The Decamillionaire Trail Guide

A free workbook for the $10M+ net worth terrain, by Richard C. Wilson. 19 years running the Family Office Club, 300 in-person events, 1,500 investor talks heard from the stage, 47 billionaire interviews.

This is the free public edition and nothing in it is gated. No email, no account, no membership. Print it and work through it as a workbook, which is how it is meant to be used.

If you do not build your financial IQ faster than your net worth many around you will volunteer to correct that equation to bring it right into balance. Normal pedestrians who are not founders, not decamillionaires, and not on their way there cannot relate to the cognitive load that is your norm, and what others don't understand they often criticize or distance themselves from.

When you realize you could retire, but what is the point of doing so, or that while others may be comfortable you know you are just getting started, or when you are confident you could do 100x more yet others say wow, what a great business you have built, you are going to enjoy this guide. You must set a standard of excellence to scale to $10M and higher, after setting it you have to hold the line, mediocrity and complacency is the enemy.

Who This Trail Guide Is For. The Decamillionaire Trail Guide™ is designed for those navigating the $10M+ net worth terrain, where capital compounds faster, errors are more costly, and reputation and structure matter more than effort. I document here what must be true if you want to be a high velocity founder following the path of patterns which keep repeating among family offices. Some of what works to grow to $1M or $5M net worth breaks above those levels. We will cover what to avoid, stop doing and how to not lose wealth once reaching new levels. You will notice themes around strategic levers, positioning, focusing your energy, and being intentional in ways others are not, these are repeated on purpose as they are the patterns we keep noticing.

This guide is for:

Founders, investors, and capital raisers who want to close larger, more consistent checks from decamillionaires by understanding how capital at this level evaluates trust, leverage, risk, and alignment.

Entrepreneurs and deal makers actively working to become decamillionaires, who want a clearer, more disciplined path that avoids common traps and prioritizes compounding over complexity.

Individuals already at $10M+ net worth who want to protect what they have built, preserve optionality, and continue growing intelligently without unnecessary risk or operational drag.

I do not have all of the answers but after building my business from being broke to becoming a decamillionaire in 2015, hearing 1,500 investors speak at our 300 live events the last 19 years, and reading 245 billionaire books, I have figured out a few parts of the equation. I script every discussion panel question at every event we host based on what I want to learn, I do every billionaire interview for Billionaires.com so I can selfishly grow (and position myself), as I share those insights with others (reciprocation at work).

So far I have read 135 out of the 245 books authored by billionaires, here is my list of the top 10 most powerful of those. I have found printing out and reviewing my 1 page prefrontal cortex dashboard daily, choosing a single video on YouTube to watch daily, and working out daily keeps me focused. Give yourself permission to be extreme, many will not like your focus but you are not optimizing to please everyone, you are optimizing your ability to scale your net worth while having an exciting, fulfilling ultra-healthy life.

Purpose. This Trail Guide is built for those who prefer decision frameworks over tactics, precision over volume, and long-term leverage over short-term wins. This guide is not for beginners, doesn't provide generic wealth tips, lifestyle advice or mass-market strategies. We do not recommend chasing quick wins, speculation, or get rich quick claims. It is designed for those willing to choose their terrain deliberately, avoid known failure zones, and make decisions that hold up over a 10-year horizon.

How to Use This Trail Guide. The Decamillionaire Trail Guide™ is not designed to be read once or followed sequentially. It is a navigation instrument meant to be revisited as your capital, opportunities, and constraints evolve. Each segment defines the conditions that must be true for sustained wealth compounding at higher levels. Use this guide to identify where you are experiencing friction, misalignment, or risk, then focus only on the segment most relevant to your current terrain. Revisit this guide 2x a year as you grow new divisions or form new joint ventures.

To add some context to who I am and why I put this together, I have spent 19 years running our investor club, hosted 300+ events, interviewed 47 billionaires (one pictured here to the right), I have listened to 1,500 investors talks on stage, created 50+ artificial intelligence tools, read 135 books authored by billionaires, and these are the patterns that keep repeating.

