Ray Dalio's super-effective roadmap 

Ray Dalio's $22 billion net worth ranks him 36th globally. From 1975 to 2011, he built the world's most successful hedge fund, never losing more than 4% from 1991 to 2020. (and only doing so during 3 calendar years). 

Dalio describes a 5-step process in his best-selling book Principles. It's the playbook he's used to build his hedge fund, beat the markets, and face personal challenges. 

This 5-step system is so valuable and well-explained that I didn't edit or change anything; I only added my own insights in the parts I found most relevant and/or relatable as a young entrepreneur. The system's overview: 

1. Have clear goals 

2. Identify and don’t tolerate problems 

3. Diagnose problems to get at their root causes 

4. Design plans that will get you around those problems 

5. Do what is necessary to push through the plans to get results 

If you follow these 5 steps in a virtuous loop, you'll almost always see results. Repeat the process for each goal you have. 

1. Have clear goals 

a) Prioritize: You can have almost anything, but not everything. 

I started and never launched dozens of projects for 10 years because I was scattered. I opened a t-shirt store, traded algorithms, sold art on Instagram, painted skateboards, and tinkered with electronics. I decided to try blogging for 6 months to see where it took me. Still going after 3 years. 

b) Don’t confuse goals with desires. 

A goal inspires you to act. Unreasonable desires prevent you from achieving your goals. 

c) Reconcile your goals and desires to decide what you want. 

d) Don't confuse success with its trappings. 

e) Never dismiss a goal as unattainable. 

Always one path is best. Your perception of what's possible depends on what you know now. I never thought I'd make money writing online so quickly, and now I see a whole new horizon of business opportunities I didn't know about before. 

f) Expectations create abilities. 

Don't limit your abilities. More you strive, the more you'll achieve. 

g) Flexibility and self-accountability can almost guarantee success. 

Flexible people accept what reality or others teach them. Self-accountability is the ability to recognize your mistakes and be more creative, flexible, and determined. 

h) Handling setbacks well is as important as moving forward. 

Learn when to minimize losses and when to let go and move on. 

2. Don't ignore problems 

a) See painful problems as improvement opportunities. 

Every problem, painful situation, and challenge is an opportunity. Read The Art of Happiness for more. 

b) Don't avoid problems because of harsh realities. 

Recognizing your weaknesses isn't the same as giving in. It's the first step in overcoming them. 

c) Specify your issues. 

There is no "one-size-fits-all" solution. 

d) Don’t mistake a cause of a problem with the real problem. 

"I can't sleep" is a cause, not a problem. "I'm underperforming" could be a problem. 

e) Separate big from small problems. 

You have limited time and energy, so focus on the biggest problems. 

f) Don't ignore a problem. 

Identifying a problem and tolerating it is like not identifying it. 

3. Identify problems' root causes 

a) Decide "what to do" after assessing "what is." 

"A good diagnosis takes 15 to 60 minutes, depending on its accuracy and complexity. [...] Like principles, root causes recur in different situations. 

b) Separate proximate and root causes. 

"You can only solve problems by removing their root causes, and to do that, you must distinguish symptoms from disease." 

c) Knowing someone's (or your own) personality can help you predict their behavior. 

4. Design plans that will get you around the problems 

a) Retrace your steps. 

Analyze your past to determine your future. 

b) Consider your problem a machine's output. 

Consider how to improve your machine. It's a game then. 

c) There are many ways to reach your goals. 

Find a solution. 

d) Visualize who will do what in your plan like a movie script. 

Consider your movie's actors and script's turning points, then act accordingly. The game continues. 

e) Document your plan so others can judge your progress. 

Accountability boosts success. 

f) Know that a good plan doesn't take much time. 

The execution is usually the hardest part, but most people either don't have a plan or keep changing it. Don't drive while building the car. Build it first, because it'll be bumpy. 

5. Do what is necessary to push through the plans to get results 

a) Great planners without execution fail. 

Life is won with more than just planning. Similarly, practice without talent beats talent without practice. 

b) Work ethic is undervalued. 

Hyper-productivity is praised in corporate America, even if it leads nowhere. To get things done, use checklists, fewer emails, and more desk time. 

c) Set clear metrics to ensure plan adherence. 

