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Building beautiful businesses. I’ve spent the last 30 years leading, building, and growing my holding company. Entrepreneurship done right makes the world a better place. My track record of success: - Employ 600+ people - Built 12+ businesses across multiple industries - Audience in the hundreds of thousands - Chili's & Subaru evangelist (unpaid)
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Amazon was this close to killing Barnes & Noble. But now they’re on a crazy comeback, opening new stores all over America. How did they do it? Let’s head back to 2011, the bookstore industry is in shambles. Why? Amazon. Amazon changes the game by selling books online. That takes a chunk out of bookstores’ traffic. But then Amazon goes even further, and launches the Kindle — making e-readers suddenly popular, and making physical books obsolete. Borders—the #2 bookstore in America—goes bankrupt almost overnight. So, everyone thinks Barnes & Noble would be next. In a desperate move, Barnes & Noble tries to compete by spending over a BILLION dollars on their own e-reader, the Nook. It flops spectacularly. They pivot, and start filling stores with puzzles, board games, toys—anything to survive. But nothing is working! Their stock tanks 80%. They’re closing stores all over the place. Things look hopeless. So they tried something totally crazy… They turn into the anti-Amazon — every location is tailored to the community, [down to the wallpaper], stocked with books that the locals want to read, and stop trying to be the everything store. Then TikTok catches on, and book lovers online start going nuts for old fashioned bookstores. Barnes & Noble is back.
Why would anyone sell a business that makes $1.5 million a year… and only requires 10 hours of work per week? In today’s video, I unpack a common scenario we see all the time on our podcast Acquisitions Anonymous—a profitable, automated business comes to market, and everyone asks the same thing: “Why would the owner walk away from this?” The answer might surprise you. It’s not about money. It’s about psychology, identity, and what happens after 20 years of building something from scratch. If you’re an aspiring business buyer, operator, or just curious about the world of small business acquisitions, this is a must-watch. You’ll get insight into how seasoned operators think, why seemingly perfect businesses are sold, and what freedom really looks like after building wealth. Thoughts?
Stop hiring people who aren’t a good fit. Here are 8 tips to help you get it right the first time. (plus a bonus tip at the end) 1) Know what type of brain the role needs. Not everyone thinks like you. That’s a good thing. Some roles need creative chaos. Others need precision and pattern recognition. Some people light up when you give them a blank canvas. Others thrive in structure. So figure out what type of person will thrive in this role, then seek them out. 2) Use the CWG test. From the EOS playbook, the best hires pass the “CWG” test: • Can do the job (skills, horsepower) • Want to do the job (they’re motivated) • Get it (they understand the mission and culture) All three matter. You can’t coach someone to “get it.” 3) Watch out for high-charisma, low-output. Some folks are amazing in interviews. Polished, personable, quick on their feet. But then don’t have what it takes when they’re actually in the seat. That’s where it pays to read between the lines on the resume. Make sure they have a track record (with references who’ll vouch for it) to back up their talk. 4) Avoid building teams of people just like you. I’m an idea guy. But I didn't get that every person is wired differently, and for a long time I mostly hired other idea people, because I liked to talk to them. I would get annoyed by different thinkers. But then my teams would have tons of ideas, but get nothing done. Hire people who fill in your blind spots. 5) If the timing’s wrong, any hire is the wrong hire. This one’s true for early-stage founders especially: wait for the right time to hire. Don’t hire with a half-baked idea and one customer. It’s all about the right inflection points — customer traction, revenue growth, etc. Pull the trigger too early, and you’re just creating overhead and squeezing your resources. 6) Watch out for toxic people. Toxic doesn’t always mean incompetent. It means corrosive. Because some employees can hit their numbers and still drag your team down. Red flags: 🚩 Constant drama 🚩 Gossip levels rising 🚩 Good employees avoiding them 🚩 “The vibe feels off” 7) Run your references. I use a “threat of reference check”: I tell every candidate I do up to 5 hours of reference calls, when it’s a senior position. If someone bristles, that’s a bad sign. Good candidates are happy, because they know their previous contacts will talk them up. Bad candidates drop out. 8) Don’t rush to fill the seat. This one’s tough—especially when a team is stretched thin. But rushing a hire almost always backfires. If you have to talk yourself into someone — don’t do it. Hiring slowly sucks. Firing fast sucks more. You’ll have a lot less regret with the former than the latter. Bonus Tip: Write a hiring memo. Before you make an offer, write a 2-page memo to yourself. Reflect on: • Where are they strong? • Where are they weak? • How can we help them? • Why should we hire them? It’s also a great snapshot you can look back on.
