How to Kill Your Business: A Guide to Self-Sabotage (and How to Avoid It)
How To Kill Your Business helps you ask ‘Is my business a raging dumpster fire waiting to happen?’
It is vastly better to learn from other people’s experiences than to suffer the extremely costly lessons on your own! Please learn from me and all the rest that I have watched or concerned me during my tenure.
Let’s face it: building a business is hard. But sometimes, we’re our own worst enemies.
This autobiographical book of lessons from Doug Franklin, “How to Kill Your Business,” isn’t your typical rah-rah success story. It’s a raw, honest post-mortem, born from the ashes of a business lost in April 2023. Drawing on the powerful “Inversion Thinking” process championed by Charlie Munger, we’ll explore the 73 (and counting) ways you might be unknowingly sabotaging your own success.
Instead of focusing on what to do, we’ll flip the script. By examining the absolute worst things you could do to tank your business, you’ll gain a powerful, intuitive understanding of what not to do. Think of it as a guided tour through the minefield of entrepreneurship, with a clear map to avoid disaster.
Get Yours:
The planned release date is APRIL 2026!
We are drafted, and the work is up for editing.
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Genera:
Biography Genera Books: “How To Kill Your Business” is a candid, experience-based memoir that uses inversion thinking to distill the author’s hard-won business lessons.
Educational: Because How To Kill Your Business is a book about lessons learned, we need to set this in the Educational category, regardless that it is neither fun nor relaxing :/
Summary:
“How to Kill Your Business” is a brutally honest guide for entrepreneurs who want to avoid the common pitfalls that lead to business failure. Based on real-world experience and the principles of Inversion Thinking, this book explores 73 distinct ways to sabotage your business, from neglecting your budget and cheaping out on marketing to ignoring customer feedback and fostering a toxic work environment. By understanding how to create the worst possible outcomes, you’ll gain a powerful understanding of how to build a thriving, resilient business.
Ready to inoculate your business against disaster?
Get Your Copy of “How to Kill Your Business” Today!
Preview: A Taste of Self-Sabotage
Here’s a glimpse into the hard-won lessons you’ll find within “How to Kill Your Business”:
1. The Budget Blunder: “We Don’t Need No Stinking Budget!”
Ignoring your budget is like driving a car with your eyes closed. Sure, you might get lucky for a while, but eventually, you’re going to crash. Here’s what happens when you ditch the budget:
Cash Flow Catastrophe: Spending more than you bring in is a one-way ticket to cash flow hell. Overdue bills, damaged credit, and a constant scramble to stay afloat become your new normal.
Profitless Pursuit: Reduced profits mean less investment in growth, innovation, and even basic survival.
Financial Instability: A business built on overspending is a house of cards waiting to collapse.
The Solution?: Create a realistic budget, track your spending meticulously, and adjust as needed. Don’t be afraid to be conservative in your estimates. Financial discipline is the bedrock of long-term success.
2. Ad-pocalypse Now: Cheaping Out on Ads
Thinking you can get away with bargain-basement advertising? Think again. Skimping on ads is like trying to win a race with a flat tire.
Ineffective Ads: Poorly designed, poorly targeted ads are a waste of money. They simply won’t reach your target audience or generate results.
Wasted Money: Spending less but generating zero return is just throwing money in the trash.
Damaged Reputation: Shoddy ads can create a negative impression of your business, turning off potential customers before they even learn about you.
The Solution?: Invest in quality creative, target your ads effectively, and measure your results relentlessly. Be patient and persistent, effective advertising takes time and effort. Remember, a well-placed, high-quality ad is far more valuable than a scattershot of cheap, ineffective ones.
3. The Vanity Trap: Chasing Empty Numbers
In the age of social media, it’s easy to get obsessed with vanity metrics like impressions, likes, follows, and views. But these numbers often tell you nothing about the real health of your business.
Bad Decision-Making: Focusing on vanity metrics can lead you to make decisions based on what looks good on paper, rather than what’s actually good for your bottom line.
Distraction from What Matters: Obsessing over likes can distract you from the core elements of your business
Reputational Damage: Boasting about vanity metrics while failing to deliver on your promises can damage your reputation and erode customer trust.
