How small business owners can escape price-driven competition by redefining their market and creating a new category instead of competing in crowded spaces.

Show Notes Page: https://www.thehowofbusiness.com/600-kevin-maney-create-your-category/

Many small business owners enter crowded markets and end up competing primarily on price. But according to author and business strategist Kevin Maney, there is another path: create your own category.

In this conversation, Henry Lopez speaks with Kevin Maney about the ideas in his latest book "The Category Creation Formula." The discussion explores how entrepreneurs can redefine the problem they solve and differentiate their business in ways that eliminate direct price competition.

Kevin explains that market categories exist primarily in the minds of customers. Businesses that successfully define a new category often become the default leader in that space and capture most of the attention and economic value. Rather than competing to be slightly better or slightly cheaper, the goal is to become meaningfully different.

Kevin introduces the Category Creation Formula: Context + Missing + Innovation = New Category

First, business owners must understand the context of how their customers' world is changing. Next, they identify what is missing in the current solutions. Finally, they introduce an innovation that solves that missing piece in a compelling new way.

The conversation also explores the importance of storytelling in marketing. Instead of starting with features or products, businesses should begin with the problem customers experience. When customers feel understood, they become more open to new solutions.

As Kevin explains: "It's better to be different than to try to be better."

Through examples ranging from laundromats in Brooklyn to dishwasher repair services, Henry and Kevin demonstrate how entrepreneurs can redefine a problem, create a new category, and stand out even in highly saturated markets.

If you're building or growing a small business, this episode offers practical insights into escaping the trap of competing only on price.

Kevin Maney is a bestselling author, longtime business journalist, and co-founding partner of Category Design Advisors, where he helps leadership teams define and lead new market categories. He previously co-authored the influential book Play Bigger, which introduced the concept of category design to mainstream business audiences. Kevin's writing has appeared in major publications including Newsweek, Fortune, Wired, USA Today, and The Atlantic.

This episode is hosted by Henry Lopez. The How of Business podcast focuses on helping you start, run, grow and exit your small business. The How of Business is a top-rated podcast for small business owners and entrepreneurs. Find the best podcast, small business coaching, resources and trusted service partners for small business owners and entrepreneurs at our website https://TheHowOfBusiness.com

When to outsource your bookkeeping, how outsourcing compares to hiring an in-house bookkeeper, and best practices for working effectively with a bookkeeping service.

Show Notes Page: https://www.thehowofbusiness.com/599-outsource-your-bookkeeping/

Knowing when to outsource your bookkeeping is an important decision for small business owners. As your business grows, bookkeeping becomes more complex, more time-consuming, and more critical to making informed decisions.

In this episode, Henry Lopez is joined by bookkeeping expert Jodi Arrant to discuss when it makes sense to outsource your bookkeeping instead of doing it yourself or hiring a bookkeeper in-house. They explore the common signs that indicate it's time to get help, the advantages of outsourcing, and what to look for when choosing a professional bookkeeping service.

Henry and Jodi also explain how business owners should work effectively with a bookkeeper to ensure accurate financial reports and better decision-making. Even when you outsource bookkeeping, Henry emphasizes that business owners must stay engaged with their financials and review their reports regularly.

"If you're running your business without accurate financials, you're steering partially blind." - Henry Lopez

They also discuss practical best practices for reviewing financial reports, communicating with your bookkeeper, and building the processes needed to keep your financial records accurate and useful.

Henry also shares more about The How of Business: Bookkeeping, a service designed specifically for small business owners who want professional bookkeeping support without hiring a full-time bookkeeper.

This episode is hosted by Henry Lopez. The How of Business podcast focuses on helping you start, run, grow and exit your small business. The How of Business is a top-rated podcast for small business owners and entrepreneurs. Find the best podcast, small business coaching, resources and trusted service partners for small business owners and entrepreneurs at our website https://TheHowOfBusiness.com

If your leaders don't know how they're measured, you can't expect consistent performance or real ownership.

Show Notes Page: https://www.thehowofbusiness.com/598-do-your-leaders-know-the-score/

Frustrated with inconsistent performance from your managers or senior team members? The issue may not be motivation, it may be measurement.

In this episode, Henry Lopez breaks down why leadership performance problems often stem from a lack of role clarity, measurable outcomes, and transparent KPIs.

Without clearly defined metrics, even highly motivated leaders drift. Expectations become subjective. Feedback becomes emotional. And performance becomes inconsistent.

Henry explains the difference between expectations and KPIs and why outcomes, not activity, must be measured.