If you’ve ever considered buying a business, watch this first. You’ve probably heard it before: “10,000 baby boomers are retiring every day... and no one’s around to buy their businesses.” That’s the promise sold by gurus, masterminds, and info-product peddlers claiming it’s easy to walk into entrepreneurship by buying a business. But is it true? In this video, I rant about the reality of business buying, why most deals are way harder than advertised, and how this industry has quietly become another dream-selling machine. I’ll break down the myths, share personal stories, and explain why you need to be way more skeptical about the “easy path to wealth” narrative. Drop your thoughts in the comments. And follow for more real-talk on entrepreneurship, business buying, and strategy.
The SBA 7(a) loan program might be the greatest small business tool most Americans don’t fully understand. In this video, I break down why this program is so important to preserving the backbone of the American economy: small businesses. Forget the noise from Washington. This isn’t about politics — it’s about economic mobility. SBA 7(a) loans allow everyday Americans to buy profitable businesses — even if they don’t come from money. I share personal stories, data, and why this program changes lives. What’s your take on this?
Cold outreach that actually works. The 7 keys to getting replies. Eventually. 1) Meet your audience where they’re at. Not all cold outreach is email. Boomers and Gen X? Email. Younger people? Text or social media. You can spend all the time and money in the world — but if your message lands in the wrong place, it’s wasted. 2) Use the scientific method. Running high-volume outreach? Treat it like an experiment. Test subject lines, timing, messaging — anything that could move the needle. 3) One thing that always wins: short, custom messages > long copy-pastes. One of my best emails said: “Dear Jim, would you like to talk about selling your business? If so, let me know.” Subject line? Just the business name. It crushed. 4) Offer an easy yes. You’re not closing a deal in one message. You’re just starting a conversation. “Want to talk about selling your business?” That’s an easy ask. 5) Do your homework. People know when you’ve blasted the same message to 1,000 others. Spend 2 minutes Googling. Mention a post, deal, or industry insight. It builds instant credibility. 6) Timing > talent. Even great messages flop if the timing’s off. So follow up. Then follow up again. Persistence (without being annoying) is a superpower. 7) Know when to walk away. If someone’s not interested, don’t force it. And if they’re a bad fit, move on. Outreach is a volume game — but chasing every lead forever is a waste. Hopefully, you find these tips useful and they help you close a sale or two. Anything to add here? Follow Michael Girdley for more business content.
These won’t be true about all Boomers, especially those on the fringes of their age group. But these tips will work with most of them. Before we start — I’m a Gen X myself, and these are just my personal observations. Here we go! — 1. Motivate Boomers with “You are valued” and “You are needed” Boomers often defined themselves by career achievements and wealth. Now that they’re nearing retirement, they want to keep being useful. Create ways for them to be essential and watch them thrive. 2. Help Boomers finally create work-life balance A lot of Boomers worked so hard that their relationships suffered. They have the highest divorce rate of any generation ever… and they invented the “Workaholic” lifestyle! By now, many of them are wondering if it was worth it. This is your chance to show them a more balanced lifestyle. 3. Recognize and respect their long experience They paid their dues when lifetime employment was a thing. So years on the job matter a lot to them. Make use of their long experience. The challenge: they have a mindset of “We paid our dues and you should too.” This can conflict with other generations. 4. Appeal to Boomer idealism Despite often taking the American Dream to an extreme, Boomers grew up during peak American idealism in the post-war years. So Boomers want to feel like they’re working towards a noble mission. What story is your business pursuing? Can you frame it to motivate them? 5. Expect Boomers to sometimes be judgmental If you go against their core values or ideals, you’ll get a harsh earful! This appears especially in conflicts between Boomers and other generations, when they feel like they’re objectively in the right. Be patient with this, but stand your ground. 6. Give Boomers something to put on their wall No generation loves physical trophies and awards like Boomers, so put them out front and in the spotlight. Publicly show your appreciation with physical tokens of respect. 7. Engage Boomers in person Their generation grew up when all important work happened face-to-face. So they’ll take things seriously when you show up with your physical presence. They are the most diplomatic generation, so they won’t tell you… But they’ll love you. 8. Say “call me anytime” Boomers grew up with just landline telephones. No email, text, or even fax. So they appreciate cutting out the back and forth of written communication. Pick up the phone – and invite them to call you. They’ll feel like you “get” them, and you’ll head off a ton of frustration on their part. 9. Put Boomers on teams They see work as a team sport and love consensus. For them, meetings are the way to get things done. And, as they age, Boomers appreciate hierarchy even more — so make that hierarchy clear. You don’t have to put them in charge every time, but they need to know where they fit into the picture. Put people together across different generations. They can be a great balancing force in teams of Millennials and Gen Xers.
