Real Estate, Leadership & Growth – Serial Entrepreneur
Speaking with Adam Stein, Real Estate Broker & Performance Coach about scaling, leading, and winning at a high level.
ROOM LINK: https://www.clubhouse.com/i/real-estate-leadership-growth-serial-entrepreneur/slDKLRrV
Entrepreneurship is rarely a smooth ride. One day can bring momentum, validation, and growth; the next can bring rejection, financial pressure, or a problem that threatens to derail everything. In this conversation, Colin C. Campbell and Michael Gilmore explore the emotional reality of building a business through the lens of “the entrepreneur’s roller coaster.”
The discussion covers how founders can better manage the shocks that come with running a company, from broken deals and changing market conditions to team pressure, family stress, and personal burnout. Michael shares practical ways he protects his mental clarity, including setting firm weekend boundaries, taking periodic solo planning retreats, and finding trusted people outside the family to serve as a pressure-release valve.
Every major technology wave looks obvious in hindsight. The internet. Broadband. Cloud computing. Smartphones. The sharing economy. Artificial intelligence.
But in the beginning, none of them looked inevitable. They looked strange, experimental, expensive, impractical, or overhyped. The entrepreneurs who benefited most were not always the inventors of the technology. More often, they were the people who recognized the shift early, understood how it would change behavior, and built a focused business around the opportunity.
Catching the next tech wave is not guesswork. It requires pattern recognition, discipline, and a willingness to live close enough to the future to notice what others are missing.
One of the clearest ways to spot a technology wave is to use emerging tools before they become mainstream.
That does not mean buying every gadget or chasing every trend. It means deliberately surrounding yourself with the technologies that may change how people work, communicate, buy, travel, learn, or create.
Entrepreneurs who used fast internet early could see streaming, video conferencing, and online services becoming normal before the broader market did. People who experimented with Airbnb early could imagine a world where unused homes became income-producing assets. Those using AI tools every day are more likely to see practical business opportunities than people still treating AI as a novelty.
The point is simple: you cannot understand a wave from the shore. You have to get in the water.
When a new technology begins to matter, it creates noise. People talk about it in niche communities, social platforms, forums, founder groups, investor circles, and industry conversations.
That noise can be an early signal. Reddit, Clubhouse, domain marketplaces, developer communities, search trends, and keyword activity can all reveal where attention is moving before the mainstream catches on.
But noise alone is not enough. Many technologies generate attention and still fail to cross into mass adoption. NFTs, the metaverse, and certain robotics categories have all attracted massive interest while struggling to prove lasting mainstream utility.
The question is not, “Are people talking about it?” The better question is, “Are people changing their behavior because of it?”
A technology wave becomes powerful when it either solves a painful problem or creates a large new opportunity.
The internet solved distribution. Broadband unlocked video, remote work, streaming, and real-time digital experiences. Airbnb unlocked underused housing supply. Starlink is opening new possibilities for remote work, maritime living, and internet access in places that were previously disconnected.
AI is doing something similar across knowledge work. It can reduce the cost of legal drafts, software development, marketing analysis, content creation, research, and business planning. That does not mean human judgment disappears. It means the economics of many services are changing.
The strongest opportunities often appear where a new technology changes the cost structure of an old problem.
A useful test for any emerging technology is whether it changes your own habits.
Do you find yourself using it repeatedly? Does it save time? Does it make something possible that previously felt too expensive, too technical, or too slow? Does it change how you think about a market?
If a tool changes your behavior, it may change the behavior of others. That does not guarantee a startup opportunity, but it is a stronger signal than hype alone.
This is especially important for founders. If you personally do not understand why a technology matters, it is risky to build around it just because investors, media, or competitors are excited. The best opportunities often begin with a clear personal insight: “I get this. I can see where it is going.”
The biggest businesses are not always built directly on the first wave. Many are built on the aftereffects.
Amazon began with books, then expanded into nearly everything. Facebook emerged years after the internet itself became mainstream. Airbnb was not just a website; it was a second-order opportunity created by internet trust, online payments, mobile access, and changing travel habits.
The same pattern is happening with AI. The first wave was large language models. The aftershocks include AI agents, video generation, music generation, AI-assisted legal work, AI-powered software development, internal workflow automation, and niche tools for specific industries.
Founders should look beyond the headline technology and ask what new markets become possible because of it.
A technology can be useful and overhyped at the same time.
That distinction matters. The dot-com crash did not mean the internet was fake. It meant many companies had weak models, bad timing, or unsustainable valuations. The same can happen with AI, robotics, crypto, spatial computing, or any other emerging sector.