The Solution?: Focus on metrics that directly impact your business goals, such as customer acquisition cost, conversion rates, and customer lifetime value. Don’t get caught up in the numbers game; keep your eye on the prize.
4. The Echo Chamber: Ignoring Market Demand
Building a product or service in a vacuum is a recipe for disaster. If you ignore what the market is asking for, you’re likely to end up with something no one wants.
Low Sales: If you don’t have any customers, you’re not going to sell anything.
Negative Reviews: Customers who are unhappy with your product or service are likely to leave negative reviews online. This can damage your reputation and make it harder to attract new customers.
Increased Costs: If you have to spend money on marketing and advertising to try to sell your product or service, you’re going to end up losing money.
Loss of customers: If your customers are unhappy with your product or service, they’re likely to take their business elsewhere. This can lead to a loss of revenue and market share.
The Solution?: Before you launch anything, do your research. Talk to potential customers, survey your audience, and analyze market data to understand what people truly need and want.
5. The Single Source of Doom: Neglecting Diversification
Relying on a single product or customer is like building your house on a foundation of sand. It only takes one setback to bring everything crashing down.
Increased risk: If you have only one product, and that product is not successful, your business could fail.
Missed Opportunities: If you don’t diversify your product mix, you could miss out on opportunities to reach new customers and grow your business.
Stagnation: If you don’t keep up with the latest trends and develop new products, your business could become stagnant.
The Solution?: Consider your target market and their needs. Look for trends in your industry and don’t be afraid to experiment with new things.
6. The No-Vision Vision: Lacking a Cohesive Plan
A cohesive vision is essential for any business. It provides a sense of direction and purpose, and it helps to keep everyone on the same page. Without a cohesive vision, businesses are more likely to flounder and fail.
Unmotivated Employees: Employees are more likely to be motivated when they understand the company’s vision and how their work contributes to achieving that vision.
Disloyal Customers: Customers are more likely to do business with companies that have a clear vision and a strong commitment to excellence.
Hesitant Investors: Investors are more likely to invest in companies that have a clear vision and a strong track record of success.
The Solution?: Start by defining your core values. Set ambitious goals and create a plan. Communicate your vision to everyone in your organization.
7. Cash Flow Catastrophe: Frittering Away Your Funds
“Cash is King” isn’t just a catchy saying; it’s a fundamental truth of business. Running out of cash is a death sentence for any company, no matter how innovative or well-intentioned.
Inability to Pay Bills: Without cash, you can’t pay your bills, you can’t invest in your business, and you can’t grow.
Need to Borrow Money: This can be expensive, and it can add to your debt load.
Need to Close Your Business: This is the worst-case scenario, but it’s a possibility if you don’t manage your cash flow carefully.
The Solution?: Track your income and expenses closely, create a budget and stick to it, pay your bills on time, have a rainy day fund, and invest in your business.
8. Bad Company: Letting Toxic People Thrive
Dan Pena said it best: “They are like a corpse stinking up the office.” Letting bad people fester in your organization is a surefire way to poison your work environment and destroy productivity.
Damaged Reputation: Customers and partners may be less likely to do business with you if they know that you have bad people working for you.
Decreased Productivity: Bad people can create a negative and stressful work environment.
Stealing: Bad people may be tempted to steal from your business. This can include stealing money, equipment, or even ideas.
Sabotage Your Success: Bad people may be jealous of your success and try to sabotage it.
The Solution?: Set clear expectations, create a positive work environment, have a zero-tolerance policy for bad behavior, take action quickly, and document everything.
9. The Burn Notice: Torch Your Network
Building a strong network of relationships is essential for long-term success. But burning bridges, alienating people, and destroying those connections can have devastating consequences.
Lose access to valuable resources: When you alienate someone, you’re losing access to their knowledge, skills, and experience.
Damage your reputation: When you’re known for being rude, disrespectful, or dishonest, people are less likely to want to do business with you.
Create a toxic work environment: When you’re constantly arguing with your employees and partners, you create a toxic work environment.
Miss out on opportunities: Allies can provide you with new ideas and perspectives that you may not have considered on your own.
The Solution?: Treat people with respect, follow through on your promises, and be honest and ethical.
