the hard way a few times. I was building a social network in college. It took
almost a year to get the product to a point where I was ready to show others my work.
Unfortunately, it was too late. People may not have cared in the first two months while I
was building it, but that could’ve saved me 9 months!
Releasing your creation makes you vulnerable. No one gets that more than me.
However, I have also learned that you are doing a disservice to your creative work by
not putting it out there. Everything evolves -- even this presentation you’re reading.
Embrace it.

say NO a lot
Your product is measured by what you don’t put in it just as much as what is. Say “Yes”
once for every 50 “No”s. This often means saying no to custom work from early
customers, unless you want to become a dev shop.
While building OpenAction, a mapping platform for non-profit organizations, one of our
investors offered us additional money to add a few features to the product so another
company of his could use it. Turning down any additional revenue early on is a hard
decision, but I knew it was the right one. He commended us later it.
Do not blindly say “No.” Understand if it’s something that many users will experience.
Build for those cases. Another example is the company, 37Signals, makers of
BaseCamp. Instead of writing down feature requests, I’ve heard they discuss them
verbally each week, those heard often get developed.

Do 2 things at 100%
everything else
at 80%
Think about the two most important use cases (signup, form entry, invite others) and be
maniacal about crafting them to 100%. Everything else should be built “good enough.”
You need to move fast and a lot of stuff will either change or won’t be important in 6 months.

make 1st-time users happy
AS FAST AS
POSSIBLE
Dave McClure calls this “activation.” You want to lead your new
users to an “aha!” moment as fast as possible. Don’t tell them
why they should use your product, show them.
Spend a lot of time here.

less is
MORE
Use simple, common tools and architecture. Build shallow. Your
MVP probably doesn’t require memcached at launch. When
building your MVP, use the tech you know so you know what to do
when things go wrong (because they will).
The less code you write, the easier it will be to maintain and grow.

it’s not always “what”
BUT “WHEN”
It’s easy to say “No” to bad ideas.
It’s much harder to say “No” to good ideas
that you just shouldn’t do right now.

track
EVERYTHING
But spend time deciding what the right things to report are. Don’t fall into the trap of
paralysis by analysis. Plan before you track.
Collect quantitative and qualitative information. Quant usually tells you how something
you built is working while qualitative data is where you’ll find new opportunities to
improve and WOW your customer.

empower
OWNERSHIP
Spend time thinking about how to be autonomous as you grow. Don’t become a
bottleneck. Empower others to own parts of the product. This strategy will increase
employee happiness and let you move faster.
I actually learned this lesson before I ever embarked on my startup journey. I was
working at Microsoft and pleasantly surprised at how much responsibility was expected
of me even during my first week as part of the team. It motivated and inspired me. I’ve
taken that lesson and tried to infuse it with ever company I’ve started since.

don’t write product
SPECS
Let code comments and unit tests serve as your documentation early on. When you are
developing your MVP lots of “features” turn out to be irrelevant. Spend most of your
timing trying to build something of value instead of writing about it.
After we hired our first engineer, I made sure that any question he had was recorded.
This became our first “onboarding” material for future engineers we hired.

build lead capture
into the product
early on
I touch on this in the slide on “focus” when I recalled how we built a simple lead-gen
capture system. It provided the proof points to show that a inbound sales and
marketing model would serve our business well.

part 1: business
SALES &
MARKETING
Lessons from My 20s

SALES & MARKETING setting
GOALS
Unlike mature companies where sales goals are often 1 revenue targets, early stage
startups may have little or no revenue so goal creating gets blurry. Goals should still
align with company strategy, but may require creativity.
At BuzzTable, we wanted to focus on accounts that had “willingness” to pay, but didn’t
want to focus limited resources on the payment collection process. I found a simple
usage pattern, dubbed it “premium eligible,” and used that as our guiding metric. Once
we had the resources, we resumed revenue collection, and had a much better growth
trajectory because of steps taken early on.
Lessons from My 20s

SALES & MARKETING when it’s not about the
NUMBERS
One of the mistakes I made early on in my previous 2 company was to pressure our sales
team to provide target numbers each month. While this is common practice after
achieving product-market fit, it's much harder to do before a baseline can be
established with past months data.
The results of this decision led to a drop in moral when numbers weren't hit and a lack
of learning because we were so focused on the numbers. If I do it again, I would focus
the first few months on sharing lessons learned, and only on numbers once patterns
emerged.
Lessons from My 20s

SALES & MARKETING road to a repeatable
SALES PROCESS
No company starts with a scalable sales process. Your 3 first few customers can help you
identify bright spots. That is, the specific customer profile that sees your solution as a
painkiller (as opposed to a vitamin). Learn everything you can about this customer’s
behaviors -- how they buy, when, where. Once you are here, create a process and start
automating.
Don’t hire additional sales people until you have a documented process! You will
hemorrhage money if you grow prematurely.
Lessons from My 20s

Lessons from My 20s 4SALES & MARKETING
building a repeatable
SALES PROCESS
Don’t confuse your early customer success with a scalable sales process. You will know
you are here because you will want to hire more people to keep up with demand. Don’t.
Try to automate the onboarding process as much as possible. Leverage marketing
automation tools like Marketo or Hubspot to do a lot of the heavy lifting.
At BuzzTable, we started to get overwhelmed with the amount of leads coming in. We
could have hired one or two more people to alleviate this bottleneck, but what happens
when you hit a ceiling again? Instead, we solved this pain through market automation
and more than tripled the number of leads each person could handle.