Entrepreneurs need optimism, but not blind optimism. The right approach is to test whether a technology solves a real problem, whether customers will pay, and whether the timing is right.
Some companies survive the chasm by narrowing their focus. Instead of trying to serve everyone, they become excellent in one niche. That “laser beam” approach creates survival, credibility, and expertise. Once the market matures, expansion becomes easier.
The next tech wave rarely announces itself clearly. It starts as experiments, conversations, niche adoption, and small behavior changes. Then, almost suddenly, it becomes obvious.
Entrepreneurs do not need to invent the next foundational technology to benefit from it. They need to recognize the shift, find the practical use case, focus on a specific market, and move before everyone else understands the opportunity.
The formula is not perfect, but it is repeatable: live near the future, listen for signal, test for real behavior change, solve a meaningful problem, watch for second-order effects, and stay disciplined enough to avoid hype.
The next wave is already out there. The advantage goes to the people paying attention before it becomes common knowledge.
Entrepreneurship is often described in heroic language: freedom, vision, independence, impact. All of that can be true. But anyone who has built a company knows the other side of the story. The same business that gives you energy in the morning can leave you exhausted by the afternoon. A single phone call can change the mood of an entire week. A strong sales month can make you feel unstoppable. A failed deal can make you question every decision that led you there.
That is the entrepreneur’s roller coaster. It is not a metaphor reserved for dramatic startups or venture-backed founders. It is the daily emotional rhythm of owning responsibility when there is no safety net beneath you.
The goal is not to eliminate the ride. That is impossible. The goal is to learn how to stay steady while the ride continues.
Every founder eventually gets hit with bad news. A lender pulls back. A broker passes. A customer leaves. A supplier raises prices. A deal changes shape. A new regulation, tax change, tariff, or market shift appears at exactly the wrong time.
In the moment, these events can feel catastrophic. The mind tends to take a single setback and turn it into a full collapse. But most business problems are not final verdicts. They are problems to be worked.
That distinction matters.
When founders freeze, avoid the issue, or spiral emotionally, the problem usually gets worse. When they move into action, even imperfect action, they regain some control. Calling a strategic planning session, bringing in trusted advisors, reviewing costs, reworking a sales strategy, or simply writing down the next three decisions can create momentum. Progress does not always solve the problem immediately, but it changes the founder’s relationship to the problem.
Doing something is almost always better than sitting inside the panic.
One of the hardest parts of entrepreneurship is that founders often carry stress they cannot fully share with their teams, families, or partners. They are expected to be the calming force while privately absorbing the uncertainty.
That pressure has to go somewhere.
Every entrepreneur needs someone they can speak to honestly. Not someone to dump on endlessly, and not necessarily a spouse or family member, but someone who understands the weight of business ownership and can hear the truth without becoming destabilized by it.
Family members can be supportive, but they are often emotionally tied to the outcome without having any control over it. Sharing only the bad news at home can unintentionally make them passengers on a roller coaster they did not choose and cannot steer. A spouse, partner, or child may hear the problems but never hear the resolutions, victories, or context. Over time, that can strain relationships.
A trusted peer group, mentor, advisor, or fellow entrepreneur can help absorb the emotional load in a healthier way. Founders need spaces where they can be blunt, uncertain, frustrated, and honest without turning their households into boardrooms.
The nonstop nature of entrepreneurship makes boundaries feel unrealistic. There is always another email, problem, deal, invoice, decision, or fire to put out. But founders who never step away eventually lose the clarity required to lead.
A firm weekend boundary can be one of the simplest stabilizers. Not every founder can fully avoid weekend work, especially during a crisis, but creating a default rhythm of disconnection gives the mind and body a chance to reset. It also signals to family and team members that the business does not own every hour of life.
Some founders also benefit from periodic solo planning retreats. Taking a day or two away from the normal environment can create enough distance to think clearly. The first step may simply be unloading every stress, concern, and fear into a private document. Once the noise is out of the founder’s head, it becomes easier to shift from anxiety to strategy.
That is where better questions emerge: What is actually happening? What are the strengths, weaknesses, opportunities, and threats? What decisions need to be made? What action items matter most when returning to the business?
Clarity rarely appears in the middle of constant interruption. Sometimes it has to be created deliberately.
The lows of entrepreneurship are obvious. The highs are more deceptive.
Success can create arrogance. Revenue growth, investor attention, strong press, or a rising valuation can convince founders they are smarter than they are. They begin to overspend, overhire, ignore warning signs, or assume the current momentum will last forever.
That is where the top of the roller coaster becomes dangerous.