Ready to learn more about how to avoid these deadly mistakes?
Get Your Copy of “How to Kill Your Business” Today!
More Ways to Murder Your Business (and How to Prevent It)
#05: Don’t Give A Fuck! (and why passion is essential)
#06: Forget Inventory Controls! (and how to keep track of your stuff)
#07: Skip Follow-Up, It’s A Time Sink! (and why persistence pays off)
#08: Skip Looking At Your Results. (and the power of data-driven decisions)
#11: Enjoy Having Too Many People, Ignore Your Budget! (and the importance of efficient staffing)
#15: Gamble! Don’t Calculate Then Mitigate Risk, Just Gamble! (and the difference between calculated risk and reckless behavior)
#17: Cash Is King, So Fritter It Away, Keep None! (and how to manage your finances like a pro)
#18: Take Advice From People Who Have Never Done It Before! (and why experience matters)
#19: Pay Others Before Paying Yourself! (and why self-preservation is not selfish)
#20: Worry About The Opinions Of Others! (and how to develop a backbone)
#21: Correct Mistakes In Public! (and the art of constructive criticism)
#22: Let Bad People Fester In Your Organization! (and why a toxic workplace is a death sentence)
#23: Burn Bridges: Piss People Off So They Won’t Help! (and why networking is essential)
Don’t let your business become a cautionary tale. Learn from my mistakes and build a thriving, sustainable venture.
Get Your Copy of “How to Kill Your Business” Today!
About the Author:
Doug Franklin ran Houston Daylighting for seven years before we hit a market downturn and ceased operations. You can read more of the summarized history HERE.
Contact:
Our contact page is HERE if you would like to reach out or ask some questions.
Articles:
If you would like to check out our slightly lighter take on this work, we posted an article on X.com HERE.
On the other hand,
The article on LinkedIn has a little more of a professional perspective and is shared in our new author group, too. That article on LinkedIn Pulse is HERE
Rapid Fire Lessons in Business Self-Destruction
This section is designed to give readers a quick, sharp dose of potential pitfalls. Each lesson is presented concisely, with a clear indication of the danger and a quick takeaway.
1. #04 Don’t Focus On How It Was Successfully Done!
Summary: Why bother learning from your past successes? Ignore what worked well and try to reinvent the wheel.
The Danger: Wasting time, money, and resources on unnecessary experimentation when proven methods already exist.
The Antidote: Document and analyze your past successes to create repeatable systems and processes.
2. #05: Don’t Give A Fuck!
Summary: Show no passion or enthusiasm for your business. Let apathy be your guide.
The Danger: Lack of motivation, poor decision-making, and a decline in employee and customer engagement.
The Antidote: Cultivate a genuine passion for your business and instill that passion in your team.
3. #06: Forget Inventory Controls!
Summary: Counting dusty boxes is boring! Ignore inventory management altogether.
The Danger: Stockouts, overstocking, inaccurate financial records, and increased risk of theft.
The Antidote: Implement a robust inventory management system to track stock levels, optimize ordering, and minimize waste.
4. #07: Skip Follow-Up, It’s A Time Sink!
Summary: Following up with leads, customers, or even employees is a waste of valuable time. Let them fend for themselves.
The Danger: Lost leads, missed opportunities, damaged relationships, and decreased customer satisfaction.
The Antidote: Make follow-up a priority, automate the process where possible, and build strong relationships through consistent communication.
5. #08: Skip Looking At Your Results.
Summary: Data is for nerds! Ignore key performance indicators (KPIs) and fly blind.
The Danger: Missed opportunities, costly mistakes, customer dissatisfaction, and ultimately, business failure.
The Antidote: Track relevant KPIs, analyze your results regularly, and make data-driven decisions to improve your business.
6. #09: Don’t Bother Diversifying Products, Always Keep a Single Product Revenue Source!
Summary: Stick to one product, no matter what! Diversification is for the weak.
The Danger: Increased risk, missed opportunities, stagnation, and vulnerability to market changes.
The Antidote: Diversify your product mix to reach a wider audience, reduce risk, and adapt to evolving market demands.
7. #10: Keep As Few Customers As Possible!
Summary: Customers are a pain! The fewer, the better.
