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In a time when companies are touting ways they have used AI to streamline operations, one restaurant chain stands out. Instead of trying to apply AI, this chain has gone back to the basics and fixed its foundations to become more efficient — and its latest quarterly report shows that the effort is paying off. 

According to Chris Caldwell, chief information officer of Chili’s-owner Brinker International, Chili’s is “not all in” on AI. Caldwell, who has been in the restaurant tech industry for nearly 30 years, recently told The Wall Street Journal that he has instead used his budget over the past two years to fix cracks in Chili’s foundation and strengthen its basic technology.

The initiatives include stronger Wi-Fi access, better payment systems and new devices for staff so they can provide better service to customers. 

Cutting back on robots

Simultaneously, Caldwell has pulled the plug on what he calls flashy but ultimately pointless initiatives, like robot servers. He has also decided to cut back on generative AI applications. Every technology initiative now has to serve the bigger purpose of enhancing food service and atmosphere, he said. 

“If a robot’s getting in the way and not helping us deliver a great guest experience, we’re going to get rid of them,” he added.

The technology initiative is part of a broader turnaround effort for Chili’s. Sara Senatore, a senior restaurants analyst at Bank of America, told the Journal that the plan has been successful: The company’s stock has risen more than 500% since June 2022. “The Chili’s turnaround has been nothing short of remarkable,” Senatore said.

According to Brinker International’s latest financial results for the third quarter ending March 25, Chili’s restaurant sales increased 4% when compared to the same period last year. Company sales overall were $1.46 billion, up from $1.41 billion the previous year. 

Caldwell decided to invest in the basics

Caldwell told the Journal that when he first arrived at Chili’s in February 2024, it was evident that the chain had neglected the basics. Poor Wi-Fi, outdated services and confusing ordering software were slowing staff down and hurting service quality. 

His priority was fixing the network. Over two years, the company upgraded Wi-Fi in 1,200 locations, renegotiated its Comcast contract, added cellular backup and installed new lines in sites of weakened connectivity. 

Caldwell did not disclose how much the project cost, but said that the effort wrapped up earlier this year. 

He added that better Wi-Fi set the stage for other tech upgrades in restaurants. 

In one early move, he bought 1,200 new laptops — one for each store manager. Before that, managers had to rely on the same desktop systems overloaded with running back-office operations. 

He also bought 23,000 new iPads that staff could use in place of old tablets to take orders. Up until that point, the tablets they used lacked quality battery life and weren’t functional for an entire shift. 

Caldwell said that his investments have contributed to 20 consecutive quarters of same-store sales growth. 

In a time when companies are touting ways they have used AI to streamline operations, one restaurant chain stands out. Instead of trying to apply AI, this chain has gone back to the basics and fixed its foundations to become more efficient — and its latest quarterly report shows that the effort is paying off. 

According to Chris Caldwell, chief information officer of Chili’s-owner Brinker International, Chili’s is “not all in” on AI. Caldwell, who has been in the restaurant tech industry for nearly 30 years, recently told The Wall Street Journal that he has instead used his budget over the past two years to fix cracks in Chili’s foundation and strengthen its basic technology.

The initiatives include stronger Wi-Fi access, better payment systems and new devices for staff so they can provide better service to customers. 

If you are building a personal brand and are not actively learning how to use AI tools like Claude and ChatGPT, you are leaving real results — and real revenue — on the table.

That might sound blunt, but the market is blunt right now. Increased visibility does not cut it anymore. You have to produce more content, articulate resonant ideas, build stronger positioning and stand out in ways that actually mean something. And it is less about volume than it is about precision.

At my company, D2 Branding, we work with speakers, founders, authors and podcast hosts whose ideas are their business. Their brands encompass a lot: social media, yes, but more broadly, reputation, intellectual property and market influence. Getting AI right has completely changed how we help them scale — but we did not get it right the first time.

How we got it wrong at first

Here is the honest part. Like many businesses, we first approached AI as if it were a productivity shortcut, using it to quickly spit out captions, blogs and emails. Efficient on the surface, sure. But we hit a wall pretty fast when we realized that premium personal brands need sharper thinking, not more content.

Established founders, speakers and industry leaders are not valuable because they post constantly and show up at the top of your Instagram feed. They are valuable because they can communicate clearly what others cannot, with more conviction and more precision.

Once that clicked, our approach changed. Instead of prompting AI with vague tasks like “write a post about leadership,” we started using it to challenge and deepen perspectives. We asked harder questions: Where is this founder’s philosophy being misunderstood? Which parts of their expertise are flying under the radar? What would make this message land harder?

That shift turned AI from a content-producing machine into a genuine thought partner. Now, we use it to hone keynote messaging, test frameworks and shape content that actually resonates.

Stop starting from zero

The second thing we got wrong was not building any real intelligence around the brands themselves. Every time we opened Claude or ChatGPT, we started from scratch — re-explaining the founder’s backstory, positioning, target audience, offers and tone of voice every single time. That approach was inefficient, and worse, it held us back from reaching real strategic depth. When a brand is built on ideas and voice, you cannot operate that way.

So we changed how we work. For every premium personal brand client we take on, we now build a structured ecosystem inside platforms like Claude Projects. Before a single prompt is typed, the system already knows the brand’s foundation — origin story, core philosophies, audience and positioning.

That adjustment turned AI into infrastructure. When a brand has a centralized intelligence system behind it, it can actually scale. Speakers sound aligned whether they are on stage, on a podcast or in copy on their website. Authors expand across channels without becoming scattered. The brand grows without losing what made it take off in the first place.

Take advantage of real data

Our third mistake, and possibly the biggest, was underestimating the power of real-world data. Most businesses are still guessing what their audience wants. They open an AI platform, type in a prompt and hope the response lands with their target audience. Premium brands should take the guesswork out of the equation altogether.