Disclaimer. For informational purposes only, I am not your attorney, physician, financial, tax or wealth advisor.

Maximum ROI. You will get 3x more out of this guide if you go slow, watch the videos, use the AI tools, and complete this printed out as a workbook. This is not about rushing through the guide but thinking on each major point and acting on it to maximize the impact.

Your Assistant. Family Office Club members also get an AI assistant built on this guide called Decamillionaire Sherpa. You do not need it to use this guide, everything here works on its own.

Segment 1: Strategic Positioning & Market Control

Choose the terrain where opportunities compound in your favor, and exit everything else.

After $10M, positioning matters more than effort. Most capable investors, founders, and capital raisers do not stall because they lack intelligence, access, or ambition ... they stall because they operate across too many terrains at once, diluting leverage, credibility, and investor conviction.

This block forces clarity around where you play, how you win, and why capital should seek you out. It is designed to help you stop chasing opportunities and instead own a narrow battlefield where trust compounds, deal flow improves, and strategic advantage becomes difficult to replicate. If this block is executed correctly, everything downstream becomes easier ... capital raises, partnerships, visibility, and long-term wealth velocity. Clarity on your powerful vision is required for rapid execution.

Decamillionaire Resources. In each section we will provide a collection of resources in various formats to help go deeper on related topics to each segment of the trail guide. This allows us to keep this guide concise without it growing to 150-200 pages and we know most decamillionaire types are very busy and it is more practical to consume bite size PDFs, videos, audio interviews, etc. than a long book.

AI Powered Guidance + Compass Tools. : For this segment our Choke Point Machine, I know Sun Tzu, and our 1st Principles Problem Solver tools may be most helpful. Our tools are built off of our proprietary data including transcripts from 1,500 investors who have spoken at our 300+ events over 19 years.

What is a market niche/position so valuable, not already crowded, and aligned with your strengths, experience and natural advantages that even if it took 3-5 or 7+ years to obtain it would transform your business?

The 10 Strategic Positioning Moves. Put a checkmark next to each strategy you have in place, and a priority #1-#3 on what 3 you need to focus on right now to build and protect your wealth.

The goal is to become a force of nature, pursue bold exponential results, constantly cut losses and when you have an edge exploit it massively.

What are 3 strategic choke points you should aim to acquire next? (think IP, market positioning assets, AI tools, resources, domain names, real estate, relationships, agreements, partnerships) 1)

2)

3) [Video / AI Tool]

Distribution Control. We had a Shark from Shark Tank speak on stage at our 800 person investor club summit last month, his whole talk emphasized one point. He essentially has been able to gain distribution, see a niche and get influencers, social media, TV or other channels of distribution secured to grow sales to billions in revenue across his ventures. This can be done with capital, strategic choke points, and it applies to raising capital, seeing exclusively deals, gaining clients, marketing, sales, building your IP stack, etc.

What distribution channels do you control, and which do you need to in the future?

What is your 1 liner?

[Video / AI Tool]

Strategic Thinking Time. Sit quietly with a notebook for 1 hour with no cell phone, and think through this strategic block, the more you invest energy into superior positioning through branding, thought leadership, joint ventures, strategic assets, and niche sandbox domination the better you will do.

Before moving on review this segment one more time ... what resource above or AI tool do you need to send to your team?

What do you need to set a reminder on or take action on now to get value out of this part of the guide before rushing on to the next segment?

Additional Notes

Segment 2: Extreme Focus + High Velocity

Install a new approach that drives consistent, compounding results, increase velocity

This segment is not about productivity so much as execution velocity in the face of increasing complexity. This segment helps you stay decisive, agile and dangerous as scale increases, you must protect momentum vs. focus on maximizing output.

Extreme Focus Timers. One strategy I picked up from a centimillionaire is to set timers when you have a critical task, start it as you engage and stop it if you get distracted, shoot for 45-90 min sessions of laser-focused work.