A strong period in business should create discipline, not ego. When things are going well, founders should be asking how to protect the company, reward the team, build cash reserves, and prepare for the next downturn. Growth matters, but growth without restraint can become gambling.
There is a difference between leaning into momentum and spending every dollar as if the future is guaranteed. A business with cash reserves has options. It can hire when others are cutting, launch when competitors are stalled, or survive when the market turns. A business that spends everything during the good times has no cushion when the ride drops.
Teams often take their emotional cues from the founder. If the founder panics, the team panics. If the founder becomes arrogant, the team absorbs that too. If the founder stays calm, focused, and direct, the company has a better chance of working through the issue.
“Let’s work the problem” is one of the most useful mindsets a founder can bring into a crisis. It does not deny the seriousness of the situation. It simply refuses to let emotion become the operating system.
The entrepreneur’s roller coaster is unavoidable. There will be highs. There will be lows. There will be days that feel exhilarating and days that feel punishing. The founders who last are not the ones who avoid those extremes. They are the ones who learn how to respond with discipline, humility, and perspective.
In the end, entrepreneurship is not only a test of business skill. It is a test of character. It reveals how a person handles pressure, success, uncertainty, relationships, and responsibility. The ride may never flatten completely, but with the right habits and support systems, founders can stay steady enough to keep building.
In this episode of Serial Entrepreneur Secrets Revealed, the Startup Club community dives into practical AI growth hacks entrepreneurs are using right now to start, scale, and streamline their businesses.
The conversation covers real-world examples across legal documents, marketing analytics, inventory management, inbox prioritization, co-living operations, bookkeeping, content creation, workshops, and AI agents. One founder shares how AI helped draft a private placement memorandum in hours instead of requiring thousands of dollars in upfront legal costs. Another explains how ChatGPT was used to photograph furnished rental units, estimate replacement values, and generate an inventory spreadsheet. Others discuss using AI for inbox triage, customer lifetime value analysis, Facebook “Buy Nothing” sourcing, agent workflows, and NotebookLM-powered research.
Entrepreneurs are often hit hardest by forces they never saw coming: rising interest rates, tariffs, government policy changes, supplier disruptions, market collapses, and even personal crises outside the business. In this episode, the conversation centers on a simple but difficult truth: founders cannot control the external environment, but they are responsible for how they respond.
AI is no longer a future-facing technology reserved for large companies, technical teams, or venture-backed startups. It has become a practical operating tool for entrepreneurs who need to move faster, cut costs, test ideas, and make better decisions with fewer resources.
But the real advantage does not come from simply “using AI.” The advantage comes from knowing where to apply it, how to question it, and when to slow down enough to verify the output.
For entrepreneurs, AI is becoming less of a novelty and more of a business partner. It can draft documents, analyze data, create workflows, organize information, generate ideas, and help founders move through roadblocks that once required expensive outside help. The key is to treat it as leverage, not magic.
One of the clearest uses of AI is preparing the first version of complex business documents.
Entrepreneurs often pay thousands of dollars for legal, financial, or strategic documents before they even know whether an idea has traction. AI can now help draft early versions of private placement memorandums, business plans, investor summaries, operating procedures, internal policies, and vendor briefs.
That does not mean lawyers, accountants, or consultants disappear from the process. It means their role changes. Instead of paying someone to create everything from scratch, founders can bring a strong first draft and ask the professional to review, correct, structure, and finalize it.
This shifts the cost structure. Service providers who use AI well will become more valuable because they can deliver better work faster. Service providers who ignore it may become harder for small businesses to justify.
AI is especially useful when a business has information scattered across photos, emails, PDFs, spreadsheets, receipts, or notes.
A furnished rental operator, for example, can photograph furniture and appliances, ask AI to identify the items, estimate replacement values based on a target retailer or quality level, and organize everything into a spreadsheet. What used to require manual inventory work can become a repeatable workflow.
The same principle applies to receipts, asset lists, maintenance logs, customer support records, marketing reports, and internal documentation. AI can help convert unstructured information into usable business data.
The important step is review. AI can estimate, categorize, and organize, but the entrepreneur still needs to verify the output before using it for insurance, accounting, purchasing, or financial planning.
Many founders track metrics like return on ad spend, clicks, impressions, and conversion rates. Those numbers matter, but they can be misleading if viewed in isolation.
AI can help build deeper marketing analysis systems that connect ad performance to contribution margin, customer lifetime value, repeat purchase behavior, pricing, fulfillment costs, and cash flow timing.
A campaign may look profitable based on revenue alone, but if the margin is weak or the second purchase happens two years later, the business may still be losing money in the short term. AI can help founders create more thoughtful dashboards and decision frameworks around when to scale, pause, or cut spend.