The move that changed our work the most was starting to feed AI actual data. We uploaded podcast transcripts, sales conversations, event recordings, customer questions, comments, DMs and Google reviews. Then we asked AI to show us patterns we might be missing. What emotional triggers keep surfacing? Where are people stuck but struggling to articulate why? Which ideas are resonating but need to be more fully developed?

The answers to those questions build stronger brands. When you use AI to identify the exact language, pain points and desires your audience has already been expressing, your messaging becomes far more effective. You are building an evidence-based strategy that makes people feel genuinely understood.

The AI advantage

This is where AI becomes one of the most valuable tools a personal brand can use. It can take human insight and sharpen it, help create messaging that converts into high-ticket offers, uncover themes that become books or keynote addresses and translate years of lived experience into scalable intellectual property.

We have shifted away from using AI to mindlessly pump out more content. Instead, we use these platforms to clarify thinking and strengthen positioning in crowded markets. AI helps us turn expertise into premium assets.

Do not make the mistake of thinking you just need more content to succeed. You do not. You need more precision, more data and more depth. AI alone will not build your personal brand — but used strategically, it can help you package years of expertise faster, communicate it more clearly and scale it further than you could on your own. In today’s market, that is a real advantage.

If you are building a personal brand and are not actively learning how to use AI tools like Claude and ChatGPT, you are leaving real results — and real revenue — on the table.

That might sound blunt, but the market is blunt right now. Increased visibility does not cut it anymore. You have to produce more content, articulate resonant ideas, build stronger positioning and stand out in ways that actually mean something. And it is less about volume than it is about precision.

At my company, D2 Branding, we work with speakers, founders, authors and podcast hosts whose ideas are their business. Their brands encompass a lot: social media, yes, but more broadly, reputation, intellectual property and market influence. Getting AI right has completely changed how we help them scale — but we did not get it right the first time.

To start your solo agency, you need a clear ideal client profile (ICP) and a transformative ideal client journey (ICJ). These two, when combined, define your agency’s niche. But knowing your niche is not enough. To sustain your agency, you need to have real paying customers. And as with all good things that last, your success all starts with your first.

If you’ve defined a valuable niche, attracting your first client will not be a result of market buoyancy. It will be a direct result of who you know and who knows you. That is to say, your first client will almost always come from your existing network.

In fact, I’m willing to bet that if you don’t already know your first client (perhaps even your first few clients), your prospects for long-term success as an independent expert are grim. You’re not yet ready.

So, before you even start thinking about quitting your full-time job to build the next big agency, make sure you have at least 20 individuals in your niche who you can ask for feedback. Notice that I say, “ask for feedback” and not “pitch to.” That distinction is important, and I’ll come back to it shortly.

Learn from my mistake

Before we dive into what you should do to find your first client, I want to share a mistake I made that almost cost me my agency before it even started. This is an important lesson that you can learn from.

I had spent the year between 2019 and 2020 deep in thought about how I believed I could enter the Salesforce CRM ecosystem as an independent advisor. I was confident in my strategies and had defined a clear client journey. In the fall of 2020, I officially founded my agency, MVRK.

In early 2021, my first potential client reached out through a referral. At the time, I still had a full-time job. After a couple of fantastic conversations that included most of the company’s senior leadership team, they asked me for a quote.

I eagerly prepared it and sent it off. After some back and forth, we reached a verbal agreement to start at the beginning of the following month. Full of eagerness following that verbal agreement, I handed in my three weeks’ notice with my employer.

Can you guess what happened next? That’s right. My potential client ghosted me! There was no signed paperwork. No deposit was paid. I made an amateurish decision that left me with nothing.

The lesson is simple: You don’t have a client until they’ve paid you.

Instead of pitching, ask for feedback

For most people, that would have been the end of the journey before it even started. But for me, it turned out to be a stumble before a fantastic sprint. That sprint has turned into a marathon that I’m still running. Today, I have a small team and over a dozen fantastic clients.

But that journey had to start with a first. So, how did I go about finding my first paying client after being ghosted? I did what all great entrepreneurs do. I turned my focus towards getting feedback on my strategy from people I trusted.

Instead of becoming desperate and begging my former boss to take me back, I asked former clients and business acquaintances for 20 minutes of their time. When I met with them, I did not try to pitch myself to them or position some form of partnership. Instead, I asked for their feedback on my designed client journey.

The question that worked the best for getting that feedback, especially from former clients, was this: “If you’d had the option to choose what I’m offering now when you originally made the decision to work with my team, how would that have influenced your thinking?” Feel free to use it yourself!

No matter what questions you ask, there are two signals that you need to tune into:

1. What resonates with your audience. The elements they respond to positively are the things you will use as the keystones of your pitch.
2. What your audience is confused about. Anything that does not make sense to the person you ask for feedback needs to be refined immediately.

These feedback conversations will be the most important time investment you make at the start of your solo journey. And unlike me, you should have those conversations before you quit your job!

Start to strengthen your network today

So, how did these conversations turn into my first client? It’s quite simple. A CFO I met with from a former client told his VP of Sales about my consulting firm. That VP reached out, asking for my help. After a conversation about what I offered, they signed a contract, paid the deposit, and we got to work.

They are still my client to this day, over five years later! You will almost certainly find your first client or clients in a similar way.

This is why I recommend that before you start working solo, you should be in a position where you can ask as many relevant people as possible for feedback; 20 is the minimum, closer to 50 is more ideal. If you are saying to yourself, “I don’t think I have 20 people I can ask for feedback,” then you’re not yet ready. Instead of rushing in, work hard to strengthen your network.