I've written about the OKR strategy for organizations with multiple people here. If you're on your own, I recommend the Wheel of Life approach. Both systems start with goals and tasks to achieve them. Then start executing on a realistic timeline. 

If you find solutions, weaknesses don't matter. 

Everyone's weak. You, me, Gates, Dalio, even Musk. Nobody will be great at all 5 steps of the system because no one can think in all the ways required. Some are good at analyzing and diagnosing but bad at executing. Some are good planners but poor communicators. Others lack self-discipline. 

Stay humble and ask for help when needed. Nobody has ever succeeded 100% on their own, without anyone else's help. That's the paradox of individual success: teamwork is the only way to get there. 

Most people won't have the skills to execute even the best plan. You can get missing skills in two ways: 

1. Self-taught (time-consuming) 

2. Others' (requires humility) light

On knowing what to do with your life 

“Some people have good mental maps and know what to do on their own. Maybe they learned them or were blessed with common sense. They have more answers than others. Others are more humble and open-minded. […] Open-mindedness and mental maps are most powerful.” — Ray Dalio 

I've always known what I wanted to do, so I'm lucky. I'm almost 30 and have always had trouble executing. Good thing I never stopped experimenting, but I never committed to anything long-term. I jumped between projects. I decided 3 years ago to stick to one project for at least 6 months and haven't looked back. 

Maybe you're good at staying focused and executing, but you don't know what to do. Maybe you have none of these because you haven't found your purpose. Always try new projects and talk to as many people as possible. It will give you inspiration and ideas and set you up for success. 

There is almost always a way to achieve a crazy goal or idea. 

Enjoy the journey, whichever path you take.

Calmness is a vital life skill.

It aids communication. It boosts creativity and performance.

I've studied calm people's habits for years. Commonalities:

Have mastered the art of self-humor.

Protectors take their job seriously, draining the room's energy.

They are fixated on positive pursuits like making cool things, building a strong physique, and having fun with others rather than on depressing influences like the news and gossip.

Every day, spend at least 20 minutes moving, whether it's walking, yoga, or lifting weights.

Discover ways to take pleasure in life's challenges.

Since perspective is malleable, they change their view.

Set your own needs first.

Stressed people neglect themselves and wonder why they struggle.

Prioritize self-care.

Don't ruin your life to please others.

Make something.

Calm people create more than react.

They love creating beautiful things—paintings, children, relationships, and projects.

Don’t hold their breath.

If you're stressed or angry, you may be surprised how much time you spend holding your breath and tightening your belly.

Release, breathe, and relax to find calm.

Stopped rushing.

Rushing is disadvantageous.

Calm people handle life better.

Are aware of their own dietary requirements.

They avoid junk food and eat foods that keep them healthy, happy, and calm.

Don’t take anything personally.

Stressed people control everything.

Self-conscious.

Calm people put others and their work first.

Keep their surroundings neat.

Maintaining an uplifting and clutter-free environment daily calms the mind.

Minimise negative people.

Calm people are ruthless with their boundaries and avoid negative and drama-prone people.

An email capturing Steve Jobs's philosophy.

Steve Jobs may have been the most inspired and driven entrepreneur.

He worked on projects because he wanted to leave a legacy.

Steve Jobs' final email to himself encapsulated his philosophy.

After his death from pancreatic cancer in October 2011, Laurene Powell Jobs released the email. He was 56.

Read: Steve Jobs by Walter Isaacson (#BestSeller)

The Email:

September 2010 Steve Jobs email:

“I grow little of the food I eat, and of the little I do grow, I do not breed or perfect the seeds.” “I do not make my own clothing. I speak a language I did not invent or refine,” he continued. “I did not discover the mathematics I use… I am moved by music I did not create myself.”

Jobs ended his email by reflecting on how others created everything he uses.

He wrote:

“When I needed medical attention, I was helpless to help myself survive.”

The Apple co-founder concluded by praising humanity.

“I did not invent the transistor, the microprocessor, object-oriented programming, or most of the technology I work with. I love and admire my species, living and dead, and am totally dependent on them for my life and well-being,” he concluded.

