How to start and grow a small business without investors.

Show Notes Page: https://www.thehowofbusiness.com/r361-tyler-king-without-investors/

Bootstrapping a software business without venture capital or angel investors lets you grow on your own terms, and Tyler King, co-founder of Less Annoying CRM, shares how he built a profitable, sustainable SaaS company by staying disciplined, customer-focused, and true to what he actually wanted from the business.

Tyler King, co-founder and CEO of Less Annoying CRM, joins the show to share how he bootstrapped a profitable software company. No venture capital, no angel investors, no exit plan, and no rush. He shares what small business owners can learn from building a company on their own terms.

For anyone who assumes a software startup requires millions in funding and a race toward an IPO, Tyler's story is a useful counterpoint. He grew a sustainable, profitable SaaS (Software as a Service) business slowly and deliberately, proving that discipline and patience can be advantages rather than limitations.

Tyler didn't grow up dreaming of running a business. He was a programmer at a venture-backed startup when the 2008 downturn hit and nearly everyone was laid off. Everyone except the five cheapest employees, which happened to include him. With the bosses gone, he spent a year unofficially playing co-founder, and discovered he loved entrepreneurship. In 2009 he and his brother Bracken started what became Less Annoying CRM.

The idea came from real frustration. Tasked with setting up Salesforce at that old job, Tyler (a computer science graduate) spent a month and couldn't make it work. At the time, roughly half of the CRMs companies paid for went unused. So rather than build something with more features, he set out to build something people could actually use.

From there, Henry and Tyler dig into the practical realities of bootstrapping: funding the business from savings and side-job cash flow, why banks won't lend to software companies, and how limited money forces healthy discipline. "How much money did we make this month? That's how much money we can spend," Tyler explains.

He shares hard-won lessons on shipping a minimum viable product (MVP) fast (his first version was "minimum, debatable whether it was viable"), using intuition over thin data, and building a company that can survive any one person (what he and his team call the "hit by a bus" test) which is the same discipline as building to sell. They also cover his unusual culture choices: separating raises from performance, giving everyone "20% time," and recruiting almost entirely from a pool of interns.

Perhaps most striking is how Less Annoying CRM's biggest differentiator - customer service - happened by accident. Tyler put his own phone number on the contact page, and when it rang, the caller was stunned anyone picked up at all.

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

Increase Close Rates with consistent, professional in-home sales presentations for home improvement and home services businesses, and Dean Curtis of Ingage shares the principles and tools that help small operators win more deals at the kitchen table.

Show Notes Page: https://www.thehowofbusiness.com/619-dean-curtis-presentarions-close-deals/

SPECIAL OFFER: 10% OFF the Ingage Pro when you use the code "HOWOFBUSINESS".

For home services businesses, the sale is often won or lost at the customer's kitchen table and Dean Curtis, CEO of Ingage, joins the show to explain how a more consistent, professional in-home presentation can dramatically improve close rates, with client case studies to back it up.

If you sell at the customer's home (roofing, windows, doors, siding, gutters, baths, etc.) then you're trying to convince a homeowner that you're the right person to solve their problem, and that process is highly educational. Too often the materials salespeople bring to present are off-brand, out of order, and different for every salesperson. That inconsistency costs deals. When the content is consistent, on-brand, and matched to a proven sales process, close rates go up.

In this episode of The How of Business, Henry Lopez is joined by Dean Curtis to explore why consistency, trust, and preparation drive home services sales and how the right content levels the playing field so even a one-person shop can look and perform like a 100-person company.

The discussion opens on consistency. In the replacement remodeling market, the same products are sold over and over, the objections are common, and the more consistent a rep's approach, the higher they close. But consistent doesn't mean rigid. Dean uses a bingo-board analogy to explain why the best sales reps move dynamically to answer whatever the customer raises. As he puts it, borrowing from Mike Tyson: "everyone has a plan until they get punched in the face."

From there the conversation turns to trust, which Dean breaks into three drivers: brand (a homeowner judges you within a fraction of a second), personalization (put the customer's own house and name on the first screen), and education (be the guide who makes the homeowner the hero). "No one cares what you can sell, what you can install if they don't trust you," Dean explains.

Dean then shares what separates the teams that win: they train, they practice, and they coach. They don't hand sales teams content and wish them luck. Instead, they build a feedback loop, using analytics to see what's working and coaching reps without it feeling like Big Brother. He also cautions that content is a tool inside the conversation, not a replacement for it.