What to do when a key employee leaves. Losing a star player can affect your business in many different ways, including experience, systems knowledge, customer/team rapport, and momentum. It’s always going to suck. But how you handle it can make the difference between a bump in the road or a disaster. Because there’s a silver lining, too: it’s your kick in the butt to clean up systems, develop other staff, and rethink roles for the future. Here’s what to do: 1) Transfer and document everything. Assuming you have two weeks' notice, your immediate job is to get as much information documented as possible. Make it their #1 priority, over any of their day-to-day stuff. Capture their processes: how they do their daily tasks, their monthly reporting, their customer notes, even where files are saved. Make sure you have complete contact details for clients and vendors. Find the lightest-lift way to do this — it could be writing things down, it could be video walkthroughs, it could be meetings (just make sure to record them). Then, have them put all their account logins and passwords into a company-owned password manager — and double check that no 2FAs will send a code to their personal devices. (By the way: this is a great time to make sure you have basic cybersecurity set up for your business.) 2) Protect the business. Call a lawyer to make sure you’re fulfilling all employment law obligations. Remind the departing employee of any NDAs, confidentiality, or non-compete terms, if they’re legal for your business. If they didn’t sign one when they started, you can ask — but they’re under no obligation to sign on the way out. 3) Sort out short-term coverage. Figure out who will temporarily cover their workload. Ask the departing employee for advice on who would be a good fit. 4) Tell the team. Don’t delay this one—it's better they hear it from you so they know things are under control. Be clear and calm. Share your plan for covering their work. Open the floor to questions or feedback. Your most important job is to reassure everyone that the business is stable and no one else’s job is at risk. 5) Hold an exit interview. Lots of people have opinions about exit interviews. Don’t wimp out. This is a huge opportunity to get honest feedback. Set your feelings aside, and listen. You might learn something that keeps the next A-player. 6) Make a last-day plan. Figure out the logistics: shutting off system access, collecting company property, final payments, benefits policies, etc. 7) Reflect. Ask yourself some key questions: • Why did we lose this person? • Do we need to hire for this exact role, or can we restructure it? • Is there someone on the team ready to grow into this position? Use this as a prompt to revisit your org chart and update your succession plans. – Agree with these? What would you add? Thanks for reading. Follow Michael Girdley for daily business content ✅
Stealing this one from my Twitter because it will change your life as a business owner. I asked an auditor: "What's the #1 way to prevent theft as a business owner?" He said: "Simple. Each month, review every transaction. Don't hide that you're doing it." Sometimes the simplest solutions really are the best ones. Haven't had a problem since. Repost to save your fellow entrepreneurs some headaches ♻️ Follow Michael Girdley for more business content ✅
I know people hate this fact but: There's a strong correlation between accomplished people and how quickly they respond to email.