SALES & MARKETING 5 know thy
Lessons from My 20s
FUNNEL
(top of the funnel)
(bottom of the funnel)
(middle of the funnel)
In the strategy section, I mention
the broad funnel as a way to frame
most goals. This is especially
important for S&M. Marketing, at
the top of the funnel, is about
opening the door. Sales closing it.
The infographic on the right is a
good visualization. You can take a
deep dive into any of these areas
for tried and true strategies via
Google.

SALES & MARKETING 6 unit economics
ARE YOUR FRIEND
If searching for product-market fit you can glance over this. As you find PMF it’s important
to understand your cost to acquire (CTA) and lifetime value (LTV). You won’t be able to raise
cash, and more importantly, won’t have a viable business without them. I’ve probably read
David Skok’s blog three times over and you should too.
For SaaS
startups: <12 months > 3x
LTV CTA Months to
recover CTA
Lessons from My 20s
David Skok’s blog: http://www.forentrepreneurs.com/

SALES & MARKETING 7 don’t automate
TOO EARLY
Always start with a “high touch” customer model, meaning you personally speak to each
customer. As you gain intimate insights about your customer, you can start to move into a
“low touch” model. This means leveraging tools from Hubspot to capture leads, create drip
campaigns, etc. to Zendesk to do the heavy lifting with customer service.
I caution against a “zero touch” model. While it may free up cash in the short term,
product quality will erode in the long run.
Lessons from My 20s

8 SALES & MARKETING skip
RESELLERS
Especially early on. Resellers will push you too far from your
customer and feedback is the fuel of early product development.
Lessons from My 20s

SALES & MARKETING think
DIFFERENT
When it comes to marketing, nothing is harder than nailing 9 the company messaging
(positioning). You need to exude empathy with your target customer, but you also need to
craft a unique experience to tell customers how they should think of you.
In my opinion, Lyft has continued to do this well. They started with the pink mustache to
create awareness (e.g. why are cars in San Francisco driving around with this?) and now
position themselves as your neighborhood driver against Uber’s “private driver” mantra.
Lessons from My 20s

SALES & MARKETING 10 customer satisfaction
DRIVES EVERYTHING
Delight customers and you will be rewarded. Whether you drive incremental revenue
through upselling/cross-selling or through referrals, none of this will happen if you haven’t
“WOWed” your customer.
Make it a top priority.
Lessons from My 20s

Lessons from My 20s
part 1: business
ACQUISITION

ACQUISITION
love the
STRUGGLE
While you're in the struggle, the period early in the startup 1 when you feel the world is
against you, you will think the best moment will be when you get acquired.
After you get acquired, you will remember the best moments as building the business
and struggling together.
Live in the moment!
Definition of “the struggle”: http://www.bhorowitz.com/the_struggle
Lessons from My 20s

Lessons from My 20s 2ACQUISITION
companies are bought
NOT SOLD
You can improve your odds by getting the attention of the right people, usually within
the Corporate Development team.
Increase your odds by getting in touch with these people early. Whether a mutually
beneficial partnership or just to get on their radar because you think it might be of
interest to them. Investors/advisors can help tremendously here, so make sure you are
giving them ammo to talk about you (frequent updates).

conversations begin
IN MANY WAYS
For some reason most acquisition talks never begin that way. It may start as a
partnership discussion or an investment.

KEEP WORKING
Assume the deal will fall through. Many deals never make it to a term sheet, and some that
do fall apart before it’s consummated.
It will be hard enough for the executive team to get back in the mindset of building the
business if things go awry. I can guarantee it will be detrimental if the business goes on
autopilot during this time. I’ve heard this happen to a few companies I’ve crossed paths
with in the last few years. Some founders had to take a hiatus because the emotional drop
was so rough. It’s very hard to muster the determination to power through once you’ve told
yourself the deal is all but done.

get the
LETTER OF INTENT
Never take a company too seriously until you receive a letter of intent, which is basically an
outline of terms and purchase price.
Even after you receive an LOI, the acquisition should not be a top priority until you’re at the
home stretch. If things fall through, it will be hard enough for you to mentally come back to
the daily routine.
Avoid signing a no-shop until you have a signed LOI (at the minimum).

lawyer up for
DUE DILIGENCE
The acquirers’ lawyers do M&A all day. Don’t bring a knife to a gun fight. Get solid
counsel to guide you through the process, especially if this if your first time.
Expect to spend $100-200k. Ask for the buyer to split or pay legal fees. Ask for a
breakup fee. You may not get either, but it doesn’t hurt to try.

negotiate
THE LOI
It is nearly impossible to change or expand on deal terms after the LOI is signed off, so
spend your time negotiating at this stage. Try to create alternative paths so you have some
chips in your corner - option to fundraise, competing acquisition offer, etc.
Understand deal killers and terms, especially if you have other investors on your board.
Indemnification is the most prominent one and allows the acquirer to take back it’s
purchase price (or more!) if you get sued. Read more online.
Make non-compete as narrow as possible. Avoid no-shop if you can.