The episode closes with two grounding reminders for any small business owner: do the same thing every time so you can actually learn what works, and remember that technology is never a silver bullet — start with the problem, not the shiny object. Or as Dean sums up trust: little deposits in the trust bank go a long way.

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

Buying a Business? Do Your Due Diligence!

Show Notes Page: https://www.thehowofbusiness.com/618-buyer-due-diligence/

Buyer due diligence is your primary protection when purchasing a small business, and on this episode Henry Lopez walks through a practical checklist to verify the financials, uncover hidden risks, and avoid overpaying for or buying the wrong business.

Get your FREE DOWNLOAD: Buyer Due Diligence Checklist – from the show notes page for this episode.

Buyer due diligence is the single most important protection you have when purchasing a small business. And skipping or rushing it is how buyers end up owning problems they never saw coming.

Buying an existing business can be one of the fastest paths to successful ownership. You inherit customers, cash flow, systems, and employees, ideally in a proven, profitable model. But things are not always as they appear. A business that's always busy or generating strong revenue isn't necessarily healthy, and you may be inheriting problems that aren't obvious at first glance. Due diligence is how you find those issues before closing, not after.

In this episode of The How of Business, Henry Lopez walks through his buyer due diligence checklist. This checklist includes the key areas you need to investigate, the mistakes that trip up first-time buyers, and how to make sure the business you're paying for is actually the business you think you're buying. Whether you're preparing to buy or getting ready to sell, this is the framework for looking under the covers with confidence.

Henry frames the whole process around an old proverb: trust but verify. A good seller isn't lying to you, but it isn't their job to protect you either. They'll naturally highlight what's great and will likely remain quiet on what's broken. Verification is your job, along with your team of advisors: a business coach, a CPA, and an attorney working together.

He explains why due diligence must be a written condition of your letter of intent or purchase agreement, giving you a defined period and the legal right to walk away. Never waive it, and never buy a business "as is" the way you might buy a used car. He also reframes the three possible outcomes of the due diligence period: 1) the deal is confirmed, 2) the price or terms get renegotiated, or 3) you walk away.

He covers deal structure (why most small business deals are asset purchases and why that's safer for the buyer), and how to validate earnings using seller's discretionary earnings rather than revenue. Because you're not buying sales, you're buying verified profits and the assets that produce them. He shares the typical one-to-three multiple range and warns against buying an unprofitable or owner-dependent business, where you may simply be buying yourself a lower-paying job.

Henry then explains the core investigation areas: legal (good standing, who actually has the right to sell, and the lease traps that can quietly kill a deal), financial (three to five years of statements, reconciling the real flow of cash, and treating unexplained errors as red flags), operational (systems ownership, owner and customer concentration, key-employee retention, and worker misclassification), plus market and risk factors like insurance, regulatory triggers, SBA loan conditions, and franchise approvals.

His closing reminder says it best: "A no that you discover in due diligence is far cheaper than a yes you regret." Slow down, demand complete access, and the deal you clearly understand is the only deal worth doing.

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

Deciding between remote, hybrid, and in-office work is one of the toughest calls small business owners face today, and HR expert Claudia St. John shares how to choose the model that fits your team while staying legally compliant.

Show Notes Page: https://www.thehowofbusiness.com/617-claudia-stjohn-remote-workers/

Small business owners are still wrestling with one of the most consequential management decisions of the modern workplace, and HR expert Claudia St. John, founder and CEO of The Workplace Advisors, returns to help them get it right.

Remote, hybrid, in-office? Years after the pandemic forced the question, there is still no single right answer, and the wrong choice quietly costs businesses in productivity, culture, retention, and even legal exposure. What works for a large tech company may be exactly wrong for your small business, and copying someone else's policy is not a strategy.

In this episode of The How of Business, Henry Lopez is joined by Claudia St. John to explore how small business owners should think through the remote-versus-hybrid-versus-office decision and how to make whichever model they choose actually work.

Claudia is a keynote speaker, best-selling author, and the founder and CEO of The Workplace Advisors, an HR consulting, recruiting, and training firm that specializes in helping small businesses. As one of Henry's trusted service partners, she is who he refers his own clients to for HR support and compliance, which makes her a credible guide through a decision most owners are still making by gut feel.

The conversation opens with the current state of work: a "frozen labor market" where economic uncertainty has businesses reluctant to hire but unwilling to lay off, sitting on top of a longer-term demographic squeeze as baby boomers exit and fewer younger workers replace them. Against that backdrop, Claudia unpacks what the data actually say about remote work including the finding that full-time remote employees are often more productive but noticeably less happy and more isolated.