7 "Nice Life" careers that make good money and have low time requirements. Stop running on sand and start thinking about these. — My criteria for "Nice Life" careers: • Lots of headroom to grow • Can earn $200,000+ per year • Low capital and time requirements • Good work-life balance • Defensible, durable, and inflation-resistant • Medium to low-risk — 1. Niche consulting. Find a platform that is mission-critical to a small niche of people or businesses. Get really, really good at it. Then you offer your services on either a project-based or time-based system to clients. — 2. Start a digital agency. Examples include coding agencies, SEO agencies, digital ad agencies, and Twitter ghostwriting. You’re basically offering your specific services to businesses or individuals basically as a product. The cool thing about this one: very low barrier to entry. You can get started as a side hustle while doing your day job. There's almost infinite demand for some of this stuff, like SEO, because people want their websites to show up in Google. It doesn't require much capital to get started. — 3. Become a franchise owner. While franchises often require a pretty high spend up front, you’re paying to de-risk the business. Buying a McDonald's, Orange Theory, or Chili's isn’t cheap, but they’re super winning franchises. The people selling the franchise to you know very well where to put them and what makes them work. Your job is to run that playbook, and there are lots of government funding opportunities available to help you fund and grow franchised businesses. — 4. Real estate private equity. Got a nose for a land deal? Then RE PE is another low capex business I love. You take investor money, deploy it into real estate deals, and earn fees and upside. You get to magnify your level of ownership of real estate by using other people's money and sharing in the upside. Real estate is a ginormous market, super tax-advantaged, and can scale over time. — 5. Staffing firm Despite it being essential for success, lots of businesses suck at bringing in the right people. I started and own a business that helps companies staff people overseas. There are lots out there. And you can start on your own, sourcing candidates and job postings, then making the right connections. — 6. Commercial real estate broker Like a regular real estate broker, but for business transactions. The clients are very professional, and everyone just wants to get the job done. A lot of commercial real estate trades at high valuations, so your commissions can be much better when the deals are bigger. — 7. Financial or wealth planning adviser Getting into the wealth management business involves helping people plan for retirement. You can build up your book of business at a big firm, consulting with customers to help them plan for retirement and savings. The market is enormous, and you get to build great relationships with people. — Any careers to add?
It's a very delicate situation. This is how I go about it. How to fire someone with kindness: DISCLAIMER: Terminating employees always sucks. But like hiring, it’s an unavoidable task. I try to remember employees are humans and deserve kindness and respect. No matter the reason. OK, with that said, here are the steps to do it when you’re forced to let someone go: First step, get all your ducks in a row. Specific rules vary by location, but always do this in compliance with laws. There are three main reasons to terminate employment: • Performance • Misconduct • Restructuring/downsizing Document everything. — Then, consider severance. It’s not required everywhere, but I think it’s always the right thing to do. And I’ve never regretted it. If your company can’t afford it, you can try to help them find a new role: • a letter of reference • connecting them with someone It’s good karma. — Next, put all the details in a letter. Pay, benefits, severance, confidentiality clauses, etc. Consult your legal and HR professionals on this, too. — Now comes the conversation. Just be straight with people — direct but kind. You want to show people the respect they deserve. Expect them not to hear much after saying “we’re letting you go”. They’ll be in shock even if they expected it — that’s why a detailed letter is so important. — Here’s how to run the meeting with the employee: 1. Book a 20m meeting first thing in the morning, at least 1 day in advance. Face-to-face is ideal. 2. Open by stating this will be a difficult conversation 3. Clearly state you’re letting them go, and that the decision is final 4. Explain why: policy violation, budget, whatever. Don’t mince words. 5. Clearly state today is their last day. Tell them when they need to be out of the office. Keep this window short. 6. Pause and acknowledge this is difficult. Ask if they have questions or feedback. 7. Go through the details in the paperwork. 8. Ask them to review the termination agreement, and tell them the deadline to return it. 9. When you’re done, go for a walk, buy yourself a drink, do whatever you do. — Finally, announce it to your team. If you think they need it, hold an all-hands meeting that afternoon after the employee leaves. - Take ownership - Talk about what could have been done differently - Ask for questions Expect questions about who will handle their workload. If you’re asked uncomfortable or confrontational questions, acknowledge the feedback and say thank you. And remember: “I don’t have an answer right now” is a fine answer. — Last thing: never badmouth the person you’re letting go. It’s a bad look. And it makes everybody nervous they might be next. — I think firing with compassion is essential to being a good person. Treat the people around you the way you want to be treated. What did I miss? Let me know in the comments! Follow Michael Girdley for more business content ✅
Everyone’s screaming that the economy is about to crash — comparing it to 2008, 2020, even the dot-com bubble. But here’s the thing… this isn’t that. And if you’re panicking right now? You’re looking at the wrong signals. In this video, I break down what’s really happening behind the scenes — from dusty unsold cars to overloaded inventories — and why the panic isn’t coming from the supply side… it’s coming from us. We’ll talk about the impact of post-COVID buying behavior, the ripple effects of recent tariffs, and how a slow-motion unraveling of the economy could actually be more dangerous than a sudden crash. 💬 Drop your take below — are we headed for disaster, or just a painful reset?