This is where AI becomes more than a reporting tool. It becomes a thinking partner that helps ask better business questions.
AI agents are becoming a major area of experimentation. They can help automate email follow-ups, bookkeeping workflows, customer support, research, reporting, and project management.
Tools like n8n, LangGraph, Pinecone, pgvector, Claude Projects, ChatGPT Projects, NotebookLM, and other agent frameworks are making it easier to connect AI with business data and recurring tasks.
But automation introduces risk. Agents can misread documents, misunderstand instructions, create incorrect classifications, or build on earlier mistakes. In finance, legal, customer-facing support, and analytics, those errors can compound quickly.
The best approach is not full blind automation. It is supervised automation. Let AI perform the repetitive work, but build in human review, confidence thresholds, source checks, audit trails, and escalation rules.
AI should not be treated as the boss. The founder, operator, or subject-matter expert still owns the decision.
AI can also help founders explore business models they might not have considered.
A co-living operator looking to reduce furnishing costs may discover local “Buy Nothing” groups, secondhand sourcing strategies, or leasing arbitrage models through AI-assisted brainstorming. A founder building a new product can use AI to simulate landing pages, mockups, scripts, decks, and customer journeys before investing heavily in development.
This is one of AI’s strongest uses: helping entrepreneurs test before they build.
But there is a trap. AI makes it easy to create endless plans, decks, mockups, workflows, and content. That can feel productive while avoiding the harder work of getting customers, generating revenue, and validating demand.
The goal is not to become busy. The goal is to move the business forward.
Tools like NotebookLM show how powerful AI becomes when it is grounded in specific source material. Instead of asking a general AI model for broad answers, founders can upload documentation, books, transcripts, policies, help files, or internal notes and query that trusted information directly.
This is useful for training, research, customer support, onboarding, content creation, and internal operations. It also reduces the risk of irrelevant or unsupported answers because the AI is working from a defined knowledge base.
For best results, source quality matters. Clean documents, markdown files, text files, structured notes, and well-organized references usually produce better outputs than messy PDFs or incomplete uploads.
The entrepreneurs who benefit most from AI will not be the ones who ask it to do everything. They will be the ones who learn how to direct it.
That means writing better prompts, giving clearer context, checking sources, questioning assumptions, and knowing enough about the task to spot weak answers. It also means building systems where AI supports human intelligence instead of replacing it.
AI can save time. It can lower costs. It can unlock ideas. It can make small teams look much larger. But it still needs direction, judgment, and accountability.
The best founders will use AI as a multiplier for what they already know—and as a guide for learning what they do not.
Every entrepreneur eventually faces a moment when the problem is not bad execution, weak demand, or a poor product. Sometimes the problem comes from outside the building.
Interest rates rise. Tariffs change. A major supplier rewrites the terms. A government policy shifts. A platform that once drove revenue disappears overnight. A war, recession, banking issue, or tax change suddenly alters the math of the business.
These events can feel unfair because they often are. But fairness is not a business strategy. When external forces hit, the entrepreneur’s job is not to complain about the weather. It is to decide what to do before the storm gets worse.
The first step is brutally simple: name what is outside your control.
You cannot control interest rates. You cannot control tariffs. You cannot control whether a major advertising network exits your industry. You cannot control a government budget, a banking rule, or the timing of a market downturn.
But you can control how quickly you respond.
That response may include reducing expenses, changing suppliers, renegotiating payment terms, narrowing the product line, shifting pricing, preserving cash, or rebuilding the company around a leaner operating model. The danger is not only the external shock itself. The danger is pretending the shock will pass before it damages the company beyond repair.
Hope is useful for morale. It is not a plan.
In good times, inefficiency hides. Extra staff, slow processes, underused tools, bloated inventories, and weak margins can all survive when revenue is strong and capital is cheap.
In difficult times, those weaknesses become visible quickly.
A business under pressure has to become clear-eyed about what is essential. That does not mean cutting randomly. It means understanding which people, products, systems, and expenses are truly keeping the company alive.
Sometimes that means delaying purchases. Sometimes it means selling assets. Sometimes it means using technology to replace repetitive work. Sometimes it means making painful staffing decisions.
Layoffs should never be treated casually. Employees are not numbers on a spreadsheet. They have families, obligations, and lives built around their income. But if the core business fails, everyone loses. The responsibility of leadership is to make those decisions carefully, humanely, and early enough that the company still has a path forward.
Many entrepreneurs delay hard decisions because they are emotionally attached to the business. They have invested years, money, identity, and reputation into it. Closing a product line, shrinking a team, or shutting down a venture can feel like personal failure.