VALUATIONS
• Multiple of earnings if generating revenue or
premium of valuation (~1.5-2x) from current/last round
• Understand the price bands when thinking of a number.
Under $15-20m requires fewer authorizations than $25-40m.
• Agree with partners on minimum sell price before you start.
• Don’t share cap table until you receive an LOI. Buyer may do a cost-based valuation
with majority in retention package.
• Think of retention as bonus, not part of deal. Things change post-acquisition and
goals may shift away from performance targets.

dating goes
BOTH WAYS
Similar to founder dating, make sure you do due diligence on the acquirer. Do they have
the right people and capital to follow through on their vision? How do you fit into the
organization and what support (HR, finance, etc) will you have? Will you operate
independently or get reallocated to other projects?
Note that these questions probably matter much less if this is your first acquisition.

be prepared for
CHANGE
Company culture will falter. Product and market position will suffer. It’s impossible to
continue to execute at a high level when you may have to deal with relocation, staff
changes, and new priorities.
Most of all, be aware that you are selling more than the company, but also your baby, your
passion for it, and everything you’ve built.

Lessons from My 20s
part 1: business
VENTURE
CAPITAL

VENTURE CAPITAL
how big is your
MARKET?
It can be frustrating when investors tell you that the 1 market you are going after “isn’t big
enough.” They are not saying this to be tough on you, but rather because they know that
as you develop a deeper understanding of the problem/customer your solution may
change. If the market size is too small there won’t be sufficient room to pivot.
I remember when we were taking OpenAction to Series A investors in NYC. We were told
our market was too small, so we played with the numbers to get to $100m top line
revenue in year 5. This should have been a signal to us at the time that the model as we
had it wasn’t going to work, but we carried on. We pivoted to a new industry 6 months
later and sunset the company shortly after that.
Lessons from My 20s

VENTURE CAPITAL
show
TRACTION
I find first time entrepreneurs will cater to heavily to 2 what investors are asking for. Stop
building your business in the direction of investors, and start focusing on a pilot with
traction. If you don’t have traction quite yet, explain the subtleties of the problem you
are going after and why it matters.
Investors don’t bring traction, but traction sure will bring investors.
Lessons from My 20s

Lessons from My 20s 3VENTURE CAPITAL
build
RELATIONSHIPS
Most first time entrepreneurs see all capital equally, however you want to be as
selective as you can. The relationship with your investors is almost as important as your
co-founders. If you are lucky, you will be working together for a long time.
Mark Suster describes this best with his post about Investing in Lines, Not Dots.
http://www.bothsidesofthetable.com/2010/11/15/invest-in-lines-not-dots/

be serious about the
FINANCIAL MODEL
It’s easy to think of your financial model as “checking the box” for investors, but it can
help you more than you know. Sure, investors want to see $100m top line in 5 years,
but they are really interested to see how you are thinking about this business. What are
your revenue drivers? Can you achieve this or are you spreading yourself too thin? Do
the unit economics make sense?
Ironically, this is more important for you than anyone else. I mentioned my anecdote
about market size with OpenAction, and realized it took that experience to prioritize this
exercise. When starting BuzzTable in 2011, you can bet I spent a lot of time playing
with the financial model before jumping in with both feet.

VENTURE CAPITAL
know thy
UNIT ECONOMICS
Investors aren’t asking you to be ball busters. These 5 metrics help them understand how
you think about your business, how far along you are, and if you are ready for their capital.
B2B
B2C
customer acquisition cost (CAC)
repeat usage/engagement
lifetime value (LTV)
viral coefficient/sharing
lead velocity (lead growth MoM)
downloads
revenue per lead
Lessons from My 20s

VENTURE CAPITAL
finding
INVESTORS
I’ve spoke about funnels in past slides. Meetings are 6 a function of outreach, so load up
the top of that funnel (with quality).
• What types of investors are you looking for? 3Fs (friends/family/fools)? Angels? VCs?
• Are you b2b or b2c (consumer)? The right type makes all the difference.
• Create a list of names. Notable investors you read and would like to work with, early
investors in large incumbents in your space, etc.
• Use LinkedIn to find mutual connections and ask for intros.
• Don’t ask for coffee. Hook them with your 2-3 sentence pitch. Avoid buzzwords. Why
you? Offer to come to their offices (because they will probably ask anyway).
• Remaining list is cold outreach. Pick your top 5 and try to get their attention.
Lessons from My 20s

VENTURE CAPITAL
investor feedback can be
CONTRADICTORY
Every investor has an opinion and it’s often skewed in 7 the direction of their experience. If
you are speaking with an investor that previously built an enterprise technology company
with 800 sales people, get ready for that person to tell you how you should have an
outside sales team to hit the ground running.
Most important, if you know where you’re going, seek appropriate feedback. Otherwise,
cast a broad net then decide.
Lessons from My 20s

you will never hear “NO”
JUST “NOT NOW”
When you are raising your round, don’t wait for investors to tell you “no.” They will try
to avoid those two letters if they can. While you might not meet their investment criteria
today, they want to keep the door open with you incase something changes.
Keep on them as your round (and business traction) progress. If they grow less
interested, don’t waste time. Move on.

understand the
TERMS
VALUATION, OPTION POOL SIZE
LIQUIDATION PREFERENCES, FOUNDER VESTING
TYPE OF PREFERRED STOCK
VETO/BLOCKING RIGHTS
BOARD SEATS
Great deep dive here: http://www.slideshare.net/MarkHaddad/understanding-vc-term-sheets