Even if it means you need to work for someone else for longer, it is worth the wait because the strength of your network will have a proportional impact on your early agency success.

To start your solo agency, you need a clear ideal client profile (ICP) and a transformative ideal client journey (ICJ). These two, when combined, define your agency’s niche. But knowing your niche is not enough. To sustain your agency, you need to have real paying customers. And as with all good things that last, your success all starts with your first.

If you’ve defined a valuable niche, attracting your first client will not be a result of market buoyancy. It will be a direct result of who you know and who knows you. That is to say, your first client will almost always come from your existing network.

In fact, I’m willing to bet that if you don’t already know your first client (perhaps even your first few clients), your prospects for long-term success as an independent expert are grim. You’re not yet ready.

Visa is slashing about 2,600 jobs, roughly 7% of its workforce. The layoffs will mainly hit technology and product teams, Bloomberg reports. CEO Ryan McInerney wrote to his staff that AI is “helping to accelerate this evolution and shape the way work gets done at Visa.”

But AI isn’t the whole story. According to a person familiar with the company’s reasoning, the cuts are also about freeing up money to reinvest in newer bets such as stablecoins, cross-border payments and business-to-business services.

Visa had about 34,100 employees at the end of its last fiscal year, more than triple what it had a decade earlier. “I have deep conviction that we are doing what is right for Visa, our clients and our partners,” McInerney wrote. Visa isn’t the only fintech company trimming staff. PayPal recently announced plans to cut 20% of its workforce, and Block has made similar moves in recent months.

Visa is slashing about 2,600 jobs, roughly 7% of its workforce. The layoffs will mainly hit technology and product teams, Bloomberg reports. CEO Ryan McInerney wrote to his staff that AI is “helping to accelerate this evolution and shape the way work gets done at Visa.”

But AI isn’t the whole story. According to a person familiar with the company’s reasoning, the cuts are also about freeing up money to reinvest in newer bets such as stablecoins, cross-border payments and business-to-business services.

Visa had about 34,100 employees at the end of its last fiscal year, more than triple what it had a decade earlier. “I have deep conviction that we are doing what is right for Visa, our clients and our partners,” McInerney wrote. Visa isn’t the only fintech company trimming staff. PayPal recently announced plans to cut 20% of its workforce, and Block has made similar moves in recent months.

This first-person, as-told-to essay is based on a conversation with Sean Henry, CEO and co-founder of Stord, a commerce enablement platform providing independent brands with the operational intelligence they need to compete with Amazon. Henry started Stord with co-founder and CTO Jacob Boudreau in 2015 while they were students at Georgia Tech.

The company recently closed a $250 million Series F round, valuing Stord at $3 billion (doubled in less than 12 months). Currently, Stord manages nearly $15 billion in annual GMV for brands like AG1, True Classic, Native and Seed Health, and delivered to nearly 20% of U.S. households last year alone. The piece has been edited for length and clarity. 

When I was about 8 years old, I started selling products on eBay. I still have the same eBay account: “Member since 2003” at the very top. I literally sold my Christmas presents and was stuck with this problem of asking my parents, “Hey, can you drive me to UPS?” “Can you give me cash if you can figure out how to get this money off eBay into your own bank account?”  

Later, I expanded to selling on Amazon. Eventually, I posted signs around our neighborhood saying we buy junk, phones and computers. Then I resold those items. 

Amazon Prime changes the ecommerce landscape

I saw a shift within ecommerce over the course of my life. When it was still new, consumers were impressed that they could buy something online and didn’t expect to buy everything online. 

Fast forward the next 10, 20 years, and because of Amazon Prime, Google and all these different companies, now consumers believe they can get anything online. Every SKU is available, and if they don’t like one brand, there are plenty of other options. Now consumers expect the product and leave reviews about the shipping experience. They’re judging that connection from the online purchase to the offline transaction.

When I was in high school, the summer before I started at Georgia Tech, I worked at an automotive manufacturer, which I’d previously bought parts from to resell. I wanted to meet the CEO and figure out how he built the business. So going into that first year of college, I still knew I wanted to be an entrepreneur. 

Realizing that everyone wants their online orders faster

I chose Georgia Tech because I was on a full-ride scholarship. I wanted to be an entrepreneur and keep my costs low. Plus, all my business resources and contacts were in Atlanta. ATDC, the Atlanta Tech Development Center, which is like a state-sponsored office space where they host classes that I could go to for free, was also tied to Georgia Tech. So I could learn about raising money, customer discovery, hiring and more.

After spending my whole life selling products online, I had this realization: Everyone is going to want stuff faster, cheaper and online forever. If you ask any consumer in the world, “Hey, if every place you shop gave the same experience as Amazon, would that be better off for you?” They’re all going to say yes. It’s almost too big and too hairy and too obvious a problem to tackle. But I wanted to do that. 

When you’re focused on a big audacious problem, the hardest thing to do is figure out your wedge into the value chain. Where do you start in a way that’s strategic enough to provide enough value to get your first customer, but then still have enough legs to get you where you want to go long term, not take you in the wrong direction? Depending on that wedge of value, you could end up going a lot of different directions.

A typical brand has a couple facilities: Amazon has hundreds

We realized that if you step back from what makes Prime incredible, it’s all about the warehouses and fulfillment centers. It’s all about where those are compared to consumers. Normally a brand has one or two facilities, whereas Amazon has hundreds, and they’re everywhere.

Then there’s the real-time consideration when you’re checking out online and saying, “I’m ordering this,” and learning when you can expect to receive the product. Typically, the technology is so fragmented that it’s not until potentially 12 hours later that the brand is even deciding which piece of inventory to send or which fulfillment center it should ship from to you.