But it is not always failure. Sometimes it is a business decision that protects the next opportunity.
One useful approach is to set clear stage gates. Decide in advance what must be true for the business to continue on its current path. That may be a revenue target, margin level, cash reserve, debt reduction milestone, or customer acquisition goal. If the business misses the gate, the decision is not emotional anymore. It becomes operational: pivot, cut, sell, or close.
The worst option is often refusing to choose. Not making a decision is still a decision. It simply hands control to the market, the bank, the creditor, or the next crisis.
When pressure rises, many founders turn inward. They obsess over their own numbers, their own payroll, their own debt, and their own survival.
That is understandable, but incomplete.
Customers, suppliers, lenders, partners, and employees may be facing pressure too. The founder who picks up the phone, visits clients, explains the situation honestly, and asks how both sides can get through the difficulty often finds options that were not visible from behind a desk.
Strong relationships can create flexibility. A supplier may extend terms. A customer may commit earlier. A landlord may adjust rent. A partner may help bridge a gap. These things rarely happen when the relationship has only been transactional.
Business is not just about extracting value from relationships. It is about building enough trust that people want to help when conditions are difficult.
Survival also requires discipline with customers.
The customer is not always right. Sometimes a customer request creates complexity that spreads through the entire organization. A custom solution may look like revenue on the surface but quietly drain time, margin, and focus from the team.
In a fragile environment, saying yes to the wrong work can be dangerous. Saying no can protect the business.
A strong company knows what it does well, what it should not do, and which opportunities are not worth the operational cost. Focus is not just a growth principle. In hard times, it becomes a defense mechanism.
Entrepreneurship is often described as optimism, persistence, and risk-taking. Those traits matter, but they are not enough.
The deeper job is judgment.
Judgment means knowing when to push and when to stop. When to cut and when to invest. When to help someone and when to protect the company. When to serve a customer and when to walk away. When to accept reality and when to fight to change it.
External forces will always exist. The market will shift. Governments will act. Platforms will change. Capital will get expensive. Customers will hesitate. Suppliers will disappoint.
The entrepreneur cannot control all of that.
But the entrepreneur can decide faster, communicate better, build stronger relationships, protect cash, reduce waste, and face reality before reality becomes a crisis.
That is where real leverage lives.
A few years ago, I was sitting across from a CEO who had just wrapped up his annual planning session. His team had worked hard; they had goals everywhere, color-coded spreadsheets, sticky notes on whiteboards, a long list of initiatives. He leaned back and said, “Patrick, I feel like we’re doing everything. And yet, I feel like we’re going nowhere.”
I’ve heard some version of that sentence more times than I can count.
Having a lot of goals is not the same as having the right goals. Busyness is not progressing, and when you try to move everything at once, you often end up moving nothing at all.
That’s where Winning Moves come in.
A Winning Move is not an incremental improvement. It’s not a tweak to a process or a modest bump in efficiency. A Winning Move is a strategic bet, a 3-to-5-year initiative with the genuine potential to double your revenue.
I wrote about this in depth in Chapter 2 of my book Rhythm: How to Achieve Breakthrough Execution and Accelerate Growth. The idea is simple: rather than spreading your energy across dozens of priorities, you identify 2-3 big moves that could fundamentally change the trajectory of your business. These are the ideas that make your team’s eyes light up: a new market, a new product line, a new model that unlocks growth you can’t achieve by just running your existing business harder.
The key is to be selective. Most companies I work with start out thinking they have 6, 7, maybe 8 potential Winning Moves. But you can’t execute them all well. The discipline is to evaluate each idea honestly: What’s the revenue impact? Does our team have the capability to actually execute this? Two or three strong Winning Moves, properly resourced and relentlessly executed, will outperform a list of ten every single time.
Here’s where goal-setting gets interesting. Most people approach goals from the bottom up; they look at what they did last year and add a percentage. That’s operational thinking, not strategic thinking.
Winning Moves require you to flip the lens. You start with the future you want to create, your BHAG, your 3-to-5-year targets, and then work backward. What would have to be true to get there? What moves would have to succeed? That’s how you set goals that are genuinely connected to strategy, not just numbers pulled from last year’s actuals.
This is the heart of the Think Plan Do® framework: Think about where you want to go, Plan the moves that will get you there, and Do the work with accountability and rhythm.
One of the most powerful things you can do during your Annual Planning session is to carve out dedicated time, at least a full day, for strategic thinking. Not just reviewing last year’s numbers or allocating budget, but genuinely asking: What are the 2-3 moves that could change everything?