Everyone’s talking about how hard it is to buy a business in 2025 — but nobody’s talking about why. It’s not just private equity or search funds… it’s something else entirely. In this video, I break down new data that shows why the pool of available small businesses is drying up — and how adult kids, generational transitions, and shifting job markets are changing the ETA landscape. Whether you're an aspiring business buyer or just trying to understand the new economy, this is a must-watch. Drop your thoughts in the comments and don’t forget to follow for more weekly insights into entrepreneurship, investing, and small business strategy.
The value of diamonds has been totally fake. Now, prices are crashing, and it seems like the balloon might have finally popped. Here’s what’s going on. It all starts in the 1940s: A South African cartel called De Beers controls 90% of the world’s diamonds. But there’s a problem—diamonds aren’t rare, and people don’t want them. So what do they do? They manufacture demand. They have a huge hoard diamonds, but only release a few at a time to keep prices high. Then they launch the most successful marketing campaign in history. Movies, magazines, even school programs teach women to expect a diamond engagement ring. And just like that, every man was suddenly pressured to spend two months’ salary on a glorified rock. By the 2000s, De Beers was making over $6 billion a year selling overpriced stones. But that’s when the trouble started. First, marriage rates have plummeted — so less people are buying engagement rings. Next, social media completely exposed the scam. Suddenly, everybody has heard about blood diamonds, child labor, and the environmental damage diamond mining does. [Lapse of various vids on diamonds / human rights?] The biggest secret that social media let out? Lab-grown diamonds. They’re chemically identical, but less than half the price of natural diamonds. So the De Beers’ monopoly? It’s crumbling - and jewelers are panicking. — Do you still care about diamonds? Follow Michael Girdley for more business content ✅
One time as a young CEO: We couldn’t get a permit issued by a neighboring state regulator. Weeks went by with it sitting on some guy’s desk. Phone, faxes, zoom, etc. Nothing worked. I told the person in charge of our project: “Fly out there and sit in their office until you get the permit. Bring them donuts, humility, and kindness every day.” We got that permit in 2 hours. I learned: Much of business happens because you get on a plane and go meet in person. Zoom is fine but misses this core part of human nature. Get on the damn plane. — Do you still bother doing business in person?
Confronting an underperforming employee is never easy. Here’s my guide to make sure it doesn’t go off the rails. Schedule a one-on-one meeting with the employee. Send the invite at least one day in advance via email, using a generic title like “Discussion”. Write detailed notes on what you plan to cover in the meeting. Meeting tone: Once the meeting starts, avoid small talk and get down to the matter at hand immediately. Maintain a positive and constructive attitude. Focus on the facts, the impact, and the solutions. Do not focus on the personalities, the emotions, or point fingers. The beats of the meeting: Open by stating that this is going to be a difficult conversation about their performance issues. Make it clear that the goal of this meeting is to find a way for them to improve. This sets the tone. Next, describe the circumstances that have made this discussion necessary. Be specific about actions, dates and times, and tell them what the impact of their underperformance has been on the business and other co-workers. If applicable, tell them exactly where they’ve violated your policies. Get the employee’s perspective: Do they feel they have the necessary time, support, and resources to perform their job? Has anything changed in the business that has an impact on the employee’s performance? Has anything changed outside of the business, like a personal issue or health problem? Be clear about your expectations: Be specific, e.g. “Your job starts at 8 a.m. from Monday through Friday. You should be at your desk and available to answer client calls by that time every business day.” Together with the employee, make a detailed action plan you both understand and agree on. Set specific steps, deadlines, and targets. Include what you will do to support them. You should both sign and date the document. Schedule several followup meetings to check in on their progress. Once you’re done, update your meeting notes to include everything you discussed. Follow up: Send a recap of the meeting and your agreed upon action plan to the employee immediately after the meeting. If you have any to-do items on your side, get through them ASAP. You want them feeling the urgency of the situation. From there, things will go in one of two directions: Hopefully, the situation will improve. If it does, give that employee recognition. Refer specifically to what they’ve accomplished. Sometimes, things don’t get better. At that point, it’s time to move towards parting ways. — I hope this helps. Thoughts on this process? Comment below!