She and Henry dig into the human cost of going fully remote: the loss of collaboration, the subtle body-language signals a manager can't read over video, and how distance can quietly turn departments adversarial.

"When you're not encountering each other regularly, you lose empathy toward what somebody else is experiencing," Claudia notes.

A surprising theme emerges: the younger workers everyone assumes want to stay home actually crave connection and flexibility, not isolation.

From there the discussion turns practical: why regular cadence meetings matter even when there's "nothing to talk about," why accountability is really a problem of clear expectations rather than physical presence, and the legal and compliance traps of employing people across multiple states. Claudia's throughline for owners still stuck on the question is simple — start by asking why, and listen from the bottom up."

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

Why work expands to fill the time available, and how small business owners can use deadlines, time blocking, and clear outcomes to get more done in less time.

Show Notes Page: https://www.thehowofbusiness.com/616-parkinsons-law-for-small-business/

Have you ever noticed that a task you expected to finish in a day somehow ends up taking all week? Parkinson's Law explains why and understanding it can help small business owners reclaim their most limited resource: their time.

Parkinson's Law is the principle that work expands so as to fill the time available for its completion. Give yourself an entire day to complete an administrative task and it will often consume the entire day. Give your team two weeks to finish a project and much of the meaningful work tends to happen in the final two days. For small business owners, this helps explain why we feel constantly busy, why meetings and projects drag on, and why there never seems to be enough time for the high-value work that actually grows the business.

In this episode of The How of Business, Henry Lopez explores how understanding Parkinson's Law can help you and your team make faster progress and use your limited time more effectively without simply working longer hours.

The concept was introduced by British historian and author C. Northcote Parkinson in a 1955 essay in The Economist. His observation was simple: when more time is available, work tends to become more complicated and consume all the time available. It's a bit like a bigger house that we fill with more stuff. The more time we have, the more we tend to fill it. Give yourself an hour to write an email and you may spend the full hour refining it; give yourself fifteen minutes and you'll likely communicate the same message just as well.

Henry, a self-described perfectionist, is candid about how this applies to his own work, where the pursuit of perfection often produces diminishing returns. The first 80% of a result might take two hours, while chasing perfection can consume six more without making it materially more valuable to the customer.

When work continually expands, the consequences add up: higher labor costs, slower execution, delayed revenue, missed opportunities, decision fatigue, too much owner involvement, and less time for planning and growth. Henry also raises a hard question worth sitting with: does your business culture reward activity instead of results?

The heart of the episode is a set of eight practical tactics for putting reasonable constraints around your work, plus five questions you can ask to right-size any recurring task or project.

As Henry puts it, "Don't just ask how much time do we have. Instead, ask how much time should this result require?"

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

Technology expert explains how small business owners can leverage AI as a force multiplier while protecting their data, systems, and intellectual property from emerging cybersecurity risks.

Show Notes Page: https://www.thehowofbusiness.com/615-mordy-hackel-ai-cybersecurity /

Artificial intelligence is creating enormous opportunities for small businesses—but it is also introducing new cybersecurity, data, and operational risks.

In this episode of The How of Business, Henry Lopez is joined by technology entrepreneur and KJ Technology founder Mordy Hackel to explore how small business owners can embrace AI, use technology as a force multiplier, and protect their businesses as the technology landscape continues to change.

Mordy shares his entrepreneurial journey from studying economics and working in technology for organizations including the NBA, Sony Music, and Citibank to building KJ Technology, a Manhattan-based managed IT services firm he has been growing since 1998.

Henry Lopez and Mordy Hackel discuss why small businesses should not assume they are too small to be targets for cybercrime. AI is making phishing emails, voice impersonation, social engineering, and other attacks increasingly sophisticated. Small organizations may be particularly vulnerable when they lack established procedures for authorizing payments, sharing sensitive information, or granting access to systems.

They also explore another increasingly important issue: employees using AI tools independently. When employees use personal ChatGPT, Claude, or other AI accounts for company work, businesses may expose confidential information or lose valuable intellectual property and institutional knowledge when those employees leave.

But the message of this episode is not to be afraid of AI. Mordy believes the opportunities significantly outweigh the risks. The challenge is learning how to use the right technology for the right problem.

AI can help business owners think creatively, analyze problems, overcome writer's block, develop workflows, prototype applications, and identify opportunities to improve how their businesses operate.

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 he earned his way into leadership, developed a capable management team, and transformed a hands-on family equipment dealership into a scalable business that no longer depends on him for every decision.