One mistake I see often is treating a Winning Move like a finished strategy from day one. It’s not; it’s a hypothesis.
When you first identify a potential Winning Move, you’re really saying, “We believe this could double our revenue if these assumptions are true.” Your job in year one is to test those assumptions, to gather data, run small experiments, talk to customers, and find out if the premise holds up. This is why the Winning Moves process includes explicit assumption tracking. You’re not committing to a 3-year execution plan before you’ve pressure-tested the idea.
I’ve seen companies avoid enormous mistakes, years wasted, capital burned because they built this test-and-learn discipline into their strategic process. And I’ve seen others charge ahead without it, only to discover 18 months in that a core assumption was wrong.
Be curious, be rigorous before you go all-in, and make sure the foundation is solid.
Identifying your Winning Moves is the strategy. Executing them is everything else.
This is where a lot of companies break down. They have a beautiful annual plan, great Winning Moves, clear targets, and then they return to the office on Monday and get back to the urgent. Six months later, nothing has actually moved.
The bridge between your annual strategy and your daily work is the quarterly plan. Every 90 days, your team should ask: What are the 3-5 priorities this quarter that will actually advance our Winning Moves? Who owns each one? How will we know if we’re on track?
Execution Is the Ultimate Competitive Advantage
Over the past two decades, I’ve worked with hundreds of leadership teams, and I’ve noticed a pattern. The companies that grow the fastest aren’t necessarily the ones with the smartest strategies. They’re the ones with the clearest priorities and the discipline to execute them.
Winning Moves force leaders to make choices, they create focus, and align resources to help leadership teams stop chasing dozens of good ideas so they can fully commit to the few initiatives that will create meaningful impact.
If your strategic plan feels more like a wish list than a roadmap, take a step back and ask a simple question:
What are the three to five moves that would most dramatically change the trajectory of our business over the next three to five years?
That’s where strategy becomes actionable.
To help you identify your own Winning Moves, explore our 3-5 Year Strategic Planning resources and learn how high-growth leadership teams create clarity, alignment, and focus around what matters most.
Start here: Winning Moves Strategic Planning Resources
Because growth doesn’t come from doing more things. It comes from making the right moves and executing them well.
—Patrick Thean
Two years ago, I wrote an article for Startup Club called “10 Secrets to Writing a Best-Selling Non-Fiction Business Book.”
That article hit #1 on Google for the search term “How to write a best selling business book,” and it has stayed there ever since.
So I thought it was time for Part II.
The first article was written after the launch of Start. Scale. Exit. Repeat., my first book. Since then, the book has become a #1 Amazon best seller in 15 categories, won more than 40 global awards and recognitions, and at the time of writing this article we #1 on Amazon in the categories “Starting a Business” and “Entrepreneurship Management” two and a half years after launch.
Not bad for someone whose English teacher would probably still be shocked.
I am now working on my second book, How to Catch the Next Tech Wave: Patterns Behind Every Disruption, From the Internet to AI. As I go through the process again, I am realizing how much more I have learned, especially in a world where artificial intelligence has changed how people write, publish, market, and consume content.
Before I get into the new lessons, here is a quick summary of the first article.
The first article started with the most important question: why are you writing the book?
A great business book is not really about the author. It is about the reader. The reader wants to know how the book will help them, change them, guide them, or give them a framework they can use.
I also talked about the importance of choosing the right publisher, creating a powerful first impression with the cover, designing the inside of the book to match the promise on the outside, and writing in a way that busy people can actually consume.
Short sentences.
Short paragraphs.
Short chapters. In fact, Start. Scale. Exit. Repeat. has 78 chapters.
No walls of text. No lectures disguised as wisdom.
The article also covered the importance of authenticity, a strong launch, ongoing promotion, awards, reviews, and the long-term flywheel that begins after the book is published. Writing the book is not the finish line. It is the starting line. You might want to check this article out first before reading this one.
Two years later, here are 10 more lessons I wish I had known before writing, launching, and promoting a business book.
1. Make the Content Real
AI is tempting.
It can help you brainstorm, critique, organize, tighten, and improve your writing. Used properly, it can make a good idea stronger.
But AI should not replace the soul of the book.
The raw material still must come from you. Your experience. Your failures. Your scars. Your insights. Your content has to be “Raw and Real”. Your strange little stories that somehow make a business lesson unforgettable.
That is the difference between a book that sounds polished and a book that means something.
When I write, I start with my own thoughts first. I get the ideas down in my own voice. Then I may use AI to help critique it. That is a very different thing from asking AI to create the heart of the book. Note: in the case of my book, zero AI was used and thankfully I had great human editors at Forbes Books.