The Danger: Financial instability, damaged reputation, lack of diversity, and increased vulnerability to customer attrition.
The Antidote: Focus on acquiring and retaining a diverse customer base to ensure long-term stability and growth.
8. #11: Enjoy Having Too Many People, Ignore Your Budget!
Summary: More is always better, especially when it comes to employees. Ignore the budget and hire away!
The Danger: Overspending, hiring the wrong people, a toxic work environment, and ultimately, financial ruin.
The Antidote: Adhere to a strict budget, hire strategically, and prioritize efficiency over headcount.
9. #12: Lack All Cohesive Vision!
Summary: Who needs a clear sense of direction? Let chaos reign!
The Danger: Decreased productivity, unmotivated employees, disloyal customers, and hesitant investors.
The Antidote: Define a clear vision for your business, communicate it effectively, and ensure that everyone is working towards the same goals.
10. #13: Craft A Vision Too Small To Support Your Goals!
Summary: Don’t dream too big! Keep your vision small and manageable.
The Danger: Limited growth potential, boredom, missed opportunities, and an inability to attract top talent.
The Antidote: Develop a vision that is ambitious enough to inspire and support your long-term goals and attract a talented team.
11. #14: Ignore What The Market Is Asking For!
Summary: You know best! Ignore customer feedback and build what you want.
The Danger: Low sales, negative reviews, increased costs, and loss of customers.
The Antidote: Conduct thorough market research, listen to customer feedback, and be willing to adapt your product or service to meet market demands.
12. #15: Gamble! Don’t Calculate Then Mitigate Risk, Just Gamble!
Summary: Business is a casino! Throw caution to the wind and gamble everything.
The Danger: Financial ruin, damaged reputation, and loss of everything you’ve worked for.
The Antidote: Carefully assess and mitigate risks, make calculated decisions, and avoid reckless behavior.
13. #16: Encourage Single Points Of Failure!
Summary: Rely on one supplier, one employee, or one system. What could go wrong?
The Danger: System failures, lost revenue, damaged reputation, and increased costs.
The Antidote: Diversify your resources, create backup plans, and train your employees to handle multiple tasks.
14. #17: Cash Is King, So Fritter It Away, Keep None!
Summary: Money is meant to be spent! Ignore cash flow management and live for today.
The Danger: Inability to pay bills, increased debt, layoffs, and ultimately, business closure.
The Antidote: Manage your cash flow carefully, create a budget, pay your bills on time, and save for a rainy day.
15. #18: Take Advice From People Who Have Never Done It Before!
Summary: Everyone’s an expert! Seek advice from those who lack experience and knowledge.
The Danger: Bad decisions, lost money, damaged reputation, and loss of motivation.
The Antidote: Surround yourself with experienced mentors, advisors, and industry professionals who can offer valuable guidance.
16. #19: Pay Others Before Paying Yourself!
Summary: Your needs don’t matter! Put everyone else first, even if it means starving.
The Danger: Demoralization, financial stress, decreased motivation, and ultimately, burnout.
The Antidote: Prioritize your own financial well-being and ensure that you’re adequately compensated for your hard work.
17. #20: Worry About The Opinions Of Others!
Summary: Let the fear of judgment dictate your every move.
The Danger: Decreased profits, increased costs, lost opportunities, and damaged reputation.
The Antidote: Develop confidence in your own decisions and focus on what’s best for your business, not on what others think.
18. #21: Correct Mistakes In Public!
Summary: Humiliate your employees for their mistakes. It builds character!
The Danger: Damaged morale, a negative work environment, and a damaged reputation.
The Antidote: Correct mistakes in private and offer constructive feedback and support.
19. #22: Let Bad People Fester In Your Organization!
Summary: Ignore the toxic employees and let them spread their negativity.
The Danger: A damaged reputation, decreased productivity, and a toxic work environment.
The Antidote: Identify and remove bad people from your organization quickly.
20. #23: Burn Bridges: Piss People Off So They Won’t Help!
Summary: Alienate everyone in your network and go it alone!
The Danger: A loss of valuable resources, a damaged reputation, and missed opportunities.
The Antidote: Build strong relationships with people and treat them with respect.
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