I was 18 the day I registered for Stord LLC. I put $5,000 to $10,000 of savings in the business to get us going. That’s not enough to open a warehouse. So we decided to call existing warehouses and say, “Hey, if I bring you volume of 10 or 100 or 500 customers one day, but you’re just dealing with me, and I build a network of dozens of you regionally placed across the U.S., bringing you revenue and the tech to enable you, will you take volume on our behalf and partner with us?” And they were all like, “Absolutely. It sounds too good to be true.”

Dropping out of college at 19 to go all-in on the business

Early on, I was trying to convince people to work for a 19-year-old who was still in classes on the side. Talent, capital and time as a young founder and student were the hardest things. It was hard to convince real employees to work for me and very hard to get investors. At one of the first firms we pitched, an angel investor said, “Well, if I give you $200,000, I don’t know why the company’s worth any more than $200,000.” Eventually, I had to make the hard decision to drop out of college. I became a Thiel Fellow and went all-in on Stord.

The hardest thing we ever had to do was build a software and an operations culture in one. To hire product managers and engineers, industrial engineers and associates in fulfillment centers, and get them to work together well. Because they’re typically very different cultures, businesses, backgrounds and corporate environments. 

Harnessing AI to address issues in the warehouse

One of the great opportunities in the next decade or two is how do you have not just engineers be faster with AI, but literally every person in the workforce to be faster and more effective? It’s the same thing we’ve been trying to solve in the warehouse for a long time. You’re not trying to automate to have no people in a warehouse. You’re trying to say, “How do I use automation and software to make quality of life 10 times better for that employee, and also faster and more efficient for myself at the same time?”

Today, Stord is a comprehensive platform where we span physical infrastructure, software, robotics and AI, and we help brands tackle this Prime-like delivery question, from physical shipping through checkout technology, consumer-facing tracking, returns and more. We have so many different capabilities and kinds of businesses embedded in this big solution we built for brands that we couldn’t be the Amazon for everybody else from day one. Frankly, a lot of the agentic robotics, applied AI and more that drive our network today weren’t even available back then when we started. 

Stord will see nearly $1 billion in annual revenue this year

Now, we power deliveries to over a fourth of U.S. households, about $17 billion of commerce. We’ll do almost $1 billion of revenue this year as a business. We’ve been chasing this level of Amazon Prime speed and cost, and we’re increasingly close. The average business out there delivers in four to seven days for $12 to $15. Amazon’s delivering in a day to a day and a half for $4 to $5. Then you have Stord delivering in maybe two to three days for $5 to $6. We’re using our position of scale and technology to keep compounding this level of speed and cost to truly compete. 

We’re also investing a ton in Stord Labs, our physical intelligence lab here in Atlanta where we train AI and robotics on our live orders across all of our data and almost 100 facilities. That becomes our proprietary training dataset, along with video from our facilities. Then we partner with leading robotic and frontier model companies to both train their models and their robots on demand planning. 

If you step back, our highest costs and/or the biggest drivers of our speed and our service to consumers are decisions, labor and deliveries. Now AI is driving decisions. Labor is going from robotics that have been really problematic in fulfillment centers, oftentimes because of the remapping cost — meaning, the second a robot sees a SKU it’s not familiar with or a slight variance, you often get the whole system down — to agentic robotics that can solve deviations from the happy path themselves.

So far, we’ve really changed the lives of our brands. We’ve made it faster for them and cheaper for them. Next, we’re really going to change the lives of the consumers.

This first-person, as-told-to essay is based on a conversation with Sean Henry, CEO and co-founder of Stord, a commerce enablement platform providing independent brands with the operational intelligence they need to compete with Amazon. Henry started Stord with co-founder and CTO Jacob Boudreau in 2015 while they were students at Georgia Tech.

The company recently closed a $250 million Series F round, valuing Stord at $3 billion (doubled in less than 12 months). Currently, Stord manages nearly $15 billion in annual GMV for brands like AG1, True Classic, Native and Seed Health, and delivered to nearly 20% of U.S. households last year alone. The piece has been edited for length and clarity. 

When I was about 8 years old, I started selling products on eBay. I still have the same eBay account: “Member since 2003” at the very top. I literally sold my Christmas presents and was stuck with this problem of asking my parents, “Hey, can you drive me to UPS?” “Can you give me cash if you can figure out how to get this money off eBay into your own bank account?”  

Many entrepreneurs see building a company and eventually selling it as the ultimate achievement. My first exit happened by accident, and I didn’t even know I’d had one.

I was 19, mowing lawns because I’d bought a mower, and walking to jobs cost me nothing. The day I landed a real job with health insurance, I planned to just stop. Tell the customers thanks, move on. Then a guy knocked on my door and offered to buy my client list. I had no idea you could sell something like that. I took the money, walked away and spent the next 20 years realizing how many founders never figure out what I stumbled into at 19. A small business is an asset, and assets have value beyond what their owners think.

I’ve now sold four companies myself and mentored somewhere between eight and twelve other founders through their own exits. Acqui-hires, fire sales, the occasional clean win. Most of these don’t make the news. When you read “acquired for an undisclosed sum,” half the time it means somebody just dodged bankruptcy.

This article is not for you if you’re trying to engineer a $50 million exit. Above roughly $8 million, you’ll be working with bankers and brokers who handle most of what I’m about to teach you. This is for the founder who’d be ecstatic with a $900,000 outcome and can’t get a broker to return a call because the commission isn’t worth their time. That’s most small business owners. According to BizBuySell’s 2024 Insight Report, the median small business sale was around $350,000, with the average SDE multiple sitting at just 2.57 times across all industries. This is the range where the most money gets left on the table, because nobody’s in the room telling you what your business is actually worth.