Lessons from My 20s
part 1: business
STARTUP
CHECKLIST

STARTUP CHECKLIST
SCALE
Lessons from My 20s
OPTIMIZE
DISCOVERY
VALIDATE
MARKET
RESEARCH

STARTUP CHECKLIST
TIME IN STAGE: 1-2 months
EXIT CRITERIA:
Learn the key players, how things work, how money moves
Lessons from My 20s
MARKET
RESEARCH
• Try to convince yourself not to do it
• Conduct feasibility analysis, look at market signals
• Is there a clear need? (would your problem be a vitamin or a painkiller?)
• Initial assessment of acquisition/distribution channels
• What other skills are needed on your team? (becomes hiring plan)
• Where’s the competition?
• No competition is rarely a good thing unless you are creating a new category
(which is rare). Competition usually proves there is a market here
• Remove the big unknowns
• Create a list of questions and find industry experts to help answer them.
(Tip: Some of these people may become future “beta” testers)

EXIT CRITERIA:
Minimal viable product and value proposition are created,
founding team is formed
Lessons from My 20s
DISCOVERY
STARTUP CHECKLIST
• The only thing that matters is getting to product/market fit
• Hold others accountable to learnings not numbers
• Develop sales plan (skip marketing until you know more about your customer and
the voice you should have)
• Research all possible acquisition channels (ads, referrals) and begin to test them
• Begin to form your pitch deck (helps organize thoughts and focus)
• Corp formation (83b, IP assignments, trademark)
• DONTs:
• Concentrate on investors (you’re too early)
• Talk about partnerships (not a mutual value exchange yet)
• Document architecture/spec writing (it will change)

EXIT CRITERIA:
Find product/market fit, first paying customer, metric collection,
find evangelical customer, identify acquisition channels, key hires
Lessons from My 20s
VALIDATE
STARTUP CHECKLIST
• Define your KPIs (1-3 that company can get around, should be inline with model)
• Find bright spots (test different channels, pitches, segment customers)
• Think about team building early (culture, retreats)

TIME IN STAGE: 6 months
EXIT CRITERIA:
Conversion funnel optimized, repeatable sales process created
Lessons from My 20s
OPTIMIZE
STARTUP CHECKLIST
• Free your time with marketing automation
• Iterate on KPIs (hone on what’s most important)
• Watch out for premature scaling
• loading the hopper with issues downstream will exacerbate your problems
• Fix the leaky bucket. Your sales funnel will show you where to focus first.

Lessons from My 20s
SCALE
STARTUP CHECKLIST
EXIT CRITERIA:
Raise Series A financing, implement processes, improve backend
scalability, key roles become teams
At this point you probably already have a solid board and mentors that will guide you
through the final step of the process. The purpose of raising this round is to pour jet
fuel on the amazing unit economics you’ve found within your business.
Great job! You are further along than me. Perhaps you should consider writing about
your own lessons.

Congratulations
you completed the business lessons!
Lessons from My 20s

Remember,
business is just a s m a l l part of
the journey of life.
This isn’t a sprint. You love what you do,
so ensure you can do it for a long time.
Invest time in yourself. Aim for balance.
Here are my most valuable life lessons to date...
Lessons from My 20s

Lessons from My 20s
part 2
what i’ve learned in...
LIFE

Lessons from My 20s
TOPICS
Part 2: Life
HAPPINESS
MINDFULNESS
HEALTH
RELATIONSHIPS
INVESTING
GOALS

Lessons from My 20s
part 2: life
HAPPINESS

Lessons from My 20s 1HAPPINESS
HARMONY
between heart and mind
The longest journey that a man must take is the 18 inches between his head to his heart.
The mind is logical and will often lead you to what appears to be the “right” choice based
on millions of calculations with experience as it’s guide. The heart is unaware of past
experiences, and is the core of your Being. Sometimes the most difficult decision is what
the heart wants. For me, it has not always been easy to follow my heart. I haven’t always
had the courage to listen, but when I have listened, it’s never been wrong.

QUALITY
of your thoughts
The happiness of your life depends upon
the quality of your thoughts
- Marcus Aurelius, Meditations

live in the
MOMENT
Forty-seven percent of the time, the average mind is wandering, and it is not good for
well-being. A mind belongs in one place. Happiness comes from focusing on the
present moment.
After all, nothing else exists except this moment right now. This takes practice. Once I
started paying attention to the present moment, it was much easier to relax and let
problems - that felt insurmountable at the time - go.

HAPPINESS
buy experiences
NOT THINGS
If you can’t live in the moment, they say the next best thing is anticipation of the
moment. Experiential purchases (money spent on doing) 4 tend to provide more enduring
happiness than material purchases (money spent on having). As it turns out, waiting for
an experience elicits more happiness than waiting for a material good.
The common emotional response before you set off on vacation is excitement whereas
waiting for a new phone is usually met with impatience. If the event fails to meet
expectations a negative response is common for both experiences and material objects.
However, as time passes, the beach vacation that rained every day usually turns
positive while the disappointment that the new phone wasn’t an iPhone never does.
Source: Waiting for Merlot, Anticipatory Consumption of Experiential and Material Purchases. By Amit Kumar, Matthew A.
Killingsworth, et al.
Lessons from My 20s

HAPPINESS
create your
PURPOSE
5 Your purpose is not found, it’s created. You must give yourself time to reflect on what
you love doing. After selling my last company (along with the passion and purpose as it
seems), I’m now starting to create the space I need to do it again. I’m putting myself in
the mindset that anything is possible, soaking up all the new innovations in the world
and exploring what problems resonate with me that I might want to tackle next.
The graphic in the next slide may be a helpful way to wrap your head around the next
step in creating your purpose.
Lessons from My 20s