Show Notes Page: https://www.thehowofbusiness.com/614-kaiden-routh-growing-family-business/

How do you step into a multigenerational family business, earn the respect of employees and customers, and then change how the company operates without damaging its legacy?

In this episode, Henry Lopez is joined by Kaiden Routh, CEO of Routh Sales and Rentals, a second-generation family-owned equipment dealership with locations in Oklahoma and Arkansas.

Kaiden grew up around family businesses and initially considered pursuing a different career. When he eventually joined the family company, he was not immediately placed in charge. He worked at the parts counter, supported the service department, handled sales, and learned nearly every part of the operation.

That experience helped Kaiden understand the business and earn credibility with employees. However, stepping into leadership created a different challenge: longtime customers and team members were accustomed to bypassing him and going directly to his father.

Kaiden explains how he and his father navigated that challenging transition, established new boundaries, and accepted that the next generation would need to operate the business differently.

Henry and Kaiden also discuss Kaiden's evolution from being the person who solved every problem to becoming a CEO focused on growth, people, culture, customer experience, and the future growth of the company.

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

Do you possess the innate characteristics, the 6 essential traits, required to become a true entrepreneur?

Show Notes Page: https://www.thehowofbusiness.com/r346-6-traits-of-entrepreneurs/

How to honestly assess whether you possess the 6 essential traits required to become a true entrepreneur.

Henry explains the critical difference between being self-employed or a small business owner and being a true entrepreneur, and why not everyone is wired to build an organization that grows beyond themselves.

He shares the six essential traits that, according to Gino Wickman, and based on Henry's own decades of entrepreneurial experience and coaching, are innate characteristics required for entrepreneurial success.

If you're considering starting a business, or wondering whether entrepreneurship is truly the right path for you, this episode will help you honestly assess yourself before making the leap.

The 6 Traits of Entrepreneurs:

1. Visionary
2. Passionate
3. Problem Solver
4. Driven
5. Risk Taker
6. Responsible (Blames No One)

Key Takeaways from this episode: The difference between self-employment and entrepreneurship. Why entrepreneurial success requires more than a great idea. The six essential entrepreneurial traits of entrepreneurs. Why these traits are considered innate and not learned. How honest self-assessment can save years of frustration. Why entrepreneurship isn't the right path for everyone, and that's okay!

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 understanding the neuroscience behind conflict can help small business owners become more effective leaders, build healthier teams, and transform workplace conflict into collaboration.

Show Notes Page: https://www.thehowofbusiness.com/613-jeremy-pollack-conflict-resolution/

Conflict is inevitable in every small business. But according to conflict resolution expert Jeremy Pollack, conflict itself isn't the problem. It's how our nervous systems respond to perceived threats that determines whether conflict becomes destructive or productive.

In this episode, Henry Lopez talks with social-organizational psychologist, mediator, and author Jeremy Pollack about the neuroscience behind workplace conflict and why better communication alone isn't enough. Jeremy explains that before teams can solve problems effectively, leaders must first learn how to regulate their own nervous systems and create an environment where others feel psychologically safe.

Drawing from his book Wired for Peace: Using Seven Neuroscience-Based Principles to Resolve Conflicts, Jeremy shares practical strategies that every small business owner can apply immediately to improve leadership, strengthen culture, and reduce unnecessary workplace tension.

Whether you're managing a growing team, navigating difficult employee conversations, or simply wanting to become a more effective leader, this episode offers practical, science-backed tools you can begin using immediately in your small business.

Jeremy Pollack, Ph.D., is a social-organizational psychologist, workplace conflict resolution expert, and author of Wired for Peace, helping leaders build healthier, more collaborative teams through neuroscience-based conflict resolution. He is the founder of Pollack Peacebuilding Systems.

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

A Waymo driverless vehicle ride sparks a discussion about AI, innovation, technology adoption, and why small business owners can't afford to wait for perfection before embracing emerging technologies like AI.

Show Notes Page: https://www.thehowofbusiness.com/612-waymo-and-innovation/

Henry Lopez and returning guest host David Begin recently experienced something neither of them will soon forget - their first ride in a fully driverless Waymo vehicle in downtown Miami.

What starts as a fascinating technology experience quickly turns into a broader discussion about artificial intelligence, disruption, innovation, and what every small business owner should learn from emerging technologies.

They explore why driverless vehicles are advancing faster than many people realize, why new technologies are often judged against impossible standards of perfection, and why businesses that wait until technology is "perfect" risk being left behind.

From autonomous vehicles to AI tools, Henry and David discuss how business owners can develop the mindset needed to stay competitive in an era of rapid technological change.

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