One caveat, and I want to be clear about it. I do not advise starting a company for the exit. Start it because you’re solving a real problem for real people. But the smartest founders I know do both. They solve the problem and structure the business so that when Google comes calling, they’re ready.

If you’re an entrepreneur with aspirations to exit someday, here’s what you need to know before you sit down across from a corp dev team.

Your client list is an asset, even in a service business

This is the lesson the lawnmower guy taught me. A clean client list — names, what they’ve paid you, how long they’ve been with you over the last three, six, or twelve months — forms the basis of almost every small business valuation. You can place a defensible number on those customers based on their average annual spend.

20 customers paying you $20,000 a year? That’s a $400,000 base valuation before anyone even looks at your operation. Most service business owners have never thought about their book of business this way. They think they’re selling their time. They aren’t. They’re sitting on an asset.

Contracts aren’t bureaucracy. They’re proof.

The value of a contract isn’t that the customer is bound by it. The value is that they were willing to sign it in the first place.

I’ve watched two nearly identical businesses get wildly different offers because one had signed agreements and the other had handshake relationships and a long track record. The handshake guy was actually more profitable. He still got less money, because the buyer can’t underwrite a handshake. A signature is evidence that the relationship is real, the revenue is contracted, and it doesn’t walk out the door when you do. Put it in writing, even retroactively. Especially retroactively.

The EBITDA tax-avoidance trap

This one breaks my heart because I’ve watched it kill deals.

EBITDA (earnings before interest, taxes, depreciation and amortization) is the number buyers multiply to land on your valuation. And what do small business owners do every December? They buy inventory they don’t need. They prepay expenses. They run personal stuff through the business. All of it perfectly legal, all of it designed to lower EBITDA so they pay less in taxes.

It may feel smart in April, but it’s catastrophic at exit.

Buyers want numbers. If you’re planning to sell in the next three years, start showing your real profit and pay the real taxes on it. Your financial statements need to reflect what actually happened in the business. You cannot sell your company for seven times the money you spent three years pretending didn’t exist.

I tell every founder I mentor that the day you decide you might exit someday is the day you stop optimizing for tax minimization and start optimizing for clean books. The tax savings are pennies. The valuation hit is millions.

The email list multiplier

A real customer email list is worth its weight in gold. When I sold Black Helmet to a public buyer in 2016, the deal included a list of nearly 200,000 actual customers. These were not scraped names, not free lead magnets, but actual paying customers. That list alone was enough to push the deal across the threshold the buyer needed to justify it internally. They put a price per name based on what it cost them to acquire one through advertising — somewhere around $2.50 a head.

Do the math on that. If you’ve got a list with real engagement and real purchase history, that’s a line item on your valuation. Most founders don’t even know what their open rates are, let alone what a buyer would pay for the list. Find out.

The customer concentration killer

Here’s a question every corp dev team will ask within the first thirty minutes: what percentage of your revenue comes from your largest customer?

According to FOCUS Investment Banking, when a single customer represents too much of a business, the transaction valuation can be reduced by 20-35%. Most buyers start flagging concentration risk above 15-20%, and above 30% you’re looking at serious multiple compression — if the deal happens at all. It doesn’t matter how good the relationship is or how long they’ve been with you. From the buyer’s perspective, you’re not selling them a business. You’re selling them one customer, and one phone call from being out of business.

If you’re a year or two away from selling, this is the most fixable problem on the list. Diversify. Push hard on sales. Get your biggest customer below 15% of revenue before you ever walk into a conversation. The work you do this year directly translates to multiple expansion next year.

Take the ‘what happens if you get hit by a bus’ test

This is closely related, and equally lethal. If the business cannot run without you in it, you don’t have a business. You have a job that pays well.

Buyers will sniff this out instantly. Who handles sales? You. Who manages the key vendor relationship? You. Who knows where the bodies are buried in operations? You. Every “you” answer cuts the multiple.

The fix is unsexy and slow. Hire, document, delegate. Write down the SOPs. Put a sales manager in place. Train someone to handle the relationships you’re holding personally. A business that runs without the founder sells for meaningfully more than the same business that doesn’t, even if the financials are identical.

Technology acquisitions: flip the math

Here’s the leverage most founders miss when they’re being acquired by a much larger company.

Say you’ve built a product doing $1 million a year at 30% gross margins. EBITDA of $300,000. Buyer offers you seven times EBITDA, so $2.1 million. That feels like a real number. You’re tempted to take it.

But now look at it from their side. They have 50,000 customers. Your product, dropped into their distribution, can plausibly add $10 million to their top line in year one. You’re not selling them what you built. You’re selling them what they can do with what you built.

That reframe changes everything about the negotiation. The question isn’t what your business is worth standing alone. The question is what it’s worth inside their machine. If you walk in with the standalone number, you’ll get the standalone price. If you walk in with the integrated number — with the math, the customer overlap analysis, the realistic year-one synergy — you’re playing a different game.

Build toward recurring revenue (this is the headline lever)

If you take one thing from this article, take this: according to BizBuySell, the average small business sells for 2.57 times seller’s discretionary earnings. Now look at the SaaS side. SaaS Capital, which has tracked private B2B SaaS valuations since 2007, reports the current band sits at 5.5x to 8x annual recurring revenue, with the public SaaS Index median at 7.0x. Same revenue dollars, double or triple the exit valuation.

The difference is predictability. Buyers will pay a massive premium for revenue that shows up every month without you having to re-sell it.

You don’t have to be a software company to get some version of this. You can take a service business and platform-ize it. Build a login, a dashboard, a recurring payment system, a deliverable that lands every month for $500 or $5,000 instead of being a one-off engagement. You’re now selling subscriptions instead of services. The multiple expands overnight.

It’s not personal. It’s not your baby.