5HAPPINESS
create your
Lessons from My 20s PURPOSE
Source: Ryan Allis’ Lessons from My 20s
Purpose

Lessons from My 20s
part 2: life
MINDFULNESS

MINDFULNESS
What is mindfulness?
It’s the mental state of
being conscious or aware of
the present moment.
Lessons from My 20s

Lessons from My 20s 1MINDFULNESS
ENLIGHTENMENT
is not a destination
It’s a realization. And when you wake up, everything changes and nothing changes. My
favorite explanation of this is a story from the book “Way of the Peaceful Warrior”.
A young man had spent five arduous years searching for truth. One day, as he walked up into the foothills
of a great mountain range, he saw an old man approach from above, walking down the path, carrying a
heavy sack on his back. He sensed that this old man had been to the mountain top; he had finally found
one of the wise, one who could answer his heart's deepest question.
Please sir, he asked. tell me the meaning of enlightenment.
The old man smiled, and stopped. Then, fixing his gaze on the youth, he slowly swung the heavy burden
off his back, laid the sack down, and stood up straight.
Ah, I understand, the young man replied. but what comes after enlightenment?
The old man took a deep breath, then swung the heavy sack over his shoulders and continued on his way.

you are here, and here is
PERFECT
I think I learned this lesson the hard way a few years ago when I tried to project my life
experiences on others. As I was going through my own personal development, the love I
experienced for everything around me grew abundant. Almost immediately, I started
sharing my thoughts and feelings with others in the hopes that they would feel all the
positive energy that I felt. Unfortunately, it had the opposite effect of my intention and
created more distance between us.
That’s when I realized that it’s wasn’t my friends that were wrong, but myself. They were
exactly where they should be and I was trying to have them reflect my views back on me
to validate where I was. Many paths exist and you are exactly where you should be.

COMPASSION
through understanding
Humans perceive and react to each other and the world around them exactly as they
should -- based upon their current conceptual model. It is pointless to label or attach
meaning to such actions.
Life conditions force us to adapt to our environment by constructing new, more complex
conceptual models of the world to handle these problems. Spiral dynamics explains this
model as eight stages (colors) of development.

Compassion through Understand3ing MINDFULNESS
Holistic
The best conceptual model
(0.1% pop)
I’ve come across is called
Integrative
spiral dynamics, which
(1% pop)
presents eight stages of
Egalitarianism
development, separated
(10% pop)
into two tiers, with the use
of varying colors.
Individualistic
(30% pop)
MythicOrder
(40% pop)
Egocentric
(20% pop)
Animalistic
(10% pop)
Instinctual
(0.1% pop)
Source: Ken Wilber’s “The Theory of Everything”
Lessons from My 20s

Compassion through Understanding MINDFULNESS
Lessons from My 20s
Holistic
(0.1% pop)
Integrative
(1% pop)
Egalitarianism
(10% pop)
Individualistic
(30% pop)
MythicOrder
(40% pop)
Egocentric
(20% pop)
Animalistic
(10% pop)
Instinctual
(0.1% pop)
The level of basic
survival; food, water,
warmth, sex, and safety
have priority.

Lessons from My 20s
Holistic
(0.1% pop)
Integrative
(1% pop)
Egalitarianism
(10% pop)
Individualistic
(30% pop)
MythicOrder
(40% pop)
Egocentric
(20% pop)
Animalistic
(10% pop)
Instinctual
(0.1% pop)
Magical spirits, good and
bad, curses, and spells
which determine events.

Lessons from My 20s
Holistic
(0.1% pop)
Integrative
(1% pop)
Egalitarianism
(10% pop)
Individualistic
(30% pop)
MythicOrder
(40% pop)
Egocentric
(20% pop)
Animalistic
(10% pop)
Instinctual
(0.1% pop)
First emergence of a self
distinct from the tribe;
powerful, impulsive,
heroic. Feudal lords
protect underlings in
exchange for obedience
and labor.

Lessons from My 20s
Holistic
(0.1% pop)
Integrative
(1% pop)
Egalitarianism
(10% pop)
Individualistic
(30% pop)
MythicOrder
(40% pop)
Egocentric
(20% pop)
Animalistic
(10% pop)
Instinctual
(0.1% pop)
Life has purpose with
outcomes determined by
an all-powerful Other.
This Other enforces
absolutist principles of
"right" and "wrong."

Lessons from My 20s
Holistic
(0.1% pop)
Integrative
(1% pop)
Egalitarianism
(10% pop)
Individualistic
(30% pop)
MythicOrder
(40% pop)
Egocentric
(20% pop)
Animalistic
(10% pop)
Instinctual
(0.1% pop)
The self "escapes" from
the "herd mentality" of
blue, and seeks truth and
meaning through
experimental or objective
reasoning. Highly
achievement oriented,
especially toward
materialistic gains.

Lessons from My 20s
Holistic
(0.1% pop)
Integrative
(1% pop)
Egalitarianism
(10% pop)
Individualistic
(30% pop)
MythicOrder
(40% pop)
Egocentric
(20% pop)
Animalistic
(10% pop)
Instinctual
(0.1% pop)
The human spirit must be
freed from greed;
feelings and caring
supersede cold
rationality. Values
diversity,
multiculturalism,
relativistic value systems

Lessons from My 20s
Holistic
(0.1% pop)
Integrative
(1% pop)
Egalitarianism
(10% pop)
Individualistic
(30% pop)
MythicOrder
(40% pop)
Egocentric
(20% pop)
Animalistic
(10% pop)
Instinctual
(0.1% pop)
TIER 2:
Differences and
pluralities can be
integrated into
interdependent, natural
flows. Knowledge and
competency should
supersede power and
group sensitivity.