The #1 most powerful strategy for keeping your goals top of mind and mental models front and center is to create your 1 page cheat sheet of where you are going and how you are going to get there. See instructions on creating yours here, and a template for you to use here while doing so. Stop and put this into place right now.

Time Management. Velocity requires you to be distracted less, waste less time, focus uninterrupted for longer periods of time on your biggest opportunities. To get more done you have to eliminate sources of cognitive load that degrade judgement, say no more, and reduce decision distortion caused by social approval bias, or they will eat you and your time alive. You must ask for an agenda when someone wants to meet, use audio notes instead of phone calls many times, wake early, and be consistently decisive. Clarity multiplies action, have a crystal clear vision, practice speed of implementation, and invest in keeping the best talent on your team, so they are not seen as a cost. This guide was completed using this strategy.

Decamillionaire Resources. Please review the below resources to add context to this segment:

High Velocity Audit. Where are 3 areas you are moving too slow?

Simplicity is the ultimate form of sophistication. What is the #1 extreme focus you need right now?

What is the #1 thing distracting you from extreme focus?

You have to be high energy and high action, I have never met a slow moving decamillionaire, as David Goggins says do not get too comfortable or "civilized" as he calls it. Where are you too civilized?

Do you send 10x as many audio notes as you have phone calls per day?

What is the strategic sandbox or keyword phrase you want to dominate long-term?

AI Powered Guidance + Compass Tools. You may find our Extreme Focus Finder to help you find what to focus on, Mental Model Intelligence to help you adapt new mental models from a library of 2,500 of them, and Billionaire Collective Intelligence which was built off of the public talks and our exclusive interviews with 1,050 billionaires.

Most founders who are not high velocity are too slow to make decisions, too unclear on where they are headed to dig in, and change their minds and focus too frequently or don't identify valuable enough scalable niches. Only work on things which are exciting, exponential, and if you could pull off would transform your life or business. Everything else is a distraction and why you are not high velocity.

What are the things you need to delete and remove to have extreme focus?

What is profitable to do but you just have to say no because of other commitments and really go all in one where you know extreme focus will pay off?

Look at what you need to get done today, set a 45-90 minute timer as suggested for extreme focus and do this 1-3x a day, set a reminder to do it if needed so you become a high velocity founder. If you prioritize the non-urgent and work on it with great focus, you move things forward strategically at a rapid pace.

In Physics a core principle is that if you drop mass you gain velocity, so if you are not growing fast enough focus more. Many above $10M net worth lose speed due to unclear or overly broad terrain. Ask yourself, what narrow terrain should you dedicate yourself to owning completely?

Additional Notes

Segment 3: Capital Strategy & Deal Architecture

Raise capital and partner consistently by mastering investor psychology and deal structure.

In my book Capital Raising I lay out a 5 step system for raising capital, I also have a 17 episode mini-series called the $100M Rainmaker Series. If you are a member in the Family Office Club ... navigate to the 100 CapitalCon talks in our member portal, each of these 10 minute talks are from experts who have raised $100M+ or $1B+. If you watch those as well as our Capital Raiser Bootcamp workshops you will have a clear edge over others raising capital in your niche.

Top 5 Mistakes Costing $1M+. Almost everyone that raises capital fails to put into place half or more of these items

Decamillionaire Resources. Please review these resources for more context

AI Powered Guidance + Compass Tools. For this segment use Clara: Your Investor Pitch Architect, Pitch Score to rate your pitch materials and identify 25 ways to improve them, and our One-Liner Tool to craft a powerful single sentence pitch.

Structure Strategies. If you raise capital using a single structure and go around asking every investor to be an LP in your blind pool investment fund, you will raise 5% of the capital you could have most likely offering other options. We have 3-4 sentences to talk about it here, but talk about it for 3-4 hours at some of our investor accelerator events. You need to know what a direct deal would look like vs. a fund, how something could be structured as a joint venture or Co-GP deal, if gross revenue royalties could be used in your industry, or what deal terms an anchor investor would want to see to take 20-100% of the deal. Get investor capital back first, then win together and win most after they have gotten a great return.