When a lowball bidder opens with an insulting number, founders take it personally. They get angry. They get defensive. They get rattled, and they walk away from the conversation entirely, not realizing what felt like an insult was just the opening offer.

You may be tempted to turn over the table and walk away, but don’t. That’s literally the job. The buyer’s role is to acquire you for as little as possible. Your role is to know what you’re worth and refuse to flinch. It’s not personal, and it’s not your baby. People don’t sell their babies. They sell businesses. You say $8, they say $1; the truth is somewhere around $4 to $5, and the game has officially started. If you don’t have the data — the customer list, the contracts, the clean books, the integration math, the answers to the customer concentration and key-person questions — you’re going to lose that game. They’re experienced. You aren’t.

So before you sit down at the table, sit down with forty other tables first. Send 40 cold emails to corporate development teams on LinkedIn. Four will reply. Two will agree to meet. Take those meetings even if you’re not selling. Especially if you’re not selling. The questions they ask you will teach you what actually matters in a valuation. Then build your business so that when the real conversation comes, you’ve got the answers ready.

That’s the whole game. Build the asset. Know what it’s worth, and don’t blink.

Many entrepreneurs see building a company and eventually selling it as the ultimate achievement. My first exit happened by accident, and I didn’t even know I’d had one.

I was 19, mowing lawns because I’d bought a mower, and walking to jobs cost me nothing. The day I landed a real job with health insurance, I planned to just stop. Tell the customers thanks, move on. Then a guy knocked on my door and offered to buy my client list. I had no idea you could sell something like that. I took the money, walked away and spent the next 20 years realizing how many founders never figure out what I stumbled into at 19. A small business is an asset, and assets have value beyond what their owners think.

I’ve now sold four companies myself and mentored somewhere between eight and twelve other founders through their own exits. Acqui-hires, fire sales, the occasional clean win. Most of these don’t make the news. When you read “acquired for an undisclosed sum,” half the time it means somebody just dodged bankruptcy.

Steve Ells invented the burrito bowl, and now he thinks people might be suffering from “slop bowl” fatigue. In an interview with the Wall Street Journal, the founder and former CEO of Chipotle talks about his new concept, Counter Service, a sandwich shop that launched last year in New York City and plans to expand to Charlotte and Dallas next year.

Counter Service specializes in slow-roasted meats, homemade bread and made-in-house sauces and relishes. The concept pivots away from an earlier post-Chipotle venture, a vegan restaurant built around robotics. It uses technology that flags incorrectly assembled orders, part of a broader system predicting sales using traffic, transit and weather data.

Ells says the appeal is in the details that most chains skip. “The pieces of meat are not perfectly shaped like the things you see in these chain sandwich places,” he said. “We’re making all of our sauces and relishes and garnishes. It’s difficult to do these things.” After 27 years eating Chipotle nearly every day, he says he now eats at Counter Service just as often.

Steve Ells invented the burrito bowl, and now he thinks people might be suffering from “slop bowl” fatigue. In an interview with the Wall Street Journal, the founder and former CEO of Chipotle talks about his new concept, Counter Service, a sandwich shop that launched last year in New York City and plans to expand to Charlotte and Dallas next year.

Counter Service specializes in slow-roasted meats, homemade bread and made-in-house sauces and relishes. The concept pivots away from an earlier post-Chipotle venture, a vegan restaurant built around robotics. It uses technology that flags incorrectly assembled orders, part of a broader system predicting sales using traffic, transit and weather data.

Ells says the appeal is in the details that most chains skip. “The pieces of meat are not perfectly shaped like the things you see in these chain sandwich places,” he said. “We’re making all of our sauces and relishes and garnishes. It’s difficult to do these things.” After 27 years eating Chipotle nearly every day, he says he now eats at Counter Service just as often.

Most outreach asks for value and offers none in return. The businesses that earn links and citations publish proof first.

Every Monday morning, I open my inbox and find the same email waiting 30 or 40 times. The subject line says “quick question” or “collaboration opportunity.” The body asks me to add a link to an article I wrote three years ago, points to a homepage and offers nothing in return.

I run a digital PR agency called ESBO and publish a handful of industry sites, so I sit on both sides of this trade. I send outreach for a living, and I delete it for a living. The deleting takes less time every year, because the emails all share one flaw: they ask, and they bring nothing an editor can use.

None of this is personal. Muck Rack’s State of Journalism 2026 survey found that 88% of journalists delete pitches that miss their beat, and about half say they seldom or never respond to pitches at all. What interests me is the small group of requests that get a yes, because the reason is usually unglamorous and repeatable: they arrive carrying proof.

Editors link to evidence, not to companies

When I cite a source in an article, one question decides it. Does this page back the claim I am making? A homepage backs nothing, and neither does a services page with a paragraph about passion for excellence.

What backs a claim is a number attached to a method. In the same Muck Rack survey, 40% of journalists named original data or research among the elements they value most in a pitch. That matches what I see in my own inbox so closely it barely counts as a finding.

Imagine two emails from the same moving company. One says it is a trusted leader in relocation services. The other says it compared 2,400 quotes against final invoices this year and found that the typical move cost 23% more than the estimate. The first email is marketing. The second is a source, and I would cite it by Friday.

The data you already have is the asset

You do not need a research department for this. Any business that has operated for a few years is sitting on records nobody else can see: quotes, invoices, support tickets, return reasons, delivery times and refund rates. That pile of admin is the raw material.

An accounting firm could publish how many of its clients file in the final week and what the panic costs them. An online store could break down its return reasons by product category. A recruiter could report how long candidates in one niche stay in their first job. The work is not complicated. It comes down to pulling six to 12 months of records, removing anything that identifies a client and writing up what you found.