Lessons from My 20s
Holistic
(0.1% pop)
Integrative
(1% pop)
Egalitarianism
(10% pop)
Individualistic
(30% pop)
MythicOrder
(40% pop)
Egocentric
(20% pop)
Animalistic
(10% pop)
Instinctual
(0.1% pop)
TIER 2:
The world is a single,
dynamic organism. Self
is part of larger,
conscious, spiritual
whole that also serves
self.

MINDFULNESS
Lessons from My 20s
Compassion through Understanding
Reflection Exercise
Holistic
Integrative
Egalitarianism
Individualistic
MythicOrder
Egocentric
Animalistic
Instinctual
We are all blends of several
colors with varying
intensities.
Take 5-10 minutes to
contemplate where you see
yourself on this spectrum?
Wrong answers don’t exist.

you can’t see the Truth
ONLY A PERSPECTIVE
If Truth is the mountain, we
only see our perspective in
the form of its reflection in
the lake.
The calmer the lake (your
mind), the more accurate
the perspective.

live with
GRATITUDE
If we see this world as sacred, then gratitude comes to us immediately and naturally.
We've been giving the incredible gift of living right now in this moment.
Beauty is all around us and in us -- the touch of a breeze on your face, the sweet taste
of a strawberry, the world we often miss under our feet. Let us give thanks to all the
matter of the universe that makes this life so extraordinary.

MINDFULNESS
embrace
UNCERTAINTY
In 2003, the Hubble Space Telescope pointed its camera 6 at a dark spot in the night’s
sky. It revealed thousands of galaxies... Source: http://www.nasa.gov/mission_pages/hubble/science/xdf.html
Lessons from My 20s

a step back often becomes
A STEP FORWARD
While working on OpenAction, a mapping technology for nonprofits, I felt like my heart
and mind were aligned. Although the business didn't meet the growth trajectory we
expected, with every conversation there was nourishment for the soul.
I contrast this with the more "business"-centric approach of BuzzTable where it seemed
like spiritual capital was exchanged for (potential) financial gain. Whether I sacrificed a
meditation session to ideastorm or failed to hold space for friends, a gain in one area
always felt like a loss in another.
In hindsight I have come to realize that I wasn't losing this personal growth I attained,
but rather expanding the humility I felt grew within me during this seemingly low point in
my spiritual journey.

perfect timing
DOES NOT EXIST
If you are looking to start a meditation or mindfulness practice there is no reason to
wait until you “have more time.” This is a false dichotomy and will never come to the
present moment.
Take 10 minutes out of your day today to sit still. Listen to the world around you --
whether that’s the wind and leaves, car tires against the pavement, or phones ringing
and people walking around the office. After a few minutes you may start to recognize
your own breath.
Pssst... you are meditating.

breathing
EXERCISES
Introduction to Meditation
https://www.youtube.com/watch?v=yMz_UagXkFk
Nadi Shodhana or “Alternate Nostril Breathing”
https://www.youtube.com/watch?v=Xbbr6Udg1UA
Bhastrika Pranayama or “Bellows Breath”
https://www.youtube.com/watch?v=J4nf-NISmJw

deepening your
PRACTICE
I have not experienced the programs below myself. They are here because I am
interested in exploring them and thought they may be helpful to you.
Art of Living - http://www.artofliving.org
Inner Engineering (ISHA Foundation)
Vipassana Meditation (10 day silent retreats) - http://www.dhamma.org/

Lessons from My 20s
part 2: life
HEALTH

Lessons from My 20s 1HEALTH
eat your
SUPER FOODS
Reduce your intake of:
sugars, alcohol, soda,
processed food, gluten,
and animal products.
Increase your intake of:
quality proteins (fish, chicken, eggs, tofu)
fruit (blueberries, bananas)
vegetables (kale, broccoli, avocado, sweet potatoes,
carrots, brussels sprouts)
nuts (peanuts, cashews, walnuts, almonds, pistachios)
seeds (chia, pumpkin, sunflower, hemp)

practice
PREVENTIVE
HEALTH
I’m rarely a procrastinator except when it comes to doctors. It took me thirty years to
finally take responsibility for my own health. Now I’m asking about family history, setting
annual check ups, and doing all I can to maintain my current health.

get your heart rate
UP
Exercise is good for the heart and mind. I’ve always enjoyed lifting weights, but hated
running. I found cycling a few years ago and have biked up to 80 miles in a single day.
If you love running that’s great! For those that don’t, find another activity or two that
you love doing while getting your heart rate up.