He walks through:

How to define company-level KPIs first

How employee KPIs must roll up to business goals

Why 2 to 5 KPIs per leader is the right number

The importance of transparency in formulas and data sources

Why ownership requires control

How KPIs improve engagement, fairness, and accountability

As Henry says, "If employees don't know how you measure their performance, you can't expect them to win."

If you want stronger leadership, clearer accountability, and more consistent results in your small business, this episode provides a practical framework you can implement immediately..

This episode is hosted by Henry Lopez. The How of Business podcast focuses on helping you start, run, grow and exit your small business. The How of Business is a top-rated podcast for small business owners and entrepreneurs. Find the best podcast, small business coaching, resources and trusted service partners for small business owners and entrepreneurs at our website https://TheHowOfBusiness.com

Five practical reasons your small business will sell and how to intentionally build long-term exit value.

Show Notes Page: https://www.thehowofbusiness.com/597-why-your-business-will-sell/

Most business owners say they want to sell one day but very few actually build a business someone would want to buy.

In this episode, Henry Lopez outlines five practical reasons your business will sell and the disciplines required to build exit readiness long before you're ready to exit. A sellable business isn't created at the moment you decide to sell - it's built over years through intentional design.

Henry shares the five core elements that dramatically increase sellability:

A scalable, repeatable offer
Predictable and recurring revenue
Documented systems
Owner independence
A credible growth story

Visit the show notes page for this episode to download the Business Sellability Scorecard.

Referencing ideas from Built to Sell by John Warrillow, Henry reinforces the principle that "a sellable business is a productized business" - one with clearly defined and standardized offerings instead of highly customized one-off projects.

Whether you plan to sell or not, building a sellable business creates greater freedom, stronger profitability, and more control over your future.

This episode is hosted by Henry Lopez. The How of Business podcast focuses on helping you start, run, grow and exit your small business. The How of Business is a top-rated podcast for small business owners and entrepreneurs. Find the best podcast, small business coaching, resources and trusted service partners for small business owners and entrepreneurs at our website https://TheHowOfBusiness.com

How AI is reshaping small business marketing and why clear positioning and strong messaging matter more than ever.

Show Notes Page: https://www.thehowofbusiness.com/596-shannon-bailey-marketing-and-ai/

Branding and messaging expert Shannon Bailey shares her entrepreneurial journey and explains (starting at 11:10) why clear positioning and concise messaging are essential in the AI-driven marketing era.

As AI tools like ChatGPT reshape how customers search for information, small business marketing is entering a new era that rewards clarity over cleverness and positioning over fluff.

In this episode, Henry Lopez chats with branding and messaging strategist Shannon Bailey, founder of Make Progress Strategies. Shannon begins by sharing her entrepreneurial journey, from a career in sales and corporate leadership to launching her own consulting firm, and what led her to take that leap into business ownership.

We then explore how AI is changing marketing. Shannon explains why AI doesn't make marketing more technical, but more strategic. As AI platforms synthesize and recommend businesses instead of simply listing search results, vague positioning and generic messaging get exposed quickly.

We discuss why small businesses may actually benefit in this shift, how earned authority now matters more than SEO tricks, and why niching down expands your reach instead of limiting it. Shannon also shares practical steps you can take today, including how to test your visibility using AI tools themselves.

If you're feeling overwhelmed by AI disruption, this conversation will help you refocus on the fundamentals: clear messaging, strong positioning, and speaking directly to your ideal client, while also offering inspiration from Shannon's own path into entrepreneurship.

Shannon Bailey is a strategist and branding and messaging expert. She is the founder of Make Progress Strategies, where she helps small businesses and nonprofits clarify their value proposition, align brand positioning with growth objectives, and build strategic marketing plans that drive action.

This episode is hosted by Henry Lopez. The How of Business podcast focuses on helping you start, run, grow and exit your small business. The How of Business is a top-rated podcast for small business owners and entrepreneurs. Find the best podcast, small business coaching, resources and trusted service partners for small business owners and entrepreneurs at our website https://TheHowOfBusiness.com

Planning improves your odds of success, but accepting risk, making decisions with incomplete information, and learning quickly from failure are what ultimately move a business forward.

Show Notes Page: https://www.thehowofbusiness.com/595-plan-to-succeed-prepare-to-fail/

Planning is essential to building a successful small business, but it doesn't eliminate risk or guarantee success. In this episode, Henry Lopez explains why business owners must plan to succeed while also being prepared to fail, and how accepting uncertainty is a prerequisite for growth.