Readers can feel the difference.
A meaningful business book has to come from a real place. It has to reflect something you lived, learned, struggled with, or earned the hard way.
2. Your Name on the Cover Matters More Than You Think
In the first article, I talked about how important the title and cover are.
Since then, I learned something interesting at a publishing conference: do not make your name too small.
Many first-time authors are modest. They shrink their name on the cover because they do not want to look arrogant. I am Canadian and trust me we make an art of modesty. That is not a strategy when writing and launching a new book.
That may feel humble, but it can also send the wrong message.
A larger author name can create confidence. It tells the reader, “This person stands behind this work.” It gives the book a stronger presence. I was pretty modest with my name on the first book, but you can see from the cover draft above that I am not going to hide, but show it off with pride and confidence.
The title still matters. The design still matters. But do not hide from the cover. If you believe in the book, put your name on it like you mean it.
3. Design Your Book for the Real Buyer
At that same conference, I heard something else that caught my attention: women buy a significant majority of books.
NielsenIQ’s UK Books & Consumers data has reported that women bought 59% of all books, 58% of print books, and 65% of ebooks.
That matters.
Too many business books are designed as if the only reader is a man in a navy suit standing in front of a glass office building, holding a coffee and pretending he is not exhausted.
Business books do not have to feel cold, aggressive, or overly masculine.
With Start. Scale. Exit. Repeat., I got lucky. I didn’t plan it but my team included multiple women involved in the project before publication, including work on images, design, and production. The book was built to feel approachable, clear, visual, and useful. And they made certain the book appealed to women.
And it worked.
Based on Google data, almost 50% of our readers appear to be women. For a business book, I think that is meaningful.
Entrepreneurship is not a male category. Startups are not a male category. Business books should not be either.
4. Awards Help, But Not the Way You Think
Start. Scale. Exit. Repeat. has now won more than 40 global awards and recognitions. More awards than any other book on entrepreneurship ever.
That sounds impressive.
But here is the truth: awards do not magically open the floodgates.
You do not win an award and suddenly wake up to thousands of orders, a documentary crew on your lawn, and Oprah calling while you are brushing your teeth.
Awards help because they build trust.
They are social proof. They matter on your Amazon listing. They matter when someone is deciding whether your book is credible. They matter when you are pitching yourself for podcasts, speaking events, media, or partnerships.
Awards are not the engine. They are fuel for the engine.
If your book is genuinely strong, apply for awards. But do not expect the award alone to do the work. But let me be clear here….your book has to be great! It has to hit 4.7 or higher on Amazon. Investing in applying for awards will not win you awards…these are real judges with awards that have reputations and some of them are well recognized. They do not hand out awards because you simply pay an application fee. If you have a good book, promote it and apply for every award you can.
5. Reviews Are Still the Currency That Matters
If awards are social proof, reviews are the oxygen.
Getting people to review your book is ridiculously hard. People will read the book, love the book, tell you it changed their thinking, send you a beautiful LinkedIn message, and then somehow vanish into the wilderness the moment you ask for an Amazon review.
Ask anyway.
When you appear on podcasts, ask for reviews.
When you speak at events, ask for reviews.
When readers message you, thank them and ask for a review.
When other authors support you, support them back.
At one recent book awards event, I bought three books from other authors. I read them. Then I reviewed each one on Amazon. Other authors have done the same for me.
That is one of the unexpected things I have learned: independent authors can become a real community. Help them. Review them. Connect with them. Promote the good ones.
The book world works better when authors support each other.
And if you love this article, please buy the book and see what makes it so great. And I would be honored if you reviewed the book.
No, I mean review the book.
Seriously, I am not joking…..review the book.
Ok this is the last time I am asking: will you damn well review the book!
6. BookBub Can Move the Needle
I have been impressed with BookBub.
We have been listed on their site three times over the last three years, and each time, the book popped up on the charts.
That does not mean BookBub is a magic machine. Nothing is. But it can be a powerful promotion tool, especially if your book already has strong reviews, a professional listing, and a clear audience. And they are extremely selective. A Forbes Books person working with me told me that only a handful of books in her career had gotten chosen to be listed on it and we got chosen 3 times. The book has to be great, has to have momentum and reviews…and maybe, just maybe they might list it.
The bigger lesson is this: keep testing channels.
Amazon ads. Podcasts. Newsletters. BookBub. Articles. Speaking events. Guest posts. LinkedIn. Awards. Media. Partnerships.
Not every channel will work. But some will.
And when something works, repeat it.