The email was made public as a part of the Steve Jobs Archive, a website that was launched in tribute to his legacy.

Steve Jobs' widow founded the internet archive. Apple CEO Tim Cook and former design leader Jony Ive were prominent guests.

Steve Jobs has always inspired because he shows how even the best can be improved.

High expectations were always there, and they were consistently met.

We miss him because he was one of the few with lifelong enthusiasm and persona.

SaaS spending is 40/40/20. 40% of operating expenses should be R&D, 40% sales and marketing, and 20% G&A. We wanted to see the statistics behind the rules of thumb. Since October 2017, 73 SaaS startups have gone public. Perhaps the rule of thumb should be 30/50/20. The data is below.

30/50/20. R&D accounts for 26% of opex, sales and marketing 48%, and G&A 22%. We think R&D/S&M/G&A should be 30/50/20.

There are outliers. There are exceptions to rules of thumb. Dropbox spent 45% on R&D whereas Zoom spent 13%. Zoom spent 73% on S&M, Dropbox 37%, and Bill.com 28%. Snowflake spent 130% of revenue on S&M, while their EBITDA margin is -192%.

G&A shouldn't stand out. Minimize G&A spending. Priorities should be product development and sales. Cloudflare, Sendgrid, Snowflake, and Palantir spend 36%, 34%, 37%, and 43% on G&A.

Another myth is that COGS is 20% of revenue. Median and averages are 29%.

Where is the profitability? Data-driven operating income calculations were simplified (Revenue COGS R&D S&M G&A). 20 of 73 IPO businesses reported operational income. Median and average operating income margins are -21% and -27%.

As long as you're growing fast, have outstanding retention, and marquee clients, you can burn cash since recurring income that doesn't churn is a valuable annuity.

The data was compelling overall. 30/50/20 is the new 40/40/20 for more established SaaS enterprises, unprofitability is alright as long as your business is expanding, and COGS can be somewhat more than 20% of revenue.

I've been pondering product strategy and how to articulate it. Frameworks helped guide our thinking.

If your teams aren't working together or there's no clear path to victory, your product strategy may not be well-articulated or communicated (if you have one).

Before diving into a product strategy's details, it's important to understand its role in the bigger picture — the pieces that move your organization forward.

the overall picture

A product strategy is crucial, in my opinion. It's part of a successful product or business. It's the showpiece.

To simplify, we'll discuss four main components:

1. Vision

2. Product Management

3. Goals

4. Roadmap

Vision

Your company's mission? Your company/product in 35 years? Which headlines?

The vision defines everything your organization will do in the long term. It shows how your company impacted the world. It's your organization's rallying cry.

An ambitious but realistic vision is needed.

Without a clear vision, your product strategy may be inconsistent.

Product Management

Our main subject. Product strategy connects everything. It fulfills the vision.

In Part 2, we'll discuss product strategy.

Goals

This component can be goals, objectives, key results, targets, milestones, or whatever goal-tracking framework works best for your organization.

These product strategy metrics will help your team prioritize strategies and roadmaps.

Your company's goals should be unified. This fuels success.

Roadmap

The roadmap is your product strategy's timeline. It provides a prioritized view of your team's upcoming deliverables.

A roadmap is time-bound and includes measurable goals for your company. Your team's steps and capabilities for executing product strategy.

If your team has trouble prioritizing or defining a roadmap, your product strategy or vision is likely unclear.

Formulation of a Product Strategy

Now that we've discussed where your product strategy fits in the big picture, let's look at a framework.

A product strategy should include challenges, an approach, and actions.

Challenges

First, analyze the problems/situations you're solving. It can be customer- or company-focused.

The analysis should explain the problems and why they're important. Try to simplify the situation and identify critical aspects.

Some questions:

• What issues are we attempting to resolve?

• What obstacles—internal or otherwise—are we attempting to overcome?

• What is the opportunity, and why should we pursue it, in your opinion?

Decided Method

Second, describe your approach. This can be a set of company policies for handling the challenge. It's the overall approach to the first part's analysis.

The approach can be your company's bets, the solutions you've found, or how you'll solve the problems you've identified.