The more simple, balanced, unique, and transparent the structure the better. Investors want asymmetrical returns, a great potential return for a relatively low level of risk. We have shared 6 resources in the table above but our deal structure strategies webinar is worth reviewing, and the next time you buy or sell an asset try our Deal Structure Ninja AI tool as well.

What structure would help you grow 2x as quickly and attract powerful partners?

3 Trust Curves. Deals get done when there is extremely high trust in one of these areas or high enough trust across three components of Team, Industry, and the Opportunity. If someone knows the team very well, they may consider investing in an industry they don't generally like or a deal they are not familiar with or haven't seen in person. If you pitch investors however who don't know you, the industry, and are not local to the opportunity you are wasting your time.

Which of the 3 trust curves do you think is weak or not focused on enough in your materials or pitch that you need to work on?

How deep have you gone down the deal structuring rabbit hole? If you have not spent 10-20+ hours watching videos, training, re-negotiating deal terms every year for several years you are a relative infant in this area (we all are in many areas).

Additional Notes

Segment 4: Reputation Capital & Strategic Visibility

Grow investor trust and deal flow by shaping how the market perceives you. Position yourself as the credible, strategic partner others want to co-invest with ... before they ever meet you.

Perception is often taken as reality, and Dr. Robert Cialdini has scientifically proven that if you build an authority position, add value first through thought leadership, and can position yourself as a top credible expert in a clear niche position you will grow faster.

In your market niche, who is the most helpful, prolific, well-known, and has the best reputation? Can you partner with them, add them to your board, or what can you learn from them? Influence and authority positioning produce a currency of exclusive proprietary deal flow, and opportunity sets nobody else gets to see.

Meditating on your powerful position pays massive dividends, change your brand to grow interest in your platform, everything from your brand name, one-liner, and social updates should draw in opportunity.

Brand. If someone reads JUST your brand name, do they have any clue what you do or do they have ask what the name means, now just guess that is your last name, or have to ask what that Greek god stands for? 95% of companies fail this simple test, while the billionaire founder of Paychex says he will not invest $1 with any CEO that doesn't rebrand to something powerful and effective in drawing in business, it is too high of leverage of a tweak not to. Actions Needed?

Powerful Positioning. You want to craft a powerful position that systematically attracts pre-qualified opportunities and partners. The founders and investors who get to see deals first, exclusively and at better valuations will compound their wealth faster and this is key to adding 10s of millions of dollars to your net worth, it increases the surface area of your likelihood of "getting lucky."

Decamillionaire Resources. Please review these resources for more context

AI Powered Guidance + Compass Tools. To create a brand that brings in business and sweats for you leverage our Brand Creator AI Tool, try out Coffee with Richard Wilson, and leverage our Investor Super Intelligence platform through our Guide Tool.

What publicly traded companies, industry titans or $1B+ balance sheets could you partner with or close a deal with to massively boost your credibility?

What is the unique set of skills, capital, distribution access, or other resources that you bring to founders in your target industry of investment, or growth? What can you offer in a sentence that will get them to lean forward and want to work with you?

Systematic Deal Origination. What is the most profitable target geography to focus on when acquiring a competitor, a strategic asset or type of real estate? What size are these assets or companies? Use this focused approach to build out 100-300 targeted leads and use your materials and 1 liner on how you add value to originate new opportunities by reaching out to owners of those assets over and over until they reply. Who can help you put this process in place?

What are ways you can get in front of and reach out to 10x as many owners in your niche? Consider associations, non-profits, social media, email lists, publications, expos/conferences, and direct reach outs.

Additional Notes

Segment 5: Capital Allocation & Wealth Multiplication

Build lasting wealth through structured reinvestment, smart diversification, and capital flywheels.