You’re never going to believe this… But the Tequila market is tanking. Tequila was on pace to be the #1 alcohol in the United States. But now? The market is cratering. Here’s why: Over the last decade, Tequila became the drink of choice, climbing the ranks to America’s second-favorite spirit after vodka. And it’s easy to see why. Consumers were sparing no expense—opting for premium drinks, craft cocktails, and bottles endorsed by A-list celebrities. We saw The Rock and Kendall Jenner dominate tequila. Even Diageo dropped $1 billion on Clooney’s tequila brand, Casamigos. But now? The party’s over. In 2024, demand for tequila flatlined. And consumers—who once proudly dropped $50+ on a bottle—are now hunting for cheaper pours. Because tequila is at risk on all fronts: There’s a generational shift toward less alcohol. At the same time, there’s a growing appeal for cannabis. And—most critically—a looming 25% Mexican import tariff that could send prices soaring. Although the tariff is on hold, if it goes through, import brands like Casamigos, Patrón, and Don Julio will see a massive hit. For smaller tequila importers, it could run them out of business entirely. So, tequila drinkers are panic-buying their favorite bottles before prices skyrocket. Is Tequila going to last or was it just a fad? Follow Michael Girdley for more business content ✅
You need a Chief of Staff. I hired one last year. I regret not doing it years ago. I doubled my productivity – and have a lot more fun now. Here's how I did it: Let’s start with what a Chief of Staff isn’t. This is NOT an Executive Assistant. While there are bits of menial work, the role is high-level. The CoS covers my “messy middle” of necessary projects. Too complex for an EA. But things that someone else could own/accelerate. — My CoS (hi @_robyn_smith!) does high-level projects like: • Lead a hiring process • Run a diligence process for one-off M&A • Choose a vendor • Run annual employee review process I can’t delegate these to existing teammates. But these things must get done. — There are many Chief of Staff “flavors” But this is mine: Robyn reports directly to me. And functions as a "smoke jumper": she parachutes into strategic spots. She’s a teammate in every big project and helps make things happen. A CoS is a force multiplier for me. Done right, a CoS has full access. They come to many/most meetings. Robyn knows my near-term and long-term plans. She’ll work with all my direct reports at some point. And there’s a high level of trust. — What I want in a Chief of Staff: • Smart • Good decision-making, and can make (somewhat) risky calls • Gritty • Attention to detail • Enjoys multitasking • Likable • Ambitious It’s an excellent opportunity for young early-career people. They get: • Exposure an early career person would never otherwise see • Often end up in a senior role • See the whole business • Move on (up) in 1–2 years Much better than getting a low-level jobby job! — For me, finding a CoS is easy: I just tweet about it. If you’re not there, I recommend two paths: • Network to find referrals (tons of young people want these jobs) • Identify hustlers in your current org and pitch them on the role It’s easier than you think. — You can check out Robyn’s Chief of Staff job description on my website. If you want the template for it, I'll send it to you for free: (Plus a guide to my hiring process) — The CoS role is getting more popular. Startup people are in the lead in using it. But more SMB people need to do this. It’ll change everything for you – I promise. — What are your thoughts on the CoS position? Follow Michael Girdley for more business content ✅
Business update! Over the last few years I’ve been building a community of small business leaders called Scalepath. As of this week, Rand Larsen will join as CEO (and acquire a majority of the company!). Rand Larsen is the perfect guy for this seat. He’s been driving all over the country for the last 3 years, building a peer group of his own through blood, sweat, and tears. Now he’s bringing the energy, focus, and time needed to level up this community. We’ve got some great stuff coming down the pike: - 35+ new faces, as Rand brings in his existing community members - Launching new peer groups (including some tailored to holdco owners!) - Doubling down on in-person events and retreats I’m super proud of what we’ve built, and I truly believe that joining a CEO community is one of the best career moves a leader can make. Welcome, Rand! Happy to answer any questions you have.
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