HEALTH
detox
ANNUALLY
I started detoxing once a year after the holidays. The 4 start of a new year is a great way
to refresh your mind, body and soul.
Sample 3-Day Detox:
http://vegnews.com/articles/page.do?pageId=5685&catId=2
Lessons from My 20s

HEALTH
YOGA
is more than “stretching”
Yoga has been shown to improve sleep quality1, strengthen 5 your posture and body, and
relieve stress.
I was first exposed to yoga in college, but wrote it off quite easily. A roommate in San
Diego had several yoga-instructor friends who gave me a personal invite to join them in
class.
Almost immediately I felt the benefits. Instead of feeling tired with 8 hours of sleep, I
woke up naturally after 6 with more energy than I was used to.
Source: 1http://www.ncbi.nlm.nih.gov/pubmed/15707256
Lessons from My 20s

Lessons from My 20s
part 2: life
RELATIONSHIPS

Lessons from My 20s 1RELATIONSHIPS
you can’t change others,
ONLY YOURSELF
Many people in relationships want, and often try, to change their partner’s habits to be
more in line with their own “normal.” People do change as they grow, but it will always be
by their own free will. The only thing you can actually control is your ability to accept your
partner for who they are. The “good” with the perceived “bad.” If you can’t, do both of
you a favor and move on.

DEPOSITS
and withdrawals
Although relationships can’t be easily expressed with words or analogies, I will attempt to
draw a comparison to a bank account. The balance is the level of trust you share. To
strengthen the relationship you must make deposits in the form of thoughtful actions.
It’s inevitable that at times you will hurt your partner. As long as you have a positive
balance, you can usually recover. Don’t wait until your account is overdrawn, make a
deposit today. What will it be?

INVEST TIME
in people you care about
I wish I could say this realization came to me early in my twenties, but I’d be mistaken. It’s
always been easy for me to achieve “flow”, the state of immersing oneself in a
passionate activity, where I lose track of time. I was terrible at staying in touch with the
people I cared most about in life. Everyone is busy. If busy keeps you from spending time
with the people you cherish most, what’s the point of being busy to begin with?

NETWORKING
should benefit all parties
If everyone showed up a networking event for selfish reasons then everyone would leave
with less than they arrived with.
I have found that if you spend time trying to figure out how you can help others achieve
their goals, it will often come back to you.
This is especially important if you are starting your first company. You probably feel even
more pressure to turn an immediate ROI on the event. Play the long game instead.

surround yourself with
MENTORS
When I was going through the acquisition with Sysco, I asked the CEO what is one lesson
you would have told your 30-year-old self if you had the chance. He’s response --
“surround yourself with great people.”
I’ve heard that before, but it’s simplicity often causes the lesson to get brushed away.
Find individuals that are where you want to be in 10 years and reach out to them.

Lessons from My 20s
part 2: life
INVESTING

INVESTING PERSONAL GOALS
should dictate your strategy
Money is a store of value, not an end goal. Your investment 1 strategy should be molded
after your lifelong goals. For me, it’s a year of traveling with my fiancé and starting
another company.
Estimate how much of this money you’ll need over the next 3-5 years and set that aside
from what you will invest. Remember, while the stock market typically gains 8%
annually, it may be up or down 20% from year to year.
Lessons from My 20s

INVESTING if you remember one thing,
ASSET ALLOCATION
One year emerging markets may post record returns, 2 while another year it will be large
cap US. The point is, it’s nearly impossible to guess. Once you decide on your stock-to-bond
ratio, maintain this each year while rebalancing annually. This often forces you to
sell high which can help returns.
As you grow older (and wiser) you will adjust your stock-to-bond mix to favor more
stable assets like bonds, value stocks producing dividends and cash.
Lessons from My 20s

INVESTING 2example
ALLOCATION
Lessons from My 20s
Bonds
15%
David Swensen’s Lazy Portfolio
TIPS
15%
David Swensen is CIO of Yale University and author of Unconventional
Success. His “lazy portfolio” uses low-cost, tax-efficient total market
funds, real estate, and inflation-protected securities (TIPS).
Consider checking out A Random Walk
Down Wall Street by Burton Malkiel
and Winning the Loser's Game:
Timeless Strategies for Successful
Investing by Charles D. Ellis. These
two books are where/how I formulated
most of my initial thinking.
US Stocks
30%
Int’l Devlopd
Emerging 15%
5%
Real Estate
20%

INVESTING 3 INDEX FUNDS
Lessons from My 20s
to the finish line
Active portfolio managers (e.g. mutual funds) and wealth managers rarely beat the
market as a whole. A manager may have a few good years, but it's nearly impossible to
consistently beat the market.
Avoid additional fees and unnecessary risk, invest in index funds.

INVESTING dollar-cost
AVERAGING
4 Reduces the impact of market volatility when investing large amounts of capital.
Lessons from My 20s

INVESTING interest
RATES
5 Stocks tend to suffer as interest rates go up, but do well when interest rates are low.
Money tries to find best rate of return.
Lessons from My 20s

INVESTING 6 Source: Ryan Allis’ Lessons from My 20s and http://www.multpl.com/shiller-pe/
STOCKS
The best measure of whether a stock market is overvalued is the Shiller PE Ratio.
The all-time average is 16.55. As of Oct 2014 we’re at 25!
Lessons from My 20s

INVESTING BONDS
• When interest rates rise, bond prices fall to make existing bonds competitive with
new ones being issued at higher rates. When rates • The longer a bond’s term to maturity the greater resulting yield
7 fall, bond prices increase.
the risk and the greater the
• If you are wealthy, you will prefer tax-exempt bonds and stocks that have low
dividend yields but promise long term capital gains
• Avoid junk bonds that may pay in good times, but likely to go sour if the economy
falters
• Inflation is the deadly enemy of the bond investor
Lessons from My 20s

INVESTING REAL ESTATE
You can buy properties, fix them up, and sell them or manage tenants directly as an
active investor OR act as a passive investor giving up hassles of managing tenants, toilets and trash.
8 some of the return with the
There are 2 ways to invest as a passive investor:
Lessons from My 20s
Short Term Long Term
•Also known as hard money loans
•Typical holding period is 6-18mo
•8-12% interest rate most common
•Require borrower with great credit,
previous track record, and first trust deed
(your interest is secured by property in
first position)
•Seek loan-to-value < 75%
•Unlike debt financing, here you would be an equity holder. You’ll
take on more risk, but potentially higher returns
•Typical holding period is 3-10 years
•Work with sponsor to acquire property in buy-and-hold strategy
•You are entitled to share of cash-flow from rents as well as share
of proceeds when property is eventually sold (appreciation)
•Unlike stocks which are liquid (you could sell today), real estate is
very illiquid and you probably won’t be able to pull your money out
for many years.