Wealth advisors typically say two things 1) Letting us manage all of your money is in your best interest and 2) Diversification is the only strategy you want and need. The $10M+ and $100M+ clients I work with manage their 3 portfolio in 3 segments 1) Diversified Public Markets Exposure 2) Direct Real Estate + Private Equity Deals for Diversified and 3) Niche Focus in 1-3 Areas to Scale Wealth.

Bucket 1 is the only area wealth advisors assist in typically, bucket 2 can be helped by some private syndicated transactions through large banks and platforms but 80-90% of what the ultra-wealthy invest in here is sourced via their network, local community, and areas they have selected to focus on (think cities/states and RE/PE food groups). Bucket 3 is where they try to make $1 turn into $10 or $100, it is their offensive game, even billionaires should be playing just 1-3 games of monopoly at a time and if you play offense in more than 1 area the 2-3 better be related.

AI Powered Guidance + Compass Tools. For this segment leverage our Investor Advantage Tool which is built on 1,500 transcribed talks from on stage at our 300 events to date , HyperIntelligent which is built on 100M data points combining 20 of our tools so you can cast votes and get diverse points of view on any topic you are deciding on, Dewey: Your Instant Due Diligence Advisor, and Dewey's cousin Vetti: Your Real Estate Deal Analyst.

What do you need to adjust within buckets 1, 2 and 3 to scale your wealth faster?

What changes do you need to make in how you manage and scale your balance sheet?

What platform are you ultimately building? What is your offensive game?

The wealthiest families I have met over 19 years running our investor club build out deal origination, proprietary deal structures, acquire strategic choke points, hold a singular powerful position, and control lines of distribution in their industry. The families who are most trusted, well respected, control the follow of what gets seen, who gets funded, or who gets an audience scale their balance sheets rapidly.

Develop your own personal capital strategy to compound wealth as you have thought about yourself for 100,000 hours and you are lucky if anyone who ever gives you feedback or advice on building your wealth has thought about you for 100,000 seconds or 100 minutes. Ignore everyone but those further down the path than you, identify those you want to model and emulate, and seek out insights, training, strategies and mental models from decamillionaires, centimillionaires + Billionaires.

It has been taught to me by countless centimillionaires + billionaires that you do not want to compete head-to-head with 100+ or 1,000 competitors. As billionaire founder of PayPal Peter Thiel says, "if you find yourself competing head-to-head with someone you have really screwed up, I prefer an monopoly but will settle for an oligopoly." What I have learned is that if you can't have a monopoly, at least have a monopoly on the best positioning or best brand name.

The goal over time at a minimum is to create an uncopyable stack of IP made up of distribution, strategic choke points, flow of opportunities, technology, and processes that others cannot even fully understand or duplicate. That is how you reach massive strategic value.

What would be strategic in building out your IP in one of these ways that would move the needle on your next stage of growth?

Billionaire Brad Jacobs says there is no speed limit in business, and going slow is for chumps. What is your crystal clear vision so powerful that it deserves ruthless execution?

Additional Notes

Implementation Instructions + Strategies

Become the best version of yourself and focus only on exciting exponential opportunities

You are rare. The value of focusing your energy, time, intelligence on the unique set of opportunities in front of you is worth millions of dollars. So act accordingly in becoming ultra-healthy to fuel your growth in wealth, invest in high quality whole foods, nothing processed or artificial, they aren't French fries they are cancer fries.

Create an accountability group with 1-4 friends, review our health optimization suggestions, join CrossFit or your local gym, walk 10-15k steps a day, and strive to be an example to everyone around you on being a good person, and good example of success. If you make a lot of money but your kids don't talk to you, you abuse substances, are wildly out of shape, and have no social life you are telling your team, family and kids that money is what you worship and nothing matters but money.

What is the #1 thing you are going to do to start becoming ultra-healthy?

It is not fun to waste time, have bad partners, a stressful employee, obnoxious clients, or business divisions that lose money. Delete all of that from your life, focus on having the most fun year of your life by investing 90% of your energy into what works, and if something can't be fixed after 1-2 attempts, move on. You can't care more than an employee about doing well on your team and growing. Remove stress. Define and post your family's or your values, and aggressively act on those. Maximize momentum.