7. The Biggest Value May Not Come From Book Sales
Most authors do not make their real money from royalties.
That does not mean the book is not valuable.
For me, one of the biggest rewards is when someone sends me a LinkedIn message telling me the book made an impact in their life or business.
Beyond the personal impact, the book has created business opportunities I never expected.
One example came from another author who asked me to pre-read and critique his book. That relationship eventually led to an invitation to his home in Whistler. Today, one of my companies is working with his firm, and that relationship could lead to a major sale of one of my businesses creating millions of dollars in value. You never know where your book will lead you.
That did not happen because of royalties.
It happened because the book created trust.
A strong business book can become a door opener. It can create relationships, credibility, partnerships, speaking opportunities, consulting opportunities, investment opportunities, and even exits.
The book is not just a product.
It is a platform.
8. Podcasts and Articles Still Work
Podcasts are one of the best free marketing tools available to authors.
Most podcast hosts are looking for guests with a clear point of view, a strong story, and something useful for their audience. A good business book gives you all three.
But do not stop at podcasts.
Write articles. Comment on current issues. Share lessons. Build your voice in public.
I joined Forbes Council, which has a small fee, and that has allowed me to comment on business issues and publish my own articles. I also write for Entrepreneur magazine.
And, of course, I write for Startup Club.
If you are an entrepreneur, author, investor, or founder with a useful lesson to share, Startup.club is looking for contributors and guest speakers. Write something real, practical, and specific. That is what performs. And it costs you nothing.
And Startup.club articles can perform very well in SEO, as my first article proved.
Just remember: write something real.
9. Use AI to Launch and Promote, Not to Fake Expertise
Many authors have mixed feelings about AI.
I understand that.
Writers spend years building a voice, a point of view, and a body of knowledge. It took me 10 years to write my book. Thanks to my extensive travel and a lot of late-night flights, we finally got it done.
Then AI arrives and suddenly everyone thinks they can “write a book” in a weekend.
They cannot.
They can generate a manuscript-shaped object. That is not the same thing.
But AI can be incredibly useful if you use it the right way.
You can use AI to help identify awards and application deadlines.
You can use it to compare promotion options.
You can use it to think through Amazon ads, Google ads, podcast outreach, book positioning, audience segments, and launch strategy.
I once had two award ceremonies on the same weekend, one in New York and one in Las Vegas. I used AI to help me think through the decision. It did not make the decision for me, but it helped organize the tradeoffs.
I also use ChatGPT voice in the background when I am doing new things. It is like having a research assistant nearby.
I also created a custom GPT for Start. Scale. Exit. Repeat. by uploading the book and allowing members to ask questions about it. If you go to Startup.club and click on AI…..it’s all about my book and that tool helps readers explore the ideas in the book, and it even helps me quickly find references when I am preparing for a podcast, article, or speech.
That is a smart use of AI.
The goal is not to replace your thinking.
The goal is to extend it.
10. Make the Book Easy for the Reader
The first article started with a simple idea: it is all about the reader, not the author.
I believe that even more now.
Everything in the book should serve the reader and a good book actually changes something in their life. They might get one good idea and run with it that makes them money or changes them for the better.
The structure. The chapter length. The stories. The illustrations. The callouts. The examples. The design. All should be done with the reader in mind.
In Start. Scale. Exit. Repeat., we used very short paragraphs and short chapters. The book has 78 chapters. We included personal stories and interviewed dozens of entrepreneurs about their own experiences. We used more than 60 hand-drawn images and over 100 callouts.
Why?
Because the goal was to make the book easy to consume.
A year after one of my speeches, someone came up to me and said they remembered a story I told about the first night after selling my first company.
They remembered the story.
That is how people learn.
They do not remember lectures. They remember moments. They remember stories. They remember how the lesson made them feel.
Then, if you do your job well, they remember the principle behind the story.
A great business book is not just information.
It is information made memorable.
Final Thought: The Book Is Only the Beginning
Writing a book is personal.
The best authors put something real on the page. They are vulnerable. They share what worked, what failed, and what hurt. They tell the truth in a way that helps someone else move forward.
That is what makes a business book matter.
Not the ranking.
Not the awards.
Not the launch party.
Not even the sales.
Those things matter, but they are not the point.
The point is impact.
If your book helps one entrepreneur avoid a painful mistake, make a better decision, raise capital, build a stronger company, or keep going when they are ready to quit, then the book has value.
If it also builds your credibility, creates opportunities, opens doors, and helps your business, even better.
That is the power of a great business book.
It can help the reader.
It can help the author.
And sometimes, if the book is good enough, it can keep working for years after you write it.