Honesty about scale matters here. If your dataset is 300 projects, say it is based on 300 projects. Small and real beats big and vague, and editors can tell the difference in seconds.

One good number outworks a hundred cold emails

There is a bigger reason to do this in 2026, and it is the way answers now get assembled. A Pew Research Center analysis of real browsing behavior found that when an AI summary appears on a search page, people click a traditional result in 8% of visits, down from 15% without one. Clicks on the sources cited inside those summaries happen about 1% of the time.

You could read that as a reason to give up on visibility. I read it the opposite way. If answers are assembled from a handful of sources and almost nobody clicks through, the only durable position is being one of those sources, because your name travels with the number even when the visit never happens.

I have watched this on my own sites. Articles built around one original figure keep getting picked up in roundups, newsletters and AI answers years after publication, while pure opinion pieces fade within months. Something else happens too, and it still amuses me: once you become the source, the emails reverse direction. People start writing to you, asking to be included in the next update.

The easiest number to copy wins the citation

Packaging decides whether any of this gets used. Put the main finding in the title, then repeat it in the first hundred words as one plain sentence someone can lift. Explain the method at the bottom. Refresh the numbers once a year so the citation stays current and earns a second round of pickups.

And do not gate it. I have lost count of the promising reports I abandoned because the figure I needed sat behind a lead capture form (abandoned is generous; I closed the tab in five seconds). An editor on deadline will not fill in a form, and neither will a language model.

The hit rate is nothing to brag about. Most of these assets get ignored, and in my experience roughly one in three earns real pickup. The one that lands pays for the other two many times over, which is still a better return than any cold sequence I have ever run.

I still send outreach every week, so this is not a sermon against asking. Asking just stopped working on its own. If you want links, mentions and a place inside AI answers, give people something that survives the delete key. Publish one number this quarter that nobody else has, then watch what starts showing up in your own inbox.

Most outreach asks for value and offers none in return. The businesses that earn links and citations publish proof first.

Every Monday morning, I open my inbox and find the same email waiting 30 or 40 times. The subject line says “quick question” or “collaboration opportunity.” The body asks me to add a link to an article I wrote three years ago, points to a homepage and offers nothing in return.

I run a digital PR agency called ESBO and publish a handful of industry sites, so I sit on both sides of this trade. I send outreach for a living, and I delete it for a living. The deleting takes less time every year, because the emails all share one flaw: they ask, and they bring nothing an editor can use.

When we started building what became the Amazon Web Services (AWS) Database products, plenty of smart people believed enterprises would never trust the cloud with their databases. Today, that market generates more than $107 billion in annual revenue.

The experience taught me something I have carried into every leadership role since. If you wait for consensus, someone else will build the future while you are still debating it. That does not mean making reckless bets. It means learning how to recognize evidence before everyone else does and having the discipline to act on it. Here are four lessons that changed the way I think about innovation and leadership.

Look for constraints, not trends

Most companies spend their time chasing the next technology trend. I have found it is far more valuable to look for the problems customers have quietly accepted as part of doing business.

When we were building AWS database services, we realized enterprises were investing enormous amounts of time, money and engineering talent managing database infrastructure. They were provisioning servers, maintaining licenses, planning for failover and keeping systems running. None of that work created a competitive advantage. It was simply the cost of keeping the lights on.

That observation became the opportunity. If we could remove that burden, engineering teams could spend more time building products instead of maintaining infrastructure. That is why you need to know where your customers are investing time and resources without creating meaningful value. Those constraints often reveal the most important opportunities for development.

Build conviction with evidence

One of the biggest misconceptions about innovation is that successful leaders have extraordinary confidence. My experience has been the opposite. The best decisions come from gathering evidence, even when the market hasn’t caught up yet.

There was tremendous skepticism about whether enterprises would trust a cloud provider with something as important as their databases. We didn’t ignore those concerns. We studied early customer behavior, watched how managed services changed engineering productivity and kept testing our assumptions against real-world results. Every customer who succeeded strengthened our conviction because the evidence kept pointing in the same direction.

That is why I believe evidence is what separates conviction from stubbornness. Stubbornness ignores facts that challenge an idea. Conviction becomes stronger because it keeps collecting evidence before making bigger commitments. Before making your next major investment, spend less time gathering opinions and more time studying early adopters. The people already experimenting with the future will teach you far more than the people predicting it.

Sell the problem before the solution

Many leaders struggle to gain support because they start by pitching a bold vision.

We learned that internal alignment became much easier when we started with the problem instead of the solution. Before asking anyone to believe in managed database services, we made sure they agreed that the existing approach was becoming unsustainable. Once people acknowledged the problem, conversations about a different future became much more productive.

This approach works inside every organization. Before presenting your next proposal, ask whether everyone agrees the current state deserves to change. If the answer is no, spend your energy building alignment around the problem first. Then present your solution as the logical next step.

Move faster than consensus

One lesson stands out more than any other. Waiting for certainty feels responsible, but it often becomes the biggest competitive risk.

When people look at AWS today, they often assume our biggest advantage came from being early. It didn’t. Our biggest advantage came from learning earlier.

Every customer who adopted AWS database services gave us feedback we could never have created inside the company. We saw real workloads, real failure modes and edge cases that no amount of internal testing would have uncovered. Every lesson made the product stronger and helped us make better decisions.

By the time the market broadly accepted managed database services, we had years of production experience behind us. That institutional knowledge wasn’t sitting in a document. It was built into our architecture, our operational playbooks and the instincts of the engineering team. Competitors were trying to catch up with years of accumulated learning.

That is why I tell leaders that speed to market is really speed to learning. Revenue comes later. Learning starts on day one, and every customer interaction expands your advantage.