Again, these questions can help:

• What is the value that we hope to offer to our clients?

• Which market are we focusing on first?

• What makes us stand out? Our benefit over rivals?

Actions

Third, identify actions that result from your approach. Second-part actions should be these.

Coordinate these actions. You may need to add products or features to your roadmap, acquire new capabilities through partnerships, or launch new marketing campaigns. Whatever fits your challenges and strategy.

Final questions:

• What skills do we need to develop or obtain?

• What is the chosen remedy? What are the main outputs?

• What else ought to be added to our road map?

Put everything together

… and iterate!

Strategy isn't one-and-done. Changes occur. Economies change. Competitors emerge. Customer expectations change.

One unexpected event can make strategies obsolete quickly. Muscle it. Review, evaluate, and course-correct your strategies with your teams. Quarterly works. In a new or unstable industry, more often.

How did his money blind me?

Like most fledgling entrepreneurs, I wanted a mentor. I met as many nearby folks with "entrepreneur" in their LinkedIn biographies for coffee.

These meetings taught me a lot, and I'd suggest them to any new creator. Attention! Meeting with many experienced entrepreneurs means getting contradictory advice. One entrepreneur will tell you to do X, then the next one you talk to may tell you to do Y, which are sometimes opposites. You'll have to chose which suggestion to take after the chats.

I experienced this. Same afternoon, I had two coffee meetings with experienced entrepreneurs. The first meeting was with a billionaire entrepreneur who took his company public.

I met him in a swanky hotel lobby and ordered a drink I didn't pay for. As a fledgling entrepreneur, money was scarce.

During the meeting, I demoed the software I'd built, he liked it, and we spent the hour discussing what features would make it a success. By the end of the meeting, he requested I include a killer feature we both agreed would attract buyers. The feature was complex and would require some time. The billionaire I was sipping coffee with in a beautiful hotel lobby insisted people would love it, and that got me enthusiastic.

The second meeting was with a young entrepreneur who had recently raised a small amount of investment and looked as eager to pitch me as I was to pitch him. I forgot his name. I mostly recall meeting him in a filthy coffee shop in a bad section of town and buying his pricey cappuccino. Water for me.

After his pitch, I demoed my app. When I was done, he barely noticed. He questioned my customer acquisition plan. Who was my client? What did they offer? What was my plan? Etc. No decent answers.

After our meeting, he insisted I spend more time learning my market and selling. He ignored my questions about features. Don't worry about features, he said. Customers will request features. First, find them.

Putting your faith in results over relevance

Problems plagued my afternoon. I met with two entrepreneurs who gave me differing advice about how to proceed, and I had to decide which to pursue. I couldn't decide.

Ultimately, I followed the advice of the billionaire.

Obviously.

Who wouldn’t? That was the guy who clearly knew more.

A few months later, I constructed the feature the billionaire said people would line up for.

The new feature was unpopular. I couldn't even get the billionaire to answer an email showing him what I'd done. He disappeared.

Within a few months, I shut down the company, wasting all the time and effort I'd invested into constructing the killer feature the billionaire said I required.

Would follow the struggling entrepreneur's advice have saved my company? It would have saved me time in retrospect. Potential consumers would have told me they didn't want what I was producing, and I could have shut down the company sooner or built something they did want. Both outcomes would have been better.

Now I know, but not then. I favored achievement above relevance.

Success vs. relevance

The millionaire gave me advice on building a large, successful public firm. A successful public firm is different from a startup. Priorities change in the last phase of business building, which few entrepreneurs reach. He gave wonderful advice to founders trying to double their stock values in two years, but it wasn't beneficial for me.

The other failing entrepreneur had relevant, recent experience. He'd recently been in my shoes. We still had lots of problems. He may not have achieved huge success, but he had valuable advice on how to pass the closest hurdle.

The money blinded me at the moment. Not alone So much of company success is defined by money valuations, fundraising, exits, etc., so entrepreneurs easily fall into this trap. Money chatter obscures the value of knowledge.

Don't base startup advice on a person's income. Focus on what and when the person has learned. Relevance to you and your goals is more important than a person's accomplishments when considering advice.