Henry breaks down the role of planning in both startups and existing businesses, explaining how business plans, financial projections, and annual strategic plans help reduce - but never remove - risk. He also explores the emotional side of failure, including fear, embarrassment, and decision paralysis, and why waiting for certainty often leads to stagnation.

Drawing from personal experience and past episodes, Henry outlines a practical framework for balancing disciplined planning with courageous action:

1 - Plan deliberately
2 - Assess the downside
3 - Decide and commit
4 - Review and adjust

The goal is not to avoid mistakes entirely, but to build a business resilient enough to survive them.

If you're stuck overanalyzing, afraid of making the wrong move, or hesitating to launch or grow your business, this episode will help you reframe risk, overcome fear, and move forward with confidence.

This episode is hosted by Henry Lopez. The How of Business podcast focuses on helping you start, run, grow and exit your small business. The How of Business is a top-rated podcast for small business owners and entrepreneurs. Find the best podcast, small business coaching, resources and trusted service partners for small business owners and entrepreneurs at our website https://TheHowOfBusiness.com

How to overcome Decision Paralysis - assessing risk, limiting over analysis, and taking action are essential to moving a business forward.

Show Notes Page: https://www.thehowofbusiness.com/r423-overcoming-decision-paralysis/

Decision paralysis keeps entrepreneurs stuck, and learning how to assess risk, limit over analysis, and take action is essential to moving a business forward.

Decision paralysis, often called analysis paralysis, can quietly stall a small business or prevent an entrepreneur from ever getting started. In this episode, Henry Lopez and guest co-host David Begin unpack why decision paralysis happens, how it shows up differently in big strategic decisions versus daily operational choices, and why small business owners are especially vulnerable to it.

Drawing from real-world experience, Henry and David explain how fear, risk miscalculation, perfectionism, and decision fatigue all contribute to inaction. They explore the difference between intuition and expertise, referencing Malcolm Gladwell's book Blink, and discuss why relying solely on "gut instinct" can be dangerous for new entrepreneurs but powerful for experienced operators.

The conversation also covers practical strategies to break through paralysis, including risk mitigation, breaking big decisions into smaller ones, setting go/no-go dates, and using a "pretend decision" technique to reduce pressure and clarify direction. They emphasize the importance of self-awareness, leadership responsibility, and building teams that can make decisions independently.

As Henry puts it, "There are no guarantees in business, but there is a cost to not deciding."

This episode is a must-listen for anyone feeling stuck, overwhelmed, or hesitant to make the next move in their business.

This episode is hosted by Henry Lopez. The How of Business podcast focuses on helping you start, run, grow and exit your small business. The How of Business is a top-rated podcast for small business owners and entrepreneurs. Find the best podcast, small business coaching, resources and trusted service partners for small business owners and entrepreneurs at our website https://TheHowOfBusiness.com

What At-Will Employment really means for small business owners.

Show Notes Page: https://www.thehowofbusiness.com/594-claudia-stjohn-at-will-employment/

At-will employment gives small business owners flexibility, but misunderstandings around documentation, retaliation, and protected classes can quickly turn a termination into a lawsuit.

Most small business owners believe "at-will employment" means they can fire an employee at any time for any reason, but that misunderstanding is one of the fastest paths to an expensive legal dispute.

In this episode, Henry Lopez is joined by returning guest Claudia St. John, founder and CEO of The Workplace Advisors, to break down what at-will employment really means under U.S. law. They explain why at-will employment is not a free pass to terminate employees without consequences, and how common mistakes (like poor documentation, vague termination explanations, and retaliation) create legal risk even when the employer's decision was justified.

Claudia shares real-world examples from her HR consulting practice, emphasizing why documentation of performance issues is critical, how progressive discipline policies can accidentally undermine at-will status, and why honesty during termination conversations actually reduces lawsuits. As Claudia notes, "If an employee is surprised, they're far more likely to sue."

Henry and Claudia also discuss employee handbooks, offer letters, EPLI insurance, and when small businesses should consider professional HR support.

This episode is a must-listen for any business owner who manages employees and wants to reduce risk while still leading with fairness and professionalism.

Claudia St. John is a keynote speaker, bestselling author, and founder and CEO of The Workplace Advisors, a national HR consulting firm that helps small and mid-sized businesses navigate compliance, hiring, and employee management with practical, evidence-based guidance.

This episode is hosted by Henry Lopez. The How of Business podcast focuses on helping you start, run, grow and exit your small business. The How of Business is a top-rated podcast for small business owners and entrepreneurs. Find the best podcast, small business coaching, resources and trusted service partners for small business owners and entrepreneurs at our website https://TheHowOfBusiness.com