A practical way to build that advantage is to separate reversible decisions from irreversible ones. If a decision can be changed later, make it quickly and learn from the outcome. Reserve longer discussions for the decisions that truly reshape the business. The faster you learn, the harder you become to catch.

Three ways to build the next market

If you are trying to build something people don’t fully believe in yet, start here. Stress-test your conviction. Look for evidence from early adopters instead of relying on market opinions. Study what almost caused them to give up, because that is where the strongest insights often appear. Build agreement around the problem. Before presenting a solution, make sure key stakeholders agree the current approach is no longer good enough. Alignment becomes much easier when everyone starts from the same reality. Compress your decision cycles. Move quickly on decisions you can reverse and protect time for the ones you cannot. Speed is less about making perfect decisions than creating more opportunities to learn.

Markets are built by leaders who recognize meaningful problems early and keep moving while everyone else waits for certainty. That is the lesson I learned helping build a business few people believed could exist — and it is one every leader can apply, regardless of industry.

When we started building what became the Amazon Web Services (AWS) Database products, plenty of smart people believed enterprises would never trust the cloud with their databases. Today, that market generates more than $107 billion in annual revenue.

The experience taught me something I have carried into every leadership role since. If you wait for consensus, someone else will build the future while you are still debating it. That does not mean making reckless bets. It means learning how to recognize evidence before everyone else does and having the discipline to act on it. Here are four lessons that changed the way I think about innovation and leadership.

Look for constraints, not trends

Most companies spend their time chasing the next technology trend. I have found it is far more valuable to look for the problems customers have quietly accepted as part of doing business.

Jefferson Simmons was 20 years old and about to be homeless. His entire fraternity house was getting renovated, and every rental in town wanted nothing to do with a group of college guys. 

On a whim, he flipped a Zillow toggle from rent to buy and found a mismarketed three-bedroom house that was actually a 2,700-square-foot property with three extra rooms in the basement. He pitched his parents to co-sign, negotiated the seller down seven rounds to $178,000, and moved his fraternity brothers into the basement. 

Nine years later, he’s walked away from law school, built partnerships with an uncle and a private investor, and grown that first accidental deal into 17 properties and 39 doors. 

Here’s how he built it.

You were a sophomore in college, with no income and no credit. How did you actually get that first house?

I’d saved money since high school from selling firewood and doing livestock projects, and I got a full academic scholarship right before graduation, so I had a nest egg but no income a bank would lend against. 

I went home and pitched my parents using an Excel spreadsheet and a full 10-year pro forma showing rent increases, and they agreed to co-sign. I negotiated the seller down from their asking price to $178,000 over seven rounds of back-and-forth, partly because I knew from the listing agent that the family was highly motivated to sell, and partly because I genuinely had no more room to go higher. 

My mortgage payment has stayed the same the whole time, about $1,300 a month, including taxes and insurance. I rented it the first year for $1,600, and it’s currently leased through 2027 at $3,100 per month.

Your second deal was a foreclosure auction property you bought with your uncle. How did that partnership actually work?

I saw a duplex next door to my first house heading to a bank foreclosure auction, and I had zero money to buy it myself. My uncle, who’d built a portfolio of his own and was a big mentor to me, agreed to fund it as a money partner. 

We could only look through the windows before the auction since we couldn’t access the interior, so we did our underwriting from the driveway over coffee, and he told me we could afford up to $140,000 after repairs. Then he left the country on a trip and told me he’d be completely unreachable, so I was the one bidding live from my laptop. 

I got it to $100,000, and even though it didn’t technically meet the bank’s reserve, they wanted it off their books and took the offer anyway.

You walked away from law school after one semester to go all-in on real estate. What made you pull the trigger?

I sat in my first law school class, and they described the bell curve of graduates, meaning that where you rank determines your salary. I realized I wasn’t going to be at the top of that curve, and I’d be leaving school with over $100,000 in student loan debt for the privilege. 

I’d already closed two real estate deals by that point and had real proof of concept, so I decided I’d rather take on another mortgage that pays me back than debt that doesn’t. I left after one semester, worked as an insurance underwriter making $42,000 a year, got my real estate license on the side, and kept buying single-family homes for years while working two jobs.

You’ve done some creative financing since then, including turning a house sale into a line of credit. Walk us through that deal.

I was working as an agent for a cash-buyer client during an insane seller’s market where every listing was already pending within hours. He was getting frustrated that we couldn’t move fast enough on anything. 

Around the same time, tenants in a house I owned asked to break their lease early to buy their forever home, and I let them out of it. That left me with a vacant house I knew fit exactly what my client wanted. 

Over dinner, I gave him two options: I’d sell it to him for $25,000 more than I paid, or I’d sell it to him at my exact cost if he’d write me a $200,000 private line of credit instead. He laughed, looked at the house with his wife over FaceTime, and agreed to the line of credit. 

Three months later, I used it to buy a $171,000 house, and he wired the full balance the day of closing with no appraisal and no bank fees. I pay him 7.25% interest, which beats his T-bill returns and costs me less than a bank would. We’ve since done several more deals together and become genuine friends.

What does your portfolio look like today, and what’s actually driving your growth now?

I’m at 17 properties, 39 doors total, and I own all of them outright except for a minority stake in a 15-unit I hold with a few partners. Altogether, that’s about $20,000 a month in cash flow. 

A big unlock along the way was sweat equity: I helped my uncle renovate a 12-unit he bought in 2019, doing new kitchens, floors, and paint myself, in exchange for a 10% stake, which let me build equity without putting up much of my own cash. I also stopped thinking I could only buy one house a year by saving for the next down payment, since that mindset was actually limiting how fast I could scale. 

Between the family partnership, the private line of credit, and just getting comfortable asking people directly for capital, that’s what let me go from one deal a year to where I am now.