What do you need to remove from your life?

Having the most fun year of your life doesn't mean non-stop vacation, it means consistent high performance, it means working harder than others as you are more excited and focused than others. Winners have momentum and so do losers, be high velocity, add value first, and occupy a niche overlooked by others. Few want to become founders, and few founders ever scale to $1M in revenue or $5-$10M+ net worth ... outfocus, outfun and outwork everyone in your niche.

Staying wealthy is not as easy as some may think, you have to avoid trusting all of your wealth with 1-2 groups who promise to have all the answers, you have to not take your foot off the gas too much as pure defense is typically a slow erosion of your wealth, you don't want to become overly distracted, overly concentrated, and while hard to build it is easy to lose wealth.

Most who make it to the top realize what so much more is possible than most think. I recently interviewed billionaire Grant Cardone on stage and he said he should 't have been able to buy a $300M asset from Blackstone worth $500M, just as my tiny company shouldn't have the most visited website in the family office industry (FamilyOffices.com). How is that even possible? Einstein was once credited with discovering relativity, but he didn't discover it, many studied it before ehe was born. He simply focused on nothing but relativity for over a decade.

What are you going to focus on for 3-5 or 10+ years until you own the space?

When I interviewed billionaire Tony Robbins for Billionaires.com he said a top 5 reason he became a billionaire was the power of proximity, being around wealth. This is core to why we operate our investor club, Family Office Club as well as Doctors Investor Club, our Pro Athlete network, and Deep Due Diligence Investors Club.

The more you spend time with, listen to thoughts from, read books authored by, and connect with in-person decamillionaires, centimillionaires and billionaires the more you will think and in turn act like them. Who you spend time with matters more than what you do. If you hang out with the wrong people they will encourage you to become lazy, succumb to vices, and be average. This is why I only read books authored by billionaires and listen to this David Goggins video daily. Navy SEALs, centimillionaires, decamillionaires, pro athletes, billionaires, they all focus on one thing ... mindset and mental state, they bring it up constantly. You already are uncommon among the uncommon, so demand excellence.

Growing your wealth is not a popularity contest, only 1 in 5,000 founders make it because it far from easy.

Please review FamilyOffices.com for our upcoming calendar of events, which can you make this year?

Two of my favorite quotes I learned through Eben Pagan is that "clarity multiplies action" and another is "the world has never moved this slow before and it will never move this slow again." You need to know who you are, where you are going, setup a game you can win, and put extreme focus and work effort into getting smarter constantly on getting there.

This requires being agile, building the right network, leveraging AI, securing distribution, learning how to negotiate, structure deals, sell, position, persuade, and execute a plan. It is complex, that is why less than 1% make it to our level, and why it is so rewarding if you do get there.

Thank you for supporting our investor club, the goal here is to provide you with the most powerful strategies we have learned when it comes to building wealth and scaling your balance sheet. I hope at least one point in this trail guide is highly actionable and worthwhile to focus on right now to get you to the next stage of building your wealth.

Maximum ROI. You will get 3x more out of this guide if you go slow, watch the videos, use the AI tools, and complete this printed out as a workbook. This is not about rushing through the guide but thinking on each major point and acting on it to maximize the impact.

Your Assistant. Family Office Club members also get an AI assistant built on this guide called Decamillionaire Sherpa. You do not need it to use this guide, everything here works on its own.

You do not become a decamillionaire by accident. You do not stay one by default. Complete the audit honestly in the following section to see what score you get out of 100 (2 points per checkbox)

Decamillionaire Scorecard

Instruction. Put a checkmark next to each item that is fully true today. Do not overestimate. The gaps are where compounding leverage lives.

Score yourself 2 points per checkmark for a total possible score of 100 points.

If you have any questions on implementing these strategies, want to send me your completed worksheet, or have questions on how to get more involved at the Family Office Club, please email me directly at Richard@FamilyOffices.com or text me at (305) 333-1155