9
INVESTING
India are at 8%. COMMODITIES
Commodities include energy (crude oil, natural gas), industrial metals (aluminum,
copper), precious metals (gold, silver), agriculture (coffee, corn, sugar) and livestock.
Some investors, like Warren Buffet, avoid this asset class because it’s based on what
people are willing to pay for it in the future and tied to the dollar. However, given that
commodities have dropped 30% from 2009-2014 due to the strong equities markets
and dollar, I personally see some upside over the next few years.
Benefits of having commodities in your portfolio:
• Hedge against currency devaluation, inflation or deflation
• In the extreme, yet unlikely scenario of political unrest, commodities like gold are seen as value
protection
• Interesting to note: France, Italy, Germany, US have 65% of foreign reserves in gold; Russia and
Lessons from My 20s

INVESTING 10 peer-to-peer
LENDING
LendingClub is the largest based on loan volume and revenue, followed by Prosper.
Collectively, they’ve serviced almost 200,000 loans.
While it seems advantageous for both borrowers (better rates than traditional banks) and
lenders (higher returns compared to savings account), these loans are unsecured personal
loans. That means, if the borrower defaults, there is not much you can do as a lender to
get your money back. For that reason, and the fact that 90% of the “best” loans are taken
by hedge funds before making it to individual investors I tend to avoid this vehicle.
I prefer hard money loans instead. These loans are secured to a hard asset like real
estate. In the event that a borrower of this type of loan defaults, you will have the property
as collateral.
Lessons from My 20s

Lessons from My 20s
part 2: life
GOALS

GOALS
When I do this again at 40,
how do I hope to
define my 30s?
Lessons from My 20s

GOALS
GOALS
help you check in with yourself
Lessons from My 20s

GOALS
GOALS
help you check in with yourself
SURPRISINGLY, VERY FEW SET THEM
AND CHECK IN EACH YEAR
Lessons from My 20s

Lessons from My 20s
&
GOALS
Mine are driven by 3 things:
MIND
BODY SOUL

GOALS
Lessons from My 20s
mind.
knowledge
body.
health
soul.
meditation
(Hopefully) I’m here

GOALS
A good way I’ve found to
ALIGN MY GOALS,
is to think of them as 6 themes
Lessons from My 20s

GOALS
A good way I’ve found to
ALIGN MY GOALS,
is to think of them as 6 themes
Lessons from My 20s
HEALTH TRAVEL &
ADVENTURE
WORK
FINANCES RELATIONSHIP GLOBAL
IMPACT

GOALS
Lessons from My 20s
HERE ARE MINE...

GOALS
Lessons from My 20s
NOW IT’S YOUR TURN...

GOALS
GET A PEN & PAPER
START WITH A BLANK PAGE...
WRITE “LIFE GOALS” AT THE TOP
THEN SPEND 10 MINUTES
THINKING ABOUT THE 6 THEMES
WHAT DO YOU WANT TO ACHIEVE
BEFORE LEAVING THIS PLANET?
Lessons from My 20s

GOALS
DO THE SAME FOR GOALS AT...
10 YEARS, THEN 1 YEAR
SPEND 5 MINUTES EACH ON THESE
Lessons from My 20s

GOALS
NOW CREATE A 90 DAY ACTION PLAN
TO START TACKLING YOUR 1 YEAR GOALS
Lessons from My 20s

GOALS
FINALLY,
CREATE YOUR PURPOSE STATEMENT
WHAT MAKES YOU COME ALIVE?
THINK OF WORDS YOU’D LIKE PEOPLE TO
USE TO DESCRIBE YOU.
Lessons from My 20s

GOALS
NOW, TAKE ALL THESE NOTES
AND ADD THEM TO THE NEXT SLIDE
PRINT IT OUT. HANG IT. SHARE IT.
Lessons from My 20s

LIFE PLAN OF ______________________
LIFE PURPOSE
AREAS OF FOCUS
health, adventure/travel, work, finances, relationship, impact
LIFETIME GOALS 10 YEAR GOALS
1 YEAR GOALS 90 DAY ACTION PLAN
FIRST CREATED ON ______________. LAST UPDATED ON ______________.

Lessons from My 20s
hope this was as helpful to you
as it was therapeutic for me =)
I want to thank the following people for helping review this before I made it public:
Jenn Harn, Xander Page, Aaron Rankin, Amit Kumar, Jon Howard, Jay Shek,
Mike Wenger, Arjun Dev Arora, Samantha Smith, Jared Paul and Spencer Ton
Get in touch with me: john@buzztable.com - @worldlyjohn

Tangible Lessons from My 20s by John Brennan

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Tangible Lessons from My 20s by John Brennan